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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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$2,295,000
$8,502/mo
Monthly Payment:
$8,502
Principal & Interest:
$8,502
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $459,000 down)
Winter Park, FL 32789
Orange County School District
6bed 8bath 6,943sq ft $331 / sq ft SFR
Lot Size25,880sq ft Built1999 On Site53days
Gorgeous Winter Park Estate on tree lined brick street in the heart of town. This stunning custom home has a Mediterranean flair with a beautiful pool are and a full guest... more
Gorgeous Winter Park Estate on tree lined brick street in the heart of town. This stunning custom home has a Mediterranean flair with a beautiful pool are and a full guest apartment. Five luxury suites~each with private bath and private walk in closet. The sixth bedroom is a detached suite that is finished with hard wood flooring and newly renovated private bath. There is a circular driveway with brick pavers and an exquisite stone fountain-plenty of parking. Majestic hand carved solid wood double-door which sets the tone of quality products and strong attention to detail featured throughout this luxury home. Magnificent foyer. Formal living room with cast stone columns. Exotic coral-style Travertine flooring. Venetian plaster compliments the walls. The perfect gourmet kitchen features custom cabinetry, natural gas cook top, and spacious island with cook's second sink. The large family room has wood-beam ceilings, spectacular wood burning stone fireplace, chic bar and high-tech surround sound system. State-of-the-art home theatre. Spectacular heated salt water pool and oversized spa. Excellent location with strong schools. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
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$1,365,000
$5,279/mo
Monthly Payment:
$5,279
Principal & Interest:
$5,057
HOA Dues:
$222
(Based on a 30 year fixed loan at 3.75% with $273,000 down)
Winter Park, FL 32789
Windsong Orange County School District
5bed 4bath 4,406sq ft $310 / sq ft SFR
Lot Size24,379sq ft Built2008 On Site54days
WINDSONG Custom Built Beauty on distinguished Preserve Point Drive. Secluded .5+ acre lot is the perfect setting for this 5 Bedroom PLUS Library/Study boasting 17'ceilings, 9'... more
WINDSONG Custom Built Beauty on distinguished Preserve Point Drive. Secluded .5+ acre lot is the perfect setting for this 5 Bedroom PLUS Library/Study boasting 17'ceilings, 9' doors, travertine & wide plank hardwood floors throughout the downstairs. Elegant first floor Master Suite complete with rustic wood beams, onyx tub, & his/ hers vanities and walk-in closets. Gourmet kitchen with beautiful breakfast bar & butler pantry overlooks large family room with gas fireplace. Heated, screened, saltwater pool PLUS huge backyard perfect for entertaining! Extras include: FOUR CAR GARAGE, emergency gas generator, safe room, surround sound & upstairs bonus room!! FABULOUS WINDSONG amenities include: Winter park Chain of Lakes access, FUN family pool with splash pad, PLUS a serene Community pool, clubhouse & dock on Lake Mizell! WELCOME HOME! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$49,900
$184/mo
Monthly Payment:
$184
Principal & Interest:
$184
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $9,980 down)
Winter Park, FL 32789
Orange County School District
1bed 1bath 638sq ft $78 / sq ft CND
Lot Size17,764sq ft Built1966 On Site54days
Recently Remodeled Waterfall Cove, first floor, Winter Park Condo with tile and laminate flooring, upgraded appliances, patio, and a community pool! Great location near I-4, and... more
Recently Remodeled Waterfall Cove, first floor, Winter Park Condo with tile and laminate flooring, upgraded appliances, patio, and a community pool! Great location near I-4, and Winter Park Village! Property offered for Sale 'As Is'. less
Listing Provided Courtesy of Premium Properties R.e Service
Popularity
$74,900
$349/mo
Monthly Payment:
$349
Principal & Interest:
$277
HOA Dues:
$72
(Based on a 30 year fixed loan at 3.75% with $14,980 down)
Winter Park, FL 32792
Seminole County School District
2bed 2bath 1,094sq ft $68 / sq ft TWN
Lot Size3,499sq ft Built1978 On Site54days
Back on the market! Corner lot single story townhome in winter park. Home has beautifully updated kitchen with 36 inch cabinets, granite counter tops and tiled backsplash.... more
Back on the market! Corner lot single story townhome in winter park. Home has beautifully updated kitchen with 36 inch cabinets, granite counter tops and tiled backsplash. Laminate floors and ceramic tile throughout. Travertine floor to ceiling fireplace in the family room. Glass sliders lead to brick paved fenced patio. Additional room could easily be a 3 third room. Unit located close to shopping and restaurants. Community pool and tennis courts. This is a fannie mae homepath property. Visit the homepath website for more information. less
Listing Provided Courtesy of Florida Real Estate Properties
Popularity
$1,395,000
$5,168/mo
Monthly Payment:
$5,168
Principal & Interest:
$5,168
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $279,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 3,998sq ft $349 / sq ft SFR
Lot Size14,000sq ft Built2003 On Site56days
Traditional Mediterranean with transitional design is a Winter Park masterpiece offering elegance and simplicity for the ultimate Florida lifestyle. This custom Bates Driscoll... more
Traditional Mediterranean with transitional design is a Winter Park masterpiece offering elegance and simplicity for the ultimate Florida lifestyle. This custom Bates Driscoll home was designed by architect Gary Hancock and is perfectly nestled on a quiet street aligned with canopied trees. Beautiful formal rooms welcome as you enter. The kitchen is a chef’s delight with a prep island with a gas cooktop, double built-in ovens, warming drawer, two sinks and large walk-in pantry; As well, it is wonderfully open to the family room, lanai, pool and yard. Gorgeous wood floors throughout all the living areas. Large downstairs guest bedroom with adjacent full bath. Stunning master bedroom suite offers his-and-hers’ vanities, craw foot tub, and spacious walk-in closet. Three additional bedrooms with two large baths, bonus room with balcony access and laundry room are also on the second floor. The home’s outdoor layout provides exceptional entertaining with pool, outdoor shower and immaculate grounds. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$259,000
$959/mo
Monthly Payment:
$959
Principal & Interest:
$959
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $51,800 down)
Winter Park, FL 32790
Seminole County School District
3bed 2bath 1,845sq ft $140 / sq ft SFR
Lot Size8,400sq ft Built1971 On Site56days
Fantastic pool home in Winter Woods! Desirable floor plan with over 1,800 square feet of living space, offering three bedrooms, a den, two full baths and screened patio. Ceramic... more
Fantastic pool home in Winter Woods! Desirable floor plan with over 1,800 square feet of living space, offering three bedrooms, a den, two full baths and screened patio. Ceramic tile and laminate wood flooring give the home a fresh, clean look. Kitchen has been tastefully updated with new cabinetry, solid counter-tops, newer appliances and a pass-thru window with views of the pool. Master bedroom has private bath with walk-in shower. Secondary bedrooms each have ample closet space and share a hall bath with double sinks. Full-size, indoor laundry room off the family room also has access to the attached two-car garage. Tucked away on a quiet cul-de-sac you’ll forget that this home is conveniently located to nearby shops, dining, and major highways. Call and schedule your showing today! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$269,000
$1,326/mo
Monthly Payment:
$1,326
Principal & Interest:
$996
HOA Dues:
$330
(Based on a 30 year fixed loan at 3.75% with $53,800 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,776sq ft $151 / sq ft TWN
Lot Size2,504sq ft Built1983 On Site56days
Enjoy every sunset from either of your two large second floor balconies. A brick pavered driveway leads you into this second floor 3 bedroom/ 2 bath condo located adjacent to... more
Enjoy every sunset from either of your two large second floor balconies. A brick pavered driveway leads you into this second floor 3 bedroom/ 2 bath condo located adjacent to Azalea Lane Park, just a short walk to the shops and restaurants on Park Avenue. The unit is almost 1800 SF of bright and airy space with 3 set of french doors, large rooms, a ton of closet space, indoor laundry, crown molding, fireplace, over 400 SF of balcony surface and an oversize 2-car attached garage. The large white kitchen includes an open window to the living room, plenty of cabinets and counter space. Great location for a TENNIS enthusiast! Located adjacent to one of the best tennis facilities in town. This condo is convenient to everything and very easy to show. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$3,495,000
$12,948/mo
Monthly Payment:
$12,948
Principal & Interest:
$12,948
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $699,000 down)
Winter Park, FL 32789
Orange County School District
5bed 8bath 8,990sq ft $389 / sq ft SFR
Lot Size33,139sq ft Built2010 On Site57days
Moroccan style Mediterranean with fabulous courtyard design perfect for entertaining, this home is in “like new” condition w/ bright, modern-transitional interiors... more
Moroccan style Mediterranean with fabulous courtyard design perfect for entertaining, this home is in “like new” condition w/ bright, modern-transitional interiors with gracious room sizes along with the finest of finishes & detail . Features include exquisite light fixtures, exotic granite/marble counters, incredible custom olde world doors, hand crafted cabinetry, elegant walnut & antique pine hardwood floors, wonderful chef’s open island kitchen with butler's pantry, wine cabinet, desk work station & separate breakfast room overlooking courtyard and pool… elegant generous formal dining & living rooms, gas fireplaces, gentlemen's library… and expansive master suite with sitting area, his & her separate dressing areas w/ terrific closets, shoe closet and lavish “spa like” bath. Bright and open custom floor plan provides great spaces for entertaining large parties or intimate evenings inside or out. 2 additional 1st floor bedroom suites including guest suite detached from the main residence “casita” offering you and your guest plenty of privacy. Upstairs enjoys the 2 additional secondary bedroom suites, a media rm w/ theater, multiple balconies overlooking the courtyard and "resort style" pool & heated spa. This home is designed for outdoor living area with summer kitchen, multiple lanais and terraces, extensive gorgeous iron work, outside shower, swim up seats built into the luxurious pool and more... Truly a special estate property on oversized lot in a sought after premier Via’s setting! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$1,395,000
$5,168/mo
Monthly Payment:
$5,168
Principal & Interest:
$5,168
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $279,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 4,703sq ft $297 / sq ft SFR
Lot Size11,887sq ft Built2007 On Site57days
Exquisite four bedroom, four and one half bathroom Tuscan pool home in Winter Park minutes from Park Avenue. Paver driveway welcomes you to this stunning home with designer wood... more
Exquisite four bedroom, four and one half bathroom Tuscan pool home in Winter Park minutes from Park Avenue. Paver driveway welcomes you to this stunning home with designer wood door at entry and plantation shutters throughout. Open living and dining room layout, with classic crown molding and arched doorways, is great for entertaining. The spacious chef's kitchen looks out to family room, and is appointed with large center island, wood cabinetry, marble countertops, and double oven. Breakfast nook with wine bar overlooks the pool and patio area, perfect for morning relaxation. Family room is open and comfortable with high beamed ceilings, gorgeous stone and wood flooring, and stone fireplace. Downstairs private master suite includes spa tub, separate walk-in shower, his and her walk-in closets, double vanities, and access to outside patio. Office is also downstairs with beautiful, dark walnut wood floors. Large bonus room, as well as three more bedrooms, each with full bath and walk-in closet, are upstairs. Relax on the expansive brick patio with outdoor fireplace and wrought iron accents as you enjoy entertaining around the pool. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$729,000
$2,700/mo
Monthly Payment:
$2,700
Principal & Interest:
$2,700
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $145,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,932sq ft $249 / sq ft SFR
Lot Size13,389sq ft Built1969 On Site57days
Walk to park avenue from this wonderful home in sought after park north. This 4 bedroom 2.5 bath pool home features formal living and dining rooms and a cozy family room with... more
Walk to park avenue from this wonderful home in sought after park north. This 4 bedroom 2.5 bath pool home features formal living and dining rooms and a cozy family room with wood burning fireplace right off the eat in kitchen. Laundry is easier in the oversized indoor laundry room. The master suite has a sitting room with french doors leading to the pool area. Many updates have been done including new tile roof (6yrs), newer heating and air systems (2yrs), pool equipment (3yrs), and newer gas water heater (6yrs). You will love entertaining and grilling out on the expansive covered patio overlooking the pristine pool and lovely backyard. Winter park "a" schools! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$200,000
$740/mo
Monthly Payment:
$740
Principal & Interest:
$740
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $40,000 down)
Winter Park, FL 32792
Goldenrod Orange County School District
1,974sq ft $101 / sq ft MFR
Lot Size16,287sq ft Built1981 On Site57days
If you're an investor looking for a rental property, look no further! This duplex is conveniently located nearby everyday conveniences; like major roadways or stores. A new roof... more
If you're an investor looking for a rental property, look no further! This duplex is conveniently located nearby everyday conveniences; like major roadways or stores. A new roof has just been installed! One side is a 3/2 with a two car garage! The other side is a 2/1 with a one car garage. Both sides are tenant occupied. Call me to schedule your showing appointment today! 12-24 hour notice needed. less
Listing Provided Courtesy of Bhhs Results Realty
Popularity
$2,275,000
$8,428/mo
Monthly Payment:
$8,428
Principal & Interest:
$8,428
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $455,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 6,210sq ft $366 / sq ft SFR
Lot Size40,863sq ft Built2004 On Site57days
Extraordinary Lakefront Mediterranean in Olde Winter Park secluded on quiet brick street on Lake Sue, this exceptional home features quality finishes throughout and lake views... more
Extraordinary Lakefront Mediterranean in Olde Winter Park secluded on quiet brick street on Lake Sue, this exceptional home features quality finishes throughout and lake views from almost every room… impressive entry with exquisite winding stairwell off foyer… Main level includes a spacious island kitchen with granite counters, breakfast area and terraces all open to a warm generous size gathering room with fireplace, full wet bar and balcony overlooking pool & lake, soaring ceilings in elegant 2-story formal living with fireplace and french doors open to lake views, and study/den & bedroom suite (perfect for guests with private entry)… The upper level includes a spacious master suite with separate sitting area/office, fireplace, his/her closets, lavish bath and picturesque elevated lake views along with private balcony -and- 2 other bedroom suites & bonus area at top of stairs… The lower level includes a 5th bedroom suite (presently used as a gym/exercise studio & massage room w/ sauna) and 3 garages... Other features included are 3 gas fireplaces, solid wood custom doors, 8" tall baseboards throughout, beautiful crown molding, trim and built-ins, french doors, and 3 1/2 car garages… tropical pool/patio area featuring wonderful huge covered lanai with complete summer kitchen, tvs and simply an outstanding entertaining area pool & lakeside... there is a lawn area by the lake and boathouse with more entertaining deck area… This home is built like a fortress and extreme attention to detail! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$289,900
$1,074/mo
Monthly Payment:
$1,074
Principal & Interest:
$1,074
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $57,980 down)
Winter Park, FL 32792
Orange County School District
4bed 2bath 1,618sq ft $179 / sq ft SFR
Lot Size8,452sq ft Built1962 On Site58days
Wonderful Winter Park Pines. Cady Way Trail, Ward Park, and Showalter Field. Biking and walking trails, tennis, swimming and golf are all in this community. Enjoy your wood... more
Wonderful Winter Park Pines. Cady Way Trail, Ward Park, and Showalter Field. Biking and walking trails, tennis, swimming and golf are all in this community. Enjoy your wood burning fireplace from both living room and family room. You will love the screened porch, off the family room,and the newly fenced yard which overlooks the park and trail. Easy wood and ceramic floors. Beautiful kitchen appliances (new refrigerator), solid surface counters and dinette area. Updated bathrooms. Very tasteful decor throughout. Utility/bonus room is a great room for hobbies. New garage doors and exterior entrance doors. This home has also been replumbed. Love everything Winter Park has to offer from this home. Great schools, shopping and central convenience. less
Listing Provided Courtesy of Exit Real Estate Results
Popularity
$250,000
$926/mo
Monthly Payment:
$926
Principal & Interest:
$926
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $50,000 down)
Winter Park, FL 32792
Orange County School District
2,110sq ft $118 / sq ft MFR
Lot Size11,459sq ft Built1985 On Site58days
Good rental area, Great property. 3 bed /2bath each side with single car garage and back porch for each. Tenants tend to stay long term. Great oversized tile throughout main... more
Good rental area, Great property. 3 bed /2bath each side with single car garage and back porch for each. Tenants tend to stay long term. Great oversized tile throughout main living areas. Carpet in bedrooms. Walk-in closet, great natural light, sky lights in main living areas, conveniently located near shopping: target/Winn Dixie/Publix/Costco, many restaurants and venues. Minutes from down town Orlando, and easy access to major roadways. Great access to UCF and Full Sail schools. Have had great qualified prospects for tenancies who have kept the property interior well. Enjoy morning coffee from covered porch while enjoying the peaceful wildlife views on the pond. This is a no brainer!! Come, See, Buy! less
Listing Provided Courtesy of Realty Group Specialists, Llc
Popularity
$2,195,000
$8,132/mo
Monthly Payment:
$8,132
Principal & Interest:
$8,132
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $439,000 down)
Winter Park, FL 32789
Orange County School District
4bed 6bath 6,242sq ft $352 / sq ft SFR
Lot Size18,258sq ft Built2013 On Site58days
Meticulously constructed 4 Bedroom 5 full & 1 half bath 6242 square foot "NEW ORLEANS' style pool home is situated on a beautiful oversized lot on a quiet street just steps away... more
Meticulously constructed 4 Bedroom 5 full & 1 half bath 6242 square foot "NEW ORLEANS' style pool home is situated on a beautiful oversized lot on a quiet street just steps away from Lake Maitland. First floor Master Suite w/ fireplace, kitchenette w/ Thermador refrigerator, dishwasher & sink, huge walk in closet & separate laundry room. Master bath has separate vanities, a soaking tub, large walk in shower & fireplace. Gourmet kitchen w/ top of the line commercial style stainless steel appliances, custom cabinetry, granite and marble counter tops & walk in pantry. Billiard/Game room has a fireplace, wet bar w/ wine refrigerator, Thermador refrigerator/freezer & dishwasher. Additional amenities include: Bevolo light fixtures, antique Chinese elm reclaimed wood floors, fabulous ceiling details throughout, extensive custom millwork & built ins, Windsor double insulated energy efficient windows, 2 covered porches & 2 covered balconies, 3 gas fireplaces, ICF (insulated concrete form) construction, Baldwin Estate hardware, Kohler plumbing fixtures, Elevator & 3 laundry rooms. This amazing home is loaded w/ upgrades & extras. Great attention has been paid to the architectural detail & style and should be viewed in person to truly appreciate the quality throughout. 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
844.662.5638
Content provided and owned by Coldwell Banker Residential Real Estate.
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Data last updated: Tuesday, April 28, 2015 at 6:12 AM