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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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$54,900
$409/mo
Monthly Payment:
$409
Principal & Interest:
$203
HOA Dues:
$206
(Based on a 30 year fixed loan at 3.75% with $10,980 down)
Winter Park, FL 32792
Golfside Orange County School District
2bed 2bath 1,049sq ft $52 / sq ft CND
Lot SizeN/Asq ft Built1969 On Site18days
Priced and primed for renovation. 2br/2ba second floor condo in winter park. Brand new oven and fuse box. This property is elgible under the freddie mac first look initiative... more
Priced and primed for renovation. 2br/2ba second floor condo in winter park. Brand new oven and fuse box. This property is elgible under the freddie mac first look initiative through 2/16/2016. Property is being sold as-is, where is. less
Listing Provided Courtesy of ORLANDO REO PROF I INC
Popularity
Your search results are current and complete. Learn more
$485,000
$1,796/mo
Monthly Payment:
$1,796
Principal & Interest:
$1,796
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $97,000 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,784sq ft $272 / sq ft SFR
Lot Size9,327sq ft Built1940 On Site18days
Lovely, Cape Cod style Bungalow, nestled among million dollar homes and lakes in the heart of Winter Park ! This absolute charming, well maintained home boasts 1784 sq. feet of... more
Lovely, Cape Cod style Bungalow, nestled among million dollar homes and lakes in the heart of Winter Park ! This absolute charming, well maintained home boasts 1784 sq. feet of living space. Totally remodeled, designer kitchen with custom cabinetry, granite counters, and all high end appliances, including gas range, Fisher & Paykel 2 drawer dishwasher, 2 GE Profile Convection Ovens ! Picturesque living room with wood burning fireplace. From the living room French doors open up to a cheerful and inviting sunroom. Elegant formal dining room. Inside laundry and mud room. Tank less water heater for energy saving efficiency. 1 car detached garage. A private fenced backyard with lovely mature landscaping makes this a peaceful setting for relaxing and grilling out. Winter Park Schools. Very close to Park Ave and all that Winter Park has to offer. Make this home your own….start enjoying the Winter Park lifestyle that you have only dreamed of !!! less
Listing Provided Courtesy of OLDE TOWN BROKERS INC
Popularity
$1,125,000
$4,168/mo
Monthly Payment:
$4,168
Principal & Interest:
$4,168
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $225,000 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 3,672sq ft $306 / sq ft SFR
Lot Size13,241sq ft Built1999 On Site18days
Fabulous Winter Park Home in prime Location! Your first impression will be coming home to one of Winter Park’s most quaint streets. This beautiful home which is walking... more
Fabulous Winter Park Home in prime Location! Your first impression will be coming home to one of Winter Park’s most quaint streets. This beautiful home which is walking distance to Park Avenue features 5 bedrooms/4 baths plus bonus room. Great kitchen with granite countertops, SS appliances & cozy breakfast nook opens up to the spacious family room with wood burning fireplace and beautiful built-in cabinets. All rooms open to an incredible pool oasis, brick patio and private putting green. Downstairs features a beautiful master suite and secondary bedroom/bath or optional office. All flooring in the main living areas feature hardwoods. The foyer, kitchen and hallway have travertine. Upstairs you will find 3 bedrooms/2 baths and a wonderful bonus room. All of this nestled on a corner lot surrounded by beautiful mature landscaping and neighboring lakefront homes. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$699,500
$2,591/mo
Monthly Payment:
$2,591
Principal & Interest:
$2,591
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $139,900 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,444sq ft $286 / sq ft SFR
Lot Size16,848sq ft Built1971 On Site18days
This fabulous home is well-maintained & is situated on a quiet cul-de-sac in highly desirable Park North. The floor plan is perfect for entertaining or family living. Separate... more
This fabulous home is well-maintained & is situated on a quiet cul-de-sac in highly desirable Park North. The floor plan is perfect for entertaining or family living. Separate formal living room with spacious dining room. Wood burning fireplace in living room overlooking the large back yard and pool. Split bedroom plan with two rooms on the North side sharing an oversized full bathroom and the South side has the master suite. Step outside and enjoy your covered patio w/ screened LARGE pool and private yard with tall bordering landscaping. Enjoy the short walk or bike ride to Park Avenue's Restaurants, Boutiques, Central Park & the Winter Park Farmers Market. Also nearby are Winter Park's golf & racquet clubs, the local Community Center, Historic District, Winter Park's Chain of Lakes, Museums & Playgrounds. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
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 4bath 3,670sq ft $245 / sq ft SFR
Lot Size11,342sq ft Built1993 On Site18days
Guest Cottage with a tastefully renovated, upscale, pool home on a gorgeous, tree-lined brick street in desirable Winter Park. With sophisticated touches and amenities your... more
Guest Cottage with a tastefully renovated, upscale, pool home on a gorgeous, tree-lined brick street in desirable Winter Park. With sophisticated touches and amenities your family will enjoy the luxury of a resort from their own home. The Tuscan inspired home has a gourmet Chef's dream island kitchen with custom wood cabinets, top of the line GE Profile appliances, granite counter tops, and wine cooler. The beautiful custom wrought iron staircase leads upstairs to the master suite, three other bedrooms, and three full bathrooms. A fifth room may be suitable for an office or additional bedroom and connects to a full bath. Nook at the stair-top is an ideal spot for peaceful reading. In addition, the home is adorned with plantation shutters, 24" stone tile floors downstairs, rich hardwood floors upstairs, and high ceilings. Renovated guest cottage above the two-car garage is as welcoming as the main house and boasts a full bath, a full kitchen, laundry room, dining area, and comfortable sitting room. The detached two-car garage has an electric gate that conveniently accesses a spacious parking area and a very private backyard. The yard features magnificent landscaping, with custom accent lighting, a pool, flagstone deck and pool bath. This home is beautiful and perfectly located for your enjoyment of all that Winter Park has to offer. Just a short bike ride to the YMCA, Winter Park Racquet Club, Winter Park Village, Whole Foods, and all the shops and restaurants on Park Ave. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$73,500
$569/mo
Monthly Payment:
$569
Principal & Interest:
$272
HOA Dues:
$297
(Based on a 30 year fixed loan at 3.75% with $14,700 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 1,018sq ft $72 / sq ft CND
Lot Size4,228sq ft Built1984 On Site19days
Fabulous location! 2 bedroom, 2 bath, ground floor condo 1018 square feet!. Two bedrooms and two full bathrooms with an open floor plan and walk-in closet in master bedroom!... more
Fabulous location! 2 bedroom, 2 bath, ground floor condo 1018 square feet!. Two bedrooms and two full bathrooms with an open floor plan and walk-in closet in master bedroom! Includes fridge, range, microwave, washer & dryer. Relax in the resort style community pool or warm up in the hot tub under the gazebo, fenced playground, private screened patio. Conveniently located across the street from chili's restaurant & full sail school off of 436 (semoran blvd.) or a quick drive to dining, shopping, siemens, rollins college, ucf or valencia community college. Call today! less
Listing Provided Courtesy of FERDINANDSEN ENTERPRISES, INC.
Popularity
$199,900
$740/mo
Monthly Payment:
$740
Principal & Interest:
$740
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $39,980 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
3bed 2bath 1,609sq ft $124 / sq ft SFR
Lot Size12,467sq ft Built1972 On Site19days
Short Sale but not like the usual. This is a reverse mortgage. We can have it approved in a short period of time. Beautiful traditional floor plan. Formal living,... more
Short Sale but not like the usual. This is a reverse mortgage. We can have it approved in a short period of time. Beautiful traditional floor plan. Formal living, formal dining with a sliding glass door, and an eat in kitchen. The living room is a step down, and looks out over the very large, fenced, landscaped, private backyard. There is a nice dining room that has plenty of room for the big furniture, and also views the back yard. The family room is more closed with a sliding door, a beautiful, cozy fireplace with rock detailing. Great for parties, or watching the BIG GAME! Room for a huge big screen television. There is a wonderful screened lanai on the back so you can enjoy the birds and peace and quiet without those pesky bugs. The master has a lovely large closet and separate vanity from the shower and toilet area. Perfect for no humidity on the mirror. The other bedrooms are large with extra storage and just great space for family members. The home has a great over-sized garage with extra storage and utility area as well. The kitchen is compact and has lots of cabinets and space for a dinette set as well. Pass through to the dining makes this great. Wonderful schools too. Come and see this beauty today. less
Listing Provided Courtesy of KELLER WILLIAMS AT THE PARKS
Popularity
$125,000
$463/mo
Monthly Payment:
$463
Principal & Interest:
$463
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $25,000 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 1,219sq ft $103 / sq ft CND
Lot Size19.0acre Built1970 On Site20days
Very popular 2 Bedroom Townhouse in the Beautiful Four Seasons!! You will love the benfits of living here!! Beautiful large tile floors on first floor and stylish faux wood... more
Very popular 2 Bedroom Townhouse in the Beautiful Four Seasons!! You will love the benfits of living here!! Beautiful large tile floors on first floor and stylish faux wood floors on the second level. Close to Shops, Restaurants, & Great Schools. Pets are Welcome. H.O.A. Includes clubhouse, water, Sewer, Garbage Collection, 3 Pools, Lawn Maintenance, Tennis Courts, Shuffleboard, Car Wash Area, on site manager and maintenance staff. Beautiful grounds-resort like living. This Condo has large private screen in patio for those relaxing summer evening, in condo washer and dryer, parking conveniently right of the unit. THIS WILL NOT LAST LONG, BRING YOUR BUYERS, THEY WILL LOVE THIS CLEAN CONDO AT A GREAT PRICE. One year home Warranty for peace of mind. less
Listing Provided Courtesy of WINTER PARK REAL ESTATE CO LLC
Popularity
$420,000
$1,556/mo
Monthly Payment:
$1,556
Principal & Interest:
$1,556
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $84,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,932sq ft $217 / sq ft TWN
Lot Size11,000sq ft Built2014 On Site20days
Brand new home! This beautiful mediterranean style winter park town home with a traditional interior touch will make you fall in love! As you enter onto the cobblestone... more
Brand new home! This beautiful mediterranean style winter park town home with a traditional interior touch will make you fall in love! As you enter onto the cobblestone driveway, you'll immediately notice the impressive architectural details of the windows, doors, and garage doors. As you enter the home, notice the exquisite wood floors throughout the first floor in this open floor plan. As you enter the kitchen, lg energy star appliances, wood cabinets, and granite counter tops await you. Oil bronzed fixtures, crown molding, upgraded light fixtures and ceiling fans adorn this home throughout. The second floor split plan, is equally as impressive with great sized rooms, and a master bedroom with tray ceiling. The spa like master bathroom offers a masterful designed shower with therapeutic pebble stone flooring. For those energy cautious buyers, thermal insulated windows and foam insulated walls/attic will not only contribute to lower heating and cooling costs, but a quieter home. Located across from azalea lane community center for those avid tennis players, and in between pennsylvania avenue and orange avenue making access to all that's happening in downtown winter park and park avenue a breeze. Whether you interested in the nearby walking trails, lake virginia boating ramp, dining, shopping, business, or night life, you'll find it all at this location. Did we forget to mention, no hoa fees!! less
Listing Provided Courtesy of ESTATES HOMES SALES & RENTALS
Popularity
$159,900
$592/mo
Monthly Payment:
$592
Principal & Interest:
$592
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $31,980 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
4bed 2bath 1,769sq ft $90 / sq ft SFR
Lot Size8,414sq ft Built1971 On Site20days
Awaiting your imagination. Great floor plan with lots of space & potential. Home features formal living and dining rooms. Spacious family room opens to kitchen. Nice master... more
Awaiting your imagination. Great floor plan with lots of space & potential. Home features formal living and dining rooms. Spacious family room opens to kitchen. Nice master suite with private bath and walk-in closet. Three additional bedrooms with hall bath. Screened porch and nice yard. No HOA, ideal location close to major highway, restaurants, & shopping. Sold "as-is". Call today for your private showing. less
Listing Provided Courtesy of KELLER WILLIAMS WINTER PARK
Popularity
$190,000
$703/mo
Monthly Payment:
$703
Principal & Interest:
$703
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $38,000 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
4bed 2bath 1,756sq ft $108 / sq ft SFR
Lot Size8,677sq ft Built1983 On Site20days
Recently replumbed, reroofed and new A/C system add to the value of this four bedroom Winter Park home complete with formal living room, dining room and family room. French... more
Recently replumbed, reroofed and new A/C system add to the value of this four bedroom Winter Park home complete with formal living room, dining room and family room. French doors lead to the large closed in patio to extend your living area. Located on a quiet street close to Eastbrook Elementary School. Large oak trees shade the back yard to help keep the power bills in check. less
Listing Provided Courtesy of CHARLES RUTENBERG REALTY
Popularity
$1,095,000
$4,106/mo
Monthly Payment:
$4,106
Principal & Interest:
$4,056
HOA Dues:
$50
(Based on a 30 year fixed loan at 3.75% with $219,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,213sq ft $260 / sq ft SFR
Lot Size22,127sq ft Built1999 On Site20days
Custom built, five bedroom, four and one-half bath pool home in Sevilla. Beautifully designed with every thought and consideration the home boasts a very desirable 3-way split... more
Custom built, five bedroom, four and one-half bath pool home in Sevilla. Beautifully designed with every thought and consideration the home boasts a very desirable 3-way split floorplan with a downstairs master and guest suite and three upstairs bedrooms. Formal living and dining off the foyer are light and bright and complimented by wonderfully high ceilings. Located at the center of the home is the kitchen which features a bay window breakfast nook, breakfast bar, stainless steel appliances, and granite counters. Brick mantled fireplace and French doors in the Family room that lead to the covered lanai are warm and inviting and great for indoor/outdoor entertainment. Master bedroom with sitting area is spacious and comfortable and offers a master bath complete with his and her walk-in closets, double vanities, and jetted soaking tub. Set on a large, corner lot, the pool and spa are open to great sunlight exposure and yet remain private behind a fenced in property and large, mature oak trees. Minutes from Park Avenue, walk thru some of Winter Park’s charming neighborhoods to your favorite shops and restaurants. First time on the market, this stunning home won’t last long. Call and schedule your showing today. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$429,000
$1,589/mo
Monthly Payment:
$1,589
Principal & Interest:
$1,589
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $85,800 down)
Winter Park, FL 32789
Orange County School District
4bed 2bath 1,902sq ft $226 / sq ft SFR
Lot Size6,389sq ft Built1926 On Site21days
Charming and private Winter Park bungalow nestled between larger homes on quaint brick street. Lots of details within this home. Beautiful old and new hardwood floors and volume... more
Charming and private Winter Park bungalow nestled between larger homes on quaint brick street. Lots of details within this home. Beautiful old and new hardwood floors and volume ceilings with lots of light. Intricate wood work on ceilings adds to the charm.Large dining room with bay window. Cherry wood cabinets,granite counters, stainless steel appliances and Mediterranean tile in the over-sized kitchen. You will love the picture window in over the kitchen sink looking at the lush vegetation. Field stone-two-sided wood burning fireplace, family room and kitchen. The room sizes are perfect for a starter home or downsize. Two bedrooms on the first floor featuring Kahrs hardwood floors and more great ceilings. Private bathroom. Upstairs is a true master retreat including separate office that could be 4th bedroom. Master is generous and also has fireplace and gorgeous picture windows to the trees. Well-appointed master has lots of updated built-ins to show off paintings and treasures. Completely remodeled master bathroom has tons of natural light and handpicked Spanish tiles. Outside you have a clean slate with lots of lush vegetation and brick patio and fenced. Detached office guest house is a perfect get-away or terrific storage area. Some of the most recent upgrades include -new French doors. Roof replaced 2010-2011. ADT alarm system. Water heater 2014.Close to shopping, Winter Park schools, Phelps Park, Baldwin Park dog park Publix and Park Avenue. This area is a gem for running, walking, biking and more! less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$119,000
$706/mo
Monthly Payment:
$706
Principal & Interest:
$440
HOA Dues:
$266
(Based on a 30 year fixed loan at 3.75% with $23,800 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
2bed 3bath 1,236sq ft $96 / sq ft TWN
Lot Size1,500sq ft Built1985 On Site21days
Now is your chance to move into the beautiful community of Lazy Oaks in Winter Park! This two bedroom townhouse is perfect for your next home. The hardwood floors in the open... more
Now is your chance to move into the beautiful community of Lazy Oaks in Winter Park! This two bedroom townhouse is perfect for your next home. The hardwood floors in the open floor plan make it great for entertaining. The vaulted ceilings on the second floor make the bedrooms feel very spacious. Go for a stroll in the beautifully landscaped community. Call for a private showing today! less
Listing Provided Courtesy of CENTURY 21 ROO REALTY
Popularity
$72,500
$525/mo
Monthly Payment:
$525
Principal & Interest:
$268
HOA Dues:
$257
(Based on a 30 year fixed loan at 3.75% with $14,500 down)
Winter Park, FL 32792
Orange County School District
2bed 3bath 1,090sq ft $67 / sq ft CND
Lot Size10.1acre Built1974 On Site23days
This is the Townhouse locate in Excellent Schools, UCF and VCC. Wood laminate flooring thru-out the house. freshly new paint , Includes washer/dryer are stay in the house.... more
This is the Townhouse locate in Excellent Schools, UCF and VCC. Wood laminate flooring thru-out the house. freshly new paint , Includes washer/dryer are stay in the house. Community amenities include pool, tennis courts, playground and clubhouse. Easy access to major highways, SR 408, 417 and SR 436 and shopping plaza, Please come see and make offer with quick response. less
Listing Provided Courtesy of CAPITAL REALTY GROUP FLORIDA
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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Data last updated: Saturday, February 13, 2016 at 7:51 PM. Properties in listings may have been sold or may no longer be available.