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Displaying: For Sale

Location: Winter Springs

Property Type(s): Single Family

Winter Springs - 130 properties found

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  • 270 SAN GABRIEL ST, WINTER SPRINGS, FL 32708

    $259,000173 Days on yellowkey   MLS ID: O6359666

    For Sale O6359666 - 270 SAN GABRIEL ST, WINTER SPRINGS, FL 32708 35 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1089
       Built: 1994
    Monthly Fee: $121
       Tax: $327 (2024)
    Community: Deersong 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,567 (change assumption)
    Mortgage ($1,419) + Fees ($121) + Taxes in 2024 ($27)


    Taxes:$327

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 515 SEASONS CT, WINTER SPRINGS, FL 32708

    $299,900236 Days on yellowkey   MLS ID: O6343009

    1 Days Off yellowkey (back on 4/30/2026)

    For Sale O6343009 - 515 SEASONS CT, WINTER SPRINGS, FL 32708 53 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1101
       Built: 1996
    Monthly Fee: $120
       Tax: $3,258 (2024)
    Community: Seasons The
    Single Family


    Estimated Monthly Payment: $2,035 (change assumption)
    Mortgage ($1,643) + Fees ($120) + Taxes in 2024 ($272)


    Taxes:$3,258

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 448 MACGREGOR RD, WINTER SPRINGS, FL 32708

    $365,00026 Days on yellowkey   MLS ID: O6397231

    REDUCED by $10,000 (2.7%) on 04/29/2026

    For Sale O6397231 - 448 MACGREGOR RD, WINTER SPRINGS, FL 32708 26 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1477
       Built: 1993
    Monthly Fee: $6
       Tax: $1,141 (2024)
    Community: Highland Village 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,101 (change assumption)
    Mortgage ($2,000) + Fees ($6) + Taxes in 2024 ($95)


    Taxes:$1,141

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 201 BURGESS DR, WINTER SPRINGS, FL 32708

    $675,00011 Days on yellowkey   MLS ID: O6401349

    For Sale O6401349 - 201 BURGESS DR, WINTER SPRINGS, FL 32708 40 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 3046
       Built: 2003
    Monthly Fee: $195
       Tax: $7,948 (2025)
    Community: Avery Park
    Single Family


    Estimated Monthly Payment: $4,556 (change assumption)
    Mortgage ($3,699) + Fees ($195) + Taxes in 2025 ($662)


    Taxes:$7,948

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1411 BORG LN, WINTER SPRINGS, FL 32708

    $405,00093 Days on yellowkey   MLS ID: O6378665

    For Sale O6378665 - 1411 BORG LN, WINTER SPRINGS, FL 32708 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1368
       Built: 1981
    Monthly Fee: $90
       Tax: $1,871 (2024)
    Community: Wedgewood Tennis Villas
    Single Family


    Estimated Monthly Payment: $2,465 (change assumption)
    Mortgage ($2,219) + Fees ($90) + Taxes in 2024 ($156)


    Taxes:$1,871

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 30 S EDGEMON AVE, WINTER SPRINGS, FL 32708

    $250,00033 Days on yellowkey   MLS ID: O6394469

    0 Days Off yellowkey (back on 4/18/2026)

    For Sale O6394469 - 30 S EDGEMON AVE, WINTER SPRINGS, FL 32708 30 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1545
       Built: 1960   Tax: $318 (2024)
    Community: North Orlando 2Nd Add
    Single Family


    Estimated Monthly Payment: $1,396 (change assumption)
    Mortgage ($1,370) + Taxes in 2024 ($26)


    Taxes:$318

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 239 PANORAMA DR, WINTER SPRINGS, FL 32708

    $340,00024 Days on yellowkey   MLS ID: O6397776

    REDUCED by $10,000 (2.9%) on 04/24/2026

    For Sale O6397776 - 239 PANORAMA DR, WINTER SPRINGS, FL 32708 28 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1349
       Built: 1996
    Monthly Fee: $139
       Tax: $4,336 (2025)
    Community: Seasons The
    Single Family


    Estimated Monthly Payment: $2,363 (change assumption)
    Mortgage ($1,863) + Fees ($139) + Taxes in 2025 ($361)


    Taxes:$4,336

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 214 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708

    $649,90072 Days on yellowkey   MLS ID: O6372400

    REDUCED by $25,100 (3.7%) on 04/15/2026

    For Sale O6372400 - 214 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708 74 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2474
       Built: 2001
    Monthly Fee: $42
       Tax: $5,539 (2024)
    Community: Chestnut Ridge
    Single Family


    Estimated Monthly Payment: $4,065 (change assumption)
    Mortgage ($3,561) + Fees ($42) + Taxes in 2024 ($462)


    Taxes:$5,539

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 1054 WINDING WATERS CIR, WINTER SPRINGS, FL 32708

    $559,90019 Days on yellowkey   MLS ID: O6398229

    REDUCED by $10,000 (1.8%) on 04/29/2026

    For Sale O6398229 - 1054 WINDING WATERS CIR, WINTER SPRINGS, FL 32708 29 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2321
       Built: 1998
    Monthly Fee: $42
       Tax: $4,167 (2025)
    Community: Winding Hollow
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,457 (change assumption)
    Mortgage ($3,068) + Fees ($42) + Taxes in 2025 ($347)


    Taxes:$4,167

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1447 BIRD RD, WINTER SPRINGS, FL 32708

    $2,900,00059 Days on yellowkey   MLS ID: O6388126

    For Sale O6388126 - 1447 BIRD RD, WINTER SPRINGS, FL 32708 68 photos

    Bed: 6   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 6132
       Built: 2026   Tax: $2,989 (2024)
    Community: Talis Crossing
    Single Family


    Estimated Monthly Payment: $16,139 (change assumption)
    Mortgage ($15,890) + Taxes in 2024 ($249)


    Taxes:$2,989

    Elementary School: Sterling Park Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: South Seminole Middle


  • 30 SABLE CT, WINTER SPRINGS, FL 32708

    $569,00080 Days on yellowkey   MLS ID: O6382648

    REDUCED by $10,000 (1.7%) on 04/12/2026

    For Sale O6382648 - 30 SABLE CT, WINTER SPRINGS, FL 32708 11 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2674
       Built: 1976   Tax: $3,043 (2024)
    Community: Tuscawilla
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,371 (change assumption)
    Mortgage ($3,118) + Taxes in 2024 ($254)


    Taxes:$3,043

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 422 SANDRINGHAM CT, WINTER SPRINGS, FL 32708

    $822,80073 Days on yellowkey   MLS ID: O6384155

    2 Days Off yellowkey (back on 4/28/2026)

    For Sale O6384155 - 422 SANDRINGHAM CT, WINTER SPRINGS, FL 32708 64 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3512
       Built: 2001
    Monthly Fee: $150
       Tax: $12,732 (2025)
    Community: Parkstone
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,719 (change assumption)
    Mortgage ($4,508) + Fees ($150) + Taxes in 2025 ($1,061)


    Taxes:$12,732

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1385 SAN DIEGO CT, WINTER SPRINGS, FL 32708

    $357,50025 Days on yellowkey   MLS ID: O6397680

    For Sale O6397680 - 1385 SAN DIEGO CT, WINTER SPRINGS, FL 32708 28 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1518
       Built: 1983
    Monthly Fee: $29
       Tax: $1,540 (2024)
    Community: Sunrise Village Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,116 (change assumption)
    Mortgage ($1,959) + Fees ($29) + Taxes in 2024 ($128)


    Taxes:$1,540

    Elementary School: Rainbow Elementary

    High School: Oviedo High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 788 ANDOVER CIR, WINTER SPRINGS, FL 32708

    $445,00020 Days on yellowkey   MLS ID: O6397299

    For Sale O6397299 - 788 ANDOVER CIR, WINTER SPRINGS, FL 32708 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1791
       Built: 1994
    Monthly Fee: $124
       Tax: $3,567 (2025)
    Community: Georgetowne Unit 3
    Single Family


    Estimated Monthly Payment: $2,860 (change assumption)
    Mortgage ($2,438) + Fees ($124) + Taxes in 2025 ($297)


    Taxes:$3,567

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 655 MURPHY RD, WINTER SPRINGS, FL 32708

    $375,00026 Days on yellowkey   MLS ID: O6396767

    5 Days Off yellowkey (back on 4/28/2026)

    For Sale O6396767 - 655 MURPHY RD, WINTER SPRINGS, FL 32708 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1320
       Built: 1981   Tax: $976 (2024)
    Community: Foxmoor Unit 3
    Single Family


    Estimated Monthly Payment: $2,136 (change assumption)
    Mortgage ($2,055) + Taxes in 2024 ($81)


    Taxes:$976

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1502 BLACK BEAR CT, WINTER SPRINGS, FL 32708

    $1,375,00024 Days on yellowkey   MLS ID: O6391020

    0 Days Off yellowkey (back on 4/10/2026)

    For Sale O6391020 - 1502 BLACK BEAR CT, WINTER SPRINGS, FL 32708 1 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3718
       Built: 1988   Tax: $6,979 (2024)
    Community: Bear Creek Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,116 (change assumption)
    Mortgage ($7,534) + Taxes in 2024 ($582)


    Taxes:$6,979

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 214 N ALDERWOOD ST, WINTER SPRINGS, FL 32708

    $339,90034 Days on yellowkey   MLS ID: O6394428

    REDUCED by $10,000 (2.9%) on 04/14/2026

    For Sale O6394428 - 214 N ALDERWOOD ST, WINTER SPRINGS, FL 32708 59 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1053
       Built: 1972   Tax: $657 (2024)
    Community: North Orlando Terrace Unit 1 Sec 3
    Single Family


    Estimated Monthly Payment: $1,917 (change assumption)
    Mortgage ($1,862) + Taxes in 2024 ($55)


    Taxes:$657

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 702 GOLFPOINT DR, WINTER SPRINGS, FL 32708

    $945,00025 Days on yellowkey   MLS ID: O6397566

    REDUCED by $20,000 (2.1%) on 04/27/2026

    For Sale O6397566 - 702 GOLFPOINT DR, WINTER SPRINGS, FL 32708 67 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3660
       Built: 1994
    Monthly Fee: $48
       Tax: $11,586 (2025)
    Community: Glen Eagle Unit 3
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,191 (change assumption)
    Mortgage ($5,178) + Fees ($48) + Taxes in 2025 ($966)


    Taxes:$11,586

    Elementary School: Rainbow Elementary

    High School: Oviedo High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 135 W TRADE WINDS RD, WINTER SPRINGS, FL 32708

    $847,50036 Days on yellowkey   MLS ID: S5146734

    For Sale S5146734 - 135 W TRADE WINDS RD, WINTER SPRINGS, FL 32708 46 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3100
       Built: 1995   Tax: $4,421 (2024)
    Community: Oak Hill Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,012 (change assumption)
    Mortgage ($4,644) + Taxes in 2024 ($368)


    Taxes:$4,421

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 337 KIRKCALDY DR, WINTER SPRINGS, FL 32708

    $284,90093 Days on yellowkey   MLS ID: O6375532

    For Sale O6375532 - 337 KIRKCALDY DR, WINTER SPRINGS, FL 32708 28 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 974
       Built: 1984
    Monthly Fee: $6
       Tax: $1,428 (2024)
    Community: Highland Village 1
    Single Family


    Estimated Monthly Payment: $1,686 (change assumption)
    Mortgage ($1,561) + Fees ($6) + Taxes in 2024 ($119)


    Taxes:$1,428

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None






Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.