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$940,000
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

$458,000
3 Beds 1 Baths Bungalow Park SubDv. 32789 Zip Code
One or more photo(s) has been virtually staged. Location, Location, Location! Nestled in the heart of highly sought-after Winter Park, this charming 3 bedroom home offers the perfect blend of vintage character and modern updates. Just steps away from Park Avenue, Hannibal Square, and the city’s historic district, you’ll enjoy walkable access to upscale shopping, fine dining, and everything Winter Park is known for. Step inside to a light-filled, spacious living room featuring beautiful wood flooring and timeless charm. The separate dining room also boasts wood floors and a large picture window, perfect for hosting intimate dinners or enjoying family meals. The kitchen retains some of its original charm while offering new stainless-steel appliances and ample cabinetry. One of the standout features of this home is the expansive bonus room formerly the garage highlighted by decorative wood beams and endless possibilities for a home office, studio, or entertainment space. The private, fenced backyard is ideal for outdoor living, with plenty of room for gatherings, BBQs, or relaxing under the stars. Situated on R-2 zoning, this property also presents additional future potential in one of Central Florida’s most desirable neighborhoods. Don’t miss the opportunity to own a home in one of Winter Park’s most iconic and walkable locations!!!

955 Minnesota Avenue, Winter Park

$5,225,000
3 Beds 4 Baths Galloway Place Rep SubDv. 32789 Zip Code
An architectural triumph, this one-of-a-kind modern masterpiece was custom designed and built in 2023 by the award-winning Z Properties and is ideally sited on the shores of Lake Osceola, part of the Winter Park Chain of Lakes. Radiating bold sophistication and contemporary elegance, the residence is a curated work of art, where floor-to-ceiling glass walls and striking steel windows and doors flood the interiors with natural light and deliver unobstructed panoramic lake views from nearly every room. Enter through a dramatic 12-foot glass pivot door into a 21-foot-long art gallery foyer adorned with a sculptural linear chandelier and Venetian plaster walls and ceilings that lend a soft, refined texture. The open-concept living spaces are accentuated by terrazzo floors, 12-foot ceilings, and thoughtful spatial design—including a great room with a sitting area and dining space, a separate media room concealed behind custom 12-foot decorative doors, and a sleek galley-style kitchen outfitted with fully integrated Miele appliances and a secondary glass pivot door for seamless indoor-outdoor flow. Ascending one of two custom staircases, the second floor features warm hardwood floors and a showstopping primary suite that feels suspended above the lake, backyard and pool. This serene retreat offers an all-glass shower, spa-inspired soaking tub, beautifully finished bath cabinetry, and an upholstered wall that subtly conceals a walk-in closet and built-in storage. A second bedroom suite offers an inspired use of space with clever screen walls for privacy and flexibility. Detached from the main home, a third bedroom suite doubles as a guest house, home office, or gym, complete with an en-suite bath, custom built-ins and a wet bar. Outside, the terraced backyard is a tranquil oasis with a saltwater pool and spa, turf lawn for year-round perfection, dual staircases leading to a sundeck and a private, covered boat dock crowned by a glass-enclosed studio mirroring the home’s signature design. Bamboo privacy walls, soaring palms, and a Banyan tree imported from South Florida create a lush and artful landscape. The two-car garage includes epoxy flooring and dual EV charging stations. A singular residence in every sense, this home blends innovative architecture, luxurious finishes and thoughtful design into a rare offering unlike anything else in Winter Park. Built by Z Properties, celebrated in Florida Design and numerous design publications, this is a home for those who appreciate beauty, intention and the art of living well.

1333 Alberta Drive, Winter Park

$980,000
3 Beds 3 Baths Lake Knowles Terrace SubDv. 32789 Zip Code
Nestled in the desirable Tree Streets of Winter Park, this stunning Mid-Century Modern residence offers timeless style, thoughtful updates, and effortless indoor-outdoor living. With over 2,100 square feet of beautifully designed space, this 3-bedroom, 2.5-bath home delivers modern functionality with elegant character—just minutes from the heart of Park Avenue. Inside, you'll find an open floor plan with engineered hardwood flooring, high ceilings, crown molding, and abundant natural light. The kitchen is a chef’s dream, featuring a convection oven, cooktop, range hood, and brand-new appliances—ideal for both daily living and entertaining. A wet bar with wine fridge, cozy sunroom, and custom closets in all three bedrooms elevate the home’s comfort and convenience. The primary suite is located upstairs, offering privacy and retreat. The backyard is a true Florida oasis, complete with a newly resurfaced saltwater pool, expansive artificial turf, a custom putting green, and a deck with a retractable awning—all within a fully fenced yard designed for privacy and year-round enjoyment. Additional upgrades include a new roof (2020), updated A/C system (2021), garage storage solutions, and lush front landscaping. With no HOA, a 2-car garage, and extended driveway parking for 4+ vehicles, this home offers both style and flexibility in one of Winter Park’s most coveted neighborhoods. A rare opportunity to own a turnkey home in a prime location—schedule your private showing today.

1610 Chestnut Avenue, Winter Park

$775,000
2 Beds 2 Baths Cloisters Condo SubDv. 32789 Zip Code
Welcome to The Cloisters—a prestigious lakefront community nestled in the heart of Winter Park, perfectly positioned between the timeless charm of Park Avenue and the serene beauty of Lake Osceola. This fully furnished second-floor residence has been meticulously redesigned and renovated to maximize both space and style, offering the comfort of a thoughtfully designed home, enhanced by luxurious, designer-selected finishes throughout. Step inside to discover a beautifully appointed interior featuring high-end touches. The kitchen is a true showpiece, boasting custom wood cabinetry with artistic wood detailing, granite countertops, full counter-to-cabinet backsplashes, and top-tier appliances including a Wolf cooktop and oven, Fisher & Paykel dishwasher, Liebherr wine cooler, and Sub-Zero refrigerator. The expansive kitchen island comfortably seats four, with a sleek, integrated extension that effortlessly accommodates up to seven—perfect for entertaining in style. The open-concept living area flows seamlessly to a spacious private balcony, offering tranquil views of the heated pool, putting green, lush landscaping, and the shimmering waters of Lake Osceola—ideal for a morning coffee or year-round entertaining. The primary suite is a serene retreat, featuring blackout blinds, a Sleep Number smart bed with dual temperature controls, and custom floor-to-ceiling built-ins with integrated lighting, display shelving, and a dedicated vanity area. Additional built-in cabinetry lines the hallway leading to the en-suite bathroom, providing ample space for jewelry, shoes, and wardrobe essentials. The second bedroom is designed for versatility, with a wall-to-wall built-in home office setup overlooking a beautiful resort-style view, along with its own matching floor-to-ceiling built-ins for display and storage. Both bathrooms have been tastefully reimagined with new vanities, granite countertops, upgraded shower enclosures and hardware, and stylish lighting and mirrors. The primary bath includes additional custom built-ins for optimal storage and organization. Throughout the home, fresh paint and luxury vinyl flooring create a clean, modern aesthetic. Additional features include an in-unit washer and dryer tucked behind a custom wood door, a built-in safe, and a new A/C unit installed in 2024. The residence also includes a deeded covered-parking space and a private storage unit. The Cloisters community offers a wealth of amenities, including an onsite property manager, ample guest parking, elevators, a heated pool, onsite laundry facilities, a putting green, private lake access, a dock, and boat slips available via resident lottery. Residents also enjoy two fitness centers with one dry sauna and a recently updated clubhouse with a full kitchen and bath—ideal for private gatherings. Just a short stroll from the boutiques, restaurants, and cultural attractions of Park Avenue, and Rollins College, this fully renovated, turnkey residence presents a rare opportunity to enjoy the ultimate blend of location, luxury, and lifestyle. Realtor/owner is a licensed Florida real estate broker.

100 S Interlachen Avenue Unit 204D, Winter Park

$312,000
3 Beds 2 Baths Stansbury Estates SubDv. 32789 Zip Code
$5K SELLER CONCESSION TOWARDS BUYER'S CLOSING COSTS AND PRE-PAIDS!!! Charming, Fully Renovated Bungalow in the Heart of Winter Park! Welcome to this beautifully upgraded bungalow that makes every square foot count! Nestled perfectly between Winter Park and College Park, this fully renovated gem blends modern upgrades with timeless charm. From the moment you arrive, the custom-built front pergola and all-new paver driveway invite you in with style. Step inside to discover a cozy yet efficient layout filled with thoughtful details: barn doors, built-ins, a cabinet pantry, and a linen closet in the guest bath that add character and storage throughout. The brand-new kitchen is compact but packed with quality—featuring granite countertops, stainless steel appliances, and custom cabinetry that maximizes function and charm. The spacious primary suite offers a walk-in closet and an en-suite bath with a very large walk-in shower. Other unique features include a charming barn door to separate the laundry area from the guest bath, optimizing flow and privacy, an extended and brand new paver driveway, along with a beautiful custom fence and storage sheds that provides added storage. This charming bungalow has been designed to live larger than its footprint. Don’t miss your chance to own this thoughtfully designed home in one of Central Florida’s most desirable locations!

1921 Dartmouth Avenue, Winter Park

$1,575,000
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

$3,975,000
4 Beds 6 Baths Cloister Grove Sub SubDv. 32789 Zip Code
In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement with organic warmth. Now offered at a compelling new price, the home presents a rare opportunity to experience architecturally distinctive new construction in the Vias neighborhood. Conceived, developed & designed by Steve & Jodie Konold of Scout & Co., the 3,850-sf residence offers 4 beds & 5.5 baths, w/ a layout thoughtfully arranged to provide the intentional privacy of a luxury retreat. Beyond its terraced walkway—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer featuring a woven rattan chandelier, sourced & designed in London, leads to a sculptural stairwell positioned just off the main living spaces. The great room includes soaring ceilings, a sleek, custom plaster fireplace & walls of glass doors & windows. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. The kitchen is appointed w/ a Thermador dual-fuel range, matching plaster hood, full refrigerator & freezer columns & a large island with seating topped in honed black quartzite. The surrounding cabinetry features hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces line the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balances the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The main floor primary suite is accessed through antique doors that open to a light-filled gallery overlooking the rear courtyard & pool. The primary bath features an extended vanity w/ dual sinks, matte black fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink paired w/ a handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby bedroom suite is marked by an antique door entry. Each guest bedroom features an en-suite bath introduced by a hand-painted tile threshold, complemented by designer lighting, distinctive mirrors & continuous European oak flooring. The rooftop terrace is accessed from the second-floor hallway. The detached casita opens to the pool courtyard through accordion glass doors on two walls & includes a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Other outdoor spaces include 2 garden courtyards, a heated saltwater pool & a newly constructed outdoor kitchen designed to accommodate a built-in grill & Big Green Egg. A spacious gravel courtyard is ideal for dining or relaxing and is enveloped by mature bamboo that creates exceptional privacy. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle within one of Winter Park’s most exclusive enclaves.

1150 Via Salerno, Winter Park

$1,607,160
4 Beds 3 Baths Lake Knowles Terrace SubDv. 32789 Zip Code
An extraordinary home, built in 2018 by Lazarus, is on a quaint cobblestone street in the exclusive Tree Streets of Winter Park. Contemporary transitional design has many details and has been beautifully maintained and upgraded. A four-bedroom, three-bath pool home stretches over 2,800 square feet with natural light filling the spaces through expansive windows. The home offers open concept living in the main gathering room as well as dedicated dining and office/or guest rooms. Fantastic kitchen with custom double cabinetry to the ceiling features an abundance of storage and generous workspace, a large center island with quartz counters, with a stylish waterfall edge and subway glass tile backsplash. Top of the line appliances include Kitchen Aid and Bosch and a Viking 48-inch gas range, microwave drawer and kitchen are rounded out with a butler's pantry/bar area with built-in wine refrigerator that blends the kitchen to dining. Kitchen is open to the living room with a gas fireplace finished with sleek tile extending to ceiling and vaulted ceiling with wood detail all opens to outdoor living under a covered porch with tongue and groove ceiling and sparkling pool. The main level owner’s retreat has two large walk-in closets, and serene bath with double sinks, soaking tub and custom tiled walk-in shower with seamless glass. An additional guest room/study on the first floor has a private bath while upstairs you’ll find two oversized bedrooms and a second bonus/family room. Other details include frosted glass garage door, hardwood pre-engineered wood floors, home recently painted, Phillip Jeffries Wallpaper in dining, designer Restoration Hardware and Pottery Barn Fixtures, professional designed landscaping with architectural outdoor lighting, recessed lighting package, upgraded insulation and energy-efficient tankless water heaters contribute to lower energy bills, 10-foot ceilings, 8-foot doors, custom tile work and beautiful crown moldings. In walking distance to Phelps Park and YMCA, close to hospital, Park Avenue, great shops and restaurants as well as Rollins College. Schools are the best with Lakemont Elementary, Maitland Middle and Winter Park high schools.

1541 Chestnut Avenue, Winter Park

$750,000
2 Beds 2 Baths Osceola Summit SubDv. 32789 Zip Code
Location, location, location! Whether you're ready to build your dream home or simply want to enjoy life in Central Florida’s most prestigious neighborhood at an unbeatable value, this delightful mid-century 2-bedroom, 2-bathroom home offers endless possibilities. Lot size is approximately 130 ft X 78 ft. Perfectly positioned just minutes from Park Avenue, Rollins College, and Lake Osceola, this home places you at the center of luxury Winter Park living—enjoy boutique shopping, fine dining, scenic strolls, or morning paddle boarding just steps from your door. Inside, you'll find a bright and open floor plan filled with natural light and timeless charm. A front den/office with white tile flooring and timeless tongue and groove ceiling offers you space that is not only stylish but functional—ideal for working from home or relaxing with a book. The open living/dining area features stylish wood flooring, large windows, and a ceiling fan for year-round comfort. This unique layout offers 2 primary suites offering plenty of privacy. Head to the fully fenced back yard and concrete patio which provides a private retreat for entertaining or relaxing outdoors. You will find yourself in the heart of it all with close proximity shops, restaurants, schools, universities and major airports. An added hidden bonus is your access to Lake Osceola through 2 parks and walkway ramp, where you can enjoy a beautiful sunset or paddle board/kayak ride. With vintage character, and incredible location with lake access at the end of the street, this Winter Park gem is not to be missed!

311 Cortland Avenue, Winter Park

$1,725,000
5 Beds 5 Baths Kenilworth Shores Sec 06 SubDv. 32789 Zip Code
WINTER PARK FIVE BEDROOM POOL HOME - Discover luxurious living in the heart of Winter Park! Crafted with exquisite attention to detail, this 5-bedroom, 4.5-bathroom pool residence showcases absolute perfection and modern elegance. Built in 2018 by David Weekley Homes, the property boasts a captivating stone façade and a private backyard oasis featuring a saltwater, heated pool and spa with water feature, and ambient lighting — an entertainer’s dream. Inside, soaring ceilings, gleaming wood floors, expansive picture windows, and an abundance of natural light create an inviting and sophisticated atmosphere. The gourmet kitchen is a chef’s paradise, with white maple cabinetry, Quartz countertops, a breakfast island, and stainless-steel gas appliances. The open floor plan seamlessly connects the kitchen, great room, and outdoor living spaces, perfect for hosting friends and family. Located on the first-floor, the spacious primary suite includes a spa-inspired bathroom, while a dedicated home office and guest suite offer comfort and versatility. Upstairs, discover three additional bedrooms, two full bathrooms, and a versatile loft space. Step outside to the wrap-around porch overlooking meticulously landscaped gardens, creating a serene and private outdoor retreat. Located just minutes from Park Avenue, Rollins College, and Advent Health Winter Park, this exceptional residence offers convenient access to top shopping, dining, and cultural attractions. Zoned for the highly sought-after Brookshire School District, this is your chance to experience elevated living in one of Winter Park’s most coveted neighborhoods. Schedule your private showing today and make this exquisite property your new home.

617 Worthington Drive, Winter Park

$439,900
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

$699,000
3 Beds 2 Baths Lakeview Terrace SubDv. 32789 Zip Code
Rare find in Winter Park! This charming one-story pool home offers three bedrooms, two full baths, high ceilings, and an open floor plan—all at an incredible price point. The updated kitchen features gas appliances, a center island, breakfast bar, and a separate beverage fridge. Wood-look tile flooring runs throughout the home for a cohesive, modern feel. The spacious primary suite features French doors that open to a private patio with pool access. The en suite bathroom is oversized, with a large walk-in shower and double vanities. The garage has been temporarily enclosed and is air-conditioned, offering flexible bonus space that can easily be converted back. The home’s nearly 1,700 square feet do not include this additional area. Located just minutes from top-rated Winter Park schools, shopping, and dining. Don’t miss this opportunity!

1891 Bryan Avenue, Winter Park

$675,000
3 Beds 2 Baths Fontainebleau SubDv. 32789 Zip Code
LOCATION! LOCATION! LOCATION! EXPECT TO BE IMPRESSED IN THIS CHARMER LOCATED IN THE HEART OF WINTER PARK! Welcoming you and guests is an attractive curb appeal with walkways and pretty landscaping located on a nicely sized lot all fenced in for privacy. Sit back and relax in this easy, carefree, low maintenance home, desirably located in a peaceful & established community close to major highways. Breathe in some fresh air and walk to Park Avenue known for lots of shopping and delicious restaurants or open your front door & you’re invited into plenty of space to enjoy everyday living & entertaining in this generously sized 3 bedroom, 2 bath pool home offering 1,442 sq. ft. The charming kitchen delivers good looks with an eat in kitchen nook, plenty of storage and access to your outdoor patio made easy for grilling or relaxing. The family room open to the kitchen is light and bright allowing natural light in and creating a cozy atmosphere. Indoor and outdoor space combine perfectly, inviting you to enjoy delightful views and savor Florida living at its very best. Walk through the doors, sit on your enclosed porch, have a glass of wine and listen to the birds. Set on a generously sized homesite, this private backyard is bigger than most, offering a sparkling pool and plenty of room to throw a football & build a swing set. Thoughtfully set far from the busy family area, you'll find a nicely sized master suite with a walk in closet. Extra features include; a newer roof (2022) including new soffits and gutters! A thoughtful layout ensures that everyone will have their own personal space. COME SEE THIS CHARMING HOME LOVINGLY MAINTAINED AND MAKE IT YOURS TODAY!

2190 Temple Drive, Winter Park

$790,000
2 Beds 2 Baths Dixie Terrace SubDv. 32789 Zip Code
The inviting bungalow at 1217 Kenwood Ave is located just a few houses off famed Park Avenue and steps from the Winter Park Village, which is fresh off a $50 million transformation and includes popular bars and restaurants, a movie theater and shopping. The home was fully renovated in 2018 with updates to the HVAC, electrical, plumbing, flooring, subflooring, interiors, and a new roof- offering modern functionality with classic charm. The kitchen features rich navy cabinetry, gold hardware, quartz countertops, a gas range with hood, and a tankless water heater. Since 2021, the home has seen additional upgrades including custom roller shades (shade store), a new sprinkler system, enhanced landscaping with decorative rockwork, paver installation, and fresh sod. Improvements also include new interior and exterior lighting, a porch fan, garage and laundry shelving, and a recently serviced A/C system. The spacious backyard offers room for a pool and is already plumbed for a future outdoor kitchen. Enjoy rear entry access from Denning via a two-car garage. Don’t miss this rare opportunity in one of Winter Park’s most walkable locations!

1217 Kenwood Avenue, Winter Park

$355,000
3 Beds 2 Baths Park Green SubDv. 32789 Zip Code
Charming One-Story Townhome in Prime Winter Park Location! Welcome to this adorable detached 3-bedroom, 2-bath townhome with a spacious 2-car garage, tucked away in the heart of Winter Park (32789). Just minutes from Winter Park Village, Fleming’s, and the boutiques and dining of Park Avenue, this home blends low-maintenance living with unbeatable convenience. Step inside to find a bright, open layout and peace of mind with recent updates, including a new roof (2021), re-piping (2023), and AC system (2016). The single-story design offers ease and comfort, whether you’re looking for a primary residence or a winter retreat. The community features a refreshing pool and clubhouse, and the HOA covers cable and internet—making day-to-day living even easier. Don’t miss this rare opportunity to enjoy the charm and convenience of Winter Park in a move-in-ready home!

1117 Park Green Place, Winter Park

$420,000
3 Beds 2 Baths Howell Heights SubDv. 32789 Zip Code
Beautifully Updated 3 Bedroom, 2 Bath Pool Home in Desirable Winter Park! Welcome to your dream home! This spacious one story gem features 3 bedrooms, 2 full baths, and a private POOL, perfect for enjoying Florida living year round. Step inside to find brand NEW LUXURY VINYL PLANK flooring and FRESH INTERIOR PAINT throughout, giving the home a modern and move-in ready feel. The open layout offers plenty of room to relax or entertain, and the enclosed porch provides a versatile space. The kitchen is a chef's delight with GRANITE countertops and ample cabinet space. Outside, enjoy a large FENCED yard, ideal for pets, play, or gardening. Located in a highly sought after Winter Park neighborhood, this home is just minutes from top-rated schools, shopping, dining, parks, and more. Don't miss this incredible opportunity, schedule your showing today!

2809 Sanbina Street, Winter Park

$2,037,500
5 Beds 5 Baths Conwill Estates SubDv. 32789 Zip Code
Price Reduced to sell. An exceptional custom home by award-winning Davila Homes, perfectly blending modern design and functionality. Located in sought-after Conwill Estates, just minutes from Park Avenue, this 5-bed, 4.5-bath residence features volume ceilings, floor-to-ceiling bronze sliding doors, and a seamless indoor-outdoor living experience. The chef’s kitchen showcases waterfall quartz countertops, Sub-Zero & Wolf appliances, a large island, walk-in pantry, and opens to the living area with phantom screens and views of the resort-style gas-heated pool, fire pit, and a brand-new outdoor kitchen, perfect for entertaining. A first-floor owner’s suite offers pool views, private terrace, motorized shades, spa bath with soaking tub, and expansive shower. Upstairs you'll find 4 en-suite bedrooms, a bonus room with wet bar, wine fridge, 2nd laundry, and balcony overlooking the backyard. Additional upgrades include Summer Kitchen, surround sound, gas fireplace, upstairs & downstairs laundry, private well for irrigation, generator, new HVAC system for downstairs (2025), new water heater (2025), and air-conditioned garage with tiled floors (not included in living SF). This home has been impeccably maintained and is in pristine condition, aluminum roof is a plus. — it truly feels like new. From the moment you step inside, you’ll fall in love with its elegance and charm.

1781 Pine Avenue, Winter Park

$1,595,000
5 Beds 5 Baths Lawndale SubDv. 32789 Zip Code
Experience the charm and elegance of Winter Park living in this beautifully designed 5-bedroom, 4.5-bath home offering 3,267 square feet of thoughtfully crafted space. This residence combines timeless architectural character with modern functionality, From the moment you enter, you’re welcomed by warm natural light, the first floor features an office with an open and inviting layout, and high-quality finishes throughout. Enjoy a spacious kitchen and a generous living and dining area, perfect for entertaining and relaxing, creating a warm and inviting atmosphere. The sliding glass door leads to the refreshing Swimming Pool, Summer Kitchen, a serene retreat for relaxation and entertaining. Following the wooden staircase to the second floor, this home features a spacious primary master suite, offering privacy, convenience, and ease of living. The Pool, the detached two-car garage, and the charming private flex suite are the perfect balance of elegance and comfort. Located just minutes from the heart of Park Avenue Winter Park, downtown Orlando, and fine dining, boutique shopping, museums, and local cafés.

1733 Harmon Avenue, Winter Park

$1,270,000
4 Beds 4 Baths Fontainebleau SubDv. 32789 Zip Code
Seller is including a premium home warranty giving buyers peace of mind with coverage on HVAC, plumbing, appliances & more so you can move in with confidence! Experience the charm and elegance of Winter Park living in this beautifully designed 4-bedroom, 3.5-bath home offering 3,604 square feet of thoughtfully crafted space. Built in 2014, this residence combines timeless architectural character with modern functionality, all nestled on a quiet, tree-lined street in one of Central Florida’s most sought-after neighborhoods. From the moment you enter, you’re welcomed by warm natural light, an open and inviting layout, and high-quality finishes throughout. Enjoy a spacious chef’s kitchen, generous living and dining areas, and a private primary suite perfect for both entertaining and relaxing. The detached two-car garage and charming outdoor space add to the home’s appeal and functionality. This home features a spacious primary master suite located on the first floor, offering privacy, convenience, and ease of living. Located just minutes from the heart of Park Avenue, you’re steps from some of Winter Park’s most beloved spots—fine dining, boutique shopping, museums, and local cafés. Nearby favorites include The Ravenous Pig, Hillstone, Boca, Ava MediterrAegean, and the world-renowned Winter Park Farmers’ Market. With easy access to I-4, 17-92, and Semoran Blvd, commuting to downtown Orlando, Maitland, or the airport is a breeze. Call to set your appointment to view this lovely home!

2401 Lafayette Avenue, Winter Park

$560,000
2 Beds 1 Baths Blk C Pt Rep 02 SubDv. 32789 Zip Code
A rare find in Winter Park: A charming Bungalow with 3-Car Garage (24x36) and detached finished Shed (10x14) for office & or additional Storage! Walking distance to Mead Gardens and the new Seven Oaks Park. Convenient to Rollins College, Park Avenue and Winter Park Village, featuring multiple local eateries and restaurants. Just one mile to Hospital, Science Center and Museum. Easy access to 17/92, I-4 and 408 Expressway. New Roofs (2022), Sewage Pipes Relined (2024), Hot Water Tank (2021) and Home Air Conditioner (2020). Don't miss this hidden gem in beautiful Winter Park, Florida. Submit all offers on "As Is" contract with proof of funds attached. All information is deemed to be correct. Buyer and buyer's agent should verify all prior to submission.

1339 Orchid Avenue, Winter Park

$916,000
3 Beds 3 Baths Kenilworth Shores Sec 06 SubDv. 32789 Zip Code
Nestled in the heart of Winter Park in one of the area’s most sought-after neighborhoods, this professionally designed and fully renovated 3-bedroom, 2.5-bathroom home offers luxurious living with timeless modern style. Step inside to an open-concept layout featuring a gourmet kitchen outfitted with custom cabinetry, stunning quartz countertops, GE Café appliances, a Thermador drawer-style microwave, Brizo faucets, a coordinating pot filler above the stove, and designer light fixtures—perfect for both entertaining and everyday living. Adjacent to the kitchen, a custom wine and coffee bar with floating shelves seamlessly blends style and functionality. For dog lovers the home even includes a whimsical “Doggie Bistro,” complete with its own pot filler, making it a breeze to refill water bowls! This meticulously maintained single-story home offers abundant storage, including generous bedroom closets, attic access, and garage overhead storage. Additional space is available in the backyard shed and the oversized two-car garage with built-in storage. Bathrooms have been completely remodeled with premium finishes, high-end vanities, and designer fixtures that combine elegance and functionality. The powder room near the main living space adds the perfect touch of sophistication and convenience. The front living room features a wood-burning fireplace and a large picture window that fills the space with natural light. Step outside to your private, fully fenced backyard, shaded by a canopy of fragrant jasmine and serenaded by the sounds of local peacocks. With ample space for relaxing or entertaining, the yard also offers a perfect canvas for a future pool. No detail has been overlooked. Recent upgrades include: New roof (2019), new A/C unit (2023), Blow-in insulation, sprinkler system, home water softener, PGT energy-efficient windows (2019), custom pergola with screen, original refinished hardwood floors throughout the main living spaces and bedrooms. Garage auto carpet to create multi-use space. Located just minutes from downtown Winter Park, top-rated schools, award-winning restaurants, scenic parks, and the popular Cady Way Trail, this home offers the best of Central Florida living. With easy access to downtown Orlando, major highways (408, 417, I-4), Disney attractions, and Orlando International Airport. The neighborhood continues to evolve, with many homes being replaced by larger custom homes valued at over $3 million. This is a rare opportunity to own a turn-key home in a highly desirable community!

609 Langholm Drive, Winter Park

$145,000
1 Beds 1 Baths Lakeside Manor Apts Condo SubDv. 32789 Zip Code
Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community for its location and tranquil setting on Lake Killarney. Add to that the brand new air conditioning system (2025), hot water heater (2025) and fresh paint throughout (2025) and you'll see why this unit is for you. Step into the unit through the brand new front door (2025) and you are in the generous living room with dining space. The tidy kitchen with matching all white appliances is clean as a whistle. You'll love the large utility is where you'll find the air conditioner, hot water heater and plenty of shelving. The bathroom has new vanity (2025), mirror and light fixture (2025), and newer toilet. You'll find the bedroom spacious with a large double closet. Ceiling fans in living and bedroom. Location in the community is handy, with assigned parking space just steps away and easy access to the quiet courtyard. You'll love the lakefront outdoor space including pool, club house, tons of manicured green space, over-water covered seating on the new dock, boat launch and slips. Close to shopping and dining in Winter Park, easy access to highways. This community is everything people come to Florida to find!

2500 Lee Road Unit 243, Winter Park

$199,000
2 Beds 1 Baths Aragon Condo SubDv. 32789 Zip Code
Welcome to this beautifully updated second-floor corner unit nestled within the sought-after Aragon Condominium community in the heart of Winter Park. This bright and airy two-bedroom, one-bath home offers a perfect blend of comfort, style, and convenience. Step inside to discover freshly painted interiors and elegant laminate flooring that flows seamlessly throughout the space. The galley-style kitchen offers a functional layout and opens to a spacious living and dining area—ideal for both relaxed evenings at home and entertaining guests. Natural light fills the open-concept living space, while the cozy front patio invites you to enjoy your morning coffee or unwind at the end of the day. Both bedrooms are generously sized with pool view and feature built-in closets for easy organization, while a hallway closet adds extra storage for linens or household essentials. The bathroom features modern finishes and thoughtful design, with a shower and tub. The Aragon community offers a host of amenities designed for easy living, including a tranquil central courtyard, a sparkling community pool, on-site laundry facilities, and ample parking with both assigned and guest spaces. Located in one of Winter Park’s most vibrant neighborhoods, this condo is just steps from shopping centers, grocery stores, restaurants, and retail boutiques. With quick access to I-4 and nearby parks, it offers both a peaceful retreat and a connected urban lifestyle. Whether you’re a first-time buyer, downsizing, or searching for an ideal investment opportunity, this delightful home provides the perfect combination of charm, location, and livability.

851 Miles Avenue Unit 8, Winter Park

$3,020,000
5 Beds 6 Baths Forest Hills SubDv. 32789 Zip Code
Award-winning Phil Kean design on a prominent corner lot in the heart of Winter Park, just minutes from Baldwin Park, Park Avenue, and East End Market—home to Michelin-rated dining and upscale retail. This 5-bed, 5.5-bath residence delivers clean lines, smart design, and seamless indoor-outdoor flow. Recognized with multiple honors, including the 2015 Parade of Homes 1st Place Award for Custom Homes, the American Residential Design Award from the AIBD, and the prestigious 2015 Aurora Awards, this home reflects the highest level of architectural achievement. A retractable Nanowall opens to a private outdoor escape with a heated saltwater pool, summer kitchen, fireplace, motorized screens, and mature bamboo landscape. Two driveways and a freshly laid zoysia lawn add presence to the front approach. Inside, 10’ ceilings and a fluid open plan frame the chef’s kitchen—finished with waterfall quartz, touch-close cabinetry, and Thermador appliances including a steam oven, induction cooktop, and 98-bottle wine cooler. The media room includes surround sound, a motorized screen, and a second retractable wall to the pool. Smart home controls manage lighting, security, Sonos, and cameras with ease. The guest suite offers a Murphy bed and private bath. The primary features a fireplace, spa-style bath, and custom closet. All bedrooms include en-suite baths. Additional highlights: whole-house generator, water filtration, foam insulation, sweep-in vacuum, and an EV-ready garage with custom storage.

1820 Englewood Road, Winter Park

$705,000
3 Beds 2 Baths Charmont SubDv. 32789 Zip Code
Unlock the potential of this charming 3-bedroom, 2-bathroom home—ideal for renovation or building your custom dream residence. Nestled among a mix of beautifully preserved historic homes and stunning new construction, this property is located in one of Central Florida’s most sought-after neighborhoods. The home features classic terracotta tile flooring, two cozy wood-burning fireplaces—one in the inviting living room and another in the spacious primary suite—and a detached workshop perfect for hobbies or additional storage. Enjoy the best of both convenience and lifestyle just minutes from vibrant Park Avenue’s boutiques and restaurants, Downtown Orlando, Baldwin Park, and an array of local parks and recreation. Don’t miss this rare opportunity to create something truly special in the heart of Olde Winter Park!

1840 Laurel Road, Winter Park

$1,000,000
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