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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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$625,000
$2,211/mo
Monthly Payment:
$2,211
Principal & Interest:
$2,211
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $125,000 down)

2070 Sharon Road NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
3bed 2bath 1,770sq ft $353 / sq ft SFR
Lot Size10,114sq ft Built1958 On Site1days
Beautiful three bedroom, two bath home in the Vias. Charming character, hardwood floors, crown molding, wood burning fireplace, and more! Private, fenced backyard, is the... more
Beautiful three bedroom, two bath home in the Vias. Charming character, hardwood floors, crown molding, wood burning fireplace, and more! Private, fenced backyard, is the perfect place for relaxing and enjoying the outdoors. In ground pool and an outdoor fireplace compliment the homes open patios. Inside youll be hard-pressed to find a home with more authentic character. Formal living and dining rooms are spacious and the second living/family room with French doors overlooks the beautiful pool and backyard. Master bedroom has a full bath while the two guest rooms share a hall bath. Located in one of Winter Parks most desirable neighborhoods, the Vias offer picturesque streets, A-rated public schools, and are just a short bike ride to many nearby parks and trails as well as Park Avenue, the Racquet Club, and the Winter Park Golf Course. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity N/A
We show you every available listing. Here's how
$3,750,000
$13,271/mo
Monthly Payment:
$13,271
Principal & Interest:
$13,271
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $750,000 down)

511 W Canton Avenue NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
5bed 8bath 8,410sq ft $446 / sq ft SFR
Lot Size37,551sq ft Built2014 On Site2days
Step into this dramatic Mid-Century Modern home and you'll never want to leave. Enjoy the perfection of the glass porcelain floors and dramatic windows, as you overlook the... more
Step into this dramatic Mid-Century Modern home and you'll never want to leave. Enjoy the perfection of the glass porcelain floors and dramatic windows, as you overlook the spectacular courtyard from every room. Entertain large parties simply with the spacious and commercial grade kitchen, grand family and living rooms, and resort-like courtyard. Display art, cars, or RVs in the oversized heated and air-conditioned garage space with over 20 ft. of ceiling height (with space for 19 cars). And, with the push of one button, activate the external shades to cover all exterior windows, doors, and garage doors, providing the ultimate in security and privacy. This one-of-a-kind contemporary masterpiece in the heart of Winter Park is the ultimate in design, privacy, luxury, and security. less
Listing Provided Courtesy of CHARLES RUTENBERG REALTY
Popularity
$189,899
$672/mo
Monthly Payment:
$672
Principal & Interest:
$672
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $37,980 down)

1705 Miller Avenue NEW Added to the site in the last 3 days

Winter Park, FL 32789
Fairview Shores Orange County School District
2bed 1bath 845sq ft $225 / sq ft SFR
Lot Size6,901sq ft Built1956 On Site2days
Enjoy living on a great street in a vibrant area! Charming two bedroom, one bath home is within walking distance to several surrounding businesses and restaurants! Near SunRail,... more
Enjoy living on a great street in a vibrant area! Charming two bedroom, one bath home is within walking distance to several surrounding businesses and restaurants! Near SunRail, Mills Avenue restaurants, College Park, Parke House Academy, museums and theaters. This home features a large living room and a nice sized sunroom overlooking a large backyard with storage shed in the back. The screened in porch is the perfect place to read and have a morning coffee. Recent updates include, new roof with a five year warranty, new water heater, double pane insulated windows, new attic insulation, and freshly painted exterior and interior. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$1,589,000
$5,629/mo
Monthly Payment:
$5,629
Principal & Interest:
$5,623
HOA Dues:
$6
(Based on a 30 year fixed loan at 3.38% with $317,800 down)

925 Poinciana Lane NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
4bed 5bath 4,171sq ft $381 / sq ft SFR
Lot Size11,481sq ft Built2013 On Site2days
Fabulous West Indies modern Mediterranean with sleek, sophisticated interiors with clean transitional lines... very bright open, casual floor plan with wonderful flex spaces and... more
Fabulous West Indies modern Mediterranean with sleek, sophisticated interiors with clean transitional lines... very bright open, casual floor plan with wonderful flex spaces and terrific entertaining home both inside & out! True coastal style craftsmanship with gorgeous wide plank hardwood floors, sleek modern double island bright white kitchen with Sub Zero/Thermador appliances, Danby marble tops, beautiful designer lighting and extensive LED lighting thru-out wide open, spacious living areas with spectacular family/gathering room with high vaulted beamed ceilings and gas fireplace, additional bonus/media room on 1st floor There is an oversized private guest suite with morning bar and outdoor entry on 1st floor The master suite and 2 other bedroom suites are on 2nd floor (there is also a pre-designed elevator shaft if buyer wants added / currently used as 2 oversized storage closets) The outdoor living is breathtaking with large lanai, tropical pool & spa, cabana and summer kitchen along with complete concrete/stucco perimeter wall for private courtyard There is also deeded access to Chain of Lakes via canal to Lake Maitland thru HOA boat ramp at bottom of this street! less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$1,389,000
$4,915/mo
Monthly Payment:
$4,915
Principal & Interest:
$4,915
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $277,800 down)

2525 Via Tuscany NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
5bed 8bath 4,832sq ft $287 / sq ft SFR
Lot Size10,514sq ft Built2007 On Site2days
This fabulous home is situated on a large corner lot in the Vias & offers convenient Winter Park chain of lakes access. Built in 2007 with all the modern amenities, warmth &... more
This fabulous home is situated on a large corner lot in the Vias & offers convenient Winter Park chain of lakes access. Built in 2007 with all the modern amenities, warmth & character you would expect. Exceptional quality & craftsmanship throughout as well as an open floor plan perfect for family living or entertaining. The master retreat & study are downstairs as well as formal dining. The gourmet kitchen is spacious w/ custom cabinetry & Viking stainless steel appliances. The family room has fabulous two-story ceilings. Upstairs are four large bedroom suites w/ walk-in closets & a bonus room. Addl amenities include: 2 fireplaces, 2 laundry rooms, outdoor security cameras connected to indoor TVs, a pool cabana for guests that could be turned into a third car garage, circular driveway, oversized parking pad & much more. Additionally, there is 700 SqFt. of unfinished heated & cooled attic space which is not included in the square footage. The spacious patio area features a covered lanai, salt water pool & outdoor grill. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$365,000
$1,308/mo
Monthly Payment:
$1,308
Principal & Interest:
$1,291
HOA Dues:
$17
(Based on a 30 year fixed loan at 3.38% with $73,000 down)

1132 Valley Creek Run NEW Added to the site in the last 3 days

Winter Park, FL 32792
Seminole County School District
4bed 3bath 2,666sq ft $137 / sq ft SFR
Lot Size23,555sq ft Built1998 On Site2days
A beautifully maintained home in a gorgeous tropical setting along Howell Creek! The home features an open floor plan with formal living and dining areas, an updated kitchen... more
A beautifully maintained home in a gorgeous tropical setting along Howell Creek! The home features an open floor plan with formal living and dining areas, an updated kitchen open to a large family room with a wood-burning fireplace and vaulted ceilings. The master bedroom is downstairs and has a large walk-in closet, an en suite bath with dual sinks, spa tub and shower. There is also an extra bedroom and bath downstairs for your guests. Upstairs you'll find a landing area great for a work space, 2 more bedrooms and a bathroom with dual sinks. Out back there is an enclosed porch for morning coffee and a very spacious open deck area that overlooks the creek in a breathtaking natural setting. Improvements include new roof, exterior paint and gutters in 2014, new glass shower enclosure in 2016, new range in 2015 and HVAC in 2009. This property listing also includes an adjacent parcel that provides additional privacy. Convenient to shopping, major roads and excellent schools! less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$235,000
$831/mo
Monthly Payment:
$831
Principal & Interest:
$831
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $47,000 down)

404 Ellendale Drive NEW Added to the site in the last 3 days

Winter Park, FL 32792
Orange County School District
3bed 2bath 1,865sq ft $126 / sq ft SFR
Lot Size12,822sq ft Built1959 On Site2days
You'll love this open and bright home conveniently located a few minutes from downtown Winter Park and all major roads yet still walking distance to Starbucks, the extensive... more
You'll love this open and bright home conveniently located a few minutes from downtown Winter Park and all major roads yet still walking distance to Starbucks, the extensive trail system, and highly-rated restaurants. This spacious home is PERFECT for entertaining, with 1,865 square feet on a nearly 1/3 acre corner lot! Don't miss the chance to make your home in this quiet neighborhood with top-rated Winter Park schools and no HOA. Comprehensive home warranty included. less
Listing Provided Courtesy of COMMUNITY REALTY ASSOCIATES
Popularity
$1,265,000
$4,476/mo
Monthly Payment:
$4,476
Principal & Interest:
$4,476
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $253,000 down)

1841 Laurel Road NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
4bed 5bath 3,424sq ft $369 / sq ft SFR
Lot Size9,646sq ft Built2016 On Site2days
*New Construction to be completed in two weeks* A gorgeous Dutch West Indies style home located on a tree lined street in quaint Winter Park. This residence has a beautiful... more
*New Construction to be completed in two weeks* A gorgeous Dutch West Indies style home located on a tree lined street in quaint Winter Park. This residence has a beautiful courtyard entrance through a gated front porch. The entryway leads you right into the spacious living areas (dining and gathering room) that open up to the large eat in kitchen. This stunning gourmet kitchen features stainless steel Thermador appliances, tiled backsplash, painted maple wood cabinetry with soft-close dove-tailed drawers and granite countertops. Off of the kitchen is a breakfast area with French doors that access the beautiful backyard and outdoor kitchen with gas grill and a gorgeous pool to enhance the Florida lifestyle. Tons of natural light fill the main living space finished with a majestic gas fireplace. This coveted home boasts both a spa like master suite as well as a library/study on the first floor. On the second floor youll be pleasantly surprised to find 3 bedrooms all with their own on-suites, a loft and a unique bonus space that could be a play or media room. This home is minutes away from Park Avenue Shopping District, Downtown Orlando and is zoned for Audubon Park Elementary, Glenridge Middle and Winter Park High Schools. less
Listing Provided Courtesy of KELLER WILLIAMS WINTER PARK
Popularity
$675,000
$2,390/mo
Monthly Payment:
$2,390
Principal & Interest:
$2,388
HOA Dues:
$2
(Based on a 30 year fixed loan at 3.38% with $135,000 down)

1761 Legion Drive NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
3bed 2bath 2,508sq ft $269 / sq ft SFR
Lot Size16,982sq ft Built1966 On Site2days
Open Sat Apr 30, 1pm-4pm
Large corner lot in sought after Green Oaks subdivision. Original hardwood floors, brick fireplace with built-in bookcases. All bedrooms have walk-in closets. Plenty of storage... more
Large corner lot in sought after Green Oaks subdivision. Original hardwood floors, brick fireplace with built-in bookcases. All bedrooms have walk-in closets. Plenty of storage space. Put your own personal touch into this home. Plenty of space for an addition and pool. Walk to Park Avenue. Good schools. Walking distance to Park Maitland School and the Enzian Theatre. less
Listing Provided Courtesy of KELLER WILLIAMS WINTER PARK
Popularity
$425,000
$1,998/mo
Monthly Payment:
$1,998
Principal & Interest:
$1,504
HOA Dues:
$494
(Based on a 30 year fixed loan at 3.38% with $85,000 down)

350 Carolina Avenue #307 NEW Added to the site in the last 3 days

Winter Park, FL 32789
2bed 2bath 1,529sq ft $278 / sq ft CND
Lot SizeN/Asq ft Built2006 On Site2days
Fantastic Opportunity to live adjacent to Central Park and within a one block stroll from the shops and restaurants of Park Avenue. Enjoy the maintenance free lifestyle of condo... more
Fantastic Opportunity to live adjacent to Central Park and within a one block stroll from the shops and restaurants of Park Avenue. Enjoy the maintenance free lifestyle of condo living in this beautifully renovated two bedroom, two bath unit featuring an open floor plan, wood floors and spacious kitchen with granite counter tops and stainless steel appliances. The expansive master suite includes an oversized bathroom with his and her vanities with two walk-in closets. Inside Utility with washer and dryer included. The unit is located within the newest building of the highly desirable gated Park West community. This unit comes with covered parking and an assigned parking space. Community amenities include an electronic gate, pool, clubhouse and tennis courts. Expect to be impressed - Call today to schedule a showing. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$239,900
$849/mo
Monthly Payment:
$849
Principal & Interest:
$849
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $47,980 down)

521 N Capen Avenue NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size6,001sq ft BuiltN/A On Site2days
6,000 square foot lot in an exciting area of Winter Park's new and dynamic West Side. Adjacent to new homes in the $700,000 range and in the same block as David Weekley's new... more
6,000 square foot lot in an exciting area of Winter Park's new and dynamic West Side. Adjacent to new homes in the $700,000 range and in the same block as David Weekley's new Park West at the Village. What a great location! Walking distance to Winter Park Village and the new Whole Foods. Close to Hannibal Square and its shopping and dining. Easy access to I4. Wonderful schools. This is a great opportunity to build an urban dream home in a location that is second to none for convenience, schools and amenities! Relaxed front setbacks due to neighboring structures and advantageous rear setbacks due to R3 zoning at rear of property. Structure is a tear down and has no value but will provide impact fee relief. less
Listing Provided Courtesy of LA ROSA REALTY, LLC
Popularity
$2,250,000
$7,962/mo
Monthly Payment:
$7,962
Principal & Interest:
$7,962
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $450,000 down)

472 W Swoope Avenue NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size37,554sq ft BuiltN/A On Site2days
Multifamily development site! 150 x 250 vacant lot, 37,554 sf. Rarely available "shovel ready" development for 15 townhouses. Approved with variances in place. Total 41,000 sf... more
Multifamily development site! 150 x 250 vacant lot, 37,554 sf. Rarely available "shovel ready" development for 15 townhouses. Approved with variances in place. Total 41,000 sf with a net of 34,000 sf of net saleable air conditioned space. Each unit has a 2 car attached garage and access to outdoor parking for 7+ extra parking spaces. Four 2 story units and eleven 3 story units. Architectural plans attached for 15 units and 10 units. less
Listing Provided Courtesy of CHARLES RUTENBERG REALTY
Popularity
$499,000
$1,931/mo
Monthly Payment:
$1,931
Principal & Interest:
$1,765
HOA Dues:
$166
(Based on a 30 year fixed loan at 3.38% with $99,800 down)

432 W Swoope Avenue NEW Added to the site in the last 3 days

Winter Park, FL 32789
4bed 4bath 2,604sq ft $192 / sq ft TWN
Lot SizeN/Asq ft Built2014 On Site2days
This beautiful new modern townhome will exceed your expectations. Inside, enjoy the bright spacious rooms with light porcelain tile floors on the first level, wood stairs and... more
This beautiful new modern townhome will exceed your expectations. Inside, enjoy the bright spacious rooms with light porcelain tile floors on the first level, wood stairs and wood second floor, luxury custom modern kitchen and bath cabinets with soft close drawers and quartz countertops, level 5 smooth finished walls and ceilings, solid core doors throughout - and more! This fee simple home has it all from its close proximity to Park Avenue restaurants and shopping to its amazing luxury and design. It is built with the finest quality materials from the exterior to the interior - with the concrete block walls on first and second floors and concrete block demising walls between units to its attractive long-lasting metal roof. Owner Financing available with 40 percent down-market terms. less
Listing Provided Courtesy of CHARLES RUTENBERG REALTY
Popularity
$220,000
$782/mo
Monthly Payment:
$782
Principal & Interest:
$778
HOA Dues:
$4
(Based on a 30 year fixed loan at 3.38% with $44,000 down)

3220 Knottypine Avenue NEW Added to the site in the last 3 days

Winter Park, FL 32792
Orange County School District
3bed 2bath 1,627sq ft $135 / sq ft SFR
Lot Size9,751sq ft Built1981 On Site3days
Owner entertaining all offers of $205K to $220K with $220K being full asking price. GORGEOUS RENOVATED HOME AT TREMENDOUS AFFORDABLE PRICE! Practically everything is new - and... more
Owner entertaining all offers of $205K to $220K with $220K being full asking price. GORGEOUS RENOVATED HOME AT TREMENDOUS AFFORDABLE PRICE! Practically everything is new - and the living will be easy here!! WOW FACTOR - come see!....will be years before you have to worry about replacing a New 25 year Architectural shingle Roof, New Carrier A/C, New Solid wood cabinets and beautiful countertops, New crown molding, and wait till you see the fireplace surround in stacked stone, matching the stacked stone in kitchen. Baths are renovated to "Stunning" as well. High quality wood look floor throughout puts the WOW factor over the top. And the large backyard - easy for relaxing or loosing yourself! Back yard access for boat if needed. This subdivision is extremely convenient to major roadways & shops. The subdivision sells quick!! See it today please! less
Listing Provided Courtesy of REALTY GROUP SPECIALISTS, LLC
Popularity
$349,900
$1,754/mo
Monthly Payment:
$1,754
Principal & Interest:
$1,238
HOA Dues:
$516
(Based on a 30 year fixed loan at 3.38% with $69,980 down)

104 S Interlachen Avenue #515 NEW Added to the site in the last 3 days

Winter Park, FL 32789
2bed 2bath 1,267sq ft $276 / sq ft CND
Lot Size1,236sq ft Built1971 On Site3days
Fabulous view on the 5th floor. Very open and light unit. The Cloisters is one block off of Park Avenue which features quaint shopping and dining. Central Park is the focus of... more
Fabulous view on the 5th floor. Very open and light unit. The Cloisters is one block off of Park Avenue which features quaint shopping and dining. Central Park is the focus of the avenue featuring 2 art festivals, a lovely rose garden, concerts in the park, popcorn movie night and lots of fountains and art displayed throughout the year. The Farmer's Market (open on Saturday mornings) is right around the corner. Attention all snowbirds: The Cloisters and Winter Park is also a great home away from home to enjoy winter away from the harsh weather. The complex is on Lake Osceola of the Winter Park "Chain of Lakes" enjoying boat docks that are first come first serve. You will also enjoy the heated pool and lovely gardens. Will not last!!! less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
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Local real estate services provided by:
Coldwell Banker Residential Real Estate
Coldwell Banker Residential Real Estate
5951 Cattleridge Ave
Sarasota, FL 34232

844.662.5638
Website provided and owned by Coldwell Banker Residential Real Estate.
 
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Data last updated: Saturday, April 30, 2016 at 1:41 PM. Properties in listings may have been sold or may no longer be available.