Winter Park Real Estate, Homes and Condos for sale

All Winter Park homes currently listed for sale in Winter Park as of 07/22/2019 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Winter Park homes for sale or other Winter Park real estate, please contact us and one of our knowledgeable Winter Park REALTORS® would be pleased to assist you.


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$6,500,000
1360 ALABAMA DR, Winter Park FL 32789
7
BEDS
11
BATHS
10,600
SQFT
$613
$/SQFT
1.04
ACRES
2009
BUILT
"Stunning Mediterranean Lakefront Estate. Across from the secret gardens of Kraft Azalea Park sits this palatial 1-acre estate with over 10,000 SF of luxurious living space, private tennis court, resort-style pool, and more! Offering formal living areas, gourmet chef s kitchen, open great room, his and her home offices, elevator, 12-person home theater, billiard room, and six guest suites, each with a private en suite, and a separate guest apartment with kitchen, this home leaves nothing to be desired. Detailed with high-end finishes throughout, the home is exquisite in every way. Polished travertine and hardwood flooring, trim moldings, wrought-iron railings, 27 ceilings, and a whole-house entertainment system are just a few of the custom details that have been installed throughout the home. Walkout balconies off the front and rear of the home take full advantage of the home s picturesque surroundings. The nearly 1,000 SF second floor lanai overlooks the pool and tennis courts and the attached 4-car garage, a rare and highly desirable find, along with the front circular drive provide a sophisticated entry for visiting guests. Private boathouse on Lake Maitland faces westward and offers gorgeous sunset views and convenient access to Winter Park s main attraction the Chain of Lakes. Located on one of the most prestigious drives in town, this extraordinary home is like no other and is just a short walking distance from the award-winning restaurants and boutique shops along Park Avenue."
* LISTED OVER 120 DAYS 
$5,500,000
1731 PINETREE RD, Winter Park FL 32789
6
BEDS
8
BATHS
7,654
SQFT
$719
$/SQFT
0.68
ACRES
2014
BUILT
"Luxurious Lakefront Living. Enjoy gorgeous sunsets on Lake Maitland from this luxury estate in Winter Park's exclusive Via's neighborhood next to the Isle of Sicily. No details were spared in this custom-designed 7654 sq ft, 6-bedroom, 7.5-bath home, which features an in-law suite with full kitchen and bath, laundry rooms on both the first and second floors, a game room, den, office and elevator. Perfect for entertaining and waterfront living, the lake side features an outdoor bar, saltwater spa and swimming pool, fire pit, fountains and full electric boathouse with bath. A huge, sit-in pantry, butlers sink and indoor bar area are adjacent to a large open kitchen featuring center island seating and commercial-grade ovens and other appliances. Bask in the best of Winter Park living in this spectacular, 7,654 sq. ft. beauty."
* NEW LISTING 
$5,200,000
1128 PRESERVE POINT DR, Winter Park FL 32789
4
BEDS
5
BATHS
6,179
SQFT
$842
$/SQFT
2.09
ACRES
2012
BUILT
"Located on pristine Lake Berry in the famed Windsong Community, this privately gated contemporary estate is set amid mature oaks and lush landscaping. Situated on over 2 acres and on one of the largest lots in Windsong. The home is designed by award-winning Nasrallah Design Group and Interiors by Award winning Steven G of South Florida. With over 6k sq. ft of living space, this is one of the largest single-story homes in Winter Park. The elaborate floor plan opens to formal areas featuring solid white oak flooring, detailed lighting and ceiling details throughout. The gourmet kitchen has top-of-the-line appliances and has a hidden pantry. There is an abundance of natural light and lake views from almost every room.10-ft sliding doors throughout the home lead to the extensive covered lanai that is equipped with retractable screens and an exceptional outdoor space that includes a sparkling 82x12 lap pool and spa. The master bedroom boasts a beautiful sitting area that overlooks the pool and spa. The master bath features a steam shower and three separate walk-in closets. The remaining guest rooms have ensuite bathrooms, beautiful views and large closets. Some of the other extraordinary features of the home include: full house generator, Lutron lighting, complete audio system, fire sprinkler throughout with concealed heads, summer kitchen, a fully gated electronic motorized gate for entry and much more! Although the home was completed in 2012 it has barely been lived in, looks and feels like a brand new home."
$4,795,000
1941 LEGION DR, Winter Park FL 32789
5
BEDS
7
BATHS
9,692
SQFT
$495
$/SQFT
2.38
ACRES
2008
BUILT
"One of kind Zachary Kauffman masterpiece on 1+acre on Lake Maitland now available. With his renowned attention to quality & detail, this 5+bed/5+bath has timeless traditional features + every modern amenity you can dream of. Thoughtfully designed w/stunning lake views from every room; Grand foyer welcomes to formal LR w/2 sided FP adjoining cozy Library, both w/custom millwork. East Wing is for FUN; Sports Room & Bar, w/5 TVs, impressive granite bar. Mirrored Exercise Studio, 6 seat Theatre. West Wing: Formal DR, Butler s Pantry w/wine frig to huge open Kitchen & FR. Gourmet stainless Dacor package; convection gas oven/range, microwave & warming drawers; Bosch DW, Thermador frig & freezer. Custom cabinetry, huge granite island, walk in pantry. Great entertaining space w/gorgeous view, walk out to lanai. Lux Master w/massive balcony, FP, coffee bar, Spa bath w/soaking tub, w/c + bidet, his/hers custom closets. 2nd level East Wing: 3 BRs ensuite w/walk ins + balconies; double desk, 2nd utility rm, loft w/charming shiplap, private office. South Wing: entry from motor court, 2 car gar, Home Office, Mudroom/drop zone, Utility w/craft bar, BR en suite, PLUS Bonus Studio w/kitchenette. Addl detached 3 car gar, 800 sq/ft 1/1 Guest Apt. Outdoor is private Florida oasis: huge paver lanai overlooks lake, Cypress trees, saltwater pool w/spa & beach. Gazebo w/Dacor grill, frig & FP. Covered Boathouse w/lift for sport boat + 2 jet skis; lg dock area for fishing & daydreaming. Full Feature list provided on request."
* LISTED OVER 120 DAYS 
$4,300,000
935 GREENTREE DR, Winter Park FL 32789
4
BEDS
5
BATHS
4,975
SQFT
$864
$/SQFT
0.62
ACRES
2006
BUILT
"Exquisite inside and out! This magnificent Georgian-style estate home was meticulously constructed by Posada Custom Homes and is located in one of Winter Park's most desirable neighborhoods offering all the allure of fine lakefront living and just minutes from Park Avenue s popular shopping, dining and cultural gems. Situated on a secluded lot this residence enjoys a picture-perfect setting and views with 105 feet of shoreline overlooking the north shore of Lake Osceola part of the Winter Park chain of lakes. Superior craftsmanship and attention to architectural detail emanate throughout the 4,975 SqFt of living space. This impressive property features an inspired layout starting with the exquisitely designed public spaces and continues throughout the rest of the home. The spacious owner s retreat features a balcony overlooking the lake, customized walk-in closets, morning bar, gas fireplace and bath with luxurious fixtures and finishes. Two additional oversized ensuite bedrooms open onto a balcony and a third floor game room offers the perfect hideaway. Additional amenities include an elegantly appointed formal living room, dining room with butler's pantry, family room with fireplace and adjacent wet bar, gourmet kitchen with custom cabinetry and top of the line appliances, coffered ceilings, extensive custom woodwork and built-in cabinetry, stone and hardwood flooring, slate roof, copper gutters, elevator, salt water pool/spa, boat dock, summer kitchen, whole house generator, and a three-car garage."
* LISTED OVER 120 DAYS 
$3,995,000
1013 TEMPLE GRV, Winter Park FL 32789
5
BEDS
6
BATHS
5,797
SQFT
$689
$/SQFT
0.69
ACRES
1979
BUILT
"Beautiful home on Winter Park Chain of Lakes. Stunning estate on Lake Osceola with long private driveway to home that has gorgeous views of pool, gardens and lake. This one of a kind property has it all; privacy and charm in a fantastic Winter Park location. Large living room with lake views, fireplace and bay window. Large gourmet kitchen with top of the line appliances and eat in area overlooking pool and terrace down to the lake. Master bedroom has dramatic vaulted ceilings and cozy fireplace. Call for more information or to arrange a private showing of this beautiful Winter Park Lakefront Home."
* LISTED OVER 120 DAYS 
$3,895,000
375 VIRGINIA DR, Winter Park FL 32789
5
BEDS
5
BATHS
7,538
SQFT
$517
$/SQFT
1.32
ACRES
2004
BUILT
"Lakefront, Location, Luxury. Move right into this beautiful lakefront custom home on cul-de-sac with views of Rollins College. Located on desirable Lake Virginia. 5 bedroom, 4.5 bath with wine room, bonus room, office, media room, exercise room, and bright second floor Florida room with lake views as well. Large Master with expansive balcony for perfect sunset views on the lake. Gourmet kitchen with large eat in granite counter sitting area that opens onto family room and out to covered rear patio and outdoor grill station. Absolutely perfect for entertaining inside and out! Home has 2 master suites for first and second story living. Built-ins and architectural detail throughout add to the quality and value of this one of a kind Winter Park home. Spacious second story bunk room ideal for guests adjacent to bonus/game room. Thoughtfully designed split floor plan with so many extras you will love. Call for private viewing. Buyer to verify measurements."
$3,495,000
1400 GREEN COVE RD, Winter Park FL 32789
5
BEDS
7
BATHS
6,384
SQFT
$547
$/SQFT
0.70
ACRES
1995
BUILT
"Timeless, classic, sophisticated, and exceedingly peaceful A once in a lifetime opportunity to live in a premier Winter Park Chain of Lakes estate home on almost an acre, walking distance to downtown Park Avenue. This one-owner custom home was designed by esteemed architect Steve Feller and expertly built by Don Jernigan with high quality workmanship and thoughtful detail throughout. Enter into a grand foyer with sweeping staircase, overlooking the formal living room s two story wall of windows showcasing beautiful Lake Maitland. The first floor has large and accommodating spaces, all with lake views, perfect for entertaining with a separate living room, formal dining room, & family room adjacent to the kitchen. The kitchen was updated with all white cabinets, a beadboard island, stainless appliances, granite countertops, double ovens, a breakfast bar and large eating nook with abundant windows conveying brightness and light. There is also a 1st floor bedroom suite and an elegant, traditional home office with paneled walls. The 2nd floor has a master bedroom suite with large bathroom and huge walk-in closet, as well as 3 additional bedroom suites, a bonus loft, & media room with bar area. Features include fireplaces, crown molding, hardwood floors, French doors, coffered ceilings, built-ins, and lots of storage. Appx 119 of lake frontage, perfectly manicured lawn, boat house & dock (as is), 2 car garage with capability to add 3rd, and zoned for Dommerich, Maitland Middle, and WPHS."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,675,000 TO $3,495,000 
$3,395,000
125 S INTERLACHEN AVE #6, Winter Park FL 32789
3
BEDS
5
BATHS
4,160
SQFT
$816
$/SQFT
0.35
ACRES
2016
BUILT
"Under Construction. Completion by July. Only two residences remain. Your opportunity to own unprecedented luxury in the most exclusive area of Winter Park has arrived. South Interlachen Place is around the corner from world famous Park Avenue, across the street from the Alfond Inn and just a stone s throw from the Winter Park Chain of Lakes. Comprised of six exquisitely appointed townhouses, South Interlachen Place is being built with premium level specifications; a standard of luxury usually only found in world-class destinations. The project was designed by award-winning architect Randall Slocum of Slocum Platts. Privacy is the top priority: every fee-simple residence includes a private two-car garage, private elevator to all levels and lush, mature landscaping defining the entrances. A truly unique aspect of the design is the extraordinarily large and private rooftop terrace for each individual residence, providing both covered and open areas for outdoor dining and entertaining. Each private rooftop terrace comes with a fireplace and powder bath. The residences are designed with age in place features throughout, allowing for the adaptation of changing lifestyles. Each townhouse embraces smart technology for entertainment, lighting, energy management and security. Live in one of the most extraordinary residences in a truly exceptional Winter Park location at South Interlachen Place."
* LISTED OVER 120 DAYS  * PRICE INCREASED - $3,160,000 TO $3,395,000 
$3,300,000
, Winter Park FL 32789
4
BEDS
5
BATHS
5,095
SQFT
$648
$/SQFT
0.63
ACRES
1954
BUILT
"Winter Park Chain of Lakes! Amazing opportunity to own this custom-built home with 110 feet of frontage on beautiful Lake Osceola! You will love coming home to this open-concept single-story home, totally renovated in 2016, with bleached oak floors throughout. Panoramic water views are yours from almost every room in the house, which features a 500-bottle temperature-controlled wine room with glass walls off the living room; a spacious dining room; and chef s kitchen with two large Calcutta marble islands, all new stainless steel Thermador appliances, custom soft-close inset cabinets with glass fronts, and custom pullouts. This 5100-square-foot home boasts 4 bedrooms, 3 full & 2 half baths, an office, family room, and two wood-burning fireplaces. This home has too many amazing features to list custom everything! Outdoors, enjoy the tiered back yard with Signature landscaping; heated pool with cabana; 22 x 28 sport court; boat house, dock, and electric boat lift, all overlooking the sparkling blue water of Lake Osceola. This property offers total privacy, but is just minutes from Park Avenue s shops, restaurants, festivals & parks. Move In and Love Where You Live!"
$3,300,000
1637 CHASE LANDING WAY, Winter Park FL 32789
5
BEDS
6
BATHS
6,272
SQFT
$526
$/SQFT
0.71
ACRES
2002
BUILT
"This exquisite lakefront mansion is nested within the exclusive Windsong Preserve Point community in Winter Park and features an unobstructed view of Lake Berry. The house underwent a no expense spared update. This gorgeous five bedroom, five and a half bathroom home features chef's kitchen with top of line appliances and fixtures, huge wine room, library, movie room, game room, built-in wet bar, and fireplace. This incredible home has A+ rated schools and is only minutes from Winter Park, Park Avenue shopping & dining."
* PRICE LOWERED - $3,400,000 TO $3,300,000 
$3,300,000
455 LAKEWOOD DR, Winter Park FL 32789
4
BEDS
6
BATHS
5,018
SQFT
$658
$/SQFT
0.62
ACRES
1954
BUILT
"Private and sophisticated Winter Park lakefront with stunning views of Lake Osceola. Light and bright with a very open floor plan this residence offers great space for entertainment. The home features two living rooms with a wall of windows, a family room, a bonus room and formal dining room. Tastefully updated with new hardwood floors, new doors and plantation shutters. Updated kitchen with a Thermidor 6 burner gas stove, 2 ovens and an over sized pantry. There is a wet bar in the family room with and icemakeer. The master bedroom on the main floor features a generous sitting area and his and hers master bath that opens to a screened porch with a hot tub - with all new equipment - overlooking the lake. One more bedroom completes this level. The lower level has 2 additional bedrooms and a bath. The outdoors is an entertainer s dream. The upper level with an extensive porch also has a recently added pergola, a re-surfaced pool, and a refinished deck. The lower lower deck features an inviting white sandy beach and a boathouse with plenty of storage for all your water toys. 2 outside extra closets and and an outdoor pool shower complete the outdoors. Great opportunity to live in a beautiful lakefront home on a quiet street close to Park Avenue with all that Winter Park has to offer!"
* PRICE LOWERED - $3,500,000 TO $3,300,000 
$3,175,000
740 PALMER AVE, Winter Park FL 32789
5
BEDS
5
BATHS
4,810
SQFT
$660
$/SQFT
2.79
ACRES
1955
BUILT
"If you re looking for the quintessential Winter Park Lakefront Estate Home this is it! Designed by acclaimed architect Gamble Rogers this magnificent home has double waterfrontage on both Lake Osceola and the Venetian Canal. Located on an oversized 1-acre lot, this home has a formal presence including a grand, circular driveway entrance and a classic front elevation that showcases a 2nd story balcony overlooking majestic palms. As you walk through the front door your eyes are immediately drawn to the unobstructed views of the water; just about every room in the house offers views of the lake. Along the back of the house (lakeside) you ll find the formal living room, sitting room/den, dining room and kitchen; there s also a downstairs guest suite with full bath. Upstairs is the master bedroom, along with three additional bedrooms and two full baths. There is an abundance of storage of throughout the home and the entire estate is impeccable and representative of timeless elegance and class. Surrounded by both historic and brand new multi-million dollar estates this one-of-a-kind property is walking distance to Park Avenue and just minutes to the Interlachen Golf & Country Club, Winter Park Racquet Club, and more."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,250,000 TO $3,175,000 
$3,100,000
1230 N PARK AVE, Winter Park FL 32789
5
BEDS
6
BATHS
5,235
SQFT
$592
$/SQFT
0.97
ACRES
2001
BUILT
"Winter Park- Beautiful estate right off Park Avenue in the private Twelve Oaks peninsula subdivision. The residence sits on a 0.97 acre lot, offering the uncommon luxury of green space, a guest house, 5 car garage, swimming pool, hot tub and fountain all in the heart of Winter Park. The custom built home is California Styled Spanish Colonial with architectural relic 21/2 inch thick front double doors with raised carvings, and 21/4 inch thick Honduran Mahogany doors throughout the main house. The main homes offers 4 bedrooms, 4-1/2 baths, custom mosaic entrance foyer, custom coffered dining room ceilings, covered balcony and covered porch. Family room has 14 ft ceilings with large beams and 3 walls of windows with french doors allowing for views and natural light. The study offers custom built ceiling to floor decorative shelving and mahogany floors. Well appointed chefs kitchen, custom wood cabinetry, walk in pantry all open to include large informal dining space and family room. Guest house with separate entrance, living area, private bath and bedroom, full kitchen and 2 balconies. Additional private gated entry for property access. Schedule your showing today!"
* PRICE LOWERED - $3,400,000 TO $3,100,000 
$3,095,000
409 GENIUS DR, Winter Park FL 32789
5
BEDS
9
BATHS
7,433
SQFT
$416
$/SQFT
0.62
ACRES
2007
BUILT
"This meticulous Mediterranean-style masterpiece looks brand-new and is truly one-of-a-kind, showcasing attention to detail throughout. Encompassing a grand total of 10,072 square feet, the well-appointed open floor plan greets you with a great room boasting 200-year-old massive wood beams and 30-foot stone fireplace. You will also be delighted to find a chef s dream kitchen with two Sub-Zero refrigerators and two dishwashers. The rest of the home includes five bedrooms, nine baths, large media/game room with refrigerator and microwave, outdoor lanai and pool table, maple-paneled elevator, separate bar area and nearby 250-bottle wine cabinet. The master bedroom provides the ultimate in seclusion and offers a see-through stone fireplace and large dual walk-in closets, each with built-in dressers, along with a spa-like master bath. Outside you will discover your private tropical oasis with outdoor kitchen, luxurious heated and saltwater pool area with sun shelf and spa, outdoor shower and fire pit all surrounded on two sides by natural preserve. The exterior boasts reclaimed Chicago brick accents, adding to the intricate detail that makes this exquisite home truly unique. Additional features include natural gas, generator with full-house capacity, and built-in cabinetry and storage in the garages. The owners are leaving the two sets of washers and dryers for the first and second-floor laundry rooms. Perfect for comfortable living and entertaining, this residence will impress the most discerning buyer."
* PRICE LOWERED - $3,250,000 TO $3,095,000 
$2,999,500
1260 ALABAMA DR, Winter Park FL 32789
4
BEDS
5
BATHS
6,302
SQFT
$476
$/SQFT
0.57
ACRES
1991
BUILT
"Beautifully remodeled CANAL FRONT estate on the Winter Park Chain of Lakes. Premier location, a short walk from Park Ave. This oversized lot is lushly landscaped equipped with a new irrigation system and over 215 ft. of canal frontage, with boathouse, on the Venetian canal. BRAND NEW heated salt-water pool & spa with upgraded LED lighting package and automatic retractable pool cover! Home is extremely well built with masonry walls, plus brick and solid stone surround accents. The grand entry welcomes you with a stunning chandelier, updated gathering room with wet bar, extensive trim & moldings, cabinet grade built-ins, 2 fireplaces, new iron railings, gorgeous BRAND NEW rustic oak wirebrush and hand scraped floors throughout the entire house, winding staircase, and updated LUTRON lighting system. Home has a crisp/clean, bright/open design ideal for entertaining and pleasant to the eye in every direction. The kitchen has every convenience of an award winning modern farmhouse style and function including custom cabinetry, fabulous accent lighting, oversized island with ample storage & top grade commercial appliances. Lavish master retreat with dual sided fireplace, sitting/exercise room, picturesque spa like bath & wonderful large island closet. Brand new back staircase to flex space. 3-car garage, extra storage, fully remodeled guest suite, up & downstairs laundry. No detail or expense has been spared in this well executed & designed renovation."
$2,995,000
, Winter Park FL 32789
5
BEDS
7
BATHS
8,910
SQFT
$336
$/SQFT
0.57
ACRES
2013
BUILT
"Masterful design and modern luxury are uniquely embodied in this Spectacular Mid-Century Modern Estate. Stylish simplicity, extensive use of glass, and open design forge a connection with nature. Expansive entertaining spaces flow outside to the Grande Courtyard. Commercial grade Chef s Kitchen with three stately islands and solid granite waterfall counters above the polished porcelain glass tile accentuate natural light. Dimmable lighting allows for opulent control of mood and ambiance. Private bedroom suites, all boast sleek en-suite baths, generous closets with elaborate built-ins, wonderful views and private courtyard access. Every detail was carefully selected and quality crafted for efficient and luxurious living. An automatic shade system gifts seclusion at the touch of a button. The Spacious Master Bedroom is the ultimate retreat with spa-style amenities. A custom designed 19+ car garage, with 20' ceilings, and ample space for lift installation awaits the exotic and classic car collector or RV enthusiast. This secured automotive palace also features temperature control and abundant lighting. Enjoy refined boutique shopping and fine dining as you stroll Park Avenue from home. Convenient access to Orlando s entertainment venues, theme parks, cultural centers and coastline. Ask your CPA about the advantages of transitioning to Florida Homestead & schedule your exclusive private tour of this remarkable residence today."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,199,500 TO $2,995,000 
$2,749,000
2218 VIA TUSCANY, Winter Park FL 32789
5
BEDS
7
BATHS
4,423
SQFT
$622
$/SQFT
0.26
ACRES
2019
BUILT
"Now Completed! Welcome to this very special custom home built by Zoltan Homes. Situated in a prime location in Winter Park. Tremendous open floor plan with over 11ft ceilings on the first floor and 10ft ceilings upstairs. Gorgeous wide plank oak flooring. Truly exceptional & detailed finishes throughout. Spectacular open staircase w/ ceiling height over 30ft tall. Fabulous living area with custom millwork surrounds a gas fireplace. The kitchen is a chef s delight with numerous specialty features including a 11ft island with Cambria top, Sub-Zero/Wolf appliances, including a full size wine tower. Seamless entry to the outdoor living area with an in-wall sliding doors extends to the large lanai with full summer kitchen and remote controlled automated screens. Enjoy the amazing heated salt water spa and pool with 3 fire bowls/fountains and surround by private lush landscaping. Secluded and spacious downstairs master suite overlooks the pool. Expansive walk in closet along with a private laundry room. Luxurious master bath with dual sinks and walk-in shower with digital plumbing controls. There is a downstairs 2nd bedroom/office private suite. Garage with epoxy coating and wall to wall built in functional storage. Fantastic upstairs loft with wet bar which is great for entertaining. As well, there are 3 great en-suites and a secondary full size upstairs laundry room. Interior designed by Steele Street Interiors. Enjoy all of this and just a short stroll to the Racquet Club this is one not to miss!!"
$2,685,000
649 N PARK AVE, Winter Park FL 32789
3
BEDS
5
BATHS
3,180
SQFT
$844
$/SQFT
0.09
ACRES
2018
BUILT
"The luxurious Park Hill townhomes, a legacy residence, have set a new standard of excellence in Winter Park s high end market and are in a class of their own. With only 2 rear units remaining, this is a rare opportunity to own the most well-appointed and exclusive townhomes ever constructed in Winter Park. Built and executed by the vision of Hill Gray Seven Development, Park Hill s classically styled architecture sits atop what is likely the only remaining new construction along the prominent stretch of Park Avenue. Created to stand the test of time, the flawless construction includes the highest quality materials: tumbled handmade Old Carolina brick, 3 story block construction, soundproof hollow core floors, precast exterior trim, copper flashing, and a slate mansard roof. Interior features are lavish, with high ceilings on every floor, walls of windows, French doors, custom built-ins, intricate trim & crown molding, custom closets, and smart home technology throughout. Spanning 3 floors, there are 3 bedrooms plus bonus room, gourmet kitchen with Wolf Sub Z appliances, and great entertaining space inside and out. Other amenities are private elevator, outdoor summer kitchen, rooftop terrace, 2 car garage. Fee simple ownership, exterior maintenance handled by the association. Perfect location, easy to lock & leave...become part of Winter Park s legacy of excellence."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,790,000 TO $2,685,000 
$2,595,000
581 SYLVAN DR, Winter Park FL 32789
3
BEDS
4
BATHS
4,503
SQFT
$576
$/SQFT
0.73
ACRES
1946
BUILT
"This premier Winter Park lakefront property on Lake Osceola provides an opportunity to build anew, renovate or use existing home on an absolutely beautiful elevated lot of approximately 0.75 acres. It overlooks arguably the most beautiful serene cove on the Chain of Lakes. Enjoy magnificent, long, picturesque sunset views while also being on an extremely private lot. The property is set up well to gate off the entrance with over 300 feet of depth, so the new home would be set back noticeably from the street. There are approximately 90-100 feet on the lake and majestic oaks and cypress trees on the property. The buyer can build about 10,000 square feet or more on this property. Boat to the downtown Winter Park area on one of only two lakes on the Chain of Lakes in City of Winter Park with no boat ramp. This is one of the quietest lakes in terms of boating activity as boaters must go through canals to get to this lake."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,795,000 TO $2,595,000 
$2,575,000
900 N PARK AVE, Winter Park FL 32789
5
BEDS
7
BATHS
5,035
SQFT
$511
$/SQFT
0.41
ACRES
2005
BUILT
"LOCATION! LOCATION! LOCATION! Luxury and elegance abound in this timeless Park Avenue estate, in one of the most sought after Central Florida locations, steps from the best of downtown Winter Park s vibrant dining, shopping, arts & culture, MOVE-IN READY! Custom built by Carlos Posada, this 5,035sf estate home has 4 spacious bedrooms, 1 bedroom/1 bath guest house, bonus room, office, formal living and dining rooms, abundant indoor & outdoor entertaining spaces, and sits on almost half an acre of prime real estate. Soaring ceilings and expansive windows infuse sunshine and light throughout. The custom windowed eat-in kitchen includes a center island, Thermador appliances with 6-burner gas range, granite counters, Travertine marble floors, tons of storage, and adjacent butler's pantry with wine bar. Downstairs master suite is the epitome of indulgence with grand bathroom and a large walk-in closet. Emulating a 5 star resort, the view from master bedroom overlooks the lush backyard, bountiful bougainvillea, pool with waterfall, and courtyard. Designer finishes include arched French doors, new hardwood floors, custom iron-work, beamed ceilings, extensive millwork, and authentic barrel tile roof. Other extras include new interior paint, 3 fireplaces, surround sound, a double and single garage with new floors & AC, wrought iron automatic security gate, beautiful landscaping, and a heated splash pool. Main house is 4703sf and guest apartment is 332sf for a total of 5035sf."
* PRICE LOWERED - $2,645,000 TO $2,575,000 
$2,335,000
125 S INTERLACHEN AVE #5, Winter Park FL 32789
2
BEDS
5
BATHS
3,244
SQFT
$720
$/SQFT
0.35
ACRES
2016
BUILT
"Under Construction. Completion by July! Only two residences remain. Your opportunity to own unprecedented luxury in the most exclusive area of Winter Park has arrived. South Interlachen Place is around the corner from world famous Park Avenue, across the street from the Alfond Inn and just a stone s throw from the Winter Park Chain of Lakes. Comprised of six exquisitely appointed townhouses, South Interlachen Place is being built with premium level specifications; a standard of luxury usually only found in world-class destinations. The project was designed by award-winning architect Randall Slocum of Slocum Platts. Privacy is the top priority: every fee-simple residence includes a private two-car garage, private elevator to all levels and lush, mature landscaping defining the entrances. A truly unique aspect of the design is the extraordinarily large and private rooftop terrace for each individual residence, providing both covered and open areas for outdoor dining and entertaining. Each private rooftop terrace comes with a fireplace and a powder bath. The residences are designed with age in place features throughout, allowing for the adaptation of changing lifestyles. Each townhouse embraces smart technology for entertainment, lighting, energy management and security. Live in one of the most extraordinary residences in a truly exceptional Winter Park location at South Interlachen Place."
* LISTED OVER 120 DAYS  * PRICE INCREASED - $2,244,000 TO $2,335,000 
$2,275,000
121 W KINGS WAY, Winter Park FL 32789
5
BEDS
7
BATHS
5,233
SQFT
$435
$/SQFT
0.40
ACRES
2019
BUILT
"This Stunning and Elegant new Transitional Style home welcomes you to old Winter Park. With an open floor plan, soaring ceilings, great natural light, this 5 bedroom 5 bath+ pool home affords both luxurious living and a fabulous space for entertaining. Downstairs includes an amazing master suite with adjacent study, additional guest bedroom and full pool bath, glamorous great room with fireplace of ledger stone, strikingly beautiful kitchen and bar area with large island, quartzite countertops, marble back splash, Thermador appliances, walk-in pantry, huge laundry room and three car garage. Upstairs offers a central open loft area, three additional bedrooms, baths and second laundry area. Stately from the outside with large front parking area and lovely landscaping, the home has great curb appeal. For fun and entertaining, the back yard offers a large pool with limestone deck, covered lanai and professional style summer kitchen. Located in a sought after, well-established neighborhood just one mile from Downtown Park Avenue and Rollins, it is wonderful for walking or biking with its many tree canopies and brick streets. Zoned for the popular new Audubon Park School (K-8) with convenient access to FL Hospital and Downtown Orlando. Built with quality and high end finishes, this new construction home has all the WOW factors a discriminating buyer hopes to find in an amazing Winter Park location."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,325,000 TO $2,275,000 
$2,275,000
1000 ANCHORAGE CT, Winter Park FL 32789
6
BEDS
7
BATHS
6,177
SQFT
$368
$/SQFT
0.59
ACRES
1982
BUILT
"This luxurious estate is a European masterpiece located in the golden triangle of Winter Park. A mature, well manicured podocarpus hedge surrounds this .59 acre property and affords the ultimate in privacy. Enter through the grand portico featuring custom marble floors with onyx inlay and an elegant sweeping staircase with hand painted gold leaf details.The downstairs floor plan is a perfect example of the sophisticated salons that epitomize gracious European living. Downstairs includes a formal dining room with custom pocket doors, living room with gas fireplace, a den, an office and a wonderful, large family room also with a gas fireplace. The current kitchen was added during the home s renovation and includes granite countertops, a copper farm sink with Bosch dishwashers on each side, a spacious island, Thermador appliances, a butler s pantry, French country built-ins, and a mud room. The incredible view from the kitchen of the enormous pool and backyard makes the kitchen a favorite gathering place! Upstairs is equally as lovely with an exercise room plus 4 bedrooms, including a spacious master suite featuring 3 balconies, gas fireplace, a sitting area and concealed mini-bar. A walk-in dressing room master closet is one of the most prized elements of this magnificent space. This home even has a complete two bedroom, one bath apartment above the garage ideal for a game room or living space for a nanny, guest or in-laws. Nestled in a private cul-de-sac, don t miss this exceptional home!"
* LISTED OVER 120 DAYS 
 
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