Dowling, Amerivest Pro-Team Philip and Perrine Dowling, Realtors
  • Central Living
    1. Sanford Florida
    2. Eustis, Florida
    3. Mount Dora
    4. Orlando
    5. Tavares
    6. Winter Park
  • Coastal Living
    1. Daytona Beach
    2. Edgewater
    3. New Smyrna Beach
    4. Ponce Inlet
    5. Ormond Beach
    6. Palm Coast
    7. Gulf Of America Homes
  • Meet The Dowlings
  • Register
  • /
  • Sign In
Filters Reset
Save Search (2)
Save your search to get Alerts
109 Properties

109 Properties Available In Winter Park

  • Price-High To Low
  • Newest Listings
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
FL >Winter Park >
Market Insights
  • 887 GEORGIA AVE, Winter Park, FL 32789
    1/51 51
    Active

    $ 5,900,000

    6 Beds6 Baths5,759 SqFt

    887 GEORGIA AVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1161 VALENCIA AVE, Winter Park, FL 32789
    1/66 66
    Active

    $ 4,545,000

    4 Beds5 Baths4,181 SqFt

    1161 VALENCIA AVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1820 GLENCOE RD, Winter Park, FL 32789
    1/75 75
    Open Sun 12PM-2PM

    $ 3,825,000

    5 Beds7 Baths4,055 SqFt

    1820 GLENCOE RD, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1742 TEMPLE DR, Winter Park, FL 32789
    1/58 58
    Active

    $ 3,600,000

    4 Beds5 Baths3,658 SqFt

    1742 TEMPLE DR, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 255 STIRLING AVE, Winter Park, FL 32789
    1/53 53
    Pending

    $ 3,100,000

    4 Beds4 Baths3,635 SqFt

    255 STIRLING AVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 541 W CANTON AVE, Winter Park, FL 32789
    1/49 49
    Active

    $ 2,935,000

    4 Beds4 Baths3,553 SqFt

    541 W CANTON AVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 2015 N PARK AVE, Winter Park, FL 32789
    1/64 64
    Active

    $ 2,495,000

    5 Beds5 Baths3,963 SqFt

    2015 N PARK AVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 715 VIA BELLA, Winter Park, FL 32789
    1/60 60
    Active

    $ 2,219,000

    5 Beds4 Baths4,328 SqFt

    715 VIA BELLA, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 640 ARJAY WAY, Winter Park, FL 32789
    1/99 99
    Active

    $ 2,150,000

    5 Beds5 Baths3,930 SqFt

    640 ARJAY WAY, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1752 CHESTNUT AVE, Winter Park, FL 32789
    1/64 64
    Active

    $ 1,995,000

    4 Beds5 Baths3,314 SqFt

    1752 CHESTNUT AVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 2614 PARKLAND DR, Winter Park, FL 32789
    1/56 56
    Active

    $ 1,950,000

    4 Beds4 Baths3,307 SqFt

    2614 PARKLAND DR, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1710 ONECO AVE, Winter Park, FL 32789
    1/47 47
    Active

    $ 1,945,000

    5 Beds5 Baths3,174 SqFt

    1710 ONECO AVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1840 BRYAN AVE, Winter Park, FL 32789
    1/47 47
    Active

    $ 1,899,500

    4 Beds4 Baths3,727 SqFt

    1840 BRYAN AVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 340 ALBERTA DR, Winter Park, FL 32789
    1/70 70
    Active

    $ 1,598,000

    4 Beds4 Baths3,226 SqFt

    340 ALBERTA DR, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1780 MIZELL AVE., Winter Park, FL 32789
    1/59 59
    Open Sun 3PM-5PM

    $ 1,595,000

    4 Beds4 Baths2,743 SqFt

    1780 MIZELL AVE., Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1306 LINDENWOOD LN, Winter Park, FL 32792
    1/50 50
    Open Sat 12PM-3PM

    $ 1,499,000

    4 Beds5 Baths3,726 SqFt

    1306 LINDENWOOD LN, Winter Park, FL 32792

    Single Family Home

    Listed by

    Stellar MLS
  • 1429 CHAPMAN CIR, Winter Park, FL 32789
    1/36 36
    Active

    $ 1,374,950

    4 Beds4 Baths3,116 SqFt

    1429 CHAPMAN CIR, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1400 S PENNSYLVANIA AVE, Winter Park, FL 32789
    1/50 50
    Active

    $ 1,250,000

    4 Beds3 Baths2,310 SqFt

    1400 S PENNSYLVANIA AVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1981 BLUE RIDGE RD, Winter Park, FL 32789
    1/51 51
    Active

    $ 1,230,000

    4 Beds2 Baths2,750 SqFt

    1981 BLUE RIDGE RD, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 100 S INTERLACHEN AVE #404, Winter Park, FL 32789
    1/52 52
    Active

    $ 1,195,000

    2 Beds2 Baths1,220 SqFt

    100 S INTERLACHEN AVE #404, Winter Park, FL 32789

    Condo

    Listed by

    Stellar MLS
  • 1341 LYNDALE BLVD, Winter Park, FL 32789
    1/45 45
    Active

    $ 1,130,000

    4 Beds3 Baths2,388 SqFt

    1341 LYNDALE BLVD, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 208 BREWER AVE, Winter Park, FL 32789
    1/47 47
    Active

    $ 950,000

    4 Beds4 Baths2,173 SqFt

    208 BREWER AVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 250 CORTLAND AVE, Winter Park, FL 32789
    1/68 68
    Active

    $ 950,000

    3 Beds2 Baths2,114 SqFt

    250 CORTLAND AVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 2129 FOSGATE DRIVE, Winter Park, FL 32789
    1/49 49
    Pending

    $ 935,000

    3 Beds3 Baths2,515 SqFt

    2129 FOSGATE DRIVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1
  • 2
  • 3
  • 4
  • 5

explore listings in Winter Park

  • Open House
  • Price Reduced
  • Virtual Tour
  • 3D Tour
Amerivest-Logo-ALL-White-991x547
Real Broker, LLC

Philip & Perrine Dowling License ID: 3090595

+1(239) 537-3332 perrine@dowlingteam.com

411 N Donnelly St, Mt Dora, FL, 32757, USA

Copyright 2023. All Rights Reserved.

    • Central Living
      1. Sanford Florida
      2. Eustis, Florida
      3. Mount Dora
      4. Orlando
      5. Tavares
      6. Winter Park
    • Coastal Living
      1. Daytona Beach
      2. Edgewater
      3. New Smyrna Beach
      4. Ponce Inlet
      5. Ormond Beach
      6. Palm Coast
      7. Gulf Of America Homes
    • Meet The Dowlings

Get My App

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

      Get access to off Market Homes!

Free Report

      Get access to off Market Homes!

Free Report

 

 

Explore Florida Towns &  Areas 

 

Mount Dora
Search Mount Dora Florida Homes
Tavares
Search Tavares Florida Homes
Eustis
Search Eustis Florida Homes
Winter Park
Search Winter Park Florida Homes
Winter Garden
Search home in Winter Garden
Orlando
Amerivest-Logo-ALL-White-991x547
Real Broker, LLC

Philip & Perrine Dowling License ID: 3090595

+1(239) 537-3332 perrine@dowlingteam.com

411 N Donnelly St, Mt Dora, FL, 32757, USA

Copyright 2023. All Rights Reserved.

    • Central Living
      1. Sanford Florida
      2. Eustis, Florida
      3. Mount Dora
      4. Orlando
      5. Tavares
      6. Winter Park
    • Coastal Living
      1. Daytona Beach
      2. Edgewater
      3. New Smyrna Beach
      4. Ponce Inlet
      5. Ormond Beach
      6. Palm Coast
      7. Gulf Of America Homes
    • Meet The Dowlings

Get My App

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.