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Winter Park, FL Real Estate — Homes For Sale in Winter Park, FL

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Winter Park Real Estate Overview

Originally founded as a resort destination by affluent New Englanders in the late 1880s, Winter Park is today known for its majestic trees, beautiful parks, brick-lined streets, stunning homes, a private liberal arts college, educational museums, sparkling lakes, and amazing shops. Winter Park is located just 15 minutes from the...
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$224,000
$868/mo
Monthly Payment:
$868
Principal & Interest:
$829
HOA Dues:
$39
(Based on a 30 year fixed loan at 3.75% with $44,800 down)
Winter Park, FL 32792
Seminole County School District
4bed 3bath 1,840sq ft $122 / sq ft SFR
Lot Size6,410sq ft Built1985 On Site41days
Short sale. Walk the kids to a rated schools, play in the park, enjoy the tennis courts or fish off the dock on serene lake florence. Country lane is a friendly neighborhood in... more
Short sale. Walk the kids to a rated schools, play in the park, enjoy the tennis courts or fish off the dock on serene lake florence. Country lane is a friendly neighborhood in the heart of east winter park. This well-maintained 2 story home has 4 beds/2.5baths with updated kitchen and baths. Beautiful wrought iron railings makes the entry open and elegant. New laminate flooring in the living, dining, and up the stairs. Tiled screened porch leads to tropical backyard, gazebo for entertaining and a cute shed that can be used as a play house or extra storage.Sprinkler system is on a well and timer. Ac is under warranty until 2017. Come look at your new home! less
Listing Provided Courtesy of Charles Rutenberg Realty
Popularity
Your search results are current and complete. Learn more
$74,900
$349/mo
Monthly Payment:
$349
Principal & Interest:
$277
HOA Dues:
$72
(Based on a 30 year fixed loan at 3.75% with $14,980 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,284sq ft $58 / sq ft TWN
Lot Size3,048sq ft Built1979 On Site41days
Interior unit in Windward Square offers the same gated courtyard entry featured throughout this terrific community. Step inside to a truly unique layout that includes a large... more
Interior unit in Windward Square offers the same gated courtyard entry featured throughout this terrific community. Step inside to a truly unique layout that includes a large kitchen/dining combo w/all appliances, laundry closet, and a gorgeous Zen pond and brick walls opening up to the sky! Home also features a large living room, enclosed porch, small backyard, and split-planned bedrooms that include 2 bedrooms and a shared bathroom off of the living room and a master suite w/full, handicap modified bathroom off of the kitchen area. Loads of amenities including shuffleboard, picnic/BBQ areas, and a community pool are offered in this community. It's all about location with this unit. Live within minutes of local public schools, Full Sail University, and tons of restaurants and shops. Plus, this is a very easy drive to UCF and Seminole State! Why pay high room and board when you can own! less
Listing Provided Courtesy of 100% Real Estate, Inc
Popularity
$2,195,000
$11,722/mo
Monthly Payment:
$11,722
Principal & Interest:
$8,132
HOA Dues:
$3,590
(Based on a 30 year fixed loan at 3.75% with $439,000 down)
Winter Park, FL 32789
Orange County School District
3bed 5bath 4,090sq ft $537 / sq ft CND
Lot SizeN/Asq ft Built2005 On Site43days
Downtown Winter Park premier luxury condominium building… adjacent to new Alfond Inn hotel, walk to Park Ave and Rollins College… This is arguably the best located... more
Downtown Winter Park premier luxury condominium building… adjacent to new Alfond Inn hotel, walk to Park Ave and Rollins College… This is arguably the best located unit in the building on the West end with sunset and downtown Winter Park & Orlando views plus Interlachen Ave, Alfond Inn, Rollins College & tree top views … The most desired "A" (end) unit in the building. Exquisitely finished, hardwood floors in main living areas, wetbar and kitchen/gathering room, custom oversized island kitchen with solid wood cabinets, a fireplace & additional cabinets unique to this unit, extensive crown, tall base moldings & built-ins throughout , completely redesigned master-suite w/ oversized closets and separate his/her baths, enlarged custom designed laundry room… open bright floor plan with lots of great windows/doors to enjoy panoramic views and multiple terraces… split bedroom plan with large, lavish private master retreat... 2 premium assigned parking spaces & a potential 3rd parking space for discussion with contract... This luxurious building offers wonderful amenities including great entertaining rooms, 24/7 security, on site manager & staff for complete concierge services and lifestyle to enjoy downtown Winter Park living at its best!! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$599,000
$2,219/mo
Monthly Payment:
$2,219
Principal & Interest:
$2,219
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $119,800 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size16,140sq ft BuiltN/A On Site43days
Large corner lot in park grove - 16,138
Large corner lot in park grove - 16,138 less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity N/A
$375,000
$1,389/mo
Monthly Payment:
$1,389
Principal & Interest:
$1,389
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $75,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,869sq ft $201 / sq ft SFR
Lot Size37,300sq ft Built1959 On Site43days
One of a kind 135' of spring fed Lake Ann frontage. Never will there be an opportunity like this one in our lifetimes. But here it is this one is ready for you to update the way... more
One of a kind 135' of spring fed Lake Ann frontage. Never will there be an opportunity like this one in our lifetimes. But here it is this one is ready for you to update the way you want it. And the seller has considered that when they priced it. The views of the lake from the home are breath taking. And the best part its over 3/4 of an acre. Call today for your private showing you wont be disappointed. less
Listing Provided Courtesy of Re/max 200 Realty
Popularity
$592,500
$2,195/mo
Monthly Payment:
$2,195
Principal & Interest:
$2,195
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $118,500 down)
Winter Park, FL 32789
Orange County School District
5bed 3bath 3,231sq ft $183 / sq ft SFR
Lot Size15,974sq ft Built1957 On Site43days
Appraised at $566,000 in dec. 2013. Closets and storage galore are just one highlight of this highly desirable timberlane shores gem. Spacious 5 bedroom, 3 bathroom pool home on... more
Appraised at $566,000 in dec. 2013. Closets and storage galore are just one highlight of this highly desirable timberlane shores gem. Spacious 5 bedroom, 3 bathroom pool home on a corner lot located in the heart of winter park. Large formal living and dining rooms. Bright and airy family room and eat-in kitchen with breakfast bar, both overlooking the pool. All bedrooms have ample closet space, including master walk-in. Two wood burning fireplaces (one in master) and original built-ins complete this unique home. Mature trees and landscaping grace the .37 acre lot which also includes a two-car, side-entry garage and a 10 x 12 shed with attic storage. Recent upgrades include: new hot water heater, 2 new high-efficiency ac systems with digital thermostats, new electrical service panel, new insulation throughout, new air conditioning duct-work and the home has been re-piped. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$749,000
$2,807/mo
Monthly Payment:
$2,807
Principal & Interest:
$2,774
HOA Dues:
$33
(Based on a 30 year fixed loan at 3.75% with $149,800 down)
Winter Park, FL 32792
Seminole County School District
4bed 3bath 3,287sq ft $228 / sq ft SFR
Lot Size1.2acre Built1986 On Site43days
Winter Park lakefront living at its best! This beautiful Key West style home has direct lake frontage with boat dock and lift on spectacular private Bear Gully Lake. The home... more
Winter Park lakefront living at its best! This beautiful Key West style home has direct lake frontage with boat dock and lift on spectacular private Bear Gully Lake. The home offer 4 bedrooms and 3 full baths, wood burning fireplace, beautiful wood work, island kitchen open to the family room with vaulted ceilings, updated master bathroom, expansive air conditioned “Florida Room” for taking advantage of the long lake views, and an updated kitchen with granite countertops. Exterior features include a large back yard with room for a pool and plenty of space for entertaining and taking advantage of all water sports. Bring your ski boat, wave runners, paddle boards, and kayaks and take advantage of this opportunity to own a lakefront home in Winter Park. Located on a quiet cul-de-sac and easy access to downtown Winter Park or downtown Orlando. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$1,095,000
$4,056/mo
Monthly Payment:
$4,056
Principal & Interest:
$4,056
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $219,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,263sq ft $257 / sq ft SFR
Lot Size11,718sq ft Built2005 On Site43days
This is a rare opportunity to own a 5 bedroom custom home in the heart of the Winter Park “Tree Street” neighborhood. This 2005 built home has all the modern... more
This is a rare opportunity to own a 5 bedroom custom home in the heart of the Winter Park “Tree Street” neighborhood. This 2005 built home has all the modern amenities for your most discriminating buyer. Tons of natural light and vaulted ceilings in the family room are just a few of the features offered by this home. Downstairs includes separate office, laundry room, formal dining, and eat-in kitchen. Other interior features are gorgeous Brazilian cherry hardwood floors, large downstairs master suite, a second downstairs bedroom suite, wonderful chef’s island kitchen complete with granite countertops, stainless appliances, temperature controlled wine storage, gas range, and solid wood cabinets. Out back you will find a large inviting pool with plenty of areas for full sunlight or shade perfect for entertaining day or night. Above the garage is a large bonus room currently used for storage, but can be converted to game room, guest suite, or office. Perfectly located with easy access to the Park Avenue retail district, Winter Park YMCA, Rollins College, and also a short commute to UCF and downtown Orlando. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$700,000
$2,593/mo
Monthly Payment:
$2,593
Principal & Interest:
$2,593
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $140,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,400sq ft $206 / sq ft SFR
Lot Size11,476sq ft Built1995 On Site43days
End of Summer Special! Reduced Again - Extremely motivated Seller – will review all offers. 3,400 square feet – four bedrooms, three baths, and an oversized bonus... more
End of Summer Special! Reduced Again - Extremely motivated Seller – will review all offers. 3,400 square feet – four bedrooms, three baths, and an oversized bonus room above the garage. New roof with warranty (2012) – new A/C (2014) – new plumbing (2013). Updated kitchen with granite countertops and stainless steel appliances. Great schools! Desirable neighborhood, tucked behind Park Grove. Minutes to Park Avenue, the Winter Park Golf Course, the Racquet Club, and Hannibal Square. Easy to show and available for a quick close. One of the lowest price/square foot homes in 32789 – don’t miss out! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$3,300,000
$12,226/mo
Monthly Payment:
$12,226
Principal & Interest:
$12,226
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $660,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 7,351sq ft $449 / sq ft SFR
Lot Size15,570sq ft Built2004 On Site44days
The Dream Estate! Your opportunity to own a masterpiece! This classic estate offers elegance, luxury and entertainment in the heart of desired Winter Park. With just a short... more
The Dream Estate! Your opportunity to own a masterpiece! This classic estate offers elegance, luxury and entertainment in the heart of desired Winter Park. With just a short walk from all the fine restaurants and shopping on Park Avenue. As you enter this home you will be mesmerized with the attention to details given by the award winning builder's team Maroon Fine Homes & Marquis Fine Homes. The 3 story home features on the main level a formal living room with fireplace, family room, dining room, study, master bedroom and a gourmet kitchen with professional appliances. As you step into the temperature controlled lanai you will find an additional fireplace, summer kitchen and electronic hurricane shutters. Backyard offers room for outdoors entertaining, heated pool/spa and outdoor fireplace. You can take the fully operational elevator to the base level where you will find a fully equipped gym, climate controlled wine cellar, full wet bar, game room, movie theatre and 2 full suites. The home's top level features additional living space and 2 full suites. No description or photos can make justice to this stunning property. less
Listing Provided Courtesy of Bhhs Florida Realty
Popularity
$315,000
$1,167/mo
Monthly Payment:
$1,167
Principal & Interest:
$1,167
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $63,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,532sq ft $206 / sq ft SFR
Lot Size6,512sq ft Built1977 On Site44days
Seller's are motivated to sell!!! This perfect Winter Park location is only minutes to the iconic Park Ave. This property is surrounded by million dollar homes and sits on a... more
Seller's are motivated to sell!!! This perfect Winter Park location is only minutes to the iconic Park Ave. This property is surrounded by million dollar homes and sits on a corner lot. 3 bedrooms 2 full baths, attached one car garage, 1532 total square feet. Carpet in bedrooms, tile in kitchen and bathrooms. This property would make a great starter home or the perfect retirement home with the convenience of hospitals and medical centers close by. less
Listing Provided Courtesy of Olde Town Brokers Inc
Popularity
$675,000
$2,500/mo
Monthly Payment:
$2,500
Principal & Interest:
$2,500
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $135,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,638sq ft $256 / sq ft SFR
Lot Size11,933sq ft Built1997 On Site44days
Desirable single story home, with three bedrooms, three full baths, and guest apartment in the heart of Winter Park! Located on a quiet circle, minutes from Park Avenue and... more
Desirable single story home, with three bedrooms, three full baths, and guest apartment in the heart of Winter Park! Located on a quiet circle, minutes from Park Avenue and nearby shops and dining, this home has a fantastic floor plan and offers over 2,600 square feet of living space, with formal living and dining, a large family room off the kitchen, and French doors that lead to the resort style pool and spa. Beautiful hardwood flooring has been laid throughout the home. Master bedroom is the perfect retreat with its vaulted ceilings, and en suite with his and her walk-in closets, double vanity, garden tub and shower. Each guest bedroom is generous in size and has their own private bath. Spacious kitchen with new GE appliances features travertine flooring, an over-sized closet pantry, bar-top seating, built-in work-space, and breakfast nook. Family room is radiant with natural light that fills the space from the windows and French doors. Double sided, wood burning fireplace and built-in entertainment center help create the perfect entertainment space. Step outside and be inspired by the gorgeous backyard. Vinyl fencing around the property provides privacy, while the brick pavers, vine covered trellis, and stunning pool bring characteristic charm. Above the two-car, detached garage, is a guest apartment with office, half bath, and efficiency kitchen. Zoned for A-rated schools; Brookshire Elementary, Glendridge Middle, and Winter Park High. Schedule your showing today! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$825,000
$3,056/mo
Monthly Payment:
$3,056
Principal & Interest:
$3,056
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $165,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,180sq ft $259 / sq ft SFR
Lot Size12,460sq ft Built1925 On Site47days
Amazingly charming home on one of the most beautiful tree-lined streets in Winter Park. This 3100sf + pool home has a very open floor plan, lots of natural light, and upgrades... more
Amazingly charming home on one of the most beautiful tree-lined streets in Winter Park. This 3100sf + pool home has a very open floor plan, lots of natural light, and upgrades galore. Kitchen remodeled with granite counters, solid wood cabinets, stainless Bosch appliances, new gas range, & built-in Thermador refrigerator. Downstairs master suite with wood floors, walk-in closet, and master bath renovated with dual sinks, rain shower, & large garden tub. Additional 2nd downstairs bedroom. Upstairs has another spacious bedroom, full bath, and office that could be easily transformed into a private 4th bedroom. Features include plantation shutters, wood & Mexican tile floors, crown molding, built-in’s, French doors, and original lower level wine cellar. Recent updates include all new electrical, newer AC’s & water heater, bathroom renovations, new plantation shutters, Pella doors, custom-made fireplace mantle, hurricane resistant film on all windows, and new fans. This home sits on almost 1/3 acre lot and due to massive re-design & re-landscaping, the backyard is an oasis of privacy and seclusion including a lovely pool and outdoor covered kitchen cabana. 1 car garage + storage. Great, convenient location only a short walk to the lake! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$599,000
$2,222/mo
Monthly Payment:
$2,222
Principal & Interest:
$2,219
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.75% with $119,800 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,953sq ft $203 / sq ft SFR
Lot Size11,264sq ft Built1957 On Site47days
Renovated in 2009 to increase square footage to 2953 this three bedroom three bath home is located in the established neighborhood of Timberlane Shores. The property has a... more
Renovated in 2009 to increase square footage to 2953 this three bedroom three bath home is located in the established neighborhood of Timberlane Shores. The property has a wonderful flex space that could easily be converted into a fourth bedroom or a separate living space with it’s own entrance. It is currently being used as an art studio. The oversized master suite has coffered ceilings, two large walk in closets and acid etched concrete floors. The master bathroom has a separate shower and a 40 inch Soaking Tub. All three bedrooms have access to their own bathroom. There is also a small media room or office that is not considered a bedroom. Large hurricane rated glass doors and full length windows look out onto a herringbone brick patio with a tin roofed cabana to entertain your friends and family. The kitchen was enhanced with a professional style prep room and an additional refrigerator. The prep room has a pass-through to the cabana which can be converted to an out door kitchen. Renovation included: double paned windows throughout the house, new baseboards, new roof and the addition of a two garage. Owner is a licensed Realtor. less
Listing Provided Courtesy of Warner-quinlan Inc
Popularity
$799,900
$2,963/mo
Monthly Payment:
$2,963
Principal & Interest:
$2,963
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $159,980 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 3,064sq ft $261 / sq ft SFR
Lot Size8,775sq ft Built2008 On Site47days
Beautiful 5 bedroom Winter Park home in prime location with A+ Schools. Walk to Baldwin Park, Winter Park, close to airport. This home features wood floors, large kitchen with... more
Beautiful 5 bedroom Winter Park home in prime location with A+ Schools. Walk to Baldwin Park, Winter Park, close to airport. This home features wood floors, large kitchen with beautiful light cabinets and granite overlooking large fenced yard. First floor has 2 bedrooms, one currently being used as office. Upstairs 3 bedrooms and laundry. Yard has room for a pool. Call today to view this exquisite home! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
6 7 8 9 10 11 12 13 14 ... 19 29
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Local real estate services provided by:
Coldwell Banker Residential Real Estate
Coldwell Banker Residential Real Estate
5951 Cattleridge Ave
Sarasota, FL 34232

844.662.5638
Website provided and owned by Coldwell Banker Residential Real Estate.
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The information being provided by Mid-Florida Regional Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Mid-Florida Regional Multiple Listing Service. Coldwell Banker Residential Real Estate is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Coldwell Banker Residential Real Estate, a broker participant of Mid-Florida Regional Multiple Listing Service. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site.

The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Mid-Florida Regional Multiple Listing Service and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited.

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Data last updated: Tuesday, September 1, 2015 at 6:22 AM. Properties in listings may have been sold or may no longer be available.