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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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$589,900
$2,218/mo
Monthly Payment:
$2,218
Principal & Interest:
$2,185
HOA Dues:
$33
(Based on a 30 year fixed loan at 3.75% with $117,980 down)
Winter Park, FL 32789
Orange County School District
4bed 2bath 3,092sq ft $191 / sq ft SFR
Lot Size16,281sq ft Built1980 On Site28days
Located on cul de sac in beautiful Waterbridge subdivision next to Windsong easement. Unusually spacious and private backyard with large, open, rectangular, in-ground pool and... more
Located on cul de sac in beautiful Waterbridge subdivision next to Windsong easement. Unusually spacious and private backyard with large, open, rectangular, in-ground pool and large backyard. 9 rooms have pool view. Schools: Brookshire, Glenridge Middle, WP HS. Master BR suite includes study and double walk-in closets. Master bath includes extra vanity/dressing area. Cathedral ceiling in living and family rooms. Ceramic tile in foyer, and family room as well as kitchen / breakfast room. less
Listing Provided Courtesy of The Sheridan Network.com
Popularity
Your search results are current and complete. Learn more
$2,500,000
$9,262/mo
Monthly Payment:
$9,262
Principal & Interest:
$9,262
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $500,000 down)
Winter Park, FL 32789
Orange County School District
4bed 6bath 5,194sq ft $481 / sq ft SFR
Lot Size24,227sq ft Built2009 On Site28days
A rare find dream home in an absolutely great location. Impeccable craftsmanship, luxurious comfort, privacy and unsurpassed elegancy is what makes this home perfect for a... more
A rare find dream home in an absolutely great location. Impeccable craftsmanship, luxurious comfort, privacy and unsurpassed elegancy is what makes this home perfect for a family. This rare find Rustic-Italian Tuscany Style home includes/ features a grand entry with a breathtaking view of the lake. Beautiful rounded staircase leading to second floor suites. Gourmet kitchen with two dish washers, professional chef's stove, huge hidden pantry with additional two refrigerators, with beautiful traditional style cabinets and granite counter tops. Loaded with countless details from tray ceiling, niches, hardwood floors, travertine, granite, wood trim, beams, and entertainment centers. Owner Suite on the main floor and second master suite both include Jacuzzi, built in closets, and a private balcony on the second floor suite. Second floor features family room with built in bar area, and additional laundry room. Numerous Elegant Architectural Details include: 4 private Balconies, 2 Covered Patios with Summer-kitchen and Gas fireplace, Salt Water Pool/Spa, and steam room. Private covered boat dock that includes boat and jet ski lift. Enjoy fantastic panoramic views of ski - Lake Killarney and breathtaking sunset views from almost every room in your house. Conveniently located to Winter Park Village Plaza, Park Avenue, Farmers Market, Rollins, Winter Park Country Club, I-4, Downtown Orlando. less
Listing Provided Courtesy of Re/max Select
Popularity
$310,000
$1,343/mo
Monthly Payment:
$1,343
Principal & Interest:
$1,148
HOA Dues:
$195
(Based on a 30 year fixed loan at 3.75% with $62,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,599sq ft $194 / sq ft TWN
Lot Size2,030sq ft Built2006 On Site28days
Welcome home to this move-in ready, 3 bedroom end unit townhouse in the desirable community of townhomes at harper place in winter park! A light and bright open floor plan that... more
Welcome home to this move-in ready, 3 bedroom end unit townhouse in the desirable community of townhomes at harper place in winter park! A light and bright open floor plan that features gorgeous cherry hardwood throughout the downstairs, a gourmet style eat-in kitchen with granite counter tops, cherry cabinets, stainless appliances with gas range, and built-in wine refrigerator with custom made hutch! Enjoy watching the sunrise from the second story balcony of the master suite or entertaining friends in the evening on your private fenced and tiled patio courtyard. Extras include an attached 2 car garage, crown molding, blinds throughout, indoor laundry, dual sinks and walk-in closet in the master and many more! The community is conveniently located just a short distance from the amazing shops and restaurants of downtown winter park, the florida hospital complex and downtown orlando. Come enjoy low maintenance living and make your appointment today! less
Listing Provided Courtesy of All Real Estate & Investments
Popularity
$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
Orange County School District
4bed 3bath 1,800sq ft $158 / sq ft SFR
Lot Size10,357sq ft Built1964 On Site28days
Beautiful Pool home in one of Winter Park's most popular neighborhoods! This house has it all, 4 bedrooms, 3 baths and a 2 car garage. The 3rd bath is a convenient pool bath.... more
Beautiful Pool home in one of Winter Park's most popular neighborhoods! This house has it all, 4 bedrooms, 3 baths and a 2 car garage. The 3rd bath is a convenient pool bath. Big storage shed/workshop and it's an easy walk to the elementary school. It's on a cul-de-sac and has a big yard. You'll love saving money every month with the solar powered hot water. This is the one you've been waiting for. less
Listing Provided Courtesy of Sand Dollar Realty Group Inc
Popularity
$254,000
$944/mo
Monthly Payment:
$944
Principal & Interest:
$941
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.75% with $50,800 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,685sq ft $151 / sq ft SFR
Lot Size8,634sq ft Built1966 On Site28days
Well maintained 3 bedroom 2 bath home in Winter Park Pines. Nice floor plan with separate formal living room, formal dining room. The kitchen and family room look out over the... more
Well maintained 3 bedroom 2 bath home in Winter Park Pines. Nice floor plan with separate formal living room, formal dining room. The kitchen and family room look out over the 24x12 screened in porch and back yard. The kitchen has a pass-through window to the porch. Large inside laundry room off of the kitchen. Gas hot water heater (bottled gas) The back yard offers lots of shade with all of the trees. The roof is approx 2 years old and the ac is 3 years old. It appears that there is Terrazzo under the existing flooring. The Winter Pines Golf course is located at the end of Ranger Blvd. Cady way trail for walking and biking is located just a few steps away. Great Winter Park Schools. Just minutes away from Publix and Whole Foods for groceries and Starbucks. Very convenient to shopping and dining. Walking distance to bus service. Easy access to major highways and the airport. less
Listing Provided Courtesy of Re/max 200 Realty
Popularity N/A
$2,400,000
$8,891/mo
Monthly Payment:
$8,891
Principal & Interest:
$8,891
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $480,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 5,706sq ft $421 / sq ft SFR
Lot Size23,958sq ft Built1999 On Site29days
Located on one of Central Florida's most sought after streets---PARK AVE. Timeless classic elegance best describes this beautiful two story brick estate. Built with meticulous... more
Located on one of Central Florida's most sought after streets---PARK AVE. Timeless classic elegance best describes this beautiful two story brick estate. Built with meticulous detail and classic finishes such as hardwood floors, extensive ceiling details, leaded glass, detailed gas fireplaces, and custom built-ins in almost every room. The grand foyer welcomes guests with a graceful sweeping staircase and both formal living and dining rooms. The secluded master suite occupies the left wing of the home on the first floor and boasts a fireplace, luxurious master bath, dressing room, and a surprise hidden coffee bar. The kitchens oversize island, breakfast nook and family room all flow together for casual family time. Large French doors open to the covered lanai featuring a summer kitchen and bar area for entertaining poolside in a very private outdoor setting. Just off the kitchen is a spacious butler's pantry and wine closet. Head down the hallway to another large self-contained suite. This can serve as an in-law suite, billiard room, or executive home office. Upstairs you will find oversized bedrooms with private baths, large walk in closets, and access to the second story open-air balconies. There is a second set of stairs that offers direct access to the kitchen and family room. Bring the cars and toys-- this home has a large motor court with 4-car garages and a private gated side entry. This is a luxury home that will appeal to all generations for years to come. less
Listing Provided Courtesy of Sand Dollar Realty Group Inc
Popularity
$1,099,000
$4,071/mo
Monthly Payment:
$4,071
Principal & Interest:
$4,071
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $219,800 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 3,901sq ft $282 / sq ft SFR
Lot Size11,409sq ft Built1949 On Site29days
Combine a much desired Winter Park neighborhood and Benchmark Building Inc. and you'll find this beautifully constructed Mediterranean-Modern home. Built with attention to... more
Combine a much desired Winter Park neighborhood and Benchmark Building Inc. and you'll find this beautifully constructed Mediterranean-Modern home. Built with attention to detail with the very best quality and craftsmanship to include: travertine and white washed oak wood flooring, Mohawk designer carpeting in bedrooms, Venetian plaster, Smart House System with iPad controls, glass stair railing, solid walnut wooden breakfast bar, quartzite/carerra/travertine countertops, Grohe faucets, custom kitchen with pullout and swivel shelving, hidden pantry, Thermador Gas Appliances, 42" refrigerator, designer lighting throughout, high efficiency AC, Pella windows, two tank-less gas water heaters, fiberglass french doors, and pre wired for video surveillance. Outdoor features a private courtyard with linear fireplace, gas grill, two story lanai/balcony with chisel edge travertine flooring and rear yard is an ideal location for future pool. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$249,900
$925/mo
Monthly Payment:
$925
Principal & Interest:
$925
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $49,980 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,669sq ft $150 / sq ft SFR
Lot Size8,400sq ft Built1973 On Site29days
Completely renovated 3 bed, 2 bath home in established winter park neighborhood! This lovely 1,669 sqft home has a nice open floor plan with large windows in the formal living... more
Completely renovated 3 bed, 2 bath home in established winter park neighborhood! This lovely 1,669 sqft home has a nice open floor plan with large windows in the formal living room letting in the natural sunlight. Ceramic tile and wood flooring, crown molding, ceiling fans and blinds throughout. Kitchen has appliances & at eat-at breakfast bar that overlooks eating space in the kitchen. Formal dining room offers extra space for entertaining. Large family room has sliding glass doors that lead out to the large, fenced back yard with mature tropical landscaping. Master bedroom has a walk-in closet & master bath has a walk-in shower. Second bathroom has bathtub with shower. Other two bedrooms have nice sized closets. Indoor utility room. 2-car garage & updated windows. Brand new roof, new a/c. No hoa. Convenient to 426/aloma, 417, 50/colonial, park ave., airport, shopping and restaurants. less
Listing Provided Courtesy of Metro City Realty
Popularity
$1,299,000
$4,812/mo
Monthly Payment:
$4,812
Principal & Interest:
$4,812
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $259,800 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 3,753sq ft $346 / sq ft SFR
Lot Size13,234sq ft Built1991 On Site30days
Open Sun May 31, 12pm-3pm
Stunning 4 bedroom 4 1/2 bath home with a separate study/den that could be a 5th bedroom. This home is in a prime Via location on one of the most desirable streets in Winter... more
Stunning 4 bedroom 4 1/2 bath home with a separate study/den that could be a 5th bedroom. This home is in a prime Via location on one of the most desirable streets in Winter Park. This gorgeous home has been updated with top of the line finishes; Bamboo flooring, hardwood, marble, crown molding, plantation shutters throughout, stainless gas appliances, granite countertops and much more. The private master suite is downstairs on the 1st floor and features a very large walk in closet with organizers and large master bath. Upstairs are 3 additional bedrooms, which one can be another large master suite or bonus room. This home has lots of closets and storage throughout. New gourmet kitchen with gas and large eat in area, and family room all overlooking private fenced yard and beautiful pool with pavers and stone. Separate 2 car detached garage with 1/2 bath and summer kitchen for entertaining. Roof is 2 1/2 years, 3 A/C's (2 new), new tankless hot water heater and pool heater and more. Walk to Winter Park Racquet Club. This is a quality home with Winter Parks A+ Schools. Dommerich Elementary, Maitland Middle, and Winter High School. Come view this home today! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity N/A
$78,000
$598/mo
Monthly Payment:
$598
Principal & Interest:
$288
HOA Dues:
$310
(Based on a 30 year fixed loan at 3.75% with $15,600 down)
Winter Park, FL 32792
1bed 1bath 793sq ft $98 / sq ft CND
Lot Size19.0acre Built1970 On Site30days
First floor ....Ready to move in....This unit is open and bright...Ceramic tile in living area and carpet in the bedroom...Has great screen porch with storage closet...This unit... more
First floor ....Ready to move in....This unit is open and bright...Ceramic tile in living area and carpet in the bedroom...Has great screen porch with storage closet...This unit is ready for immediate occupancy. Pools, tennis, shuffleboard on-site. Veteran on-site management has kept four seasons one of the best maintained places in wp. Great location near grocery, restaurants and movies. Easy access to sr 436, winter park, orlando. Right in the middle of everything! less
Listing Provided Courtesy of Winter Park Land Co.
Popularity
$185,000
$685/mo
Monthly Payment:
$685
Principal & Interest:
$685
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $37,000 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,662sq ft $111 / sq ft SFR
Lot Size7,472sq ft Built1981 On Site30days
The sellers prefer to provide financing. They are willing to provide multiple options if the buyer would like to update parts of the property. This well-maintained home is... more
The sellers prefer to provide financing. They are willing to provide multiple options if the buyer would like to update parts of the property. This well-maintained home is located in Orange County Winter Park and is move-in ready! A NEW AC system was installed in 2013, and the ARCHITECTURAL SHINGLE roof is estimated to be only 6-8 years old. In 2015, a NEW HOT WATER HEATER and NEW INTERIOR PAINT were added. The main living area features 18” TILE FLOORS, CROWN MOULDING, UPDATED LIGHT FIXTURES, and a view of the lush backyard. You will find added character in the SCULPTED DOORWAYS and LIGHTED FOYER DISPLAY INSET. Popcorn ceilings have been removed! The kitchen features STAINLESS STEEL APPLIANCES, a double sink, recessed lighting, and a window over the sink. The new owner can take advantage of the GAS already piped to the home. All bedrooms have WALK IN CLOSETS and CROWN MOULDING! The master bathroom offers a shower updated with gorgeous TILE and GLASS BLOCK, an oversized mirror, and modern lighting. The backyard is completely FENCED and has mature, tropical landscaping. This school district includes Aloma Elementary, Glenridge Middle, and Winter Park High. Enjoy being just minutes from popular Park Ave, Rollins College, and the Winter Park chain of lakes. less
Listing Provided Courtesy of Keller Williams Advantage Rlty
Popularity
$85,000
$314/mo
Monthly Payment:
$314
Principal & Interest:
$314
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $17,000 down)
Winter Park, FL 32792
Orange County School District
1bed 1bath 727sq ft $117 / sq ft CND
Lot Size19.0acre Built1970 On Site30days
Rare 1-Bedroom, 1st Floor Condo OVERLOOKING THE POOL! Enjoy the best of what Winter Park has to offer at desirable Four Seasons…one of the City’s best kept... more
Rare 1-Bedroom, 1st Floor Condo OVERLOOKING THE POOL! Enjoy the best of what Winter Park has to offer at desirable Four Seasons…one of the City’s best kept secrets!. This home has been tastefully updated with a RENOVATED KITCHEN and BATH and a 3-YEAR NEW A/C SYSTEM! This well-maintained unit features a spacious Living Room, separate Kitchen & Dining Room, a spacious Bedroom and a newly screened, covered lanai to relax and unwind! This beautiful community is surrounded by trees & offers 3 swimming pools, tennis courts, 3 shuffleboard courts, a Clubhouse, Laundry facilities & a car wash area. Condo fees also include water, sewer & trash removal, ground & landscaping maintenance and pest control. This community is APPROVED for FHA & VA LOANS & is located within the Winter Park city limits and has it all…Top-Rated Winter Park schools & Convenience at an Affordable Price…located just minutes from Park Avenue, Museums, Theaters, Whole Foods, Winter Park YMCA, Rollins College, Full Sail University, Medical Centers, high end shopping & restaurants. Four Seasons is only minutes away from Cady Way Trail which will soon expand to connect with St Andrews for even more convenience! less
Listing Provided Courtesy of Keller Williams Advantage Rlty
Popularity N/A
$824,900
$3,056/mo
Monthly Payment:
$3,056
Principal & Interest:
$3,056
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $164,980 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,555sq ft $323 / sq ft SFR
Lot Size10,999sq ft Built1973 On Site31days
Charming describes this fabulous 4 bedroom, 2.1 bath, 2,555 square foot pool home located on a quiet brick street in one of "Olde" Winter Park's most desirable neighborhoods... more
Charming describes this fabulous 4 bedroom, 2.1 bath, 2,555 square foot pool home located on a quiet brick street in one of "Olde" Winter Park's most desirable neighborhoods while just a short distance away from the shops and restaurants of Park Avenue and the popular Winter Park Golf Course. High end finishes are evident the minute you walk through the front door of this extensively renovated home. Formal living and dining rooms, family room with coffered ceiling, master bedroom features a large walk-in closet (formally 4th bedroom) with custom cabinetry, Wood-Mode kitchen cabinets with granite tops, plantation shutters, Brazilian cherry hardwood flooring, saltillo tile, Pella double-pane windows, sparkling pool with diamond brite finish, fenced yard and wonderful landscaping are just a few of this home’s many fine features offering the opportunity for indoor and outdoor entertaining! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$185,000
$830/mo
Monthly Payment:
$830
Principal & Interest:
$685
HOA Dues:
$145
(Based on a 30 year fixed loan at 3.75% with $37,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 4bath 1,628sq ft $114 / sq ft TWN
Lot Size2,270sq ft Built2003 On Site31days
Move-in ready two story Townhome located in Vistas at Lake Howell a gated community, in fantastic location with Winter Park address. All bedrooms are upstairs with laundry for... more
Move-in ready two story Townhome located in Vistas at Lake Howell a gated community, in fantastic location with Winter Park address. All bedrooms are upstairs with laundry for extra convenience. Master includes large walk-in closet with double vanity in master bath! Downstairs you will find a large open living area with ½ bath, kitchen, dining area, family room and screened in porch! Storage areas include owner added areas under the stairs, in attic and in garage! less
Listing Provided Courtesy of Winter Park Land Co.
Popularity
$63,300
$234/mo
Monthly Payment:
$234
Principal & Interest:
$234
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $12,660 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 1,085sq ft $58 / sq ft CND
Lot Size5,644sq ft Built1974 On Site32days
2 bedroom 1.5 baths unit recently been updated with new carpet, paint, upgraded tile in the baths, a newer AC unit and water heater are just some of the features that make this... more
2 bedroom 1.5 baths unit recently been updated with new carpet, paint, upgraded tile in the baths, a newer AC unit and water heater are just some of the features that make this property a great deal for an investor or student. Property is walking distance to Full Sail and just a short commute to UCF and Valencia. less
Listing Provided Courtesy of Jr Kroll Realty
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
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.

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Data last updated: Wednesday, May 27, 2015 at 7:55 PM