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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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$895,000
$3,315/mo
Monthly Payment:
$3,315
Principal & Interest:
$3,315
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $179,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size20,387sq ft BuiltN/A On Site4days
Fantastic opportunity to build a new dream home at this very charming site. The house is being sold "AS-IS" and WHERE IS. Rare opportunity to find an over sized lot in the City... more
Fantastic opportunity to build a new dream home at this very charming site. The house is being sold "AS-IS" and WHERE IS. Rare opportunity to find an over sized lot in the City of Winter Park. This is for the buyer who wants seclusion and privacy. The value is in the land! Sought after Winter Park schools: Lakemont Elementary, Maitland Middle and Winter Park High School. Enjoy all of the Winter Park amenities and the best Metro Orlando has to offer. This is definitely Central Florida's gem - Winter Park. A property with old Florida charm. You can bring your own builder for this site without any HOA fees or CDC fees. less
Listing Provided Courtesy of City Realty
Popularity
Your search results are current and complete. Learn more
$189,900
$703/mo
Monthly Payment:
$703
Principal & Interest:
$703
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $37,980 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
3bed 2bath 1,278sq ft $149 / sq ft SFR
Lot Size7,700sq ft Built1955 On Site4days
Not a short sale or bank owned. Immediate response. Charming renovated ranch in desirable winter park.Split floor plan. Beautiful laminate flooring throughout common areas with... more
Not a short sale or bank owned. Immediate response. Charming renovated ranch in desirable winter park.Split floor plan. Beautiful laminate flooring throughout common areas with gorgeous tile in baths. Kitchen is showroom quality featuring carrara marble and stainless steel appliances. New windows and fresh paint complete this home. Florida room overlooks large fenced back yard. Too much to lst. Must see. Wont last. Move in ready less
Listing Provided Courtesy of South Realty, Inc
Popularity
$114,900
$425/mo
Monthly Payment:
$425
Principal & Interest:
$425
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $22,980 down)
Winter Park, FL 32792
2bed 2bath 1,219sq ft $94 / sq ft CND
Lot Size19.0acre Built1970 On Site4days
Best kept secret in Winter Park, with a country like setting, and city convenience to everything! Located in the desirable Four Season's condo's in the very popular 2 Bedroom... more
Best kept secret in Winter Park, with a country like setting, and city convenience to everything! Located in the desirable Four Season's condo's in the very popular 2 Bedroom 1.5 bath Townhouse. You will love all the amenities this complex has to offer which includes, 3 pools, clubhouse, tennis court, shuffleboard, car wash area. Beautiful grounds with resort like living with Cady Way Trails in the rear of complex, shopping, restaurants and banks just across the street, minutes to Park Ave, hospitals and more! The HOA includes water, sewer, garbage, lawn maint. building ext, pest control, on site management & use of all amenities. Large split plan bedrooms upstairs, 1 bath with large closets, kitchen, dining area & sunken living room with half bath downstairs. Enjoy the fall evenings relaxing in your private fenced 16x16 patio and just steps to the laundry area, pet friendly complex. Newer Windows and AC/Heating unit replaced in 2010. Home needs some remodeling and being sold "AS-IS". THIS HOME WILL NOT LAST LONG AND IS PRICED TO SELL!!....HURRY!! less
Listing Provided Courtesy of Weichert Realtors Hallmark Pr
Popularity
$89,900
$405/mo
Monthly Payment:
$405
Principal & Interest:
$333
HOA Dues:
$72
(Based on a 30 year fixed loan at 3.75% with $17,980 down)
Winter Park, FL 32792
Seminole County School District
2bed 2bath 1,020sq ft $88 / sq ft TWN
Lot Size2,907sq ft Built1979 On Site4days
Wow! Don't miss this exquisitely maintained townhome in a desirable Winter Park location. This exceptional updated and move-in ready home features vaulted ceilings, a screened... more
Wow! Don't miss this exquisitely maintained townhome in a desirable Winter Park location. This exceptional updated and move-in ready home features vaulted ceilings, a screened in covered patio, a private fenced paver back yard and is zoned for top rated schools with extremely low HOA dues. The kitchen and bathrooms have just been tastefully updated in addition to the brand new tankless hot water heater, the entire air conditioning system has recently been replaced making this home extremely energy efficient for low electric bills. This community offers 3 pools, shuffleboard courts, tennis courts, and access to the clubhouse for parties and events in addition to lawn maintenance and is located close to everything. Easy access to UCF/FullSail/VCC/Research Park/Downtown Winter Park and Downtown Orlando. The community is also gated on the south end of the complex for immediate access to SR 436 with no through traffic. This home really has it all. less
Listing Provided Courtesy of Keller Williams Heritage Rlty
Popularity
$129,900
$481/mo
Monthly Payment:
$481
Principal & Interest:
$481
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $25,980 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 1,986sq ft $65 / sq ft SFR
Lot Size8,139sq ft Built1958 On Site5days
Beautiful 3 bedroom home with a large lot located at the end of a street in Winter Park, you will have no through traffic. This home has an open floor plan with a large family... more
Beautiful 3 bedroom home with a large lot located at the end of a street in Winter Park, you will have no through traffic. This home has an open floor plan with a large family room and plenty of room to grow. Inside laundry room, large kitchen that overlooks a large backyard with plenty of room to put that pool you have always dreamed of. Home will not last long, don't let this one get away. This is a Fannie Mae Homepath property. The first 20 days are for owner occupants only. less
Listing Provided Courtesy of Exit Realty Central
Popularity
$72,900
$508/mo
Monthly Payment:
$508
Principal & Interest:
$270
HOA Dues:
$238
(Based on a 30 year fixed loan at 3.75% with $14,580 down)
Winter Park, FL 32792
2bed 2bath 840sq ft $87 / sq ft CND
Lot Size9,439sq ft Built1990 On Site5days
This Nice and clean Condo is rented and kept in a good condition. Community is Centrally located next to all Shopping and Restaurants, minutes away from" University of Central... more
This Nice and clean Condo is rented and kept in a good condition. Community is Centrally located next to all Shopping and Restaurants, minutes away from" University of Central Florida" (UCF), "Valencia College" and "Full Sail University". This is not REO Or Short sale. Quick sale, Investors dreams, Won't last long!!! less
Listing Provided Courtesy of Bristol Real Estate, Inc.
Popularity
$189,000
$703/mo
Monthly Payment:
$703
Principal & Interest:
$700
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.75% with $37,800 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
4bed 2bath 1,773sq ft $107 / sq ft SFR
Lot Size14,341sq ft Built1968 On Site5days
Quiet Cul-De-Sac is the perfect location for this .33 acre lot!! 4 Bedroom 2 bath home offers laminate floors & granite kitchen countertops. Light & bright... more
Quiet Cul-De-Sac is the perfect location for this .33 acre lot!! 4 Bedroom 2 bath home offers laminate floors & granite kitchen countertops. Light & bright split bedroom floor plan with formal living room & large kitchen opens to eat-in kitchen/dining room and oversized family room! Enjoy the massive, fenced backyard with sparkling pool from your friendly screened patio. Roof less than 2 years old & updated AC!! Welcome Home!! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$129,500
$479/mo
Monthly Payment:
$479
Principal & Interest:
$479
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $25,900 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
3bed 2bath 1,356sq ft $96 / sq ft SFR
Lot Size9,096sq ft Built1960 On Site5days
Great 3 bedroom 2 bathroom POOL home in the Eastbrook subdivision in Winter Park. Open floor plan with ceramic tile and recently updated bathrooms. Screened-in back porch... more
Great 3 bedroom 2 bathroom POOL home in the Eastbrook subdivision in Winter Park. Open floor plan with ceramic tile and recently updated bathrooms. Screened-in back porch overlooks a huge pool and fenced-in yard! This is a great neighborhood located in a good school district, near major bus routes, restaurants and schools. This is a Fannie Mae Homepath property. less
Listing Provided Courtesy of Smith Realty Inc
Popularity
$254,500
$964/mo
Monthly Payment:
$964
Principal & Interest:
$942
HOA Dues:
$22
(Based on a 30 year fixed loan at 3.75% with $50,900 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,819sq ft $140 / sq ft SFR
Lot Size6,883sq ft Built1989 On Site6days
Open Sun Oct 26, 11:30am-4pm
One of a kind home has been completely renovated with top notch materials. Owner is a professional interior designer; she spent over $110,000 over 9 months for renovations. Open... more
One of a kind home has been completely renovated with top notch materials. Owner is a professional interior designer; she spent over $110,000 over 9 months for renovations. Open the entry french doors reveals a living room that is magazine worthy, 24x24 black ceramic tiles contrasts hand laid natural stone wall, Martin Logan ceiling speakers. The modern kitchen features quartz counter tops, brick backdrop, German made cabinets, sleek appliances, glass cook top, built in wall oven, stainless exterior venting range hood, recessed lighting. The office area has solid bamboo floors & stone covered fire place. The home has volume ceilings through out, and many big windows to provide plenty of light. Custom window treatments for all windows will be INCLUDED. Master bedroom has bamboo floors, big windows, and two beautiful drop lights made from sea shells. Master bedroom closet features a unique glass panel closet door & custom wood organization system. The huge mater bathroom has his and her sinks, frame-less shower, tub with mosaic surround, upscale ceramic tiles throughout. The split plan home features two good sized guest bedrooms with wood floors and remote controlled fans. Upgraded insulation. All interior doors were replaced with solid core designer doors. Guest bath also features frame-less shower & two person sink. The house has been repainted with Behr Ultra Premium inside and out. Just installed new St Augustine sod. Vibrant garden in the rear is beautiful yet low maintenance. less
Listing Provided Courtesy of Sand Dollar Realty Group Inc
Popularity
$599,000
$2,219/mo
Monthly Payment:
$2,219
Principal & Interest:
$2,219
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $119,800 down)
Winter Park, FL 32789
College Park Orange County School District
5bed 4bath 3,554sq ft $169 / sq ft SFR
Lot Size7,498sq ft Built2008 On Site8days
Welcome Home to this Custom Built Masterpiece in the heart of Winter Park conveniently located next to the exclusive Dubsdread Golf course, Thornton Park, College Park &... more
Welcome Home to this Custom Built Masterpiece in the heart of Winter Park conveniently located next to the exclusive Dubsdread Golf course, Thornton Park, College Park & Downtown. You will enjoy entering your new home that boast of 26’ high ceilings & high windows allowing a spacious feeling with beautiful natural light that you will love.The intricate detail of this home is sure to impress with its, Wood and Marble flooring, Rod Iron Wine Cellar & Staircase, Baseboards, Crown Molding, Volume Ceilings, Arched Entryways, Coffered Lighted Ceilings, Granite & Stone throughout the Kitchen & Bathrooms. This well laid out floor plan offers a large Formal Dinning area, first floor Master Suite with a Garden Tub & Rain Shower & slider leading to the private courtyard, a Guest Bedroom & Bath, & utility room. As you enter the second floor you will love the large loft with its beautiful views & the potential to be a theater room, this home is wired with Cat 5 & A.V. (see Features List) featuring speakers in every room. This second floor also offers 3 bedrooms, two connected by a Jack & Jill, & its own utility room.Functionality shows throughout with, Tank Less Water Heater, ISO- Insulation, Central Vacuum, Security System & Central Intercom. Enjoy opening all 3 Sliders for the fresh breeze while enjoying your Kitchen designed for a chef with Maple Cabinetry, Stainless Steel Appliances, Gas Range & Hood or just enjoying your private courtyard oasis with your Gas heated Pool and Spa, Summer Kitchen, & Gas Fireplace. less
Listing Provided Courtesy of Olde Town Brokers Inc
Popularity
$227,000
$841/mo
Monthly Payment:
$841
Principal & Interest:
$841
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $45,400 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,960sq ft $116 / sq ft SFR
Lot Size7,234sq ft Built1962 On Site8days
Winter Park POOL Home with spacious & versatile living spaces! Sought-after community located near Aloma & 436. Formal 18x12 Dining Room with fireplace and awesome new... more
Winter Park POOL Home with spacious & versatile living spaces! Sought-after community located near Aloma & 436. Formal 18x12 Dining Room with fireplace and awesome new engineered-wood floor could easily serve as Office/Family Room/4th bedroom. The light & bright Florida Room (20x14) looks out onto the private fenced backyard with stunning tropical plants around the large pool. The eat-in Kitchen features ceramic tile flooring, wood block counter-top, plenty of cabinetry space, plus pantry in hallway close-by. Over-sized Living Room (19x19) with side-entry door from carport features a wood-burning fireplace, several secret storage spaces, and beautiful ceramic tile flooring with wood-look! Ready to move in--freshly painted inside & out! Seller will provide a transferable Termite Bond and a Home Warranty with acceptable offer. less
Listing Provided Courtesy of Dave Lowe Realty, Inc.
Popularity
$939,000
$4,424/mo
Monthly Payment:
$4,424
Principal & Interest:
$3,478
HOA Dues:
$946
(Based on a 30 year fixed loan at 3.75% with $187,800 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 2,007sq ft $468 / sq ft CND
Lot Size2.8acre Built1960 On Site9days
Lake Osceola/Whispering Waters waterfront condo "STANDARD DELUXE". Remodeled in 2012 with supreme traditional taste, quality and design. The view this unit offers is second to... more
Lake Osceola/Whispering Waters waterfront condo "STANDARD DELUXE". Remodeled in 2012 with supreme traditional taste, quality and design. The view this unit offers is second to none, it is truly extraordinary and cannot be overstated - you will know it when you see it. Personal privacy in a condo community is a critical must have and you will get it in this second floor unit. No foot traffic look-ins or parking lot views here. Condo comes with secure underground parking, storage area and walk-in storage vault. Flooring includes high quality carpeting, Brazilian cherry hardwood and porcelain tile. Crown moulding, high base and cap and trim backbanding throughout. Custom built-in entertainment center/display case, china storage closet and bar area. Master features large walk-in closet with excellent storage organization. Both bathrooms were gutted and outfitted with excellent cabinetry, marble, porcelain and stone. HVAC was completely replaced in 2012. Eat-in kitchen area also excellent lake views. Condo is outfitted with variable/dimable lighting throughout. Elevator parking to front door access, secondary access to pool area and front walk-up steps. Whispering Waters is a 3-minute walk to Park Avenue and its scores of dining and retail establishments. You can, by and large, leave your car parked and still go about a day in your new downtown Winter Park lifestyle! less
Listing Provided Courtesy of Rainmaker Properties Llc
Popularity N/A
$209,900
$777/mo
Monthly Payment:
$777
Principal & Interest:
$777
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $41,980 down)
Winter Park, FL 32792
Seminole County School District
4bed 4bath 1,851sq ft $113 / sq ft SFR
Lot Size8,442sq ft Built1980 On Site9days
Wow, wow, wow!!!!. Come and see this beautiful redone property. New kitchen cabinets, new stainless steal appliances, new interior and exterior paint, inground pool, screen... more
Wow, wow, wow!!!!. Come and see this beautiful redone property. New kitchen cabinets, new stainless steal appliances, new interior and exterior paint, inground pool, screen enclosure, one master bedroom with master bath, and one junior suite with junior bath. This house has 3 full baths and 1 half bath. New ceiling fans. New light fixtures. less
Listing Provided Courtesy of Florida Realty Investments
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
Goldenrod Seminole County School District
4bed 2bath 1,784sq ft $92 / sq ft SFR
Lot Size11,172sq ft Built1972 On Site9days
Bank Owned -Wow, opportunity time for those who can move quickly. Large four bedroom two bathroom single family pool home located on a 0.26 acre fenced corner lot me within... more
Bank Owned -Wow, opportunity time for those who can move quickly. Large four bedroom two bathroom single family pool home located on a 0.26 acre fenced corner lot me within Winter Park's Wrenwood community. This 1,784 sq-ft family home just needs some sweat equity to make it your dream home. The floor plan has open living and family rooms with wood floors and a spacious tiled kitchen with a breakfast bar, plenty of cabinet space and a closet style pantry. The split plan has the master suite to the right and the other three bedrooms to the left. Two bedrooms have wood flooring and two are carpeted. The master suite features a 14x14 bedroom, tons of closet space and a bathroom with dual sinks and a shower stall that needs an update. There is French door access onto the large covered, screened rear porch and the secluded fenced back yard that has a large open wooden deck to sunbathe and a large swimming pool. The exterior has lush tropical landscaping. The location provides access to the sought after Seminole County school district and provides easy access to shopping, restaurants and the major road networks. Don't delay. less
Listing Provided Courtesy of Connect Realty.com Inc
Popularity
$900,000
$3,334/mo
Monthly Payment:
$3,334
Principal & Interest:
$3,334
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $180,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 3,060sq ft $294 / sq ft SFR
Lot Size6,534sq ft Built2015 On Site9days
New Construction, Executive level home on Hamilton Place Ct. 12 foot ceilings throughout first floor give this home a very open and inviting feel. Three bedrooms and three full... more
New Construction, Executive level home on Hamilton Place Ct. 12 foot ceilings throughout first floor give this home a very open and inviting feel. Three bedrooms and three full baths to include a master on first floor and second floor. High end finishes throughout, including wood floors, crown molding, granite and high efficiency windows and doors. less
Listing Provided Courtesy of Coldwell Banker Residential Re
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.

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Data last updated: Friday, October 24, 2014 at 8:29 PM