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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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$574,900
$2,129/mo
Monthly Payment:
$2,129
Principal & Interest:
$2,129
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $114,980 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,457sq ft $234 / sq ft SFR
Lot Size11,068sq ft Built1963 On Site115days
Beautiful 4 bedroom 2.5 bath one of a kind home located in Winter Park. Spacious floor plan, gourmet kitchen perfect for entertaining. Large living room featuring a beautiful... more
Beautiful 4 bedroom 2.5 bath one of a kind home located in Winter Park. Spacious floor plan, gourmet kitchen perfect for entertaining. Large living room featuring a beautiful custom fireplace. Lush tropical private back yard with pool. a two car carport and outdoor air-conditioned storage. Excellent Winter Park Schools. This is truly a distinctive must see home. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity N/A
Your search results are current and complete. Learn more
$995,000
$4,388/mo
Monthly Payment:
$4,388
Principal & Interest:
$3,686
HOA Dues:
$702
(Based on a 30 year fixed loan at 3.75% with $199,000 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,619sq ft $615 / sq ft CND
Lot Size27,512sq ft Built2007 On Site116days
Enjoy the convenience of Winter Park living without sacrificing the lifestyle of luxury and comfort that you are accustomed to. Reflecting the classic architecture of Tuscany... more
Enjoy the convenience of Winter Park living without sacrificing the lifestyle of luxury and comfort that you are accustomed to. Reflecting the classic architecture of Tuscany centuries-old Siena, Villa Siena combines Old World design with the modern comforts of estate luxury. Each unit is superbly appointed with fine finishes including stone and hardwood floors, private balconies and Sub-Zero and Wolf appliances. With only four floors, Villa Siena provides you with the privacy of an intimate setting that is rich in amenities including club room with bar, billiards & card lounge, fitness center and rooftop terrace. Villa Siena is located in the heart of Winter Park, walking distance to world class shopping & dining, Rollins College & the Alford Inn. less
Listing Provided Courtesy of Re/max Park Avenue
Popularity
$1,795,000
$7,969/mo
Monthly Payment:
$7,969
Principal & Interest:
$6,650
HOA Dues:
$1,319
(Based on a 30 year fixed loan at 3.75% with $359,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 3,042sq ft $590 / sq ft CND
Lot Size27,512sq ft Built2007 On Site116days
Enjoy the convenience of Winter Park living without sacrificing the lifestyle of luxury and comfort that you are accustomed to. Reflecting the classic architecture of Tuscany... more
Enjoy the convenience of Winter Park living without sacrificing the lifestyle of luxury and comfort that you are accustomed to. Reflecting the classic architecture of Tuscany centuries-old Siena, Villa Siena combines Old World design with the modern comforts of estate luxury. Each unit is superbly appointed with fine finishes including stone and hardwood floors, private balconies and Sub-Zero and Wolf appliances. With only four floors, Villa Siena provides you with the privacy of an intimate setting that is rich in amenities including club room with bar, billiards & card lounge, fitness center and rooftop terrace. Villa Siena is located in the heart of Winter Park, walking distance to world class shopping & dining, Rollins College & the Alford Inn. less
Listing Provided Courtesy of Re/max Park Avenue
Popularity N/A
$1,249,000
$5,529/mo
Monthly Payment:
$5,529
Principal & Interest:
$4,627
HOA Dues:
$902
(Based on a 30 year fixed loan at 3.75% with $249,800 down)
Winter Park, FL 32789
3bed 2bath 2,079sq ft $601 / sq ft CND
Lot Size27,512sq ft Built2007 On Site116days
Enjoy the convenience of Winter Park living without sacrificing the lifestyle of luxury and comfort that you are accustomed to. Reflecting the classic architecture of Tuscany... more
Enjoy the convenience of Winter Park living without sacrificing the lifestyle of luxury and comfort that you are accustomed to. Reflecting the classic architecture of Tuscany centuries-old Siena, Villa Siena combines Old World design with the modern comforts of estate luxury. Each unit is superbly appointed with fine finishes including stone and hardwood floors, private balconies and Sub-Zero and Wolf appliances. With only four floors, Villa Siena provides you with the privacy of an intimate setting that is rich in amenities including club room with bar, billiards & card lounge, fitness center and rooftop terrace. Villa Siena is located in the heart of Winter Park, walking distance to world class shopping & dining, Rollins College & the Alford Inn. less
Listing Provided Courtesy of Re/max Park Avenue
Popularity N/A
$499,000
$1,848/mo
Monthly Payment:
$1,848
Principal & Interest:
$1,848
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $99,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,385sq ft $209 / sq ft SFR
Lot Size6,694sq ft Built2008 On Site116days
Must see to appreciate this lovely 2 story home with master suite down! A welcoming front porch awaits you, with unique landscaping on side patio. Low maintenance with no back... more
Must see to appreciate this lovely 2 story home with master suite down! A welcoming front porch awaits you, with unique landscaping on side patio. Low maintenance with no back yard!! Plantation shutters, volume ceilings, crown molding and dark cherry wood flooring throughout the downstairs with extensive glass presents a light and bright living area opening to the gourmet kitchen. Kitchen features granite counters & breakfast bar, stylish cherry cabinetry and 5 burner gas range! French doors open out to lovely sitting area enhanced by lush garden! Master suite has walk in closet and master bath with Travertine tile, whirlpool tub, separate shower and dual vanities! Upstairs there is a large loft, perfect for office or hobby room, plus 3 bedrooms, 2 walk-in closets and bath available for family or guests! Programmable thermostats on both levels & dual panel alarm system! Environmental features include tank-less water heater and multi-zoned HVAC system! Front porch lighting on timers! All custom window treatments & rooms wired for ceiling fans except kitchen! Surround system wiring in walls! Easy walking distance to East End Market and other trendy restaurants and shops. Enjoy LOW maintenance, NO association fees and all that this convenient location close to Baldwin Park, downtown Winter Park and downtown Orlando has to offer. Call for private showing. Seller is relocating & ready for an offer! less
Listing Provided Courtesy of Olde Town Brokers Inc
Popularity
$839,000
$3,108/mo
Monthly Payment:
$3,108
Principal & Interest:
$3,108
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $167,800 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 2,935sq ft $286 / sq ft SFR
Lot Size12,399sq ft Built1957 On Site117days
Open Sun May 31, 2pm-5pm
Fantastic one story Winter Park home just minutes from Park Avenue! Enjoy living in this fabulous three bedroom, two bath home with 2,935 square feet of open living space.... more
Fantastic one story Winter Park home just minutes from Park Avenue! Enjoy living in this fabulous three bedroom, two bath home with 2,935 square feet of open living space. Hardwood maple flooring flows throughout the home. Formal living room is outfitted with plantation shutters and showcases a beautiful, wood burning fireplace. Kitchen has been updated with new cabinetry, granite counter-tops, and built-in stainless steel appliances. Master bedroom has an over-sized walk-in closet and sliding pocket doors that open to a brick laid, enclosed Florida room. Enjoy outdoor living under the covered patio which features phantom screens and overlooks the charming courtyard with gas fireplace. Wrought-iron fencing and 10’ hedging ensure exclusive privacy. Located in a highly sought after neighborhood, among the lakefront estates, this home is conveniently located to Winter Park’s trendy boutique shops and fine dining. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$245,000
$908/mo
Monthly Payment:
$908
Principal & Interest:
$907
HOA Dues:
$1
(Based on a 30 year fixed loan at 3.75% with $49,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,880sq ft $130 / sq ft SFR
Lot Size8,084sq ft Built1970 On Site118days
**traditional sale**location! Location! Desirable seminole county public schools!**3 bed/2 bath pool home**fenced**new exterior paint**double pane windows**quarry tile **large... more
**traditional sale**location! Location! Desirable seminole county public schools!**3 bed/2 bath pool home**fenced**new exterior paint**double pane windows**quarry tile **large front porch**split bedroom plan **tiled throughout living spaces**foyer opens to huge formal living space with tray ceiling. Galley kitchen features stainless steel appliances & 36" cabinets. Great room boasts wood burning fireplace, bose surround sound and sliders to private fenced yard. Master bedroom has vanity area, walk in closet and master bath with large step in shower. Private outdoor living area features open pool with water feature and ample deck space for relaxing or entertaining. Garage has multiple storage shelves, 2nd fridge (conveys!) and service door to yard. Easy access to major roads and downtown winter park shopping and dining. less
Listing Provided Courtesy of Keller Williams Advantage 2
Popularity N/A
$1,199,000
$4,442/mo
Monthly Payment:
$4,442
Principal & Interest:
$4,442
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $239,800 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,263sq ft $281 / sq ft SFR
Lot Size11,718sq ft Built2005 On Site118days
Fabulous custom five bedroom, five bath home in Olde Winter Park. You will love the light-filled, comfortable two story open concept family room with high ceilings, corner gas... more
Fabulous custom five bedroom, five bath home in Olde Winter Park. You will love the light-filled, comfortable two story open concept family room with high ceilings, corner gas fireplace, surround sound, warm Brazilian cherry wood floors and travertine tile kitchen floors. Luxurious downstairs master suite with two walk-in closets, master bath with his and hers vanities, Jacuzzi bathtub and travertine floors. Kitchen ready for gourmet cooking with custom woods cabinets including glass inserts, granite, wine cooler and stainless steel appliances. Guest bedroom on first floor could also de a modern office or perfect for a nursery. Three large bedrooms upstairs, each with their own bathroom creates a wonderful family or guest retreat. Large pool with raised waterfall spa with outdoors speakers creates a wonderful spa like scape in this wonderful park setting backyard. Idyllic setting with private entrance from nicely landscaped backyard into Phelps Park. Steps from the Winter Park YMCA. Large finished room over detached garaged not included in square footage, could easily become an exercise room, theatre, office or studio. An absolute must see for anyone looking for a wonderful home with all the bell and whistles. less
Listing Provided Courtesy of Bhhs Florida Realty
Popularity
$205,000
$759/mo
Monthly Payment:
$759
Principal & Interest:
$759
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $41,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,388sq ft $148 / sq ft SFR
Lot Size11,136sq ft Built1958 On Site119days
If you've been looking for a place to call home in Winter Park, Look no further! This 3 bed 2 bath block home with carport is ready for a new owner. It sits on over 1/4 acre and... more
If you've been looking for a place to call home in Winter Park, Look no further! This 3 bed 2 bath block home with carport is ready for a new owner. It sits on over 1/4 acre and is fully fenced in, there's plenty of room for a garden or bring your boat/rv. No HOA. The home has tile throughout, kitchen was remodeled. This 2014 the owners installed a new ac unit for the homes 19ft x 9ft enclosed sun room. Newly installed outside ac unit and water heater both in 2013. In 2012, New R30 insulation was put in and ducts were repaired. Close to shopping, YMCA, and all Winter Park has to offer! Excellent Seminole County schools. less
Listing Provided Courtesy of Simplicity: A Re Brokerage Co
Popularity N/A
$244,000
$904/mo
Monthly Payment:
$904
Principal & Interest:
$904
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $48,800 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,827sq ft $134 / sq ft SFR
Lot Size7,620sq ft Built1952 On Site119days
Great 3 bed 2 1/2 bath home with possible 4th bedroom...located in the popular Audubon Garden district. updated Kitchen, Jacuzzi tub, French doors heading to the back yard
Great 3 bed 2 1/2 bath home with possible 4th bedroom...located in the popular Audubon Garden district. updated Kitchen, Jacuzzi tub, French doors heading to the back yard less
Listing Provided Courtesy of Blue Lighthouse Realty Inc
Popularity
$987,000
$3,656/mo
Monthly Payment:
$3,656
Principal & Interest:
$3,656
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $197,400 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,618sq ft $377 / sq ft CND
Lot SizeN/Asq ft Built2008 On Site121days
Unique Condo unit just walking distance from Park Av. in Winter park. Outstanding and exclusive living experiences, allowing buyers to enjoy the excitement and charm of downtown... more
Unique Condo unit just walking distance from Park Av. in Winter park. Outstanding and exclusive living experiences, allowing buyers to enjoy the excitement and charm of downtown Winter Park "city life" with the luxuries and comfort of a beautiful home. The Summerset Unit is a single story 3 bed, 3 bath unit with a very large living room, kitchen and dining area and two Juliet balconies overlooking the town. The open floor plan allows the unit to "feel" much larger than the 2,618 SF unit actually is. Standard finishes include Sub-Zero, Wolf and Bosch appliances, crown molding, 10' ceilings, double pane Pella windows, Trane air conditioning, walk-in closets in every room, granite counter tops in kitchen and every bath, Showers in each bath, Closets and pantry by design include. 3 parking spaces reserved in the attached, secured parking garage and many other luxury items one would expect. The Douglas Grand's location is unparalleled, less than one block from Park Avenue, directly across the street from Central Park and two blocks from Hannibal Square, the location is what makes the Douglas Grand an ideal city-living experience in one of America's most unique towns - Winter Park, FL. less
Listing Provided Courtesy of Fusilier Management Group
Popularity N/A
$625,000
$2,315/mo
Monthly Payment:
$2,315
Principal & Interest:
$2,315
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $125,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,117sq ft $295 / sq ft SFR
Lot Size11,707sq ft Built1958 On Site121days
Open Sun May 24, 1pm-4pm
Beautifully updated three bedroom, two and a half bathroom home in the prestigious tree-lined "Vias" of Winter Park. This highly sought after location is only blocks from the... more
Beautifully updated three bedroom, two and a half bathroom home in the prestigious tree-lined "Vias" of Winter Park. This highly sought after location is only blocks from the Winter Park Racquet Club, Park Avenue, and the Interlachen Country Club. With a NEW AC, NEW plumbing, NEW electrical, NEW double pane windows with lifetime warranty, NEW mahogany front door, NEW paint inside and outside, renovated bathrooms, resurfaced driveway, Brazilian walnut floors, crown molding and trim, that carry out through the over 2,100 square feet home, this home is ready for a new owner. The pool was just re-surfaced and new St. Augustine grass was installed. The kitchen features newly refinished cabinets with granite countertops and stainless steel appliances. The private back yard is bordered by beautiful lush landscaping and surrounds a gorgeous pool and cabana. Both the front courtyard and the cabana are pre-wired for sound. This home has a great open floor plan and is perfect for entertaining. Come see what beautiful Winter Park living should feel like. Seller has plans drawn up to expand the house by 1,361 square feet by adding to the front and over the garage for a new total square footage of 3,478. See the MLS photos for the artist renditions. The plans are available to your Realtor as an attachment in the MLS. less
Listing Provided Courtesy of Creegan Property Group
Popularity N/A
$70,000
$505/mo
Monthly Payment:
$505
Principal & Interest:
$259
HOA Dues:
$246
(Based on a 30 year fixed loan at 3.75% with $14,000 down)
Winter Park, FL 32792
2bed 2bath 1,079sq ft $65 / sq ft CND
Lot Size10.1acre Built1974 On Site122days
Not short sale-not reo-2 bedrooms, 2 bath, top floor, end-unit condo with balcony! This open and bright condo features wood, ceramic tile and carpet flooring throughout, along... more
Not short sale-not reo-2 bedrooms, 2 bath, top floor, end-unit condo with balcony! This open and bright condo features wood, ceramic tile and carpet flooring throughout, along with ceiling fans and blinds. Spacious living room has sliding glass doors that lead out the the balcony porch with a view of the courtyard. Kitchen has an eat-at breakfast bar that overlooks the living room and has a closet pantry, and the oven and dishwasher stay! Bedrooms have plenty of closet space and both bathrooms have bathtubs w/ showers. On dead-end street. Community has swimming pool, tennis courts, playground and recreation facility. Convenient to ucf and full sail. less
Listing Provided Courtesy of Sweet Homes Realty Llc
Popularity N/A
$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 4bath 3,120sq ft $234 / sq ft SFR
Lot Size9,103sq ft Built2015 On Site123days
Take a look at this brand new contemporary cottage style home from david weekley homes. Come enjoy this spacious 2 story home in the heart of winter park. This beautifully... more
Take a look at this brand new contemporary cottage style home from david weekley homes. Come enjoy this spacious 2 story home in the heart of winter park. This beautifully designed and appointed home has plenty of space with its 4 bedrooms, 3.5 baths, study, bonus room, covered lanai and plenty of storage space. It also boasts the newest david weekley "energy saver" construction science that uses double pane/low-e ii vinyl windows, seer 14 a/c system, r-38 blown fiberglass insulation and many other energy-saving features. You will enjoy living among such timeless and elegant upgrades as distressed hardwood flooring that extends throughout the main living spaces and into the owners retreat; full overlay, glazed and raised panel cabinets with crown moulding and beveled knobs in the kitchen and bathrooms and electrical pre-wiring for wall mounted interior electronics. This home is destined to truly enhance the lives of its future owners. Our energy saver homes offer homebuyers the best in energy-efficiency and are backed by our program's heating and cooling energy usage guarantee. These homes are friendlier to you , the environment and your pocketbook! less
Listing Provided Courtesy of Weekley Homes Realty Company
Popularity N/A
$169,000
$626/mo
Monthly Payment:
$626
Principal & Interest:
$626
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $33,800 down)
Winter Park, FL 32789
2bed 2bath 1,160sq ft $146 / sq ft CND
Lot Size5,612sq ft Built1986 On Site123days
Desirable first floor end unit with close proximity to the pool and lakeside dock. No stairs to tackle here. Just walk right into your remodeled 2 bedroom 2 bath unit with... more
Desirable first floor end unit with close proximity to the pool and lakeside dock. No stairs to tackle here. Just walk right into your remodeled 2 bedroom 2 bath unit with gorgeous refinished wood floors and unpack your bags. You can also walk to the Winter Park Village, Trader Joes and the newly remodeled Publix Shopping Center. Screened porch and side open patio are a plus for your outdoor entertaining. less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity N/A
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
Content provided and owned by Coldwell Banker Residential Real Estate.
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Data last updated: Sunday, May 24, 2015 at 1:46 PM