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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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$629,000
$2,226/mo
Monthly Payment:
$2,226
Principal & Interest:
$2,226
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $125,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,391sq ft $263 / sq ft SFR
Lot Size11,490sq ft Built1962 On Site345days
Open Sun May 1, 2pm-5pm
Beautifully remodeled four bedroom, two and one half bath home in Winter Park 32789. Home interior is freshly painted, clean as a whistle and ready to move right in! Fantastic... more
Beautifully remodeled four bedroom, two and one half bath home in Winter Park 32789. Home interior is freshly painted, clean as a whistle and ready to move right in! Fantastic corner lot in Brookshire school district with tons of yard space. Very light and bright, beautiful hardwood floors, crown moldings and double paned windows with great views of the outdoors. Full master suite with adjacent bedroom/office plus luxurious bath with garden tub, double vanities and shower. Bedrooms have brand new carpet and built in organizers. You will love the chef's kitchen featuring spectacular granite, wood cabinets with self-closing doors and tons of storage, new kitchen appliances including Kitchenaid convection and GE refrigerator, and generous space for entertaining. Roomy closet pantry for all your needs. Enjoy the lush landscaping and freshly paved back porch with detailed pine in the arched roof. Nice floor plan with formal living area and large family room. Good sized two car garage for parking and storage. Inside utility room with plenty of space for folding. Water heater 2011. Roof 2003. Replumbed. Gutters. Security system. Outside completely repainted. Lots of storage! Great WPHS schools. Very convenient to Windsong, downtown, Park Avenue and shopping. Excellent dog walking and biking. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
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$999,000
$3,535/mo
Monthly Payment:
$3,535
Principal & Interest:
$3,535
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $199,800 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,296sq ft $233 / sq ft SFR
Lot Size15,112sq ft Built2004 On Site353days
Just reduced! Stunning five bedroom, five bath home + office for under a million! Fantastic neighborhood, tree lined streets, great community feel, just a few minutes from park... more
Just reduced! Stunning five bedroom, five bath home + office for under a million! Fantastic neighborhood, tree lined streets, great community feel, just a few minutes from park avenue. Zoned for a-rated public schools and conveniently located to park maitland and other distinguished private schools. Downstairs master with his and her walk-in closets, jetted tub, and french doors that open to the covered lanai. Four bedrooms, three full baths, and bonus room upstairs. Gorgeous designer kitchen with custom cabinetry, granite counters, and gas burner stove. High ceilings, hardwood floors, extensive crown molding, fireplace and more. Screened in pool and summer kitchen are perfect for entertaining. Oversized corner lot with great curb appeal. Home is move-in ready " same day showings available. Call today! less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$5,795,000
$20,508/mo
Monthly Payment:
$20,508
Principal & Interest:
$20,508
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $1,159,000 down)
Winter Park, FL 32789
Virginia Heights Orange County School District
5bed 8bath 7,800sq ft $743 / sq ft SFR
Lot Size1.6acre Built1925 On Site355days
Majestic Winter Park Estate on 1.59 acres of pristine lakefront property. Panoramic views of Lake Virginia from every corner of this stunning home. Private driveway with... more
Majestic Winter Park Estate on 1.59 acres of pristine lakefront property. Panoramic views of Lake Virginia from every corner of this stunning home. Private driveway with electronic gate, motor court, four car garage, guest house, boathouse, and more. Sophisticated and elegant, the main house offers four bedrooms, three full baths, two half baths, formal living and dining rooms, family room, a Chefs kitchen with professional grade appliances, home office, and gym. Screened in lanai, trellis covered patio, and open back porch all overlook the meticulously cared for lawn and gardens, complimented by hanging moss oaks and towering palms. Enjoy breathtaking sunset views over the estates rolling hills. Originally built in 1925, this is a very rare opportunity to own one of Winter Parks most significant estates, offering exclusive privacy and priceless lakefront views. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$475,000
$1,681/mo
Monthly Payment:
$1,681
Principal & Interest:
$1,681
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $95,000 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
6bed 7bath 4,072sq ft $117 / sq ft SFR
Lot Size17,500sq ft Built1935 On Site373days
Back on the market, don't miss out. Previous buyer's financing fell through. This home is for sale $50,000 below appraised value! The newly renovated historic home is on a... more
Back on the market, don't miss out. Previous buyer's financing fell through. This home is for sale $50,000 below appraised value! The newly renovated historic home is on a double lot in the beautiful dubsdread hieghts community. Just steps from the the historic dubsdread golf course and merely minutes from the art district of winter park and downtown Orlando. This custom home was renovated in 2015 on a lot size of 125 x 140. A detached 652 s/f 1 bed/1 bath home is included in sq. footage. The 2+car garage has also been converted into an 1 bed one bath efficiency as well which is includes in the sq footage calculations. 3 lots on both sides of this home are also for sale. realtor only remarks. Custom designed cathedral ceilings in the Family/Great Room will be the talking point of your guests when they visit your new residence. This home has 2 fireplaces in the main house. The following renovations were completed within the last year; travertine flooring, refinished solid oak hardwood flooring, All new cabinets and granite countertops in the kitchen and bathrooms, New Irrigation system, New paved driveway, New exterior paint, and new interior paint in all rooms. The garage conversion/in law suite features a kitchen and 1 bath. The separate guest house features new cabinets in the kitchen and bathroom, and a fireplace. The main house is around 2900sq ft 4bed 4.1/2 bath. the garage conversion and the guest house are both 1/1 and are each aroun 650sq ft. less
Listing Provided Courtesy of HOMEFIRST REALTY
Popularity
$1,695,000
$5,998/mo
Monthly Payment:
$5,998
Principal & Interest:
$5,998
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $339,000 down)
Winter Park, FL 32789
Orange County School District
4bed 6bath 3,824sq ft $443 / sq ft SFR
Lot Size9,900sq ft Built2015 On Site376days
Welcome to The Turnberry by Maroon Fine Homes, a beautiful two-story residence. located in the Via's of Winter Park. Designed for indoor and outdoor living, this home offers... more
Welcome to The Turnberry by Maroon Fine Homes, a beautiful two-story residence. located in the Via's of Winter Park. Designed for indoor and outdoor living, this home offers four bedrooms, four full and two half bathrooms and features a unique play/lap pool and cabana. Featuring a warm transitional architectural style and accented by modern interior design, the home offers a blend of hospitality and sophistication. Elegant wide-planked walnut wood floors travel throughout the interior, from the foyer and great room to the kitchen, dining room and home office. Beautiful finishes including smooth stained beams in the great room, along with extensive interior architectural by Niemann Interiors that further enhance this primary living areas. The kitchen offers a walk-in pantry, center island, appliances by Wolf and Sub-Zero and rich, custom all-wood cabinetry. The home's outdoor living area features an expansive pool with mature existing landscaping. The covered lanai features a summer kitchen with stainless steel grill and pool storage. This relaxing retreat is located not far from Park Avenue. less
Listing Provided Courtesy of MAROON REALTY GROUP LLC
Popularity
$750,000
$2,654/mo
Monthly Payment:
$2,654
Principal & Interest:
$2,654
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $150,000 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 3,400sq ft $221 / sq ft SFR
Lot Size11,229sq ft Built2006 On Site395days
Beautiful white brick home, completely rebuilt in 2006, situated on corner lot in very desirable Sylvan Lake Shores. Enjoy the neighborhood park and lake across the street and... more
Beautiful white brick home, completely rebuilt in 2006, situated on corner lot in very desirable Sylvan Lake Shores. Enjoy the neighborhood park and lake across the street and historical houses throughout the neighborhood lined with brick streets and old oak trees. Home has four nicely sized bedrooms plus another playroom/bedroom and upstairs suite including gorgeous office retreat with stunning built-ins/wet bar/fridge, bedroom and bathroom retreat plus lots of storage for files or holiday decor. Two spacious master bedrooms. One is on first floor with his and hers closets. Master bath has separate vanities and soaking tub with huge shower. Wide plank hardwood floors, custom moldings and high ceilings throughout. Well-appointed kitchen with granite counters, bead board woodwork, sunroom overlooking saltwater pool and private backyard. Natural gas on the street and gas stove in the home. Living room has wood burning fireplace. Family room boasts custom built-in bookshelves. You will love the close proximity to excellent Winter Park schools, Whole Foods and Park Avenue. Convenient to downtown and Baldwin Park. Great walking neighborhood and adjacent to the North Shore of Windsong. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$1,595,000
$5,644/mo
Monthly Payment:
$5,644
Principal & Interest:
$5,644
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $319,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,819sq ft $566 / sq ft CND
Lot Size27,512sq ft Built2008 On Site410days
Fabulous penthouse in the heart of downtown winter park! Steps to park ave with it's world class shopping and dining. This 4th floor corner unit is finished with top quality... more
Fabulous penthouse in the heart of downtown winter park! Steps to park ave with it's world class shopping and dining. This 4th floor corner unit is finished with top quality materials throughout with wolf and subzero appliances, stone and wood flooring. A wet bar with wine cooler and refrigeration drawers. A spacious master suite with 14 foot tray ceiling, an elegant bath and a balcony. The living room features a fireplace and french doors that lead to a balcony with a gas grill and a spiral staircase up to the private roof top terrace with a fireplace and views of the winter park skyline and lake osceola. Villa siena provides you with the privacy of an intimate setting and amenities including a club room with bar, billiards, fitness center and a roof top terrace. Enjoy the downtown lifestyle without giving up the privacy, security and serenity this condo has to offer. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$3,500,000
$12,386/mo
Monthly Payment:
$12,386
Principal & Interest:
$12,386
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $700,000 down)
Winter Park, FL 32789
Orange County School District
6bed 6bath 4,652sq ft $752 / sq ft SFR
Lot Size16,439sq ft Built2016 On Site418days
Pre-construction. To Be Built. Waterfront - Lake Mizell - Chain of lakes. Modern Masterpiece by FG Schaub Custom Homes and designed by David Larson Ltd. This home will be... more
Pre-construction. To Be Built. Waterfront - Lake Mizell - Chain of lakes. Modern Masterpiece by FG Schaub Custom Homes and designed by David Larson Ltd. This home will be nestled among some of the most distinguished homes in Winter Park. This 6 bedroom, 5/1 bathroom home will satisfy the most discriminating buyers. The Modern design will offer the best of indoor-outdoor living by maximizing extensive use of windows to capture the sweeping views of Lake Mizell. This home's interior will boast natural textures, fine lighting, impressive name brand appliances, natural stone throughout, and many energy efficient features. This home will have an impressive pool and new boat house to compliment the connection between nature and modern comfort. The yard and garden will boast an exquisite landscaping package sculpted by Signature Landscape. All just a brief stroll from Rollins College, the Winter Park library, The Alfond, and Park Avenue. less
Listing Provided Courtesy of LA ROSA REALTY, LLC
Popularity
$469,900
$1,662/mo
Monthly Payment:
$1,662
Principal & Interest:
$1,662
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $93,980 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,044sq ft $230 / sq ft SFR
Lot Size7,000sq ft Built1950 On Site434days
Awesome property and low maintenance!! Newly Remodeled Orwin Manor Home. This home has been remodeled from the ground up. The home has great curb appeal and is ready for the new... more
Awesome property and low maintenance!! Newly Remodeled Orwin Manor Home. This home has been remodeled from the ground up. The home has great curb appeal and is ready for the new owner. The home contains 3 bedrooms and 3 full baths which is a rare find in the Orwin Manor area. It has all new cabinets and granite counter tops. New A/C ,new windows ,new wood flooring and tile. The master bedroom has a HUGE closet and shower and a separate tub. Great location and in the 32789 zip code. The backyard is fenced in and has all new landscaping and irrigation. Come look and you will not be disappointed ! Everything is new and done with quality craftmanship! Great location to the Hospital and I4 less
Listing Provided Courtesy of COSTELLO REALTY & DEVELOPMENT
Popularity
$1,585,000
$5,830/mo
Monthly Payment:
$5,830
Principal & Interest:
$5,609
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.38% with $317,000 down)
Winter Park, FL 32789
Orange County School District
6bed 7bath 4,959sq ft $320 / sq ft SFR
Lot Size18,634sq ft Built2001 On Site440days
Located in charming Winter Parks most exclusive neighborhood and only a short bike ride to Park Ave, the exquisite finishes of this Carlos Posada 2001 built corner-lot estate... more
Located in charming Winter Parks most exclusive neighborhood and only a short bike ride to Park Ave, the exquisite finishes of this Carlos Posada 2001 built corner-lot estate are the hallmark of this classic traditional home featuring hickory wood floors & rich custom cherry wood cabinetry. Superlatives are not enough to describe the inspirational setting and design characterized by the complete unification of exterior and interior spaces, all of which is embraced by a lush landscape and crafted to the highest standard. A stunning showcase of luxurious finishes & amenities! The expansive windows & high ceilings bring in wonderful natural light illuminating the home and view of the iconic Winter Park peacocks. Homeowners will love this 4,959 square feet home with 6 bedrooms with 6.5 bathrooms (each bedroom has its own private bath), twin master bedrooms, gourmet kitchen, large bonus room/office, sprawling patios, private staircase, crown molding throughout, large In-Law suite, game/media room, workout room, screened pool, spa, built-in Summer kitchen & bar with lanai plus a cabana with outdoor shower dressing room and a three car garage. This home is steps away from Windsongs private residence club on Lake Mizell. Two minute walk to community access to the Winter Park Chain of Lakes ~ all with A-rated schools! Be sure to visit the VIRTUAL TOUR FOR DETAILS! less
Listing Provided Courtesy of PARKLAND INTERNATIONAL REALTY
Popularity
$2,600,000
$9,201/mo
Monthly Payment:
$9,201
Principal & Interest:
$9,201
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $520,000 down)
Winter Park, FL 32789
Orange County School District
4bed 6bath 4,546sq ft $572 / sq ft SFR
Lot Size23,083sq ft Built2002 On Site440days
New Reduced price! Brand new custom hardwood floors! LAKEFRONT"WINTER PARK CHAIN OF LAKES!!!! Stunning Mediterranean home ideally located on the coveted Winter Park Chain of... more
New Reduced price! Brand new custom hardwood floors! LAKEFRONT"WINTER PARK CHAIN OF LAKES!!!! Stunning Mediterranean home ideally located on the coveted Winter Park Chain of Lakes offering views of the lake and sunsets from nearly every room in the house. This beautiful, 4 bedroom, 5.5 bath pool home includes 2 offices, each with the ability to serve as additional bedrooms. This property has been impeccably maintained with quality finishes throughout; hardwood floors, granite, marble and stainless steel appliances. Resort style living on this 1/2+ acre lot featuring a spacious covered lanai overlooking the professionally manicured grounds, inviting pool and breathtaking Lake Osceola. Enjoy all that lakefront living offers while relaxing on the dock and custom boathouse or cruising the lake on your own 18' SeaRay boat and two Honda Turbo personal watercraft that convey with property. Walking distance to prestigious Park Avenue with upscale shopping, fine dining and access to Sunrail Train Station plus all the legendary performing arts that Winter Park is famous for. less
Listing Provided Courtesy of ABSOLUTE REALTY GROUP, INC.
Popularity
$2,100,000
$9,096/mo
Monthly Payment:
$9,096
Principal & Interest:
$7,431
HOA Dues:
$1,665
(Based on a 30 year fixed loan at 3.38% with $420,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 3,839sq ft $547 / sq ft CND
Lot Size27,512sq ft Built2008 On Site447days
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 WINTER PARK LAND CO.
Popularity
$1,090,000
$4,723/mo
Monthly Payment:
$4,723
Principal & Interest:
$3,857
HOA Dues:
$866
(Based on a 30 year fixed loan at 3.38% with $218,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 2,290sq ft $476 / sq ft CND
Lot Size1.5acre Built2003 On Site447days
Exclusive lakefront condo located on the shores of Lake Virginia! This stunning residence offers pristine pool and lake views from two private patios and includes a deeded,... more
Exclusive lakefront condo located on the shores of Lake Virginia! This stunning residence offers pristine pool and lake views from two private patios and includes a deeded, on-site boat slip. From the secured, gated entry to the impressive architectural exterior this luxury condo has it all. The property boasts 2,290 square feet of spacious living and elegant appointments. The grand marble foyer will welcome you home and lead you to the formal living/dining rooms with pool and lake views. The generously sized kitchen is thoughtfully designed and features solid wood cabinets, granite counter-tops and stainless steel appliances. The kitchen opens to a second living area that can easily include a less formal dining table. The master bedroom has french doors leading to a second private patio also overlooking the lake. It offers a luxurious master bathroom complete with Jacuzzi tub, separate shower, dual vanities, and a large walk-in closet. Two additional size-able bedrooms and two full bathrooms on the other side of the condo provide that sought after split-plan privacy. This residence is conveyed with a vast and private storage area. Located just steps from Park Avenue, enjoy all that our special city has to offer from the convenience of this maintenance-free, plush residence. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$1,598,000
$6,974/mo
Monthly Payment:
$6,974
Principal & Interest:
$5,655
HOA Dues:
$1,319
(Based on a 30 year fixed loan at 3.38% with $319,600 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 3,042sq ft $525 / sq ft CND
Lot Size27,512sq ft Built2007 On Site458days
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 WINTER PARK LAND CO.
Popularity
$898,000
$3,880/mo
Monthly Payment:
$3,880
Principal & Interest:
$3,178
HOA Dues:
$702
(Based on a 30 year fixed loan at 3.38% with $179,600 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,619sq ft $555 / sq ft CND
Lot Size27,512sq ft Built2007 On Site458days
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 WINTER PARK LAND CO.
Popularity
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: Friday, April 29, 2016 at 8:05 PM. Properties in listings may have been sold or may no longer be available.