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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

property image
1257 Wading Waters Circle, Winter Park $1,600,000

Welcome to luxury living in Hawks Crest, Winter Park’s only guard-gated community. This exceptional six-bedroom Del Rio floor plan sits on one of the neighborhood’s most ...

  • 6 Beds
  • 5 Baths
  • Waters Edge At Hawks Crest SubDv.
  • 32792 Zip Code
2136 Linden Road, Winter Park image
2136 Linden Road, Winter Park $365,000

Welcome home to Winter Park! This beautifully renovated 3-bedroom, 1.5-bath home offers the perfect combination of classic Florida living and extensive modern updates. Mu...

  • 3 Beds
  • 2 Baths
  • Ridge High Sub SubDv.
  • 32792 Zip Code
2873 Old Castle Drive, Winter Park image
2873 Old Castle Drive, Winter Park $1,395,000

Welcome to 2873 Old Castle Drive, an exceptional property located within the sought-after gated community of Bear Gully Pointe in Winter Park. Nestled along the shores o...

  • 4 Beds
  • 4 Baths
  • Bear Gully Pointe SubDv.
  • 32792 Zip Code
2122 Ridge Drive, Winter Park image
2122 Ridge Drive, Winter Park $360,000

Great investment opportunity in Winter Park. 4 bedroom 2.5 bathroom. Large covered patio overlooks huge completely fenced back yard. New roof 2025, HVAC system 2020, w...

  • 4 Beds
  • 3 Baths
  • Ridge High Sub SubDv.
  • 32792 Zip Code
3020 Nicholson Drive, Winter Park image
3020 Nicholson Drive, Winter Park $495,000

UPDATED 4-BEDROOM POOL HOME IN WINTER PARK WITH NO HOA! Welcome to 3020 Nicholson Drive, a beautifully updated 4-bedroom, 2-bath home with a private pool, 2-car garage, a...

  • 4 Beds
  • 2 Baths
  • Wrenwood Unit 3 3rd Add SubDv.
  • 32792 Zip Code
2211 King Richards Court, Winter Park image
2211 King Richards Court, Winter Park $549,000

Welcome to this beautifully updated 4-bedroom, 2-bath pool home located in the highly desirable Winter Woods community of Winter Park. From the moment you step inside, yo...

  • 4 Beds
  • 2 Baths
  • Winter Woods Unit 03 SubDv.
  • 32792 Zip Code
1445 Via Sangro Place, Winter Park image
1445 Via Sangro Place, Winter Park $1,350,000

Virtually Staged. Welcome to your dream home in the highly sought-after Lakeside Estates neighborhood in Winter Park! This elegant 6-bedroom, 5-bathroom, 2 laundry rooms ...

  • 6 Beds
  • 6 Baths
  • Lakeside Estates SubDv.
  • 32792 Zip Code
1117 Wading Waters Circle, Winter Park image
1117 Wading Waters Circle, Winter Park $1,325,000 ▼

Welcome to an exceptional opportunity in Waters Edge at Hawks Crest, one of Winter Park's premier gated, resort-style communities. Positioned on a desirable premium lot w...

  • 6 Beds
  • 4 Baths
  • Waters Edge At Hawks Crest SubDv.
  • 32792 Zip Code
2181 Linden Road, Winter Park image
2181 Linden Road, Winter Park $450,000

Welcome to 2181 Linden Road, where modern updates meet the everyday convenience of Winter Park living. Thoughtfully renovated and designed with flexibility in mind, this ...

  • 5 Beds
  • 3 Baths
  • Ridge High 1st Add SubDv.
  • 32792 Zip Code
2112 Eastbrook Boulevard, Winter Park image
2112 Eastbrook Boulevard, Winter Park $429,998

Welcome home to 2112 Eastbrook Blvd, a fully remodeled gem tucked into the sought-after Eastbrook neighborhood of Winter Park! This 3-bedroom, 2-bathroom home has been...

  • 3 Beds
  • 2 Baths
  • Eastbrook Sub Unit 8 SubDv.
  • 32792 Zip Code
1660 Gladiolas Drive, Winter Park image
1660 Gladiolas Drive, Winter Park $519,900 ▼

Updated Winter Park home with 2,047 sq ft of heated/cooled living space, a huge backyard, and NO HOA. This is an owner-updated home—not a flip—with quality improvements c...

  • 3 Beds
  • 2 Baths
  • Garden Lake Estates Unit 1 SubDv.
  • 32792 Zip Code
1287 Verdant Glade Place, Winter Park image
1287 Verdant Glade Place, Winter Park $745,000 ▼

Virtually Staged. Gated Community | Dual Primary Suites | Main-Level Living | Located in Winter Park’s gated Hawks Crest community, this two-story home pairs a spacio...

  • 4 Beds
  • 4 Baths
  • Meadows At Hawks Crest SubDv.
  • 32792 Zip Code
1842 Puritan Avenue, Winter Park image
1842 Puritan Avenue, Winter Park $419,000

Virtually Staged. Modern design , open concept layout , sleek quartz counter top , all new appliances, new luxury vinyl plank flooring, new lanai upgrade. This beautiful ...

  • 4 Beds
  • 2 Baths
  • Eastbrook Sub Unit 06 2nd Rep SubDv.
  • 32792 Zip Code
120 Longbranch Road, Winter Park image
120 Longbranch Road, Winter Park $860,000

Virtually Staged. Set on nearly an acre in Winter Park, this stately two-story home offers five bedrooms and three and a half bathrooms across more than 3,200 square feet...

  • 5 Beds
  • 4 Baths
  • Lake Ann Estates Unit 3 SubDv.
  • 32792 Zip Code
2286 Marsh Sedge Lane, Winter Park image
2286 Marsh Sedge Lane, Winter Park $770,000

Virtually Staged. Welcome to one of the most uniquely positioned homes in the highly sought-after gated community of Hawk’s Crest. This former Meritage model home sits on...

  • 4 Beds
  • 3 Baths
  • Preserve At Hawks Crest SubDv.
  • 32792 Zip Code
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"Having dealt with a number of Realtors over the years, I can honestly say that Lisa Scott provided an experience that was superior in every way. She ... more "
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Scott Realty Associates
1540 International Parkway, Suite 2000
Lake Mary, FL 32746

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Email: Lisa@ScottRealtyAssociates.com

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