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Winter Park Real Estate Search

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Winter Park Homes for Sale

Winter Park, Florida, is a fantastic place to buy a home in the Orlando Metro Area of sunny Orange County. Home to nearly thirty thousand people, this charming community is known for its brick-lined streets, stately mature trees, lovely parks, and sparkling lakes. Initially chartered in 1887, it is a well-established community with a long history and rich heritage. Located just north of the excitement of Orlando, Winter Park offers proximity to big-city services, amenities, and attractions, as well as a relaxed, laid-back lifestyle. That said, you’ll find many wonderful options for shopping, dining, recreation, and entertainment in and around Winter Park, too.

Among the many advantageous features of Winter Park is Central Florida’s second oldest golf club and the Winter Park Historical Museum. Beyond these two destinations are many other options for recreation and entertainment. Furthermore, the community has numerous annual events, festivals, and holiday celebrations, including the Winter Park Sidewalk Art Festival, the Winter Park Autumn Art Festival, the Bach Festival Society of Winter Park, and the Florida Film Festival. Additionally, there are many exciting shopping and dining choices along Park Avenue and in other pockets of Winter Park.

Beyond all of these beneficial features, Winter Park real estate is also remarkable. Homes for sale in Winter Park can be found in numerous prestigious neighborhoods and subdivisions, such as Northwood Circle, Windsong, Plymouth Apartments, Green Oaks, Hannibal Square, College Quarter, and Orwin Manor. Real estate in Winter Park includes attached and detached properties to suit people in all seasons of life, whether young and single or married and retired, or somewhere in between. Winter Park homes are big and small, old and new, and in a wide variety of architectural styles. It would be our great pleasure to tell you all about the currently listed properties in Winter Park, Florida, so please connect with us as soon as it is convenient.

Our website features the best Winter Park real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in the Winter Park real estate market? Sign up for a Winter Park Real Estate Market Report to see what’s active, under contract, and sold!

Contact us today to find out how we can be of assistance to you!

Newest Winter Park Homes for Sale

1026 Manchester Circle, Winter Park image
1026 Manchester Circle, Winter Park $475,000

A must see Winter Park pool home w/ lovely open split plan. Enjoy spacious family room opening to covered rear porch and screened free form pool. Home features both a di...

  • 4 Beds
  • 2 Baths
  • Howell Estates Rep SubDv.
  • 32792 Zip Code
7577 Dockside Street, Winter Park image
7577 Dockside Street, Winter Park $389,500

Fully remodeled home in Winter Park with no association and huge backyard space. This three-bedroom, two-bath, one-car garage home has new laminate throughout the entire ...

  • 3 Beds
  • 2 Baths
  • Woodcrest Unit 6 SubDv.
  • 32792 Zip Code
3340 Balsam Dr, Winter Park image
3340 Balsam Dr, Winter Park $412,000

JACKPOT! NEW ROOF AND GUTTERS 2023! HVAC 2021!, Interior completely painted including garage floor 2023! $61,000 in improvements on this home since 2017. Move in ready! ...

  • 3 Beds
  • 2 Baths
  • Eastbrook Sub Unit 13 SubDv.
  • 32792 Zip Code
202 Longbranch Court, Winter Park image
202 Longbranch Court, Winter Park $850,000

This one of a kind Winter Park 4 bed/3.5 Pool contemporary two-story ranch estate is sure to impress! Sitting on nearly an acre in a secluded cul de sac makes this prope...

  • 4 Beds
  • 3.5 Baths
  • Lake Ann Estates Unit 3 SubDv.
  • 32792 Zip Code
1270 Gladiolas Drive, Winter Park image
1270 Gladiolas Drive, Winter Park $530,000

Located in the picturesque Winter Park area of Florida, this stunning home boasts an UNPARALLED LAKEVIEW and is surrounded by lush tropical forest landscaping, providing ...

  • 3 Beds
  • 2 Baths
  • Garden Lake Estates SubDv.
  • 32792 Zip Code
1901 Azalea Avenue, Winter Park image
1901 Azalea Avenue, Winter Park $324,700

Peaceful Florida living awaits in this Super Sweet Winter Park Two Bedroom, One Bath, home on a Tree Covered Corner Lot. Bonus Room could be an Office or Extra Bedroom. O...

  • 2 Beds
  • 1 Baths
  • Temple Terrace Annex SubDv.
  • 32792 Zip Code
1489 Lone Feather Trail, Winter Park image
1489 Lone Feather Trail, Winter Park $799,900 ▲

Stunning new two-story home in Winter Park’s exclusive gated community of Hawk’s Crest. This 4-bedroom, 3 bathroom home has a great floor plan that features open dining a...

  • 4 Beds
  • 3.5 Baths
  • Landings At Hawks Crest SubDv.
  • 32792 Zip Code
1420 Lake Florence Way, Winter Park image
1420 Lake Florence Way, Winter Park $840,000 ▼

This 5 bd/4.5 ba, in this beautiful, GATED intimate community of 28 Lots. There is a community dock, perfect for launching a canoe, paddle board or just sitting and watch...

  • 5 Beds
  • 4.5 Baths
  • Lake Florence Preserve SubDv.
  • 32792 Zip Code
5347 N Orange Avenue, Winter Park image
5347 N Orange Avenue, Winter Park $375,000

First time on the market this wonderful 4 bedroom 2 bath home has been lovingly maintained by its' original owner. Light and bright this home offers 3 sliding glass doors...

  • 4 Beds
  • 2 Baths
  • Suburban Homes SubDv.
  • 32792 Zip Code
1944 Houndslake Drive, Winter Park image
1944 Houndslake Drive, Winter Park $400,000 ▼

Enjoy the convenient central location of the Winter Park home. From the moment you walk in, the Family Room greets you with vaulted ceilings, a floor-to-ceiling stone fir...

  • 3 Beds
  • 2 Baths
  • Cedar Ridge Unit 1 SubDv.
  • 32792 Zip Code
1796 E Cheryl Drive, Winter Park image
1796 E Cheryl Drive, Winter Park $449,900

STOP THE CAR, you do not want to miss this Beautifully Renovated Carolyn Estates Home that has just HIT THE MARKET! The Home Features 3 bedrooms, 2 baths and almost 2,000...

  • 3 Beds
  • 2 Baths
  • Carolyn Estates SubDv.
  • 32792 Zip Code
210 Laurel Park Court, Winter Park image
210 Laurel Park Court, Winter Park $1,100,000

Welcome home to this luxury custom-built home by award-winning Arthur Rutenberg Homes. Featuring 9'-12' ceilings w/ 4 bedrooms, 3 bathrooms and a private office. This gor...

  • 4 Beds
  • 3 Baths
  • Sanctuary At Lake Ann SubDv.
  • 32792 Zip Code
1416 Aster Court, Winter Park image
1416 Aster Court, Winter Park $539,990 ▲

Back to Active. Buyer wasn't able to secure financing. Completely remodeled 5 bedrooms and 3 bathroom pool home on an oversized lot. As you walk in the front door you...

  • 5 Beds
  • 3 Baths
  • Garden Lake Estates Unit 3 SubDv.
  • 32792 Zip Code
4464 Tuscany Island Court, Winter Park image
4464 Tuscany Island Court, Winter Park $1,500,000 ▼

Enjoy the Winter Park lifestyle. Your dream home, a stunning Tuscan style residence with 4,625 SqFt of spacious living is tucked away in a quiet gated community of only f...

  • 4 Beds
  • 4.5 Baths
  • Tuscany Island SubDv.
  • 32792 Zip Code
4400 Tuscany Island Court, Winter Park image
4400 Tuscany Island Court, Winter Park $3,950,000 ▼

Welcome to Tuscany Island in Winter Park! Private gated enclave of 5 magnificent luxury estate homes, resting on the lake shore of Bear Gulley. This highly sought-after a...

  • 4 Beds
  • 5.5 Baths
  • Tuscany Island SubDv.
  • 32792 Zip Code
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1540 International Parkway, Suite 2000
Lake Mary, FL 32746

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