Winter Park Real Estate, Homes and Condos for sale

All Winter Park homes currently listed for sale in Winter Park as of 03/24/2019 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."
$4,795,000
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."
$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 
$4,300,000
935 GREENTREE DR, Winter Park FL 32789
3
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."
$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."
$3,675,000
1400 GREEN COVE RD, Winter Park FL 32789
5
BEDS
7
BATHS
6,384
SQFT
$576
$/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."
* PRICE LOWERED - $3,995,000 TO $3,675,000 
$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, Tudor style, Lakefront 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 
$3,445,000
1400 N NEW YORK AVE, Winter Park FL 32789
5
BEDS
6
BATHS
5,684
SQFT
$606
$/SQFT
3.11
ACRES
1977
BUILT
"One of Winter Park's premier Golden Coast Lakefront Estates. Walk to downtown Park Ave from this hidden, prime location situated on over three acres with 160 feet on Lake Maitland. This unique property on a quiet cul-de-sac features the main house with spectacular waterfront views and detached guest residence above 3 car garage with separate entrance from the porte cochere. Guest quarters offers full kitchen, additional bedroom, bathroom, living room, dining, inside utility and storage room. This Modern floor plan has been beautifully updated with custom chef's kitchen, designer solid-wood cabinetry, granite, true walk-in pantry plus 15x10 inside utility with additional refrigerator, pantry and storage conveniently located on the main floor. Floor to ceiling views greet you as you enter this lakefront private retreat with warm and inviting family room off kitchen, professionally appointed with craftsman wood detail and crown molding. Downstairs guest bedroom with private bath and large media room with additional full bathroom and storage closet. Spacious second floor master bedroom features a large picture window overlooking the lake. His and Her bathrooms plus den/office, workout area overlooking Lake Maitland with stunning outdoor entertaining area leading to your own private boat dock. Enjoy morning sunrises and glorious sunsets from this one of a kind Winter Park Estate. Also excellent opportunity to expand structure per FAR (Floor Area Ratio) allowable guidelines up to 15,000 square feet!"
* PRICE LOWERED - $3,495,000 TO $3,445,000 
$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 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
639 N PARK AVE #4, Winter Park FL 32789
3
BEDS
5
BATHS
4,244
SQFT
$799
$/SQFT
0.07
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."
$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 
$3,199,500
, 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."
* PRICE LOWERED - $3,200,000 TO $3,199,500 
$2,975,000
2010 W FAWSETT RD, Winter Park FL 32789
5
BEDS
6
BATHS
6,786
SQFT
$438
$/SQFT
0.43
ACRES
2006
BUILT
"Welcome to Casa Bella Vista. Magnificent one-owner Mediterranean lakefront featuring quality and character throughout capturing lake views from almost every room with an elevated vantage point of Lake Sue. Features include gathering lakefront room with gas fireplace, formal dining room with butler's pantry & wine refrigerator, and wonderful island kitchen with Sub-Zero refrigerator, granite counters, prep sink, 6 burner Wolf cooktop, double ovens, bar seating, plus separate breakfast room overlooking pool. The main level master suite has stunning lake views & French doors to patio, custom walk-in closet, large luxurious bath with spa tub and separate shower, plus adjacent richly appointed office with built-ins. The upstairs has three bedroom suites, homework station, and its own laundry for this level. Finally, there is a lower lake level for all your entertaining that includes an enormous home theater/game room, full bar and 2nd kitchen area, media/theatre room, laundry/craft room, plus fifth private bedroom/guest suite. Additional amenities include travertine and hardwood floors, extensive moldings, built-ins, specialized electronics, security cameras, automated lighting, great storage, multiple patios/terraces, gas pool heater and home generator. Outdoor living includes manicured grounds with private backyard fenced with keyed access for security and tropical pool with beach area and, full summer kitchen. Lakefront living includes a complete boat house with AC to enjoy amazing sunsets over Lake Sue."
* PRICE LOWERED - $3,050,000 TO $2,975,000 
$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 
$2,795,000
581 SYLVAN DR, Winter Park FL 32789
3
BEDS
4
BATHS
4,503
SQFT
$621
$/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."
$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 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!!"
$2,499,000
699 OSCEOLA AVE, Winter Park FL 32789
5
BEDS
4
BATHS
5,062
SQFT
$494
$/SQFT
0.90
ACRES
1930
BUILT
"BEAUTIFUL 1930s 5 Bedroom Lakefront Estate. Located in downtown Winter Park, the estate has been professionally updated, yet has the character, warmth, and architecture of the 1930s. The setting offers privacy, and clear Lake views throughout each room in the home. Exceptional attention was focused on interior & exterior details, finishes & unique fixtures. The outdoor covered living space was updated by well known designer Phil Kean. The home provides breathtaking views of the lake, sandy beach, pool, and stunning landscape. This home also features one of if not the oldest and largest oak trees in Winter Park. Listen as the boat tour goes by as the home as it is featured in the boat tour This Estate also highlights a large living room with original pecky cypress beams & wood burning fireplace, large master suite (main floor), gourmet kitchen.(lake view) The second floor showcases 4 spacious bedrooms with lovely lake and garden views. Enjoy the close easy stroll to Park Avenue & Rollins College. Park Avenue is known for Restaurants, Unique Shops & the popular Saturday Farmers Market. Rollins College Campus offers year round cultural events. This Winter Park Estate is a gorgeous peaceful home awaiting to welcome its new family. Please call to schedule your private showing."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,675,000 TO $2,499,000 
$2,495,000
1760 W FAWSETT RD, Winter Park FL 32789
6
BEDS
7
BATHS
4,637
SQFT
$538
$/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."
* PRICE LOWERED - $2,645,000 TO $2,495,000 
$2,495,000
1600 HIGHLAND RD, Winter Park FL 32789
5
BEDS
7
BATHS
6,345
SQFT
$393
$/SQFT
0.46
ACRES
2008
BUILT
"This modern Tuscan Parade of Homes winner was custom-built with fabulous design and versatility. With Spanish Mediterranean influence, the home creates spaces that are excellent for indoor/outdoor entertaining and casual resort-style living, as well as a sleek courtyard design for the ultimate in entertaining and privacy. A solid oversized Mahogany pre-entry door leads to an outdoor private oasis complete with pool and alfresco dining prior to approaching the main residence entry foyer. Retractable screens create a seamless indoor-outdoor living. Other features include two amazing chef's kitchens (both a primary and entertaining/catering kitchen) with natural gas commercial appliances including a grill, steam oven, three convection ovens and a Wolf pizza oven surrounded by custom cabinetry and a barrel brick ceiling. The downstairs master retreat has a sitting area, two-sided fireplace and access to outdoor lanai through motorized sliding doors, as well as a master bath with dual water closets, steam shower, and massage room with adjoining cedar-lined dry sauna. Downstairs also includes another bedroom suite, spacious open gathering room, multiple dining areas, private theater, dual office and separate guest casita, which allows for truly a one-level living experience. The second floor enjoys two more bedroom suites, a workout area and flex living space. Other features include Crestron home automation system, thermal pane windows, refrigerated wine room, 15 security cameras and five-car capacity garages."
* PRICE LOWERED - $2,598,000 TO $2,495,000 
$2,375,000
750 PINETREE RD, Winter Park FL 32789
5
BEDS
7
BATHS
4,780
SQFT
$497
$/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 - $2,469,000 TO $2,375,000 
$2,350,000
141 N VIRGINIA AVE, Winter Park FL 32789
5
BEDS
6
BATHS
4,018
SQFT
$585
$/SQFT
0.06
ACRES
2018
BUILT
"A fantastic opportunity for a discerning buyer to own Oak Tree House, the Jewel in the Crown of the Phil Kean designed Brownstones located in downtown Winter Park. Just a short stroll to Park Ave's fine dining and shopping, the Farmer's Market, Hannibal Square, the WP Village area and more. Oak Tree House is a 5 bed, 5.5 bath, 3-story residence with a private elevator to all floors, high-end cabinetry and flooring, designer lighting & plumbing fixtures & a stellar kitchen including top of the line Miele appliances . The main living area (kitchen, dining, living rooms & downstairs bathroom) is on the 1st floor with the 2nd floor offering a multitude of options with room for four separate guest suites (all with ensuite bathrooms) any of which could be used for other purposes, office, games room etc. The beautiful staircase or the elevator lead to the 3rd floor which houses the full floor Master Suite including a 22 x 21 roof-top terrace with a top of the line jacuzzi hot tub. Other enhancements include a heated floor in the master bath, a coldstore pantry, internal vacuum system and Pelican water filtration system for all the water in the house. Enjoy green space at the front & side yards. Perfect for the urbanistas who love to walk to everything, the global travelers who need to lock & leave & the commuters who need access to Downtown Orlando & I-4."
 
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