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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

2737 Bright Bird Lane, Winter Park image

2737 Bright Bird Lane, Winter Park — 17 $502,790

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

2100 Lake Drive, Winter Park $2,275,000

Offered at $2,275,000 - 2100 Lake Drive, Winter Park. Enjoy panoramic lakefront views from the privacy of your own home with this remarkable single-story lakefront reside...

4 Beds
3.5 Baths
Killarney Point SubDv.
32789 Zip Code

140 E Morse Boulevard Unit J, Winter Park image

140 E Morse Boulevard Unit J, Winter Park — The Landmark $3,990,000

COVETED FRONT CORNER PENTHOUSE RESIDENCE NOW AVAILABLE! THE LANDMARK IS AN AWARD WINNING LUXURY CONDO BUILDING IN DOWNTOWN WINTER PARK. AN AMAZING LARGE PRIVATE BALCONY, ...

3 Beds
3 Baths
Landmark Winter Park Condo SubDv.
32789 Zip Code

3437 Bowman Drive, Winter Park $450,000

Just like new! This home has recently under gone through complete updating. Newer roof and widows. Completely new kitchen, updated bathrooms, refinished flooring, new lan...

3 Beds
2 Baths
Eastbrook Sub Unit 12 SubDv.
32792 Zip Code

518 W Swoope Avenue, Winter Park — Vilasa Ttownhomes $1,625,000

ENJOY LUXURY AND MAINTENANCE FREE LIVING WITH PREMIUM WINTER PARK LOCATION IN THIS VILASA TOWNHOME! OWNER IS RELOCATING AFTER SPARING NO EXPENSE FOR HIGH-END UPGRADES, AD...

3 Beds
2.5 Baths
Vilasa Twnhms SubDv.
32789 Zip Code

5535 Garden Grove Circle, Winter Park image

5535 Garden Grove Circle, Winter Park $432,900

Amazing pool home completely updated inside and out, near excellent schools. Contact Chad Shultz for any and all questions regarding this property. Get a look before this...

3 Beds
2 Baths
Garden Grove SubDv.
32792 Zip Code

3077 Nicholson Drive, Winter Park $429,900

This stunning property is the epitome of convenience, offering you a lifestyle that's second to none. With its prime location, this home is move-in ready and perfectly si...

4 Beds
3 Baths
Howell Branch Woods SubDv.
32792 Zip Code

1252 Valley Creek Run, Winter Park image

1252 Valley Creek Run, Winter Park $850,000

Extremely rare opportunity to own a fully updated CONTEMPORARY MASTERPIECE in the heart of Seminole County, FL!! Meticulous maintenance and pride of ownership is obvious...

5 Beds
3 Baths
Lost Creek SubDv.
32792 Zip Code

1405 Green Cove Road, Winter Park $2,995,000

This exquisite residence features four spacious bedrooms, three and a half luxurious bathrooms, a convenient 2-car side-entry garage. Renovated from the ground up by Skol...

4 Beds
3.5 Baths
Camwood Sub SubDv.
32789 Zip Code

5324 Poinsetta Avenue, Winter Park image

5324 Poinsetta Avenue, Winter Park $495,000

Excellent primary residence with an income opportunity or two rental units in one! The main home is a spacious 3/2 with recently upgraded bathrooms and partial kitchen u...

5 Beds
3 Baths
Wrenwood Heights Unit 2 SubDv.
32792 Zip Code

1710 Winter Park Road, Winter Park image

1710 Winter Park Road, Winter Park $775,000

Move in ready 3 bedroom 2 bath Winter Park home located in the Audubon K-8 and Winter Park High district. This renovated and updated home has beautiful wood flooring, a l...

3 Beds
2 Baths
Charmont SubDv.
32789 Zip Code

1721 Brazilian Lane, Winter Park $399,000

One or more photo(s) has been virtually staged. Welcome to 1721 Brazilian Lane! This turn-key home is ready for its new owner! Equipped with PAID OFF State of the Art Sol...

3 Beds
2 Baths
Eastbrook Sub Unit 06 2nd Rep SubDv.
32792 Zip Code

1550 Drum Street, Winter Park $350,000

This is a great opportunity to purchase a vacant lot in Winter Park 32789, zoned for Dommerich Elementary, Maitland Middle School, and Winter Park School. Lot dimensions ...

Winter Park Manor SubDv.
32789 Zip Code

2852 Sheriff Way, Winter Park $724,900

Welcome to this meticulously renovated 4-bedroom, 3-bathroom home, complete with an office/den. Every corner of this residence has been thoughtfully redesigned. The kitch...

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

1531 Sunset Drive, Winter Park $1,195,000

Charming custom-built, two-story transitional home exudes warmth and character from the moment you step inside. Located on a beautiful, quiet, tree-lined Winter Park bric...

4 Beds
2.5 Baths
Lake Knowles Terr SubDv.
32789 Zip Code

1523 Berkshire Avenue, Winter Park image

1523 Berkshire Avenue, Winter Park $495,000

Location, Location, Location. This is a cute 3 bedroom 1 1/2 bathroom house located in 32789 part of Orwin Manor subdivision of beautiful Winter Park. The home is charmi...

3 Beds
1.5 Baths
Orwin Manor Westminster Sec SubDv.
32789 Zip Code

654 W Morse Boulevard, Winter Park image

654 W Morse Boulevard, Winter Park $7,600,000

Distinctive, inspirational & harmonious. This newly constructed contemporary estate was designed by internationally respected architect, Kamal Rizk. The unique fusion of ...

5 Beds
7.5 Baths
Morse & Pennsylvania Twnhms SubDv.
32789 Zip Code

140 E Morse Boulevard Unit I, Winter Park image

140 E Morse Boulevard Unit I, Winter Park — The Landmark $2,399,000

HERE IS ANOTHER OPPORTUNITY TO OWN A UNIT IN THE LANDMARK BUILDING IN THE HEART OF DOWNTOWN WINTER PARK. This stunning 3 BEDROOM, 2 BATH unit has recently been UPDATED i...

3 Beds
2 Baths
Landmark Winter Park SubDv.
32789 Zip Code

102 S Interlachen Avenue Unit 510, Winter Park image

102 S Interlachen Avenue Unit 510, Winter Park — 102 $575,000

Nestled in between the Winter Park Chain of Lakes and Park Avenue, this stunning condominium offers the perfect blend of elegance and convenience, making it an ideal dwel...

2 Beds
1 Baths
Cloisters Condo SubDv.
32789 Zip Code

2079 Laurelwood Way, Winter Park $825,000

Nestled in the heart of Winter Park's finest gated community awaits your modern masterpiece. Perfectly positioned on a corner lot and spanning over 2,100 square feet of e...

4 Beds
3 Baths
Preserve At Hawks Crest SubDv.
32792 Zip Code

1921 Englewood Road, Winter Park $1,279,000

Mid Century Modern home with Craftsman style finishes perfect for the car enthusiast minutes from downtown Park Avenue. Single story ranch features soaring ceilings, lar...

3 Beds
2.5 Baths
Forest Hills SubDv.
32789 Zip Code

600 Maiden Lane, Winter Park $1,845,000

Perched high on a corner lot, nestled between Bonita Dr. and Bryan Ave., along the brick streets of Winter Park, this .34 acre property is truly a little slice of private...

4 Beds
4.5 Baths
Comstock Park SubDv.
32789 Zip Code

730 W Swoope Ave Avenue, Winter Park image

730 W Swoope Ave Avenue, Winter Park $690,000

One or more photo(s) has been virtually staged. Unearth Winter Park's Hidden Gem! Nestled just 3 short blocks from the vibrant Park Ave, this spacious 2200+ sqft home awa...

5 Beds
3 Baths
Carver Town First Add SubDv.
32789 Zip Code

3197 Crown Jewel Court, Winter Park image

3197 Crown Jewel Court, Winter Park — Na $360,000

Beautiful and like-new 3 beds, 2.5 baths townhome located in Winter Park! Zoned for prestigious Winter Park A++ rated public schools, this unit has fresh paint and comes ...

3 Beds
2.5 Baths
Coronado Townhomes SubDv.
32792 Zip Code

7384 Grand Avenue, Winter Park $405,880

This is your new home Winter Park ! Move in condition, large fenced backyard with patio and deck. New doors new windows, new paint.. this home is move in ready.. Open p...

3 Beds
2 Baths
Oakcrest-516 SubDv.
32792 Zip Code

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