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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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$795,000
$2,945/mo
Monthly Payment:
$2,945
Principal & Interest:
$2,945
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $159,000 down)
Winter Park, FL 32789
Orange County School District
4bed 2bath 3,402sq ft $234 / sq ft SFR
Lot Size29,111sq ft Built1941 On Site31days
Prime olde Winter Park location near Lake Sue… Build your dream home on this almost 30,000 sq.ft. corner lot on one of Winter Park’s most beautiful brick streets.... more
Prime olde Winter Park location near Lake Sue… Build your dream home on this almost 30,000 sq.ft. corner lot on one of Winter Park’s most beautiful brick streets. This lot is apprx. 150 x 200 and only one house off of Lake Sue so there is potential for lake views from a newly designed home… This gorgeous property is built up from the streets so you can enjoy an elevated setting. Although no value is placed on the existing house/structure sitting on property, the kitchen in the house was completely new 4 years ago with quality cabinets and granite. Some of the cabinets and countertops could be reused. A beautiful pool was installed in 1999 at the back of the lot. Lots this large do not come along very often in Winter Park so don’t miss this great opportunity! Convenient location to hospitals, Lake Highland Prep, downtown Orlando, Rollins College, and Park Avenue. Winter Park “A” rated schools… less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
Your search results are current and complete. Learn more
$795,000
$2,945/mo
Monthly Payment:
$2,945
Principal & Interest:
$2,945
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $159,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size29,111sq ft BuiltN/A On Site31days
Prime olde Winter Park location near Lake Sue… Build your dream home on this almost 30,000 sq.ft. corner lot on one of Winter Park’s most beautiful brick streets.... more
Prime olde Winter Park location near Lake Sue… Build your dream home on this almost 30,000 sq.ft. corner lot on one of Winter Park’s most beautiful brick streets. This lot is apprx. 150 x 200 and only one house off of Lake Sue so there is potential for lake views from a newly designed home… This gorgeous property is built up from the streets so you can enjoy an elevated setting. Although no value is placed on the existing house/structure sitting on property, the kitchen in the house was completely new 4 years ago with quality cabinets and granite. Some of the cabinets and countertops could be reused. A beautiful pool was installed in 1999 at the back of the lot. Lots this large do not come along very often in Winter Park so don’t miss this great opportunity! Convenient location to hospitals, Lake Highland Prep, downtown Orlando, Rollins College, and Park Avenue. Winter Park “A” rated schools… less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$1,499,900
$5,557/mo
Monthly Payment:
$5,557
Principal & Interest:
$5,557
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $299,980 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,085sq ft $367 / sq ft SFR
Lot Size11,998sq ft Built2016 On Site31days
Pre construction! This magnificent british west indies estate home awaits your final touches. A soaring 2 story foyer greets you with views of the pool as you enter this very... more
Pre construction! This magnificent british west indies estate home awaits your final touches. A soaring 2 story foyer greets you with views of the pool as you enter this very special home. The large, open kitchen features thermador appliances and a huge island with seating for 6 that overlooks the great room. There are beautiful coffered ceilings in the dining room which is large enough to hold a table for 12! The private master retreat is located on the first floor and has dual closets, a large shower, a freestanding tub and separate vanities. There is second bedroom adjacent to the master that could be used as a study, nursery or guest suite. Upstairs, there are three large en suite bedrooms with a loft in the center that leads to a stunning covered balcony for more entertaining possibilities. This home also has numerous energy features including spray foam isolation, a standing seam metal roof, tank less hot water heaters, and smart home technology pre wired to run the lighting, security and hvac systems at the touch of your smart phone or tablet. This home is located on a lovely brick street in one of the most sought after neighborhoods in winter park with "a" rated schools and proximity to everything winter park has to offer. Call today for plans and specs and a personal preview of this fantastic residence. less
Listing Provided Courtesy of Coledev Real Estate Llc
Popularity
$565,000
$2,093/mo
Monthly Payment:
$2,093
Principal & Interest:
$2,093
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $113,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 3,435sq ft $164 / sq ft SFR
Lot Size21,000sq ft Built1926 On Site32days
Residential Compound! Winter Park historic Home with separate Office suite and private Apartment to the rear of the property, great for rental income or multi-family. This... more
Residential Compound! Winter Park historic Home with separate Office suite and private Apartment to the rear of the property, great for rental income or multi-family. This Spanish villa style Main house was built in 1926 and is 2 bed/ 2 bath. Enter into history… large Living room with original hand cut wood floors, chic crystal accent lighting and gas fireplace. Delightful Dining room with designer wall sconces and chandelier. Large remodeled Kitchen is light and bright and opens to the Family room – perfect for family gatherings. Also on main level is a secondary Bedroom with a full bath. Master Bedroom is on the second floor and features built-in wardrobe cabinets and a fireplace. The Master features a romantic window lined turret, perfect for sitting area or desk. The separate Office is attached to the Guest House and has a full bath, tall ceilings, French doors & accent lighting. The complete Guest House in the rear has Mexican tile floors and is a 2 bed/ 2 bath with living room, dining area, full kitchen and own laundry. All sits on a triple lot measuring 140 x 150 with circular drive, 3 car carport & plenty of room for additional parking. Plenty of room to expand, add a pool and/or a 3 car garage. The east third of the property is like a park with zoysia grass and is completely fenced & gated. Great multi-family situation. This property has been a wonderful rental investment property and can be yours too! Easy access to I-4, both downtown Winter Park & downtown Orlando and to Florida Hospital. less
Listing Provided Courtesy of Parkland International Realty
Popularity
$210,000
$778/mo
Monthly Payment:
$778
Principal & Interest:
$778
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $42,000 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,669sq ft $126 / sq ft SFR
Lot Size6,955sq ft Built1956 On Site32days
Short Sale. Welcome to one of the best citied to live in, Winter Park. Close to great schools, Park Ave, Rollins College and many entertainment such as Disney, Universal,... more
Short Sale. Welcome to one of the best citied to live in, Winter Park. Close to great schools, Park Ave, Rollins College and many entertainment such as Disney, Universal, SeaWorld and more. Winter Park is a heavy desirable area to live in, take a look at this property asap. When you walk in thru your front door, your amazed at the living room style and ceramic tiles. Walking thru the living room and to the left are two bedrooms with a bathroom. On the other side of the living room you reach the gourmet kitchen. Have fun entertaining and preparing great meals to eat, and enjoy you separate dining area next to the kitchen. Fit a beautiful dining table and enjoy your thanksgiving diner you've always wanted with your loved ones. Your bonus room can be changed to a 4th bedroom by adding a closet or keep it as is and use as an office, play area, game room, or anything you've always wanted to have in your home. Walking pass the kitchen you come to a separate loft, relax or set up another area of you choosing such as a game room, play area. Next to the loft you have your washer and dryer hook up area, and your master bedroom. The master bedroom show with ample space for any size furniture, go king if you want to, and you own private walk in closet and separate bathroom. This is a great property to own, and with your love it will become a home. less
Listing Provided Courtesy of Exit Realty Central
Popularity
$949,000
$3,515/mo
Monthly Payment:
$3,515
Principal & Interest:
$3,515
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $189,800 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 3,266sq ft $291 / sq ft SFR
Lot Size9,221sq ft Built1999 On Site32days
Don’t miss this beautiful New Orleans style home in the “heart of Winter Park”. This 5bdrm/5bath pool home boasts quality throughout. From the minute you... more
Don’t miss this beautiful New Orleans style home in the “heart of Winter Park”. This 5bdrm/5bath pool home boasts quality throughout. From the minute you pull into the driveway, you will feel at home. The expansive front porches are perfect for morning coffee or for visiting with neighbors. This lovely home features beautiful tongue and groove hardwood floors, crown molding, plantation shutters, downstairs office with bath (could also be a bedroom), downstairs master suite. The kitchen and family room combination are perfect for entertaining. The family room is warm and inviting with a brick gas or wood burning fireplace. The ceilings and windows in the family expand to the 2nd floor so extra light shines through. You will love cooking in the lovely kitchen featuring a gas cooktop, double ovens, warming drawer, newer refrigerator and dishwasher, granite countertops and a fabulous breakfast nook overlooking the pool and backyard. If you need a private guest suite, bonus room or a separate office, the flex space above the garage is the perfect place. The pool area is an oasis featuring a saltwater pool, extensive brick patio, full bath and beautiful landscaping. Many upgrades include brand new landscaping, updated kitchen countertops, replaced two bathroom vanities, newer pool equipment and refinished floors. Walking distance to Phelps Park and Park Avenue. Winter Park “A” Schools. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$665,000
$2,463/mo
Monthly Payment:
$2,463
Principal & Interest:
$2,463
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $133,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,780sq ft $239 / sq ft SFR
Lot Size7,494sq ft Built2008 On Site34days
Beautiful, newer 4/2.5 on wonderful brick­lined Winter Park Street. Modern clean lines interior and open floor plan with exceptional stacked marble wall in the... more
Beautiful, newer 4/2.5 on wonderful brick­lined Winter Park Street. Modern clean lines interior and open floor plan with exceptional stacked marble wall in the foyer. Kitchen flows into bright living room with vaulted ceilings, stacked marble Eco­Smart gas fireplace, custom built­ins and custom window treatments. Downstairs Master Suite with custom walk­in closet, beautiful bath with dual sinks, jetted tub and large glass walk­in shower. Three additional bedrooms upstairs with ample closet space, Jack­and­Jill bath, plus bright bonus room/loft. Granite countertops and wood floors throughout, newly installed hand­scraped Spanish wood on second floor, crown molding, tankless hot water heater, double pane windows, downstairs laundry room, stainless steel appliances, detached 2­car garage, meticulously landscaped back yard with organic garden beds and much more. Enjoy contemporary living near Lakemont YMCA, Phelps Park, top rated Winter Park Schools, and Whole Foods. Priced right, so call today for your private showing! less
Listing Provided Courtesy of Murphy Properties Llc
Popularity
$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)
Winter Park, FL 32792
Golfside Orange County School District
3bed 2bath 2,830sq ft $155 / sq ft SFR
Lot Size9,228sq ft Built1987 On Site34days
Open Sat Sep 5, 1pm-4pm
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
$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)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,806sq ft $141 / sq ft SFR
Lot Size8,677sq ft Built2003 On Site34days
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 an extended patio. 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
$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)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,570sq ft $159 / sq ft SFR
Lot Size9,827sq ft Built1957 On Site35days
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 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
$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)
Winter Park, FL 32792
Seminole County School District
3bed 3bath 1,811sq ft $107 / sq ft SFR
Lot Size9,901sq ft Built1987 On Site35days
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)
Winter Park, FL 32789
Orange County School District
3bed 2bath 2,112sq ft $237 / sq ft SFR
Lot Size9,745sq ft Built1987 On Site36days
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... more
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
$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)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 2,031sq ft $258 / sq ft SFR
Lot Size16,677sq ft Built1984 On Site36days
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
$495,000
$1,833/mo
Monthly Payment:
$1,833
Principal & Interest:
$1,833
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $99,000 down)
Winter Park, FL 32789
Orange County School District
2,582sq ft $192 / sq ft MFR
Lot Size5,910sq ft Built2005 On Site37days
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 Site37days
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
4 5 6 7 8 9 10 11 12 ... 17 27
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: Thursday, September 3, 2015 at 2:06 PM. Properties in listings may have been sold or may no longer be available.