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
468 Properties

468 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
  • 457 E NEW ENGLAND AVE, Winter Park, FL 32789
    1/30 30
    Pending

    $ 3,100,000

    5 Beds5 Baths3,847 SqFt

    457 E NEW ENGLAND 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
  • 1860 VIA CONTESSA, Winter Park, FL 32789
    1/90 90
    Open Sun 11AM-2PM

    $ 2,875,000

    8 Beds6 Baths7,000 SqFt

    1860 VIA CONTESSA, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 700 JACKSON AVE, Winter Park, FL 32789
    1/41 41
    Pending

    $ 2,795,000

    10,174 SqFt

    700 JACKSON AVE, Winter Park, FL 32789

    Commercial

    Listed by

    Stellar MLS
  • 2550 VENETIAN WAY, Winter Park, FL 32789
    1/34 34
    Active

    $ 2,599,000

    4 Beds5 Baths4,875 SqFt

    2550 VENETIAN WAY, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1661 PALM AVENUE, Winter Park, FL 32789
    1/41 41
    Open Sun 2PM-4PM

    $ 2,598,000

    4 Beds6 Baths3,570 SqFt

    1661 PALM AVENUE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 185 SYLVAN BLVD, Winter Park, FL 32789
    1/10 10
    Pending

    $ 2,590,000

    4 Beds5 Baths3,138 SqFt

    185 SYLVAN BLVD, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 450 LAKEWOOD DR, Winter Park, FL 32789
    1/87 87
    Active

    $ 2,500,000

    5 Beds6 Baths4,676 SqFt

    450 LAKEWOOD DR, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 140 E MORSE BLVD #J, Winter Park, FL 32789
    1/32 32
    Active

    $ 2,495,000

    3 Beds3 Baths2,143 SqFt

    140 E MORSE BLVD #J, Winter Park, FL 32789

    Condo

    Listed by

    Stellar MLS
  • 1602 ALABAMA DR #PH404, Winter Park, FL 32789
    1/70 70
    Pending

    $ 2,490,000

    3 Beds4 Baths2,709 SqFt

    1602 ALABAMA DR #PH404, Winter Park, FL 32789

    Condo

    Listed by

    Stellar MLS
  • 1268 PRESERVE POINT DR, Winter Park, FL 32789
    1/36 36
    Pending

    $ 2,350,000

    4 Beds4 Baths4,315 SqFt

    1268 PRESERVE POINT DR, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1781 PINE AVE, Winter Park, FL 32789
    1/99 99
    Pending

    $ 2,279,000

    5 Beds5 Baths3,882 SqFt

    1781 PINE 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
  • 922 N PENNSYLVANIA AVE, Winter Park, FL 32789
    1/39 39
    Open 11/1 12PM-2PM

    $ 2,195,000

    3 Beds4 Baths3,440 SqFt

    922 N PENNSYLVANIA AVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 2001 LAKE DR, Winter Park, FL 32789
    1/66 66
    Open Sat 12PM-2PM

    $ 2,190,000

    5 Beds4 Baths4,798 SqFt

    2001 LAKE DR, 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
  • 785 N PHELPS AVE, Winter Park, FL 32789
    1/11 11
    Active

    $ 2,119,000

    5 Beds4 Baths2,964 SqFt

    785 N PHELPS AVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1540 PALM AVE, Winter Park, FL 32789
    1/58 58
    Active

    $ 2,100,000

    5 Beds4 Baths3,423 SqFt

    1540 PALM AVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1451 LYNDALE BLVD, Winter Park, FL 32789
    1/89 89
    Active

    $ 1,999,993

    6 Beds4 Baths3,853 SqFt

    1451 LYNDALE BLVD, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1560 WOODLAND AVE, Winter Park, FL 32789
    1/48 48
    Open Sun 12PM-3PM

    $ 1,999,000

    5 Beds5 Baths3,851 SqFt

    1560 WOODLAND AVE, Winter Park, FL 32789

    Single Family Home

    Listed by

    Stellar MLS
  • 1612 MAGNOLIA AVE, Winter Park, FL 32789
    1/56 56
    Pending

    $ 1,995,000

    4 Beds5 Baths3,153 SqFt

    1612 MAGNOLIA AVE, 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
  • 319 SANTIAGO DR, Winter Park, FL 32789
    1/44 44
    Active

    $ 1,990,000

    4 Beds5 Baths3,515 SqFt

    319 SANTIAGO DR, 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
  • 1
  • 2
  • 3
  • 4
  • 5
  • ...
  • 20

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.