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Winter Park is one of Central Florida's oldest and eclectic cities boasting a population of approximately 27,852 (2010 U.S. Census). The city was founded as a resort community by northern business magnates in the late 19th and early 20th Centuries. 

Winter Park is most well known for it's main street (Park Ave.) which includes civic buildings, art galleries, retail shops, museums, a park, train station, country club, historic cemetery, and a world renowned Private College in Rollins College.

109 S Ranger Boulevard, Winter Park image
109 S Ranger Boulevard, Winter Park $350,000

WINTER PARK LIVING LIKE YOU’VE NEVER EXPERIENCED! In this 3 bedroom, 2 bathroom home, you’ll love what this family residence has in store. Offering an oversized living ro...

  • 3 Beds
  • 2 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
804 Hamilton Place Court, Winter Park image
804 Hamilton Place Court, Winter Park $749,000

WOW!!! 804 Hamilton Place Court, Winter Park Fl. 32789 has many upgrades that will truly impress your buyers. Kitchen features upgraded cabinets and appliances, granite ...

  • 4 Beds
  • 4.5 Baths
  • Hamilton Place SubDv.
  • 32789 Zip Code
1811 Bryan Avenue, Winter Park image
1811 Bryan Avenue, Winter Park $1,139,000

This exceptional home, Completed in 2019 by Malak Corporation. This New Construction Features 4 bedrooms, 3.5 baths, an office, and additional study or flex room, all in ...

  • 4 Beds
  • 3.5 Baths
  • Lakeview Terrace SubDv.
  • 32789 Zip Code
1675 Dale Avenue, Winter Park image
1675 Dale Avenue, Winter Park $370,000

Charming, immaculate, adorable, updated home in prime Winter Park neighborhood among million dollar homes. This beautiful home boasts a luscious 40" tropical lap pool, wi...

  • 2 Beds
  • 1 Baths
  • Comstock Park SubDv.
  • 32789 Zip Code
1598 Michigan Avenue, Winter Park image
1598 Michigan Avenue, Winter Park $399,900

Rare find as many opportunities await on this multifamily corner home site in desirable Winter Park Location!!! Existing Solid block duplex with tremendous potential alre...

  • 6 Beds
  • 3 Baths
  • Lawndale SubDv.
  • 32789 Zip Code
1598 Michigan Avenue, Winter Park image
1598 Michigan Avenue, Winter Park $399,900

Rare find as many opportunities await on this multifamily corner home site in desirable Winter Park Location!!! Existing Solid block duplex with tremendous potential alre...

  • Lawndale SubDv.
  • 32789 Zip Code
1372 Heavenly Cove, Winter Park image
1372 Heavenly Cove, Winter Park $479,000

Here is your opportunity to own the beautiful and award winning “JACKSON” floorpan! Located in EDEN POINT, an exclusive and intimate gated community with a WINTER PARK ad...

  • 4 Beds
  • 2.5 Baths
  • Eden Point SubDv.
  • 32792 Zip Code
2890 Naples Drive, Winter Park image
2890 Naples Drive, Winter Park $300,000

LOCATION IS EVERYTHING! Don’t miss out on your opportunity to buy in this charming neighborhood. Tucked away from the hustle and bustle, this 4 bed-room, 2 bath home is m...

  • 4 Beds
  • 2 Baths
  • Fairbanks Shores 5th Add SubDv.
  • 32789 Zip Code
2827 Sanbina Street, Winter Park image
2827 Sanbina Street, Winter Park $359,900

This Winter Park three-bedroom two-bathroom home was built in 1962. It features concrete block construction, with stylish terrazzo floors. Located in the quiet neighborho...

  • 3 Beds
  • 2 Baths
  • Howell Heights SubDv.
  • 32789 Zip Code
5255 Pine Lily Circle, Winter Park image
5255 Pine Lily Circle, Winter Park $435,000

DIRECT POND VIEW. Welcome to Sanctuary at Aloma's gated community, on a quiet private cul-de-sac. This immaculately kept open concept one story home with split floor p...

  • 3 Beds
  • 2 Baths
  • Sanctuary At Aloma SubDv.
  • 32792 Zip Code
631 W Swoope Avenue, Winter Park image
631 W Swoope Avenue, Winter Park $649,000

NEW CONSTRUCTION!! This STUNNING HOME has ALL the BELLS and WISTLES!!! Located in the HEART OF WINTER PARK and within walking distance to WINTER PARK VILLAGE, HANNIBAL S...

  • 4 Beds
  • 2.5 Baths
  • Carver Town SubDv.
  • 32789 Zip Code
540 Shepherd Avenue, Winter Park image
540 Shepherd Avenue, Winter Park $1,695,000

Absolutely gorgeous new listing in Winter Park. Custom built in 2013 this stunning 4 bedroom, 4 ½ bath home features luxurious finishes throughout & an amazing floorplan ...

  • 4 Beds
  • 4.5 Baths
  • Ethel Park SubDv.
  • 32789 Zip Code
702 Driver Avenue, Winter Park image
702 Driver Avenue, Winter Park $599,000

Southern Charm at its best! Spectacular Custom Remodeled Winter Park/College Park home with separate Guest suite! Area is known for it's historic lakes, shops, & trendy r...

  • 5 Beds
  • 4.5 Baths
  • Dubsdread Heights SubDv.
  • 32789 Zip Code
662 Osceola Avenue Unit 2, Winter Park image
662 Osceola Avenue Unit 2, Winter Park — 662 $1,150,000

Lake front living with the lock and leave lifestyle...this beautiful 2290 square feet condo has great views of Lake Virginia...it is the gated Perle Du Lac community...th...

  • 3 Beds
  • 3.5 Baths
  • Perle Du Lac SubDv.
  • 32789 Zip Code
218 Orange Terrace Drive, Winter Park image
218 Orange Terrace Drive, Winter Park $350,000

Retaining the charm of mid-century Winter Park, this lovely historic pool home complete with wood floors, easy and elegant layout and ample off street parking is waiting ...

  • 3 Beds
  • 2 Baths
  • Orange Terrace SubDv.
  • 32789 Zip Code
1109 Wading Waters Circle, Winter Park image
1109 Wading Waters Circle, Winter Park — Meritage Homes $580,625

Under Construction. "Under Construction" Brand NEW energy-efficient home ready July 2019! The Palermo II is a one-story home featuring tile roofing, 3 car garage, extende...

  • 4 Beds
  • 3 Baths
  • Hawk's Crest SubDv.
  • 32792 Zip Code
1216 Verdant Glade, Winter Park image
1216 Verdant Glade, Winter Park $479,109

Under Construction. UNDER CONSTRUCTION. This sought after community in Winter Park will feature resort style amenities and private access to Lake Howell via a canoe launc...

  • 4 Beds
  • 3.5 Baths
  • Meadows At Hawks Crest SubDv.
  • 32792 Zip Code
1240 Woodmere Drive, Winter Park image
1240 Woodmere Drive, Winter Park $1,499,000

This lovely 3 bedroom, 2 1/2 bath home in the charming Via's of Olde Winter Park offers gracious living with warm casual elegance. Bright and cheerful large eat in kitche...

  • 3 Beds
  • 2.5 Baths
  • Woodmere Terrace Rep SubDv.
  • 32789 Zip Code
1821 Carollee Lane, Winter Park image
1821 Carollee Lane, Winter Park $495,000

This Winter Park home is a Must See! Neutral décor and updates make this home move in ready. The living area is bright and open, and can be flexible to your lifestyle. Th...

  • 3 Beds
  • 2.5 Baths
  • Green Terrace SubDv.
  • 32789 Zip Code
208 Brewer Avenue, Winter Park image
208 Brewer Avenue, Winter Park $614,900

Warm and elegant home in the heart of Winter Park just blocks away from Park Avenue, Rollins College, and across the street from Trismen Park. This completely remodeled 4...

  • 4 Beds
  • 3.5 Baths
  • Cortland Park SubDv.
  • 32789 Zip Code

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