Homesinorlando.forsale Search Results

$4,772,500

An architectural gem in the heart of the Vias, this one-of-a-kind modern, custom residence masterfully crafted in 2019 by renowned builder Z Properties, Inc. Rarely does a single-story home of this caliber and scale become available combined with being on one of the best addresses in all of Winter Park! Offering nearly 4,900 square feet of refined living space under air (which includes a noteworthy 551-square-foot lanai, fully finished and separate zone air-conditioning) encompassing over 5,400 square feet total under roof, all tastefully designed with an emphasis on clean lines, organic textures and exceptional indoor-outdoor flow. Beyond its striking curb appeal, the home opens to reveal expansive living spaces grounded by wide-plank hardwood floors and bathed in natural light from soaring cathedral ceilings and oversized windows. A seamless open layout connects the living and dining areas with a central gathering area anchored by a sleek linear gas fireplace. Award-winning chef-designed kitchen is framed by a dramatic wall of glass and features premium Wolf and Sub-Zero appliances, including an eight-burner gas cooktop, integrated refrigerator, double built-in ovens, Miele coffee system, warming drawer, Scotsman ice maker, high-level custom cabinetry and more, flanked by dual wine columns. The primary retreat is in its wing, complete with a 20-by-10-foot custom walk-in closet and a spa-inspired bath with a soaking tub and oversized walk-in shower featuring multiple shower heads. The home's most captivating element is the fully enclosed, air-conditioned 29-by-17-foot lanai, accessible through disappearing glass doors that create a seamless transition from indoors to out. This sophisticated outdoor living space includes a full summer kitchen, alfresco dining area, lounge with gas fireplace and motorized screens for further flexible utilization. Just beyond, a heated lap pool is framed by lush bamboo landscaping, creating a serene and secluded outdoor living environment. Another special feature is a secluded casita, which offers an ideal space for guests or multigenerational living. Two additional bedrooms with en suites, each with walk-in closets, complete the three-way split flexible bedroom layout along with a well-appointed utility/mud room entry off the oversized two-car garage. Ideally near Winter Park Racquet Club, Interlachen Country Club and accessible to Park Avenue, this exceptional residence also offers an extraordinary blend of modern design, luxurious functionality and premier location. Winter Park living at its finest!

4 Beds ⋅ 5 Baths ⋅ Sicilian Shores Rep 02 SubDv. ⋅ 32789 Zip Code

An architectural gem in the heart of the Vias, this one-of-a-kind modern, custom residence masterfully crafted in 2019 by renowned builder Z Properties, Inc. Rarely does a single-story home of this caliber and scale become available combined with being on one of the best addresses in all of Winter Park! Offering nearly 4,900 square feet of refined living space under air (which includes a noteworthy 551-square-foot lanai, fully finished and separate zone air-conditioning) encompassing over 5,400 square feet total under roof, all tastefully designed with an emphasis on clean lines, organic textures and exceptional indoor-outdoor flow. Beyond its striking curb appeal, the home opens to reveal expansive living spaces grounded by wide-plank hardwood floors and bathed in natural light from soaring cathedral ceilings and oversized windows. A seamless open layout connects the living and dining areas with a central gathering area anchored by a sleek linear gas fireplace. Award-winning chef-designed kitchen is framed by a dramatic wall of glass and features premium Wolf and Sub-Zero appliances, including an eight-burner gas cooktop, integrated refrigerator, double built-in ovens, Miele coffee system, warming drawer, Scotsman ice maker, high-level custom cabinetry and more, flanked by dual wine columns. The primary retreat is in its wing, complete with a 20-by-10-foot custom walk-in closet and a spa-inspired bath with a soaking tub and oversized walk-in shower featuring multiple shower heads. The home's most captivating element is the fully enclosed, air-conditioned 29-by-17-foot lanai, accessible through disappearing glass doors that create a seamless transition from indoors to out. This sophisticated outdoor living space includes a full summer kitchen, alfresco dining area, lounge with gas fireplace and motorized screens for further flexible utilization. Just beyond, a heated lap pool is framed by lush bamboo landscaping, creating a serene and secluded outdoor living environment. Another special feature is a secluded casita, which offers an ideal space for guests or multigenerational living. Two additional bedrooms with en suites, each with walk-in closets, complete the three-way split flexible bedroom layout along with a well-appointed utility/mud room entry off the oversized two-car garage. Ideally near Winter Park Racquet Club, Interlachen Country Club and accessible to Park Avenue, this exceptional residence also offers an extraordinary blend of modern design, luxurious functionality and premier location. Winter Park living at its finest!

765 Via Lugano, Winter Park

$1,277,000

Welcome to a truly exceptional residence nestled on a quiet, tree-lined street in one of Winter Park’s most desirable neighborhoods. This custom-built gem offers a blend of elegance, craftsmanship, and resort-style comfort, featuring 3 bedrooms, 3.5 baths, and 2,595 square feet of thoughtfully designed living space. As you enter, you'll be immediately drawn to the tranquil, resort-like ambiance created by the centerpiece of the home: a screened-in courtyard with a heated saltwater pool and spa, perfect for relaxing or entertaining year-round. Adjacent to this serene space is a private guest casita complete with a full bath and separate entrance, ideal for in-laws, visitors, or an independent-minded teen. Step into the main house, and you will be immediately captivated by the 15-foot Frank Lloyd Wright-inspired rock wall in the stunning Living Room. The 12-foot ceilings give the space a seemingly endless light and airy feel. Overlooking the great room is a fully equipped chef-inspired kitchen where creating meals will be a breeze with an abundance of cabinets, gleaming quartz counter tops, a large prep island,14 foot breakfast bar and newer top-of-the-line LG SS appliances, and a GE Profile cook top — ensuring that entertaining and meal prep are effortless. There is also a large dining room that can fit more than a large dinner party or family holiday gathering. Also, tucked away on the opposite side of the first floor is a guest suite, featuring a spa-inspired bath with beautiful cabinetry, exquisite tile work, and a large walk-in shower. Plus, the large laundry room with an abundance of storage and a utility sink to round out the main floor of this stunning home. Upstairs is the elegant private owner’s retreat, which also enjoys a quiet sitting area and an expansive custom walk-in closet. The spa-like bath will not disappoint with its large soaking tub, separate stall shower, and dual sinks with contemporary cabinetry and elegant tile throughout. Additional amenities include a large 2-car garage with an EV 30 amp outlet, plus an oversized over 300 square foot separate flex space that would make an excellent home office, home gym, or craft/hobby space. The home features tons of storage space, custom automated blinds with remotes, blackout blinds, a new AC unit, new lighting, new exterior paint, and a tankless water heater. This remarkable home is flooded with natural light and ambiance, with many floor-to-ceiling windows, while exuding a warm and cozy atmosphere. Zoned for some of the best public schools in the area, including Audubon K-8 and Winter Park HS, and conveniently located near Audubon Park/Corrine Drive shopping and restaurants, and of course easy access to Winter Park's Park Ave with its fine restaurants and shopping, and also close proximity to Blue Jacket Park/Baldwin Park, Downtown Orlando, Leu Gardens, the Mills 50 District and Rollins College. Don't miss your opportunity to own this exquisite Winter Park retreat, a perfect blend of luxury, privacy, and location. Florida living at its finest!

3 Beds ⋅ 4 Baths ⋅ Parklando SubDv. ⋅ 32789 Zip Code

Welcome to a truly exceptional residence nestled on a quiet, tree-lined street in one of Winter Park’s most desirable neighborhoods. This custom-built gem offers a blend of elegance, craftsmanship, and resort-style comfort, featuring 3 bedrooms, 3.5 baths, and 2,595 square feet of thoughtfully designed living space. As you enter, you'll be immediately drawn to the tranquil, resort-like ambiance created by the centerpiece of the home: a screened-in courtyard with a heated saltwater pool and spa, perfect for relaxing or entertaining year-round. Adjacent to this serene space is a private guest casita complete with a full bath and separate entrance, ideal for in-laws, visitors, or an independent-minded teen. Step into the main house, and you will be immediately captivated by the 15-foot Frank Lloyd Wright-inspired rock wall in the stunning Living Room. The 12-foot ceilings give the space a seemingly endless light and airy feel. Overlooking the great room is a fully equipped chef-inspired kitchen where creating meals will be a breeze with an abundance of cabinets, gleaming quartz counter tops, a large prep island,14 foot breakfast bar and newer top-of-the-line LG SS appliances, and a GE Profile cook top — ensuring that entertaining and meal prep are effortless. There is also a large dining room that can fit more than a large dinner party or family holiday gathering. Also, tucked away on the opposite side of the first floor is a guest suite, featuring a spa-inspired bath with beautiful cabinetry, exquisite tile work, and a large walk-in shower. Plus, the large laundry room with an abundance of storage and a utility sink to round out the main floor of this stunning home. Upstairs is the elegant private owner’s retreat, which also enjoys a quiet sitting area and an expansive custom walk-in closet. The spa-like bath will not disappoint with its large soaking tub, separate stall shower, and dual sinks with contemporary cabinetry and elegant tile throughout. Additional amenities include a large 2-car garage with an EV 30 amp outlet, plus an oversized over 300 square foot separate flex space that would make an excellent home office, home gym, or craft/hobby space. The home features tons of storage space, custom automated blinds with remotes, blackout blinds, a new AC unit, new lighting, new exterior paint, and a tankless water heater. This remarkable home is flooded with natural light and ambiance, with many floor-to-ceiling windows, while exuding a warm and cozy atmosphere. Zoned for some of the best public schools in the area, including Audubon K-8 and Winter Park HS, and conveniently located near Audubon Park/Corrine Drive shopping and restaurants, and of course easy access to Winter Park's Park Ave with its fine restaurants and shopping, and also close proximity to Blue Jacket Park/Baldwin Park, Downtown Orlando, Leu Gardens, the Mills 50 District and Rollins College. Don't miss your opportunity to own this exquisite Winter Park retreat, a perfect blend of luxury, privacy, and location. Florida living at its finest!

2728 Eastern Parkway, Winter Park

$940,000

Biscayne Bay, a recent Parade of Homes winner, is one of the latest custom builds by the trusted team at Konkol Custom Homes—and it’s ready for its very first owner. Set in a prime Winter Park location, this two-story home offers clean lines, high-end finishes, and a layout that fits real life. With just over 2,600 square feet under air, the home features 4 bedrooms and 3 full bathrooms. The 4th bedroom is located downstairs and works beautifully as a dedicated office. Upstairs, a spacious bonus room offers flexibility for a home gym, theater, large office, or guest suite. Throughout the home, you’ll find wide-plank white oak flooring, matching stair treads, tall baseboards, and cohesive, streamlined trim details. The kitchen is crisp and functional, with white cabinetry, quartz counters, tile backsplash, and well-chosen finishes. The primary suite includes a walk-in closet system and a bathroom that checks all the boxes—soaking tub, oversized shower, and double vanities. Out back, enjoy a generous covered porch, landscaping that offers privacy with a natural bamboo hedge, and a future-ready pool plan already in place. High style, low maintenance living—all just five minutes from Park Avenue, walkable to Lake Killarney, close to Dubsdread, and under 2 miles to AdventHealth. Biscayne Bay is a polished, move-in ready opportunity in the heart of Winter Park.

4 Beds ⋅ 3 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Biscayne Bay, a recent Parade of Homes winner, is one of the latest custom builds by the trusted team at Konkol Custom Homes—and it’s ready for its very first owner. Set in a prime Winter Park location, this two-story home offers clean lines, high-end finishes, and a layout that fits real life. With just over 2,600 square feet under air, the home features 4 bedrooms and 3 full bathrooms. The 4th bedroom is located downstairs and works beautifully as a dedicated office. Upstairs, a spacious bonus room offers flexibility for a home gym, theater, large office, or guest suite. Throughout the home, you’ll find wide-plank white oak flooring, matching stair treads, tall baseboards, and cohesive, streamlined trim details. The kitchen is crisp and functional, with white cabinetry, quartz counters, tile backsplash, and well-chosen finishes. The primary suite includes a walk-in closet system and a bathroom that checks all the boxes—soaking tub, oversized shower, and double vanities. Out back, enjoy a generous covered porch, landscaping that offers privacy with a natural bamboo hedge, and a future-ready pool plan already in place. High style, low maintenance living—all just five minutes from Park Avenue, walkable to Lake Killarney, close to Dubsdread, and under 2 miles to AdventHealth. Biscayne Bay is a polished, move-in ready opportunity in the heart of Winter Park.

1840 Biscayne Drive, Winter Park

$1,575,000

Beautiful Sylvan Lake Shores Mediterranean home. Ideally located in quintessential Old Winter Park with its tree lined, brick streets that surround Lake Mizell. This 4 bedroom 3 ½ bath, plus office home features timeless architectural features such as classic wide molding, repeated archways and a custom ironwork stairway. The soaring 10 foot ceilings accentuate the classic feel of this elegant home. The designer inspired kitchen features custom cabinets and spacious pantry. The spa like master suite is located on the first floor and has an en-suite bath and custom designed closet. Just recently completed, the luxurious master bath has an inviting soaking tub and separate, relaxing rain shower. The executive office is located on the first floor. Up the custom staircase are three bedrooms including a private guest room with its own en-suite bath. The open floor plan is perfect for entertaining with multiple, solid wood French doors surrounding the welcoming back yard pool with cooling fountains. Outside, a custom awning shades the patio as you relax by the pool. There is a convenient pool bath as well. This bright and sunny home is in a prime location of Winter Park with an easy walk or bike to Park Avenue with its upscale restaurants, stores and Rollins College. Excellent Winter Park Schools. This amazing move in ready home is an excellent opportunity to live in the heart of Winter Park and enjoy Central Florida living.

4 Beds ⋅ 4 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Beautiful Sylvan Lake Shores Mediterranean home. Ideally located in quintessential Old Winter Park with its tree lined, brick streets that surround Lake Mizell. This 4 bedroom 3 ½ bath, plus office home features timeless architectural features such as classic wide molding, repeated archways and a custom ironwork stairway. The soaring 10 foot ceilings accentuate the classic feel of this elegant home. The designer inspired kitchen features custom cabinets and spacious pantry. The spa like master suite is located on the first floor and has an en-suite bath and custom designed closet. Just recently completed, the luxurious master bath has an inviting soaking tub and separate, relaxing rain shower. The executive office is located on the first floor. Up the custom staircase are three bedrooms including a private guest room with its own en-suite bath. The open floor plan is perfect for entertaining with multiple, solid wood French doors surrounding the welcoming back yard pool with cooling fountains. Outside, a custom awning shades the patio as you relax by the pool. There is a convenient pool bath as well. This bright and sunny home is in a prime location of Winter Park with an easy walk or bike to Park Avenue with its upscale restaurants, stores and Rollins College. Excellent Winter Park Schools. This amazing move in ready home is an excellent opportunity to live in the heart of Winter Park and enjoy Central Florida living.

1394 Grove Terrace, Winter Park

$1,785,000

This elegant one story home is located in highly desirable Winter Park on an oversized .28 acre lot with mature and lush landscaping and NO HOA. It has 10' ceilings and an open floor plan combining kitchen, dining, and living rooms with gorgeous wood floors and plenty of natural light overlooking the secluded & screened salt water pool with cascading water features, gas heated spa, and covered lanai. This home has a warm and welcoming atmosphere perfect for entertaining family & friends. The gourmet kitchen features an induction cook top, built in convection & microwave oven, stainless steel refrigerator, vented stainless steel hood system, wine refrigerator, bar station, and pantry. It also has custom designed kitchen cabinetry with abundant storage and pull out shelving plus a big island with designer pendant lights and eat in area for a large table and chairs. The laundry room next to the master bedroom has cabinetry and a sink. Adjacent to the living room is a room that could be used as a office or workout room AND a big multi functional room with half bathroom also overlooking the pool area. Sliders from the living room and the multi functional room are pocket sliders which really open up the home in cooler weather ! The huge master suite also opens to the pool and has his and hers walk in closets with built in custom closet organizers and the master bathroom has dual sinks, whirlpool garden tub, and big walk in shower. In addition, there are two guest bedrooms that share a hall bathroom. The backyard is fenced and very private and peaceful with a gravel walkway with low voltage lighting that leads to an arbor with a swing for an outdoor gathering or reflection. Other upgrades includes Plantation shutters, motorized shades on sliding doors, whole house built in audio system, and security system. Roof was installed in 2019 and new pool pump. Steps away is Phelps Park with playground, tennis and pickleball courts and the YMCA is nearby. Park Avenue and Downtown Winter Park with plenty of fine dining and upscale shopping options are a bike ride away or short drive !

3 Beds ⋅ 3 Baths ⋅ Temple Estates SubDv. ⋅ 32789 Zip Code

This elegant one story home is located in highly desirable Winter Park on an oversized .28 acre lot with mature and lush landscaping and NO HOA. It has 10' ceilings and an open floor plan combining kitchen, dining, and living rooms with gorgeous wood floors and plenty of natural light overlooking the secluded & screened salt water pool with cascading water features, gas heated spa, and covered lanai. This home has a warm and welcoming atmosphere perfect for entertaining family & friends. The gourmet kitchen features an induction cook top, built in convection & microwave oven, stainless steel refrigerator, vented stainless steel hood system, wine refrigerator, bar station, and pantry. It also has custom designed kitchen cabinetry with abundant storage and pull out shelving plus a big island with designer pendant lights and eat in area for a large table and chairs. The laundry room next to the master bedroom has cabinetry and a sink. Adjacent to the living room is a room that could be used as a office or workout room AND a big multi functional room with half bathroom also overlooking the pool area. Sliders from the living room and the multi functional room are pocket sliders which really open up the home in cooler weather ! The huge master suite also opens to the pool and has his and hers walk in closets with built in custom closet organizers and the master bathroom has dual sinks, whirlpool garden tub, and big walk in shower. In addition, there are two guest bedrooms that share a hall bathroom. The backyard is fenced and very private and peaceful with a gravel walkway with low voltage lighting that leads to an arbor with a swing for an outdoor gathering or reflection. Other upgrades includes Plantation shutters, motorized shades on sliding doors, whole house built in audio system, and security system. Roof was installed in 2019 and new pool pump. Steps away is Phelps Park with playground, tennis and pickleball courts and the YMCA is nearby. Park Avenue and Downtown Winter Park with plenty of fine dining and upscale shopping options are a bike ride away or short drive !

1640 Mayfield Avenue, Winter Park

$439,900

One or more photo(s) has been virtually staged. ***BUY THIS HOME WITH AN FHA INTEREST RATE OF 5.375% WHEN USING THE SELLER'S PREFERRED LENDER*** You will fall in love with this mid-century Winter Park home across from Lake Bell in charming Lake Bell Terrace. This home offers 3 Bedrooms, 1 spa-like bathroom, and an en-suite half bath, a family room, living room, dining room, and a laundry room. Some of the renovations include a full kitchen redesign with fresh double-stacked white cabinetry, quartz countertops, stainless steel appliances, and sleek over-range hood. There are hardwood floors throughout the main living areas in the home & a hip hexagonal dark floor tile in the kitchen and dining room. Some of the upgrades include: a water softener system, whole house re-plumb 2021, energy efficient windows 2018/2019, A/C system (new condenser coil) A/C UV sanitation light 2019, upgraded electrical in 2023, and fresh insulation in the attic throughout the home. The spacious fenced-in backyard offers a beautiful hardscape area with a fire pit and a stunning pergola ideal for an outdoor lounge area or summer kitchen. As a bonus, the garden includes an avocado tree, ginkgo, young Anna, and pink lady apple trees, smoke bush, and lime trees. You won’t find a home better situated than this, conveniently located just one mile from I-4, this home offers easy access for your daily commute or a quick drive to catch your favorite Orlando Magic or Orlando City game. Downtown Orlando is just 12 minutes away and only 6 minutes to downtown Winter Park to enjoy all the fine dining and luxurious amenities. As for the Theme Parks, you are 35 minutes away from Disney World, Epic Universe/Universal, and less than an hour away from the nearest beach. Welcome home!

3 Beds ⋅ 2 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. ***BUY THIS HOME WITH AN FHA INTEREST RATE OF 5.375% WHEN USING THE SELLER'S PREFERRED LENDER*** You will fall in love with this mid-century Winter Park home across from Lake Bell in charming Lake Bell Terrace. This home offers 3 Bedrooms, 1 spa-like bathroom, and an en-suite half bath, a family room, living room, dining room, and a laundry room. Some of the renovations include a full kitchen redesign with fresh double-stacked white cabinetry, quartz countertops, stainless steel appliances, and sleek over-range hood. There are hardwood floors throughout the main living areas in the home & a hip hexagonal dark floor tile in the kitchen and dining room. Some of the upgrades include: a water softener system, whole house re-plumb 2021, energy efficient windows 2018/2019, A/C system (new condenser coil) A/C UV sanitation light 2019, upgraded electrical in 2023, and fresh insulation in the attic throughout the home. The spacious fenced-in backyard offers a beautiful hardscape area with a fire pit and a stunning pergola ideal for an outdoor lounge area or summer kitchen. As a bonus, the garden includes an avocado tree, ginkgo, young Anna, and pink lady apple trees, smoke bush, and lime trees. You won’t find a home better situated than this, conveniently located just one mile from I-4, this home offers easy access for your daily commute or a quick drive to catch your favorite Orlando Magic or Orlando City game. Downtown Orlando is just 12 minutes away and only 6 minutes to downtown Winter Park to enjoy all the fine dining and luxurious amenities. As for the Theme Parks, you are 35 minutes away from Disney World, Epic Universe/Universal, and less than an hour away from the nearest beach. Welcome home!

1945 Bering Avenue, Winter Park

$1,600,000

Charming Opportunity in Prime Winter Park – 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits on a double lot that is .35 acres. Only a mile stroll to the famous Park Ave shops, dining and entertaining. Home site over looks Lake Osceola and the multi million dollar homes all around!! A neighborhood lot, a few doors down, allows residents to have walking access to Lake Osceola for paddle boarding, fishing, swimming or just to enjoy the view!! This home has only had one owner and is uniquely positioned not to see a next-door neighbor to your left or right!! Embrace the mid century modern style of this home or it is priced to be a tear down to build your dream home around the other multi million dollar homes. Nestled in the heart of highly sought-after Winter Park, this spacious 4-bedroom, 2.5-bath home offers over 3,260 square feet of living space on an oversized .35 acre lot with gorgeous lake views—ideal for enjoying sunsets from a future second-story balcony or out your current kitchen window!! The 4 bedrooms are very generous in size, have ample natural light and each one has oversized closets. The bathrooms have been updated with style in mind. The luxury vinyl floors were recently installed along with new kitchen appliances. Featuring a distinctive Mansard-style roof, this residence boasts strong architectural character and a versatile layout designed for modern living. Inside, you’ll find new luxury plank flooring, large windows that invite abundant natural light, and generously sized rooms with ample closet and storage space. Home offers a lot of character and charm with the present architectural features of a Chicago brick wall, ceiling accent beams and for the art lover a huge paneled art gallery wall!! The home includes two separate living areas, a formal dining room, an eat-in kitchen, and an office area with abundant storage and desk work space —perfect for work-from-home needs, student study session or family organization. The 2-car garage adds both storage and convenience and has a large utility closet inside the garage to stay organized. While the home is ready for your personal touch, it presents a rare chance to customize and elevate a spacious property in a top-rated school district, just minutes from parks, shopping, dining, and lakefront recreation. Whether you're looking to renovate, invest, expand upward, or build your dream home — the potential here is truly exceptional.

4 Beds ⋅ 3 Baths ⋅ Osceola Summit SubDv. ⋅ 32789 Zip Code

Charming Opportunity in Prime Winter Park – 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits on a double lot that is .35 acres. Only a mile stroll to the famous Park Ave shops, dining and entertaining. Home site over looks Lake Osceola and the multi million dollar homes all around!! A neighborhood lot, a few doors down, allows residents to have walking access to Lake Osceola for paddle boarding, fishing, swimming or just to enjoy the view!! This home has only had one owner and is uniquely positioned not to see a next-door neighbor to your left or right!! Embrace the mid century modern style of this home or it is priced to be a tear down to build your dream home around the other multi million dollar homes. Nestled in the heart of highly sought-after Winter Park, this spacious 4-bedroom, 2.5-bath home offers over 3,260 square feet of living space on an oversized .35 acre lot with gorgeous lake views—ideal for enjoying sunsets from a future second-story balcony or out your current kitchen window!! The 4 bedrooms are very generous in size, have ample natural light and each one has oversized closets. The bathrooms have been updated with style in mind. The luxury vinyl floors were recently installed along with new kitchen appliances. Featuring a distinctive Mansard-style roof, this residence boasts strong architectural character and a versatile layout designed for modern living. Inside, you’ll find new luxury plank flooring, large windows that invite abundant natural light, and generously sized rooms with ample closet and storage space. Home offers a lot of character and charm with the present architectural features of a Chicago brick wall, ceiling accent beams and for the art lover a huge paneled art gallery wall!! The home includes two separate living areas, a formal dining room, an eat-in kitchen, and an office area with abundant storage and desk work space —perfect for work-from-home needs, student study session or family organization. The 2-car garage adds both storage and convenience and has a large utility closet inside the garage to stay organized. While the home is ready for your personal touch, it presents a rare chance to customize and elevate a spacious property in a top-rated school district, just minutes from parks, shopping, dining, and lakefront recreation. Whether you're looking to renovate, invest, expand upward, or build your dream home — the potential here is truly exceptional.

446 Alberta Drive, Winter Park

$2,288,215

A Jewel Box: Curated for a Life Well Lived. Penthouse 404 at The Alabama is a rare architectural gem—a two-story residence that blends historic provenance w/ design-forward luxury in the heart of Winter Park’s most coveted lakefront setting. Created by combining two original top-floor units, this expansive penthouse is the largest in the building & the only one w/ a private outdoor terrace. Originally constructed in 1921 as the Alabama Hotel, the Mediterranean Revival structure has been transformed into an intimate community of 19 private residences overlooking Lake Maitland w/ direct access to the Winter Park Chain of Lakes. Reimagined by Z Properties in 2019 w/ a full renovation, the home reflects thoughtful scale, bespoke craftsmanship & a sophisticated design vision. The dramatic entry foyer features extensive millwork paneling that conceals the bedroom suites & opens into a light-filled great room w/ expansive lake-facing windows & French doors that open to the signature terrace: a professionally landscaped outdoor retreat w/ turf grass, mist fans, lighting, irrigation & custom planters. At the heart of the home, the boldly composed kitchen balances sculptural form & high function. A sculptural block of black quartz anchors the island w/ seating, trimmed in gold metal cladding that echoes the gold countertops & full-height backsplash. Sleek, dark wood, high-gloss cabinetry conceals a panel-ready Thermador suite, including double refrigerator columns & dishwasher. Lacquered finishes, under-cabinet lighting, geometric black-&-white tile, designer fixtures, brass Lutron controls, linear HVAC diffusers, LED recessed lighting & in-ceiling Sonos speakers complete the experience. What appears to be cabinetry is actually a hidden door leading to a den/family room at the rear of the home—overlooking the lake & appointed w/ custom built-ins, black sisal carpet & a moody grasscloth ceiling that mirrors the wall color & adds cinematic ambiance. Throughout, curated materials elevate each room: Venetian plaster, Schumacher wallpaper, signature lighting, oak chevron-patterned hardwood floors & tailored sisal carpets. The main level includes two en-suite bedrooms located just off the foyer. The primary suite offers a lacquered accent wall, boutique-style closets & a spa-quality bath w/ a custom vanity, dual undermount sinks, lucite-&-metal hardware, black quartz counters & full-height mirrors w/ integrated lighting. A glass-enclosed wet room w/ soaking tub & rain shower, Toto toilet & Venetian plaster walls completes the suite. A discreet laundry room & storage area are tucked away nearby. The secondary bedroom features a black vanity w/ gold hardware, black-&-white subway tile, gold sunburst mirror & a walk-in frameless glass shower—ideal for guests or extended stays. Upstairs, a third en-suite bedroom offers treetop & lake views, a mirrored gym wall & private bath featuring a black vanity w/ silver-toned hardware, black quartz top, black penny tile floors & bold geometric tile that spans the shower & vanity wall—complete w/ a tucked-away water closet for added privacy. Additional features include Nest-controlled dual HVAC, 80-gallon stainless water heater w/ booster, Everpure filtration, Jeld-Wen impact-rated windows & doors, Lutron controls & two reserved covered parking spaces. The Alabama offers a lakeside pool, renovated clubhouse, private dock & community boat slips—all just minutes from Park Avenue.

3 Beds ⋅ 4 Baths ⋅ Alabama Condo SubDv. ⋅ 32789 Zip Code

A Jewel Box: Curated for a Life Well Lived. Penthouse 404 at The Alabama is a rare architectural gem—a two-story residence that blends historic provenance w/ design-forward luxury in the heart of Winter Park’s most coveted lakefront setting. Created by combining two original top-floor units, this expansive penthouse is the largest in the building & the only one w/ a private outdoor terrace. Originally constructed in 1921 as the Alabama Hotel, the Mediterranean Revival structure has been transformed into an intimate community of 19 private residences overlooking Lake Maitland w/ direct access to the Winter Park Chain of Lakes. Reimagined by Z Properties in 2019 w/ a full renovation, the home reflects thoughtful scale, bespoke craftsmanship & a sophisticated design vision. The dramatic entry foyer features extensive millwork paneling that conceals the bedroom suites & opens into a light-filled great room w/ expansive lake-facing windows & French doors that open to the signature terrace: a professionally landscaped outdoor retreat w/ turf grass, mist fans, lighting, irrigation & custom planters. At the heart of the home, the boldly composed kitchen balances sculptural form & high function. A sculptural block of black quartz anchors the island w/ seating, trimmed in gold metal cladding that echoes the gold countertops & full-height backsplash. Sleek, dark wood, high-gloss cabinetry conceals a panel-ready Thermador suite, including double refrigerator columns & dishwasher. Lacquered finishes, under-cabinet lighting, geometric black-&-white tile, designer fixtures, brass Lutron controls, linear HVAC diffusers, LED recessed lighting & in-ceiling Sonos speakers complete the experience. What appears to be cabinetry is actually a hidden door leading to a den/family room at the rear of the home—overlooking the lake & appointed w/ custom built-ins, black sisal carpet & a moody grasscloth ceiling that mirrors the wall color & adds cinematic ambiance. Throughout, curated materials elevate each room: Venetian plaster, Schumacher wallpaper, signature lighting, oak chevron-patterned hardwood floors & tailored sisal carpets. The main level includes two en-suite bedrooms located just off the foyer. The primary suite offers a lacquered accent wall, boutique-style closets & a spa-quality bath w/ a custom vanity, dual undermount sinks, lucite-&-metal hardware, black quartz counters & full-height mirrors w/ integrated lighting. A glass-enclosed wet room w/ soaking tub & rain shower, Toto toilet & Venetian plaster walls completes the suite. A discreet laundry room & storage area are tucked away nearby. The secondary bedroom features a black vanity w/ gold hardware, black-&-white subway tile, gold sunburst mirror & a walk-in frameless glass shower—ideal for guests or extended stays. Upstairs, a third en-suite bedroom offers treetop & lake views, a mirrored gym wall & private bath featuring a black vanity w/ silver-toned hardware, black quartz top, black penny tile floors & bold geometric tile that spans the shower & vanity wall—complete w/ a tucked-away water closet for added privacy. Additional features include Nest-controlled dual HVAC, 80-gallon stainless water heater w/ booster, Everpure filtration, Jeld-Wen impact-rated windows & doors, Lutron controls & two reserved covered parking spaces. The Alabama offers a lakeside pool, renovated clubhouse, private dock & community boat slips—all just minutes from Park Avenue.

1602 Alabama Drive Unit PH404, Winter Park

$850,000

Seller may consider buyer concessions if made in an offer | Lakefront charm meets quiet luxury in the heart of Winter Park! This beautifully updated single story POOL HOME sits on nearly HALF AN ACRE of LAKEFRONT PROPERTY on the coveted LAKE BELL - a private SKI LAKE - offering a private dock/boat lift, character and contemporary upgrades that make everyday feel like a lakeside retreat. Major updates include a NEW ROOF (2022), A/C (2022), TILE FLOORING THROUGHOUT (2023), a COMPLETE KITCHEN RENOVATION (2023), and a FULLY REMODELED PRIMARY BATH (2023). Enjoy peace of mind with double pane windows, fresh interior and exterior paint (2022), and a septic system service also (2022). The home also features NEWER WINDOW TREATMENTS (2022), a new pool pump (2023), and NEW DOCK DECKING (2024)! Inside you will be pleased to find vaulted ceilings, an abundance of NATURAL LIGHT, and a light, bright OPEN FLOOR PLAN that flows seamlessly between formal and family spaces. From the moment you enter you are greeted with UNINTERRUPTED LAKE VIEWS, setting the tone for a home designed around its beautiful surroundings. The layout includes a spacious FLORIDA ROOM overlooking the pool and lake beyond – perfect for year round enjoyment! Step outside to your private outdoor oasis featuring an open-air pool with waterfall feature, patio, lush landscaping and a fun in the sun SAND BEACH leading to your private dock. Sunset views over the water are a daily luxury! Located in one of Winter Park’s most desired neighborhoods, you are only minutes away from top-tier dining, boutique shopping, parks, and major roadways like US 17/92, Orlando Ave and I-4. With its blend of charm, modern updates, and an unbeatable lakefront setting, this home truly is a rare GEM. Call today to schedule your tour and start living the LAKE LIFE – where every day feels like a vacation!

3 Beds ⋅ 2 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code

Seller may consider buyer concessions if made in an offer | Lakefront charm meets quiet luxury in the heart of Winter Park! This beautifully updated single story POOL HOME sits on nearly HALF AN ACRE of LAKEFRONT PROPERTY on the coveted LAKE BELL - a private SKI LAKE - offering a private dock/boat lift, character and contemporary upgrades that make everyday feel like a lakeside retreat. Major updates include a NEW ROOF (2022), A/C (2022), TILE FLOORING THROUGHOUT (2023), a COMPLETE KITCHEN RENOVATION (2023), and a FULLY REMODELED PRIMARY BATH (2023). Enjoy peace of mind with double pane windows, fresh interior and exterior paint (2022), and a septic system service also (2022). The home also features NEWER WINDOW TREATMENTS (2022), a new pool pump (2023), and NEW DOCK DECKING (2024)! Inside you will be pleased to find vaulted ceilings, an abundance of NATURAL LIGHT, and a light, bright OPEN FLOOR PLAN that flows seamlessly between formal and family spaces. From the moment you enter you are greeted with UNINTERRUPTED LAKE VIEWS, setting the tone for a home designed around its beautiful surroundings. The layout includes a spacious FLORIDA ROOM overlooking the pool and lake beyond – perfect for year round enjoyment! Step outside to your private outdoor oasis featuring an open-air pool with waterfall feature, patio, lush landscaping and a fun in the sun SAND BEACH leading to your private dock. Sunset views over the water are a daily luxury! Located in one of Winter Park’s most desired neighborhoods, you are only minutes away from top-tier dining, boutique shopping, parks, and major roadways like US 17/92, Orlando Ave and I-4. With its blend of charm, modern updates, and an unbeatable lakefront setting, this home truly is a rare GEM. Call today to schedule your tour and start living the LAKE LIFE – where every day feels like a vacation!

1018 Turner Road, Winter Park

$1,000,000

Welcome to 2607 Lafayette Avenue – a stunning custom-built residence nestled in one of Winter Park’s most desirable neighborhoods. This beautifully crafted home offers 4 spacious bedrooms, 3.5 bathrooms, and 2,770 square feet of refined living space designed for modern comfort and effortless entertaining. Step inside to discover an open-concept layout that seamlessly connects the kitchen, dining, and living areas. The kitchen features brand-new appliances, quartz countertops, shaker-style cabinetry, a classic subway tile backsplash, and a large island ideal for gathering. Elegant new light fixtures and a built-in wet bar elevate the space with a touch of sophistication. The first-floor primary suite is a serene retreat, offering two closets and a well-appointed en-suite bathroom complete with a soaking tub and separate walk-in shower. Upstairs, a spacious loft opens to a walk-out balcony and is accompanied by three additional bedrooms and two full bathrooms – perfect for family and guests. Storage is abundant with three walk-in closets, a double closet, and a convenient under-stair space. Additional highlights include a two-car garage with an epoxy floor, a screened patio for year-round enjoyment, and a fenced backyard oasis ideal for relaxation or entertaining. Freshly painted and surrounded by all-new professional landscaping with an irrigation system, this home offers exceptional curb appeal. Located just minutes from Park Avenue’s shopping and dining, Rollins College, the Winter Park Chain of Lakes, and zoned for A-rated Dommerich Elementary, Maitland Middle, and Winter Park High School—this property blends luxury, location, and lifestyle.

4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

Welcome to 2607 Lafayette Avenue – a stunning custom-built residence nestled in one of Winter Park’s most desirable neighborhoods. This beautifully crafted home offers 4 spacious bedrooms, 3.5 bathrooms, and 2,770 square feet of refined living space designed for modern comfort and effortless entertaining. Step inside to discover an open-concept layout that seamlessly connects the kitchen, dining, and living areas. The kitchen features brand-new appliances, quartz countertops, shaker-style cabinetry, a classic subway tile backsplash, and a large island ideal for gathering. Elegant new light fixtures and a built-in wet bar elevate the space with a touch of sophistication. The first-floor primary suite is a serene retreat, offering two closets and a well-appointed en-suite bathroom complete with a soaking tub and separate walk-in shower. Upstairs, a spacious loft opens to a walk-out balcony and is accompanied by three additional bedrooms and two full bathrooms – perfect for family and guests. Storage is abundant with three walk-in closets, a double closet, and a convenient under-stair space. Additional highlights include a two-car garage with an epoxy floor, a screened patio for year-round enjoyment, and a fenced backyard oasis ideal for relaxation or entertaining. Freshly painted and surrounded by all-new professional landscaping with an irrigation system, this home offers exceptional curb appeal. Located just minutes from Park Avenue’s shopping and dining, Rollins College, the Winter Park Chain of Lakes, and zoned for A-rated Dommerich Elementary, Maitland Middle, and Winter Park High School—this property blends luxury, location, and lifestyle.

2607 Lafayette Avenue, Winter Park

$1,300,000

**DON'T LET THIS OPPORTUNITY PASS YOU BY, BACK ON MARKET DUE TO BUYERS FINANCING.** Luxurious Retreat in the Heart of Winter Park’s Premier Neighborhood – Minutes from Park Ave! Discover timeless elegance in this stunning 4-bedroom, 3.5-bathroom home offering 2,953 square feet of thoughtfully designed living space. Nestled on tree-lined streets in one of Winter Park’s most coveted areas, surrounded by multi-million-dollar estates and just moments from the Winter Park Chain of Lakes, this home defines luxury living. Step through the impressive cut beveled glass double front doors into an interior filled with natural light, featuring hardwood floors, crown molding, recessed lighting, and blinds and Roman shades throughout. Formal living and dining rooms provide an elegant backdrop for entertaining, while the fireplace in the family room adds a cozy touch. Sliding French doors and two sets of large sliders seamlessly extend the living space to the private pool area. A sunroom (added in 2024) with a mini split system offers additional space to relax and unwind. Enjoy modern upgrades including a monitored security system, intercom system, reverse osmosis water filtration, and a water softener system. The gourmet kitchen is a chef’s dream with custom wood cabinetry, wavy tiled backsplash, granite countertops, stainless appliances including a newer refrigerator (2024) and newer dishwasher (2022), a gas stove, and two pantries, including a walk-in pantry. The breakfast nook and breakfast bar with seating for three creates plenty of space for gathering. Retreat to the luxurious primary suite with wood floors, a large walk-in closet, and a spa-like ensuite bathroom featuring double split vanities, a garden soaking tub, a large tiled shower, and a private water closet. Enjoy your own private backyard paradise on a .26-acre lot with a resort-style in-ground pool (2021), waterfall feature, sun shelf, lush landscaping, and irrigation system. An electronic front gate provides peace of mind for security as you're guided to a paved driveway and parking pad with a 2-car garage to complete this exceptional property. All this in a highly sought-after location, just minutes from Park Avenue’s high end shops and fine dining restaurants, Rollins College/Dinky Dock public boat ramp, Winter Park 9 Golf Club, Winter Park Racquet Club, Interlachen Country Club, Winter Park YMCA and WP Phelps Park and playground and so much more! Don’t miss your chance to own a piece of Winter Park’s finest! Schedule your private tour today. (Roof: 2019, HVAC 2017, Mini Splits (2) 2024, Electrical 2004, Plumbing 2004)

4 Beds ⋅ 4 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

**DON'T LET THIS OPPORTUNITY PASS YOU BY, BACK ON MARKET DUE TO BUYERS FINANCING.** Luxurious Retreat in the Heart of Winter Park’s Premier Neighborhood – Minutes from Park Ave! Discover timeless elegance in this stunning 4-bedroom, 3.5-bathroom home offering 2,953 square feet of thoughtfully designed living space. Nestled on tree-lined streets in one of Winter Park’s most coveted areas, surrounded by multi-million-dollar estates and just moments from the Winter Park Chain of Lakes, this home defines luxury living. Step through the impressive cut beveled glass double front doors into an interior filled with natural light, featuring hardwood floors, crown molding, recessed lighting, and blinds and Roman shades throughout. Formal living and dining rooms provide an elegant backdrop for entertaining, while the fireplace in the family room adds a cozy touch. Sliding French doors and two sets of large sliders seamlessly extend the living space to the private pool area. A sunroom (added in 2024) with a mini split system offers additional space to relax and unwind. Enjoy modern upgrades including a monitored security system, intercom system, reverse osmosis water filtration, and a water softener system. The gourmet kitchen is a chef’s dream with custom wood cabinetry, wavy tiled backsplash, granite countertops, stainless appliances including a newer refrigerator (2024) and newer dishwasher (2022), a gas stove, and two pantries, including a walk-in pantry. The breakfast nook and breakfast bar with seating for three creates plenty of space for gathering. Retreat to the luxurious primary suite with wood floors, a large walk-in closet, and a spa-like ensuite bathroom featuring double split vanities, a garden soaking tub, a large tiled shower, and a private water closet. Enjoy your own private backyard paradise on a .26-acre lot with a resort-style in-ground pool (2021), waterfall feature, sun shelf, lush landscaping, and irrigation system. An electronic front gate provides peace of mind for security as you're guided to a paved driveway and parking pad with a 2-car garage to complete this exceptional property. All this in a highly sought-after location, just minutes from Park Avenue’s high end shops and fine dining restaurants, Rollins College/Dinky Dock public boat ramp, Winter Park 9 Golf Club, Winter Park Racquet Club, Interlachen Country Club, Winter Park YMCA and WP Phelps Park and playground and so much more! Don’t miss your chance to own a piece of Winter Park’s finest! Schedule your private tour today. (Roof: 2019, HVAC 2017, Mini Splits (2) 2024, Electrical 2004, Plumbing 2004)

1420 Palmer Avenue, Winter Park

$1,400,000

This 5 bedroom, 4 full bathroom one story refreshed ranch estate boasts nearly 4,200 sq ft and features 3 fireplaces, double primary suites, and sprawls out on an oversized .36 acre lot, overlooking an open air salt water & solar heated pool. Updates & upgrades include: full roof replacement with transferable warranty (2023), new windows with transferable warranty (2023), 4 newer ACs (2 are 2023 & 2 are 2017), pool resurfaced with new waterline tiles and stacked stone (2023), pool salt cell replaced with 3 year warranty (2025), new carpet in bedrooms (2025), fresh sod in the backyard (2025), new turf in atrium (2025), exterior paint (2023), plantation shutters throughout, tile floors (2016), closets by design. The kitchen has undergone a full remodel & is the heart of the home. It features quartz countertops, a 10' quartz peninsula, a Bosch cooktop, Bosch oven with a top built-in microwave, a GE cafe smudge proof fridge and a farmers sink. The kitchen opens up to the family room, with a stacked stone feature wall and built-in shelving, all surrounding the cozy wood burning fireplace. The primary bedroom is split on one side of the home, offering privacy, is oversized and features a seating area with it's own wood burning fireplace. The ensuite primary bathroom has been remodeled with dual sinks, a deep soaking tub and a separate shower stall with floor to ceiling tile & glass frame. The second primary bedroom, which would function perfectly as an in-law or nanny suite, is split on the other side of the home and features it's own AC & water heater, with an ensuite bathroom. The additional 3 bedrooms can also be found on this side of the home, 2 of which share a jack n jill bathroom, and the final & 5th bedroom, measuring 25X12, has enough room for double office spaces or could be utilized as an office & work out space. While the home features a formal living, formal dining, family room & dining nook, there is also a secondary living space, off the secondary primary suite, complete with a wet bar, wine chiller and an electric fireplace. It's the perfect flex room and could serve as a separate in-law living area or a game room. The pool is a show stopper and has been resurfaced, including the install of new waterline tiles and stacked stone. With a sun shelf & bubbler, this pool offers resort style relaxation and is surrounded by a resealed paver deck. The side yard is ample space to play and has been freshly sodded. Zoned Winter Park High, Glenridge Middle & Brookshire Elementary, and just minutes from Advent Health Winter Park Hospital, the East End Market, which serves as a hub of market & culinary delights, and less than 4 miles from the popular Park Avenue, where you can enjoy acclaimed eateries and some of Orlando's best shopping, the location is highly desirable. Move right in, everything has been done.

5 Beds ⋅ 4 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code

This 5 bedroom, 4 full bathroom one story refreshed ranch estate boasts nearly 4,200 sq ft and features 3 fireplaces, double primary suites, and sprawls out on an oversized .36 acre lot, overlooking an open air salt water & solar heated pool. Updates & upgrades include: full roof replacement with transferable warranty (2023), new windows with transferable warranty (2023), 4 newer ACs (2 are 2023 & 2 are 2017), pool resurfaced with new waterline tiles and stacked stone (2023), pool salt cell replaced with 3 year warranty (2025), new carpet in bedrooms (2025), fresh sod in the backyard (2025), new turf in atrium (2025), exterior paint (2023), plantation shutters throughout, tile floors (2016), closets by design. The kitchen has undergone a full remodel & is the heart of the home. It features quartz countertops, a 10' quartz peninsula, a Bosch cooktop, Bosch oven with a top built-in microwave, a GE cafe smudge proof fridge and a farmers sink. The kitchen opens up to the family room, with a stacked stone feature wall and built-in shelving, all surrounding the cozy wood burning fireplace. The primary bedroom is split on one side of the home, offering privacy, is oversized and features a seating area with it's own wood burning fireplace. The ensuite primary bathroom has been remodeled with dual sinks, a deep soaking tub and a separate shower stall with floor to ceiling tile & glass frame. The second primary bedroom, which would function perfectly as an in-law or nanny suite, is split on the other side of the home and features it's own AC & water heater, with an ensuite bathroom. The additional 3 bedrooms can also be found on this side of the home, 2 of which share a jack n jill bathroom, and the final & 5th bedroom, measuring 25X12, has enough room for double office spaces or could be utilized as an office & work out space. While the home features a formal living, formal dining, family room & dining nook, there is also a secondary living space, off the secondary primary suite, complete with a wet bar, wine chiller and an electric fireplace. It's the perfect flex room and could serve as a separate in-law living area or a game room. The pool is a show stopper and has been resurfaced, including the install of new waterline tiles and stacked stone. With a sun shelf & bubbler, this pool offers resort style relaxation and is surrounded by a resealed paver deck. The side yard is ample space to play and has been freshly sodded. Zoned Winter Park High, Glenridge Middle & Brookshire Elementary, and just minutes from Advent Health Winter Park Hospital, the East End Market, which serves as a hub of market & culinary delights, and less than 4 miles from the popular Park Avenue, where you can enjoy acclaimed eateries and some of Orlando's best shopping, the location is highly desirable. Move right in, everything has been done.

1327 Bridgeport Drive, Winter Park

$4,750,000

Welcome home to a gated estate on one of the most desired streets in Winter Park, on a half-acre with a separate guesthouse & walk in wine cellar and tasting room, & a short distance to Park Avenue, Kraft Azalea Gardens and Winter Park Racquet Club. Timeless elegance and flawless artistry blend perfectly with modern comfort and function in this one-of-a-kind custom home originally designed for the Mayor of Winter Park in the 1920s. Designed by Slocum Platts Architects, renovated by Clayton Homes and recently modernized and maintained by E2 Homes, this residence has been immaculately cared for and appointed for the most discerning buyer.

4 Beds ⋅ 6 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Welcome home to a gated estate on one of the most desired streets in Winter Park, on a half-acre with a separate guesthouse & walk in wine cellar and tasting room, & a short distance to Park Avenue, Kraft Azalea Gardens and Winter Park Racquet Club. Timeless elegance and flawless artistry blend perfectly with modern comfort and function in this one-of-a-kind custom home originally designed for the Mayor of Winter Park in the 1920s. Designed by Slocum Platts Architects, renovated by Clayton Homes and recently modernized and maintained by E2 Homes, this residence has been immaculately cared for and appointed for the most discerning buyer.

984 Mayfield Avenue, Winter Park

$1,825,000

One or more photo(s) has been virtually staged. Welcome to 1361 Palmer Avenue, a beautifully updated five-bedroom, 3.5-bath residence in the heart of Winter Park, Florida, 32789. This exceptional home has been meticulously maintained and extensively renovated, blending classic charm with modern design. Inside, you'll find a reimagined designer kitchen with premium finishes, ideal for everyday living and entertaining, as well as an elegant home office with timeless wood paneling. The spacious interior features custom woodwork, generous living areas with abundant natural light, and sweeping views of the pool that create a seamless connection between indoor and outdoor living. The first-floor primary suite is a private retreat, complete with a luxurious en-suite bath offering dual vanities, a spa-like shower and two custom walk-in closets. French doors open to a serene backyard oasis, where a resurfaced, oversized pool and spa await, alongside a fully equipped summer kitchen, cozy firepit, and a pergola ideal for outdoor dining and relaxation. Upstairs, four additional bedrooms and two remodeled full baths provide ample space for family and guests. This home offers numerous high-end upgrades, including new air-conditioning units, a tankless water heater, energy-efficient PGT doors, improved insulation, lush landscaping with outdoor lighting and a whole-home water softener system—providing comfort, style and lasting peace of mind. Ideally in the Winter Park school district and just minutes from Phelps Park, Park Avenue, Interlachen Country Club, Winter Park Racquet Club and Rollins College, this home presents an unparalleled opportunity to enjoy refined living in one of Central Florida’s desirable communities.

5 Beds ⋅ 4 Baths ⋅ Temple Heights SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Welcome to 1361 Palmer Avenue, a beautifully updated five-bedroom, 3.5-bath residence in the heart of Winter Park, Florida, 32789. This exceptional home has been meticulously maintained and extensively renovated, blending classic charm with modern design. Inside, you'll find a reimagined designer kitchen with premium finishes, ideal for everyday living and entertaining, as well as an elegant home office with timeless wood paneling. The spacious interior features custom woodwork, generous living areas with abundant natural light, and sweeping views of the pool that create a seamless connection between indoor and outdoor living. The first-floor primary suite is a private retreat, complete with a luxurious en-suite bath offering dual vanities, a spa-like shower and two custom walk-in closets. French doors open to a serene backyard oasis, where a resurfaced, oversized pool and spa await, alongside a fully equipped summer kitchen, cozy firepit, and a pergola ideal for outdoor dining and relaxation. Upstairs, four additional bedrooms and two remodeled full baths provide ample space for family and guests. This home offers numerous high-end upgrades, including new air-conditioning units, a tankless water heater, energy-efficient PGT doors, improved insulation, lush landscaping with outdoor lighting and a whole-home water softener system—providing comfort, style and lasting peace of mind. Ideally in the Winter Park school district and just minutes from Phelps Park, Park Avenue, Interlachen Country Club, Winter Park Racquet Club and Rollins College, this home presents an unparalleled opportunity to enjoy refined living in one of Central Florida’s desirable communities.

1361 Palmer Ave., Winter Park

$1,480,000

OPPORTUNITY AWAITS – PURE POTENTIAL IN WINTER PARK’S SEVILLA NEIGHBORHOOD! Rare, Tudor-style estate sits on an oversized 0.44 acre lot (19,217 SF) at the end of a quiet cul-de-sac and offers elevated views of Lake Sue. Originally built in the 1970’s, this well-built, concrete block home, offers a very spacious interior layout with 5-bedrooms, 5 full baths, 2 half baths, formal living & dining rooms, a family room, and a large kitchen. Dramatic, exposed wood-beam, cathedral ceilings can be found in many of the rooms creating open and airy spaces. Architectural features such as Gothic arches, solid wood doors, craftsman window trim and framing, terracotta tile floors, two stone fireplaces, and an “old world” bar are just a few of the handcrafted details that have been installed throughout. This 2-story home offers a very functional floor plan. On the first floor you’ll find the kitchen, living, dining, and family rooms, a half bath, and two primary bedrooms, each with a full en suite. Upstairs are 3 generously sized bedrooms, two of which share a Jack-and-Jill bath, and the third which has “his and her bathrooms” as well as access to the upstairs bonus room. Outdoors there is no shortage of entertainment space. The home wraps around a large, courtyard-inspired pool, and is surrounded by well-landscaped gardens which create the perfect amount of privacy. Stroll the beautiful garden path and enjoy sweeping views of Lake Sue. Continue up the pathway to find a finished FDU (approximately 500 SF not included in home’s total SF) with a kitchenette and full bath. Located in one of Winter Park’s most desirable neighborhoods, residents of Sevilla enjoy the charm of this sidewalk neighborhood and its convenience to nearby Park Avenue with its many shops and restaurants. Its homes are also zoned for the coveted Audubon K-8 school district and top private schools are just a 10-minute drive away. This one-of-a-kind estate home is truly special and a must-see.

5 Beds ⋅ 8 Baths ⋅ Sevilla SubDv. ⋅ 32789 Zip Code

OPPORTUNITY AWAITS – PURE POTENTIAL IN WINTER PARK’S SEVILLA NEIGHBORHOOD! Rare, Tudor-style estate sits on an oversized 0.44 acre lot (19,217 SF) at the end of a quiet cul-de-sac and offers elevated views of Lake Sue. Originally built in the 1970’s, this well-built, concrete block home, offers a very spacious interior layout with 5-bedrooms, 5 full baths, 2 half baths, formal living & dining rooms, a family room, and a large kitchen. Dramatic, exposed wood-beam, cathedral ceilings can be found in many of the rooms creating open and airy spaces. Architectural features such as Gothic arches, solid wood doors, craftsman window trim and framing, terracotta tile floors, two stone fireplaces, and an “old world” bar are just a few of the handcrafted details that have been installed throughout. This 2-story home offers a very functional floor plan. On the first floor you’ll find the kitchen, living, dining, and family rooms, a half bath, and two primary bedrooms, each with a full en suite. Upstairs are 3 generously sized bedrooms, two of which share a Jack-and-Jill bath, and the third which has “his and her bathrooms” as well as access to the upstairs bonus room. Outdoors there is no shortage of entertainment space. The home wraps around a large, courtyard-inspired pool, and is surrounded by well-landscaped gardens which create the perfect amount of privacy. Stroll the beautiful garden path and enjoy sweeping views of Lake Sue. Continue up the pathway to find a finished FDU (approximately 500 SF not included in home’s total SF) with a kitchenette and full bath. Located in one of Winter Park’s most desirable neighborhoods, residents of Sevilla enjoy the charm of this sidewalk neighborhood and its convenience to nearby Park Avenue with its many shops and restaurants. Its homes are also zoned for the coveted Audubon K-8 school district and top private schools are just a 10-minute drive away. This one-of-a-kind estate home is truly special and a must-see.

1742 Barcelona Way, Winter Park

$3,200,000

**This stunning estate just became an unbeatable opportunity--luxury living at a dramatically reduced price! Don't miss your chance to own this exceptional home in the highly coveted Windsong community with access to the gorgeous Winter Park chain of lakes. Prepare to be impressed as you enter this almost 6,000 square foot home adorned with custom high-end features throughout, plus a fabulous guest apartment with a full bathroom and kitchenette fully renovated to be enjoyed as a private poker/bourbon room. This exceptional residence has been converted to a full Smart Home with integrated controls for lighting, audio/video, security system with cameras, intercom, thermostat and sun shade. The beautiful chef's kitchen boasts a brand new 48” Sub-Zero refrigerator, and all new Wolf appliances including double 30” electric ovens, microwave, gas cooktop, hood insert, and warming drawer. For added convenience, a fully appointed Butler's pantry is adjacent to the kitchen. Retreat to the stunning first floor owner's suite featuring a newly installed electric fireplace, sitting area, a walk-in closet with custom cabinetry, a separate office/home gym and a spa-inspired bathroom with a jetted tub and steam shower. Just outside, step into your own personal wellness retreat with a new Polar Monkey brand cold plunge and a four-person sauna. Also, guests will enjoy the convenience of another private first floor bedroom suite. Upstairs are the additional three spacious bedrooms and bathrooms, a huge loft area, and hidden stairs leading to a generous air conditioned storage room, great for a home theater. The outside oasis greets you with a fully reimagined expansive covered lanai with an outdoor kitchen complete with a 60" Fire Magic grill, 60" Fire Magic vent hood, Summit refrigerator, and stainless steel cabinets. Relax by the sparkling saltwater pool with its sun shelf, retractable screen, and travertine deck surrounded by lush tropical landscaping and artificial turf for carefree living. The extensive renovations to this luxury estate continue with the installation of a new roof, new gutters with leaf guards, freshly painted exterior, new wood trellis, all new saltwater pool equipment, and epoxy garage flooring with added custom cabinets. Embrace this luxury lifestyle with exclusive access to the Windsong Residence Club overlooking the Winter Park Chain of Lakes, with amenities including lake access, community pools, splash park, playground, and use of the pontoon boat. This home may be purchased fully furnished. Don't miss the opportunity to own this spectacular home in one of Winter Park's most sought after neighborhoods with its top-rated schools, and proximity to shopping and dining on Park Avenue in picturesque downtown Winter Park!

6 Beds ⋅ 6 Baths ⋅ Windsong Lakeside Sec 01 43/70 SubDv. ⋅ 32789 Zip Code

**This stunning estate just became an unbeatable opportunity--luxury living at a dramatically reduced price! Don't miss your chance to own this exceptional home in the highly coveted Windsong community with access to the gorgeous Winter Park chain of lakes. Prepare to be impressed as you enter this almost 6,000 square foot home adorned with custom high-end features throughout, plus a fabulous guest apartment with a full bathroom and kitchenette fully renovated to be enjoyed as a private poker/bourbon room. This exceptional residence has been converted to a full Smart Home with integrated controls for lighting, audio/video, security system with cameras, intercom, thermostat and sun shade. The beautiful chef's kitchen boasts a brand new 48” Sub-Zero refrigerator, and all new Wolf appliances including double 30” electric ovens, microwave, gas cooktop, hood insert, and warming drawer. For added convenience, a fully appointed Butler's pantry is adjacent to the kitchen. Retreat to the stunning first floor owner's suite featuring a newly installed electric fireplace, sitting area, a walk-in closet with custom cabinetry, a separate office/home gym and a spa-inspired bathroom with a jetted tub and steam shower. Just outside, step into your own personal wellness retreat with a new Polar Monkey brand cold plunge and a four-person sauna. Also, guests will enjoy the convenience of another private first floor bedroom suite. Upstairs are the additional three spacious bedrooms and bathrooms, a huge loft area, and hidden stairs leading to a generous air conditioned storage room, great for a home theater. The outside oasis greets you with a fully reimagined expansive covered lanai with an outdoor kitchen complete with a 60" Fire Magic grill, 60" Fire Magic vent hood, Summit refrigerator, and stainless steel cabinets. Relax by the sparkling saltwater pool with its sun shelf, retractable screen, and travertine deck surrounded by lush tropical landscaping and artificial turf for carefree living. The extensive renovations to this luxury estate continue with the installation of a new roof, new gutters with leaf guards, freshly painted exterior, new wood trellis, all new saltwater pool equipment, and epoxy garage flooring with added custom cabinets. Embrace this luxury lifestyle with exclusive access to the Windsong Residence Club overlooking the Winter Park Chain of Lakes, with amenities including lake access, community pools, splash park, playground, and use of the pontoon boat. This home may be purchased fully furnished. Don't miss the opportunity to own this spectacular home in one of Winter Park's most sought after neighborhoods with its top-rated schools, and proximity to shopping and dining on Park Avenue in picturesque downtown Winter Park!

141 S Phelps Avenue, Winter Park

$2,550,000

1440 Place Picardy, Winter Park, FL Custom-Built Elegance with Timeless Finishes A custom-built residence completed in 2008 that blends classic craftsmanship with luxurious, modern living. From the moment you step inside, the superior millwork, solid hardwood floors, and elegant design details make a lasting impression. The gourmet kitchen is a chef’s dream, featuring marble countertops, an oversized gas range, and premium DCS and Sub-Zero appliances. It opens seamlessly to a warm and inviting living area, complete with custom built-ins and a cozy gas fireplace—perfect for entertaining or quiet evenings at home. The spacious primary suite is located on the main floor and boasts generous walk-in closets and a versatile adjoining room, ideal for a home office, nursery, or private retreat. Upstairs, you'll find three expansive bedrooms, three full bathrooms, and a versatile bonus room—perfect for guests, hobbies, or a playroom. Lovingly maintained, this home received a new roof in 2021 and features high-quality windows and doors throughout, bathing every room in natural light. No detail was overlooked. Step outside to your private, beautifully landscaped backyard, which includes a second gas fireplace and a detached flex room—currently used as a gym, but easily converted into a private office or studio space. The oversized three-car side-entry garage offers abundant storage and includes a Tesla charger—ideal for electric vehicle owners. Nestled on a peaceful street, this home is just minutes from everything Winter Park has to offer and is located within the highly sought-after Dommerich, Maitland, and Winter Park school zones. Don’t miss this rare opportunity to own a truly exceptional home in one of Central Florida’s most desirable communities.

5 Beds ⋅ 6 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

1440 Place Picardy, Winter Park, FL Custom-Built Elegance with Timeless Finishes A custom-built residence completed in 2008 that blends classic craftsmanship with luxurious, modern living. From the moment you step inside, the superior millwork, solid hardwood floors, and elegant design details make a lasting impression. The gourmet kitchen is a chef’s dream, featuring marble countertops, an oversized gas range, and premium DCS and Sub-Zero appliances. It opens seamlessly to a warm and inviting living area, complete with custom built-ins and a cozy gas fireplace—perfect for entertaining or quiet evenings at home. The spacious primary suite is located on the main floor and boasts generous walk-in closets and a versatile adjoining room, ideal for a home office, nursery, or private retreat. Upstairs, you'll find three expansive bedrooms, three full bathrooms, and a versatile bonus room—perfect for guests, hobbies, or a playroom. Lovingly maintained, this home received a new roof in 2021 and features high-quality windows and doors throughout, bathing every room in natural light. No detail was overlooked. Step outside to your private, beautifully landscaped backyard, which includes a second gas fireplace and a detached flex room—currently used as a gym, but easily converted into a private office or studio space. The oversized three-car side-entry garage offers abundant storage and includes a Tesla charger—ideal for electric vehicle owners. Nestled on a peaceful street, this home is just minutes from everything Winter Park has to offer and is located within the highly sought-after Dommerich, Maitland, and Winter Park school zones. Don’t miss this rare opportunity to own a truly exceptional home in one of Central Florida’s most desirable communities.

1400 Place Picardy, Winter Park

$900,000

One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer ~ Welcome to this exceptional –FULLY UPGRADED / POOL HOME– in the highly sought-after Dommerich Estates, where timeless style meets modern design on a spacious .31 ACRE CONSERVATION LOT with serene WOODED VIEWS! Major updates set this home apart; enjoy year round outdoor living with a large lanai featuring motorized retractable screens (2025), a new poolside pergola (2025) and a beautifully resurfaced pool with a sun shelf, new pool deck, and retaining wall (2022). Inside you will find CUSTOM CLOSETS (2025), new PLANTATION SHUTTERS and blinds (2025), FRESH PAINT (2025), an UPDATED ELECTRIC PANEL (2024) and SOLAR PANELS (Owned!) for maximum efficiency. This home also delivers DOUBLE PANE WINDOWS (2020), a NEWER ROOF (2020), WATER HEATER (2019), and a shed for additional outdoor storage was added just this year. Step into a light filled flowing OPEN CONCEPT layout and explore a home designed for both everyday living and entertaining. The heart of the home is the gorgeous CHEF’S KITCHEN, offering the perfect blend of cabinet and drawer storage, open shelving, UPGRADED STAINLESS STEEL APPLIANCES (that include a double wall oven!), sleek countertops, a striking subway tile backsplash and accent wall, and a generous ISLAND with breakfast bar seating. The adjacent dining area boasts a stunning BUILT-IN BAR, ideal for hosting! Throughout the home you will be delighted to find WOOD LOOK TILE and WOOD LAMINATE FLOORING, upgraded light fixtures and fans, elegant crown molding and thoughtful designer touches that elevate every space. The seamless indoor/outdoor flow leads to your private BACKYARD OASIS where you can lounge by the pool, relax under the pergola or gather with guests under the lanai while enjoying the peaceful conservation views. Additional highlights include a CIRCULAR DRIVEWAY, lush landscaping, and fabulous CURB APPEAL. Located in Winter Park with NO HOA this home gives you access to TOP-RATED SCHOOLS and unparalleled convenience being just off Howell Branch Road with easy access to SR 436. You are just minutes away from shopping, dining, parks, and several lakes - all while enjoying the privacy and quiet luxury of this remarkable home. Call today to schedule your tour!

5 Beds ⋅ 3 Baths ⋅ Dommerich Estates SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer ~ Welcome to this exceptional –FULLY UPGRADED / POOL HOME– in the highly sought-after Dommerich Estates, where timeless style meets modern design on a spacious .31 ACRE CONSERVATION LOT with serene WOODED VIEWS! Major updates set this home apart; enjoy year round outdoor living with a large lanai featuring motorized retractable screens (2025), a new poolside pergola (2025) and a beautifully resurfaced pool with a sun shelf, new pool deck, and retaining wall (2022). Inside you will find CUSTOM CLOSETS (2025), new PLANTATION SHUTTERS and blinds (2025), FRESH PAINT (2025), an UPDATED ELECTRIC PANEL (2024) and SOLAR PANELS (Owned!) for maximum efficiency. This home also delivers DOUBLE PANE WINDOWS (2020), a NEWER ROOF (2020), WATER HEATER (2019), and a shed for additional outdoor storage was added just this year. Step into a light filled flowing OPEN CONCEPT layout and explore a home designed for both everyday living and entertaining. The heart of the home is the gorgeous CHEF’S KITCHEN, offering the perfect blend of cabinet and drawer storage, open shelving, UPGRADED STAINLESS STEEL APPLIANCES (that include a double wall oven!), sleek countertops, a striking subway tile backsplash and accent wall, and a generous ISLAND with breakfast bar seating. The adjacent dining area boasts a stunning BUILT-IN BAR, ideal for hosting! Throughout the home you will be delighted to find WOOD LOOK TILE and WOOD LAMINATE FLOORING, upgraded light fixtures and fans, elegant crown molding and thoughtful designer touches that elevate every space. The seamless indoor/outdoor flow leads to your private BACKYARD OASIS where you can lounge by the pool, relax under the pergola or gather with guests under the lanai while enjoying the peaceful conservation views. Additional highlights include a CIRCULAR DRIVEWAY, lush landscaping, and fabulous CURB APPEAL. Located in Winter Park with NO HOA this home gives you access to TOP-RATED SCHOOLS and unparalleled convenience being just off Howell Branch Road with easy access to SR 436. You are just minutes away from shopping, dining, parks, and several lakes - all while enjoying the privacy and quiet luxury of this remarkable home. Call today to schedule your tour!

3011 Temple Trail, Winter Park

$3,100,000

Introducing a stunning brand-new custom home by Butler Ridge Development, located in the highly desirable Park Grove neighborhood—strolling distance to Winter Park’s famed Park Avenue. This home offers timeless elegance, modern luxury, and walkable access to top-tier dining, shopping, and culture. From the inviting circular drive and professionally designed landscaping by Joe Knight, including a signature front palm that sets the tone for this elegant Florida property, every exterior detail makes a statement. Step through the inviting entry into an airy and sun-drenched interior featuring soaring ceilings, wide-plank white oak floors, oversized picture windows, and beautiful crown molding throughout. Inside, a sophisticated office with custom built-ins welcomes you, alongside a thoughtfully designed guest suite with a luxurious bathroom with roll-in shower, soft white finishes, and a custom walk-in closet—ideal for extended family or visitors. The heart of the home is a soaring great room with 14'8" ceilings, a sleek fireplace, and a full wall of sliding glass doors overlooking the resort-style backyard. Entertain with ease in the open-concept living, dining, and chef’s kitchen—complete with a dramatic waterfall island, premium Thermador appliances (including four freezer drawers and diamond ice), dual-fuel range ovens with 6-burner gas cooktop, a 3rd oven + convection microwave, and expansive custom pantry. Adjacent mudroom and decorative laundry room. The first-floor primary suite is a tranquil retreat, featuring pool access, spa bath with soaking tub, separate shower with multiple sprayers, dual vanities, and a spacious custom walk-in closet. Upstairs, a loft-style bonus room complements the smart split-plan layout with 3 additional bedroom suites, walk-ins, and ample storage. Enjoy the best of Florida living in the beautifully landscaped backyard. Designed for both relaxation and entertaining, the outdoor living space includes a saltwater pool with elegant fountain feature, marble pavers, summer kitchen with built-in grill, sink, and beverage fridge, an outdoor bathroom, and ample grassy area for play or pets. 3-Car garage. Located within the highly desirable Dommerich Elementary, Maitland Middle, and Winter Park High School zones, and just minutes from downtown Winter Park, this home offers walkability, elegance, and convenience—wrapped into one exceptional property.

5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

Introducing a stunning brand-new custom home by Butler Ridge Development, located in the highly desirable Park Grove neighborhood—strolling distance to Winter Park’s famed Park Avenue. This home offers timeless elegance, modern luxury, and walkable access to top-tier dining, shopping, and culture. From the inviting circular drive and professionally designed landscaping by Joe Knight, including a signature front palm that sets the tone for this elegant Florida property, every exterior detail makes a statement. Step through the inviting entry into an airy and sun-drenched interior featuring soaring ceilings, wide-plank white oak floors, oversized picture windows, and beautiful crown molding throughout. Inside, a sophisticated office with custom built-ins welcomes you, alongside a thoughtfully designed guest suite with a luxurious bathroom with roll-in shower, soft white finishes, and a custom walk-in closet—ideal for extended family or visitors. The heart of the home is a soaring great room with 14'8" ceilings, a sleek fireplace, and a full wall of sliding glass doors overlooking the resort-style backyard. Entertain with ease in the open-concept living, dining, and chef’s kitchen—complete with a dramatic waterfall island, premium Thermador appliances (including four freezer drawers and diamond ice), dual-fuel range ovens with 6-burner gas cooktop, a 3rd oven + convection microwave, and expansive custom pantry. Adjacent mudroom and decorative laundry room. The first-floor primary suite is a tranquil retreat, featuring pool access, spa bath with soaking tub, separate shower with multiple sprayers, dual vanities, and a spacious custom walk-in closet. Upstairs, a loft-style bonus room complements the smart split-plan layout with 3 additional bedroom suites, walk-ins, and ample storage. Enjoy the best of Florida living in the beautifully landscaped backyard. Designed for both relaxation and entertaining, the outdoor living space includes a saltwater pool with elegant fountain feature, marble pavers, summer kitchen with built-in grill, sink, and beverage fridge, an outdoor bathroom, and ample grassy area for play or pets. 3-Car garage. Located within the highly desirable Dommerich Elementary, Maitland Middle, and Winter Park High School zones, and just minutes from downtown Winter Park, this home offers walkability, elegance, and convenience—wrapped into one exceptional property.

731 Williams Drive, Winter Park

$1,115,000

Endless Potential in the Heart of Park North! Just steps from the charm and energy of Winter Park’s Park Avenue—where boutique cafés, fine dining, art galleries, museums, Central Park, and the Winter Park 9 Golf Course await—this rare Park North gem offers the ultimate opportunity to create your dream home. Nestled at the end of a peaceful cul-de-sac, this expansive .38-acre lot (16,534 SF) is a true find in one of Winter Park’s most desirable neighborhoods. Whether you're looking to build new or renovate the existing residence, the possibilities here are limitless. The current single-story block home spans nearly 3,100 square feet, with strong bones and a layout designed for easy living. Inside you’ll find oversized rooms, a cozy fireplace, a spacious eat-in kitchen, an indoor laundry room, private office off the primary suite, and a 2-car garage. Recent updates—new roof (2023), updated electrical panel (2023), one A/C (2019) and modernized windows and doors—set the stage for your vision to come to life. Natural light fills the home, and the beautifully landscaped backyard offers a serene retreat with a private patio, rear privacy wall, and metal fencing—ideal for both everyday relaxation and stylish entertaining. Located in the coveted Winter Park school district, this is a rare chance to invest in a premium property with endless upside. Whether you choose to reimagine the existing home or build brand new, this is a canvas just waiting for your personal touch. Schedule your private showing today and explore the possibilities! ** SURVEY AVAILABLE IN ATTACHMENTS **

3 Beds ⋅ 4 Baths ⋅ Park North SubDv. ⋅ 32789 Zip Code

Endless Potential in the Heart of Park North! Just steps from the charm and energy of Winter Park’s Park Avenue—where boutique cafés, fine dining, art galleries, museums, Central Park, and the Winter Park 9 Golf Course await—this rare Park North gem offers the ultimate opportunity to create your dream home. Nestled at the end of a peaceful cul-de-sac, this expansive .38-acre lot (16,534 SF) is a true find in one of Winter Park’s most desirable neighborhoods. Whether you're looking to build new or renovate the existing residence, the possibilities here are limitless. The current single-story block home spans nearly 3,100 square feet, with strong bones and a layout designed for easy living. Inside you’ll find oversized rooms, a cozy fireplace, a spacious eat-in kitchen, an indoor laundry room, private office off the primary suite, and a 2-car garage. Recent updates—new roof (2023), updated electrical panel (2023), one A/C (2019) and modernized windows and doors—set the stage for your vision to come to life. Natural light fills the home, and the beautifully landscaped backyard offers a serene retreat with a private patio, rear privacy wall, and metal fencing—ideal for both everyday relaxation and stylish entertaining. Located in the coveted Winter Park school district, this is a rare chance to invest in a premium property with endless upside. Whether you choose to reimagine the existing home or build brand new, this is a canvas just waiting for your personal touch. Schedule your private showing today and explore the possibilities! ** SURVEY AVAILABLE IN ATTACHMENTS **

309 Park North Court, Winter Park

$1,050,000

A RARE Winter Park Estate Blending TIMELESS CRAFTSMANSHIP with MODERN FLEXIBILITY & RESORT-STYLE Living comes to market for the FIRST TIME. 2923 Cove Trail is nestled between the best of Winter Park & Maitland. Masterly created by the renowned Charlie Clayton it blends unmatched craftsmanship with modern design & flexibility craved by you, today’s discerning buyer. REIMAGINED in 2011 this 4-bedroom, 4-bath home features WHITE OAK FLOORS, SOLID WOOD CABINETS, CARRERA MARBLE & TRAVERTINE finishes, along side preserved architectural details like SKIP TROWEL CEILINGS & CROWN MOLDING. Updates fashioned TWO PRIMARY SUITES offering ultimate privacy & flexibility.These SPLIT PLAN suites pack personality. The first provides a POOL VIEW, large WALK-IN CLOSET & SHOWER, while the second basks in the PRIVACY of its own SCREENED GARDEN PATIO & access to a COZY FLEX ROOM with BUILT-INS. Whether used as a SERENITY ROOM, craft space, or restyled into a KITCHENETTE this space adds rare flexibility. Flexibility & MULTIGENERATIONAL living in a ONE STORY home aren’t the only rarities you’ll marvel over. A LARGE SEPARATE OFFICE with PRIVATE EXTERIOR ENTRANCE provides an ideal location for professionals to consult with clients or social media influencers & podcasters to ply their trades. Imagine the freedom & peace of mind you’ll gain not having to worry about traffic while also freeing your business from overhead & lease costs. When the workday ends, entertaining begins & other shiny facets of this home sparkle. A 2,500-BOTTLE CLIMATE-CONTROLLED WINE CELLAR sets the stage for unforgettable gatherings. Whether selecting a vintage for a romantic dinner, indulging guests with formal tastings or kicking back for a relaxed evening you’re sure to savor these moments especially when you move the party outdoors to your PAVERED PATIO adjoining the cool blue waters of your 18x36 RESORT-STYLE POOL all tucked within the PRIVACY of lush 8-foot WALLS. Don’t forget the patio is plumbed for an OUTDOOR BBQ & the pool for SOLAR HEAT when you’re ready to add them.The outdoors isn’t the only place you & your guests will gravitate to. Indoors, enjoy seamless FLOW between the SUNROOM, LIVING room, & FAMILY rooms. BUILT-IN SPEAKERS & STEREO SYSTEMS effortlessly deliver music to your ears. FIREPLACES in both living areas add warmth & ambiance for every season. Some properties claim to have a CHEF'S KITCHEN. This one delivers. Beyond the aesthetic updates, your cooking talents will flourish as you pivot between the island PREP SINK, professional grade 6-BURNER GAS COOKTOP with POT FILLER exceptional overhead VENT, BUILT IN OVENS & stainless steel FRENCH DOOR REFRIGERATOR. For those extra busy celebrations, just around the corner in the laundry room a complement of CABINETS,2ND FULL FREEZER & 2nd REFRIGERATOR await your handiwork while the WASHER & DRYER stand ready for tidying. There’s so much more, but here are a few more highlights:IMPACT-RESISTANT WINDOWS, a PARTIAL HOME GENERATOR, IRRIGATION ON WELL, owned SECURITY SYSTEM & 3 BUILT-IN SAFES— all contributing to your long-term comfort & the home’s efficiency. There’s NO DOUBT this property DELIVERS UNMATCHED VALUE, & QUALITY in one of Winter Park’s MOST DESIRABLE neighborhoods. Homes of this CALIBER RARELY COME TO MARKET— AND WHEN THEY DO THEY DON'T LAST. SCHEDULE your private showing TODAY. This is more than a home — IT'S the LIFESTYLE UPGRADE You've been WAITING FOR. *CLICK on Virtual tour link for 3D Walk Through.*

4 Beds ⋅ 4 Baths ⋅ Dommerich Cove SubDv. ⋅ 32789 Zip Code

A RARE Winter Park Estate Blending TIMELESS CRAFTSMANSHIP with MODERN FLEXIBILITY & RESORT-STYLE Living comes to market for the FIRST TIME. 2923 Cove Trail is nestled between the best of Winter Park & Maitland. Masterly created by the renowned Charlie Clayton it blends unmatched craftsmanship with modern design & flexibility craved by you, today’s discerning buyer. REIMAGINED in 2011 this 4-bedroom, 4-bath home features WHITE OAK FLOORS, SOLID WOOD CABINETS, CARRERA MARBLE & TRAVERTINE finishes, along side preserved architectural details like SKIP TROWEL CEILINGS & CROWN MOLDING. Updates fashioned TWO PRIMARY SUITES offering ultimate privacy & flexibility.These SPLIT PLAN suites pack personality. The first provides a POOL VIEW, large WALK-IN CLOSET & SHOWER, while the second basks in the PRIVACY of its own SCREENED GARDEN PATIO & access to a COZY FLEX ROOM with BUILT-INS. Whether used as a SERENITY ROOM, craft space, or restyled into a KITCHENETTE this space adds rare flexibility. Flexibility & MULTIGENERATIONAL living in a ONE STORY home aren’t the only rarities you’ll marvel over. A LARGE SEPARATE OFFICE with PRIVATE EXTERIOR ENTRANCE provides an ideal location for professionals to consult with clients or social media influencers & podcasters to ply their trades. Imagine the freedom & peace of mind you’ll gain not having to worry about traffic while also freeing your business from overhead & lease costs. When the workday ends, entertaining begins & other shiny facets of this home sparkle. A 2,500-BOTTLE CLIMATE-CONTROLLED WINE CELLAR sets the stage for unforgettable gatherings. Whether selecting a vintage for a romantic dinner, indulging guests with formal tastings or kicking back for a relaxed evening you’re sure to savor these moments especially when you move the party outdoors to your PAVERED PATIO adjoining the cool blue waters of your 18x36 RESORT-STYLE POOL all tucked within the PRIVACY of lush 8-foot WALLS. Don’t forget the patio is plumbed for an OUTDOOR BBQ & the pool for SOLAR HEAT when you’re ready to add them.The outdoors isn’t the only place you & your guests will gravitate to. Indoors, enjoy seamless FLOW between the SUNROOM, LIVING room, & FAMILY rooms. BUILT-IN SPEAKERS & STEREO SYSTEMS effortlessly deliver music to your ears. FIREPLACES in both living areas add warmth & ambiance for every season. Some properties claim to have a CHEF'S KITCHEN. This one delivers. Beyond the aesthetic updates, your cooking talents will flourish as you pivot between the island PREP SINK, professional grade 6-BURNER GAS COOKTOP with POT FILLER exceptional overhead VENT, BUILT IN OVENS & stainless steel FRENCH DOOR REFRIGERATOR. For those extra busy celebrations, just around the corner in the laundry room a complement of CABINETS,2ND FULL FREEZER & 2nd REFRIGERATOR await your handiwork while the WASHER & DRYER stand ready for tidying. There’s so much more, but here are a few more highlights:IMPACT-RESISTANT WINDOWS, a PARTIAL HOME GENERATOR, IRRIGATION ON WELL, owned SECURITY SYSTEM & 3 BUILT-IN SAFES— all contributing to your long-term comfort & the home’s efficiency. There’s NO DOUBT this property DELIVERS UNMATCHED VALUE, & QUALITY in one of Winter Park’s MOST DESIRABLE neighborhoods. Homes of this CALIBER RARELY COME TO MARKET— AND WHEN THEY DO THEY DON'T LAST. SCHEDULE your private showing TODAY. This is more than a home — IT'S the LIFESTYLE UPGRADE You've been WAITING FOR. *CLICK on Virtual tour link for 3D Walk Through.*

2923 Cove Trail, Winter Park

$3,485,000

On one of Winter Park’s most scenic brick-lined streets, this exceptional two-story residence commands attention on a spacious corner lot, blending timeless architectural elegance with modern luxury. Built in 2016 by the highly regarded Rex-Tibbs Development & Construction, the home showcases quality craftsmanship throughout, from its striking curb appeal to its impeccably appointed interiors. A three-car side-entry garage, air-conditioned and offering generous storage, is connected to the home via a covered walkway, adding functionality and charm. Inside, beautiful wood floors extend seamlessly throughout the entire home, including all bedrooms, creating a warm, cohesive atmosphere. The main level offers an elegant formal dining room and a flexible front room that can serve as a home office, library or formal living area. The heart of the home is the expansive family room, anchored by a gas fireplace and illuminated by natural light through large sliding glass doors that open to the lanai and pool. Overlooking the family room, the open-concept kitchen is a culinary dream, featuring a Wolf six-burner gas range with double ovens, Sub-Zero refrigerator, abundant cabinetry and expansive counter space, ideal for everyday living and entertaining. The first-floor primary suite is a retreat, with French doors leading directly to the pool area, a luxurious spa-style bath, and a custom 14-by-10-foot walk-in closet designed for maximum organization and style. A secondary primary suite, also on the main level, includes a generous walk-in closet and a private en-suite bath, offering flexibility for guests or multigenerational living. Upstairs, the home continues to impress with a spacious recreation/game room, a separate bonus room and three additional bedrooms, all of which feature en-suite baths and walk-in closets, ensuring comfort and privacy for family and visitors alike. Step outside to experience resort-style living at its finest. The covered lanai is equipped with a fully outfitted summer kitchen, including a built-in grill, while the pool area is a showstopper, complete with a dramatic gas fire display, tranquil waterfall, ambient lighting, and a lush wall of bamboo that enhances privacy and lends a tropical ambiance. A separate outdoor cabana with TV and seating area offers a place to unwind or entertain in style. Beyond the home, the location is unbeatable. In one of Winter Park’s most desirable neighborhoods, you’re just minutes from the upscale shops, fine dining and cultural attractions of Park Avenue. The home is also conveniently close to top-rated public and private schools, premier medical facilities and major transportation hubs, including the Orlando Executive Airport and Orlando International Airport, ensuring ease of access for business and leisure travel alike. This remarkable property offers the ultimate in refined living, combining luxury, comfort and convenience in one of Central Florida’s sought-after communities.

5 Beds ⋅ 6 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

On one of Winter Park’s most scenic brick-lined streets, this exceptional two-story residence commands attention on a spacious corner lot, blending timeless architectural elegance with modern luxury. Built in 2016 by the highly regarded Rex-Tibbs Development & Construction, the home showcases quality craftsmanship throughout, from its striking curb appeal to its impeccably appointed interiors. A three-car side-entry garage, air-conditioned and offering generous storage, is connected to the home via a covered walkway, adding functionality and charm. Inside, beautiful wood floors extend seamlessly throughout the entire home, including all bedrooms, creating a warm, cohesive atmosphere. The main level offers an elegant formal dining room and a flexible front room that can serve as a home office, library or formal living area. The heart of the home is the expansive family room, anchored by a gas fireplace and illuminated by natural light through large sliding glass doors that open to the lanai and pool. Overlooking the family room, the open-concept kitchen is a culinary dream, featuring a Wolf six-burner gas range with double ovens, Sub-Zero refrigerator, abundant cabinetry and expansive counter space, ideal for everyday living and entertaining. The first-floor primary suite is a retreat, with French doors leading directly to the pool area, a luxurious spa-style bath, and a custom 14-by-10-foot walk-in closet designed for maximum organization and style. A secondary primary suite, also on the main level, includes a generous walk-in closet and a private en-suite bath, offering flexibility for guests or multigenerational living. Upstairs, the home continues to impress with a spacious recreation/game room, a separate bonus room and three additional bedrooms, all of which feature en-suite baths and walk-in closets, ensuring comfort and privacy for family and visitors alike. Step outside to experience resort-style living at its finest. The covered lanai is equipped with a fully outfitted summer kitchen, including a built-in grill, while the pool area is a showstopper, complete with a dramatic gas fire display, tranquil waterfall, ambient lighting, and a lush wall of bamboo that enhances privacy and lends a tropical ambiance. A separate outdoor cabana with TV and seating area offers a place to unwind or entertain in style. Beyond the home, the location is unbeatable. In one of Winter Park’s most desirable neighborhoods, you’re just minutes from the upscale shops, fine dining and cultural attractions of Park Avenue. The home is also conveniently close to top-rated public and private schools, premier medical facilities and major transportation hubs, including the Orlando Executive Airport and Orlando International Airport, ensuring ease of access for business and leisure travel alike. This remarkable property offers the ultimate in refined living, combining luxury, comfort and convenience in one of Central Florida’s sought-after communities.

2171 Forrest Road, Winter Park

$8,900,000

Discover an extraordinary lifestyle at this one-of-a-kind estate, elegantly situated on the shores of Lake Maitland in the distinguished Winter Park area. This remarkable property is unlike any other in the market, seamlessly blending sophisticated Mediterranean and Spanish architectural elements to create a serene and inviting retreat. Upon entering through the stately steel gates, you are welcomed by a picturesque, tree-lined driveway that leads to a formal motor court, enveloped in lush, mature landscaping that ensures complete privacy. Spanning an expansive 2.10 acres with an impressive 217 feet of lake frontage, this estate offers a breathtaking park-like setting that is perfect for both relaxation and vibrant entertaining. The primary residence encompasses six generously sized bedrooms and 6.5 luxurious baths, featuring exquisite traditional custom details and an abundance of elegant living space. Outside, indulge in the stunning waterside rose garden and pavilion, alongside an expansive pool designed for year-round enjoyment and perfect for hosting guests. This estate also boasts a delightful gatehouse, which includes a one-bedroom, one-bath suite and a dedicated two-car garage, providing an ideal retreat for visitors. Additionally, a separate lake house, constructed in 2004, features richly hued wooden vaulted ceilings, a cozy stone fireplace, and a generously sized covered porch that spans the length of the home showcasing spectacular views of the water and gardens. This property transcends the notion of a mere home; it embodies a truly unique lifestyle. Whether you desire serene lakeside tranquility or a sumptuous entertainer's haven, this exceptional offering presents an unmatched opportunity to own a slice of paradise in Winter Park. As you step through the grand double-door entry of the main residence, you are enveloped in elegance and comfort. This thoughtfully designed home balances functionality with style, featuring dual office suites, a game room, and ample storage space throughout, catering to the demands of modern living. The awe-inspiring 22.5-foot ceilings in the grand foyer and dining room create an impressive ambiance, illuminated by uniquely designed windows that flood the space with natural light. The smartly designed floor plan ensures both privacy and convenience, with the primary suite thoughtfully positioned in a secluded area of the home, while an additional main-level bedroom provides flexibility for guests or family. The expansive kitchen is a culinary dream, boasting a spacious island, breakfast bar, a walk-in pantry, and a gas cook range, all seamlessly connected to a cozy dinette area. Upstairs, you’ll find four additional bedrooms and three beautifully renovated bathrooms that prioritize comfort and space. Step outside to an oversized screened and covered lanai, complete with multiple skylights that invite the beauty of the outdoors inside, perfect for relaxation or entertaining. Enjoy captivating views of the pool area, rose garden with Tea House, and tranquil lake, creating an idyllic backdrop for both peaceful moments and lively gatherings. This main residence is a sophisticated blend of luxury and practicality, designed for those who truly appreciate the finer things in life. Don’t miss this rare opportunity to claim this stunning residence as your own—schedule a private showing today to experience the unparalleled elegance and uniqueness of this extraordinary estate!

8 Beds ⋅ 9 Baths ⋅ Green Oaks Rep 02 SubDv. ⋅ 32789 Zip Code

Discover an extraordinary lifestyle at this one-of-a-kind estate, elegantly situated on the shores of Lake Maitland in the distinguished Winter Park area. This remarkable property is unlike any other in the market, seamlessly blending sophisticated Mediterranean and Spanish architectural elements to create a serene and inviting retreat. Upon entering through the stately steel gates, you are welcomed by a picturesque, tree-lined driveway that leads to a formal motor court, enveloped in lush, mature landscaping that ensures complete privacy. Spanning an expansive 2.10 acres with an impressive 217 feet of lake frontage, this estate offers a breathtaking park-like setting that is perfect for both relaxation and vibrant entertaining. The primary residence encompasses six generously sized bedrooms and 6.5 luxurious baths, featuring exquisite traditional custom details and an abundance of elegant living space. Outside, indulge in the stunning waterside rose garden and pavilion, alongside an expansive pool designed for year-round enjoyment and perfect for hosting guests. This estate also boasts a delightful gatehouse, which includes a one-bedroom, one-bath suite and a dedicated two-car garage, providing an ideal retreat for visitors. Additionally, a separate lake house, constructed in 2004, features richly hued wooden vaulted ceilings, a cozy stone fireplace, and a generously sized covered porch that spans the length of the home showcasing spectacular views of the water and gardens. This property transcends the notion of a mere home; it embodies a truly unique lifestyle. Whether you desire serene lakeside tranquility or a sumptuous entertainer's haven, this exceptional offering presents an unmatched opportunity to own a slice of paradise in Winter Park. As you step through the grand double-door entry of the main residence, you are enveloped in elegance and comfort. This thoughtfully designed home balances functionality with style, featuring dual office suites, a game room, and ample storage space throughout, catering to the demands of modern living. The awe-inspiring 22.5-foot ceilings in the grand foyer and dining room create an impressive ambiance, illuminated by uniquely designed windows that flood the space with natural light. The smartly designed floor plan ensures both privacy and convenience, with the primary suite thoughtfully positioned in a secluded area of the home, while an additional main-level bedroom provides flexibility for guests or family. The expansive kitchen is a culinary dream, boasting a spacious island, breakfast bar, a walk-in pantry, and a gas cook range, all seamlessly connected to a cozy dinette area. Upstairs, you’ll find four additional bedrooms and three beautifully renovated bathrooms that prioritize comfort and space. Step outside to an oversized screened and covered lanai, complete with multiple skylights that invite the beauty of the outdoors inside, perfect for relaxation or entertaining. Enjoy captivating views of the pool area, rose garden with Tea House, and tranquil lake, creating an idyllic backdrop for both peaceful moments and lively gatherings. This main residence is a sophisticated blend of luxury and practicality, designed for those who truly appreciate the finer things in life. Don’t miss this rare opportunity to claim this stunning residence as your own—schedule a private showing today to experience the unparalleled elegance and uniqueness of this extraordinary estate!

2001 Bett Mar Lane, Winter Park

$600,000

Value is in the land.

3 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace 2nd Add SubDv. ⋅ 32789 Zip Code

Value is in the land.

1550 Palm Avenue, Winter Park

$440,000

WINTER PARK 32789 - Mid Century design. Unique neighborhood - walk to shopping, restaurants, entertainment. 3/1.5 Bath with large Florida Room. 2 Car Carport.

3 Beds ⋅ 2 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code

WINTER PARK 32789 - Mid Century design. Unique neighborhood - walk to shopping, restaurants, entertainment. 3/1.5 Bath with large Florida Room. 2 Car Carport.

3019 Northwood Boulevard, Winter Park

$1,375,000

This home is a charming and meticulously maintained single-story family home nestled on a quiet street located on an expansive beautifully landscaped lot. As you enter, you're greeted by a private office with French doors to the left, and to the right, a cozy family room featuring a decorative fireplace. The open concept living and dining areas overlook the backyard, creating a perfect flow for gatherings. The kitchen, which also overlooks the backyard, features granite countertops, wood cabinetry, and under cabinetry lighting. The home boasts beautiful bamboo flooring throughout most of the living spaces and it has been thoughtfully designed with crown molding and baseboards throughout. A split floor plan offers privacy with the primary suite located on one side of the home. The stunning master bathroom, remodeled in 2024, features a large soaking tub, dual vanities and a walk-in shower. Enjoy the massive walk-in closet with custom built-ins. The primary retreat boasts vaulted wood plank ceilings and French doors which open to the pool area, creating a true retreat. On the opposite side of the home, you’ll find three additional bedrooms, all with built-in closets. The largest of these bedrooms has an ensuite bath, while the other two share a bath with a tub and shower combo. There is also a convenient half-bath off the family room, perfect for guests. The home sits on a spacious, over quarter acre lot, offering a massive backyard oasis complete with a saltwater pool, spa, and a covered patio area perfect for entertaining. The backyard is an entertainer’s dream with a summer kitchen, bar fridge, sink, and wood plank ceiling over the covered patio. The fully fenced yard offers plenty of space for outdoor activities. Additional updates include a 2021 roof, 2021 a/c for primary bedroom, 2024 a/c for main house and exterior paint in 2022, primary retreat and wing added in 2013. The home is located within a highly sought-after Winter Park neighborhood. It's walking distance to Phelps Park and just a short drive to the charming shops and dining on Park Avenue.

4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

This home is a charming and meticulously maintained single-story family home nestled on a quiet street located on an expansive beautifully landscaped lot. As you enter, you're greeted by a private office with French doors to the left, and to the right, a cozy family room featuring a decorative fireplace. The open concept living and dining areas overlook the backyard, creating a perfect flow for gatherings. The kitchen, which also overlooks the backyard, features granite countertops, wood cabinetry, and under cabinetry lighting. The home boasts beautiful bamboo flooring throughout most of the living spaces and it has been thoughtfully designed with crown molding and baseboards throughout. A split floor plan offers privacy with the primary suite located on one side of the home. The stunning master bathroom, remodeled in 2024, features a large soaking tub, dual vanities and a walk-in shower. Enjoy the massive walk-in closet with custom built-ins. The primary retreat boasts vaulted wood plank ceilings and French doors which open to the pool area, creating a true retreat. On the opposite side of the home, you’ll find three additional bedrooms, all with built-in closets. The largest of these bedrooms has an ensuite bath, while the other two share a bath with a tub and shower combo. There is also a convenient half-bath off the family room, perfect for guests. The home sits on a spacious, over quarter acre lot, offering a massive backyard oasis complete with a saltwater pool, spa, and a covered patio area perfect for entertaining. The backyard is an entertainer’s dream with a summer kitchen, bar fridge, sink, and wood plank ceiling over the covered patio. The fully fenced yard offers plenty of space for outdoor activities. Additional updates include a 2021 roof, 2021 a/c for primary bedroom, 2024 a/c for main house and exterior paint in 2022, primary retreat and wing added in 2013. The home is located within a highly sought-after Winter Park neighborhood. It's walking distance to Phelps Park and just a short drive to the charming shops and dining on Park Avenue.

1633 Pine Avenue, Winter Park

$575,000

This charming “old Florida” bungalow in the heart of Winter Park offers the perfect blend of comfort and convenience, nestled in a prime location on a brick lined street just moments from world-class shopping and dining on famous Park Avenue. In addition, it is a short walk to both The Winter Park Village and Whole Foods. The warm and inviting interior of this home exudes character with original hardwood flooring in the spacious living room as well as both bedrooms. The hall bathroom has been updated with a new vanity, granite countertop, and marble tile. The well-appointed kitchen has Italian travertine flooring, Shaker-style 42" wood cabinets, granite countertops with an under-mount sink bowl, and beautiful stainless-steel appliances. Just off the kitchen is a cozy dining room which is perfect for family gatherings. New roof in (2021) and a 1 car garage! The property is zoned for top rated Lakemont Elementary, Maitland Middle, and Winter Park High School. Surrounded by Muti-Million Dollar homes this is a rare opportunity to move in now and wait for future appreciation, add on, or maximize the value of the land and build your dream home. The homes proximity to The Winter Park Cultural Corridor which includes Rollins College, The Morse Museum, The Scenic Boat Tour, and The Farmer’s Market make this a most sought-after location. Schedule your private showing today!

2 Beds ⋅ 1 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

This charming “old Florida” bungalow in the heart of Winter Park offers the perfect blend of comfort and convenience, nestled in a prime location on a brick lined street just moments from world-class shopping and dining on famous Park Avenue. In addition, it is a short walk to both The Winter Park Village and Whole Foods. The warm and inviting interior of this home exudes character with original hardwood flooring in the spacious living room as well as both bedrooms. The hall bathroom has been updated with a new vanity, granite countertop, and marble tile. The well-appointed kitchen has Italian travertine flooring, Shaker-style 42" wood cabinets, granite countertops with an under-mount sink bowl, and beautiful stainless-steel appliances. Just off the kitchen is a cozy dining room which is perfect for family gatherings. New roof in (2021) and a 1 car garage! The property is zoned for top rated Lakemont Elementary, Maitland Middle, and Winter Park High School. Surrounded by Muti-Million Dollar homes this is a rare opportunity to move in now and wait for future appreciation, add on, or maximize the value of the land and build your dream home. The homes proximity to The Winter Park Cultural Corridor which includes Rollins College, The Morse Museum, The Scenic Boat Tour, and The Farmer’s Market make this a most sought-after location. Schedule your private showing today!

1230 N Denning Drive, Winter Park

$2,935,000

One of Winter Park’s iconic and cherished homes, just a short distance from Park Avenue. On one of the most picturesque, brick-lined streets in downtown Winter Park, this extraordinary residence is a rare opportunity to own a piece of the city’s rich architectural history, fully reimagined with modern elegance and thoughtful design. On the same city block as the Alfond Inn and a two-block stroll to the world-renowned Park Avenue, this home offers not only luxurious living but an unparalleled lifestyle in one of Central Florida’s sought-after communities. Park Avenue is the heartbeat of Winter Park, a tree-lined promenade brimming with charm, home to award-winning restaurants, boutique shopping, art galleries and cultural landmarks. Residents and visitors alike are drawn to its timeless ambiance, where the rhythm of the day flows from morning coffee at a corner café to evening dinners under twinkling lights. Whether enjoying “Movies in the Park,” seasonal art festivals, the lively Winter Park Farmers’ Market or beloved holiday parades, living here means having a front-row seat to all of Winter Park’s treasured traditions. Originally built in the 1930s, this five-bedroom, 5.5-bath home has been meticulously renovated in recent years to preserve its historic character while seamlessly incorporating every modern convenience. From the moment you enter, you’re greeted by gleaming hardwood floors, classic architectural details and a warm, inviting atmosphere. The gracious living room centers around a charming fireplace, flanked by two sets of French doors that lead to a cozy sunroom, ideal for morning coffee or afternoon reading. A formal dining room provides an elegant setting for entertaining, while the open-concept kitchen and family room encompass a blend of functionality and style. The kitchen is a showpiece, featuring a large 15-foot Soma quartz island and countertops and marble backsplash, handcrafted cabinetry, top-of-the-line Wolf and Sub-Zero appliances, and a custom wet bar with under-counter wine refrigerator. It’s a space designed for gatherings, large or small. The expansive and private primary suite is on the main level and features a walk-in closet with custom built-ins and a luxurious en-suite bath with dual sinks and a marble/glass shower. Upstairs, you’ll find three additional bedroom suites, including one that could easily serve as a second primary suite, complete with French doors leading to a covered balcony. Each bedroom offers its own en-suite bath, hardwood floors and thoughtfully designed closet space with built-ins. A spacious first-floor laundry room offers ample storage, while the detached two-car garage includes a beautifully renovated first-floor guest cottage. Complete with a kitchenette, full bath, and cedar-lined walk-in closet, it’s the ideal space for guests, a home office or extended family. Surrounded by lush landscaping and a charming circular driveway, this home radiates curb appeal and classic Winter Park style. Whether you're walking to Park Avenue for dinner, enjoying a leisurely afternoon in Central Park, or simply soaking in the historic beauty of your neighborhood, this home places you at the center of it all. This is more than just a home, it’s a lifestyle and a rare chance to own one of Winter Park’s rare downtown area treasured properties.

5 Beds ⋅ 6 Baths ⋅ Gibbs Sub SubDv. ⋅ 32789 Zip Code

One of Winter Park’s iconic and cherished homes, just a short distance from Park Avenue. On one of the most picturesque, brick-lined streets in downtown Winter Park, this extraordinary residence is a rare opportunity to own a piece of the city’s rich architectural history, fully reimagined with modern elegance and thoughtful design. On the same city block as the Alfond Inn and a two-block stroll to the world-renowned Park Avenue, this home offers not only luxurious living but an unparalleled lifestyle in one of Central Florida’s sought-after communities. Park Avenue is the heartbeat of Winter Park, a tree-lined promenade brimming with charm, home to award-winning restaurants, boutique shopping, art galleries and cultural landmarks. Residents and visitors alike are drawn to its timeless ambiance, where the rhythm of the day flows from morning coffee at a corner café to evening dinners under twinkling lights. Whether enjoying “Movies in the Park,” seasonal art festivals, the lively Winter Park Farmers’ Market or beloved holiday parades, living here means having a front-row seat to all of Winter Park’s treasured traditions. Originally built in the 1930s, this five-bedroom, 5.5-bath home has been meticulously renovated in recent years to preserve its historic character while seamlessly incorporating every modern convenience. From the moment you enter, you’re greeted by gleaming hardwood floors, classic architectural details and a warm, inviting atmosphere. The gracious living room centers around a charming fireplace, flanked by two sets of French doors that lead to a cozy sunroom, ideal for morning coffee or afternoon reading. A formal dining room provides an elegant setting for entertaining, while the open-concept kitchen and family room encompass a blend of functionality and style. The kitchen is a showpiece, featuring a large 15-foot Soma quartz island and countertops and marble backsplash, handcrafted cabinetry, top-of-the-line Wolf and Sub-Zero appliances, and a custom wet bar with under-counter wine refrigerator. It’s a space designed for gatherings, large or small. The expansive and private primary suite is on the main level and features a walk-in closet with custom built-ins and a luxurious en-suite bath with dual sinks and a marble/glass shower. Upstairs, you’ll find three additional bedroom suites, including one that could easily serve as a second primary suite, complete with French doors leading to a covered balcony. Each bedroom offers its own en-suite bath, hardwood floors and thoughtfully designed closet space with built-ins. A spacious first-floor laundry room offers ample storage, while the detached two-car garage includes a beautifully renovated first-floor guest cottage. Complete with a kitchenette, full bath, and cedar-lined walk-in closet, it’s the ideal space for guests, a home office or extended family. Surrounded by lush landscaping and a charming circular driveway, this home radiates curb appeal and classic Winter Park style. Whether you're walking to Park Avenue for dinner, enjoying a leisurely afternoon in Central Park, or simply soaking in the historic beauty of your neighborhood, this home places you at the center of it all. This is more than just a home, it’s a lifestyle and a rare chance to own one of Winter Park’s rare downtown area treasured properties.

266 Chase Avenue, Winter Park

$1,250,000

Discover luxurious lakeside living in prestigious Winter Park, where this extensively updated pool home offers the perfect blend of sophisticated main residence and private guest cottage. Just minutes from Park Avenue's renowned shopping and dining, this property provides coveted access to Lake Osceola, creating an ideal setting for the Florida lifestyle. The main residence showcases elegant living spaces, including a grand room with hardwood floors and a welcoming fireplace. The gourmet kitchen is a chef's dream, featuring premium Wolf and Sub-Zero appliances, gleaming granite countertops, and a distinctive bead-board center island that opens to a spacious family room. A wall of French doors in the formal dining room creates seamless indoor-outdoor flow to the screened pool and spa area. The thoughtful floor plan includes a downstairs master suite with custom walk-in closet, dual-sink bathroom, and versatile 13x12 flex space. Two additional en-suite bedrooms upstairs provide comfortable accommodations for family or guests. The separate guest cottage adds tremendous value with two bedrooms, a full kitchen, and bathroom – perfect for long-term guests or home office. Recent updates ensure peace of mind: new roof (2025), two new AC units (2023), complete replumbing (2015), and updated electrical. The property offers abundant parking with a two-car garage plus an additional one-car garage with full bath. Located in Winter Park's prestigious school district, this home represents the perfect combination of luxury, convenience, and long-term value.

5 Beds ⋅ 6 Baths ⋅ Galloway Place Rep SubDv. ⋅ 32789 Zip Code

Discover luxurious lakeside living in prestigious Winter Park, where this extensively updated pool home offers the perfect blend of sophisticated main residence and private guest cottage. Just minutes from Park Avenue's renowned shopping and dining, this property provides coveted access to Lake Osceola, creating an ideal setting for the Florida lifestyle. The main residence showcases elegant living spaces, including a grand room with hardwood floors and a welcoming fireplace. The gourmet kitchen is a chef's dream, featuring premium Wolf and Sub-Zero appliances, gleaming granite countertops, and a distinctive bead-board center island that opens to a spacious family room. A wall of French doors in the formal dining room creates seamless indoor-outdoor flow to the screened pool and spa area. The thoughtful floor plan includes a downstairs master suite with custom walk-in closet, dual-sink bathroom, and versatile 13x12 flex space. Two additional en-suite bedrooms upstairs provide comfortable accommodations for family or guests. The separate guest cottage adds tremendous value with two bedrooms, a full kitchen, and bathroom – perfect for long-term guests or home office. Recent updates ensure peace of mind: new roof (2025), two new AC units (2023), complete replumbing (2015), and updated electrical. The property offers abundant parking with a two-car garage plus an additional one-car garage with full bath. Located in Winter Park's prestigious school district, this home represents the perfect combination of luxury, convenience, and long-term value.

1370 Alberta Drive, Winter Park

$1,810,000

Experience modern luxury in this stunning custom-built residence by LunDev Custom Homes, positioned in the heart of Winter Park. Built in 2015, this contemporary home offers four bedrooms, 3.5 baths and 3,440 heated square feet, seamlessly blending elegant design with state-of-the-art smart home technology. The first-floor primary suite is a serene retreat featuring a spacious walk-in closet and a spa-like en-suite bath with dual sinks, a glass-enclosed shower, a separate soaking tub and a private water closet. The formal living room is highlighted by French doors opening to a beautifully designed side yard with low-maintenance artificial turf, creating an indoor-outdoor flow. At the heart of the home, the open-concept kitchen is a chef’s dream, boasting a large island that overlooks the dining and family rooms, ideal for everyday living and entertaining. A dramatic wall of glass doors seamlessly extends the living space to the covered lanai, complete with motorized screens for year-round enjoyment. Recent upgrades, including fresh interior and exterior paint, Philips Hue smart lighting, smart wall switches and new smart locks, enhance style and convenience. Step outside to your private resort-style oasis, where a sparkling pool, built-in gas grill, ceramic Coyote Asado smoker and pergola-covered seating area set the stage for unforgettable gatherings. An outdoor shower and a lush Vistafolia artificial green wall system, illuminated by Philips Hue backlighting, add to the ambiance. A covered walkway connects the home to a detached two-car garage, offering functionality and architectural charm. Upstairs, a versatile bonus room/loft with gym flooring provides endless possibilities, accompanied by three additional bedrooms, two featuring walk-in closets and one with dual closets and an en-suite bath. Additional enhancements include a Ring security system, a new pool filter and skimmer, and upgraded front yard landscaping, ensuring this home is move-in ready. Just minutes from downtown Winter Park’s Park Avenue, Baldwin Park Village Center, and premier dining and shopping, with easy access to downtown Orlando and Orlando International Airport, this residence offers the ideal balance of luxury, comfort and convenience. Don’t miss this opportunity and schedule your private showing today!

4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Experience modern luxury in this stunning custom-built residence by LunDev Custom Homes, positioned in the heart of Winter Park. Built in 2015, this contemporary home offers four bedrooms, 3.5 baths and 3,440 heated square feet, seamlessly blending elegant design with state-of-the-art smart home technology. The first-floor primary suite is a serene retreat featuring a spacious walk-in closet and a spa-like en-suite bath with dual sinks, a glass-enclosed shower, a separate soaking tub and a private water closet. The formal living room is highlighted by French doors opening to a beautifully designed side yard with low-maintenance artificial turf, creating an indoor-outdoor flow. At the heart of the home, the open-concept kitchen is a chef’s dream, boasting a large island that overlooks the dining and family rooms, ideal for everyday living and entertaining. A dramatic wall of glass doors seamlessly extends the living space to the covered lanai, complete with motorized screens for year-round enjoyment. Recent upgrades, including fresh interior and exterior paint, Philips Hue smart lighting, smart wall switches and new smart locks, enhance style and convenience. Step outside to your private resort-style oasis, where a sparkling pool, built-in gas grill, ceramic Coyote Asado smoker and pergola-covered seating area set the stage for unforgettable gatherings. An outdoor shower and a lush Vistafolia artificial green wall system, illuminated by Philips Hue backlighting, add to the ambiance. A covered walkway connects the home to a detached two-car garage, offering functionality and architectural charm. Upstairs, a versatile bonus room/loft with gym flooring provides endless possibilities, accompanied by three additional bedrooms, two featuring walk-in closets and one with dual closets and an en-suite bath. Additional enhancements include a Ring security system, a new pool filter and skimmer, and upgraded front yard landscaping, ensuring this home is move-in ready. Just minutes from downtown Winter Park’s Park Avenue, Baldwin Park Village Center, and premier dining and shopping, with easy access to downtown Orlando and Orlando International Airport, this residence offers the ideal balance of luxury, comfort and convenience. Don’t miss this opportunity and schedule your private showing today!

1970 Laurel Road, Winter Park