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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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$649,000
$2,404/mo
Monthly Payment:
$2,404
Principal & Interest:
$2,404
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $129,800 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,173sq ft $299 / sq ft SFR
Lot Size12,002sq ft Built1957 On Site32days
Do you want an open floor plan designed for entertaining? Home was totally redone 10 years ago- 10' ceiling heights. Open floor plan. Kitchen is open to family room, home lives... more
Do you want an open floor plan designed for entertaining? Home was totally redone 10 years ago- 10' ceiling heights. Open floor plan. Kitchen is open to family room, home lives bigger than listed square footage. Living room-dining room main room in the center of the home. Private pool, resurfaced in 2014, has a heated spa. Charming master suite. If you want a new home feel without the hassle of building take a look and see what a little paint will accomplish. Neighborhood lots are selling for $300,000+, new homes $1 mil. Overlooks city park that is shared with windsong neighborhood. less
Listing Provided Courtesy of Winter Park Land Co.
Popularity N/A
We show you every available listing. Here's how
$65,000
$601/mo
Monthly Payment:
$601
Principal & Interest:
$240
HOA Dues:
$361
(Based on a 30 year fixed loan at 3.75% with $13,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,149sq ft $57 / sq ft CND
Lot Size17,764sq ft Built1966 On Site32days
3 bedrooms, 2 bathrooms condo in Winter Park. Great floor plan with living and dinning room combo with carpet and tile flooring. New AC in 2014. Community features: pool,... more
3 bedrooms, 2 bathrooms condo in Winter Park. Great floor plan with living and dinning room combo with carpet and tile flooring. New AC in 2014. Community features: pool, playground, secured buildings with coded access. Close to shopping, dining, schools, major roads, highway. Leased until Jan 2016. less
Listing Provided Courtesy of La Rosa Realty, Llc
Popularity N/A
$1,800,000
$6,668/mo
Monthly Payment:
$6,668
Principal & Interest:
$6,668
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $360,000 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
N/Asq ft N/A / sq ft LND
Lot Size11.2acre BuiltN/A On Site32days
3 parcels totaling 11+ acres in winter park - 470 feet of road frontage on howell branch road that will offer plenty of exposure in the desirable area. Builders are selling out... more
3 parcels totaling 11+ acres in winter park - 470 feet of road frontage on howell branch road that will offer plenty of exposure in the desirable area. Builders are selling out their communities in less than 6 months and the new san pedro project is only about a mile away ( 900 + new homes ) property could be combined for an equestrian center with live in quarters. This property offers endless possibilities for development and located within minutes of the 417 and downtown winter park..... Call today for more information less
Listing Provided Courtesy of The Titan Group, Inc.
Popularity N/A
$1,375,000
$5,094/mo
Monthly Payment:
$5,094
Principal & Interest:
$5,094
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $275,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,682sq ft $373 / sq ft SFR
Lot Size27,534sq ft Built1999 On Site33days
Key west" style canal home. A rare find--a fantastic winter park location with easy chain of lakes access. This beautifully updated turn-key 4 bedroom, 3 bath, 3682 sf home... more
Key west" style canal home. A rare find--a fantastic winter park location with easy chain of lakes access. This beautifully updated turn-key 4 bedroom, 3 bath, 3682 sf home offers laid back living on one level! A charming chicago brick courtyard with fountain leads into the formal foyer and open living room. Great huge island kitchen with high-end appliances, granite countertops, spacious breakfast area that accommodates a large farm table and separate butler’s pantry. The bedroom plan is split which affords privacy. Large pretty master with sitting area and built-ins, incredible bath, spacious custom closets and dressing area. A cozy family room connects the master to a second bedroom and bath. Two generous bedrooms and tasteful bath on the opposite side of the house. Entertain on the shady screened porch or sunny poolside. Enjoy the pretty walk out to the canal and boat house. Also a generator, mosquito mister, bose speakers throughout and temperature controlled wine closet in one garage. It is even walking distance to park avenue! This home offers the best of the easy winter park walking and water lifestyle! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity N/A
$149,900
$555/mo
Monthly Payment:
$555
Principal & Interest:
$555
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $29,980 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,449sq ft $103 / sq ft SFR
Lot Size11,200sq ft Built1958 On Site33days
Investment property awaits. This property has great potential. Seller will only entertain cash offers. Close to everything! Only a short commute to shopping, entertainment and... more
Investment property awaits. This property has great potential. Seller will only entertain cash offers. Close to everything! Only a short commute to shopping, entertainment and dining. Minutes away from i-4 makes traveling to anywhere easy. less
Listing Provided Courtesy of Carrington Real Estate Service
Popularity N/A
$285,000
$1,055/mo
Monthly Payment:
$1,055
Principal & Interest:
$1,055
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $57,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 3bath 2,110sq ft $135 / sq ft SFR
Lot Size21,780sq ft Built1967 On Site33days
Bring your boat, your RV, your utility trailers, No HOA! 4 bedroom 3 bath 2 car garage home situated on 1/2 acre in Winter Park!! This is truly a rare and unique find. Well... more
Bring your boat, your RV, your utility trailers, No HOA! 4 bedroom 3 bath 2 car garage home situated on 1/2 acre in Winter Park!! This is truly a rare and unique find. Well maintained has easy care/allergy free ceramic tile flooring throughout and a practical floorpan, great for entertaining! The property is adjacent to a canal that feeds into Garden Lake for canoeing or paddle boarding. Great shopping, churches schools and restaurants are close by. In addition, it is convenient to the University of Central Florida, Full Sail University, Rollins College, Oviedo Marketplace, and all of the attractions by way of the 417 expressway. Bike/Jogging trails are nearby as well. Whether your destination is Winter Park, Winter Springs, or Oviedo, this home is in the perfect location for you. See it today! less
Listing Provided Courtesy of Re/max 200 Realty
Popularity N/A
$62,000
$229/mo
Monthly Payment:
$229
Principal & Interest:
$229
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $12,400 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 840sq ft $74 / sq ft CND
Lot Size5,668sq ft Built1990 On Site33days
This is a nice 2 bedroom 2 bath Condo close to Full Sail and UCF Great rental opportunities for investors
This is a nice 2 bedroom 2 bath Condo close to Full Sail and UCF Great rental opportunities for investors less
Listing Provided Courtesy of Re/max Town Centre
Popularity N/A
$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
N/Asq ft N/A / sq ft LND
Lot Size22,726sq ft BuiltN/A On Site33days
Rare opportunity to own a lot of this size on Park Avenue (.52 acre parcel). All the prestige of a Park Avenue address with the convenience of a driveway on New York; the... more
Rare opportunity to own a lot of this size on Park Avenue (.52 acre parcel). All the prestige of a Park Avenue address with the convenience of a driveway on New York; the perfect place to build your "Monopoly" house! Walk to the shops of Park Avenue and the Winter Park Farmers Market. less
Listing Provided Courtesy of Anne Rogers Realty Group Inc
Popularity N/A
$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 3bath 2,610sq ft $459 / sq ft SFR
Lot Size22,726sq ft Built1961 On Site33days
Rare opportunity to own a lot of this size on Park Avenue (.52 acre parcel). All the prestige of a Park Avenue address with the convenience of a driveway on New York. Walk to... more
Rare opportunity to own a lot of this size on Park Avenue (.52 acre parcel). All the prestige of a Park Avenue address with the convenience of a driveway on New York. Walk to the shops of Park Avenue and the Winter Park Farmers Market. The value of this property is in the land but, for the Mid-Century Modern enthusiast, the land comes with a free “60’s-classic” house. Of course the house is included “as is” but it features an 18’x40’ air conditioned atrium, polished terrazzo floors, oversized 2 car garage, and a charming mother-in-law suite. Restore this Mid-Century gem or build a new gem on this wonderful corner lot that sits high on Park Avenue with more than 150 feet of frontage! less
Listing Provided Courtesy of Anne Rogers Realty Group Inc
Popularity N/A
$698,000
$2,589/mo
Monthly Payment:
$2,589
Principal & Interest:
$2,586
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.75% with $139,600 down)
Winter Park, FL 32789
Virginia Heights Orange County School District
3bed 3bath 1,824sq ft $383 / sq ft SFR
Lot Size9,278sq ft Built1935 On Site34days
Historic registered home in desirable Virginia Heights Neighborhood. Beautiful lush /mature landscaping covers the entire property from front to back. This home was featured in... more
Historic registered home in desirable Virginia Heights Neighborhood. Beautiful lush /mature landscaping covers the entire property from front to back. This home was featured in "Southern Living Magazine" in the August 2005 Edition. The 1920's craftsmanship shows and home packed with charm. The main house offers 2 bedroom 2 bath with finished attic that can be used as a 3rd bedroom or bonus room. The basement area can be used for extra storage, etc. Exquisite appointments include crown moldings, plantation shutters, hardwood floors, gas burning fireplace, and Florida room with slate flooring. New roof and AC installed 2014. The brick paved driveway leads to covered parking area. The detached guest house offerers a kitchenette and full bathroom. Enjoy the screened patio area that overlooks the gorgeous saltwater pool. Walk to deeded Lake Virginia, Chain of Lakes access. This home is a true beauty. Completely updated while preserving the feel of the yesteryear. less
Listing Provided Courtesy of Beck Realty Llc
Popularity N/A
$749,000
$2,774/mo
Monthly Payment:
$2,774
Principal & Interest:
$2,774
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $149,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,800sq ft $268 / sq ft SFR
Lot Size10,455sq ft Built1967 On Site35days
Located on a quiet Cul-de-Sac, this unique modern sanctuary offers the optimum blend of form and function. Designed by architect Alan Berman, no detail has been overlooked in... more
Located on a quiet Cul-de-Sac, this unique modern sanctuary offers the optimum blend of form and function. Designed by architect Alan Berman, no detail has been overlooked in this rare home, which offers four spacious bedrooms, three fully remodeled bathrooms, ergonomically re-engineered kitchen, new house systems (irrigation, filtration, lighting, electrical), a pool and private courtyard, multiple living spaces, and a vast array of luxury modern features throughout. Natural elements of sunlight, air and garden views add to this home’s welcoming environment. The light, bright and open kitchen offers clean lines and ergonomic spaces inspired by modern, eco-friendly European design. Remodeled in 2010, the kitchen has been engineered with rigorous attention to detail, including top-of-the-line appliances (Electolux, Miele) and a sense of function and flow. With quartz countertops, Italian tile, wine and beverage refrigerators, and well-lighted environmentally friendly work stations, this kitchen provides an elegant blend of luxury and ease. The home’s clean lines and open, airy feel continue into the living space, the centerpiece of which is an authentically mid-century modern sunken fireplace with built-in seating, straight from the real Mad Men days. The living room features soaring ceilings and new floating beechwood floors. Floor-to-ceiling windows and glass doors bring together the indoor and outdoor, offering direct access to the courtyard with its mature trees and newly resurfaced pool. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity N/A
$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 2,275sq ft $143 / sq ft SFR
Lot Size8,712sq ft Built1962 On Site35days
Two Story contemporary, "Frank Lloyd Wright" architectural style. Soaring ceilings, skylights, remodeled baths. Bright sunroom. Master down. Ceramic-tiled entrance foyer w/... more
Two Story contemporary, "Frank Lloyd Wright" architectural style. Soaring ceilings, skylights, remodeled baths. Bright sunroom. Master down. Ceramic-tiled entrance foyer w/ bright clerestory windows. Spacious living room w/ cathedral ceilings. Formal dining room. Open kitchen for entertaining with light oak cabinetry, generous pantry, ceramic-tile flooring, decorative tile back-splashes, flat-top stove, breakfast bar with brick detail. Inviting sunroom has elegant terra-cotta tile flooring, wet bar, and bright windows. Split 3 bedroom...private master retreat downstairs w/ three walk-in closets and master bath with double vanity. Two large bedrooms upstairs w/lots of closets and remodeled bath. Two-zoned A/C, inside utility. All 'A-rated' schools, including Winter Park High School and Brookshire Elementary. Cady Way Park and Trail is one block away. Convenient to downtown, airport and minutes from great shopping and restaurants. House needs a little TLC, paint and landscaping, nothing major. Owner motivated, bring offers. less
Listing Provided Courtesy of Roman Realty Group, Llc
Popularity N/A
$449,900
$1,766/mo
Monthly Payment:
$1,766
Principal & Interest:
$1,666
HOA Dues:
$100
(Based on a 30 year fixed loan at 3.75% with $89,980 down)
Winter Park, FL 32792
4bed 4bath 2,842sq ft $158 / sq ft SFR
Lot Size10,889sq ft Built2015 On Site36days
Basically brand new home, The Inverness Model features Upgrades galore! Gated Sanctuary at Aloma in Winter Park. This home welcomes you with warm hardwood floors throughout.... more
Basically brand new home, The Inverness Model features Upgrades galore! Gated Sanctuary at Aloma in Winter Park. This home welcomes you with warm hardwood floors throughout. Formal Living and Dining Rooms separate. Top of the line Stainless Steel appliances. Large Over sized Quartz Counter Tops, Upgraded Cabinets with under-mount and interior lighting. Flex Space can be used as Office/Den/Playroom area. Large Master Bedroom, Master Bath features oversized upgraded Shower with Rainfall shower & Dual shower heads and built in bench. His and her Vanities, bidet. Triple Sliders lead to the Large, Covered Screen Porch. Convenient location to Aloma and the 417. 25 minutes to downtown Orlando. Great Schools and more! Call today for your private showing. less
Listing Provided Courtesy of Bhhs Florida Realty
Popularity N/A
$340,000
$1,290/mo
Monthly Payment:
$1,290
Principal & Interest:
$1,259
HOA Dues:
$31
(Based on a 30 year fixed loan at 3.75% with $68,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 3bath 2,632sq ft $129 / sq ft SFR
Lot Size19,777sq ft Built1984 On Site37days
Custom-built home on OVERSIZED LOT in OUTSTANDING Winter Park community. Home boasts an OPEN FLOORPLAN design and generous sized living areas. Home has SOARING CEILINGS and... more
Custom-built home on OVERSIZED LOT in OUTSTANDING Winter Park community. Home boasts an OPEN FLOORPLAN design and generous sized living areas. Home has SOARING CEILINGS and numerous skylights providing FANTASTIC natural light. Master Suite is HUGE, with wood laminate flooring, stone FIREPLACE and bath with DUAL SINKS and a huge DOORLESS WALK-IN SHOWER. The gigantic Florida Room is finished with natural wood ceilings, TILE FLOORS and built-in bar. Space could easily be converted to whichever room best fits your lifestyle. Home has 4 CAR GARAGE and SPACIOUS indoor laundry room with laundry sink. Plenty of room to make this your mudroom/entry too. The POSSIBILITIES with this home are ENDLESS! Convenient location and EXCELLENT SCHOOLS. less
Listing Provided Courtesy of Re/max Town & Country Realty
Popularity N/A
$299,000
$1,107/mo
Monthly Payment:
$1,107
Principal & Interest:
$1,107
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $59,800 down)
Winter Park, FL 32789
Orange County School District
4bed 2bath 2,149sq ft $139 / sq ft SFR
Lot Size10,751sq ft Built1973 On Site37days
Short Sale...(Bank Authorized Short Sale). Attractive, spacious, Winter Park residence. Features include 4 bedrooms, 2 baths, 2-car garage and inviting pool, with over 2,149 sq... more
Short Sale...(Bank Authorized Short Sale). Attractive, spacious, Winter Park residence. Features include 4 bedrooms, 2 baths, 2-car garage and inviting pool, with over 2,149 sq feet of living space and 2,683 sq feet under roof. This property is located on a fenced cul-de-sac lot in a pretty quiet residential neighborhood. There is easy access to major roads, shopping, schools, hospitals and entertainment. less
Listing Provided Courtesy of Realty Executives Seminole
Popularity N/A
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ZipRealty helps you find current homes for sale in Winter Park, FL. We show up to 30% more MLS listings than other websites, including new homes for sale, condos for sale, townhomes for sale, foreclosed homes for sale and land for sale. Set up your unique Winter Park real estate search criteria to see results that match what you're looking for. Explore maps, photos, schools and more to get an idea of what your life would be like in a new neighborhood. Find a local Winter Park real estate agent to work with by reading realtor reviews left by buyers and sellers like you. If you want to know what your home is worth, you can instantly view home values for any address by visiting our Seller Center. If you're planning to sell your home, you can also see how much similar homes are selling for in Winter Park to get an idea of how to price your home.
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
Content 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.

Copyright 2015 Mid-Florida Regional Multiple Listing Service. All rights reserved.

Data last updated: Thursday, May 21, 2015 at 8:23 PM