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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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$969,900
$3,693/mo
Monthly Payment:
$3,693
Principal & Interest:
$3,593
HOA Dues:
$100
(Based on a 30 year fixed loan at 3.75% with $193,980 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,462sq ft $280 / sq ft SFR
Lot Size10,905sq ft Built2004 On Site228days
Stunning four bedroom (plus an office) home with more than 3,400 square feet of exceptional living space in Pennsylvania Place. Gorgeous real hardwood floors throughout. High... more
Stunning four bedroom (plus an office) home with more than 3,400 square feet of exceptional living space in Pennsylvania Place. Gorgeous real hardwood floors throughout. High ceilings and crown moldings. Formal living room with fireplace and formal dining room-both have generous sunlight. Large office on the first floor. Gourmet kitchen with beautiful wood cabinets, granite countertops, stainless steel appliances, large walk in pantry and gas cook top. Eat in area with lots of sunny windows. The downstairs master suite is spectacular with lovely green space views, his and her walk in closets, large master bath with separate shower and tub. The upstairs has three bedroom suites, two full baths, large storage room and a bonus area with an outdoor covered balcony. Pennsylvania Place is wonderful neighborhood with a quiet park, sidewalks and rear entry garages. Walk to Park Avenue, the Winter Park Golf Course, and the Winter Park Village. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
We show you every available listing. Here's how
$109,900
$407/mo
Monthly Payment:
$407
Principal & Interest:
$407
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $21,980 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,084sq ft $101 / sq ft SFR
Lot Size3,443sq ft Built1930 On Site228days
Step back in time and fall in love with this vintage 3 bedroom 2 bath cottage. Add your own favorite plants to the landscape to liven up the curb appeal! A Brick Paver walkway... more
Step back in time and fall in love with this vintage 3 bedroom 2 bath cottage. Add your own favorite plants to the landscape to liven up the curb appeal! A Brick Paver walkway and stairs lead up to the Front Door. Inside you'll find a HUGE Great room that's perfect for entertaining. Windows allow natural light to fill the room. Create the kitchen of your dreams and cook up all your favorite meals. A Breakfast Bar makes it easy to have a quick cup of coffee before heading out the door. Don't miss the Master Suite and two guest bedrooms! There's plenty of room for everyone! Majestic Oaks line the street, giving the community an Old Southern Florida feel. Located close to Central Park in Winter Park - so you can walk to all the special events. Or hop on I-4 to quickly reach area attractions and Downtown Orlando. Make this charming cottage your home, today! All information recorded in the MLS is intended to be accurate but cannot be guaranteed, buyer advised to verify. *If exact square footage or room sizes are a concern, unit should be independently measured. This is a Fannie Mae Homepath Property. Visit the HomePath website for more information. less
Listing Provided Courtesy of Keller Williams Classic Ii
Popularity
$794,900
$2,945/mo
Monthly Payment:
$2,945
Principal & Interest:
$2,945
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $158,980 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,119sq ft $255 / sq ft SFR
Lot Size8,768sq ft Built2015 On Site233days
***Click the virtual tour icon on top left to watch the fly thru rendering video!!*** NEW CONSTRUCTION- Lovely, Traditional Arlington Custom Home. Buy now and choose your own... more
***Click the virtual tour icon on top left to watch the fly thru rendering video!!*** NEW CONSTRUCTION- Lovely, Traditional Arlington Custom Home. Buy now and choose your own finishes! The kitchen will feature solid wood cabinetry, A Kitchen Aid 36" gas cooktop, wall oven/microwave combo, 36" French door refrigerator and granite counters. This home has it all - 4 bedrooms, all en suite, a great loft or study area upstairs. The Master bedroom is downstairs as well as a generous laundry, drop off space and a large covered lanai. Energy features include radiant barrier insulation, NEST smart thermostats and thermal windows. All of this on a quaint brick street at fantastic pre construction pricing. The YMCA, shopping, dining and parks- all just a short stroll away. Call today to make an appointment! less
Listing Provided Courtesy of Arlington Realty Inc
Popularity
$969,900
$3,593/mo
Monthly Payment:
$3,593
Principal & Interest:
$3,593
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $193,980 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,026sq ft $241 / sq ft SFR
Lot Size15,054sq ft Built1964 On Site236days
This BRAND NEW Traditional style home from David Weekley is a coveted one story on a quiet street in a serene and mature pocket of Winter Park. Just completed, this beautifully... more
This BRAND NEW Traditional style home from David Weekley is a coveted one story on a quiet street in a serene and mature pocket of Winter Park. Just completed, this beautifully designed and appointed home has plenty of space with its 5 bedrooms, 5 baths, study, bonus room, covered lanai and plenty of storage. 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 enough other energy-saving features that together they earn the home the Environments for Living Gold Level designation. 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... it's a win-win-win! Your clients won't just love saving money on future energy costs, however; they will also love living among such timeless and elegant upgrades as upgraded flooring throughout; full-overlay, glazed and raised-panel cabinets with crown moulding and beveled knobs in the kitchen, solid surface countertops in the kitchen and bathrooms and electrical pre-wiring for wall mounted interior electronics. This residence is destined to truly enhance the lives of its future owners. less
Listing Provided Courtesy of Weekley Homes Realty Company
Popularity
$599,500
$2,221/mo
Monthly Payment:
$2,221
Principal & Interest:
$2,221
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $119,900 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,403sq ft $249 / sq ft SFR
Lot Size5,250sq ft Built2014 On Site242days
Builder close out on this brand new construction with water view! This custom one of a kind home is the second of three beautiful new custom homes all side by side with direct... more
Builder close out on this brand new construction with water view! This custom one of a kind home is the second of three beautiful new custom homes all side by side with direct views of lake midget. Everything was finished with high end materials and in a contemporary style. This homes features: wood floors, granite counter tops,10 foot ceilings, 8 foot doors, gas fireplace and range, stainless appliances, crown molding, architectural shingle roof, upgraded tile, upgraded lighting and plumbing fixtures, and more. This home is also green conscious with duel zone a/c, tank less hot water systems and upgraded r40 attic insulation and foamed block walls. When you are not enjoying the views from your amazing master suite's balconies, you can walk to orange ave and park ave for shopping or dining. Please call owner directly and not listing office. Info is in the showing instructions. Builders new home to the left at 920 s kentucky appraised for 655,000 (with upgraded professional appliances per buyers request). Builders new home on the right at 940 kentucky appraised at $660,000. Builder wants to close out the project and is motivated so make an offer. House was designed to be 3 or 4 bedroom and is currently set up as a 3 bedroom with 3 living areas but can be changed easily to the 4 bed / 2 living rooms version if buyer would prefer ( see alt plan pic). Don't wait show it today! less
Listing Provided Courtesy of Global Real Estate Services
Popularity
$275,000
$1,018/mo
Monthly Payment:
$1,018
Principal & Interest:
$1,018
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $55,000 down)
Winter Park, FL 32789
Orange County School District
4bed 2bath 1,774sq ft $155 / sq ft SFR
Lot Size11,692sq ft Built1973 On Site242days
Wonderful four bedroom, Winter Park pool home! Set back at the end of a quiet cul-de-sac, in the lovely community of Dommerich Forest, you couldn’t ask for a better... more
Wonderful four bedroom, Winter Park pool home! Set back at the end of a quiet cul-de-sac, in the lovely community of Dommerich Forest, you couldn’t ask for a better location. Just minutes to nearby shops and dining and zoned for “A rated” Dommerich Elementary, Maitland Middle, and Winter Park High School this home is perfectly located for all your needs. Desirable split-plan layout offers a master suite with private bath as well as three generously sized bedrooms, each with ample closet space. Updated kitchen was designed to be the center of the home and is open to the dining area. Large, tiled living room features French doors, which lead out into the covered lanai with built-in bar and sweeping views of the oversized, screen enclosed pool. Built on more than a quarter acre lot this home offers a fenced-in backyard with mature fruit trees, plenty of shade, and great space for additional gardening. Attached, two-car garage provides an abundant amount of storage space. Priced to sell, don’t’ miss the opportunity to see this home. Call for your showing today! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$7,850,000
$29,083/mo
Monthly Payment:
$29,083
Principal & Interest:
$29,083
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $1,570,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 10,307sq ft $762 / sq ft SFR
Lot Size1.3acre Built2000 On Site244days
The difference is in the details" is the statement Marc-Michaels Interior Design has built their reputation upon since they began creating interiors for discerning clients in... more
The difference is in the details" is the statement Marc-Michaels Interior Design has built their reputation upon since they began creating interiors for discerning clients in 1985. The end result is their personal magnificent estate home. The estate was completed in June of 2000 and takes its name from the eagles which live on the grounds. Palazzo delle Aquile (Italian for "Palace of the Eagles") is situated on the eastern shore of Lake Osceola. Beholding aesthetic views through almost every window of the home, the site is one of Florida's finest lake front properties. Located within a short walk of the Winter Park shopping district and five miles from downtown Orlando, the estate maintains a secluded ambiance, yet is in the "heart of the city." It has easy access to local art and antique districts, dining and cultural attractions. Architectural Digest featured the home in their September 2001 issue that displayed "Interior Designers' Own Homes!" Highlighting the Venetian-Gothic inspired architecture that is present throughout the interior spaces and exterior elevations of the home, the article included eight pages of beautiful photography. A few months later, Architectural Digest in their January 2002 issue named Marc-Michaels to their prestigious list they call their "AD 100" - the world's top 100, most talented interior designer firms. This stunning 5-bedroom, 5-full bath (plus 2-half bath) home includes extraordinary amenities and "layers of luxury" that one has dreams of calling "the ultimate home. less
Listing Provided Courtesy of Winter Park Land Co.
Popularity
$417,274
$1,629/mo
Monthly Payment:
$1,629
Principal & Interest:
$1,545
HOA Dues:
$84
(Based on a 30 year fixed loan at 3.75% with $83,455 down)
Winter Park, FL 32792
4bed 4bath 3,201sq ft $130 / sq ft SFR
Lot Size5,748sq ft Built2014 On Site244days
Brand new home in gated community in desirable Winter Park! 4 bedroom, 3.5 bath, 2 car garage home with game room is a must see. Kitchen features Granite countertops, upgraded... more
Brand new home in gated community in desirable Winter Park! 4 bedroom, 3.5 bath, 2 car garage home with game room is a must see. Kitchen features Granite countertops, upgraded cabinets and stainless steel appliances. Laundry room conveniently located upstairs. Front and rear covered lanais. less
Listing Provided Courtesy of Ryland Homes Of Florida Realty
Popularity
$324,900
$1,203/mo
Monthly Payment:
$1,203
Principal & Interest:
$1,203
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $64,980 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,628sq ft $200 / sq ft SFR
Lot Size11,499sq ft Built1956 On Site246days
Charming 3/2 pool home on a large (100 x 115) corner lot. Split floor plan with spacious master suite with 2 closets and additional sink/vanity area. Master bath with Jacuzzi... more
Charming 3/2 pool home on a large (100 x 115) corner lot. Split floor plan with spacious master suite with 2 closets and additional sink/vanity area. Master bath with Jacuzzi tub. Updated bathrooms with glass block. Kitchen, with gas cook top and breakfast bar that opens to family and dining area. Other amenities include stone wood-burning fireplace, French glass doors, Spanish tile, berber carpeting and double pane windows. Private fenced back yard with mature landscaping, open patio and oversized pool. Nice storage room off 2-car carport, perfect for yard tools and pool supplies. Just minutes to Park Ave, hospital, restaurants and fabulous Top-rated schools. Click Virtual Tour link for additional home photos. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$629,000
$2,330/mo
Monthly Payment:
$2,330
Principal & Interest:
$2,330
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $125,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,214sq ft $284 / sq ft SFR
Lot Size10,730sq ft Built1954 On Site250days
Welcome to this terrific pool home in the Park Grove area! Gorgeous wood floors throughout the formal rooms and all the bedrooms. This 4 bed/3 bath has a split bedroom plan... more
Welcome to this terrific pool home in the Park Grove area! Gorgeous wood floors throughout the formal rooms and all the bedrooms. This 4 bed/3 bath has a split bedroom plan layout. Lovely trim work and plantation shutters. Double pane windows throughout. Beautifully renovated eat-in kitchen with granite countertops and stainless steel appliances is open to the spacious family room. Both overlook the wonderful screened-in pool which was just resurfaced along with brand new trim tile installed. As well, the pool deck was refinished too. All of which is completely fenced in with a nice side yard, perfect for a garden or play area. This property offers a tremendous location and is so close to downtown Park Avenue! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$799,000
$2,960/mo
Monthly Payment:
$2,960
Principal & Interest:
$2,960
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $159,800 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 2,300sq ft $347 / sq ft CND
Lot Size2,565sq ft Built1960 On Site251days
Wow Honey, we can have the life style of our dreams... live on the lake and walk to Park Avenue. Lock up and travel as we will!" Rare penthouse in Whispering Waters with the... more
Wow Honey, we can have the life style of our dreams... live on the lake and walk to Park Avenue. Lock up and travel as we will!" Rare penthouse in Whispering Waters with the most amazing and calm views to the east and north over Lake Osceola in the heart of Winter Park. Lightly remodeled to move right in or customize as you wish. At this list price, you can't overspend here. Gas fireplace with tumbled marble surround and wood mantle. Light and bright kitchen with light marble counter-tops, Sub Zero refrigerator and gas stove. Interior laundry. Spacious Master bedroom with large walk-in closet and huge bath with jetted tub. Storm shutters for all east side glass doors. This unit comes with a covered BOAT SLIP, large storage room and one car spot in the gated under complex garage. Complex is 55+, solid financially and an incredible place to live. Whispering Waters amenities include an elevator to right outside your door, a sparkling pool, on site manager and lovely lakefront patio with umbrella tables. Fees include all the usual PLUS your water, power and gas! Heated sq ft is approximate and not warranted. less
Listing Provided Courtesy of Parkland International Realty
Popularity
$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
3bed 4bath 3,769sq ft $609 / sq ft CND
Lot Size27,512sq ft Built2008 On Site251days
This is one of six floor plans available to purchase at Villa Siena. Villa Siena is located in the Historic Downtown section of Winter Park, Florida. Walk to Park Avenue shops,... more
This is one of six floor plans available to purchase at Villa Siena. Villa Siena is located in the Historic Downtown section of Winter Park, Florida. Walk to Park Avenue shops, restaurants and parks. In this premier 1st floor location the floor plan takes advantage of a calm garden view. Unit has gas Wolf cooking and Sub-Zero refrigeration. Top quality materials are used throughout. Common areas include expansive club room which includes a large bar area, pool area and party room. The building and unit are fabulous and bright. Attention to detail can be seen throughout the property. less
Listing Provided Courtesy of Re/max Park Avenue
Popularity
$1,625,000
$6,068/mo
Monthly Payment:
$6,068
Principal & Interest:
$6,020
HOA Dues:
$48
(Based on a 30 year fixed loan at 3.75% with $325,000 down)
Winter Park, FL 32789
Orange County School District
6bed 7bath 5,954sq ft $273 / sq ft SFR
Lot Size17,171sq ft Built2006 On Site252days
Custom built family home on quiet brick cul-de-sac street. Winter Park school district. Deeded access to WP Chain of Lakes with ramp and park. Open plan for entertaining,... more
Custom built family home on quiet brick cul-de-sac street. Winter Park school district. Deeded access to WP Chain of Lakes with ramp and park. Open plan for entertaining, generous room sizes, layered crown moldings, volume ceilings, built-ins, theater and surround sound, decorator lighting, 5 fireplaces, mahogany French doors, plantation shutters, solid Brazilian cherry floors, 2 tankless water heaters, central vac throughout .. Two master suites one down & one up, four bedrooms suites upstairs plus bonus media room with wet bar. Chef's kitchen featuring gorgeous hand crafted cabinetry, granite countertops with Viking appliances, generous island for food prep, 2 dishwashers, 2 sinks with disposals, 48" built in refrigerator, 6 burner gas range, 2 gas ovens with convection, warming drawer, wine bar, large walk in pantry, eat in bar with space for 5, separate sit down kitchen opens to wonderful spacious gathering room, elegant living and dining rooms, home office, exercise room that can be used as a nursery, bonus/flex rooms, great storage.. Tremendous outdoor living, a large private fenced yard, multiple covered porches, putting green, brick and travertine patios, saltwater pool with fountain features, separate patio with fireplace, , circular cobblestone driveway, oversize 4 car garage, lush landscape, with towering oaks, generator for whole house, oversize lot, walking distance to WPRC, City of WP playground. less
Listing Provided Courtesy of The Sheridan Network.com
Popularity N/A
$1,249,999
$4,788/mo
Monthly Payment:
$4,788
Principal & Interest:
$4,631
HOA Dues:
$157
(Based on a 30 year fixed loan at 3.75% with $250,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 5bath 4,998sq ft $250 / sq ft SFR
Lot Size20,120sq ft Built2009 On Site257days
Beautiful Mediterranean-inspired Winter Park home, recently complete in 2009, sits on a rare, private, half acre, corner lot. Small, infill neighborhood gives the street a... more
Beautiful Mediterranean-inspired Winter Park home, recently complete in 2009, sits on a rare, private, half acre, corner lot. Small, infill neighborhood gives the street a "gated community feel". Exterior features old world custom stucco, tiled roof, andlow maintenance, drought tolerant zoysia grass. It is surrounded by several 60 year-old oak trees that canopy over the oversized front circular paver driveway and oversized rear paver driver. The open pool features a 50'x 38' travertine pool deck, 41'x 21' pool, oversized 7'x 8' gas heated spa, with raised water features and two gas burning fire bowls. Each lanai and verandah is approximately 16'x16' fully covered and connecting. The verandah features a gas fireplace, with a Cabana for outdoor grilling.Both the lanai and verandah feature travertine flooring, with remote controlled motorized screened archways that extend the indoor/outdoor living area. less
Listing Provided Courtesy of The Sheridan Network.com
Popularity
$188,500
$973/mo
Monthly Payment:
$973
Principal & Interest:
$698
HOA Dues:
$275
(Based on a 30 year fixed loan at 3.75% with $37,700 down)
Winter Park, FL 32789
Orange County School District
1bed 1bath 539sq ft $350 / sq ft CND
Lot Size24,593sq ft Built1956 On Site257days
This one bedroom, one bath studio offers tree tops views overlooking beautiful Winter Park golf course, and walking distance to historic downtown Park Ave. Features include a... more
This one bedroom, one bath studio offers tree tops views overlooking beautiful Winter Park golf course, and walking distance to historic downtown Park Ave. Features include a fairly new renovated kitchen, mahogany floors and quarry tile, crown moulding, built in cabinets, and bookshelves, AC replaced approx 2 years ago, and oversized windows that stream natural light through out. Located on Park Ave in Winter Park allow you to walk to all restaurants, shops, night life and entertainment, the Morse Museum,sidewalk and Art show. Turn key opportunity. less
Listing Provided Courtesy of Century 21 Metro Lifestyles
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
Content provided and owned by Coldwell Banker Residential Real Estate.
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The information being provided by Mid Florida Regional MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Mid Florida Regional MLS. Coldwell Banker Residential Real Estate is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Coldwell Banker Residential Real Estate, a broker participant of Mid Florida Regional MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site.

The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Mid Florida Regional MLS and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited.

Copyright 2014 Mid Florida Regional MLS. All rights reserved.

Data last updated: Monday, December 22, 2014 at 2:17 PM