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Winter Park FL Real Estate & Homes For Sale

394 Properties Found

The median home value in Winter Park, FL is $226,800. This is higher than the county median home value of $111,200. The national median home value is $152,300. The average price of homes sold in Winter Park, FL is $226,800. Approximately 58.04% of Winter Park homes are owned, compared to 31.7% rented, while 10.26% 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 394 Properties Displayed
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$6,995,000

1016 Genius Dr Winter Park, FL 32789

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 Listing Provided Courtesy Of: 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.

$6,950,000

802 Georgia Ave Winter Park, FL 32789

Beds:
4
Baths:
5.00
Sq.Ft.:
6,372
Status:
Active
MLS#:
O5113660
Type:
Single Family
Subdivision:
Winter Park Old Town
Lot size:
3.25 Acres
Year built:
1930
A broker reciprocity listing Listing Provided Courtesy Of: FANNIE HILLMAN & ASSOCIATES
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ELEGANT LAKEFRONT ESTATE in the heart of downtown Winter Park! This magnificent showplace estate home is located on 3 lush acres with sweeping views of Lake Osceola and easy walking distance to Park Avenue. The main residence was originally built in 1930, totally renovated in 1994 and then had major additional updating in 2005. New embellishments include remodeled kitchen, covered walkway from the garage to the main house, all new landscaping and irrigation, new boat dock, new tennis court, 6 new AC units including ductwork, new windows in main house, new alarm system and much much more. This one-of-a-kind estate includes a fabulous 1931 square foot 3 bedroom 3 bath guest house with living room and kitchen. Additionally, there is a 1 bedroom 1 bath caretaker's cottage with 582 square feet. Numerous features include koi pond, 3 car garage, tennis court, Jacuzzi, dock with boat house, large dry basement. This luxurious gated showplace is a dream come true for the right buyer. It retains the old world feel of the 1930's with all the comforts of the new millennium.

$6,600,000

240 Trismen Ter Winter Park, FL 32789

Beds:
7
Baths:
11.00
Sq.Ft.:
8,000
Status:
Active
MLS#:
O5138786
Type:
Single Family
Subdivision:
Brewer E H
Lot size:
1.41 Acres
Year built:
1901
A broker reciprocity listing Listing Provided Courtesy Of: REGAL R.E. PROFESSIONALS LLC
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This beautiful lakefront home brings history and the present day together and will simply take your breath away. Situated in the quaint community of Winter Park it is only one of two houses listed on the "National Register of Historic Places". Surrounded by lavish grounds the extensively updated and renovated home is waiting for the perfect family. Whether you want to spend time enjoying the comforts of your own home by relaxing on your wraparound porch, playing a game of pool, enjoying a movie in your private home theatre or being out on Lake Osceola, this house will cater to those needs. The light and airy Kitchen, usually the hub of any home, has plenty of room with its open floor plan, which the chef of the family will simply adore. A 3500sq ft. ventilated attic gives you the opportunity to add your own touch to the house by converting it into whatever your heart desires, the possibilities are endless! After enjoying the wonderful community of Winter Park, relax and take in the views of the Lake from your master suite or star gaze from the unique widow's balcony, located on the roof of the home. This lovely estate has plenty to offer and is waiting for you!!

$6,000,000

N 909 N Wymore Rd Rd Winter Park, FL 32789

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
O5152153
Type:
General Commercial
Lot size:
1.21 Acres
A broker reciprocity listing Listing Provided Courtesy Of: PRIMESTATE REALTY, INC.
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GOOD LOCATION, GOOD PROPERTY IN WINTER PARK, LICENSE FOR 95 BEDS. ALF, UPDATED ROOF, UPDATED ELECTRIC, UPDATED FIRE ALARM SYSTEM, UPDATED PLUMBING, UPDATED FLOORING.

$5,995,000

235 Genius Dr Winter Park, FL 32789

Beds:
5
Baths:
6.00
Sq.Ft.:
9,425
Status:
Active
MLS#:
O5161813
Type:
Single Family
Subdivision:
Windsong Lakeside Sec 2
Lot size:
1.04 Acres
Year built:
2003
A broker reciprocity listing Listing Provided Courtesy Of: GLOBAL REALTY ACQUISITIONS INC
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This Italian inspired waterfront estate is located on Lake Mizell, on the Winter Park chain of lakes in the exclusive Windsong community. Situated on 1+ Ac boasting 200ft of lake frontage w/magnificent views and sunsets, this home radiates splendor while still reflecting warmth and elegance. The residence was featured in Dreamhomes Florida, an exclusive showcase of Florida's finest Architects, Designers, and Builders. This custom one-owner home has beautiful architectural features and one of a kind exquisite details including groin vaulted, barreled, and gold leaf and hand painted ceilings, Venetian plaster and custom wall coverings, custom cabinetry, two story custom wood master closet and professionally organized secondary closets. 5 custom stone fireplaces. Travertine, marble and wood floors. Gourmet kitchen has 6 burner gas stove, double ovens, island, bar, walk-in pantry w/second refrigerator, breakfast nook, brick courtyard w/fountain and kitchen office. Wine room and wet bar off living and dining room, upstairs/downstairs family rooms, entertainment/music room w/full bar, bonus room, 5 bedroom suites, luxurious downstairs master bedroom w/fireplace and sitting room. Covered outdoor living area w/summer kitchen, custom disappearing edge pool. Outdoor spa, fountain, outdoor wood burning fireplace. Covered boat dock, and waters ports area w/jet ski platform and electric boat lift. Other features include 40KW natural gas generator, lightning suppression system, internet based camera security system.

$3,399,000

110 Osceola Ct 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
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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.

$3,275,000

1400 N New York Ave Winter Park, FL 32789

Beds:
4
Baths:
6.00
Sq.Ft.:
5,656
Status:
Active
MLS#:
O5146644
Type:
Single Family
Subdivision:
Winter Park
Lot size:
1.03 Acres
Year built:
1977
A broker reciprocity listing Listing Provided Courtesy Of: KELLY PRICE & COMPANY LLC
View additional info

Chain of Lakes Executive Estate with Amazing Guest House nestled in the Heart of Olde Winter Park. Sprawling property offers panoramic views of beautiful Lake Maitland. Elegant home remodeled in 2001 boasts a spectacular Master Suite With His & Her Bathrooms and walk-in closets, soaring ceilings in Foyer & Formal Rooms, smartly appointed Gourmet Kitchen with cozy breakfast nook, Family Room with exquisite millwork, built-ins & gas fireplace. The 26x17 downstairs bonus room perfect for your home office/library, game room or In-Law Suite. PLUS incredible Guest House above detached 3 Car Garage includes vaulted ceilings, large Bedroom/Bath and full Kitchen. Stunning back yard oasis complimented with manicured landscaping, amazing patio for entertaining, stone enhanced waterfront & boat dock with hoist. Walk to Park Avenue from this serene cul-de-sac location. Lakefront Living at it's Finest!

$3,199,000

1761 Pinetree Rd Winter Park, FL 32789

Beds:
5
Baths:
6.00
Sq.Ft.:
5,042
Status:
Active
MLS#:
O5152708
Type:
Single Family
Subdivision:
Sicilian Shores
Lot size:
0.76 Acres
Year built:
1998
A broker reciprocity listing Listing Provided Courtesy Of: WINTER PARK LAND CO.
View additional info

Lake Maitland custom home with breathtaking views from every room. This home was built by Gallimore.. It has a very open floor plan.. the double doors at the entrance invite you into the foyer which opens into the living room with very high ceilings. The family room has a fireplace and very nice wood built ins...the kitchen is very spacious with panty and lots of room for storage. There are doors from the living and family room that take you to a very nice pool area that is screened. The master is down with views of the lake...very spacious with a sitting area and lovely master bath...there is also a wonderful office with beautiful wood cabinets....the laundry and mud room are down...there are three bedrooms up stairs with their own baths...Their is a boat house & dock...Winter Park "A" schools..

$3,195,000

1008 Anchorage Ct Winter Park, FL 32789

Beds:
5
Baths:
7.00
Sq.Ft.:
8,973
Status:
Active
MLS#:
O5031991
Type:
Single Family
Subdivision:
Anchorage Ests
Lot size:
0.59 Acres
Year built:
2007
A broker reciprocity listing Listing Provided Courtesy Of: STOCKWORTH REALTY GROUP
View additional info

Coastal Living in Winter Park, Enjoy this 'Santa Barbara' style home with expansive rooms detailed with river washed wood beams, Peruvian travertine and a reclaimed terra cotta roof.This fully furnished show place by Montanna & Associates boasts 5 bedrooms, includes 2 master suites, 5 full and 2 half baths, pool with fire pots, outdoor cigar terrace adjoining the gentlemen's lounge with theatre, and an extraordinary kitchen with every amenity. This fully gated estate is situated on a .58 acre lot, and offers a 3 car garage and extended parking space on a Chinese quartzite driveway. There is a Lutron lighting system, a 1200 bottle wine room, Hurd windows and the home is prewired foran emergency generator with a load management panel. Materials include onyx, Peruvian travertine, granite, copper clad tub, and casement windows. The master suite has a beautiful view of the gardens and the master bath features a rain shower, warming drawer for towels, and an oversized closet with organizers. A hidden passage to the office completes the master wing. A second master suite is located upstairs along with 3 guest suites; all complete with crown moulding, niches, and beautifully detailed baths. Outdoor living includes a pool with water deck, swim shelf and fire pots. There is ample room for pets. Enjoy the evening in the outdoor kitchen, on the cigar terrace or around the fire pit all within walking distance of Park Ave.

$3,125,000

751 Bonita Dr Winter Park, FL 32789

Beds:
4
Baths:
6.00
Sq.Ft.:
5,390
Status:
Active
MLS#:
O5104987
Type:
Single Family
Subdivision:
Comstock Park
Lot size:
0.46 Acres
Year built:
1984
A broker reciprocity listing Listing Provided Courtesy Of: COLDWELL BANKER RESIDENTIAL RE
View additional info

Sensational English Manor located on Lake Osceola with magnificent long sunset views... Extensively remodeled & expanded in 2003, this award winning home has tremendous character & charm thruout... Olde World features, extensive moldings & detailed craftsmanship combined with all the conveniences and openness of today's desired floor plans with great entertaining spaces... gorgeous hardwood, stone & marble floors, beautiful stained glass windows, generous room sizes, very high ceilings & casement windows... Spacious grand salon with cathedral ceiling, walnut paneled walls & beams with over sized marble fireplace & 12' high windows overlooking the pool and lake, 1st floor Master retreat with fireplace & sitting area, plus 3 more large bedroom suites, separate gentleman's library, "Aurora Award" winning chef's kitchen w/ top grade appliances including: 48" gas range, warming drawer, 2 dishwashers, beverage center, ice maker, 2 ovens & counter top bar open to fabulous family room with a wall of glass looking out to picturesque lake views, pool area & yard... Note: 3 car garage consist of an oversized 2-car garage & porte-cochere that could be easily enclosed... located on a "chain of 6 lakes"... This home has been published in Orlando Magazine, Orlando Sentinel and Kitchen & Bath Design News...

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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

Winter Park FL Real Estate Listings Provided By:

Real Living Performance Realty International
990 N. SR 434, Suite 1132
Altamonte Springs, FL 32714
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