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$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

$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

$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

$999,999
4 Beds 3 Baths Timberlane SubDv. 32789 Zip Code
Welcome to 2112 Fosgate Drive, a beautifully updated home nestled on a quiet, tree-lined street in Winter Park. With 4 bedrooms, 3 bathrooms, and just under 2,400 square feet, this residence offers a thoughtful layout with plenty of space to fit your lifestyle. Fully remodeled in 2018, it’s move-in ready with a blend of charm and modern comfort. Step inside and you’ll be welcomed by real hardwood floors and a bright, open floor plan that flows easily from room to room. The kitchen is a true highlight, featuring marble countertops and backsplash, stainless steel appliances—including a double oven—and a separate beverage fridge. It’s perfect for everyday meals or entertaining guests. The home’s three-way split layout offers privacy and flexibility. The spacious owner’s suite includes a fully renovated bathroom and a generous walk-in closet with built-in shelving. A guest en-suite provides an ideal setup for visitors or a home office, while two additional bedrooms share an updated bath and are tucked away for peace and quiet. Out back, you’ll find an oversized backyard anchored by a spacious covered patio with brick pavers and motorized screens—perfect for entertaining or relaxing while little ones play. Additional features include new designer interior doors, plantation shutters, insulated windows, and newer soffits and roof. Ideally located near Blue Jacket Park, East End Market, and zoned for highly rated Audubon K-8 and Winter Park High, this home offers the best of Winter Park living. Don’t miss your chance to make it yours!

2112 Fosgate Drive, 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

$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

$1,175,000
3 Beds 2 Baths College Place Rep SubDv. 32789 Zip Code
Charming 1925 Craftsman with Spanish-Style Guest Apartment in Winter Park's College Quarter. Nestled in the heart of the historic College Quarter, this beautifully preserved 1925 Craftsman home offers timeless character, modern livability, and a rare bonus: a separate Spanish/Moorish-style garage apartment with its own unique architectural flair. The main house features 3 bedrooms, 2 bathrooms, and 1,867 square feet of inviting living space. Classic elements like original heart of pine floors and period finishes can easily blend in well with additional interior updating. Although the house has the history, the flow of the layout works well with today’s modern living and entertaining style. Additionally, just behind the main home, is a 504-square-foot garage apartment which offers a living space, kitchenette, bedroom and bathroom. It has striking interior details, such as hand-hewn pecky cypress beams, heavy plaster work, keyhole shaped doors and hand-wrought ironwork and a cozy fireplace. The apartment space is —a perfect guest retreat, income-producing rental, or private home office. The property also comes with deeded lake access to scenic Lake Virginia, part of the coveted Winter Park Chain of Lakes. The proximity to downtown Winter Park is just a short stroll, through tree-lined brick streets to Park Avenue’s shops and restaurants, as well as Rollins College, which is just a street away. Whether you're seeking historic character, walkable charm, or lakeside living, this unique Winter Park property delivers it all! 4-Point inspection was completed, please see attachments for survey and for home details.

835 Antonette Avenue, 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

$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

$965,000
3 Beds 4 Baths Mondrian/Winter Park Twnhms SubDv. 32789 Zip Code
Don’t miss out on the final new construction unit available - act fast! Discover unparalleled luxury at Mondrian Winter Park, where contemporary design meets the tranquil beauty of Lake Killarney. We are excited to share that this is the LAST corner unit of a highly coveted floor plan in our exclusive community of just 30 modern townhomes along the serene shoreline. Each residence features exquisite finishes, stunning storefront-style windows, and soaring ceilings just shy of 11 feet, allowing natural light to fill the interiors. This brand-new townhome combines contemporary aesthetics with charming brownstone elements, showcasing a unique layout designed for convenience and privacy. The main living space is beautifully situated on the second level, allowing for a seamless flow between the modern kitchen, dining room, and great room. Retreat to the stylish primary bedroom located at the back of the home, where you’ll find a spa-inspired bathroom complete with two walk-in closets, a cozy sitting area, designer tile, a frameless glass shower, and a private water closet—all thoughtfully crafted for ultimate comfort. Our smart split bedroom design includes two additional bedrooms with en suites on the first level, delivering ample space and flexibility for your lifestyle. A full-size laundry room adds to the functionality and elegance of your new home. Step onto the rooftop oasis featuring an outdoor kitchen, a pergola, a hot tub spa, and breathtaking open sky views, creating the perfect setting for relaxation and entertainment. Nestled in picturesque Winter Park, just north of downtown Orlando, residents can enjoy lakeside living with access to a private boat slip, community kayaks, and a beautiful lakefront pavilion. Whether you’re in search of serene relaxation or vibrant entertainment, this prime location offers proximity to top-tier dining, shopping, and recreational amenities for a lifestyle of unmatched convenience and luxury. Seize this incredible opportunity before it’s gone—your dream home on Lake Killarney awaits!

1760 Mondrian Circle, Winter Park

$1,300,000
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
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

$1,825,000
4 Beds 4 Baths Woodmere Terrace Rep SubDv. 32789 Zip Code
A rare gem in the heart of the Vias – Nestled in one of Winter Park’s most sought-after neighborhoods, this beautifully designed home is the epitome of comfort, luxury, and convenience. Located just minutes from Park Avenue, top-rated schools, and the best dining and shopping in Central Florida, this property offers an unbeatable lifestyle in a truly prime location. Inside, the home impresses with an open-concept first floor that’s tailor-made for entertaining. The seamless flow between the spacious living room, dining area, and chef’s kitchen makes it easy to host gatherings of any size—from intimate dinners to lively celebrations. Natural light pours in through large windows, highlighting designer finishes and a thoughtful floor plan that blends elegance with everyday functionality. With four oversized bedrooms and four full bathrooms, there's ample space for everyone to spread out comfortably. The private office on the main level is perfect for working from home, while upstairs, a versatile loft offers flex space that can be used as a playroom, reading nook, or creative studio. The true showstopper is the expansive theater room, offering endless possibilities—use it as a media lounge, game room, fitness center, or whatever your lifestyle demands. Step outside to your resort-inspired backyard oasis, featuring a sparkling pool and spa, lush, professionally landscaped grounds, and a covered patio that’s perfect for summer BBQs and year-round outdoor living. Whether you're relaxing with family or entertaining guests, this outdoor space delivers the feel of a luxury getaway right at home. Don’t miss your chance to own a home that offers exceptional space, stylish design, and one of the most desirable locations in Winter Park.

1665 Temple Drive, Winter Park

$1,825,000
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

$1,335,000
3 Beds 3 Baths Lyman Ave Villas 1 SubDv. 32789 Zip Code
Presenting a stunning and fully furnished END UNIT Townhome, one block off Park Ave! This is 1 of only 8 townhomes built in 2014 by David Weekly, and the only one on the market with incredible Florida outdoor living space. This unit is a gem, with the most privacy and largest side yard of all 8. The location is AMAZING, you can see Park Avenue from your front porch! SO many upgrades, you won't need to do a thing but move in and enjoy walking up to your favorite stores, restaurants, and of course the famous Winter Park Farmer's Market on Saturday mornings! Nothing has been overlooked in this gorgeous residence, so let's take a tour! Entering through the solid wood door, you are greeted with beautiful wood floors and custom window shutters. To your left is a bedroom and/or office with an easy access en-suite full bathroom. Down the hall your eye will be drawn to the breathtaking kitchen with an oversized island, high-end 42" white cabinets with a coffee rubbed stain, GE Monogram appliances, including a natural gas range, and a cozy place for your coffee bar! Looking further you will find the large dining area with a gorgeous crystal chandelier with matching pendants lights over the island. The side bar area pulls your eye into the new custom-built backlit wine room under the stairs! The open concept space invites you into the living room with plenty of room for friends and family to gather. Heading up the stairs you will find a custom-built bookcase before entering into the primary suite. There is so much natural light flowing through the windows from the southern and eastern exposure of this cozy corner bedroom. The primary bathroom has double sinks and a private water closet. Next, we come to the custom-built laundry room, with storage cabinets for days! Coming out of the laundry room we find the 3rd bedroom in the home, a quiet room tucked away for children or guests, and this also has a full bathroom including a comfy tub. Now let's head back downstairs and step out to the OVER 1300 SQ FT OF FENCED-IN FRONT AND BACK OUTDOOR LIVING SPACE! The builder definitely took all of your outdoor needs into consideration when designing this space. The covered brick paver patio with an electric screen boasts a built-in summer kitchen with a gas grill, granite countertops, a wet sink, and storage. There is also a mounted TV on the wall to watch your favorite teams play this fall! Out in the yard is recently installed pet-friendly artificial turf and an area for cornhole or Bocce ball, all inside a fully-fenced yard! The 2-car garage behind the home is accessed by a secured gated entrance. The garage floor has been fitted with custom SwissTrax tiles. Up above the garage is a floored and insulated 200 sq foot storage room that is large enough to stand up and walk around in, and this is climate controlled with a new (2023) mini-split AC (no more need for that expensive storage unit for the Christmas decorations)! Other features include interior paint (2024), new carpet and ceiling fans (2024), new SONOS system, new cabinet hardware, an upgraded whole house security system with cameras, a new (2024) tankless on-demand hot water heater, new (2023) LG washer and dryer, and upgraded landscaping with new uplighting and Mexican stones. The HOA fees cover building insurance, landscaping, watering, pest control with termite bond, roof and gate maintenance. This nearly new townhome right next to Park Avenue is more than just a home, it's a lifestyle!

242 W Lyman Avenue, Winter Park

$2,285,000
4 Beds 5 Baths Kenilworth Shores Sec 02 SubDv. 32789 Zip Code
An elegant and well-kept home located in a quiet neighborhood next to Windsong. It combines a cozy interior design with functionality and light-filled open floor plans. Energy-saving features include double-panel windows with Low-E coating, foam-injected block walls, insulated interior walls and floors, tankless water heaters, tile roof, and a paver driveway. The first floor ceilings peak at 12 feet, delivering a voluminous feel to the living areas and primary rooms; while upstairs, an equally impressive height of 10 feet is maintained throughout the second floor, accommodating bedrooms, making them cosy and comfortable retreats. Making the house great for entertaining are two 10' tall disappearing sliding glass walls in the Great Room that connect indoors and outdoors seamlessly. The kitchen includes a Thermador pro stainless steel appliance package enhanced by granite countertops, custom-made & finished cabinets along with an outdoor kitchen on the lanai equipped with a built-in grill & linear fireplace, and a pool with deck and pergola, all contributing towards luxurious alfresco dining. The clever layout of this property consists of both master & guest suites along with study/office space on the first floor, while there are an extra 2 bedroom suites plus a bonus/media room upstairs, enhancing its versatility. This confluence of style makes this home both luxurious as well as eco-friendly. This property brilliantly integrates cosmopolitan living while retaining the warmth of home at every corner.

521 S Phelps Avenue, Winter Park

$2,500,000
4 Beds 5 Baths Sylvan Lake Shores SubDv. 32789 Zip Code
Under Construction. Brand-new, meticulously crafted residence built by renowned builder LUIH Homes offering 3,138 square feet of thoughtfully designed living space. As you arrive, the home's stunning architectural façade and detached two-car garage make a striking first impression. Inside, every detail has been carefully curated to offer both sophistication and functionality. Soaring ceilings and expansive windows flood the home with natural light, while engineered hardwood flooring and elegant designer lighting add warmth and refinement throughout. The heart of the home is an impressive open-concept living area anchored by a chef’s kitchen featuring custom cabinetry, quartz countertops, top-of-the line Thermador appliances, a walk-in pantry, and an oversized center island. The adjacent dining and living spaces offer seamless flow, highlighted by stunning finishes and built-in features that enhance both comfort and convenience. The luxurious primary suite features a spa-like ensuite bath featuring a freestanding soaking tub, oversized glass-enclosed shower, dual vanities with quartz countertops, and a large walk-in closet. Secondary bedrooms are equally spacious, with ample closet space and access to beautifully appointed bathrooms with premium fixtures and finishes. Step outside to a private backyard oasis offering a large, covered patio with a summer kitchen, a sparkling pool, and a spacious backyard. The detached garage provides added flexibility, ideal for vehicle storage, a workshop, or potential future guest house. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park features. Schedule your private showing today and experience the epitome of luxury Winter Park living.

185 Sylvan Boulevard, Winter Park

$1,650,000
4 Beds 6 Baths Fontainebleau SubDv. 32789 Zip Code
This Beautiful Winter Park Home is located between the "Vias" and "Tree Streets" for convenient access to highly coveted schools, Interlachen Country Club, Winter Park Racquet Club, YMCA and everything you love about Winter Park. Spacious and well proportioned rooms distinguish this beautiful home through its balance of both large, open spaces for casual indoor/outdoor entertaining and more formal spaces for living and dining. The large great room with stacking sliding doors flows to the adjacent screened lanai and pool area complete with "Summer Kitchen" and motorized retractable screens. Also open to the great room you'll find a well appointed kitchen complete with solid wood cabinetry, quartz counter tops, stainless double wall ovens, drawer microwave, glass cooktop with exhaust hood, dishwasher and french door refrigerator. Extending the kitchen, and adjacent to the great room, is a complete bar area with wine refrigerator, beverage refrigerator, storage and plenty of space for casual seating or eating. To keep everything in its place, there is a conveniently located "mud room/drop zone" adjacent to the kitchen. Turning to the more formal spaces on the ground level, you'll find a large entry foyer flanked by living and dining rooms. Off the entry hall is a lovely half bath/powder room and a full en-suite second primary bedroom with a full bath that opens to the pool area. Upstairs you find a large loft area from which you access the bedroom suites, laundry room and bonus room. The Primary Suite is spacious and private with an large walk-in closet and en-suite bathroom offering a garden tub, walk-in shower, private water closet and split vanities. Bedroom #3 is en-suite with a walk-in closet and tub/shower. Bedroom #4 offers a walk-in closet and an en-suite bathroom complete with walk-in shower. Upstairs you'll also enjoy the convenience of a spacious laundry room with utility sink, cabinetry, laundry bins and space to fold and hang as needed. As if that's not enough, there is a bonus room complete with half bath and closet that makes a fantastic workout space, home office or 5th bedroom. Outside you'll enjoy the large screened lanai and pool area that opens to the backyard. The backyard is complete with low maintenance artificial turf that provides year round green space. Your kids will be the envy of the neighborhood with the custom "tree house" retreat - allowing them a safe and secure escape for exploring their imagination and creativity. Large Two Car Garage. Privacy Driveway Gate. Roof new in 2023. A/C new in 2023. Water Heater new in 2023. Pool new in 2020. All measurements are approximate and Buyer is responsible to verify dimensions.

2339 Lafayette Avenue, Winter Park

$434,000
2 Beds 3 Baths Quarters At Winter Park Condo SubDv. 32789 Zip Code
Welcome to 1122 Washington Avenue – a delightful 2-bedroom, 2.5-bath townhome located in one of Winter Park’s most desirable neighborhoods. Just a short stroll to Park Avenue, Rollins College, the Winter Park Tennis Center, and the brand-new Seven Oaks Park, this home offers the perfect blend of lifestyle and location. This area is undergoing tremendous transformation, especially along the revitalized Orange Avenue corridor, with exciting new shops, galleries, restaurants, and community spaces opening regularly. It’s a rare opportunity to live in a neighborhood that blends established charm with vibrant new growth. The home has been freshly painted and offers a bright, clean interior that’s ready for your personal touch. With tons of potential for upgrades and customization, you can truly make this space your own. Both bedrooms feature en-suite baths, and the open living area offers great flow for entertaining. A 2-car garage with driveway provides valuable convenience and storage. Enjoy low-maintenance living in a location that continues to grow in value and appeal. Whether you’re looking for a primary residence, a lock-and-leave second home, or an investment in the future of Winter Park, this is an opportunity you won’t want to miss.

1122 Washington Avenue Unit 7, Winter Park

$2,100,000
4 Beds 3 Baths Cortland Park SubDv. 32789 Zip Code
Commanding an elevated position with tranquil views of Lake Mizell, this quintessential 1926 estate artfully fuses period elegance with refined, modern enhancements. Moments from the boutiques and restaurants of Park Avenue, the residence welcomes with a paver circular drive and a private, gated side entry leading to a detached two-car garage. A brick-clad front porch and mature landscaping frame the formal entry, setting a tone of architectural distinction. Inside, a gallery-style foyer showcases designer wallpaper and salvaged pew rail detailing from a New York City church. The formal living room offers a stately gas fireplace, bespoke built-ins, and a large fixed window framing the lake, ideally suited for a quiet reading nook. The adjacent sunroom, encased in fixed glass, captures the surrounding canopy and lake vistas in all seasons. A generous dining room with custom dry bar, underlit floating shelving, and beverage refrigeration provides an ideal setting for elegant entertaining. The gourmet kitchen is thoughtfully appointed with paneled appliances including refrigerator and freezer columns, refrigerator drawers and a microwave drawer. Additional features include natural gas cooking, double ovens, and a sun-drenched breakfast room opening to the rear terrace and lap pool. A Dutch door entry offers functional access for daily living, while the basement below presents an opportunity for climate-controlled wine storage. The upstairs primary suite exudes comfort and sophistication with its gas fireplace, walk-in closet illuminated by a lake-facing window, a private covered balcony, and a spa-inspired bath with dual vanities, soaking tub, steam shower and private water closet. Two additional guest rooms with a Jack and Jill bath complete the upper level. Extensive renovations include a newer roof, Andersen windows and doors, two HVAC systems, full re-piping and rewiring, fresh paint, lighting, a newly installed pool heater and Hardie board siding—all executed within the last five years. The walk-up attic and pristine basement offer rare additional storage. Refinished hardwood floors throughout provide a consistent, elegant backdrop. This residence is a compelling blend of character, craftsmanship and contemporary living.

104 Cortland Avenue, Winter Park

$995,000
4 Beds 3 Baths V H Musselwhites Sub SubDv. 32789 Zip Code
WELCOME to 1821 WINDSOR DR in WINTER PARK, FLORIDA! This is a ONCE IN A LIFETIME OPPORTUNITY to own this BEAUTIFUL CUSTOM-BUILT MASTERPIECE of a HOME in ONE OF THE MOST DESIRED LOCATIONS in TOWN! When you buy this Home, you aren’t just purchasing a NEWLY BUILT CUSTOM HOME FULL OF LUXURIOUS UPGRADES and ARCHITECTURAL FEATURES; you are also buying into the LIFESTYLE that others DREAM OF LIVING in the LAKEMONT AREA of WINTER PARK! The A RATED LAKEMONT ELEMENTARY SCHOOL is just beyond your backyard! Phelps Park is also only ¼ mile away! The INFAMOUS PARK AVE is LESS THAN A MILE AND A HALF AWAY. There are over 175 LOCAL SHOPPES and RESTAURANTS in the immediate area of PARK AVE, mixed in with NUMEROUS PARKS AND GREEN SPACE! The RENOWNED ROLLINS COLLEGE is also LESS THAN A MILE AND A HALF AWAY! You will LIVE, WORK and PLAY in the MIDDLE of THE PLACE TO BE in TOWN! YOU CANNOT PICK A BETTER LOCATION to LIVE IN if you are wanting the WINTER PARK LIFESTYLE! The Home itself was Built in 2017! The CURRENT OWNERS are the ORIGINAL OWNERS and have IMMACULATELY MAINTAINED THIS HOME! This Home has a STATE-OF-THE-ART PHOTOVOLTAIC SOLAR SYSTEM that is PAID OFF and WILL CONVEY WITH THE HOUSE so the NEW OWNER WILL HAVE MINIMAL POWER COSTS and TOP OF THE LINE SOLAR ENERGY! Structural Upgrades that are above and beyond are: Architectural Features such as the Roof Shape and the Design of the Exterior Walls that are meant to withstand the strongest of hurricane winds. The home is also built up on one extra layer of Cinderblock to avoid any flooding risk! You will notice as soon as you pull up to the house, there is a BEAUTIFUL CURB APPEAL that is emphasized by the mature, but low maintenance landscaping. Walking into the house, your attention is immediately drawn to the BEAUTIFUL WOOD LOOK PORCELAIN TILE that is THROUGHOUT THE ENTIRE MAIN LIVING AREA and BEDROOMS! The house opens up into a very large and modern floor plan! The Main Living Area is a very large area that includes the Living/Family Room, an Oversized Gourmet Kitchen and a nice sized dining room! This entire space is punctuated by lots of perfectly placed windows for tons of natural light, warmth and comfort! The Kitchen has High-End Quartzite Countertops, an oversized island and Custom Walnut Soft-Close Cabinets! Stainless Steel Appliances, recess lighting and under cabinet lights top off what is already a DREAM KITCHEN! The PRIMARY SUITE is OVERSIZED with large windows and lots of space! The Primary Bathroom is the size of a Primary Bathroom you would expect in a home of twice its size! There is a HUGE OVERSIZED CUSTOM SHOWER with MULTIPLE SHOWER HEADS include a RAIN SHOWER HEAD and enough space for you and your significant other to comfortably shower at the same time! There is also an elegant garden tub if you prefer to bathe in relaxation! Lots of floor space, lots of counter space and well-designed dual vanities make the primary bathroom feel like its own little slice of heaven! There is also a very large, custom closet that has built-in “his & her” shelving. All secondary bedrooms are also a very healthy size!! Out back, you can enjoy the birds, plants and the nice Florida weather on your covered lanai that is over 250 square feet and has an OUTDOOR KITCHEN with a built-in refrigerator, and a built-in grill! Many species of plants in the natural backyard attract all sorts of birds to your home as well! Don't Miss This Opportunity! It's a One-of-a-Kind Home! Book your appointment today!

1821 Windsor Drive, Winter Park

$480,000
3 Beds 3 Baths Indiana Place Condo SubDv. 32789 Zip Code
Tucked away on a quiet street blocks from the cultural heartbeat of Winter Park is this 3-bedroom, 2.5-bath townhouse-style condo that offers a balance of comfort, convenience, and charm. With nearly 1,600 square feet of thoughtful space, the two-story home lives large, featuring an open-concept main floor with high ceilings, ceramic tile throughout, a spacious kitchen with granite counters and pantry, and a cozy living area complete with fireplace, built-ins—perfect for stashing your favorite reads, and French doors that provide natural light and flow out to your private patio. Upstairs, the spacious primary suite features a walk-out balcony, updated bathroom with an elegant shower, dual sinks, and a large walk-in closet, while two additional bedrooms give you flexibility for guests, family, or even a quiet home office. Recent updates like brand-new carpet, a 2018 A/C system, and a 2025 water heater offer peace of mind, and the attached two-car garage adds that rare, practical bonus. But what really makes this spot sing is its unbeatable location—you're less than two miles mile from Park Avenue’s boutiques and brunch spots, a quick ride to Rollins College, and just minutes to Mead Gardens, Leu Gardens, the Orlando Science Center, Winter Park Village, AdventHealth Hospital, College Park, I-4, and the SunRail Station for an easy commute downtown. Whether you're strolling to the Saturday Farmers' Market or grabbing coffee before class at Rollins, this place lets you be in the middle of it all—without sacrificing space or comfort. HOA fees are low, leasing is allowed, and pets are welcome. It’s easy living in one of Central Florida’s most beloved neighborhoods—where everything just feels...right.

1545 Indiana Avenue Unit B, Winter Park

$2,495,000
4 Beds 5 Baths Robert Dhu Macdonald Park SubDv. 32789 Zip Code
Now offered at $2,495,000—an outstanding value for a thoughtfully designed pool home on a spacious lot in Winter Park’s most sought after neighborhoods. Located in the heart of the “Golden Triangle”—the core residential district just a short walk from Park Avenue’s world-class shopping and dining—940 Lincoln Circle is a beautifully renovated West Indies/Key West-style home that blends architectural charm, comfortable elegance, and thoughtful functionality on an oversized .33-acre lot. With 4 bedrooms and 4.5 bathrooms across 3,551 square feet, this home lives primarily as a one-story layout, enhanced by a private upstairs suite with bedroom, full bath, and bonus room—accessible from both inside and a separate outdoor entry. Ideal for multigenerational living, guests, or private work/living quarters, this flexible plan is rarely available in such a prime location. A gated front porch and covered entry open into the foyer and an expansive formal living room with vaulted wood-paneled ceilings and gas fireplace. The space flows easily into the dining area and kitchen, which overlook the screened porch and backyard oasis. The kitchen is appointed with marble countertops, custom cabinetry, gas cooktop, cabinet-paneled Sub-Zero refrigerator/freezer, double ovens, and a walk-in pantry. A custom wine room—perfect for entertaining—sits just off the main living space. A nearby den (or optional fourth bedroom with closet) is paired with a bright enclosed Florida room currently used as a home office with rose garden views. This wing connects to a full bath and a secondary bedroom at the front of the home. A stylish powder bath is conveniently tucked away for guests. The private primary suite is positioned at the rear of the property and features a soft entry, dual custom closets, outdoor access, and a beautifully appointed bathroom with dual vanities, glass-enclosed shower, soaking tub, and private water closet. Upstairs, a second guest suite with bonus/flex room and full bath is ideal for visitors, a gym, or studio. At the rear of the home, a welcoming family room with fireplace opens to the covered lanai and kitchen, offering ideal indoor-outdoor flow. The backyard is a fully fenced retreat with lush landscaping, renovated saltwater pool with new equipment, and mature trees surrounding multiple hardscape patios and garden paths. A well-appointed full bathroom with exterior access off the screened patio offers convenient functionality for pool use, gardening, or even dog washing—enhancing the home’s seamless indoor-outdoor lifestyle. The outdoor kitchen includes a Blaze grill, Fire Magic refrigerator, Blackstone griddle, stainless sink, storage cabinetry, and vent hood—creating a true resort-style environment. The oversized two-car garage features epoxy floors, built-in storage, and space for larger vehicles. Additional highlights include two Rinnai tankless water heaters, 2024 Trane condenser, 2019 Mitsubishi mini-split, full-house Generac generator with transfer switch, motorized shades by The Shade Store, and a well-appointed laundry room with built-in cabinetry, utility sink, and yard access. A rare opportunity in Winter Park’s most walkable and desirable neighborhood.

940 Lincoln Circle, Winter Park

$4,599,000
5 Beds 7 Baths Robert Dhu Macdonald Park SubDv. 32789 Zip Code
Welcome to Lincoln! This new construction single family home has been meticulously crafted and constructed by Wooten Built, a locally established, award-winning developer and luxury home Builder. Location! Location! Location! Lincoln Circle is a quiet street next to Park Avenue restaurants and shopping. Easily walk to Winter Park shops, restaurants, and the Winter Park Golf Course. This bespoke home includes premium features, appliances, fixtures and finishes as follows: Elevator, Wolf/Sub-Zero appliances, wine cooler tower, built-in coffee maker, Lutron RA3 Automation, wired for security with plenty of camera drops, whole-house audio pre-wire featuring Sonos speakers and 5.1 surround, first floor primary bedroom with ensuite washer/dryer, additional guest suite first floor, 11’4” first floor ceilings and custom 10’ solid core DOORS, wet bar, large vaulted upstairs living room, large flex-space upstairs bonus room, trey ceilings, huge front entry window and door system, two 10’x10’ full-view garage doors, circular driveway, full-house natural gas generator, heated pool with spa and fire & water bowls, plenty of pool deck space, and exquisite landscaping. Smart glass covers the large ~14’ x 10’ front entry system… Choose frosted for privacy or transparent/thru-view at the press of a button! A 6’ masonry-stucco wall encompasses the property. The rear cabana/pergola houses the summer kitchen, pool bar, pool-bath and outdoor shower. Enjoy two fireplaces!: a 100” linear electric fireplace in living room and a 60” linear natural gas fireplace by the pool deck. Inquire with agent for more information.

985 Lincoln Circle, Winter Park