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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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$549,999
$2,037/mo
Monthly Payment:
$2,037
Principal & Interest:
$2,037
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $110,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,666sq ft $206 / sq ft SFR
Lot Size10,619sq ft Built1966 On Site74days
Immaculate and completely updated 4 bedroom 3 bath one story Winter Park home in quiet family neighborhood with A+ schools. Open kitchen dining and family room overlooking... more
Immaculate and completely updated 4 bedroom 3 bath one story Winter Park home in quiet family neighborhood with A+ schools. Open kitchen dining and family room overlooking beautiful salt pool and summer kitchen with brick paver patio. Large dining and living area are perfect for entertaining. Split bedroom plan, large master suite with closet organizers. Crown molding, travertine & hardwood floors throughout. Newer roof, gas appliances, inside laundry and more. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
Your search results are current and complete. Learn more
$132,900
$492/mo
Monthly Payment:
$492
Principal & Interest:
$492
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $26,580 down)
Winter Park, FL 32792
Seminole County School District
2bed 2bath 1,316sq ft $101 / sq ft CND
Lot Size2,035sq ft Built1984 On Site77days
Come see this charming 2BR/2BA townhome-style condo nestled away in the tranquil Winter Park community of Cedarwood Village. This home has been carefully maintained and ready... more
Come see this charming 2BR/2BA townhome-style condo nestled away in the tranquil Winter Park community of Cedarwood Village. This home has been carefully maintained and ready for a new owner to move right in. Some unique features of this home include kitchen upgrades with solid surface counter tops, stainless appliances, built-in wall oven, and decorative wood ceiling beams. Brick fireplace in the living room and cathedral ceiling with skylights brings in lots of natural light. Tropical garden at the front entrance leads to a cozy, private courtyard. Club house, pool, tennis court and dog run are among the community amenities available to residents. Being located near supermarkets, banks, restaurants and more, makes this condo a hidden gem! less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$548,500
$2,032/mo
Monthly Payment:
$2,032
Principal & Interest:
$2,032
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $109,700 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,632sq ft $336 / sq ft SFR
Lot Size7,436sq ft Built1958 On Site77days
This is an INCREDIBLE opportunity to live in the heart of downtown Winter Park. This 1950s, 3 bed, 2 bath home is just over 1600 square feet, and sits on a corner lot. It's... more
This is an INCREDIBLE opportunity to live in the heart of downtown Winter Park. This 1950s, 3 bed, 2 bath home is just over 1600 square feet, and sits on a corner lot. It's nestled among the tree lined, brick paved streets that Winter Park is known for, and surrounded by beautiful custom estates and historic homes. The sunny foyer leads you in to an open living area, and the upgraded kitchen features granite counter tops, beautiful wood cabinets, and high-end stainless steel appliances. The spacious master suite features a large glassed-in shower and a spa tub, perfect for relaxing after a long day. You can also enjoy out door dining in your private backyard oasis, with its pavered courtyard and lush landscaping. All appliances are included. Security system and closed circuit security cameras installed. Winter Park is an arts and culture filled city with a thriving downtown. You can walk to the Saturday morning Farmer's Market, or meet friends for a round of golf at the Winter Park Country Club, just around the corner. Properties like this don't come on the market often, so don't miss out! less
Listing Provided Courtesy of KELLER WILLIAMS ADVANTAGE 2
Popularity
$75,000
$277/mo
Monthly Payment:
$277
Principal & Interest:
$277
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $15,000 down)
Winter Park, FL 32792
Orange County School District
1bed 1bath 727sq ft $103 / sq ft CND
Lot Size19.0acre Built1970 On Site79days
Terrific 1/1 condo at Four Seasons-move in ready, refrigerator, dishwasher and range included. Look what the HOA covers; bldg. exterior maintenance, pool, escrow reserve funds,... more
Terrific 1/1 condo at Four Seasons-move in ready, refrigerator, dishwasher and range included. Look what the HOA covers; bldg. exterior maintenance, pool, escrow reserve funds, ground maintenance, bldg insurance, manager, pest control, private road, recreation facility, roof, tennis courts, trash removal, water/sewer-$310 per months. Come enjoy and relax! Two swimming pools, courts, covered parking space (plus guest parking). complex is walking distance to supermarkets, restaurants, bowling, hospital, fitness centers, banks, and the Cady Way bike paths. less
Listing Provided Courtesy of LA ROSA REALTY, LLC
Popularity
$98,000
$525/mo
Monthly Payment:
$525
Principal & Interest:
$363
HOA Dues:
$162
(Based on a 30 year fixed loan at 3.75% with $19,600 down)
Winter Park, FL 32789
Orange County School District
1bed 1bath 645sq ft $152 / sq ft CND
Lot Size2,107sq ft Built1969 On Site80days
Gorgeous, newly remodeled 1br/1bath condo with totally New Kitchen cabinets, New Sink & Granite counter tops. Stainless Steel Appliance package. New Roof. Newly Remodeled... more
Gorgeous, newly remodeled 1br/1bath condo with totally New Kitchen cabinets, New Sink & Granite counter tops. Stainless Steel Appliance package. New Roof. Newly Remodeled Bathrooms with travertine floor and glass door shower. New Laminate Flooring throughout. New Windows, new LED lights throughout and Freshly painted inside. This beautiful complex offers private access to Lake Killarney, boat docking, a swimming pool and a clubhouse. The condo is located 2.6 miles from Park Avnenue in the historic district of Winter Park and 2.7 miles from Rollins College. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$379,000
$1,404/mo
Monthly Payment:
$1,404
Principal & Interest:
$1,404
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $75,800 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,750sq ft $217 / sq ft SFR
Lot Size3,500sq ft Built2015 On Site80days
New construction !!! 2015 single family semi attached home in heart of winter park. This home features 3 bedrooms and 3 bathrooms !! With approximately 1750 sq ft this would... more
New construction !!! 2015 single family semi attached home in heart of winter park. This home features 3 bedrooms and 3 bathrooms !! With approximately 1750 sq ft this would make it an ideal starter home or a great rental property. Close to shopping, transportation with winter park schools !!! This property wont last, come by and see it today. Will be finished march 30th approximately less
Listing Provided Courtesy of CHARLES RUTENBERG REALTY
Popularity
$474,900
$1,759/mo
Monthly Payment:
$1,759
Principal & Interest:
$1,759
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $94,980 down)
Winter Park, FL 32792
Golfside Orange County School District
4bed 3bath 2,596sq ft $183 / sq ft SFR
Lot Size10,773sq ft Built1968 On Site80days
Spectacular Winter Park Pool Home! This 4 bedroom, 2.5 bath home with 2 car garage has been completely updated! Welcome Home! Enter this stunning home into a large foyer with a... more
Spectacular Winter Park Pool Home! This 4 bedroom, 2.5 bath home with 2 car garage has been completely updated! Welcome Home! Enter this stunning home into a large foyer with a quiet library off the foyer. This amazing home delights you with an open floor plan and a gourmet kitchen that the pickiest of chefs will enjoy. Spacious family room with French sliding doors overlooking the sparkling pool. Separate formal dining is great for intimate dinners. Features include: Brick Pavers *Resurfaced pool in 2000 *Fully Renovated * Roof * Flooring * A/C Duct Work and A/C * Gas lines installed by TECO *Tankless water heater *salt water pool system * Solar heated pool *Replumbed Kitchen and baths* Outdoor shower and so much more! Expect to be impressed by this beautiful home! less
Listing Provided Courtesy of PRESTIGE PROPERTY SHOP LLC
Popularity
$225,900
$836/mo
Monthly Payment:
$836
Principal & Interest:
$836
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $45,180 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
3bed 2bath 1,487sq ft $152 / sq ft SFR
Lot Size17,317sq ft Built1951 On Site80days
This Winter Park charmer is ready for a new owner. Located on a quiet boulevard this 3 bedroom 2 bath home is just steps away from lovely Lake Killarney. This home has been well... more
This Winter Park charmer is ready for a new owner. Located on a quiet boulevard this 3 bedroom 2 bath home is just steps away from lovely Lake Killarney. This home has been well maintained and features a large lot and a storage shed in the back yard. The cozy interior will make you feel like you are right at home. This great location is minutes away from world class Winter Park shopping & dining. You could not ask for a better location in Central Florida. Please make an appointment today to view this wonderful property. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$390,000
$1,444/mo
Monthly Payment:
$1,444
Principal & Interest:
$1,444
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $78,000 down)
Winter Park, FL 32792
Orange County School District
4bed 3bath 2,293sq ft $170 / sq ft SFR
Lot Size10,790sq ft Built1966 On Site81days
New price!!! Time to call kenilworth shores home with the cady way trail access on the same block! Walk into the large foyer with the original polished marble floor where you'll... more
New price!!! Time to call kenilworth shores home with the cady way trail access on the same block! Walk into the large foyer with the original polished marble floor where you'll find hominess all around. This home offers a great split floor-plan along with a formal dining room and living/media room. Updated kitchen combined with the family room offers cozy fireside chats that abuts the florida room . Custom built in shelves adorn the brick wood burning fireplace. Pool views abound from the florida room complete with wetbar. Outside you'll find the newly patio-paver pool that's been recently re-surfaced and updated (2015). Mega sized backyard with a walkway leads you to an exterior patio/grill area. There's an outside shower that awaits your au-natural rinse. Large formal living room can be transformed into a media and/or game room. Master br on one side and 3 br w/1.5 bath on the other. Roof/ac/plumbing/electrical - all done in last 10 years. Convenient to east end market, park ave., rollins college and baldwin park . Spaciousness with lots of living space in this most convenient winter park family home. Walk to winter park high with brookshire elem. And glenridge middle being the other schools. New price - motivated seller . less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$247,500
$952/mo
Monthly Payment:
$952
Principal & Interest:
$916
HOA Dues:
$36
(Based on a 30 year fixed loan at 3.75% with $49,500 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,919sq ft $129 / sq ft SFR
Lot Size6,035sq ft Built1990 On Site84days
Just reduced! Nice home in a peaceful neighborhood! Upgraded 3 bedroom 2 bath plus a bonus room that can be used as a den or office. This home features an over-sized back... more
Just reduced! Nice home in a peaceful neighborhood! Upgraded 3 bedroom 2 bath plus a bonus room that can be used as a den or office. This home features an over-sized back screened in lanai, fenced-in low maintenance yard with irrigation system, kitchen remodeled with solid wood cabinets, granite counter tops. Ceramic floors throughout home with carpet in the bedrooms. Seller offers 2500.00 decor allowance for full price offer. close to shopping and major roads. Neighborhood includes a park and tennis courts. less
Listing Provided Courtesy of RENCHER REALTY GROUP
Popularity
$699,000
$2,589/mo
Monthly Payment:
$2,589
Principal & Interest:
$2,589
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $139,800 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 2,393sq ft $292 / sq ft SFR
Lot Size7,494sq ft Built2004 On Site85days
Pristine. Sophisticated. Turn key! Beautiful new front double doors welcome you to this immaculate home complete with lovely finishes. Gleaming hardwood floors, high ceilings &... more
Pristine. Sophisticated. Turn key! Beautiful new front double doors welcome you to this immaculate home complete with lovely finishes. Gleaming hardwood floors, high ceilings & crown molding throughout, this gem boasts formal living & dining rooms, a cheerful kitchen with granite countertops overlooking family room with woodburning fireplace & built-ins. The master bath includes a custom shower, his & her walk-in closets & dual vanity. Delightful back patio & quaint backyard garden is the perfect spot to enjoy your morning coffee. Extras include: inside utility room, custom blinds, freshly painted exterior, new exterior doors, 2 car detached garage & fantastic winter park location! Walk to restaurants, shopping, park & ymca. This home has been meticulously maintained by the original owners & pride of ownership will amaze you! Welcome home! less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$229,000
$849/mo
Monthly Payment:
$849
Principal & Interest:
$848
HOA Dues:
$1
(Based on a 30 year fixed loan at 3.75% with $45,800 down)
Winter Park, FL 32792
Seminole County School District
4bed 2bath 1,780sq ft $129 / sq ft SFR
Lot Size8,400sq ft Built1969 On Site86days
Open Fri Feb 12, 2pm-5pm
If you are looking for something chic, yet cozy look no further! This is not your parents' ranch-style, for this dwelling has been elegantly renovated from attic to cellar with... more
If you are looking for something chic, yet cozy look no further! This is not your parents' ranch-style, for this dwelling has been elegantly renovated from attic to cellar with contemporary features. Waltzing in from the front door, you first come across a recessed living room which shows off wall to wall ceramic tiles, and ivory plantation shutters for that warm Florida feeling. A short step up is the elevated kitchen, were one can appreciate the true renovation. Wood cabinets and gray granite counter tops neatly bring the space together, as laminate wood floor, contemporary lighting, and a glass cook top add to the appeal. The breakfast bar allows sunlight to bounce from room to room. The master bedroom is traditional in sense, yet the bathroom is a must see. Dark stone counter tops with his and her sinks and corresponding vanity mirrors makes sure there is no rubbing of elbows. Wall to wall stone work make this bathroom bright. The subordinate bathroom also features masterful tile work, that rivals the master bathroom. Making our way to the back, we enter an air controlled, tiled floored Florida room with french doors, and where the large windowed walls give way to a luscious backyard space. The patio is complete with an in-ground pool, and enclosed by fencing on all sides to provide privacy. The house has been fitted with an upgraded roof, up dated plumbing, and brand new garage door opener. A new roof and brand new plumbing guarantee peace of mind. A bonus room can be converted to make a 4th bedroom less
Listing Provided Courtesy of KELLER WILLIAMS ADVANTAGE 2
Popularity
$98,000
$401/mo
Monthly Payment:
$401
Principal & Interest:
$363
HOA Dues:
$38
(Based on a 30 year fixed loan at 3.75% with $19,600 down)
Winter Park, FL 32792
Seminole County School District
2bed 2bath 1,338sq ft $73 / sq ft TWN
Lot Size3,810sq ft Built1981 On Site86days
Short sale - approved short sale price. Listing price may not be sufficient to pay the total of all encumbrances, closing costs, or other seller charges and sale of property at... more
Short sale - approved short sale price. Listing price may not be sufficient to pay the total of all encumbrances, closing costs, or other seller charges and sale of property at full listing price may require approval of seller's lender(s)/3rd party approval. Looking for a great deal in winter park? Take a look at this 2/2 with over 1300 sq ft of living space. Open floor-plan offering living room, dining room, two bedrooms, a full office/den and screened in patio with fenced in yard. Located within 15 minutes of downtown orlando. Corner end unit with driveway that will accommodate two cars. This property is a short sale and the seller has an attorney negotiating the sale. Hoa is current and only $ 113.00 quarterly. less
Listing Provided Courtesy of BHHS RESULTS REALTY
Popularity
$2,100,000
$7,780/mo
Monthly Payment:
$7,780
Principal & Interest:
$7,780
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $420,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 3,276sq ft $641 / sq ft CND
Lot Size27,512sq ft Built2008 On Site87days
A block from Winter Park's famed Park Ave., The Residences at Villa Siena combines the convenience of city living with the privilege of estate luxury, packaged in a classic... more
A block from Winter Park's famed Park Ave., The Residences at Villa Siena combines the convenience of city living with the privilege of estate luxury, packaged in a classic architecture facade reminiscent of old Tuscany. Villa two features an open floor plan, 3 bedrooms, 3 full and one-half baths, and 3276 HTD SF of 100% luxury. Through French doors upon Travertine floors into the grand entry foyer, you will notice trayed ceilings and extensive moldings. Adjacent the formal dining room, the gourmet kitchen has wood cabinets, stunning granite countertops, and top-of-the-line Wolf/Sub-Zero appliances. Flooded with natural light, the condos central living space opens to an extended balcony via three French doors overlooking New England Ave. A Jr. Master Suite offering access to the outdoor patio, and a bathroom with soaking tub, separate shower, and dual sinks. The office, lined with floor-to-ceiling wood bookcases and a wall of refrigerated wine storage for 750 bottles. Suite two features a full bath, patio access, and ample room for a king-sized bed. At the end of the hall, the liberal master wing has patio access, walk-in closets, and a bath w/jetted tub and walk-in shower. With only four floors, Villa Siena provides unparalleled privacy in an amenity-rich, intimate setting. The building includes a residents club room w/bar, billiards & card lounge, fitness center, and rooftop terrace. Located in the heart of Winter Park, walking distance to world class shopping & dining, Rollins College & the Alford Inn. less
Listing Provided Courtesy of STOCKWORTH REALTY GROUP
Popularity
$214,500
$794/mo
Monthly Payment:
$794
Principal & Interest:
$794
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $42,900 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
4bed 2bath 1,593sq ft $135 / sq ft SFR
Lot Size6,535sq ft Built1951 On Site87days
Gorgeous remodeled 4 bedroom/2 bathroom split plan house. This house has it all! Totally new Kitchen cabinets with New Sink & Granite counter tops. Stainless Steel Appliance... more
Gorgeous remodeled 4 bedroom/2 bathroom split plan house. This house has it all! Totally new Kitchen cabinets with New Sink & Granite counter tops. Stainless Steel Appliance package. New Roof in 2007, New Remodeled Bathrooms. New Flooring throughout. Freshly painted inside and out and much more. Beautiful back porch and shady backyard. Great curb appeal. Buyer or their agent to verify room sizes. less
Listing Provided Courtesy of PARK VIEW REALTY INC
Popularity
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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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Data last updated: Thursday, February 11, 2016 at 2:29 PM. Properties in listings may have been sold or may no longer be available.