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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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$969,000
$4,536/mo
Monthly Payment:
$4,536
Principal & Interest:
$3,590
HOA Dues:
$946
(Based on a 30 year fixed loan at 3.75% with $193,800 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,964sq ft $493 / sq ft CND
Lot Size2,562sq ft Built1960 On Site15days
Gutted to the studs, this ground floor, meticulously crafted, 2 bedroom/2 bath condo is perfection. Renovation was completed in 2013 by Nu Design Builders. Serene and... more
Gutted to the studs, this ground floor, meticulously crafted, 2 bedroom/2 bath condo is perfection. Renovation was completed in 2013 by Nu Design Builders. Serene and sophisticated, the open floor plan provides natural light and flexibility. Kitchen, dining and family rooms enjoy expansive view of Lake Osceola. Gourmet kitchen has Thermador appliances, quartzite, natural stone counters, tile backsplash and breakfast bar. Laundry room, located off the kitchen, has a wall of shelving and additional storage. Master bedroom has custom designed walk-in closet and adjoining office nook. Adjoining patio area offers water views and lake breezes. Master bath has dual-headed travertine shower, two sinks, marble countertop and travertine flooring. Secondary bedroom has two closets and sitting area overlooking the pond. Additional amenities include walnut wood flooring throughout living areas, custom cabinetry, crown molding, recessed lighting, and surround sound and security system. Other new features: windows, A/C and ductwork, electrical, insulation and plumbing. This downtown Winter Park condo, in a 55+ community, is a short walk to restaurants, shopping, churches and Rollins College. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
We show you every available listing. Here's how
$2,758,000
$10,445/mo
Monthly Payment:
$10,445
Principal & Interest:
$10,218
HOA Dues:
$227
(Based on a 30 year fixed loan at 3.75% with $551,600 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 6,757sq ft $408 / sq ft SFR
Lot Size20,097sq ft Built2006 On Site15days
This quality home custom built by Cahill is a masterpiece! Just under 7,000 sq ft of living space and a total of 9,730 sq ft including air conditioned 3 car garage and lanai... more
This quality home custom built by Cahill is a masterpiece! Just under 7,000 sq ft of living space and a total of 9,730 sq ft including air conditioned 3 car garage and lanai with summer kitchen. Finely crafted with top of the line finishes including tray ceilings, beamed ceilings, crown molding, 8' cypress doors, Anderson thermo windows, automatic blinds, hand tumbled marble, light cream travertine stone and walnut wood floors. 2 stair cases, Library with custom built-ins, State of the art Audio Theater room with wet bar and automatic projector screen and blinds.A stunning first floor Master Suite with hand painted ceiling, morning kitchen and enormous custom closets. Gourmet Kitchen with arched brick ceiling is a Chef's paradise featuring granite counters, two Sub Zero refrigerators, Wolf oven and gas cooktop, Miele steamer oven, warming drawer, and coffee system, and U-line wine cooler.Custom Walkin pantry with loads of shelving. Kitchen opens to large Family Room with Fireplace and stunning custom built salt water aquarium which overlooks terrace, pool, and heated Jacuzzi with privacy wall. Well equipped summer kitchen with cozy fireplace, ice maker, and GE Monogram gas grill. Far too many impressive features to mention in this palatial home. Enjoy all the Fantastic amenities of the Windsong Community including water access to Winter Park chain of lakes, clubhouse with outside summer kitchen and swimming pool overlooking the lake. boating kayaking, playground in pristine condition. A Rated Schools. less
Listing Provided Courtesy of Grace Realty, Inc.
Popularity
$165,000
$611/mo
Monthly Payment:
$611
Principal & Interest:
$611
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $33,000 down)
Winter Park, FL 32792
Orange County School District
4bed 2bath 1,535sq ft $107 / sq ft SFR
Lot Size7,474sq ft Built1981 On Site15days
Short sale.4 bedroom, 2 bath home screened back porch with a shaded back yard located near convenient to. Ucf, full sail, 417 & shoping . Located in the winter park schoo district.
Short sale.4 bedroom, 2 bath home screened back porch with a shaded back yard located near convenient to. Ucf, full sail, 417 & shoping . Located in the winter park schoo district. less
Listing Provided Courtesy of Weichert Realtors Hallmark Pro
Popularity
$1,595,000
$6,130/mo
Monthly Payment:
$6,130
Principal & Interest:
$5,909
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $319,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 5,650sq ft $282 / sq ft SFR
Lot Size12,097sq ft Built2006 On Site15days
Beautiful and timeless windsong home. A one of a kind custom cahill built home. Large but warm and inviting 6 bedroom home including an inlaw suite with a mini kitchen and... more
Beautiful and timeless windsong home. A one of a kind custom cahill built home. Large but warm and inviting 6 bedroom home including an inlaw suite with a mini kitchen and separate entrance. This home is near 6000 square feet when including the third floor air conditioned attic space that was once used as a media room. (not included in listing square footage). This home has every amenity imaginable. Top of the line features include mahogany door, travertine and wood flooring, custom hearth cabinets around 3 fireplaces, plantation shutters, custom glass work, beamed ceilings and surround sound throughout the house. A very beautiful master suite is situated on the first floor with amazing ceiling work detail and a spa like master bath and an outdoor shower and retreat with a private secluded jacuzzi. Also on the first floor is a large bright office and a guest bedroom. Upstairs there are 3 large bedrooms and a huge game and family room. Beautiful back porch for entertaining around the tropically landscaped pool. This home is truely one of a kind. less
Listing Provided Courtesy of Fannie Hillman & Associates
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
3bed 2bath 2,472sq ft $202 / sq ft SFR
Lot Size13,000sq ft Built1947 On Site15days
*Click the Virtual Tour link to walk through this home in 3D!* Orwin Manor STUNNER. This spacious 3 bed, 2 bath home has the upgrades and amenities you have been asking for.... more
*Click the Virtual Tour link to walk through this home in 3D!* Orwin Manor STUNNER. This spacious 3 bed, 2 bath home has the upgrades and amenities you have been asking for. Almost everything was renovated within the last 2 years. The first thing that will strike you is the incredibly OPEN FLOOR PLAN. The kitchen is remarkable, with granite countertops, double built-in ovens, stainless appliances, and ample counter space. All three bedrooms are HUGE by downtown standards. The master bath looks like a spa, with garden tub, separate open shower, and plentiful built-in cabinetry. The very large screened lanai overlooks the ENORMOUS backyard, with wooden deck, paver area and plenty of open grass. Surround sound speakers throughout most of the house. Two-car garage. Double lot. New AC units. Newly insulated attic. Tucked away in an ideal part of Orwin Manor, away from high-traffic areas. 32789 zip code. Most furniture is negotiable. less
Listing Provided Courtesy of Uown Real Estate
Popularity
$75,500
$279/mo
Monthly Payment:
$279
Principal & Interest:
$279
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $15,100 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 1,018sq ft $74 / sq ft CND
Lot Size4,228sq ft Built1984 On Site16days
Quick closing on this adorable Freshly painted large 2 bedroom/2 full bath condo that features large open floor plan, ceramic tile flooring in the entry, kitchen and baths,... more
Quick closing on this adorable Freshly painted large 2 bedroom/2 full bath condo that features large open floor plan, ceramic tile flooring in the entry, kitchen and baths, Brand New Laminate Wood Floors that will knock your socks off! Updated kitchen appliances including a washer and dryer, both bathrooms renovated and nicely decorated, shaded relaxing screened patio with a beautiful view of mature landscaping. Master suite features a walk-in master closets! Newer outside A/C. Whether you are looking for a primary residence, a 2nd home, or an investment property, Parkview Village is where you want to be! Fabulous quiet condominium community offers the ultimate in convenient living with a lovely swimming pool, in-ground spa, playground, community clubhouse and a car wash area. Just across the street from Full Sail University, close proximity to UCF, Rollins and Valencia, Restaurants and major highways and shopping!! Priced to sell fast. less
Listing Provided Courtesy of Easy Street Realty Florida,inc
Popularity
$265,000
$981/mo
Monthly Payment:
$981
Principal & Interest:
$981
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $53,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,903sq ft $139 / sq ft SFR
Lot Size9,009sq ft Built1960 On Site16days
One of Tanglewood’s most picturesque streets. Lush landscaping and great curb side appeal! Remodeled Winter Park home featuring huge chef’s kitchen with large... more
One of Tanglewood’s most picturesque streets. Lush landscaping and great curb side appeal! Remodeled Winter Park home featuring huge chef’s kitchen with large eat-in island, Caesar stone countertops and wood and travertine floors. Cook with gas and stainless steel appliances. Beautiful bay window in front of the house and living room lets in tons of light. Open floor plan with many windows. Enclosed Florida room gives additional living space. Open up French doors and it is great flow for entertaining. Adjoining expansive covered paved outside patio. Still lots of yard space for pool, sports, or for pets. Oversized master bedroom with sitting area. Large walk-in master closet. Completely remodeled travertine bathrooms. Hydro tub in bathroom. Nicely sized bedrooms with wood floors. New roof in 2004, brand new AC, new plumbing in bathrooms, energy saving windows, gutters, sophisticated security system. Lots of fans to keep home cool. Must see this home! Lot 77x117. Convenient to Park Avenue, shopping, Whole Foods, Publix and public, private and parochial schools. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$205,000
$798/mo
Monthly Payment:
$798
Principal & Interest:
$759
HOA Dues:
$39
(Based on a 30 year fixed loan at 3.75% with $41,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,307sq ft $157 / sq ft SFR
Lot Size9,112sq ft Built1986 On Site16days
This pool home shows like a model home! Come see this beautifully well kept 1 story single family pool home in desirable Winter Park. Access to Lake Florence and Tennis courts!... more
This pool home shows like a model home! Come see this beautifully well kept 1 story single family pool home in desirable Winter Park. Access to Lake Florence and Tennis courts! The rear patio is huge, fenced and the sparkling pool creates the perfect oasis. Enjoy your beautiful Florida days and nights in the great patio space. Interior features gorgeous tile and high grade wood laminate floors, convenient eat-in kitchen with stainless steel appliances and so much more. Large master bedroom with a walk in closet and a master bath with an oversized shower! Get creative with the awesome atrium space! Open floor plan lends itself to any accommodation. Schedule a showing today as this unique opportunity will not last very long. less
Listing Provided Courtesy of Ecos Realty Llc
Popularity
$239,900
$888/mo
Monthly Payment:
$888
Principal & Interest:
$888
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $47,980 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,684sq ft $142 / sq ft SFR
Lot Size15,697sq ft Built1960 On Site16days
Excellent location for your buyers to customize and make this home their own. Large acreage of the lot and central location for enjoying all the best that Winter Park has to... more
Excellent location for your buyers to customize and make this home their own. Large acreage of the lot and central location for enjoying all the best that Winter Park has to offer. Buyers to pay Doc Stamps on the Deed. *Investor offers will NOT be entertained until 20 days after listing date. This property is eligible under the Freddie Mac First Look initiative through 10/29/2014. less
Listing Provided Courtesy of Millenium Realty Group
Popularity
$575,000
$2,130/mo
Monthly Payment:
$2,130
Principal & Interest:
$2,130
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $115,000 down)
Winter Park, FL 32789
4bed 3bath 2,579sq ft $223 / sq ft SFR
Lot Size6,750sq ft Built2014 On Site16days
Brand new construction! To be completed within 14 days. Wonderful "orwin manor area". this contemporary style home features: 10'ceilings throughout,wood... more
Brand new construction! To be completed within 14 days. Wonderful "orwin manor area". this contemporary style home features: 10'ceilings throughout,wood floors, quartz counter tops, 8' doors, gas fireplace,range, 2 efficient on-demand tankless gas water heaters, stainless appliances, crown molding, architectural shingle roof, upgraded tile, upgraded lighting and plumbing fixtures and an all glass/aluminum garage door. enjoy entertaining with the open floor plan featuring designer kitchen with sit down island seating and dinning nook, formal dinning room and a spacious family room with a natural gas fireplace looking out to a 20 x 12 covered lanai. First floor master bedroom with his and her closets, separate shower with rain and wall plumbing fixtures and floating double vanity with granite counter tops. You will love the material selections in this home. be the first to see this home to make it your own. less
Listing Provided Courtesy of Classic Homes
Popularity
$275,000
$1,018/mo
Monthly Payment:
$1,018
Principal & Interest:
$1,018
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $55,000 down)
Winter Park, FL 32792
Orange County School District
3bed 3bath 2,087sq ft $132 / sq ft SFR
Lot Size18,315sq ft Built1959 On Site16days
Open Sat Oct 25, 1pm-4pm
Completely Remodeled (2008) Home in sought after Winter Park Estates. New AC and AC Ducts throughout the Entire Home, New Roof and R19 Insulation. New Kitchen Cabinets with Self... more
Completely Remodeled (2008) Home in sought after Winter Park Estates. New AC and AC Ducts throughout the Entire Home, New Roof and R19 Insulation. New Kitchen Cabinets with Self Closing Drawers and Granite Countertops. Beautiful Vaulted Cypress Ceiling in Family Room with a Stunning Built-In Entertainment Center (72 in TV Stays). All New Doors, Trim, Baseboards, Double Pane French Doors, Fiberglass Front Door and Crown Molding throughout. Tile in all Living Areas, Red Wood Flooring in All Bedrooms and Office. Both Showers were Completed with Travertine. Granite Countertops in All Bathrooms and Laundry Room. Outdoor Living: Large 19 x 40 Covered Patio with Pavers. All Good Rated Schools and Just minutes to Shopping and Restaurants! less
Listing Provided Courtesy of Keller Williams Classic Realty
Popularity
$69,900
$483/mo
Monthly Payment:
$483
Principal & Interest:
$258
HOA Dues:
$225
(Based on a 30 year fixed loan at 3.75% with $13,980 down)
Winter Park, FL 32792
2bed 3bath 1,031sq ft $68 / sq ft TWN
Lot Size31,698sq ft Built1983 On Site17days
This 2 bedroom townhome offers private bathrooms in each bedroom, laminate flooring in the living areas and on the stairs as well as ceramic tile flooring in the kitchen and on... more
This 2 bedroom townhome offers private bathrooms in each bedroom, laminate flooring in the living areas and on the stairs as well as ceramic tile flooring in the kitchen and on the private, fenced back patio. Add your own touches and finishes and make this unit your own. Located in the established Goldenrod Road area of East Orlando, this unit provides easy access to shopping, dining, major access roads and schools. Relax and enjoy the community pool and playground as well. This is a Fannie Mae HomePath property. less
Listing Provided Courtesy of C21/oviedo Realty
Popularity
$395,000
$1,463/mo
Monthly Payment:
$1,463
Principal & Interest:
$1,463
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $79,000 down)
Winter Park, FL 32792
Orange County School District
5bed 3bath 2,600sq ft $152 / sq ft SFR
Lot Size11,183sq ft Built1957 On Site17days
Gorgeous, completely renovated 5 bedroom 3 full bath home. Rarely available 3 blocks from Winter Park High School. Minutes to Cady Way Park. All new roof, electric, plumbing,... more
Gorgeous, completely renovated 5 bedroom 3 full bath home. Rarely available 3 blocks from Winter Park High School. Minutes to Cady Way Park. All new roof, electric, plumbing, floors, paint, lighting, landscaping, windows, kitchen is Victorian Creme Cabinets with Designer slide in range and bathrooms are all new and gorgeous Master shower is huge and has 2 shower heads and built in seat. Come see your dream home with your dream space. Completely open floor plan means you can have Formal Living room, Formal Dining room, Study, Office, playroom, huge family room any way you want to use it! There are also 2 Master bedrooms and an irrigation well. This is a beauty in a great neighborhood. Big homes like this, near Winter park High, come around very rarely so don't wait. less
Listing Provided Courtesy of Sand Dollar Realty Group Inc
Popularity
$850,000
$3,149/mo
Monthly Payment:
$3,149
Principal & Interest:
$3,149
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $170,000 down)
Winter Park, FL 32789
Virginia Heights Orange County School District
3bed 3bath 3,430sq ft $248 / sq ft SFR
Lot Size8,385sq ft Built2015 On Site18days
Pre-construction. Stunning WayCool Homes by Phil Kean Contemporary home. Breath-taking curb appeal. Three bedroom (plus office), three bath two-story home - brand new for you.... more
Pre-construction. Stunning WayCool Homes by Phil Kean Contemporary home. Breath-taking curb appeal. Three bedroom (plus office), three bath two-story home - brand new for you. It's not too late to choose your finishes, and meet with Phil Kean Design Group to make this home fit your needs. Phil Kean Designs is the 2013 National Custom Home Builder of the Year. less
Listing Provided Courtesy of Not Available
Popularity
$100,000
$370/mo
Monthly Payment:
$370
Principal & Interest:
$370
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $20,000 down)
Winter Park, FL 32792
Seminole County School District
2bed 1bath 925sq ft $108 / sq ft SFR
Lot Size9,499sq ft Built1954 On Site18days
This house wants you! Bring your designer talents & cutify this sweet little winter park starter! This one has good bones and a huge shady back yard, with tons of room for... more
This house wants you! Bring your designer talents & cutify this sweet little winter park starter! This one has good bones and a huge shady back yard, with tons of room for anything you can imagine - add a pool, a green house, a studio, a 2nd story or an entire new wing! Mostly original, with 2 bedrooms/1 bath, some hardwood floors & inside laundry room. Great location within 1/4 mile of major shopping & 1/2 mile from nearby well-rated winter park schools, restaurants, lakes & parks. Less than 4 miles from full sail university & rollins college, 11 miles from university of central florida. Bring your imagination & make this cutie shine! This is a fannie mae homepath property. All information recorded in the mls is intended to be accurate but cannot be guaranteed, buyer advised to verify. less
Listing Provided Courtesy of Profitable Properties
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
1.941.487.1400
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The information being provided by Mid Florida Regional MLS 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 MLS. 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 MLS. 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 MLS 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 2014 Mid Florida Regional MLS. All rights reserved.

Data last updated: Friday, October 24, 2014 at 2:12 PM