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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

1300 Buckingham Road, Winter Park image
1300 Buckingham Road, Winter Park $659,900

Welcome to the Wonderful Neighborhood of Orwin Manor in Winter Park. This home has been completely remodeled adding over 1000 sqft Featuring 3 Bedrooms and 2.5 baths wit...

  • 3 Beds
  • 2.5 Baths
  • Orwin Manor Westminster Sec SubDv.
  • 32789 Zip Code
7732 Fernbrook Way, Winter Park image
7732 Fernbrook Way, Winter Park — Na $325,000

New Home for you, in time for the upcoming New Year! Recently updated and ready to move in, located in a quiet neighborhood, this home offers an open floor plan with spac...

  • 3 Beds
  • 2.5 Baths
  • Fernbrook Trails Ph 2 SubDv.
  • 32792 Zip Code
180 Whipple Avenue, Winter Park image
180 Whipple Avenue, Winter Park $1,960,000

Listing price is at appraised value as of 10/24/22 Appraisal. A++ Location (75% FAR) Buyer can bring their own builder. Only 3 Lots left! If you want true walkability...

  • 32789 Zip Code
1620 Orange Avenue, Winter Park image
1620 Orange Avenue, Winter Park $414,900

Highly desirable and charming 2 bed / 2 bath in Orwin Manor (Winter Park address) with new A/C (6/2021), new shingle roof and mod-bitumen over garage (9/2022), new LG fri...

  • 2 Beds
  • 2 Baths
  • Orwin Manor Westminster Sec SubDv.
  • 32789 Zip Code
690 Osceola Avenue Unit 502, Winter Park image
690 Osceola Avenue Unit 502, Winter Park — Lake Virginia Condos $585,000

Be the first to live in this new lake-front condo with partial views of Lake Virginia and the Downtown skyline. Location, location, location!! Walking distance to Winter ...

  • 2 Beds
  • 2 Baths
  • Lake Virginia Condo SubDv.
  • 32789 Zip Code
1694 Eastbrook Boulevard, Winter Park image
1694 Eastbrook Boulevard, Winter Park $425,000

One or more photo(s) has been virtually staged. Come see this charming home now on the market featuring a screened in patio and sparkling pool! New flooring throughout, f...

  • 3 Beds
  • 2 Baths
  • Eastbrook Sub Unit 05 SubDv.
  • 32792 Zip Code
3948 Cool Water Court, Winter Park image
3948 Cool Water Court, Winter Park $549,900

Amazing opportunity to buy this 5 bedroom home nestled in Winter Park's Oxford Cove, located on a cul-de-sac. This home provides an open floor plan, high celings and is p...

  • 5 Beds
  • 2.5 Baths
  • Oxford Cove SubDv.
  • 32792 Zip Code
2620 Summerfield Road, Winter Park image
2620 Summerfield Road, Winter Park $669,900

Welcome home to this Beautiful Golfside Community. This custom, unique and one-of-a-kind WINTER PARK home backyard is adjacent to the Winter Park Pines Golf Club and tree...

  • 4 Beds
  • 2.5 Baths
  • Golfside Golf Course Sec 01 SubDv.
  • 32792 Zip Code
1645 Dale Avenue, Winter Park image
1645 Dale Avenue, Winter Park $3,150,000

Fabulous custom Winter Park home completed in 2020, situated on a quiet brick street minutes from Park Avenue shopping & restaurants, Phelps Park, the Y & elementary scho...

  • 5 Beds
  • 5.5 Baths
  • Comstock Park SubDv.
  • 32789 Zip Code
638 Saint Dunstan Way, Winter Park image
638 Saint Dunstan Way, Winter Park $485,000

Welcome Home! If you've been looking for a Winter Park home in the highly sought after neighborhood of Winter Park Pines, this is it! Great central location, close to Bal...

  • 3 Beds
  • 2 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
1248 S Pennsylvania Avenue Unit 7, Winter Park image
1248 S Pennsylvania Avenue Unit 7, Winter Park — / $810,900

Welcome home to 1248 S Pennsylvania Drive this is more than just a home...it is a lifestyle! This beautiful Mediterranean-style townhome is located in the sought-after ne...

  • 3 Beds
  • 2.5 Baths
  • Casa Jardin Condo SubDv.
  • 32789 Zip Code
1658 Hibiscus Avenue, Winter Park image
1658 Hibiscus Avenue, Winter Park $750,000 ▼

Excellent opportunity to build your dream home on an oversized lot in Winter Park's highly desirable "Tree Streets" neighborhood. The lot measures approximately 100x137. ...

  • Flora Park First Add SubDv.
  • 32789 Zip Code
2325 Chantilly Avenue, Winter Park image
2325 Chantilly Avenue, Winter Park $1,775,000

Stunning pool home located on a quiet street in the heart of Winter Park includes a private backyard oasis and a detached apartment/guest house. As you step through the f...

  • 5 Beds
  • 4.5 Baths
  • Chantilly Sub SubDv.
  • 32789 Zip Code
1007 S Pennsylvania Avenue, Winter Park image
1007 S Pennsylvania Avenue, Winter Park — Penn Place $1,425,000

This is a true "lock and leave" active lifestyle in the townhouses of Penn Place with only four units. No expense was spared on materials and details. Designed by the hig...

  • 3 Beds
  • 2.5 Baths
  • Penn Place SubDv.
  • 32789 Zip Code
1841 Winter Park Road, Winter Park image
1841 Winter Park Road, Winter Park $850,000

Location, location, location is an understatement for this 3-bedroom 2-bath Winter Park pool home! This charming home comes with a massive family space which opens direc...

  • 3 Beds
  • 2 Baths
  • Charmont SubDv.
  • 32789 Zip Code
1945 Bering Avenue, Winter Park image
1945 Bering Avenue, Winter Park $489,500

You will fall in love with this mid-century Winter Park Bungalow across from Lake Bell in charming Lake Bell Terrace. This home offers 3 Bedrooms, 1.5 baths, family room,...

  • 3 Beds
  • 1.5 Baths
  • Lake Bell Terrace SubDv.
  • 32789 Zip Code
1712 Golfside Drive, Winter Park image
1712 Golfside Drive, Winter Park $665,000

Welcome home to the beautiful Golfside Community with stunning tree-lined streets and where the mailman still delivers to your doorstep! This SPLIT-PLAN 4-bedroom, 2 bath...

  • 4 Beds
  • 2 Baths
  • Greenview At Winter Pines SubDv.
  • 32792 Zip Code
1401 Gladiolas Drive, Winter Park image
1401 Gladiolas Drive, Winter Park $495,000 ▼

AMAZING LOCATION IN WINTER PARK! GORGEOUS Turn-Key FULLY REMODELED 3 BED / 2 BATH HOME with TWO-CAR GARAGE. NO HOA. NEW ROOF (2018), UPDATED PLUMBING (2018), UPDATED ELEC...

  • 3 Beds
  • 2 Baths
  • Garden Lake Estates Unit 2 SubDv.
  • 32792 Zip Code
1621 Puritan Avenue, Winter Park image
1621 Puritan Avenue, Winter Park $360,000 ▼

Nestled in the back of a quiet neighborhood in Winter Park, this spacious 4 bedroom, 2 bathroom pool home offers a great opportunity and prime location. Stepping inside, ...

  • 4 Beds
  • 2 Baths
  • Eastbrook Sub Unit 06 2nd Rep SubDv.
  • 32792 Zip Code
690 Osceola Avenue Unit 504, Winter Park image
690 Osceola Avenue Unit 504, Winter Park — 505 $1,595,000

THIS IS THE HOME YOU HAVE BEEN WAITING FOR! 3 BEDROOMS & 3 BATH split floor plan located in the highly sought-after Lake Virginia Condos nestled in the heart of Winter Pa...

  • 3 Beds
  • 3 Baths
  • Lake Virginia Condo SubDv.
  • 32789 Zip Code
2469 Whitehall Circle, Winter Park image
2469 Whitehall Circle, Winter Park $610,000

An exceptionally updated Winter Park home situated on an large .19 acre lot! Located on a very private circle and zoned for the desirable Brookshire Elementary and Winter...

  • 3 Beds
  • 2 Baths
  • Brookshire Heights 3rd Add SubDv.
  • 32792 Zip Code
785 Via Lombardy, Winter Park image
785 Via Lombardy, Winter Park $5,650,000

Under Construction. Today’s Florida living at its finest in this premier 2023 new construction residence nearing completion in the heart of the Vias by Z Properties Inc. ...

  • 5 Beds
  • 5.5 Baths
  • Sicilian Shores Rep 02 SubDv.
  • 32789 Zip Code
2412 Beman Court, Winter Park image
2412 Beman Court, Winter Park $619,900 ▼

Welcome Home! Wait until you see this Beautiful Home with over 2600 sf and so many Stunning Custom Features that sits on the back of an Oak tree lined cul-de-sac! 4 bedro...

  • 4 Beds
  • 3 Baths
  • Eastbrook Sub Unit 09 SubDv.
  • 32792 Zip Code
1404 Border Drive, Winter Park image
1404 Border Drive, Winter Park $1,175,000

Under Construction. WINTER PARK IS GETTING READY TO WELCOME IT'S NEWEST ADDITION TO THE LUXURY HOME MARKET! This dramatic and sophisticated 4 bedroom/4 bath new construct...

  • 4 Beds
  • 4 Baths
  • Winter Park Village SubDv.
  • 32789 Zip Code
1541 Highland Road, Winter Park image
1541 Highland Road, Winter Park $949,000 ▼

Build on this 91x150 lot in the highly desirable street, minutes from Park Avenue, Baldwin Park, restaurants and much more. Zoned for the Audubon k-8! Schedule your priva...

  • Virginia Heights SubDv.
  • 32789 Zip Code

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