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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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$84,000
$383/mo
Monthly Payment:
$383
Principal & Interest:
$311
HOA Dues:
$72
(Based on a 30 year fixed loan at 3.75% with $16,800 down)
Winter Park, FL 32792
Seminole County School District
2bed 2bath 1,020sq ft $82 / sq ft CND
Lot Size3,553sq ft Built1977 On Site8days
East Winter Park Condo located in the Windward Square community. Located just off 436 and convenient to employment, shopping and restaurants. Low HOA fees. This one story... more
East Winter Park Condo located in the Windward Square community. Located just off 436 and convenient to employment, shopping and restaurants. Low HOA fees. This one story townhome is just steps from the neighborhood swimming pools as well as two kiddie pools, tennis courts and a shuffle board gaming area. This home boasts, custom tile floors, soaring ceilings beautifully accented with exposed cedar, renovated bathroom with newer vanity, large bedrooms, galley kitchen with passthrough to the dining room. Additionally, there is a fully enclosed Florida Room that is fully tiled and has air conditioning. The private fenced backyard is great area for family and friend to gather and/or pets. You will love this charming home! Property was built prior to 1978 and lead based paint potentially exists. Property is sold as is. less
Listing Provided Courtesy of 1 Able Realty Llc
Popularity
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$399,000
$1,478/mo
Monthly Payment:
$1,478
Principal & Interest:
$1,478
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $79,800 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,341sq ft $298 / sq ft SFR
Lot Size9,732sq ft Built1948 On Site8days
Desirable corner lot in Winter Park! This 75x125’ lot (0.22 acres) is located on a quiet, tree-lined brick street. Tucked away in one of Winter Park’s most sought... more
Desirable corner lot in Winter Park! This 75x125’ lot (0.22 acres) is located on a quiet, tree-lined brick street. Tucked away in one of Winter Park’s most sought after neighborhoods, this home is surrounded by million dollar estates, new construction, and gorgeous remodels. Just a short bike ride to Park Avenue, Baldwin Park, and the trendy Audubon Park district. Fantastic schools! Audubon Elementary, Glenridge Middle School, and Winter Park High School. Build your dream home. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$399,000
$1,478/mo
Monthly Payment:
$1,478
Principal & Interest:
$1,478
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $79,800 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size9,731sq ft BuiltN/A On Site8days
Desirable corner lot in Winter Park! This 75x125’ lot (0.22 acres) is located on a quiet, tree-lined brick street. Tucked away in one of Winter Park’s most sought... more
Desirable corner lot in Winter Park! This 75x125’ lot (0.22 acres) is located on a quiet, tree-lined brick street. Tucked away in one of Winter Park’s most sought after neighborhoods, this home is surrounded by million dollar estates, new construction, and gorgeous remodels. Just a short bike ride to Park Avenue, Baldwin Park, and the trendy Audubon Park district. Fantastic schools! Audubon Elementary, Glenridge Middle School, and Winter Park High School. Build your dream home today! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$795,000
$2,985/mo
Monthly Payment:
$2,985
Principal & Interest:
$2,945
HOA Dues:
$40
(Based on a 30 year fixed loan at 3.75% with $159,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,097sq ft $257 / sq ft SFR
Lot Size18,888sq ft Built1972 On Site9days
This home says “quality”. Complete re-model of this lovely one story, 4 bedroom home with a separate office, has high quality finishes and amazing architectural... more
This home says “quality”. Complete re-model of this lovely one story, 4 bedroom home with a separate office, has high quality finishes and amazing architectural details - is all done for you to move right in… it’s perfect. Brazilian cherry, real wood floors, beautiful moldings and trim abound. Very open family room to kitchen and breakfast room that is flooded with natural light. French doors, library built-ins and wood burning fireplace make the family space a delight. Just imagine pool parties with your friends and family around this huge screened pool and lanai area. Pebble finish lagoon style pool has a separate spa and diving board! All bedrooms are spacious and have great views and lots of light. Private feeling yet friendly neighborhood and cul-de-sac location, great schools and easy access to downtown Winter Park, Rollins College, Florida Hospitals, Baldwin Park and Orlando. less
Listing Provided Courtesy of Parkland International Realty
Popularity
$49,900
$463/mo
Monthly Payment:
$463
Principal & Interest:
$184
HOA Dues:
$279
(Based on a 30 year fixed loan at 3.75% with $9,980 down)
Winter Park, FL 32789
Orange County School District
1bed 1bath 638sq ft $78 / sq ft CND
Lot Size638sq ft Built1966 On Site9days
Great location!!! 1st floor condo in centrally-located community that has a pool, playground and secure, coded building entry! This one bedroom, one bathroom condo has ceramic... more
Great location!!! 1st floor condo in centrally-located community that has a pool, playground and secure, coded building entry! This one bedroom, one bathroom condo has ceramic tile, carpet, contemporary lighting, brushed nickel fixtures and ceiling fans throughout. Living room has sliding glass doors that open up to a screened patio. The kitchen features a closet pantry, and a refrigerator, oven, dishwasher and microwave that all stay! Master bedroom has a walk-in closet with plenty of space for storage. Utility closet with washer and dryer that stay! This community has a pool and a playground, bbq/picnic area. Walking distance to winter park village, restaurants, shopping, entertainment and convenient to i-4 and 17-92! This is a homepath property. less
Listing Provided Courtesy of Re/max 200 Realty
Popularity
$340,000
$1,292/mo
Monthly Payment:
$1,292
Principal & Interest:
$1,259
HOA Dues:
$33
(Based on a 30 year fixed loan at 3.75% with $68,000 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,941sq ft $175 / sq ft TWN
Lot Size6,269sq ft Built1980 On Site9days
Welcome to Waterbridge. This corner lot home with private serene garden is a must see. The home is a one story; 2 bedroom 2 bath spacious 1,941 sqft. home with loft, wood... more
Welcome to Waterbridge. This corner lot home with private serene garden is a must see. The home is a one story; 2 bedroom 2 bath spacious 1,941 sqft. home with loft, wood burning fireplace, vaulted ceilings and a beautiful sun room. Waterbridge is perfectly situated near downtown Winter Park, minutes from healthcare, shopping, schools and recreation. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$234,000
$866/mo
Monthly Payment:
$866
Principal & Interest:
$866
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $46,800 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
4bed 2bath 1,461sq ft $160 / sq ft SFR
Lot Size13,321sq ft Built1951 On Site9days
Welcome Home! This Home has Everything you would want and the Location is priceless! Located less than 1 minutes walk to Beautiful Lake Killarney, 2 minutes from I-4 , and just... more
Welcome Home! This Home has Everything you would want and the Location is priceless! Located less than 1 minutes walk to Beautiful Lake Killarney, 2 minutes from I-4 , and just minutes from the wonderful shopping area of Winter Park Village and Park Avenue! This adorable 4 bedroom 2 bath home has a highly desirable split floor plan - perfect for families AND boasts of a Large and Beautiful back yard with a swing set, sand pit and lots of space for running around and gatherings for family and friends! The back yard is Large enough for a pool lots of open space left over. There is also a long drive way with parking pad and a stand along aluminum building for storage. This home will not last long. Make an appointment today. less
Listing Provided Courtesy of Keller Williams Winter Park
Popularity
$1,095,000
$4,277/mo
Monthly Payment:
$4,277
Principal & Interest:
$4,056
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $219,000 down)
Winter Park, FL 32789
Windsong Orange County School District
5bed 3bath 3,598sq ft $304 / sq ft SFR
Lot Size15,004sq ft Built2005 On Site12days
Beautiful one story Mediterranean home on the market for the very first time in prestigious Windsong. Custom built by Signature Homes, this wonderful home features formal living... more
Beautiful one story Mediterranean home on the market for the very first time in prestigious Windsong. Custom built by Signature Homes, this wonderful home features formal living and dining rooms, a three-way split floor plan plus a spacious bonus room that would make a great 5th bedroom, playroom or private home office. Highlights include travertine floors throughout, a gourmet kitchen with custom cabinets, a six burner gas range and double ovens that overlook the family room with a beautiful gas fireplace. The master suite is generously sized, overlooking the backyard with his and hers walk in closets and a jacuzzi tub. Windsong residents enjoy access to the Winter Park chain of lakes, two community pools and a children's splash park located walking distance from this home. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$427,500
$1,683/mo
Monthly Payment:
$1,683
Principal & Interest:
$1,583
HOA Dues:
$100
(Based on a 30 year fixed loan at 3.75% with $85,500 down)
Winter Park, FL 32792
4bed 4bath 2,842sq ft $150 / sq ft SFR
Lot Size10,899sq ft Built2015 On Site12days
Highly sought after winter park address! This brand new home is barely lived in and is ready to move-in! Only one lot left in sanctuary at aloma so why not purchase a brand new... more
Highly sought after winter park address! This brand new home is barely lived in and is ready to move-in! Only one lot left in sanctuary at aloma so why not purchase a brand new home which includes a warranty instead of waiting? This inverness “a” floor plan is loaded with upgrades. This one level home welcomes you with hardwood floors throughout, a spacious kitchen overlooking the family room that leads out to a spacious screened in patio. The kitchen features granite countertops, top of the line stainless steel appliances, upgraded cabinets with under-mount & interior lighting. The office can be used as a den or game room. The large master bathroom leads into a spacious bathroom featuring rainfall & dual shower heads & built in bench for convenience & dual sinks & vanities. The master also features a spacious walk-in closet. The many features in this inverness plan are 4 bedrooms, a family room, living room/study, breakfast nook & split plan with two bedrooms on opposite end of home than master. This is a great family home & offers a large yard! You have plenty of room for parking in the 2 car garage and parking pad. It’s conveniently located to 417 and downtown orlando historical area. The community is also securely gated with push button access. Easy to show and ready for a buyer! less
Listing Provided Courtesy of Better Homes & Gardens Fine Living
Popularity
$255,000
$944/mo
Monthly Payment:
$944
Principal & Interest:
$944
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $51,000 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
3bed 2bath 1,173sq ft $217 / sq ft SFR
Lot Size10,500sq ft Built1973 On Site12days
Location, location, location! 3 bedrooms, 2 bathroom, huge pool for entertainment. Completely remodeled, move in ready. No hoa; this home is in an "a" rated school district.... more
Location, location, location! 3 bedrooms, 2 bathroom, huge pool for entertainment. Completely remodeled, move in ready. No hoa; this home is in an "a" rated school district. Must see! less
Listing Provided Courtesy of Commercial Homes & Land Inc
Popularity
$259,900
$963/mo
Monthly Payment:
$963
Principal & Interest:
$962
HOA Dues:
$1
(Based on a 30 year fixed loan at 3.75% with $51,980 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,312sq ft $198 / sq ft SFR
Lot Size8,400sq ft Built1969 On Site12days
Freshly remodeled with new appliances and new roof, new plumbing to all fixtures and repiped. Seminole county schools. 3 bedroom, 2 bathroom pool home. Large living room, open... more
Freshly remodeled with new appliances and new roof, new plumbing to all fixtures and repiped. Seminole county schools. 3 bedroom, 2 bathroom pool home. Large living room, open and airy kitchen with breakfast bar opens to the dining area. Florida room opens to the in-ground pool and fenced in yard. Bonus room can be used as an office, den or another bedroom. less
Listing Provided Courtesy of Addvantage Real Estate Services
Popularity
$458,900
$1,700/mo
Monthly Payment:
$1,700
Principal & Interest:
$1,700
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $91,780 down)
Winter Park, FL 32789
Virginia Heights Orange County School District
3bed 3bath 2,303sq ft $199 / sq ft SFR
Lot Size7,500sq ft Built1990 On Site12days
Gorgeous two story, 3 bedroom home Winter Park. Nice kitchen overlooks family room, fireplace in living room, privacy of fenced backyard, screened lanai, custom tile, and many... more
Gorgeous two story, 3 bedroom home Winter Park. Nice kitchen overlooks family room, fireplace in living room, privacy of fenced backyard, screened lanai, custom tile, and many more upgrades throughout. Located just minutes from Park Avenue's shopping, restaurants, and Farmer's Market. A must see!! See Notice and Acknowledgement of Reo Purchaser Screening form prior to writing an offer. Seller requires that potential buyers execute the disclosure and submit with their offer in order to be considered. Document located in Listings Docs on TAZA Homes the link is located in Realtor Remarks. Property must be listed for 5 days before offers may be negotiated/accepted. All information recorded in the MLS is intended to be accurate but cannot be guaranteed, buyers advised to verify. less
Listing Provided Courtesy of Mickey Hage Inc
Popularity
$979,999
$3,630/mo
Monthly Payment:
$3,630
Principal & Interest:
$3,630
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $196,000 down)
Winter Park, FL 32792
Orange County School District
6bed 6bath 5,005sq ft $196 / sq ft SFR
Lot Size14,630sq ft Built1962 On Site12days
Don't miss this opportunity to purchase this Luxury Brick Estate home in the City of Winter Park. Gourmet chef's dream kitchen with stone fireplace and top-of-the-line... more
Don't miss this opportunity to purchase this Luxury Brick Estate home in the City of Winter Park. Gourmet chef's dream kitchen with stone fireplace and top-of-the-line commercial grade Appliances, custom wood cabinets and seamless exotic Italian Granite. The kitchen also offers a center island with 2 Austrian Crystal chandeliers. French doors,wood floors, crown molding and jetted tubs and a dedicated home theater. Separate 1500 square-foot guesthouse with kitchen, huge bedroom, bathroom and great room. Guesthouse has double French doors opening to a private Tuscan courtyard. This estate is an entertainers dream home with separate outdoor pavilion with fans and mature landscaping. Home is surrounded by private wall with 35 carriage lights to light up this beautiful oasis. Gated back and side yards lead to an elaborate pool with travertine tile pool deck and wrought iron child safety gates and a custom Koi pond with bridge and waterfall and access to Cady Way Trail.This home is minutes to Park Avenue, WP Farmers Market, luxury shopping and fine dining, Sunrail/Amtrak station, Rollins College, golf courses and the Interlachen Country Club as well as many parks and recreation facilities. Don't miss this rare opportunity to own a great home in the City of Winter Park Additional home features include in wall and ceiling surround sound system, solid bronze door knobs on all interior doors, new roof in 2013, new 3 1/2 ton air conditioning unit in 2015 and a 4 ton air-conditioning unit in 2010. less
Listing Provided Courtesy of Florida Realty Team Of Central
Popularity
$245,000
$907/mo
Monthly Payment:
$907
Principal & Interest:
$907
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $49,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,453sq ft $169 / sq ft SFR
Lot Size7,000sq ft Built1949 On Site13days
A cute 3 bedrooms 2 baths split floor plan in a great area of Winter Park minutes from Park Ave and I-4. Hardwood floor in bedrooms and new concrete look in living room. The... more
A cute 3 bedrooms 2 baths split floor plan in a great area of Winter Park minutes from Park Ave and I-4. Hardwood floor in bedrooms and new concrete look in living room. The house was renovated recently but can use additional TLC. A huge back yard zoned for a Duplex in winter park (R-2). Very desirable area of Winter Park for new construction and a hot rental market. Great investment opportunity. less
Listing Provided Courtesy of Pinecrest Real Estate Mngt
Popularity
$354,000
$1,311/mo
Monthly Payment:
$1,311
Principal & Interest:
$1,311
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $70,800 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,436sq ft $247 / sq ft SFR
Lot Size9,773sq ft Built1956 On Site13days
Perfect Location in Winter Park, and Great Schools. The Lot is 70 x 130. 3 Bed/ 2 Bath home on a quiet street. Call with any questions. More photos to follow once the tenants... more
Perfect Location in Winter Park, and Great Schools. The Lot is 70 x 130. 3 Bed/ 2 Bath home on a quiet street. Call with any questions. More photos to follow once the tenants move on 8/31. less
Listing Provided Courtesy of Uown Real Estate
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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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.