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Winter Park FL Real Estate & Homes For Sale

305 Properties Found

The median home value in Winter Park, FL is $265,200. This is lower than the county median home value of $297,100. The national median home value is $170,100. The average price of homes sold in Winter Park, FL is $265,200. Approximately 55.8% of Winter Park homes are owned, compared to 31.31% rented, while 12.89% are vacant. Winter Park real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Winter Park real estate agent to arrange a tour today!
Learn more about Winter Park Real Estate.


11 - 20 of 305 Properties Displayed
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$3,399,000

110 Osceola Court Winter Park, FL 32789

Beds:
5
Baths:
6.00
Sq.Ft.:
6,713
Status:
Active
MLS#:
O4853377
Type:
Single Family
Subdivision:
Osceola Court
Lot size:
0.38 Acres
Year built:
2004
A broker reciprocity listing Listing Provided Courtesy Of: KELLY PRICE & COMPANY LLC
View additional info

Stunning Winter Park Chain-of-Lakes estate. Only a short walk from Park Avenue, this five-bedroom pool home was custom built in 2004 with the finest materials and to the highest of standards and finishes. Brazilian Walnut and natural stone flooring is throughout the entire home. First floor amenities include a formal living room with fireplace, formal dining, a spectacular center-island kitchen overlooking the family room with stone fireplace, paneled library with fireplace and a gorgeous master suite with breath-taking views of Lake Osceola. The second floor features three large bedrooms, three full baths, and laundry. The fourth bedroom, also with a full bath, currently serves as a large playroom. The estate's lower level features large-screen media, billiards, wet bar, and private office. Windows throughout the lower level provide plenty of natural light! Outdoors is like you've never seen before. Gas lamps, a large pool, fountains, English gardens, motor court with three car garage and one of the longest and most beautiful views on the Winter Park Chain. Detailed Features List is available upon request.

$2,950,000

699 Osceola Avenue Winter Park, FL 32789

Beds:
5
Baths:
4.00
Sq.Ft.:
5,409
Status:
Active
MLS#:
O5308629
Type:
Single Family
Subdivision:
Town Of Winter Park
Lot size:
0.77 Acres
Year built:
1930
A broker reciprocity listing Listing Provided Courtesy Of: BHHS FLORIDA REALTY
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One of the original Winter Park Spanish Mediterranean estate homes built in 1930 to the Sinclair Oil family and noted in Winter Park history. This home has been renovated within its original design, authentic to every detail. Situated on Lake Osceola and part of the Winter Park chain of lakes it cannot be matched. Inside you will notice cypress woodwork, original tile, plaster walls, and all the details you would expect. Large rooms with expansive lake views including a large Master Suite downstairs. Upstairs four additional bedrooms all with privacy and views of the lake as well. Kitchen and bathrooms all renovated with today's modern requirements including a whole house generator system. Large yard with a large swimming pool and dock for your enjoyment of Lake Osceola. Call today for your private showing.

$2,900,000

847 Old England Avenue Winter Park, FL 32789

Beds:
4
Baths:
6.00
Sq.Ft.:
7,308
Status:
Active
MLS#:
O5169149
Type:
Single Family
Subdivision:
Golfview Terr
Lot size:
0.65 Acres
Year built:
2001
A broker reciprocity listing Listing Provided Courtesy Of: FANNIE HILLMAN & ASSOCIATES
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Walk to Park Avenue from one of Winter Park's crown jewels built by Maroon Fine Homes in 2001. Over 7300 square feet of perfection including 2 downstairs master suites, wonderful garden house, beautiful pool, large double lot, brand new gourmet kitchen.Gorgeous details in all rooms, Weathershield wood custom windows, eight Trane AC's, 3 separate water systems, central vac, Baldwin brass throughout home, Koehler top of line fixtures, conventionally framed using TJI's for all ceiling joists & rafters. 10' ceilings downstairs and 9' ceilings upstairs plus 9" baseboards.

$2,599,900

117 Genius Drive Winter Park, FL 32789

Beds:
6
Baths:
7.00
Sq.Ft.:
5,377
Status:
Active
MLS#:
O5172272
Type:
Single Family
Subdivision:
Ardmore/Windsong
Lot size:
0.93 Acres
Year built:
1991
A broker reciprocity listing Listing Provided Courtesy Of: KELLER WILLIAMS HERITAGE RLTY
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Winter Park lake front living at its finest. Elegant lake front estate on triple lot with private clay tennis court! Located in the sought-after Windsong Northshore area, this fabulous home is surrounded by grandfather oaks on a brick- lined street with tranquil pond and fountain across the street. This two story Palm Beach style home on 1 acre w/196' of lake frontage is equipped with a clay hydro tennis court, oversized pool, covered dock w/electric hoist. The prime Winter Park location on a quiet street just minutes from Park Avenue shops and restaurants. The next homeowner will love the private tennis court. Huge bay windows grace the master and living rooms with marble fireplaces, allowing panoramic views and sunsets on Lake Mizell. Wrought Iron spiral exterior staircase leads from pool to second floor balcony. Two bedrooms downstairs en-suite would make perfect nanny quarters or in-law suite. Fabulous unique bamboo style gourmet kitchen w/gas range and double ovens, built-in fridge w/separate large casual eating area overlooking lake. Built-in bookshelves in library/computer room. Several bedrooms have built-in furniture. This is truly a "one of a kind " Winter Park chain of lakes residence.

$2,499,500

531 Lake Front Boulevard Winter Park, FL 32789

Beds:
4
Baths:
6.00
Sq.Ft.:
5,194
Status:
Active
MLS#:
O5232055
Type:
Single Family
Subdivision:
Lords
Lot size:
0.56 Acres
Year built:
2009
A broker reciprocity listing Listing Provided Courtesy Of: RE/MAX SELECT
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A rare find dream home in an absolutely great location. Impeccable craftsmanship, luxurious comfort, privacy and unsurpassed elegancy is what makes this home perfect for a family. This rare find Rustic-Italian Tuscany Style home includes/ features a grand entry with a breathtaking view of the lake. Beautiful rounded staircase leading to second floor suites. Gourmet kitchen with two dish washers, professional chef's stove, huge hidden pantry with additional two refrigerators, with beautiful traditional style cabinets and granite counter tops. Loaded with countless details from tray ceiling, niches, hardwood floors, travertine, granite, wood trim, beams, and entertainment centers. Owner Suite on the main floor and second master suite both include Jacuzzi, built in closets, and a private balcony on the second floor suite. Second floor features family room with built in bar area, and additional laundry room. Numerous Elegant Architectural Details include: 4 private Balconies, 2 Covered Patios with Summer-kitchen and Gas fireplace, Salt Water Pool/Spa, and steam room. Private covered boat dock that includes boat and jet ski lift. Enjoy fantastic panoramic views of ski - Lake Killarney and breathtaking sunset views from almost every room in your house. Conveniently located to Winter Park Village Plaza, Park Avenue, Farmers Market, Rollins, Winter Park Country Club, I-4, Downtown Orlando.

$2,499,000

2219 Azalea Place Winter Park, FL 32789

Beds:
6
Baths:
8.00
Sq.Ft.:
6,684
Status:
Active
MLS#:
O5308505
Type:
Single Family
Subdivision:
Azalea Place
Lot size:
0.54 Acres
Year built:
2007
A broker reciprocity listing Listing Provided Courtesy Of: KELLER WILLIAMS HERITAGE RLTY
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Enjoy the Winter Park lifestyle in this gorgeous custom Lakefront home built by Liberty Development. Feels like new! Situated on the lagoon that feeds into Lake Maitland. Beautiful foyer entrance looking into the formal living room with luxurious floor toceiling fireplace and huge window overlooking pool and lake. Formal dining area with architectural columns and arches. Two wine cellars located off the foyer. Stunning staircase with rich hardwood flooring, iron railings, beautiful chandelier and wood ceiling. Gourmet kitchen with huge island, overlooking spacious family room, great for entertaining with wood beams plus large window looking out to spectacular water views and beautiful sunsets. Two master suites, one upstairs with a Juliet balcony and one downstairs, both with wonderful lake views. Six total bedrooms, six full baths and two half baths plus office located downstairs. Huge loft area with access to spacious balcony with great views. Bonus room adjoins the loft area with wet bar. Exercise room located on the third floor, could be used as a media room. Three car garage and a roof top spa with serene panoramic views of the lake! This spectacular home also features a Summer kitchen, pool and boathouse. Large lot on a quiet street. Walk or boat to the Winter Park Racquet Club.

$2,490,000

1167 Preserve Point Drive Winter Park, FL 32789

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
O5204823
Type:
Land
Subdivision:
Windsong Preserve Point
Lot size:
1.62 Acres
A broker reciprocity listing Listing Provided Courtesy Of: CENTURY 21 CARIOTI
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THINKING ABOUT BUILDING YOUR DREAM HOUSE? THERE IS NO BETTER PLACE! LOCATED IN DESIRABLE WINTER PARK, THIS LOT ABUTTS LAKE VIRGINIA. NEAR SHOPPING. A-RATED SCHOOLS. BEAUTIFUL LAKE BALDWIN IS JUST WALKING DISTANCE AWAY. CALL TODAY!

$2,399,900

861 Bonita Drive Winter Park, FL 32789

Beds:
6
Baths:
8.00
Sq.Ft.:
6,943
Status:
Active
MLS#:
O5194579
Type:
Single Family
Subdivision:
Comstock Park
Lot size:
0.56 Acres
Year built:
1999
A broker reciprocity listing Listing Provided Courtesy Of: HENIN REALTY
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Truly Exquisite Tuscan Beauty in the Heart of Winter Park With nearly 7,000 Square Feet of Living Space. This stunning Custom Estate features gorgeous Mediterranean architecture with a European flair.4 CAR GARAGE! This Luxury Retreat places you only minutes from Park Avenue's fine boutiques and bistros. Drive home to an unparalleled curb appeal. Grand circular driveway offers brick pavers and an exquisite stone fountain. Majestic hand carved solid wood double-door which sets the tone of quality products and strong attention to detail featured throughout this beautiful home. Magnificent foyer and an elegant living room separated by cast stone columns. Exotic coral-style Travertine flooring. Vibrant Venetian plaster compliments the walls. The well-equipped gourmet kitchen is a Chef's dream featuring custom cabinetry, GE Monogram natural gas cook top and oversized island with convenient second sink. Family room features stunning wood-beam ceilings, spectacular wood burning stone fireplace, chic bar and high-tech surround sound system. Drift away in the reclining chairs found in the state-of-the-art home theater. Commercial phone system integrated with fiber optic wiring. Entertain around the spectacular heated salt water pool and oversized spa. Detached living quarters over rear garage finished with hardwood flooring and newly renovated full bath. BE PREPARED...Commercial grade generator is ready to weather any storm! Exceptional opportunity for the most discriminating buyer!

$2,395,000

318 Genius Drive Winter Park, FL 32789

Beds:
5
Baths:
7.00
Sq.Ft.:
6,175
Status:
Active
MLS#:
O5302303
Type:
Single Family
Subdivision:
Windsong Lakeside Sec 02 43/71
Lot size:
0.47 Acres
Year built:
2005
A broker reciprocity listing Listing Provided Courtesy Of: KELLY PRICE & COMPANY LLC
View additional info

Spectacular, private estate in prestigious Windsong! Built in 2005 & featuring five bedrooms, five & two-half baths, this home boasts 6,175 SF of neoclassical inspired interior details. Grand two-story entry with stone columns invites guests into formal living & dining areas. Polished marble flooring, high ceilings, & magnificent wrought-iron staircase, combined with Illuminating natural light give this formal living area a palatial feel. Luxury continues throughout the home & into the designer kitchen, where solid wood cabinetry with hand-carved trimming, glass doors, granite countertops, & top-of-the-line chef’s appliances make this kitchen truly inspiring. Second living room off kitchen, has gas fireplace & built-in cabinetry with walk-thru to breakfast area & wet bar. Executive office, with floor to ceiling bookshelves & tray ceiling, maintain a studious environment for the professional in this home. Extravagant, downstairs master suite features lavish, two-story, solid-wood closet. Master bath leaves little to be desired with its jetted tub, large walk-in shower, & double vanities. Upstairs provides the perfect retreat for entertaining. Billiard room, with full bar overlooks downstairs living area, & home theater makes movie night at home a cinematic event. Three of the four upstairs bedrooms are generously sized & offer full bath, walk-in closets, & walk-out balcony. Resort style pool & spa, gazebo with summer kitchen, & covered patio exemplify outdoor living at its finest.

$2,375,000

2104 Venetian Way Winter Park, FL 32789

Beds:
4
Baths:
5.00
Sq.Ft.:
3,270
Status:
NEW LISTING
MLS#:
O5318679
Type:
Single Family
Subdivision:
Maitland Shores
Lot size:
0.41 Acres
Year built:
2010
A broker reciprocity listing Listing Provided Courtesy Of: FANNIE HILLMAN & ASSOCIATES
View additional info

Marvelous Craftsman revival on Lake Maitland...Newly constructed in 2010 with Old World character & charm! 1st place Parade of Homes winner for architectural woodwork: Meticulous craftsmanship combines with open bright floor plan that takes advantage of natural beauty of lakefront. Hardwood floors, copper clad bay windows, Arts & Crafts columns, tongue-&-groove cypress ceilings on both covered porches. Historic antique brick covers the exterior (& used inside for a warm dramatic effect) and flows onto classic white-columned porch, terrific for entertaining! Exceptional kitchen w/ fabulous architectural detailing, Carrera marble counters & a 4' x 9' peninsula, with a 2nd full size sink, 2 microwaves, gas cooktop, plus an arched pass-through to dining room & lake views. Two master suites! One master down with 3-tier closet; the upstairs master is entire 2nd floor, perfect for breakfast in bed overlooking Lake Maitland & Isle of Sicily, including sitting room & private lake-view balcony. Downstairs are 3 bedrooms with their own full baths, plus a Den & adjacent guest bath with claw foot tub. One bedroom has separate entry, private patio & access to 3-car garage, perfect for office or mother-in-law suite. Handcrafted floor-to-ceiling cabinetry surrounds a tiled fireplace with room for hidden TV & extra seating with storage beneath. Spectacular sunset views! New dock & boathouse. This home is like no other on the entire Chain of Lakes…it's understated, warm, richly detailed…a completely inspired gem.

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.
Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Copyright 2011, My Florida Regional MLS

32789 Real Estate Listings Provided By:

Real Living Good Neighbor Realty - A Berkshire Hathaway Affiliate
990 N. SR 434, Suite 1132
Altamonte Springs, FL 32714
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