+1(407) 304-7461 chad@dthomesteam.com
LPT Realty | Dreamtown Homes Team
  • Orlando Neighborhoods
    1. Audubon Park
    2. West Lakes District
    3. Parramore
    4. City District (Downtown)
    5. College Park
    6. Curry Ford West
    7. Gateway District
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    9. Mills 50
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WINTER GARDEN

Winter Garden is a charming and vibrant city known for its rich history and small-town atmosphere. Its historic downtown area, with brick-lined streets and preserved architecture, exudes a nostalgic charm. 

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MARKET SNAPSHOT FOR WINTER GARDEN

(MAY 11, 2026 - JUN 10, 2026)

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559 Properties

559 Properties for Sale In Winter Garden

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  • Baths (Most)
  • Beds (Most)
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FL >Winter Garden >
  • 17035 HARBOR OAK Pkwy, Winter Garden, FL 34787
    1/40 40
    New

    $499,999

    3 Beds2 Baths1,692 SqFt

    17035 HARBOR OAK Pkwy, Winter Garden, FL 34787

    Single Family Home

    Listed by Heidi Pfeffer-Morgan DALTON WADE INC

    Stellar MLS

    READ MORE

  • 3362 HANGING TIDE ST, Winter Garden, FL 34787
    3D
    New

    $929,000

    5 Beds5 Baths4,495 SqFt

    3362 HANGING TIDE ST, Winter Garden, FL 34787

    Single Family Home

    Listed by Drew Belani COMPASS FLORIDA LLC

    Stellar MLS

    READ MORE

  • 420 E CYPRESS ST, Winter Garden, FL 34787
    1/39 39
    New

    $425,000

    3 Beds2 Baths1,616 SqFt

    420 E CYPRESS ST, Winter Garden, FL 34787

    Single Family Home

    Listed by Trevor Zwick KELLER WILLIAMS ELITE PARTNERS III REALTY

    Stellar MLS

    READ MORE

  • 440 TIERRA VERDE LN, Winter Garden, FL 34787
    3D
    New

    $1,200,000

    4 Beds3 Baths3,512 SqFt

    440 TIERRA VERDE LN, Winter Garden, FL 34787

    Single Family Home

    Listed by Jerry Osser CHARLES RUTENBERG REALTY ORLANDO

    Stellar MLS

    READ MORE

  • 6100 CYPRESS HILL RD, Winter Garden, FL 34787
    1/51 51
    New

    $950,000

    5 Beds3 Baths3,777 SqFt

    6100 CYPRESS HILL RD, Winter Garden, FL 34787

    Single Family Home

    Listed by Crystal Taylor DALTON WADE INC

    Stellar MLS

    READ MORE

  • 9189 BUSACO PARK WAY, Winter Garden, FL 34787
    1/74 74
    New

    $1,300,000

    4 Beds4 Baths3,424 SqFt

    9189 BUSACO PARK WAY, Winter Garden, FL 34787

    Single Family Home

    Listed by Sulamit Sanchez COLDWELL BANKER REALTY

    Stellar MLS

    READ MORE

  • 13843 LANYARD WAY, Winter Garden, FL 34787
    1/34 34
    Active

    $648,000

    4 Beds4 Baths2,568 SqFt

    13843 LANYARD WAY, Winter Garden, FL 34787

    Single Family Home

    Listed by Jiu Wei AAA GLOBAL VENTURES PA

    Stellar MLS

    READ MORE

  • 2241 WHITE FEATHER LOOP, Winter Garden, FL 34787
    1/55 55
    Active

    $525,000

    3 Beds3 Baths2,152 SqFt

    2241 WHITE FEATHER LOOP, Winter Garden, FL 34787

    Single Family Home

    Listed by Brynn Allen CORCORAN PREMIER REALTY

    Stellar MLS

    READ MORE

  • 231 DOE RUN DR, Winter Garden, FL 34787
    1/47 47
    Active

    $500,000

    4 Beds2 Baths1,972 SqFt

    231 DOE RUN DR, Winter Garden, FL 34787

    Single Family Home

    Listed by Rick Coles THE C SMITH REAL ESTATE GROUP LLC

    Stellar MLS

    READ MORE

  • 5973 CYPRESS HILL RD, Winter Garden, FL 34787
    1/44 44
    Active

    $700,000

    5 Beds4 Baths3,532 SqFt

    5973 CYPRESS HILL RD, Winter Garden, FL 34787

    Single Family Home

    Listed by Michael Ellingson NEARBY REALTY

    Stellar MLS

    READ MORE

  • 6238 SUNNY TIME AVENUE, Winter Garden, FL 34787
    1/26 26
    Active

    $438,890

    3 Beds3 Baths1,683 SqFt

    6238 SUNNY TIME AVENUE, Winter Garden, FL 34787

    Townhouse

    Listed by Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

    Stellar MLS

    READ MORE

  • 181 ZACHARY WADE ST, Winter Garden, FL 34787
    1/65 65
    Active

    $600,000

    5 Beds3 Baths2,940 SqFt

    181 ZACHARY WADE ST, Winter Garden, FL 34787

    Single Family Home

    Listed by Ashley Boyd BHHS FLORIDA REALTY

    Stellar MLS

    READ MORE

  • 2120 GOPHER TORTOISE TER, Winter Garden, FL 34787
    1/33 33
    Active

    $379,900

    3 Beds3 Baths1,620 SqFt

    2120 GOPHER TORTOISE TER, Winter Garden, FL 34787

    Townhouse

    Listed by Andy Neal THE AGENCY FL

    Stellar MLS

    READ MORE

  • 6246 SUNNY TIME AVENUE, Winter Garden, FL 34787
    1/24 24
    Active

    $424,490

    3 Beds3 Baths1,553 SqFt

    6246 SUNNY TIME AVENUE, Winter Garden, FL 34787

    Townhouse

    Listed by Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

    Stellar MLS

    READ MORE

  • 11036 ROBERT FROST DR, Winter Garden, FL 34787
    1/34 34
    Active

    $649,990

    4 Beds3 Baths2,136 SqFt

    11036 ROBERT FROST DR, Winter Garden, FL 34787

    Single Family Home

    Listed by Rodrigo Khoury Francisco WRA BUSINESS & REAL ESTATE

    Stellar MLS

    READ MORE

  • 13181 TOOLCROSS WAY, Winter Garden, FL 34787
    1/87 87
    Active

    $1,100,000

    5 Beds4 Baths3,894 SqFt

    13181 TOOLCROSS WAY, Winter Garden, FL 34787

    Single Family Home

    Listed by Roberta do Nascimento Ferreira Voto FLORIDA CONNEXION PROPERTIES

    Stellar MLS

    READ MORE

  • 13822 JOMATT LOOP, Winter Garden, FL 34787
    1/37 37
    Active

    $1,000,000

    4 Beds4 Baths3,828 SqFt

    13822 JOMATT LOOP, Winter Garden, FL 34787

    Single Family Home

    Listed by Jenna Palmero COLDWELL BANKER REALTY

    Stellar MLS

    READ MORE

  • 13978 LANYARD WAY, Winter Garden, FL 34787
    1/57 57
    Open Wed 2PM-4PM

    $885,000

    5 Beds4 Baths3,687 SqFt

    13978 LANYARD WAY, Winter Garden, FL 34787

    Single Family Home

    Listed by Selby Turnbull EXP REALTY LLC

    Stellar MLS

    READ MORE

  • 15591 GENTLE RAIN DR, Winter Garden, FL 34787
    1/68 68
    Active

    $730,000

    5 Beds4 Baths2,896 SqFt

    15591 GENTLE RAIN DR, Winter Garden, FL 34787

    Single Family Home

    Listed by Carolina Fortes Ribeiro EMPIRE NETWORK REALTY

    Stellar MLS

    READ MORE

  • 16277 HONEY HARVEST ST, Winter Garden, FL 34787
    1/38 38
    Active

    $668,000

    4 Beds5 Baths2,930 SqFt

    16277 HONEY HARVEST ST, Winter Garden, FL 34787

    Single Family Home

    Listed by Jennifer Olmeda WRA BUSINESS & REAL ESTATE

    Stellar MLS

    READ MORE

  • 279 DOE RUN DR, Winter Garden, FL 34787
    1/35 35
    Open Sat 11AM-2PM

    $599,000

    3 Beds3 Baths2,435 SqFt

    279 DOE RUN DR, Winter Garden, FL 34787

    Single Family Home

    Listed by Jerry Cionci FLORIDA EXECUTIVE REALTY 2

    Stellar MLS

    READ MORE

  • 6279 SUNNY TIME AVENUE, Winter Garden, FL 34787
    1/28 28
    Active

    $546,490

    3 Beds3 Baths1,913 SqFt

    6279 SUNNY TIME AVENUE, Winter Garden, FL 34787

    Single Family Home

    Listed by Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

    Stellar MLS

    READ MORE

  • 8266 PURPLE SANDPIPER AVE, Winter Garden, FL 34787
    1/57 57
    Active

    $639,000

    4 Beds3 Baths2,274 SqFt

    8266 PURPLE SANDPIPER AVE, Winter Garden, FL 34787

    Single Family Home

    Listed by Thomas Nickley, Jr KELLER WILLIAMS REALTY AT THE PARKS

    Stellar MLS

    READ MORE

  • 10301 AUSTRINA OAK LOOP, Winter Garden, FL 34787
    1/23 23
    Active

    $530,000

    3 Beds3 Baths2,078 SqFt

    10301 AUSTRINA OAK LOOP, Winter Garden, FL 34787

    Single Family Home

    Listed by Rick Gradin OKKLA REALTY

    Stellar MLS

    READ MORE

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LPT Realty | Dreamtown Homes Team

Get My App

LPT Realty
Chad Gibson
+1(407) 304-7461
chad@dthomesteam.com

      Orlando Neighborhoods
      1. Audubon Park
      2. West Lakes District
      3. Parramore
      4. City District (Downtown)
      5. College Park
      6. Curry Ford West
      7. Gateway District
      8. Ivanhoe District
      9. Mills 50
      10. SODO
      11. The Milk District
      12. Thornton Park
      13. Baldwin Park
      14. The Packing District
      Cities
      1. Altamonte Springs
      2. Celebration
      3. Davenport
      4. Doctor Phillips
      5. Horizon West
      6. Hunter's Creek
      7. Kissimmee
      8. Lake Nona
      9. Maitland
      10. Orlando
      11. Sanford
      12. Winter Garden
      13. Winter Park
      Buy/Sell
      1. Search Listings
      2. Featured Listings
      3. Sell My Home
      4. Home Valuation
      News
      1. Living In Orlando
      2. Market Snapshot
      Contact Us
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.

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

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

LPT Realty | Dreamtown Homes Team

Get My App

LPT Realty
Chad Gibson
+1(407) 304-7461
chad@dthomesteam.com

      Orlando Neighborhoods
      1. Audubon Park
      2. West Lakes District
      3. Parramore
      4. City District (Downtown)
      5. College Park
      6. Curry Ford West
      7. Gateway District
      8. Ivanhoe District
      9. Mills 50
      10. SODO
      11. The Milk District
      12. Thornton Park
      13. Baldwin Park
      14. The Packing District
      Cities
      1. Altamonte Springs
      2. Celebration
      3. Davenport
      4. Doctor Phillips
      5. Horizon West
      6. Hunter's Creek
      7. Kissimmee
      8. Lake Nona
      9. Maitland
      10. Orlando
      11. Sanford
      12. Winter Garden
      13. Winter Park
      Buy/Sell
      1. Search Listings
      2. Featured Listings
      3. Sell My Home
      4. Home Valuation
      News
      1. Living In Orlando
      2. Market Snapshot
      Contact Us
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.

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

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