Winter Park Real Estate, Homes and Condos for sale

All Winter Park homes currently listed for sale in Winter Park as of 01/20/2019 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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$7,895,000
866 VIA LUGANO, Winter Park FL 32789
6
BEDS
10
BATHS
10,613
SQFT
$744
$/SQFT
3.36
ACRES
2015
BUILT
"Located in the desirable Winter Park Via's on Lake Maitland, this breathtaking six-bedroom, ten-bath Mediterranean estate has been crafted with the finest finishes. Built in 2015, a top-of-the-line kitchen with island offers a double oven and butler s pantry. After a long day, retreat to a spacious master suite with spa-like bath and two spacious walk-in closets. There are also dual offices, a private home theater and a convenient home gym. Boasting multiple fireplaces and gorgeous elevated expansive views of the largest lake on the six-lake Winter Park Chain of Lakes, this is truly an entertainer s dream. A summer kitchen with multiple lanais is perfect for enjoying the Central Florida lakefront lifestyle. Relax on your own private sand beach with a fire pit and a spectacular infinity-edge pool and spa. Note: Home was designed and built by an award-winning builder, architect and designer. Priced including furnishings inside/out by Marc-Michaels Interior Design firm."
$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."
$4,995,000
1821 PINETREE RD, Winter Park FL 32789
5
BEDS
7
BATHS
5,006
SQFT
$998
$/SQFT
0.64
ACRES
2018
BUILT
"Modern Luxury - Tucked away in the Vias of Winter Park sits this Stylish, Contemporary Smart Home on Lake Maitland. The Brand New Lakefront Residence combines innovative design with brilliant architectural artistry, in a prime location that is both exclusive yet convenient. Just completed in 2018, this exquisite home features state-of-the-art technology throughout, accented by classic, elegant finishes such as Walnut Staircase, Landing and Interior Doors. Smart Home elements are iPad & Touch Panel integrated, and include Surround Audio, Lighting Control, Video Doorbell with off-site answering, Garage Door Control, Voice Control, Retractable Phantom Screens off Lanai, Interior/Exterior Wi-Fi Access Points, and Patio Screen Control. Other interior features include a gas fireplace, glass enclosed office space, formal dining room, and 2nd floor den. Chef's Kitchen features Luxury Dacor Appliance Package, and Dual Dishwashers, Double Ovens, Warming Drawers, Walk-in Pantry, and Wet Bar with Wine Cooler. Lakeside, enjoy your outdoor kitchen, gas fire pit, sparkling pool, and rinse off using the outdoor shower heads. Enjoy access to Lake Maitland, Winter Park s largest lake in the Chain of Lakes, from your backyard, and take in the views while you lounge poolside."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $4,999,000 TO $4,995,000 
$4,750,000
115 PALMER AVE, Winter Park FL 32789
4
BEDS
5
BATHS
9,838
SQFT
$483
$/SQFT
1.30
ACRES
1989
BUILT
"Location Location Location! This is your opportunity to own this stunning Winter Park Estate just a short and beautiful walk to Park Avenue and everything it has to offer. The majestic residence sits on 1.5 acres and has over 280'on the enchanting Winter Park chain of lakes (Lake Maitland) The home boasts gorgeous lake views from most rooms, a lovely sprawling private master suite, formal living with a wood burning fireplace, elegant entrance, great kitchen for entertaining guest who want to see the lake views from the newly enclosed sun room. Over sized backyard with pool, open porch area, outdoor shower, impeccable landscaping throughout the yard & recently updated boat house."
* LISTED OVER 120 DAYS 
$3,995,000
1400 GREEN COVE RD, Winter Park FL 32789
5
BEDS
7
BATHS
6,384
SQFT
$626
$/SQFT
0.85
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 renovated 3 years ago 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."
$3,695,000
472 HENKEL CIR, Winter Park FL 32789
4
BEDS
7
BATHS
4,686
SQFT
$789
$/SQFT
0.39
ACRES
2017
BUILT
"Winter Park Chain of Lakes modern masterpiece home custom built by Fred Schaub Homes. Close to 5,000 square feet of luxurious finishes, pristine lakefront views and modern features featuring 10' Casablanca stained folding La Cantina doors that open to a Sub Zero/Viking summer kitchen, oversized Infinity edge pool with glass tiles, heated spa and aeration fountains and gas fit feature all overlooking Lake Mizell. Master Bedroom features lakefront views, high ceilings, custom built closets and marble bathroom featuring separate glass shower and freestanding tubs. Additional closets offer additional storage space. All bedrooms feature En Suite bathrooms and customized walk in closets. Living room with gas fireplace opens up to gourmet kitchen, additional wet bar with wine refrigerator and space for dining table to seat 12 guests. State-of-the-Art home technology includes security cameras, surround sound, media, AC systems used with Ipad docking stations and Iphone enabled controls. Wrap around terrace illuminated by gas torches light up the night all the way down to the lakefront boathouse complete with secured storage and covered boat lift. Custom herringbone pavers line the driveway to oversized 3 car garage with custom epoxy garage floor. Don't miss the opportunity to own this modern luxury lakefront home in the heart of Winter Park."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,799,000 TO $3,695,000 
$3,500,000
2170 W FAWSETT RD, Winter Park FL 32789
5
BEDS
7
BATHS
6,589
SQFT
$531
$/SQFT
1.22
ACRES
1925
BUILT
"A rare opportunity to own one of Winter Park s most distinguished homes. This beautiful Lakefront, Tudor style, home with guest house sits on over 1.2 acres on Lake Sue. This impeccably well-maintained home is extremely private and wonderful for entertaining. It features a downstairs master suite with separate sitting room, large bath and walk-in closet. Upstairs are three additional bedrooms and baths plus a bonus room. The kitchen/family room leads to a sun-filled dining room and formal living room with views of Lake Sue. Crafted with meticulous attention to detail, there are hand-hewn antique wood beams in the master and pecky cypress ceiling in the basement, wine room, front and back porch. This home has hardwood floors throughout, except the basement which is travertine, as well as 5-inch copper gutters and a gorgeous slate roof. French doors lead out to spacious courtyard, pool and barbecue. This home is surrounded by gorgeously landscaped grounds, and a large guest house with a full kitchen and bath and a two car garage. Enjoy the evening sunsets from your private boat dock and only blocks from Park Avenue, shopping and incredible restaurants."
* LISTED OVER 120 DAYS 
$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 is scheduled for spring 2019. 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 
$3,390,000
637 N PARK AVE, Winter Park FL 32789
3
BEDS
5
BATHS
4,237
SQFT
$800
$/SQFT
0.07
ACRES
2018
BUILT
"Under Construction - 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 5 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 
$3,250,000
740 PALMER AVE, Winter Park FL 32789
5
BEDS
5
BATHS
4,810
SQFT
$676
$/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 - $3,450,000 TO $3,250,000 
$3,200,000
, Winter Park FL 32789
5
BEDS
7
BATHS
8,910
SQFT
$359
$/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."
* NEW LISTING 
$3,100,000
275 E WEBSTER AVE, Winter Park FL 32789
8
BEDS
8
BATHS
6,730
SQFT
$461
$/SQFT
0.57
ACRES
1978
BUILT
"One of downtown Winter Park s most beloved homes is for sale! Situated on half an acre, 2 blocks from Park Ave. on the Winter Park Golf Course, its welcoming wrap-around front porch is the perfect place to relax and take in the beauty. Inside, the spacious study and dining room both offer sweeping views of the sprawling front yard and golf course. Step into the kitchen and you ll find the heart of the home. Equipped with granite and teak counter tops, custom framed double-sized Sub Zero refrigerator, custom blue 6-burner + grill Professional Viking range, 8 x 5 island, walk-in pantry/mudroom and much more. The kitchen opens to the inviting family room and large gathering room with fireplace. Also found on the first floor is the spacious master suite with vaulted beamed ceilings, fireplace and French doors that open to the pool. Upstairs are 5 bedrooms, 4 of which have en suite bathrooms and one bedroom that is currently the game room with its vaulted ceilings and plenty of space to play. Included upstairs is the full-size laundry room with large, walk-in storage area. (There is also a washer/dryer hook-up in the master bathroom). The backyard hosts a 20 x 40 pool, pool bath, laundry room, generator that runs the entire home and covered porch that is the length of the home. The breezeway attaches to the over-sized 3-car garage and has an 800 square foot 2/1 apartment with private entrance. This one-of-a-kind home is perfect for large entertaining or cozy family gatherings."
$2,995,000
2049 VENETIAN WAY, Winter Park FL 32789
5
BEDS
9
BATHS
7,631
SQFT
$392
$/SQFT
0.96
ACRES
2009
BUILT
"JUST REDUCED by $455,000! Priced to sell it s the lowest $/SF on the Winter Park Chain of Lakes!!! Come see this unbelievably gorgeous lakefront estate home in Winter Park. Located on the quiet side of Lake Maitland, this 5 bedroom, 7,600 SF home features formal living areas, a home office, downstairs master and guest suite, upstairs bonus room, a game room with a temperature controlled wine chateau, heated pool, a private boathouse, and 4-car garage. Beautiful travertine and wood floors flow throughout the home, complimented by extensive mill work and crown moldings, 4 gas fireplaces, high ceilings, and French doors that seamless blend indoor and outdoor living together. The gourmet kitchen offers high-end appliances, including gas range, double ovens, built-in espresso machine, and a large walk-in pantry. The luxurious master retreat has a spa bath fit for a king, an attached sitting room, and access to the resort-style pool and spa. Each of the 4 guest suites are oversized and have a full, private bath, as well as spacious walk-in closets. Upstairs, in addition to the game room is an expansive bonus room, 2nd laundry room, and covered balcony with panoramic views. Completely fenced, the backyard has a large green space ideal for entertainment and the 4-car garage and motor court are located behind an electronic gate. Just minutes from the Racquet Club, Interlachen Golf & Country Club, and Park Avenue this home is sure to impress with all its amenities."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,450,000 TO $2,995,000 
$2,890,000
647 N PARK AVE #8, Winter Park FL 32789
3
BEDS
4
BATHS
3,253
SQFT
$888
$/SQFT
0.12
ACRES
2018
BUILT
"Under Construction - 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 5 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 
$2,790,000
649 N PARK AVE, Winter Park FL 32789
3
BEDS
4
BATHS
3,180
SQFT
$877
$/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 5 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."
$2,749,000
2218 VIA TUSCANY, Winter Park FL 32789
5
BEDS
7
BATHS
4,423
SQFT
$622
$/SQFT
0.26
ACRES
2019
BUILT
"Under Construction! 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 walnut 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!!"
$2,700,000
1020 N PARK AVE, Winter Park FL 32789
5
BEDS
8
BATHS
7,101
SQFT
$380
$/SQFT
0.36
ACRES
2004
BUILT
"Price improvement! In the beautifully lit and airy, temperature-controlled lanai, you will find an additional fireplace, summer kitchen, and electronic hurricane shutters. The fantastic outdoor setting includes a heated pool, spa, and outdoor fireplace a perfect place for entertaining. The property benefits from a fully operational elevator which you can take to the base level of the home. This floor includes a fully equipped gym, climate-controlled wine cellar, full wet bar, game room, movie theater, and two full bedroom suites. The upstairs floor also offers two beautifully appointed bedroom suites. This exquisite, custom Mediterranean home presents a fantastic opportunity to live on Central Florida s most renowned street. Elegance, luxury, and entertainment can be found here in the heart of Winter Park, just a short walk from all fine restaurants and shopping on Park Avenue. As soon as you enter this home, your eyes will instantly be drawn to the attention to detail given by the award-winning builders Maroon Fine Homes & Marquis Fine Homes. The home is expertly laid out over 3 floors, featuring a formal living room with a fireplace, as well as a family room, dining room, study, master bedroom, and gourmet kitchen with professional appliances."
* PRICE LOWERED - $2,800,990 TO $2,700,000 
$2,695,000
1760 W FAWSETT RD, Winter Park FL 32789
6
BEDS
7
BATHS
4,637
SQFT
$581
$/SQFT
0.30
ACRES
2017
BUILT
"Stunning, newly built, and redesigned home in the Heart of Winter Park! Built in 2017, this gorgeous 6 bedroom, 6.5 bath pool home offers a modern, sophisticated interior with high end finishes, and an open concept layout that includes formal living and dining, a great room, chef inspired kitchen, downstairs master bedroom, a guest suite, and amazing outdoor living possibilities. Throughout the first floor you ll find beautiful wide plank hardwood floors, complimented by high ceilings, gas fireplace(s), and glass sliders that bring in great natural light, as well as provide a seamless transition between indoor and outdoor living. The master bedroom is located within its own wing of the home and features an oversized dressing room/closet and luxurious master bath with freestanding tub, his and her vanities, and a walk-in shower. Upstairs you ll find 3 spacious en suite bedrooms and 2 bonus room. Atop a second flight of stairs, you ll find a separate bonus/6th bedroom with full bath. The covered lanai with phantom screens offers an outdoor kitchen and views of the saltwater pool. Other amenities include a 3-car garage, metal roof, insta-hot water heaters, and more. Located just minutes from Park Avenue this home is zoned for the brand new Audubon K-8 school and is just a short drive to nearby Lake Highland Prep."
$2,695,000
1260 N PARK AVE, Winter Park FL 32789
6
BEDS
8
BATHS
6,576
SQFT
$410
$/SQFT
0.45
ACRES
2008
BUILT
"This is a breathtaking gated modern Mediterranean masterpiece on a premier street right through downtown Winter Park. A short stroll along famed Park Avenue to all of the shops and dining, this exquisite home boasts only the finest finishes coupled with modern technology and a wonderful open floor plan. Brazilian walnut, exotic granites and marble, cherry and mahogany cabinets, built-ins, soaring ceilings and grand entry are just the starting points to the list of details. The master retreat has dual separate closets and baths. A breakfast bar and elegant library, along with a gracious formal dining room overlook Park Avenue, with temperature-controlled wine cellar and butler pantry leading to a very spacious chef's island kitchen. Access the second-floor media room and four en-suite bedrooms with elevator as well as a private rooftop terrace with fireplace. The Lutron lighting systems allow one touch lighting control for the home and smart entertainment system is perfect for music control. Over the three-car garage is a full private guest apartment with its own entrance, open living area, kitchen and bedroom with a catwalk that also attaches it to the main house second floor. An outdoor living space with summer kitchen and fireplace leads to a luxurious pool and spa with ample beach area surrounded by private yard all walled in for complete privacy and security."
$2,499,000
2550 VENETIAN WAY, Winter Park FL 32789
4
BEDS
5
BATHS
4,875
SQFT
$513
$/SQFT
0.27
ACRES
2008
BUILT
"DON'T MISS THIS SPECTACULAR CUSTOM WATER-FRONT HOME OF YOUR DREAMS! Jump on your boat and cruise out to Lake Maitland and the entire Winter Park Chain of Lakes! Located in the VIAs of Winter Park. Easy access to everything you love about Winter Park, Maitland and Orlando. Downstairs: Chef's Kitchen with walk-in pantry, Double Oven Gas Stainless Thermador Range, Integrated Refrigerator, Island with prep. sink, Wine Refrigerator, Breakfast Bar - All Open to the Spacious Family Room! Water Views Everywhere! Downstairs Master Suite with huge walk-in closets, separate shower and soaking tub, Private Water Closet w/ bidet. Half Bath with both interior and exterior access. Another Half Bath next to the Over-Sized Laundry Room. Over-Sized Garage: 2 cars Plus! The Boathouse may be calling you but the outdoor living spaces will beckon you to stay! Upstairs: Three more bedrooms, Two Bathrooms, Media Room, Gym/Bonus Room and a Versatile, Open Loft Space for use as a game room and Upstairs Family Room. Enjoy Breezes and Water View from the Upstairs Balcony. Schools: The Trifecta of: Dommerich Elementary, Maitland Middle and Winter Park High! Be sure to check out the Virtual Tour and Photos to fully appreciate this home. It's even better in person!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,650,000 TO $2,499,000 
$2,499,000
699 OSCEOLA AVE, Winter Park FL 32789
5
BEDS
4
BATHS
5,409
SQFT
$462
$/SQFT
0.90
ACRES
1930
BUILT
"DECEMBER P R I C E R E D U C T I O N. This is an authentic SANTA BARBARA LIKE 5 Bedroom Spanish Mediterranean Lakefront Estate. Available in downtown Winter Park, Florida. Woven into the history of Winter Park, the home is comfortably updated to today s standards, yet express s the character, warmth, and architecture of the 1930 s. The unique setting offers privacy, quiet seclusion, and clear expansive views throughout the entire home of Lake Osceola. Exceptional attention was focused on interior & exterior details, finishes & unique fixtures. The outdoor covered living space, was updated by Phil Kean design. It provides breathtaking views of the lake, sandy beach, pool, and landscape. The home features one of if not the oldest and largest oak trees in Winter Park. The home is featured in the Winter Park boat tour for it's beauty and history. This Estate also highlights a large sunny family room with original cypress beams & tiled wood burning fireplace, large master suite (on main floor), gourmet kitchen. Upstairs showcases 4 spacious bedrooms, all presenting Lake Osceola, pool, and garden views. Enjoy the close and easy walk to Park Avenue, Rollins College, known for its favorite eats, classes, culture, and events. This Winter Park Estate is a true masterpiece. A true one of a kind estate home with an incredible history."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,675,000 TO $2,499,000 
$2,495,000
266 CHASE AVE, Winter Park FL 32789
5
BEDS
6
BATHS
4,088
SQFT
$610
$/SQFT
0.31
ACRES
1930
BUILT
"Live in Downtown Winter Park with Park Avenue in your line of sight! Walk to local shops and restaurants as well as Rollins College, The Alfond Inn, and the Winter Park Public Library. Newly renovated and expanded with meticulous attention to every detail, this is the type of unique and historic property you ll want to keep in your family forever. The home has even caught the eye of a home renovation television show and is set to be featured in an upcoming episode! The addition includes a spacious Master retreat with an elegant master closet, marble spa bathroom with Imperial Danby countertops, and custom wood cabinetry. After re-configuring the first floor of the home to create an open-concept kitchen and living space, new white oak flooring was added throughout the home. The stunning kitchen features Busby cabinetry, upgraded stainless steel appliances, Greek marble back-splash, and a host of other custom features! The renovation includes new moldings, roof, HVAC, plumbing, electrical, fencing, and landscaping. The Guest Home also underwent its own makeover with a brand-new kitchen and bathroom! Don t miss out on this unique opportunity to own a piece of Winter Park History. Make your appointment today for a private showing."
$2,469,000
750 PINETREE RD, Winter Park FL 32789
5
BEDS
7
BATHS
4,780
SQFT
$517
$/SQFT
0.39
ACRES
2014
BUILT
"Stunning dream home located in the highly desirable WP Vias! Situated on a rare, oversized lot, this home was custom built by Parkland Homes and is across the street from Lake Maitland and a short stroll to the WP Racquet Club. Elegantly appointed with the finest finishes, this transitional open floor plan is an entertainer's delight. A formal parlor and adjacent dining room greet you as you enter into the grand living space. The chef s kitchen has an awe-inspiring oversized granite island, huge walk-in pantry, wine cellar, professional grade appliances, and Busby cabinetry. The kitchen opens to the expansive family room with fireplace that overlooks the swimming pool and backyard. The gorgeous first-floor master suite features a spa-like bath with jetted tub, separate walk-in shower with an outdoor shower feature. An additional downstairs en-suite bedroom is perfect for guests. The second-floor loft opens to a covered balcony that provides perfect views of Lake Maitland and three en-suite bedrooms, a gym/media room with half bath, and second laundry. The expansive backyard with covered lanai, pool, and spa are an excellent way to enjoy the Florida lifestyle. Two of the three garages offer ample space for cars, while the 3rd has been professionally converted to an A/C studio/office that is included into the square footage. Welcome to Paradise!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,500,000 TO $2,469,000 
$2,450,000
531 VIRGINIA DR, Winter Park FL 32789
4
BEDS
4
BATHS
4,955
SQFT
$494
$/SQFT
1.91
ACRES
1951
BUILT
"Exquisite lakefront family home on over 1.91 acres on the Winter Park Chain of Lakes with over 100 feet of lake frontage. Dramatic entrance way to home immediately directs your attention to the stunning lake views seen from the large windows covering entire rear of home. The open space design features 4 large bedrooms, 3 1/2 baths, over-sized swimming pool and lanai with summer kitchen. Large master bedroom has dual french doors looking out onto lake and spectacular views of Rollins College Knowles Chapel. M/bath has walk-in shower with dual shower heads and jacuzzi tub. Beautiful hardwood floors throughout home. Three car garage. Wired alarm and stereo throughout home. Gourmet kitchen with gas range, dual ovens, Miele dishwasher. Living area is large and spacious with vaulted ceilings and and large fireplace. This home is at the end of a dead-end street and enjoys little to no traffic presence, helping to make it a wonderful place for you family to create its own lake home memories. Located in the highly sought after neighborhood of Timberlane Shores. Minutes from Park Avenue and walking/biking distance to A rated schools. You and your family will feel like you are lucky enough to live in your vacation home everyday!"
 
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