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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

230 S Ranger Boulevard, Winter Park image
230 S Ranger Boulevard, Winter Park $410,000

Welcome to the Winter Park Pines, with tree lines streets and the mailman that delivers to your door! You will not want to miss this beautifully, FULLY renovated home in ...

  • 3 Beds
  • 2 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
Winter Park image
Winter Park $890,000

A great opportunity to invest in three lots with income producing buildings across the street from the new Center for Health and Wellbeing, near Advent Health Winter Park...

  • 32792 Zip Code
1071 Lakeview Drive, Winter Park image
1071 Lakeview Drive, Winter Park $2,995,000

Quintessential Winter Park lakefront living at its best, an incredible opportunity to own a spectacular estate located on the shores of beautiful Lake Virginia, in close ...

  • 5 Beds
  • 5.5 Baths
  • Virginia Heights SubDv.
  • 32789 Zip Code
265 Rippling Lane, Winter Park image
265 Rippling Lane, Winter Park $775,000

Terrific opportunity to get on Lake Killarney - home has great bones and could be renovated to your taste. Or, build new and have the lakefront home of your dreams. Sur...

  • 3 Beds
  • 2 Baths
  • Shores Lake Killarney Sec 02 SubDv.
  • 32789 Zip Code
102 S Interlachen Avenue Unit 109, Winter Park image
102 S Interlachen Avenue Unit 109, Winter Park — The Cloisters $359,000

Beautiful Lake Front Cloisters Condominium Community, located in the Heart of Winter Park and in the most desirable location, only a block away from Park Avenue. This Fir...

  • 2 Beds
  • 1 Baths
  • Cloisters Condo SubDv.
  • 32789 Zip Code
1441 Place Picardy, Winter Park image
1441 Place Picardy, Winter Park $1,785,000

Nestled in one of the most sought-after areas of Winter Park, this magnificent Mediterranean-style estate is moments from the renowned Park Avenue. Custom built and craft...

  • 5 Beds
  • 3.5 Baths
  • Fontainebleau SubDv.
  • 32789 Zip Code
1335 Pirate Lane, Winter Park image
1335 Pirate Lane, Winter Park $375,000

As you step into this beautifully updated 4 BED/2 BATH WATERFRONT HOME in highly sought after Winter Park, you can't help notice a view that will take your breath away! ...

  • 4 Beds
  • 2 Baths
  • Harbour Ridge SubDv.
  • 32792 Zip Code
1210 Oaks Boulevard, Winter Park image
1210 Oaks Boulevard, Winter Park $1,149,000

Modern Gem located a block away from Park Ave! This 3 bedroom, 3.5 bath home boasts open spaces and clean lines inside and out. Highlights include upper and lower master...

  • 3 Beds
  • 3.5 Baths
  • Dixie Terrace SubDv.
  • 32789 Zip Code
185 W Fawsett Road, Winter Park image
185 W Fawsett Road, Winter Park $3,250,000

Elevated on a stunning corner, double lot with panoramic views of Lake Sue, this gorgeous "Aurora award-winning" lakefront estate exudes elegance and grandeur. Luxury abo...

  • 5 Beds
  • 5.5 Baths
  • Forest Hills SubDv.
  • 32789 Zip Code
1737 Indiana Avenue, Winter Park image
1737 Indiana Avenue, Winter Park $449,900

Location, location, location! Highly sought after Winter Park neighborhood. Pride of ownership shows throughout this home. 3/2 Main home and a 1/1 Mother-in-law suite, bo...

  • 5 Beds
  • 3 Baths
  • Lawndale SubDv.
  • 32789 Zip Code
256 N Phelps Avenue, Winter Park image
256 N Phelps Avenue, Winter Park $499,000

Beautifully renovated mid-century modern Winter Park bungalow on a corner lot! Spacious 2/2 with over 1750 SF and high-end finishes will be sure to impress. Gorgeous kitc...

  • 2 Beds
  • 2 Baths
  • Sylvan Heights SubDv.
  • 32789 Zip Code
440 Henkel Circle, Winter Park image
440 Henkel Circle, Winter Park $3,150,000

French Mediterranean lakefront on 1.25 acres moments from Park Avenue, this truly magnificent estate boasts over 200 feet of waterfront on Lake Mizell. The 2007 Parade of...

  • 5 Beds
  • 5.5 Baths
  • Thomas M Henkels SubDv.
  • 32789 Zip Code
1440 Magnolia Avenue, Winter Park image
1440 Magnolia Avenue, Winter Park $825,000

Thoughtfully designed, expertly crafted and built by Gallimore Homes, this move-in-ready CUSTOM beauty is absolutely STUNNING! Nestled on a tree-lined street in the heart...

  • 3 Beds
  • 2.5 Baths
  • Lake Knowles Terrace SubDv.
  • 32789 Zip Code
1451 Lake Florence Way, Winter Park image
1451 Lake Florence Way, Winter Park $425,000 ▼

Welcome home to this gated Winter Park community... Lake Florence Preserve! It is a quaint, 28 home community with access to Lake Florence with BEAUTIFUL community dock, ...

  • 3 Beds
  • 2 Baths
  • Lake Florence Preserve SubDv.
  • 32792 Zip Code
1435 Lake Florence Way, Winter Park image
1435 Lake Florence Way, Winter Park $475,000

Welcome home to this AMAZING gated Winter Park community... Lake Florence Preserve! This quaint, 28 home community has access to Lake Florence with a community dock, so b...

  • 4 Beds
  • 2.5 Baths
  • Lake Florence Preserve SubDv.
  • 32792 Zip Code
677 W Swoope Avenue, Winter Park image
677 W Swoope Avenue, Winter Park $325,000

Location, Location, Location. Right in the heart of Winter Park. This property is the perfect opportunity to build a new home. SOLD AS-IS. NO HOA.. Close to the Wi...

  • 2 Beds
  • 1 Baths
  • Carver Town SubDv.
  • 32789 Zip Code
5271 Pine Lily Circle, Winter Park image
5271 Pine Lily Circle, Winter Park $399,000

PRICED TO SELL! You have to see this one to believe it! Welcome to Sanctuary at Aloma's GATED COMMUNITY, on a quiet, private CUL-DE-SAC with a DIRECT POND VIEW. Located j...

  • 3 Beds
  • 2.5 Baths
  • Sanctuary At Aloma SubDv.
  • 32792 Zip Code
640 Northwood Circle, Winter Park image
640 Northwood Circle, Winter Park $389,000

This neighborhood has been consistently rising in value with new million dollar homes being built in the surrounding neighborhood. Excellent floor plan with master split...

  • 3 Beds
  • 2 Baths
  • Winter Park Oasis SubDv.
  • 32789 Zip Code
657 Dunraven Drive, Winter Park image
657 Dunraven Drive, Winter Park $555,000

Lovely, large, spacious home in Winter Park, Florida. 4 bedrooms, 2.5 bathrooms, with bonus room, perfect for office, study, etc. This home has: plantation shutters, ceil...

  • 4 Beds
  • 2.5 Baths
  • Kenilworth Shores Sec 05 SubDv.
  • 32792 Zip Code
3251 Ellwood Court, Winter Park image
3251 Ellwood Court, Winter Park $417,000

MOVE RIGHT INTO THIS 5 bedroom 2 bath beautiful pool home. This home has been totally remodeled with a farm house feel. New roof, new AC, new doors and windows, fresh pai...

  • 5 Beds
  • 2 Baths
  • Eastbrook Sub Unit 15 SubDv.
  • 32792 Zip Code
7980 Pleasant Pine Circle, Winter Park image
7980 Pleasant Pine Circle, Winter Park $480,000

Enclave at Aloma welcomes you through gated entrance and enjoy living in this secure and beautiful family friendly Winter Park neighborhood! Welcome Home to immaculately...

  • 4 Beds
  • 3 Baths
  • Enclave At Aloma SubDv.
  • 32792 Zip Code
2444 Via Sienna, Winter Park image
2444 Via Sienna, Winter Park $995,000

STUNNING RENOVATION of this Coastal Traditional 4 Bedroom - 3.5 Bath POOL home located in quiet cul-de-sac neighborhood. Oversized front porch accented with red brick. ...

  • 4 Beds
  • 3.5 Baths
  • Cinnamon Shores SubDv.
  • 32789 Zip Code
250 Glenridge Way, Winter Park image
250 Glenridge Way, Winter Park $849,000

Great opportunity! Huge .53 acre lot in superior location steps away from Lake Chelton on brick streets. Audubon K-8 and Winter Park High School. Many options! Build you ...

  • Charmont SubDv.
  • 32789 Zip Code
521 Melrose Avenue, Winter Park image
521 Melrose Avenue, Winter Park — 521 $749,000

Situated behind an ivy draped wall on a quiet street, this fabulous updated townhome located in the heart of Winter Park offers you a low maintenance lifestyle (no HOA du...

  • 3 Beds
  • 2.5 Baths
  • Virginia Heights Rep SubDv.
  • 32789 Zip Code
2409 Mandan Trail, Winter Park image
2409 Mandan Trail, Winter Park $557,000

Charming home in desirable Winter Park! This home has been beautifully maintained and upgrades include Updated kitchen granite countertops, master bath and guest bath ren...

  • 4 Beds
  • 3 Baths
  • Hills SubDv.
  • 32789 Zip Code

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