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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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$119,000
$440/mo
Monthly Payment:
$440
Principal & Interest:
$440
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $23,800 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size7,000sq ft BuiltN/A On Site21days
Very nice buildable lot in desirable Winter Park neighborhood of Dubsdread Heights - conveniently located between College Park and Winter Park with easy access to I-4, the... more
Very nice buildable lot in desirable Winter Park neighborhood of Dubsdread Heights - conveniently located between College Park and Winter Park with easy access to I-4, the Maitland Interchange and shops and restaurants. Lot size is 50 x 140 with several shade trees. Existing home on-site is a teardown or could be renovated for personal home or as a rental property. There is also an opportunity to buy 754 Baffie (next door) MLS #O5378518 and have two buildable lots. less
Listing Provided Courtesy of Anne Rogers Realty Group Inc
Popularity
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$674,900
$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 $134,980 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 3,332sq ft $203 / sq ft SFR
Lot Size7,875sq ft Built1950 On Site22days
Beautiful 3 bedroom 4 bath home in Olde Winter Park. This home was significantly remodeled in 2009 with wood floors, crown molding, gourmet kitchen with granite counters,... more
Beautiful 3 bedroom 4 bath home in Olde Winter Park. This home was significantly remodeled in 2009 with wood floors, crown molding, gourmet kitchen with granite counters, beautiful cabinets & travertine. The home was significantly enlarged, adding a second floor with bonus room along with two bedrooms and baths upstairs. Master down with a spacious master bath. Large fenced backyard with a gorgeous pool. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$1,579,000
$6,071/mo
Monthly Payment:
$6,071
Principal & Interest:
$5,850
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $315,800 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 4,606sq ft $343 / sq ft SFR
Lot Size16,253sq ft Built2004 On Site23days
Spectacular four bedroom, four and one-half bath pool home in prestigious Windsong. Original Charleston Carolina lanterns, Brazilian cherry floors, solid mahogany French doors,... more
Spectacular four bedroom, four and one-half bath pool home in prestigious Windsong. Original Charleston Carolina lanterns, Brazilian cherry floors, solid mahogany French doors, custom wrought iron railings, and soaring ceilings; this home is absolutely stunning! Formal living and dining rooms, an open family room, and a guest suite with full bath provide a comfortable yet very functional first floor. Gorgeous gourmet kitchen, complete with a custom farmhouse sink, gas stove, nickel-finish pendants, and white Carrera marble countertops has eat-in dining and views of the covered lanai and pool. Master bedroom features a private bath with marble shower and vanities, a large soaking tub, and an expansive walk-in closet. Additionally, two generously sized bedrooms and a bonus room over the garage can be found upstairs. Outdoors, enjoy quiet evenings or entertaining guests on the covered lanai with bead-board ceilings, or take a dip in the Hampton’s style pool. Located in one of Winter Park’s most desirable communities, Windsong offers its residents amenities like no other: chain of lake access, private boat rental, fishing pier, parks, two recreational pools, and a children’s water park. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$995,000
$3,686/mo
Monthly Payment:
$3,686
Principal & Interest:
$3,686
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $199,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,853sq ft $258 / sq ft SFR
Lot Size14,312sq ft Built1969 On Site23days
This fabulous four bedroom single story pool home is situated on a large meticulously manicured lot in the highly desirable community of Park North just a few blocks from Park... more
This fabulous four bedroom single story pool home is situated on a large meticulously manicured lot in the highly desirable community of Park North just a few blocks from Park Avenue’s boutiques, restaurants, Central Park, The Farmers’ Market, the Winter Park Golf Course, Hannibal Square & all the charm Winter Park offers. This immaculate home is light, bright & move in ready. Updated kitchen has a natural gas cooktop, stainless steel appliances & granite countertops. Kitchen overlooks the family room w/ cozy fireplace & the Florida room w/ wet bar & glass doors which open to the pool & private walled in yard. Formal living & dining combo create the perfect floor plan for entertaining or family living. The spacious master retreat has a large walk-in closet. Master bath has high ceilings, his & her vanities, a spa tub & separate shower as well as an attached bonus room/office or gym. Excellent schools & low traffic streets w/ sidewalks are just a few amenities that make this neighborhood so appealing. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$1,050,000
$3,890/mo
Monthly Payment:
$3,890
Principal & Interest:
$3,890
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $210,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,606sq ft $291 / sq ft SFR
Lot Size14,118sq ft Built1992 On Site23days
Elegant traditional home in heart of the Via’s on prime brick street… This home greets you with a grand 2-story foyer, extensive wood work/moldings, beautiful... more
Elegant traditional home in heart of the Via’s on prime brick street… This home greets you with a grand 2-story foyer, extensive wood work/moldings, beautiful hardwood floors, plantation shutters, French doors, light & bright home, gorgeous new modern island kitchen w/ stainless appliances & marble counters open to gathering room w/ fireplace & built ins…. Master suite on main level with new lavish master bath along with separate library with closet & built-ins (could be used as a 4th bedroom)… additionally a formal living room & separate dining room for entertaining… Upstairs includes 2 more large bedroom suites along with bonus rooms, and extensive storage… Outdoor living includes an oversized covered lanai open to a large fenced yard (plenty of room for a pool if desired) and private oversized 2-car detached garage… lush landscaping and mature oaks complete this wonderful property… There is room for potential expansion of this home as well… Convenient to ICC, WPRC, Phelps Park & YMCA all nearby! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$775,000
$2,911/mo
Monthly Payment:
$2,911
Principal & Interest:
$2,871
HOA Dues:
$40
(Based on a 30 year fixed loan at 3.75% with $155,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,020sq ft $257 / sq ft SFR
Lot Size32,273sq ft Built1978 On Site23days
A traditional home with a contemporary touch, this beautiful Winter Park home is situated on 3/4 of an acre, sloping to Howell Creek with views of Mead Gardens. The interior... more
A traditional home with a contemporary touch, this beautiful Winter Park home is situated on 3/4 of an acre, sloping to Howell Creek with views of Mead Gardens. The interior features a split plan, a 16 x 18 eat-in kitchen with granite, stainless, & abundant cabinet space, open to the breakfast area and family room. The stone hearth & fireplace are visual points, as well as the floor to ceiling windows, which make this room so dramatic, yet inviting and comfortable. The 18 x 30 master bedroom is privately situated with a sitting area, intimate covered patio, large built-out custom closet & well appointed master bath. Stepping outside reveals not only additional living area, but a breathtaking escape to outdoor relaxation and nature! So beautiful... the extensive screened area, the lawn, the gardens, and creek invite the joy of Florida living! Come view this extraordinary home - you'll be delighted! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$123,900
$769/mo
Monthly Payment:
$769
Principal & Interest:
$459
HOA Dues:
$310
(Based on a 30 year fixed loan at 3.75% with $24,780 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,322sq ft $94 / sq ft CND
Lot SizeN/Asq ft Built1970 On Site25days
Welcome Home to a Quaint and RARE 3 bedroom 2 full bathroom condo in Winter Park, Florida! New and neutral carpet in a 3 good size bedrooms. Location is fabulous and nestled in... more
Welcome Home to a Quaint and RARE 3 bedroom 2 full bathroom condo in Winter Park, Florida! New and neutral carpet in a 3 good size bedrooms. Location is fabulous and nestled in a highly desired school district. New A/C in 2014. Incredible location near Publix, Ward Park, Whole Foods, Rollins, Full Sail, Crealde and uses Winter Park utilities. Tile in Dining room, Living room, Kitchen, Hallway, and Bathrooms. Inside Washer/Dryer hook-up for your convenience. Screened and covered front entry as well as a screened patio overlooking a lush landscape and green space. End corner unit has lots of windows with natural light and views over Ward Park. This condo association offers wonderful amenities such as a community room, tennis court and 3 pools! less
Listing Provided Courtesy of Starlink Realty Of Orlando
Popularity
$325,000
$1,204/mo
Monthly Payment:
$1,204
Principal & Interest:
$1,204
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $65,000 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,887sq ft $172 / sq ft SFR
Lot Size10,387sq ft Built1961 On Site26days
**Real Estate is about LOCATION and WINTER PARK is the Location for this Fabulous Ranch Style Home** The community of Brookshire has a **Desirable SCHOOL District**, access to... more
**Real Estate is about LOCATION and WINTER PARK is the Location for this Fabulous Ranch Style Home** The community of Brookshire has a **Desirable SCHOOL District**, access to Cady way trail, recreation, shopping, entertainment and close to hospitals. The mature landscaping and oak trees provide a canopy of shade as you take an evening stroll. ** WELL MAINTAINED ** SPACIOUS ** OPEN AND AIRY ** This **CHARMING** home has many features. The Kitchen is **BRIGHT** with plenty of cabinets and counter space. Appliances are included. Ceramic tile flows from room to room and carpet softens the generous bedroom floors. Two wood burning fireplaces will add a touch of enchantment to your décor. With the split floor plan, you can retreat to the master suite through your own French doors. Both bathrooms have been upgrade with ceramic tile and a designer vanity. Located on a corner lot, the **OVERSIZED** two car garage has a third door and additional driveway on the side of the home providing **CONVENIENCE** in parking. Exquisite landscaping, privacy fence, trillium, humble patio are all a bonus. Schedule your showing. less
Listing Provided Courtesy of Keller Williams Advantage 2
Popularity
$499,000
$1,848/mo
Monthly Payment:
$1,848
Principal & Interest:
$1,848
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $99,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,209sq ft $226 / sq ft SFR
Lot Size6,750sq ft Built1945 On Site26days
Charming four bedroom home, paver driveway, w/wood and tile floors, formal living room with fireplace, stainless steel appliances, great room w/ vaulted ceilings, wet bar +... more
Charming four bedroom home, paver driveway, w/wood and tile floors, formal living room with fireplace, stainless steel appliances, great room w/ vaulted ceilings, wet bar + bonus room! Cozy neighborhood on brick one-way tree-lined street. Bike to Winter Park Village and Park Avenue stores. Highly rated school district. less
Listing Provided Courtesy of Ez Choice Associates, Inc
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 1,146sq ft $262 / sq ft SFR
Lot Size5,000sq ft Built1995 On Site26days
Charming 3bed/2bath home in the heart of Winter Park. Excellent school district and just steps to Park Avenue and Hannibal Square. Don't miss this one!
Charming 3bed/2bath home in the heart of Winter Park. Excellent school district and just steps to Park Avenue and Hannibal Square. Don't miss this one! less
Listing Provided Courtesy of Parkland International Realty
Popularity
$74,000
$436/mo
Monthly Payment:
$436
Principal & Interest:
$274
HOA Dues:
$162
(Based on a 30 year fixed loan at 3.75% with $14,800 down)
Winter Park, FL 32789
Orange County School District
1bed 1bath 645sq ft $115 / sq ft CND
Lot Size1,843sq ft Built1969 On Site26days
Amazing property located in Winter Park. This is a newly renovated condo with an open floor plan and beautiful hard wood floors. Lakeside Manor is one of the best managed and... more
Amazing property located in Winter Park. This is a newly renovated condo with an open floor plan and beautiful hard wood floors. Lakeside Manor is one of the best managed and maintained properties with low HOA fees and property taxes. Located on private Lake Killarney, with private boat access and slips available to all residents. This is a MUST see. less
Listing Provided Courtesy of Keller Williams Classic Iii Re
Popularity
$199,900
$740/mo
Monthly Payment:
$740
Principal & Interest:
$740
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $39,980 down)
Winter Park, FL 32792
Goldenrod Orange County School District
3bed 2bath 1,952sq ft $102 / sq ft SFR
Lot Size9,874sq ft Built1976 On Site26days
Short sale
Short sale less
Listing Provided Courtesy of Red Carpet Realty Llc
Popularity
$739,000
$2,737/mo
Monthly Payment:
$2,737
Principal & Interest:
$2,737
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $147,800 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,120sq ft $237 / sq ft SFR
Lot Size9,110sq ft Built2015 On Site27days
Come enjoy this spacious 2 story home in the heart of Winter Park. This beautifully designed and appointed home has plenty of space with its 4 bedrooms, 3.5 baths, study, bonus... more
Come enjoy this spacious 2 story home in the heart of Winter Park. This beautifully designed and appointed home has plenty of space with its 4 bedrooms, 3.5 baths, study, bonus room, covered lanai, and plenty of storage space. It also boasts the newest David Weekley "Energy Saver" construction science that used Double Pane/Low-E II Vinyl Windows, Seer 14 A/C system, R-38 blown fiberglass insulation and many other energy-saving features. You will enjoy living among such timeless and elegant upgrades as distressed hardwood flooring that extends throughout the main living spaces and into the owners retreat; full overlay, glazed and raised panel cabinets with crown moulding and beveled knobs in the kitchen and bathrooms and electrical pre-wiring for wall mounted interior electronics. This home is destined to truly enhance the lives of its future owners. Our Energy Saver Homes offer Homebuyers the best in energy-efficiency and are backed by our program's heating and cooling energy usage guarantee. These homes are friendlier to you, the environment and your pocketbook! less
Listing Provided Courtesy of Weekley Homes Realty Company
Popularity
$163,000
$603/mo
Monthly Payment:
$603
Principal & Interest:
$603
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $32,600 down)
Winter Park, FL 32789
2bed 2bath 1,160sq ft $141 / sq ft CND
Lot Size5,612sq ft Built1986 On Site28days
Small condo community on Lake Killarney with dock and lakeside pool area. Walk to shops including Trader Joe's, New Publix and the Winter Park Village with all it's restaurants... more
Small condo community on Lake Killarney with dock and lakeside pool area. Walk to shops including Trader Joe's, New Publix and the Winter Park Village with all it's restaurants and entertainment. This is a delightful first floor condo with tile floors throughout and impeccable decorating on the interior. End unit with it's own designated one car carport plus extra storage. less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
$1,199,000
$4,442/mo
Monthly Payment:
$4,442
Principal & Interest:
$4,442
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $239,800 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,550sq ft $338 / sq ft SFR
Lot Size9,200sq ft Built2015 On Site29days
This fabulous “French Country” style 4 bed/ 3.1 bath pool home meticulously constructed by Austin Homes focuses on clean lines w/ top quality natural materials &... more
This fabulous “French Country” style 4 bed/ 3.1 bath pool home meticulously constructed by Austin Homes focuses on clean lines w/ top quality natural materials & finishes. From the moment you enter this home you will notice the soft colors & natural earth tones which create a soothing & comfortable environment perfect for family gatherings & casual entertaining. Brick walls are featured on the exterior & throughout this exquisite home. Spacious gathering room w/ cozy fireplace overlook the gourmet kitchen w/ Wolf & Sub Zero stainless steel appliances & light & bright dining room. First floor also features a wonderful master retreat & formal living, laundry & powder bath. Second floor has 3 bedrooms, 2 baths, a bonus room & 2nd laundry. Spacious lanai & summer kitchen overlook the sparkling pool, heated spa & private back yard. Additional amenities include: custom cabinetry, top of the line plumbing fixtures, granite counter tops, hardwood floors, high ceilings, gas fireplace & appliances. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
3 4 5 6 7 8 9 10 11 ... 16 26
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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: Monday, July 27, 2015 at 7:59 PM. Properties in listings may have been sold or may no longer be available.