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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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$594,000
$2,934/mo
Monthly Payment:
$2,934
Principal & Interest:
$2,200
HOA Dues:
$734
(Based on a 30 year fixed loan at 3.75% with $118,800 down)
Winter Park, FL 32789
3bed 3bath 1,706sq ft $348 / sq ft CND
Lot SizeN/Asq ft Built1971 On Site44days
Spacious 3 Bedroom 2.5 Bathroom. In original condition allowing you to upgrade to your personal taste. Lovely ground floor unit only steps to the waters edge, boat slips and... more
Spacious 3 Bedroom 2.5 Bathroom. In original condition allowing you to upgrade to your personal taste. Lovely ground floor unit only steps to the waters edge, boat slips and pool. High ceilings make this an ideal project to renovate. Condo fees include ground maintenance, insurance, 1 Block to Park Avenue shopping. Lake Osceola boat slips available for residents at a very nominal fee. Community pool for relaxation or exercise. Come home to this dream life every day! less
Listing Provided Courtesy of Florida One Real Estate Llc
Popularity
We show you every available listing. Here's how
$187,000
$692/mo
Monthly Payment:
$692
Principal & Interest:
$692
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $37,400 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
3bed 3bath 1,715sq ft $109 / sq ft SFR
Lot Size10,838sq ft Built1960 On Site44days
Three Bedroom, Two full and one half-bath, plus a small bonus room leading into the Master. The Master Suite is super large with an additional space that could be used for an... more
Three Bedroom, Two full and one half-bath, plus a small bonus room leading into the Master. The Master Suite is super large with an additional space that could be used for an office/den, craft area or a nursery. Home sits on a corner lot with a two car carport plus separate extended driveway with one parking pad. Additionally, there is a 35x12 attached, enclosed workshop, laundry room and a 45x14 breezeway adjacent to the carport that could be incredible flex space for the family or transformed into a mother-in-law suite, with a separate entrance and by easily recreating a former kitchen & bath. Home was replumbed in 1998, most recently new laminate flooring throughout except the two secondary bedrooms which are carpeted, newer refrigerator and glass top stove, butcher block counters in kitchen plus new sliders in the kitchen and master bedroom to the breezeway. There is also eat-in area in the kitchen, a covered porch to the entrance and fenced backyard. Located in the desirable Eastbrook community of Winter Park, this home is currently zoned for Eastbrook Elementary, Tuskawilla Middle & Lake Howell HS. If you are looking for a nice sized home with great potential, convenient to shopping, major highways, restaurants, employment, UCF, Valencia and Seminole State, you have arrived. American Home Shield one-year warranty up to $405 with acceptable offer. Sellers being transferred and motivated. Bring us an offer and let’s make it happen!!! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$1,350,000
$5,001/mo
Monthly Payment:
$5,001
Principal & Interest:
$5,001
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $270,000 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 5,169sq ft $261 / sq ft SFR
Lot Size14,677sq ft Built1991 On Site44days
Looking for european flair in winter park?...Then you have found it here...This contemporary-mediterranean home offers amazing european attributes and peerless quality inside... more
Looking for european flair in winter park?...Then you have found it here...This contemporary-mediterranean home offers amazing european attributes and peerless quality inside and out. This hidden gem neighborhood in the heart of winter park, gives residents quiet, tree-lined streets and walking or biking distance to the world-renowned park avenue, great schools and highways. The sellers have spared no expense updating this wonderful home to give it some flair from the ordinary, plus adding some energy-efficient features such as led lighting, double-paned windows - some with uv treatments - tankless water heater, pool solar heater, and water filtration system. The light and bright open concept family room/kitchen is perfect for any kind of gathering, with updated kitchen, quartz counters, upscale appliances and flooring, and amazing views to the backyard pool, deck and yard, which creates another living space. In addition, this home offers intimate rooms, like a formal living with its own fireplace, large dining room, plus two flex spaces, that could be his/her offices, craft room, fitness room or wine & cigar room. Plus, separate but connected, spacious true in-law/guest suite with it's own outside entrance, en suite bath & bedroom. Luxurious master suite is located upstairs, with plenty of room for seating, and the lovely master bath is spa-like. Additional kids or guest bedrooms are also upstairs. The home is amazing, with plenty of room for everyone...Must be seen in person to be truly appreciated! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$379,000
$1,890/mo
Monthly Payment:
$1,890
Principal & Interest:
$1,404
HOA Dues:
$486
(Based on a 30 year fixed loan at 3.75% with $75,800 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,143sq ft $332 / sq ft CND
Lot SizeN/Asq ft Built1971 On Site44days
Lovely 2 bedroom, 2 bath unit at the Cloisters. totally redone to very high standards. Truly move in condition. Walk to the pool. Less than 150 yards from the Alfond Hotel. 1... more
Lovely 2 bedroom, 2 bath unit at the Cloisters. totally redone to very high standards. Truly move in condition. Walk to the pool. Less than 150 yards from the Alfond Hotel. 1 block to the center of Park Avenue and the new Sun Rail station. Boat slips available for residents. Live life the way you always wanted to. Walk to Park Avenue daily, enjoy fine food or just a cup of coffee. Workout room, party room, pool and putting green, as well as covered parking. less
Listing Provided Courtesy of Florida One Real Estate Llc
Popularity
$109,900
$407/mo
Monthly Payment:
$407
Principal & Interest:
$407
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $21,980 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 987sq ft $111 / sq ft CND
Lot Size19.0acre Built1970 On Site44days
Welcome to the Four Seasons Condos. Lovingly cared for and well maintained, this spacious 2 bedroom/2bath condo is just the ticket. The open floor plan greets you with updated... more
Welcome to the Four Seasons Condos. Lovingly cared for and well maintained, this spacious 2 bedroom/2bath condo is just the ticket. The open floor plan greets you with updated laminate floors, new windows and plantation shutters. A neutral color palette completes the look. Brand new GE washer/dryer was just installed in the glass door enclosure off the kitchen. The large master bedroom suite features a spacious walk-in closet. There is plenty of storage space with the luxury of condo living. This particular unit comes with covered carport parking. Minutes away from downtown, Cady Way, WP Hospital, restaurants and shopping. Condo fees include water, sewer, lawn care, pest control, 3 gated pools, tennis court, gated laundry facilities and on-site management. It's easy breezy living in Winter Park. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$325,000
$1,235/mo
Monthly Payment:
$1,235
Principal & Interest:
$1,204
HOA Dues:
$31
(Based on a 30 year fixed loan at 3.75% with $65,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 3bath 2,340sq ft $139 / sq ft SFR
Lot Size10,810sq ft Built1985 On Site46days
This is a very nice Home in the desirable are of Pelican Bay with only 44 homes and deeded Lake access. This ranch home is a split plan with 4 bedrooms and 2 and a half baths... more
This is a very nice Home in the desirable are of Pelican Bay with only 44 homes and deeded Lake access. This ranch home is a split plan with 4 bedrooms and 2 and a half baths and a large family room with a fireplace and wet bar.There is a large Master Bedroom with a walk-in closet and a walk-in shower . An eat-in kithen with a seperate dining area, large screened outdoor patio area with a wet bar and Hot-tub for relaxing and entertaining. less
Listing Provided Courtesy of Charles Rutenberg Realty
Popularity
$299,900
$1,111/mo
Monthly Payment:
$1,111
Principal & Interest:
$1,111
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $59,980 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 2,527sq ft $119 / sq ft SFR
Lot Size6,766sq ft Built1940 On Site46days
Orwin manor opportunity! This wonderful 1940's "colonial" is loaded with opportunity and potential - bring your contractor. From the moment you walk in you'll notice the... more
Orwin manor opportunity! This wonderful 1940's "colonial" is loaded with opportunity and potential - bring your contractor. From the moment you walk in you'll notice the gorgeous (original) hardwood floors, the wood burning fireplace and plenty of space for the "grandest" of great rooms. There's a wonderful "sun room" which would be perfect for an office/family room. The kitchen is h-u-g-e and includes a sunny corner breakfast nook overlooking the back yard and deck. For the family chef there's natural gas available! Upstairs you'll find your imagination running wild with possibilities and a big plus is the third floor attic that is just waiting to be converted. It's already got sprayed on insulation and would be perfect to convert to a huge master suite. The back yard is large enough for a pool and the garage/studio could be used as a fabulous pool house for summer parties! For the "historic enthusiast" there's beautiful original crystal chandeliers, light fixtures and crystal doorknobs! If you want to move into orwin manor at a great price - this is your ticket. You can live in while doing your projects or remodel at your leisure and have a truly grand colonial to show for your efforts! less
Listing Provided Courtesy of Re/max Properties Sw Inc.
Popularity
$600,000
$2,225/mo
Monthly Payment:
$2,225
Principal & Interest:
$2,222
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.75% with $120,000 down)
Winter Park, FL 32789
Virginia Heights Orange County School District
4bed 2bath 1,750sq ft $343 / sq ft SFR
Lot Size11,806sq ft Built1925 On Site47days
Cute as a button and neat as a pin! This 1925 traditional home features 2 beds and a bath downstairs plus 2 bedrooms and a bath upstairs, the eat-in kitchen opens to a tranquil... more
Cute as a button and neat as a pin! This 1925 traditional home features 2 beds and a bath downstairs plus 2 bedrooms and a bath upstairs, the eat-in kitchen opens to a tranquil courtyard overlooking a converted carriage house/garage could be used for a mother-in-law apartment, teen suite, utility room or hobby room. There is a formal dining room and oversized family room which boasts a wood burning fireplace and built in aquarium. If your desire is to construct a new home, the double lot could accommodate a 5200 sq. ft. home with a double garage, or build a 2 story home and you could nearly double the living space. Don't miss your opportunity to own your Winter Park home within walking distance to Rollins College, Park Avenue, Winter Park 9th grade Center and so much more. Voluntary homeowner association fee of $30 annually gives you lake access at College Point! Carriage House (not included in square foot measurement) also has air conditioning, a full bath, and could be a great mother-in-law suite, college apartment or game room! less
Listing Provided Courtesy of Re/max 200 Realty
Popularity
$1,995,000
$7,558/mo
Monthly Payment:
$7,558
Principal & Interest:
$7,391
HOA Dues:
$167
(Based on a 30 year fixed loan at 3.75% with $399,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 5,395sq ft $370 / sq ft SFR
Lot Size18,931sq ft Built2004 On Site47days
Sophisticated executive home in prestigious vias. This stately 2 story residence with magnificent balconies is situated on a .44 acre lot in a secluded cul-de-sac with privacy... more
Sophisticated executive home in prestigious vias. This stately 2 story residence with magnificent balconies is situated on a .44 acre lot in a secluded cul-de-sac with privacy brick wall. Custom built in 2004 with impressive room sizes throughout! Gracious front porch and 27x8 foyer with hardwood floors & soaring ceilings invite you into the formal rooms & through to serene lanai, pool, hot tub & manicured backyard garden. Gourmet kitchen complete with butler's pantry, huge 16x6 walk in pantry, island + breakfast bar and cozy 12x11 breakfast nook. Family room with custom built-ins plus delightful game room with wet bar creates a perfect place to entertain. Amazing downstairs master suite boasts a renovated bath, his & her 20x6 closets, dressing area plus 13x8 office, massage room or nursery. Upstairs you will find 3 large en suite bedrooms plus additional flex room for home gym, upstairs family room or 5th bedroom, + 2 balconies for relaxation. Extras include: 3 car detached garage, plantation shutters, gas fireplaces in living room & game room, 3 new hvac units, generator & deeded lake access to the winter park chain of lakes!! Welcome home! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$540,000
$2,000/mo
Monthly Payment:
$2,000
Principal & Interest:
$2,000
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $108,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 3bath 2,244sq ft $241 / sq ft SFR
Lot Size23,543sq ft Built1987 On Site47days
Unbelievable!! This fabulous winter park home is located on (private) bear gully lake and has a great dock, boat house with electric boatlift, beach, green space and awesome... more
Unbelievable!! This fabulous winter park home is located on (private) bear gully lake and has a great dock, boat house with electric boatlift, beach, green space and awesome sunsets! Enjoy boating, jet-skiing, paddle boarding, water skiing or just observing nature. If you're looking for a "cookie-cutter" home, look elsewhere, this fabulous split bedroom floor plan is loaded with sensible storage, beautiful solid wood 6-panel doors, a floor-to-ceiling fireplace, great entertaining space, a screen enclosed inground pool with rock water feature, plenty of space around the pool for outdoor fun. The large kitchen has custom cabinetry and upgraded appliances. An indulgent master suite and formal dining room with plantation shutters. Beautiful floors enhance the home as well. Excellent seminole county schools and convenient to downtown winter park, winter springs, oviedo, university of central florida, full sail university, the beach, airport, cruise ports and area attractions via state road 417! Don't delay, schedule your private showing of this one-of-a-kind home today! less
Listing Provided Courtesy of Re/max 200 Realty
Popularity
$839,523
$3,110/mo
Monthly Payment:
$3,110
Principal & Interest:
$3,110
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $167,905 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,174sq ft $265 / sq ft SFR
Lot Size6,868sq ft Built2015 On Site47days
New Construction Meridian Homes 3 story charmer with lots of space and character with designer finishes throughout . This 4 bedroom 3.5 bath home has nearly 3200 sf and on... more
New Construction Meridian Homes 3 story charmer with lots of space and character with designer finishes throughout . This 4 bedroom 3.5 bath home has nearly 3200 sf and on cobblestone Winter Park street with beautiful trees and landscaping. Beautiful front porch leads you into foyer with creative wood working to add interest. Open kitchen family, great room layout and open to dining with formal living/office/den space. Covered porch for outdoor living and entertaining and spectacular kitchen with wet bar. Generous marble island in kitchen seats 6 with banquet style eat-in table with custom lighting package. The kitchen has great counter space all honed black granite on perimeter counters, light and bright custom cabinet design, Viking Stainless Appliances, gas stove top, counters, custom tile back splash and generous island. Kitchen is open to living room and dining room which overlooks covered porch to pool. Hardwood floors on first floor and painted wood stairs with custom carpets runners, carpet in secondary beds and tile in wet areas. Mudroom/drop zone and great closets to keep house organized. Inviting cobblestone entry and back covered porch bricked. Professionally landscaped to nestle this home in and make it a private retreat. This home has so much charm with 3rd floor bonus room with full bath and great space. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$169,900
$629/mo
Monthly Payment:
$629
Principal & Interest:
$629
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $33,980 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,535sq ft $111 / sq ft SFR
Lot Size9,020sq ft Built1981 On Site48days
This amazing 3 bedroom, 2 bath home is in move-in condition. Fresh painted interior walls and new installed carpet in all the bedrooms are just few of the new features of this... more
This amazing 3 bedroom, 2 bath home is in move-in condition. Fresh painted interior walls and new installed carpet in all the bedrooms are just few of the new features of this home. Other great features include extensive ceramic tile, fireplace in living room, family room off the kitchen, 2-car garage & 2 screened porches on a corner lot! This beautiful home has ceramic tile throughout the common areas with a fireplace in the living room; the kitchen is spacious and has lots of storage cabinets. You will also love screened porch on the front entrance for early morning coffee and reflection. Welcome Home! This is a Fannie Mae Homepath property! All information recorded in the MLS is intended to be accurate but cannot be guaranteed, buyer advised to verify. less
Listing Provided Courtesy of Keller Williams Advantage 2
Popularity
$759,000
$2,812/mo
Monthly Payment:
$2,812
Principal & Interest:
$2,812
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $151,800 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size15,107sq ft BuiltN/A On Site48days
Come build your Winter Park estate on this .35 acre oversized lot. Located on McKean Circle "point". Newer finished large pool makes a great starting point for your architect to... more
Come build your Winter Park estate on this .35 acre oversized lot. Located on McKean Circle "point". Newer finished large pool makes a great starting point for your architect to design around. Enjoy all the amenities of Winter Park with a 3 block stroll to Park Ave. Call today! NEW PRICE - SELLER WANTS AN OFFER!!!!! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$759,000
$2,812/mo
Monthly Payment:
$2,812
Principal & Interest:
$2,812
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $151,800 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,388sq ft $318 / sq ft SFR
Lot Size15,107sq ft Built1956 On Site48days
The most fabulous location in Winter Park! Re-model this spacious home with your own designer or tear down and start new on this oversized .35 acre site. Enjoy all the amenities... more
The most fabulous location in Winter Park! Re-model this spacious home with your own designer or tear down and start new on this oversized .35 acre site. Enjoy all the amenities of downtown Winter Park - a 3 block walk to Park Ave. Large pool is newly re-surfaced. Home has tremendous potential to expand with this end/corner location. NEW PRICE - SELLER WANTS AN OFFER!!!! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$375,900
$1,392/mo
Monthly Payment:
$1,392
Principal & Interest:
$1,392
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $75,180 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,239sq ft $168 / sq ft SFR
Lot Size11,358sq ft Built1973 On Site48days
Reduced....Owner motivated....This immaculate & completely updated four bedroom, three full bath, plus office single story home is situated on a quiet street in the sought after... more
Reduced....Owner motivated....This immaculate & completely updated four bedroom, three full bath, plus office single story home is situated on a quiet street in the sought after dommerich forest neighborhood. As you enter the drive you are greeted with a wonderful tree house that received a re-fresh in 2013. The attached childs' swing will offer hours of enjoyment. Inside the home there are vaulted ceilings in almost every room of the home. A total of three living areas makes it a snap for entertaining friends and family. The florida room with its large casement windows and 2 skylights offers views of the private backyard and covered/screened paver patio. The spacious kitchen has newer cabinets, a breakfast bar, 18x18 tile flooring and a built in desk with book shelves. There is fresh paint throughout and the ceilings were recently re-textured. In the back addition pella casement windows were also included as was built in bookshelves and a window seat. The master bedroom features volume ceilings and has the office/sitting room attached. The master bath includes a large jetted tub with mitered glass surround. Also featured is the travertine flooring and newer lighting and low flow commodes. The other three bedrooms have custom color walls, and there are two other updated bathrooms. This home is move in ready, come see it today!!!. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
8 9 10 11 12 13 14 15 16 ... 21 31
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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, July 28, 2015 at 12:07 PM. Properties in listings may have been sold or may no longer be available.