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302 Properties
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302 Properties Available

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  • Price-High To Low
  • Price-Low To High
  • Newest Listings
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
  • 1327 BRIDGEPORT DR, Winter Park, FL 32789
    5 Beds4 Baths4,181 SqFt
    1/48 48
    Price Dropped by $100K

    $1,499,000

    1327 BRIDGEPORT DR, Winter Park, FL 32789

    Listed by RE/MAX TOWN & COUNTRY REALTY

    Stellar MLS
  • 1420 PALMER AVE, Winter Park, FL 32789
    4 Beds4 Baths2,953 SqFt
    1/47 47
    Price Dropped by $54K

    $1,395,000

    1420 PALMER AVE, Winter Park, FL 32789

    Listed by KELLER WILLIAMS WINTER PARK

    Stellar MLS
  • 240 CAMBRIDGE BLVD, Winter Park, FL 32789
    3 Beds2 Baths1,630 SqFt
    1/23 23
    Price Dropped by $10K

    $549,000

    240 CAMBRIDGE BLVD, Winter Park, FL 32789

    Listed by REAL BROKER, LLC

    Stellar MLS
  • 1112 PRESERVE POINT DR, Winter Park, FL 32789
    5 Beds6 Baths6,502 SqFt
    1/88 88
    Active

    $8,500,000

    1112 PRESERVE POINT DR, Winter Park, FL 32789

    Listed by KELLY PRICE & COMPANY LLC

    Stellar MLS
  • 1581 FOREST AVE, Winter Park, FL 32789
    4 Beds6 Baths4,683 SqFt
    1/44 44
    Active

    $4,175,000

    1581 FOREST AVE, Winter Park, FL 32789

    Listed by BHHS FLORIDA REALTY

    Stellar MLS
  • 251 GLENRIDGE WAY, Winter Park, FL 32789
    3 Beds3 Baths1,314 SqFt
    Price Dropped by $25K

    $899,000

    251 GLENRIDGE WAY, Winter Park, FL 32789

    Listed by RAZZANI INTERNATIONAL REALTY

    Stellar MLS
  • 906 CAMELLIA AVE, Winter Park, FL 32789
    3 Beds2 Baths1,242 SqFt
    1/33 33
    Pending

    $3,250

    906 CAMELLIA AVE, Winter Park, FL 32789

    Listed by FANNIE HILLMAN & ASSOCIATES

    Stellar MLS
  • 3508 MIDIRON DR, Winter Park, FL 32789
    2 Beds1 Bath1,036 SqFt
    1/12 12
    Pending

    $2,195

    3508 MIDIRON DR, Winter Park, FL 32789

    Listed by REAL PROPERTY MANAGEMENT AND REALTY

    Stellar MLS
  • 644 N KNOWLES AVE #8, Winter Park, FL 32789
    3 Beds2 Baths1,130 SqFt
    1/26 26
    Active

    $2,950

    644 N KNOWLES AVE #8, Winter Park, FL 32789

    Listed by BELMONT REALTY

    Stellar MLS
  • 660 KILLARNEY BAY CT #6, Winter Park, FL 32789
    2 Beds3 Baths1,214 SqFt
    1/55 55
    Active

    $2,995

    660 KILLARNEY BAY CT #6, Winter Park, FL 32789

    Listed by FLORIDA ONE REAL ESTATE LLC

    Stellar MLS
  • 2176 CRANDON AVE, Winter Park, FL 32789
    2 Beds1 Bath1,000 SqFt
    1/15 15
    Active

    $2,550

    2176 CRANDON AVE, Winter Park, FL 32789

    Listed by CORCORAN PREMIER REALTY

    Stellar MLS
  • 1250 S DENNING DR #108, Winter Park, FL 32789
    1 Bed1 Bath658 SqFt
    1/15 15
    Price Dropped by $2K

    $186,000

    1250 S DENNING DR #108, Winter Park, FL 32789

    Listed by LOVELAND PROPERTIES

    Stellar MLS
  • 1773 WALNUT AVE, Winter Park, FL 32789
    4 Beds2 Baths2,146 SqFt
    1/4 4
    Pending

    $645,000

    1773 WALNUT AVE, Winter Park, FL 32789

    Listed by CORCORAN PREMIER REALTY

    Stellar MLS
  • 1361 PALMER AVE., Winter Park, FL 32789
    5 Beds4 Baths3,558 SqFt
    1/43 43
    Price Dropped by $154K

    $2,195,000

    1361 PALMER AVE., Winter Park, FL 32789

    Listed by PREMIER SOTHEBY'S INTL. REALTY

    Stellar MLS
  • 184 SANDLEWOOD TRL #2, Winter Park, FL 32789
    2 Beds3 Baths1,133 SqFt
    1/26 26
    Price Dropped by $8K

    $342,000

    184 SANDLEWOOD TRL #2, Winter Park, FL 32789

    Listed by EXP REALTY LLC

    Stellar MLS
  • 151 N ORLANDO AVE #118, Winter Park, FL 32789
    2 Beds1 Bath710 SqFt
    1/4 4
    Active

    $299,999

    151 N ORLANDO AVE #118, Winter Park, FL 32789

    Listed by FLORIDA DREAMS REALTY GRP INC

    Stellar MLS
  • 521 S PHELPS AVE, Winter Park, FL 32789
    4 Beds5 Baths3,883 SqFt
    1/34 34
    Active

    $2,455,000

    521 S PHELPS AVE, Winter Park, FL 32789

    Listed by LA ROSA REALTY HORIZONS LLC

    Stellar MLS
  • 952 MOSS LN, Winter Park, FL 32789
    4 Beds4 Baths3,474 SqFt
    1/55 55
    Price Dropped by $40K

    $1,554,950

    952 MOSS LN, Winter Park, FL 32789

    Listed by THE SHOP REAL ESTATE CO.

    Stellar MLS
  • 987 CHEROKEE AVE, Winter Park, FL 32789
    7,405 Sqft Lot
    1/2 2
    Active

    $1,500

    987 CHEROKEE AVE, Winter Park, FL 32789

    Listed by EXP REALTY LLC

    Stellar MLS
  • 1695 LEE RD #E103, Winter Park, FL 32789
    2 Beds1 Bath881 SqFt
    1/34 34
    Active

    $1,800

    1695 LEE RD #E103, Winter Park, FL 32789

    Listed by ROBERT SLACK LLC

    Stellar MLS
  • 1741 PALMER AVE, Winter Park, FL 32789
    3 Beds3 Baths2,351 SqFt
    1/59 59
    Active

    $1,595,000

    1741 PALMER AVE, Winter Park, FL 32789

    Listed by CENTRAL FLORIDA PRIME REAL ESTATE LLC

    Stellar MLS
  • 185 SYLVAN BLVD, Winter Park, FL 32789
    4 Beds5 Baths3,138 SqFt
    1/9 9
    Active

    $2,590,000

    185 SYLVAN BLVD, Winter Park, FL 32789

    Listed by COMPASS FLORIDA LLC

    Stellar MLS
  • 633 BALMORAL RD, Winter Park, FL 32789
    4 Beds3 Baths2,674 SqFt
    1/25 25
    Price Dropped by $101K

    $1,999,000

    633 BALMORAL RD, Winter Park, FL 32789

    Listed by COMPASS FLORIDA LLC

    Stellar MLS
  • 490 SHOREVIEW AVE, Winter Park, FL 32789
    3 Beds2 Baths2,266 SqFt
    1/35 35
    Pending

    $599,000

    490 SHOREVIEW AVE, Winter Park, FL 32789

    Listed by FLORIDA HOME TEAM REALTY LLC

    Stellar MLS
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The Dillard Team Drafting   (3)
      Home
      Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      Sell
      1. Sell My Home
      2. Home Valuation
      Neighborhoods
      1. Fish Hawk
      2. Bloomingdale
      3. Valrico
      4. Lithia
      5. Brandon
      6. Dover
      7. Thonotosassa
      8. Seffner
      9. Plant City
      10. Riverview
      11. Apollo Beach
      12. Ruskin
      13. Tampa
      14. Live Oak Preserve
      15. St. Petersburg
      16. Downtown St. Petersburg
      17. Driftwood
      18. Jungle Terrace
      Blogs
      Payment Calculator
      About
      1. About Us
      2. Contact Us
      3. Reviews
LPT Realty

Stacy Dillard License ID: BK-3228574

+1(813) 298-7696 stacy@dillardrealtygroup.com

Tampa Bay Area, Florida

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

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.
The Dillard Team Drafting   (3)
      Home
      Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      Sell
      1. Sell My Home
      2. Home Valuation
      Neighborhoods
      1. Fish Hawk
      2. Bloomingdale
      3. Valrico
      4. Lithia
      5. Brandon
      6. Dover
      7. Thonotosassa
      8. Seffner
      9. Plant City
      10. Riverview
      11. Apollo Beach
      12. Ruskin
      13. Tampa
      14. Live Oak Preserve
      15. St. Petersburg
      16. Downtown St. Petersburg
      17. Driftwood
      18. Jungle Terrace
      Blogs
      Payment Calculator
      About
      1. About Us
      2. Contact Us
      3. Reviews
LPT Realty

Stacy Dillard License ID: BK-3228574

+1(813) 298-7696 stacy@dillardrealtygroup.com

Tampa Bay Area, Florida

Get My App

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

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

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.