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Winter Park Homes for Sale

Winter Park, Florida, is a suburban city found in Orange County and part of the Orlando-Kissimmee-Sanford metro area. With a rich historic history, Winter Park was founded as a resort community in the early 20th century. Winter Park has grown and is now known for its vibrant main street, luxury communities, museums, galleries, parks and an incredible chain of lakes popular for skiing, boating, fishing and general recreation.

One of the most popular and renowned areas of the City is Park Avenue, a traditional bricked street which provides an amazing variety of fine and casual dining, boutique shopping, entertainment, a central park and museums. The City is home to a public golf club, historic cemetery, train station, art galleries and a famous boating tour.  Additional popular activities include visiting the Winter Park Village mall, Annie Russell Theatre, Rollins College, Charles Hosmer Morse Museum of American Art, Cornell Fine Arts Museum, Hannibal Square, Mead Botanical Gardens, Kraft Azalea Park and the Winter Park Historical Museum. The scenic boat tours also provide a great way to see the beautiful luxury homes and natural beauty found throughout the City. Winter Park is also host to the world-famous Winter Park Sidewalk Art Festival, which is the largest and oldest of the art festivals found in the country today.

Winter Park is part of the Orange County Public School system and also boasts great schools from public elementary schools to well-known colleges. Some of the top-ranked schools in Winter Park include: Aloma Elementary School, The Geneva School, The Parke House Academy, Full Sail University, Lakemont Elementary, St. Margaret Mary Catholic School, Trinity Preparatory, Winter Park High, Rollins College, Valencia Community College and the Crealde School of Art. 

Winter Park offers many forms of housing including luxury, waterfront, golf front, single-family homes, townhomes, condos, and villas. However, most are single-family homes and tend to be larger with four or more bedrooms. A significant number of the single-family homes have been custom built and target buyers looking for luxurious amenities. A significant number of large estate homes are waterfront and located on the Winter Park Chain of Lakes. The average home listed on the market in Winter Park is about $856K; however, prices can easily range into the multi-millions for some of the larger estate homes.

Some of the most desirable communities in Central Florida are located in Winter Park including Bear Gully Bay, Bear Gully Pointe, Bengerts Bend, Brookshire Heights, Camwood, Charmont, Comstock Park, Conwill Estates, Dixie Terrace, Dubsdread Heights, Ellno Willo, Forest Hills, Fountainhead, Glencoe, Golfview Terrace, Green Oaks, Green Terrace, J Kronenberger, Kenilworth Shores, Killarney Circle, Lake Howell, Lake Howell Lane, Lake Knowles Terrace, Lake Virginia, Maitland Shores, Osceola Place, Park Grove, Sevilla, Shores Lake Killarney, Sicilian Shores, Sylvan Lake Shores, Sylvan Park, Timberlane Shores, Tuscany Place, Tuscany Terrace, Twelve Oaks, Virginia Heights, Windsong and many more.  

Looking to sell your home in Winter Park? Follow this link to get an "Instant" Home Value Report

Newest Winter Park Homes for Sale

1550 Bryan Avenue, Winter Park image
1550 Bryan Avenue, Winter Park $1,895,000

Under Construction. Offered by Rex-Tibbs Construction and to be completed in FEB 2019 - custom builder in the Winter Park area for over 35 years! Close to Park Avenue/dow...

  • 5 Beds
  • 6.5 Baths
  • Sylvan Park SubDv.
  • 32789 Zip Code
7957 Pleasant Pine Circle, Winter Park image
7957 Pleasant Pine Circle, Winter Park $432,900

BEAUTIFUL HOME AT THE "ENCLAVE AT ALOMA" LOCATED IN WINTER PARK. GATED COMMUNITY. 5 BEDROOMS AND 3 BATHROOMS, MODERN COURMET KITCHEN WITH GRANITE COUNTER TOPS WITH 42" CA...

  • 5 Beds
  • 3 Baths
  • Enclave At Aloma SubDv.
  • 32792 Zip Code
1260 N Park Avenue, Winter Park image
1260 N Park Avenue, Winter Park $2,695,000

This is a breathtaking "gated" modern Mediterranean masterpiece on a premier street right through downtown Winter Park. A short stroll along famed Park Avenue to all of t...

  • 6 Beds
  • 7.5 Baths
  • Park Avenue SubDv.
  • 32789 Zip Code
866 Via Lugano, Winter Park image
866 Via Lugano, Winter Park $7,895,000

Located in the desirable Winter Park Via's on Lake Maitland, this breathtaking six-bedroom, ten-bath Mediterranean estate has been crafted with the finest finishes. Built...

  • 6 Beds
  • 9.5 Baths
  • D D Cady Sub SubDv.
  • 32789 Zip Code
2528 Tuscaloosa Trail, Winter Park image
2528 Tuscaloosa Trail, Winter Park $385,000

4 BR 2 BA in Dommerich Hills, original owners have recently replaced windows & slider, roof & gutters , AC and ducting, electrical panel, water heater and the pool has be...

  • 4 Beds
  • 2 Baths
  • Dommerich Hills Fourth Add SubDv.
  • 32789 Zip Code
1501 W Fairbanks Avenue, Winter Park image
1501 W Fairbanks Avenue, Winter Park $525,000

Location, Location, Location!! This office on W Fairbanks is ready for a new owner. Zoned for an office/store. This desirable location is perfect for your business or ...

  • 32789 Zip Code
1940 Via Contessa, Winter Park image
1940 Via Contessa, Winter Park $1,195,000

This is a wonderful opportunity to live in an elegant pool home in the heart of the Winter Park Via's, one of Winter Park's most sought-after neighborhoods nestled amongs...

  • 4 Beds
  • 3.5 Baths
  • Lugano Terr SubDv.
  • 32789 Zip Code
2615 Via Tuscany, Winter Park image
2615 Via Tuscany, Winter Park $1,195,000

This modern Mediterranean one-owner home is situated on a beautiful Via Tuscany corner lot. The home is within walking distance to Winter Park Racquet Club and the city o...

  • 4 Beds
  • 3.5 Baths
  • Maitland Shores First Add SubDv.
  • 32789 Zip Code
581 Sylvan Drive, Winter Park image
581 Sylvan Drive, Winter Park $2,795,000

This premier Winter Park lakefront lot on Lake Osceola provides an opportunity to build anew on an absolutely beautiful elevated lot of approximately 0.75 acres. It overl...

  • Osceola Or Lakeview Deed SubDv.
  • 32789 Zip Code
2161 Sharon Road, Winter Park image
2161 Sharon Road, Winter Park $1,150,000

This premier Via’s property is secluded on a quiet, dead-end street with over a half-acre lot (over 25,000 square feet), creating an estate feel to this wonderful private...

  • Tuscania SubDv.
  • 32789 Zip Code
1148 Howell Branch Road, Winter Park image
1148 Howell Branch Road, Winter Park $394,500

LOCATION! LOCATION! LOCATION! Don"t miss out on this rare opportunity to purchased this newly renovated gem located in the much desirable Winter Park area. Just a short f...

  • 4 Beds
  • 2 Baths
  • Maitland Shores First Add SubDv.
  • 32789 Zip Code
2207 Hawick Lane, Winter Park image
2207 Hawick Lane, Winter Park — Na $399,000

One or more photo(s) has been virtually staged. Beautiful end unit townhome in Winter Park! Fantastic kitchen with granite countertops, soft close drawers and stainless ...

  • 3 Beds
  • 2.5 Baths
  • Casa Villanova SubDv.
  • 32792 Zip Code
785 W Canton Ave, Winter Park image
785 W Canton Ave, Winter Park $829,999

You can have it all, almost every upgrade available is in the esteemed Gardens at Park West located in historic Winter Park 32789. Walking distance to upscale boutique sh...

  • 3 Beds
  • 3.5 Baths
  • Canton Ave Cottages 1 SubDv.
  • 32789 Zip Code
1400 Green Cove Road, Winter Park image
1400 Green Cove Road, Winter Park $3,995,000

Timeless, classic, sophisticated, and exceedingly peaceful… A once in a lifetime opportunity to live in a premier Winter Park Chain of Lakes estate home on almost an acre...

  • 5 Beds
  • 5.5 Baths
  • Camwood Sub SubDv.
  • 32789 Zip Code
702 Driver Avenue, Winter Park image
702 Driver Avenue, Winter Park $599,000

Just reduced!! Welcome to this Beautiful, Historic/Custom Remodeled Gem. Featuring 3667 sq. ft. on .32 acres. Pavers adorn the extensive driveway. Expect to be impressed!...

  • 5 Beds
  • 4.5 Baths
  • Dubsdread Heights SubDv.
  • 32789 Zip Code
2218 Via Tuscany, Winter Park image
2218 Via Tuscany, Winter Park $2,749,000

Under Construction! Welcome to this very special custom home built by Zoltan Homes. Situated in a prime location in Winter Park. Tremendous open floor plan with over 11ft...

  • 5 Beds
  • 5.5 Baths
  • Tuscany Terrace SubDv.
  • 32789 Zip Code
695 Blairshire Circle, Winter Park image
695 Blairshire Circle, Winter Park $420,000

Brick and block, one story, three bedrrom 2 1/2 bath, 2 car over sized garage, shingle roof. Private courtyard, beautiful garden, fenced yard.

  • 3 Beds
  • 2.5 Baths
  • Brookshire Heights 4th Add SubDv.
  • 32792 Zip Code
860 Mayfield Avenue, Winter Park image
860 Mayfield Avenue, Winter Park $1,185,000

Beautiful four bedroom, three bath home in one of Winter Park's most desirable neighborhoods. Located just a short walk to Park Avenue, this home sits on a quiet, tree l...

  • 4 Beds
  • 3 Baths
  • J Kronenberger Sub SubDv.
  • 32789 Zip Code
2845 Aloma Avenue, Winter Park image
2845 Aloma Avenue, Winter Park $330,000

Welcome home to your completely renovated little gem in Winter Park Estates! This 3 bedroom 2 bath with a den is sure to impress with all of its updates. The home has h...

  • 3 Beds
  • 2 Baths
  • Winter Park Estates SubDv.
  • 32792 Zip Code
1440 Bonnie Burn Circle, Winter Park image
1440 Bonnie Burn Circle, Winter Park $699,000

Rare and wonderful opportunity to own a quality home nestled in the heart of desirable Winter Park. Located on a shaded & quiet street, within a short distance to all the...

  • 4 Beds
  • 3.5 Baths
  • Banks Colonial Estates SubDv.
  • 32789 Zip Code
922 Bonita Drive, Winter Park image
922 Bonita Drive, Winter Park $1,595,000

This stunning modern Mediterranean estate is situated on an oversized corner lot and on a beautiful brick street in a sought-after neighborhood, with convenience to ICC, ...

  • 5 Beds
  • 5 Baths
  • Comstock Park SubDv.
  • 32789 Zip Code
1401 Green Cove Road, Winter Park image
1401 Green Cove Road, Winter Park $1,675,000

This elegant Tuscan Mediterranean residence is just steps from Park Avenue on a large corner lot. Timeless architecture is perfectly blended with an interior layout and u...

  • 4 Beds
  • 4.5 Baths
  • Camwood SubDv.
  • 32789 Zip Code
1602 Alabama Drive Unit 403, Winter Park image
1602 Alabama Drive Unit 403, Winter Park — 1602 $395,000

This penthouse unit at The Alabama is available for the first time since the original hotel-to-condo conversion was completed in 1981. Originally three units combined in ...

  • 2 Beds
  • 2 Baths
  • Alabama Condo SubDv.
  • 32789 Zip Code
1602 Alabama Drive Unit 405, Winter Park image
1602 Alabama Drive Unit 405, Winter Park — 1602 $925,000

This penthouse unit at The Alabama is available for the first time since the original hotel-to-condo conversion was completed in 1981. Originally three units combined in ...

  • 3 Beds
  • 3 Baths
  • Alabama Condo SubDv.
  • 32789 Zip Code
1602 Alabama Drive Unit 404, Winter Park image
1602 Alabama Drive Unit 404, Winter Park — 1602 $1,195,000

This is the first time the penthouse unit at The Alabama has ever been available for purchase since the original hotel-to-condo conversion was completed in 1981. Three un...

  • 4 Beds
  • 5 Baths
  • Alabama Condo SubDv.
  • 32789 Zip Code

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