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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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$1,275,000
$4,512/mo
Monthly Payment:
$4,512
Principal & Interest:
$4,512
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $255,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 4,316sq ft $295 / sq ft SFR
Lot Size14,888sq ft Built1992 On Site35days
Elegant Executive Pool Home Located in Olde Winter Parks Prestigious and Highly Desirable Via's. Majestic Oak Trees Line the Brick Street Leading Into The Circular Driveway.... more
Elegant Executive Pool Home Located in Olde Winter Parks Prestigious and Highly Desirable Via's. Majestic Oak Trees Line the Brick Street Leading Into The Circular Driveway. Gleaming Pine Floors Greet You As You Enter through The Front Door and A Dazzling Crystal Chandler In The Family room With Charming Fireplace and Dramatic 2-Story Ceiling Demands Awe. Kitchen Is A Gourmet Chef's Delight With Granite Counter Tops and Highest Of Quality Line Of Appliances: Subzero, Wolf, Miele and Dacor. Plenty of Beautiful Wood Cabinet Storage. Relax & Enjoy The Florida Room Overlooking the Sparkling Pool & Over Sized Lushly Landscaped Fenced Yard. Spacious Master Suite With Stunning Master Bath. Home Is Exquisitely Appointed Through Out. Homes Offers Outstanding Features: Whole House Generator, Exercise Room/Office In Lower Area, French Doors, Custom Built In Cabinetry In Designated Office, Termite Bond, Plantation Shutters. Minutes To Charming Winter Park Boutiques & Restaurant & Close To The Winter Park Racquet Club. Excellent Schools! less
Listing Provided Courtesy of PREMIUM PROPERTIES R.E SERVICE
Popularity
Your search results are current and complete. Learn more
$649,900
$2,299/mo
Monthly Payment:
$2,299
Principal & Interest:
$2,299
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $129,980 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size13,500sq ft BuiltN/A On Site35days
Home with massive 90 X 151 ft. lot abutting sought-after Windsong neighborhood. Whether you want to demolish the existing home and build a custom masterpiece or take advantage... more
Home with massive 90 X 151 ft. lot abutting sought-after Windsong neighborhood. Whether you want to demolish the existing home and build a custom masterpiece or take advantage of the existing cinder block and cypress footprint and favorable setbacks, this is the property for you. This 3,523+ s.f. home, which is need of significant TLC, boasts 4 bedrooms, 3.5 bathrooms, kitchen, breakfast room, formal dining, formal living, library, family room with brick wood-burning fireplace, study, and workroom. The master suite is unbelievably large and boasts a huge closet (with a cedar-lined seasonal storage area). The existing pool has been resurfaced within the last 10 years. Mature trees and a spacious yard distinguish this property from others in the area. This property is being sold AS-IS. less
Listing Provided Courtesy of PALMANO GROUP RE BROKERAGE LLC
Popularity
$52,000
$184/mo
Monthly Payment:
$184
Principal & Interest:
$184
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $10,400 down)
Winter Park, FL 32792
1bed 1bath 809sq ft $64 / sq ft CND
Lot Size10.1acre Built1974 On Site35days
IF your looking for an amazing rental property with good schools you have found it. Schedule a showing today.
IF your looking for an amazing rental property with good schools you have found it. Schedule a showing today. less
Listing Provided Courtesy of BRENNAN REAL ESTATE GROUP LLC
Popularity
$3,475,000
$12,297/mo
Monthly Payment:
$12,297
Principal & Interest:
$12,297
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $695,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 4,002sq ft $868 / sq ft SFR
Lot Size37,860sq ft Built1957 On Site35days
This is a wonderful opportunity to own a gorgeous and sophisticated Winter Park lakefront estate with 287 of frontage on Lake Osceola. Located on a point of land at the end of a... more
This is a wonderful opportunity to own a gorgeous and sophisticated Winter Park lakefront estate with 287 of frontage on Lake Osceola. Located on a point of land at the end of a cul-de-sac, this unique property takes advantage of the panoramic 180 degree lake views from almost every room in the home. As you approach this one-level home via the tree-lined Chicago brick driveway, you know you are getting ready to experience something special. Interior features include beautiful oak hardwood floors, vaulted ceilings, extensive wanes coting and molding throughout, flexible open floor plan with great spaces for entertaining, wood burning fireplace, and wet bar. The eat-in island kitchen has granite countertops, beautiful tile floors, and great views of the lake. The master retreat has a very large walk-in closet and beautiful master bathroom with marble tile, dual vanities, walk-in shower, and separate tub. The beautifully manicured grounds have multiple areas for entertaining friends or relaxing with family lakeside. There is a 2 level boathouse with covered boatlift, storage room, and rooftop deck. This is a spectacular one-of-a-kind Winter Park lakefront estate perfectly located just minutes from the Park Avenue retail district and all that Winter Park has to offer. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$66,900
$379/mo
Monthly Payment:
$379
Principal & Interest:
$236
HOA Dues:
$143
(Based on a 30 year fixed loan at 3.38% with $13,380 down)
Winter Park, FL 32792
1bed 1bath 753sq ft $89 / sq ft CND
Lot Size12,160sq ft Built1973 On Site36days
Your new condo is waiting for you! This spacious 1 bedroom condo is a one floor end unit. There is a covered front entry with open courtyard view out the back. There is laminate... more
Your new condo is waiting for you! This spacious 1 bedroom condo is a one floor end unit. There is a covered front entry with open courtyard view out the back. There is laminate flooring throughout the main living room/dining room area as well as in the bedroom. The kitchen has tile flooring with a closet pantry. Just off the kitchen is the inside laundry area. The condominium community features a community pool and includes water service. There is plenty of open parking. Conveniently located close to dining, shopping and major highways! This is a Fannie Mae HomePath property! less
Listing Provided Courtesy of RE/MAX TOWN & COUNTRY REALTY
Popularity
$230,000
$813/mo
Monthly Payment:
$813
Principal & Interest:
$813
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $46,000 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
3bed 2bath 1,844sq ft $125 / sq ft SFR
Lot Size12,764sq ft Built1978 On Site36days
Classic winter park home. Original owner and the 1st home built in wrenwood. Fantastic 3 bedroom 2 bath home with formal living room, dining room and family room. Spacious... more
Classic winter park home. Original owner and the 1st home built in wrenwood. Fantastic 3 bedroom 2 bath home with formal living room, dining room and family room. Spacious master bedroom with two closets, vanity area and master bath with step in shower. Split bedrooms and the guest bedrooms also large in size. Cozy kitchen with newer refrigerator and breakfast bar. Glass enclosed florida room overlooks large backyard. Post hurricane roof and a/c. Sprinkler system on well. This home just needs a little work to bring it back to its original glory. Huge corner lot with mature landscaping and great seminole county schools. less
Listing Provided Courtesy of RE/MAX TOWN & COUNTRY REALTY
Popularity
$850,000
$3,071/mo
Monthly Payment:
$3,071
Principal & Interest:
$3,008
HOA Dues:
$63
(Based on a 30 year fixed loan at 3.38% with $170,000 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 3,245sq ft $262 / sq ft SFR
Lot Size17,619sq ft Built1978 On Site36days
5 bedroom, 3 1/2 bath home located on a private cul-de-sac in one of Winter Parks most exclusive areas. This home features 4 bedrooms upstairs with an additional mother in law... more
5 bedroom, 3 1/2 bath home located on a private cul-de-sac in one of Winter Parks most exclusive areas. This home features 4 bedrooms upstairs with an additional mother in law suite or office downstairs. Sunny & large kitchen with bay window, breakfast nook for the family & 2 pantries for cook. Separate formal living & dining rooms. The ultimate in family rooms offers an impressive fireplace centering the room with soaring ceilings, expansive & insulated windows and oversized French doors. Plenty of room for family and entertaining. Guest half bath and large laundry room are also found on the first floor. Step out into the screened lanai to relax overlooking the private, large and peaceful backyard oasis. This spacious home features warm, wood plank floors, tremendous storage, insulated windows and is wired for sound. Seller has kept this home well with its hardy board exterior, two new electrical boxes & more recent roof replacement. School zoned for A rated Dommerich Elementary, Maitland Middle & Winter Park High School. Deeded access to Winter Park chain of lakes with nearby neighborhood boat ramp. This home is a must see and is situated in the established, welcoming neighborhood of Tuscany Place with its tree lined brick streets and cul-de-sac. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$3,495,000
$12,368/mo
Monthly Payment:
$12,368
Principal & Interest:
$12,368
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $699,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 5,700sq ft $613 / sq ft SFR
Lot Size37,236sq ft Built1953 On Site36days
True elegance inside and out... Perched high above the Lake Osceola shoreline on the Winter Park chain of lakes, this Mediterranean estate home has it all including panoramic... more
True elegance inside and out... Perched high above the Lake Osceola shoreline on the Winter Park chain of lakes, this Mediterranean estate home has it all including panoramic lake views with spectacular sunsets. Set on 0.85 acres this home has been meticulously upgraded and maintained over the years and is complete with 5 (or 6) bedrooms, 6.5 bathrooms, large living room, dining room, and family room with eat-in area open to the kitchen. The finished lower level has a full bath and can be a 6th bedroom, billiard room, exercise room, bonus room, media room, or perfect "man cave". The upstairs master retreat has separate office (or nursery), sitting area, his and her closets, and covered balcony to take full advantage of the lake views. It is the perfect setting to get away and relax in privacy. Interior features include 4 bedrooms on the main level, beautiful oak floors, coffered ceilings, extensive molding throughout, 2 temperature controlled wine cellars, 2 fireplaces, built-ins and beautiful lake views from most rooms. There are spaces for every member of the family. The exterior of this private lakefront estate offers multiple terraces and entertaining areas, mature landscaping, beautiful pool overlooking the lake, enclosed boat house with storage room for all your aquatic toys. Just across the lake from downtown Winter Park and the quaint Park Avenue retail district, this estate is well located with easy access to Rollins College, Florida Hospital, WP YMCA, Whole Foods, and downtown Orlando. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$185,000
$654/mo
Monthly Payment:
$654
Principal & Interest:
$654
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $37,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,381sq ft $134 / sq ft SFR
Lot Size11,900sq ft Built1957 On Site36days
Short sale.3/2 great winter park neighborhood with excellent seminole county schools! Walking distance to downtown winter park & ymca. Spaceious living area w/fireplace, bonus... more
Short sale.3/2 great winter park neighborhood with excellent seminole county schools! Walking distance to downtown winter park & ymca. Spaceious living area w/fireplace, bonus office space.Large backyard,screened porch. less
Listing Provided Courtesy of RE/MAX OPTIMA
Popularity
$620,000
$2,194/mo
Monthly Payment:
$2,194
Principal & Interest:
$2,194
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $124,000 down)
Winter Park, FL 32789
Orange County School District
5bed 3bath 3,136sq ft $198 / sq ft SFR
Lot Size18,991sq ft Built1967 On Site36days
Desirable Winter Park Neighborhood, on nearly 1/2 of an acre, corner lot, nestled in secluded tree-lined neighborhood and close to every amenity with easy access to major... more
Desirable Winter Park Neighborhood, on nearly 1/2 of an acre, corner lot, nestled in secluded tree-lined neighborhood and close to every amenity with easy access to major roadways. The perfect combination. This 5 Bedroom (a rare find) 3 bath and 3 car garage is a great family find and the property is AMAZING with room to grow or to just enjoy the privacy . A sprawling ranch has a split plan, formal foyer, formal living room, and formal dining room. The open concept kitchen flows into a large family room with wood burning fireplace. Glass French doors run along the back of home all overlooking 700 square foot covered lanai with large screened pool, ideal for entertaining. Gourmet kitchen with stainless steel appliances, dedicated entertainment area in kitchen featuring beverage cooler & ice maker. Custom kitchen also includes beautiful creamy light glazed 42? custom cabinetry, 9 foot island, granite counters, artistic back-splash & island seating for up to 6, function & counter space is incredible. Bedrooms are generously sized with custom closet shelving for organization. Indoor Laundry. Hardwood floors throughout main living areas, plantation shutters, solid core doors with Emtek hardware, built-in speaker system throughout home & lanai, freshly painted, updated roof, re-plumbed, humidity control variable tonage TRANE AC. Truly a special Winter Park location like no other, close enough to enjoy Park Ave & the best schools, zoned for Dommerich, Maitland Middle & Winter Park High School. Call today. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$499,000
$1,765/mo
Monthly Payment:
$1,765
Principal & Interest:
$1,765
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $99,800 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size21,000sq ft BuiltN/A On Site37days
Beautiful large lot that likely could be split into 2 home sites of approx. 75' x 140' each. When you purchase this lovely land you get a house and guest house for free!... more
Beautiful large lot that likely could be split into 2 home sites of approx. 75' x 140' each. When you purchase this lovely land you get a house and guest house for free! Currently has 1926 home, a studio apartment or office - and a 2 bedroom / 2 bath guest house. Can't beat the land price for potential two buildable lots in Winter Park. Close to downtown Winter Park, the Winter Park Village and Florida Hospital. less
Listing Provided Courtesy of PARKLAND INTERNATIONAL REALTY
Popularity N/A
$270,000
$955/mo
Monthly Payment:
$955
Principal & Interest:
$955
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $54,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size19,090sq ft BuiltN/A On Site39days
this Property is priced for remodel or rebuild - build your new home - next to Baldwin Park with out Baldwin Park HOA Fees - largest lot in Neighberhood - easy access from two... more
this Property is priced for remodel or rebuild - build your new home - next to Baldwin Park with out Baldwin Park HOA Fees - largest lot in Neighberhood - easy access from two streets - currently has home on property less
Listing Provided Courtesy of NICOLE-HUDSON REALTY CORP
Popularity
$674,900
$2,523/mo
Monthly Payment:
$2,523
Principal & Interest:
$2,388
HOA Dues:
$135
(Based on a 30 year fixed loan at 3.38% with $134,980 down)
Winter Park, FL 32792
5bed 4bath 4,163sq ft $162 / sq ft SFR
Lot Size9,000sq ft Built2015 On Site39days
Beautiful new winter park home! The kerrville model energy efficient home features only the best appointments in luxury and quality starting your arrival at the front door. The... more
Beautiful new winter park home! The kerrville model energy efficient home features only the best appointments in luxury and quality starting your arrival at the front door. The cobblestone pavers, barrel tile roof, wrought iron railings and flagstone entry impress your guests upon entry into a generous foyer. The lavish upgrades extend from floor to ceiling throughout this grand home boasting porcelain tile flooring, 6 inch base moldings, raised ceilings and crown moldings. The gourmet kitchen has beautiful maple cabinets, caledonia quartz counter tops, lucent stone and glass mosaic tile backsplashes and quality stainless kitchen aid appliances. The open chefs kitchen with a seven foot island and large 11 x 10 nook looks out to the family room and three sets of french doors leading to covered patio/lanai and stunning pool. This mesmerizing view is manifested in the travertine pavers on the patio/lanai and pool deck that encompass the splendid salt water pool with holland blue pebble interior, sheer decent waterfall, wrapped with a aqua marine glass tile that is nothing less than magnificent! The master suite will not disappoint its owner with plenty of room to retreat and relax. The master bath offers garden bath tub, separate shower, double vanities with granite counter tops and huge walk in closet. This splendid home reaps more room to entertain with 23 x 18 game room and wet bar as well as, a 17 x 16 media room. All five bedrooms are oversized with walk in closets allowing plenty of room for all. less
Listing Provided Courtesy of JOSHUA UNLIMITED INC
Popularity
$359,000
$1,270/mo
Monthly Payment:
$1,270
Principal & Interest:
$1,270
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $71,800 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,406sq ft $255 / sq ft SFR
Lot Size7,052sq ft Built1952 On Site39days
If you want Mid-Century Modern, then look no further! Another fabulous and creative renovation by RBE Construction is now available in Winter Park. Light, bright and airy are... more
If you want Mid-Century Modern, then look no further! Another fabulous and creative renovation by RBE Construction is now available in Winter Park. Light, bright and airy are words that aptly describe this beautiful home, with its vaulted ceilings and open floor plan. Lots of light via the copious windows in the epicenter of the home. Stunning kitchen, with 5-burner gas stove, custom cabinets and marble counter tops, opens invitingly to the living area. WOW FACTOR ALERT........private, and-oh-so-cozy, enclosed front courtyard which exponentially expands entertainment space! Energy efficient double-pane, argon gas windows throughout. Newly landscaped and irrigated. Convenient to Baldwin Park, East End Market, and both downtown areas of Winter Park and Orlando. less
Listing Provided Courtesy of KELLER WILLIAMS WINTER PARK
Popularity
$229,900
$813/mo
Monthly Payment:
$813
Principal & Interest:
$813
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $45,980 down)
Winter Park, FL 32789
Orange County School District
3bed 1bath 1,222sq ft $188 / sq ft SFR
Lot Size7,272sq ft Built1950 On Site39days
Great Investment Opportunity in Winter Park. Walking distance to Park Ave and Winter Park Village. A rated Schools. Rehab or tear down. Sold As Is. Non-inhabitable at present... more
Great Investment Opportunity in Winter Park. Walking distance to Park Ave and Winter Park Village. A rated Schools. Rehab or tear down. Sold As Is. Non-inhabitable at present state. Termite Damage. Property is being sold for the value of the land. Lot 50 x 145. No HOA. less
Listing Provided Courtesy of THE PROPERTY STOP LLC
Popularity
7 8 9 10 11 12 13 14 15 ... 20 30
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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
Website provided and owned by Coldwell Banker Residential Real Estate.
 
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Data last updated: Monday, May 30, 2016 at 10:38 AM. Properties in listings may have been sold or may no longer be available.