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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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$438,000
$1,622/mo
Monthly Payment:
$1,622
Principal & Interest:
$1,622
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $87,600 down)

1609 Golfside Drive NEW Added to the site in the last 3 days

Winter Park, FL 32792
Golfside Orange County School District
3bed 2bath 2,830sq ft $155 / sq ft SFR
Lot Size9,228sq ft Built1987 On Site1days
You Must See this City of Winter Park Executive Golf Course 2 story home. The home is approximately 2900 sq ft under roof designed for entertaining and leisure activities.... more
You Must See this City of Winter Park Executive Golf Course 2 story home. The home is approximately 2900 sq ft under roof designed for entertaining and leisure activities. Featuring 3 bedrooms and 2 Bathrooms. The Master suite is upstairs and the 2 bedrooms are downstairs. The spacious Master bedroom suite is 24 X 17 with also a 18 X 8 Master closet and additional cedar lined closet. Enjoy the large Family Room with new Wood Floors and Beautiful Stone Wood Burning Fireplace. Entertaining will be fabulous using the Gourmet Kitchen along with granite counter tops and large center Island with prep sink. You can sit outside on your 50 X12 screened porch overlooking the water and 2 picturesque golf holes. The private back yard is bordered by a PVC Custom Fence and Sundeck. Both the front and back and yards are flawlessly manicured along being equipped with a well and irrigation system less
Listing Provided Courtesy of Charles Rutenberg Realty
Popularity N/A
We show you every available listing. Here's how
$255,000
$979/mo
Monthly Payment:
$979
Principal & Interest:
$944
HOA Dues:
$35
(Based on a 30 year fixed loan at 3.75% with $51,000 down)

3337 Bennington Court NEW Added to the site in the last 3 days

Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,806sq ft $141 / sq ft SFR
Lot Size8,677sq ft Built2003 On Site1days
Winter park! Bennington private neighborhood! Located on cul-de-sac street! The floor plan features 3 bedrooms with 2 baths plus a den that could be 4th bedroom. Screen enclosed... more
Winter park! Bennington private neighborhood! Located on cul-de-sac street! The floor plan features 3 bedrooms with 2 baths plus a den that could be 4th bedroom. Screen enclosed porch with brick pavers and fenced yard. Crown moldings and designer touches through out! Beautifully updated and well maintained home! You will not be disappointed, this is a must see! Located just minutes from shopping, restaurants, ucf and major roads! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity N/A
$249,000
$922/mo
Monthly Payment:
$922
Principal & Interest:
$922
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $49,800 down)

2024 Gunn Road NEW Added to the site in the last 3 days

Winter Park, FL 32792
Orange County School District
3bed 2bath 1,570sq ft $159 / sq ft SFR
Lot Size9,827sq ft Built1957 On Site2days
Kenilworth Shores charmer ready for updating. Great location on dead end street. Home features spacious living and dining area with unique parquet wood flooring. Family room... more
Kenilworth Shores charmer ready for updating. Great location on dead end street. Home features spacious living and dining area with unique parquet wood flooring. Family room with sliding glass door overlooking covered patio, and fenced back yard. Chef's eat-in kitchen offers plenty of counter space, wood cabinetry, & tile flooring. Master suite complete with ample closet, and in suite bath. Two additional bedrooms offer parquet flooring, & nice sized closets. Rear yard has room for a pool, and features a storage shed, fully fenced, and covered patio for entertaining. Two car carport with laundry room and storage closet. Fresh paint outside, and lots of tropical landscape complete this Winter Park home. Close to eateries, entertainment, and all major highways. Call today for your private showing. less
Listing Provided Courtesy of Keller Williams Winter Park
Popularity N/A
$132,500
$737/mo
Monthly Payment:
$737
Principal & Interest:
$490
HOA Dues:
$247
(Based on a 30 year fixed loan at 3.75% with $26,500 down)

2489 Tahoe Circle #2489 NEW Added to the site in the last 3 days

Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,311sq ft $101 / sq ft CND
Lot Size2,049sq ft Built1981 On Site2days
Welcome home to this wonderful condo tucked in on a quiet tree lined street in Cedarwood Village. One of Winter Parks best kept secrets! This particular unit in Cedarwood... more
Welcome home to this wonderful condo tucked in on a quiet tree lined street in Cedarwood Village. One of Winter Parks best kept secrets! This particular unit in Cedarwood Village is unique offering three bedrooms with a split floor plan. It’s also an end unit offering extra light and privacy. It has a vaulted ceiling in the great room that includes a cozy wood-burning fireplace. Also great for entertaining, is the tiled patio space with French Doors leading out to your own private space. It’s in MOVE IN condition with newer carpeting, window treatments, and updated kitchen and baths. All the finishes are attractive and neutral ready for your personal items to make it feel like your very own. In addition, the community offers a community pool, club house and tennis courts. The location is superb as you can easily walk to shopping, restaurants and the supermarket. It has easy access to major highways, universities and downtown Winter Park and Downtown Maitland. Hurry and don’t miss this opportunity to purchased a real gem. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$193,980
$718/mo
Monthly Payment:
$718
Principal & Interest:
$718
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $38,796 down)

1867 Shadyhill Terrace NEW Added to the site in the last 3 days

Winter Park, FL 32792
Seminole County School District
3bed 3bath 1,811sq ft $107 / sq ft SFR
Lot Size9,901sq ft Built1987 On Site2days
This property is bank owned. It is sold in “as-is” condition without repairs or warranty. Buyer is responsible for verifying all information contained in this... more
This property is bank owned. It is sold in “as-is” condition without repairs or warranty. Buyer is responsible for verifying all information contained in this listing. less
Listing Provided Courtesy of Owners.com
Popularity
$499,900
$1,852/mo
Monthly Payment:
$1,852
Principal & Interest:
$1,852
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $99,980 down)

1050 Aloma Avenue NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
3bed 2bath 2,112sq ft $237 / sq ft SFR
Lot Size9,745sq ft Built1987 On Site3days
Open Sun Aug 2, 1pm-3pm
Back on the market!!! Freshly painted light and bright exterior and new price!! Beautifully remodeled home in the heart of Winter Park. Just steps from Rollins College and... more
Back on the market!!! Freshly painted light and bright exterior and new price!! Beautifully remodeled home in the heart of Winter Park. Just steps from Rollins College and conveniently located to fabulous Park Ave. Step inside the gated entry through the double front doors to a spacious great room with vaulted ceilings and a fireplace with marble surround. The kitchen has tons of cabinet space with marble countertops a huge island and space for a large dining table. Master bedroom has French doors that open to the fenced in back yard with a sparkling pool and wood deck. Master bathroom boasts dual sinks and an oversized shower with a rainfall shower head and glass doors as well as huge walk in closet. On the other side of the house sits 2 additional bedrooms and a nicely appointed guest bath. Nothing has been spared in making this home like new, schedule a showing today! less
Listing Provided Courtesy of National Real Estate Llc
Popularity
$142,500
$527/mo
Monthly Payment:
$527
Principal & Interest:
$527
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $28,500 down)

2137 Linden Road NEW Added to the site in the last 3 days

Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,242sq ft $115 / sq ft SFR
Lot Size7,826sq ft Built1958 On Site3days
This home is a great opportunity for 1st. time home buyer, or an investor. At this time we are accepting Cash and conventional offers. The sellers will be doing several things... more
This home is a great opportunity for 1st. time home buyer, or an investor. At this time we are accepting Cash and conventional offers. The sellers will be doing several things to make it move in ready, and available to FHA & VA buyers. The list of items that the sellers are going to work on are: Replace Fan Lights, Remove fan light from kitchen and replace with LED, Treat yard for termites, fill & paint interior, paint exterior soffits & wood trim, remove AC wall unit from Baster Bedroom & refinish, replace both toilets, fix soap dish in shower, and wax the wood floors. The roof was replaced in December 2014. New AC unit installed April 2013. The Stove and dishwasher are new July 2015. Thermal pained windows installed, and the septic tank was just pumped & inspected. The drain field was replaced in 2008. WOW... Look At That List! Now is the time, if you are a cash or conventional buyer, to get a great opportunity! Once this is ready for FHA & VA it will go very quickly! less
Listing Provided Courtesy of Keller Williams Heritage Rlty
Popularity
$95,000
$443/mo
Monthly Payment:
$443
Principal & Interest:
$351
HOA Dues:
$92
(Based on a 30 year fixed loan at 3.75% with $19,000 down)

1124 Park Green Place NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
3bed 2bath 1,282sq ft $74 / sq ft TWN
Lot Size3,490sq ft Built1991 On Site3days
Location! Location! 2 bedroom, 2 baths, in sought after park green with over 1700 square feet! Come see this spacious townhome with open floor plan, natural light & easy to... more
Location! Location! 2 bedroom, 2 baths, in sought after park green with over 1700 square feet! Come see this spacious townhome with open floor plan, natural light & easy to maintain ceramic tile in the main living areas! Blinds cover the sliding glass doors which open to your private, fenced, back yard. Kitchen is open & bright and dishwasher, microhood and refrigerator all stay! Plenty of storage space in the attached two car garage and attic with stair access. Exemplary fine dining and shopping are very close – winter park village and boutiques & fine dining on park ave are mere minutes away. This area has super easy access to major highways for commuters, oia and local attractions! Hoa $92 monthly taxes: only $1592! less
Listing Provided Courtesy of Re/max 200 Realty
Popularity
$525,000
$1,945/mo
Monthly Payment:
$1,945
Principal & Interest:
$1,945
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $105,000 down)

1488 Aster Court NEW Added to the site in the last 3 days

Winter Park, FL 32792
Seminole County School District
3bed 2bath 2,031sq ft $258 / sq ft SFR
Lot Size16,677sq ft Built1984 On Site3days
Winter park- lakefront on approximately 1/2 acre! outstanding renovations- shows like a model! Magnificent dream kitchen w/ large island , great prep area, also serves... more
Winter park- lakefront on approximately 1/2 acre! outstanding renovations- shows like a model! Magnificent dream kitchen w/ large island , great prep area, also serves as a breakfast area table! Granite, upgraded 42 inches cabinets with pull outs & upgraded appliances. Opens to superb living room! Travertine floors & wood floors throughout! Wet bar, eat-in area. Spacious family room with wood burning fireplace & additional bonus room, french doors, park like setting, spacious patio with pavers, lavish landscaping. Lakefront, dock & custom exterior landscape lighting & much more! Luxurious master suite! New baths with custom vanities! New roof 3 yrs! brand new ac! Cul-de-sac! Hurry! Won't last!!! less
Listing Provided Courtesy of Keller Williams Heritage Rlty
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
2,582sq ft $193 / sq ft MFR
Lot Size5,910sq ft Built2005 On Site4days
Fantastic Investment Opportunity!!! Located just two blocks from Rollins College and Park Avenue. Four bedrooms, two and one-half baths, gorgeous hardwood floors and beautiful... more
Fantastic Investment Opportunity!!! Located just two blocks from Rollins College and Park Avenue. Four bedrooms, two and one-half baths, gorgeous hardwood floors and beautiful crown molding throughout. Kitchen features custom cabinetry, granite countertops, breakfast bar, and stainless steel appliances. Living room offers French doors that lead to the covered porch, a wood-burning fireplace and an open floorplan great for entertainment. Downstairs master suite has private garden bath, with dual vanities, garden tub and walk-in shower. Three bedrooms upstairs as well as an open bonus room. Absolutely beautiful home. Walk to the Farmer’s Market, Rollins College, Park Avenue shops and dining, and more. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$315,000
$1,167/mo
Monthly Payment:
$1,167
Principal & Interest:
$1,167
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $63,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size6,512sq ft BuiltN/A On Site4days
This generously sized 1532sqft 3 bedroom 2 bathroom home is set on a 6,504sqft lot. Carpet and ceramic tile throughout the home. Located in the beautiful Winter Park this home... more
This generously sized 1532sqft 3 bedroom 2 bathroom home is set on a 6,504sqft lot. Carpet and ceramic tile throughout the home. Located in the beautiful Winter Park this home is moments from the iconic Park Avenue and Rollins College and a wonderful school district. Spacious yard and attached garage with additional parking in driveway. Contact me today to learn more about your forever home! less
Listing Provided Courtesy of Olde Town Brokers Inc
Popularity
$135,000
$500/mo
Monthly Payment:
$500
Principal & Interest:
$500
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $27,000 down)
Winter Park, FL 32792
2bed 2bath 1,219sq ft $111 / sq ft CND
Lot Size19.0acre Built1970 On Site4days
HOA, Includes water, sewer, garbage collection, 3 pools, lawn maintenance, tennis courts, shuffleboard, and car wash. Highly desired area.
HOA, Includes water, sewer, garbage collection, 3 pools, lawn maintenance, tennis courts, shuffleboard, and car wash. Highly desired area. less
Listing Provided Courtesy of Assist 2 Sell Veterans Realty
Popularity
$119,900
$444/mo
Monthly Payment:
$444
Principal & Interest:
$444
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $23,980 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 1,127sq ft $106 / sq ft CND
Lot Size19.0acre Built1970 On Site4days
Walk to Publix, pharmacies, banks within the area. Short Drive to Park ave, Farmer's Market. Close to Full Sail.
Walk to Publix, pharmacies, banks within the area. Short Drive to Park ave, Farmer's Market. Close to Full Sail. less
Listing Provided Courtesy of Winter Park Land Co.
Popularity
$115,000
$697/mo
Monthly Payment:
$697
Principal & Interest:
$426
HOA Dues:
$271
(Based on a 30 year fixed loan at 3.75% with $23,000 down)
Winter Park, FL 32789
Garden Acres Orange County School District
2bed 2bath 893sq ft $129 / sq ft CND
Lot Size13,119sq ft Built1967 On Site4days
Nicely done 2/2 located near Mead Gardens and very close to downtown Winter Park and Orlando. Newer paint and carpet. Ideal location in Winter Park. Unit overlooks nicely... more
Nicely done 2/2 located near Mead Gardens and very close to downtown Winter Park and Orlando. Newer paint and carpet. Ideal location in Winter Park. Unit overlooks nicely landscaped pool area. Grounds have mature landscaping. Laundry facility close to unit. less
Listing Provided Courtesy of Central Florida Land Co Llc
Popularity
$899,000
$3,330/mo
Monthly Payment:
$3,330
Principal & Interest:
$3,330
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $179,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,384sq ft $266 / sq ft SFR
Lot Size9,009sq ft Built2015 On Site4days
Olde winter park welcomes another lundev fabulous new custom home! This quiet location on a tree-lined cul-de-sac offers contemporary quality touches while offering energy... more
Olde winter park welcomes another lundev fabulous new custom home! This quiet location on a tree-lined cul-de-sac offers contemporary quality touches while offering energy efficient features. Covered entryway welcomes you inside to be greeted with designer wood floors. This family home offers a large gathering area with a spacious family room complete with a gas fireplace. The gourmet kitchen offers bosch appliances centered around a large kitchen island topped with a beautiful granite top amid custom maple cabinetry. Venture outside to a covered patio overlooking the yard with room for a pool. Luxurious first floor master bedroom offers plenty of storage in the large walk-in closet while the mbr bath features his and her vanities with a garden tub and separate shower stall. There's a second br also on the first floor . Privacy awaits in the downstairs library/den for family chats. Upstairs you'll find two additional bedrooms and a loft - perfect for a playroom or media room. This location is a short bike ride to famed park ave. And offers a schools: dommerich elem/maitland mid/wp high. Easy commuter access to 417. Call today for your private showing! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
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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
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: Friday, July 31, 2015 at 7:57 PM. Properties in listings may have been sold or may no longer be available.