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Winter Park FL Real Estate & Homes For Sale

372 Properties Found

The median home value in Winter Park, FL is $297,100. This is higher than the county median home value of $149,700. The national median home value is $170,100. The average price of homes sold in Winter Park, FL is $297,100. Approximately 55.69% of Winter Park homes are owned, compared to 32.84% rented, while 11.47% 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.


1 - 10 of 372 Properties Displayed
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Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
O5359502
Type:
Other
Lot size:
6 Acres
Year built:
1958
A broker reciprocity listing Courtesy: THE SYDGAN CORP
View additional info

PROJECT: Ravaudage is a to-be-developed, 75-acre, mixed-use, transit oriented development located partially in Maitland and partially in Winter Park, Florida. The Project will include 891,000 s.f. of Class A Office, 323,000 s.f. of Commercial/Retail, 489 Market Rate, Assisted and Age-Restricted Residential Units, 320 Hotel Rooms, a 45,000 s.f. Performing Arts Center, 80,000 s.f. of Self-Storage, public parks and a multimodal Phase II Commuter Rail Village. LOCATION: The Project is located on the northwest corner of Lee Road and North Orlando Avenue (US 17-92), primarily in unincorporated Orange County, Florida, bordered by Bennett Avenue on the west and extending north to just south of Lake Avenue. The adjacent CSX rail line forms the northern border of the site and will service the recently approved Central Florida Commuter Rail. The site enjoys unobstructed access to Lake Gem and Park Lake. The site is within two miles of the downtowns of Winter Park (32789 zip code), Maitland and Eatonville and Interstate 4 (I-4). Adjacent land uses are primarily commercial and multi-family. CURRENT SITE CONDITION: The Property is currently a mix of single family residential, commercial and vacant land. Soil and environmental assessments have been completed.

Beds:
6
Baths:
9.00
Sq.Ft.:
10,314
Status:
Active
MLS#:
O5162608
Type:
Single Family
Subdivision:
Windsong Ests Sec 1
Lot size:
2.2 Acres
Year built:
2005
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES
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As beautiful inside as it is outside, this magnificent one-of-a-kind lakefront estate is located in the Gated Estate Section of Windsong, one of Winter Park's most desirable addresses. This custom one-owner home was built in 2005 by award-winning Rial Jones and designed by Bernie Johnson. The 2+ acre estate is surrounded by water on both sides, with Lake Mizell in the front and Lake Virginia in the rear, with the back illuminated at night by Rollins College and downtown Orlando. The floor plan is masterfully laid out with 6 bedroom suites plus an office suite, media room, and many bonus areas. Features include ceilings artfully designed with wood beams and exquisite detail; coquina baseboards; Venetian plaster and sueded walls; professionally organized closets; custom carpentry; travertine and distressed wood floors; and meticulous detail and top of the line amenities in every room. Gourmet kitchen has 6 burner gas stove, double ovens, uniquely designed wood burning grill, 2 dishwashers, and adjacent butler's pantry with 3rd dishwasher plus attached wine room. Upstairs and downstairs laundry. Downstairs master suite overlooks lake and has gas fireplace, attached sitting room, and walk-in closet "rooms", plus His & Her sinks and toilet rooms. Four themed bedroom suites upstairs also include attached offices for each. Backyard includes pool with water features, 1260sf covered lanai with gas fireplace and summer kitchen, all overlooking lush lawn and lake. Truly one of the finest homes in Central Florida.

Beds:
5
Baths:
7.00
Sq.Ft.:
8,738
Status:
Active
MLS#:
O5217018
Type:
Single Family
Subdivision:
Town Of Winter Park
Lot size:
2.13 Acres
Year built:
1925
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES
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A once in a lifetime opportunity to own a 1925 historic estate on one of Winter Park's most beautiful streets, steps to downtown Park Avenue. This property sits on over 2 acres with amazing views of Lake Osceola and professionally landscaped grounds. Amenities include original wood floors, original staircase & banister, chandeliers, crown molding, high ceilings, wood burning fireplaces & French doors. Living spaces are large and accomdating with great flow for entertaining. Updated kitchen. Billiard room, office, music room, den/family room & powder bath are also located on the main level of this estate. Second floor features an elegant master retreat with private sun deck, screened porch & updated bath as well as 4 additional spacious bedrooms, three baths, an office & a hobby room. Third floor features a huge bonus room. The backyard feels like a luxury spa with amazing lake views, cabana & summer kitchen, screened lanai, and newly renovated heated pool/spa. Expansive lake frontage is complete with volleyball court & boat dock.

Beds:
5
Baths:
8.00
Sq.Ft.:
7,800
Status:
Active
MLS#:
O5365962
Type:
Single Family
Subdivision:
The Ellno Willo
Lot size:
1.59 Acres
Year built:
1925
A broker reciprocity listing Courtesy: KELLY PRICE & COMPANY LLC
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Majestic Winter Park Estate on 1.59 acres of pristine lakefront property. Panoramic views of Lake Virginia from every corner of this stunning home. Private driveway with electronic gate, motor court, four car garage, guest house, boathouse, and more. Sophisticated and elegant, the main house offers four bedrooms, three full baths, two half baths, formal living and dining rooms, family room, a Chef’s kitchen with professional grade appliances, home office, and gym. Screened in lanai, trellis covered patio, and open back porch all overlook the meticulously cared for lawn and gardens, complimented by hanging moss oaks and towering palms. Enjoy breathtaking sunset views over the estate’s rolling hills. Originally built in 1925, this is a very rare opportunity to own one of Winter Park’s most significant estates, offering exclusive privacy and priceless lakefront views.

Beds:
6
Baths:
9.00
Sq.Ft.:
10,190
Status:
Active
MLS#:
O5344588
Type:
Single Family
Subdivision:
Woodmere Terr Rep
Lot size:
1.01 Acres
Year built:
2000
A broker reciprocity listing Courtesy: COLDWELL BANKER RESIDENTIAL RE
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Premier lakefront estate in the heart of the Vias on Lake Maitland and built by Charles Clayton Construction... This Winter Park Chain of Lakes estate takes advantage of the elevated topography. Inspired by the magnificent transitional estate homes of the Northeast, this home boasts panoramic views of Lake Maitland with 120' of water frontage on over an acre lot. There are 5 en suite bedrooms, 8 baths in the main house, plus a detached 1 bedroom/1 bath full guest apartment over the three car garage. Downstairs commences with a grand entry overlooking the lake thru an impressive 2-story living & music room, guest suite, gentleman's library, dining room, butler's pantry, and an elegant chef's kitchen open to the gathering room and breakfast room with 2-story beamed ceilings. Upstairs is highlighted by an expansive private master retreat with luxurious bath & dressing area, along with a wonderful "tree-top" sitting room to enjoy the elevated views of the lake. Additionally, you will find 3 more bedroom suites, large bonus room, and laundry room. Outdoor living spaces include a 2-story screened in sitting room, multiple covered lanais around the pool area, summer kitchen, and a beautiful winding path down to a boat house with storage room. There are top quality finishes inside and out including Pella windows & doors, oak hardwood floors, extensive trim & detailed craftsmanship, and Monier tile roof. Walking distance to the WP Racquet Club and Park Avenue!

Beds:
5
Baths:
7.00
Sq.Ft.:
6,850
Status:
Active
MLS#:
O5227790
Type:
Single Family
Subdivision:
Boiley Green
Lot size:
0.98 Acres
Year built:
1999
A broker reciprocity listing Courtesy: PARKLAND INTERNATIONAL REALTY
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Enter the private gate to find this magnificent home with interior design by Betsy Godfrey along the shores of Lake Maitland. Outstanding features adorn this 2006 totally remodeled home. The front door opens to this beautiful open floor plan drawing your attention past the Dining Room to a most beautiful view of Lake Maitland. Foyer leads to an attractive Office with fireplace and custom built in shelves and an open Living Room, currently enjoyed as a Music Room, with piano and seating. Large Family Room with another gas fireplace and a wall of windows overlooks the pool and lake. Kitchen features double refrigerators, gas cook top, wine refrigeration cellar, center island and a breakfast area with built in desk. Off the Kitchen is a Guest Suite with full bath. Toward the back of the home is a Gathering Room with a wet bar and more views of the lake through floor to ceiling windows. The Master is located downstairs with a large Master Bath and closets. Electric shades can be open or shut with the push of a button. Upstairs hosts three en suite Bedrooms, one currently used as a Media Room. An added bonus is located between two bedrooms and currently used as an Art Studio, also perfect for a writer or convert to a playroom, with a scenic view of the lake. The outside area has a wrap around terrace with a Summer Kitchen off the Family Room and a Gathering Area off the Master with another gas fireplace. Dock includes a covered Boat House with hoist. Please view the virtual tour.

Beds:
5
Baths:
8.00
Sq.Ft.:
8,410
Status:
Active
MLS#:
O5318828
Type:
Single Family
Subdivision:
Winter Park
Lot size:
1.15 Acres
Year built:
2014
A broker reciprocity listing Courtesy: COLDWELL BANKER RESIDENTIAL RE
View additional info

Step into this dramatic Mid-Century Modern home and you'll never want to leave. Enjoy the perfection of the white glass porcelain floors and dramatic windows, as you overlook the spectacular courtyard from every room. Entertain large parties simply with the spacious and commercial grade kitchen, grand family and living rooms, and resort-like courtyard. Display art, cars, or RVs in the oversized heated and air-conditioned garage space with over 20 ft. of ceiling height (with space for 19 cars). And, with the push of one button, activate the external shades to cover all exterior windows, doors, and garage doors, providing the ultimate in security and privacy. This one-of-a-kind contemporary masterpiece on 1.15 acres in the heart of Winter Park is the ultimate in design, privacy, luxury, and security.

Beds:
5
Baths:
8.00
Sq.Ft.:
8,990
Status:
Active
MLS#:
O5350779
Type:
Single Family
Subdivision:
Cloister Grove
Lot size:
0.76 Acres
Year built:
2010
A broker reciprocity listing Courtesy: COLDWELL BANKER RESIDENTIAL RE
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Spanish Mediterranean style with fabulous courtyard design perfect for entertaining, this home is in “like new” condition w/ bright, modern-transitional interiors with gracious room sizes along with the finest of finishes & detail. Features include exquisite light fixtures, exotic granite/marble counters, incredible custom olde world doors, hand crafted cabinetry, elegant walnut & antique pine hardwood floors, wonderful chef’s open island kitchen with butler's pantry, wine cabinet, desk work station & separate breakfast room overlooking courtyard and pool… elegant generous formal dining & living rooms, gas fireplaces, gentlemen's library… and expansive master suite with sitting area, his & her separate dressing areas w/ terrific closets, shoe closet and lavish “spa like” bath. Bright and open custom floor plan provides great spaces for entertaining large parties or intimate evenings inside or out. 2 additional 1st floor bedroom suites including guest suite detached from the main residence “casita” offering you and your guest plenty of privacy. Upstairs enjoys the 2 additional secondary bedroom suites, a media rm w/ theater, multiple balconies overlooking the courtyard and "resort style" pool & heated spa. This home is designed for outdoor living area with summer kitchen, multiple lanais and terraces, extensive gorgeous iron work, outside shower, swim up seats built into the luxurious pool and more... Truly a special estate property on oversized lot in a sought after premier Via’s setting!

Beds:
4
Baths:
5.00
Sq.Ft.:
5,731
Status:
Active
MLS#:
O5333705
Type:
Single Family
Subdivision:
Acreage & Unrec
Lot size:
0.7 Acres
Year built:
1989
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES
View additional info

Unquestionably one of the most elegant, sophisticated and delightful lakefront homes in all of Winter Park. Situated on Lake Osceola and the Winter Park chain on a beautiful tree-lined street, only blocks from Park Avenue and all that downtown Winter Park has to offer. Although built in 1989, this home has a historic feel that oozes warmth, luxury and charm. This home has been totally renovated with the very best in quality including enormous brand new gourmet kitchen in 2009, all new AC’s, new Heart of Pine floors throughout, all new LED lighting and much more. Grand entrance foyer, kitchen open to large family room with built-ins and gorgeous details, breakfast room with incredible lake views, formal living room with gas fireplace, paneled library including wine room and separate office. Stunning master suite situated lakefront on the 2nd floor plus additional bedroom suite both open to grand covered balcony. 3rd bedroom suite has separate staircase and 4th bedroom suite is accessible by private elevator to the third floor. Lushly landscaped grounds including private courtyard, dock and covered boathouse with entertaining room. A truly one of a kind home for the most particular buyer.

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 Courtesy: 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.

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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 2015, My Florida Regional MLS

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