Login

Winter Park Real Estate Search

City

Subdivision

Price

Max List Price

Beds

Baths

Advanced Search

Address Search

Advanced Search

See ALL the Homes for Sale in Winter Park
Map Search

See Homes for Sale in Winter Park on a Map
Market Report

Stay up to date on the Winter Park market

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

1471 Harmon Avenue, Winter Park $385,000

Introducing an exceptional opportunity in coveted Winter Park. Welcome to 1471 Harmon Ave, a remarkable property boasting a spacious 7,139 square foot lot. With R-2 zonin...

Lawndale SubDv.
32789 Zip Code

532 Darcey Drive, Winter Park $575,000

Expect to be impressed! This 3 bedroom/1.5 bathroom CORNER lot home has been completely renovated and is located in the desirable Brookshire Heights neighborhood. The hom...

3 Beds
1.5 Baths
Brookshire Heights SubDv.
32792 Zip Code

1155 Wildmeadow Run, Winter Park $769,000

Welcome to the exclusive gated community, Meadows at Hawk's Crest, located in sought-after Winter Park northeast of Orlando. We promise that this house will not disappoin...

4 Beds
3.5 Baths
Meadows At Hawks Crest SubDv.
32792 Zip Code

417 Saint Dunstan Way, Winter Park image

417 Saint Dunstan Way, Winter Park $534,900

She. Is. A. Prize. So who is gonna win the prize? Living it up in the stylish Winter Park Pines, you'll find her in one of the nicest neighborhoods in ALL of Central Flor...

4 Beds
2 Baths
Winter Park Pines SubDv.
32792 Zip Code

625 Brechin Drive, Winter Park $749,900

A timeless home awaits among the tree canopies of Kenilworth Shores, a tried-and-true Winter Park neighborhood steeped in history. A pristine property and beautifully app...

3 Beds
2 Baths
Kenilworth Shores Sec 04 SubDv.
32792 Zip Code

1612 Eastbrook Boulevard, Winter Park image

1612 Eastbrook Boulevard, Winter Park $399,900

Attention All Buyers and Investors…This is a Must See 3br/2bath single story home in one of Winter Parks highly sought out neighborhoods in Eastbrook. This property has N...

3 Beds
2 Baths
Eastbrook Sub Unit 05 SubDv.
32792 Zip Code

428 S Phelps Avenue, Winter Park $895,000

Located in the quaint, desirable Kenilworth Shores of Winter Park is where you will find this UPDATED traditional home that features over 2100 sq. ft., boasting 3 bedroom...

3 Beds
2 Baths
Kenilworth Shores Sec 02 SubDv.
32789 Zip Code

2038 Jewell Avenue, Winter Park $330,000

Just listed! This adorable two bedroom bungalow is located in Central Florida’s hottest zip code! Nestled between Winter Park and College Park, this home boasts beautiful...

2 Beds
1 Baths
Pines SubDv.
32789 Zip Code

1423 Westchester Avenue, Winter Park image

1423 Westchester Avenue, Winter Park $739,000

THE ORWIN MANOR BUNGALOW // Welcome home to this charming traditional bungalow-style home located in the sought after neighborhood of Orwin Manor. This residence was buil...

3 Beds
2 Baths
Orwin Mnr Westminster SubDv.
32789 Zip Code

1460 Sunset Drive, Winter Park $2,299,000

Welcome to Old Winter Park's coveted Tree Streets - a place where your dream home is waiting for you! This truly remarkable 5/3 property rests in a neighborhood teeming w...

5 Beds
2.5 Baths
Lake Knowles Terrace SubDv.
32789 Zip Code

722 Carvell Drive, Winter Park $425,000

Welcome home to this charming 3 bedroom, 2 bathroom home in Winter Park Estates, zoned for top-rated schools Lakemont Elementary, Maitland Middle, and Winter Park High Sc...

3 Beds
2 Baths
Winter Park Estates SubDv.
32792 Zip Code

2080 Sharon Road, Winter Park $3,595,000

A truly stunning 2022 transitional, modern residence recently completed in the heart of the Vias by Z Properties Inc. Tremendous “off the charts” quality in this custom-d...

4 Beds
4.5 Baths
Tuscania SubDv.
32789 Zip Code

2020 Strathaven Road, Winter Park $515,000

Terrific opportunity to renovate or restart and build new! Situated on a large .30 acre (13,035 sf) corner lot, the property offers lots of possibilities! Tucked away i...

4 Beds
2 Baths
Kenilworth Shores Section Seven SubDv.
32792 Zip Code

870 Carver Street, Winter Park $325,000

Great Investment Opportunity (SOLD AS IS) This three bedroom one bath home is in need of a total makeover, or tear down and build your own new home. Home is situated in ...

3 Beds
1 Baths
Magnolia Gardens Sub SubDv.
32789 Zip Code

2901 Clever Lane, Winter Park — 03 $464,790

Under Construction. At Pulte, we build our homes with you in mind. Every inch was thoughtfully designed to best meet your needs, making your life better, happier and easi...

3 Beds
2.5 Baths
Grayson Square SubDv.
32792 Zip Code

1400 Elizabeth Dr, Winter Park $2,580,000

Beautiful and secluded lakefront lot on quiet cove on Lake Osceola. Opportunity to design and Build with Z Properties.

Comstock Park SubDv.
32789 Zip Code

2156 Talman Court, Winter Park $2,495,000

Introducing a once-in-a-lifetime opportunity to own an exquisite multi-generational home in the coveted and exclusive neighborhood of Talman Mews, situated on not one, bu...

5 Beds
5.5 Baths
Talman Mews Ph 2 SubDv.
32792 Zip Code

1640 Mayfield Ave, Winter Park $1,725,000

Located in desirable Winter Park, this beautiful single-story home is situated on an oversized lot of 0.28 acres surrounded by mature oaks, magnolia and an array of lush ...

3 Beds
2.5 Baths
Temple Estates SubDv.
32789 Zip Code

4434 Glenview Lane, Winter Park $450,000

One or more photo(s) has been virtually staged. Have you been on the hunt for a First Home, Second Home, or Investment Home?? Look no further! This 4 bedroom, 2 bath, up...

4 Beds
2 Baths
Glenmoor SubDv.
32792 Zip Code

3114 Heartleaf Place, Winter Park $679,900

It is all about LOCATION, LOCATION, LOCATION!! This beautiful spacious Winter Park home is located in the Lost Creek subdivision, a very private community with no rear ne...

4 Beds
3 Baths
Lost Creek SubDv.
32792 Zip Code

7448 Aloma Avenue, Winter Park $1,100,000

Nice 5-tenant retail strip center.

Suburban Homes SubDv.
32792 Zip Code

1451 Lyndale Boulevard, Winter Park image

1451 Lyndale Boulevard, Winter Park $1,750,000

**YOUR SEARCH STOPS HERE** POOL HOME** SEPARATE TWO BEDROOM GUEST HOUSE** MASTER BEDROOM ON MAIN LEVEL** Experience luxury living at its finest in this beautiful two-stor...

5 Beds
3.5 Baths
Dixie Terrace SubDv.
32789 Zip Code

1321 Bridgeport Drive, Winter Park image

1321 Bridgeport Drive, Winter Park $759,900 ▼

Waterbridge of Winter Park! Rare opportunity to own in this fabulous Winter Park community being offered by the original owner. This one is ready for your special touch...

4 Beds
2 Baths
Waterbridge SubDv.
32789 Zip Code

2112 Sycamore Drive, Winter Park $625,000

Unbelievable opportunity to own this 4 bedroom, 3 bath home nestled within a charming and highly sought-after Winter Park neighborhood. This older home exudes timeless ap...

4 Beds
3 Baths
Northwood Terrace SubDv.
32789 Zip Code

627 Gilbert Road, Winter Park $599,999 ▼

Welcome to the Neighborhood! This stunning home is nestled in the desirable location of Winter Park Pines offering a perfect setting for both comfort and convenience. TON...

4 Beds
2 Baths
Winter Park Pines SubDv.
32792 Zip Code

Winter Park Real Estate Search

Address Search

Advanced Search

Map Search

Market Report

Winter Park Homes for Sale

Newest Winter Park Homes for Sale

Address Search

Central FL Real Estate by City

Central FL Real Estate by Neighborhood

Real Estate Market Reports

Interactive Map Search

Buying & Selling Made Easy

The Home Buying Process

Mortgage Calculator

Buyer Resources

Seller Resources

Connect With Us

Translate Site