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Winter Springs Homes For Sale & Real Estate - 217 homes

Winter Springs homes for sale are located in Seminole County, Florida. Find homes in Winter Springs for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Springs houses.

Location: Winter Springs

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  • 498 GREEN SPRING CIR, WINTER SPRINGS, FL 32708

    $249,00011 Days on yellowkey   MLS ID: O6418425

    For Sale O6418425 - 498 GREEN SPRING CIR, WINTER SPRINGS, FL 32708 20 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1363
       Built: 1987
    Monthly Fee: $190
       Tax: $1,639 (2025)
    Community: Mount Greenwood Unit 4 Of
    Townhouse


    Estimated Monthly Payment: $1,691 (change assumption)
    Mortgage ($1,364) + Fees ($190) + Taxes in 2025 ($137)


    Taxes:$1,639

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 525 SADDLEWOOD LN, WINTER SPRINGS, FL 32708

    $685,00018 Days on yellowkey   MLS ID: O6416232

    For Sale O6416232 - 525 SADDLEWOOD LN, WINTER SPRINGS, FL 32708 32 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3246
       Built: 1996
    Monthly Fee: $42
       Tax: $4,016 (2025)
    Community: Winding Hollow Unit 2
    Single Family


    Estimated Monthly Payment: $4,130 (change assumption)
    Mortgage ($3,753) + Fees ($42) + Taxes in 2025 ($335)


    Taxes:$4,016

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 411 GREEN SPRING CIR, WINTER SPRINGS, FL 32708

    $224,900307 Days on yellowkey   MLS ID: O6339004

    0 Days Off yellowkey (back on 6/2/2026)

    SHORT SALE O6339004 - 411 GREEN SPRING CIR, WINTER SPRINGS, FL 32708 26 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 1130
       Built: 1990
    Monthly Fee: $190
       Tax: $420 (2025)
    Community: Mount Greenwood Unit 4
    Townhouse


    Estimated Monthly Payment: $1,457 (change assumption)
    Mortgage ($1,232) + Fees ($190) + Taxes in 2025 ($35)


    Taxes:$420

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 497 CLUB DR, WINTER SPRINGS, FL 32708

    $218,00045 Days on yellowkey   MLS ID: O6408474

    REDUCED by $14,800 (6.4%) on 05/23/2026

    For Sale O6408474 - 497 CLUB DR, WINTER SPRINGS, FL 32708 27 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1224
       Built: 1987
    Monthly Fee: $520
       Tax: $3,344 (2025)
    Community: Cypress Club
    Townhouse


    Estimated Monthly Payment: $1,993 (change assumption)
    Mortgage ($1,194) + Fees ($520) + Taxes in 2025 ($279)


    Taxes:$3,344

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 577 WALDEN CT, WINTER SPRINGS, FL 32708

    $399,00022 Days on yellowkey   MLS ID: V4949540

    2 Days Off yellowkey (back on 6/30/2026)

    REDUCED by $6,000 (1.5%) on 06/20/2026

    For Sale V4949540 - 577 WALDEN CT, WINTER SPRINGS, FL 32708 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1560
       Built: 1974   Tax: $3,414 (2025)
    Community: Walden Terrace
    Single Family


    Estimated Monthly Payment: $2,471 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($284)


    Taxes:$3,414

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Tuskawilla Middle


  • 1385 PONCE DE LEON BLVD, WINTER SPRINGS, FL 32708

    $367,0003 Days on yellowkey   MLS ID: W7887141

    1 Days Off yellowkey (back on 6/30/2026)

    For Sale W7887141 - 1385 PONCE DE LEON BLVD, WINTER SPRINGS, FL 32708 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1460
       Built: 1980
    Monthly Fee: $29
       Tax: $4,679 (2025)
    Community: Sunrise Unit 2-A
    Single Family


    Estimated Monthly Payment: $2,430 (change assumption)
    Mortgage ($2,011) + Fees ($29) + Taxes in 2025 ($390)


    Taxes:$4,679

    Elementary School: Rainbow Elementary

    High School: Oviedo High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 65 S DEVON AVE, WINTER SPRINGS, FL 32708

    $305,00050 Days on yellowkey   MLS ID: O6404319

    REDUCED by $9,900 (3.1%) on 06/30/2026

    For Sale O6404319 - 65 S DEVON AVE, WINTER SPRINGS, FL 32708 33 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1075
       Built: 1960   Tax: $2,218 (2024)
    Community: North Orlando 2Nd Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,856 (change assumption)
    Mortgage ($1,671) + Taxes in 2024 ($185)


    Taxes:$2,218

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 1055 CHESTERFIELD CIR, WINTER SPRINGS, FL 32708

    $499,90026 Days on yellowkey   MLS ID: O6413841

    REDUCED by $10,100 (2.0%) on 06/23/2026

    For Sale O6413841 - 1055 CHESTERFIELD CIR, WINTER SPRINGS, FL 32708 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1665
       Built: 1984
    Monthly Fee: $25
       Tax: $5,048 (2025)
    Community: Amherst
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,185 (change assumption)
    Mortgage ($2,739) + Fees ($25) + Taxes in 2025 ($421)


    Taxes:$5,048

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 439 OLD FARM LN, WINTER SPRINGS, FL 32708

    $318,50062 Days on yellowkey   MLS ID: O6403125

    REDUCED by $11,400 (3.5%) on 06/30/2026

    For Sale O6403125 - 439 OLD FARM LN, WINTER SPRINGS, FL 32708 68 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1504
       Built: 2007
    Monthly Fee: $300
       Tax: $5,063 (2025)
    Community: Jesups Reserve Twnhms Rep
    Townhouse


    Estimated Monthly Payment: $2,467 (change assumption)
    Mortgage ($1,745) + Fees ($300) + Taxes in 2025 ($422)


    Taxes:$5,063

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1035 N ELK CT, WINTER SPRINGS, FL 32708

    $900,00022 Days on yellowkey   MLS ID: O6414324

    0 Days Off yellowkey (back on 6/27/2026)

    For Sale O6414324 - 1035 N ELK CT, WINTER SPRINGS, FL 32708 56 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3360
       Built: 1978   Tax: $10,432 (2025)
    Community: Winter Spgs Unit 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,801 (change assumption)
    Mortgage ($4,931) + Taxes in 2025 ($869)


    Taxes:$10,432

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 4967 COURTLAND LOOP, WINTER SPRINGS, FL 32708

    $790,0004 Days on yellowkey   MLS ID: O6419028

    For Sale O6419028 - 4967 COURTLAND LOOP, WINTER SPRINGS, FL 32708 56 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2339
       Built: 1989
    Monthly Fee: $40
       Tax: $6,933 (2025)
    Community: Tuskabay
    Single Family


    Estimated Monthly Payment: $4,946 (change assumption)
    Mortgage ($4,329) + Fees ($40) + Taxes in 2025 ($578)


    Taxes:$6,933

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 216 TAVESTOCK LOOP, WINTER SPRINGS, FL 32708

    $640,0001 Day on yellowkey   MLS ID: O6419655

    For Sale O6419655 - 216 TAVESTOCK LOOP, WINTER SPRINGS, FL 32708 25 photos

    Bed: 5   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2355
       Built: 2000
    Monthly Fee: $150
       Tax: $7,334 (2025)
    Community: Parkstone
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,268 (change assumption)
    Mortgage ($3,507) + Fees ($150) + Taxes in 2025 ($611)


    Taxes:$7,334

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1304 ORTEGA ST, WINTER SPRINGS, FL 32708

    $488,00057 Days on yellowkey   MLS ID: TB8504998

    REDUCED by $11,000 (2.2%) on 06/29/2026

    For Sale TB8504998 - 1304 ORTEGA ST, WINTER SPRINGS, FL 32708 45 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2152
       Built: 1985
    Monthly Fee: $30
       Tax: $5,238 (2025)
    Community: Sunrise Estates Unit 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,140 (change assumption)
    Mortgage ($2,674) + Fees ($30) + Taxes in 2025 ($436)


    Taxes:$5,238

    Elementary School: Rainbow Elementary

    High School: Oviedo High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 161 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708

    $444,990118 Days on yellowkey   MLS ID: O6386458

    5 Days Off yellowkey (back on 6/23/2026)

    REDUCED by $40,000 (8.2%) on 06/01/2026

    For Sale O6386458 - 161 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1704
       Built: 2026
    Monthly Fee: $356
       Tax: $1,457 (2025)
    Community: Hickory Grove
    Townhouse


    Estimated Monthly Payment: $2,916 (change assumption)
    Mortgage ($2,438) + Fees ($356) + Taxes in 2025 ($121)


    Taxes:$1,457

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 314 SAN GABRIEL ST, WINTER SPRINGS, FL 32708

    $279,990263 Days on yellowkey   MLS ID: O6350799

    2 Days Off yellowkey (back on 6/29/2026)

    For Sale O6350799 - 314 SAN GABRIEL ST, WINTER SPRINGS, FL 32708 30 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1091
       Built: 1992
    Monthly Fee: $127
       Tax: $2,209 (2024)
    Community: Deersong
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,845 (change assumption)
    Mortgage ($1,534) + Fees ($127) + Taxes in 2024 ($184)


    Taxes:$2,209

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 167 CONSTITUTION WAY, WINTER SPRINGS, FL 32708

    $294,00018 Days on yellowkey   MLS ID: O6416491

    0 Days Off yellowkey (back on 6/29/2026)

    For Sale O6416491 - 167 CONSTITUTION WAY, WINTER SPRINGS, FL 32708 20 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1275
       Built: 2005
    Monthly Fee: $300
       Tax: $2,571 (2025)
    Community: Heritage Park
    Townhouse


    Estimated Monthly Payment: $2,125 (change assumption)
    Mortgage ($1,611) + Fees ($300) + Taxes in 2025 ($214)


    Taxes:$2,571

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 1647 EAGLE NEST CIR, WINTER SPRINGS, FL 32708

    $840,00012 Days on yellowkey   MLS ID: O6418175

    0 Days Off yellowkey (back on 6/29/2026)

    For Sale O6418175 - 1647 EAGLE NEST CIR, WINTER SPRINGS, FL 32708 35 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2749
       Built: 1993
    Monthly Fee: $48
       Tax: $5,419 (2025)
    Community: Glen Eagle
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,102 (change assumption)
    Mortgage ($4,603) + Fees ($48) + Taxes in 2025 ($452)


    Taxes:$5,419

    Elementary School: Rainbow Elementary

    High School: Oviedo High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 809 BIG BUCK CIR, WINTER SPRINGS, FL 32708

    $549,00016 Days on yellowkey   MLS ID: O6416554

    For Sale O6416554 - 809 BIG BUCK CIR, WINTER SPRINGS, FL 32708 53 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2250
       Built: 1984
    Monthly Fee: $3
       Tax: $6,018 (2025)
    Community: Oak Forest Unit 3
    Single Family


    Estimated Monthly Payment: $3,513 (change assumption)
    Mortgage ($3,008) + Fees ($3) + Taxes in 2025 ($502)


    Taxes:$6,018

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1357 MILL STREAM LN, WINTER SPRINGS, FL 32708

    $399,90013 Days on yellowkey   MLS ID: O6417015

    REDUCED by $100 (0.0%) on 06/25/2026

    For Sale O6417015 - 1357 MILL STREAM LN, WINTER SPRINGS, FL 32708 28 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1606
       Built: 2015
    Monthly Fee: $230
       Tax: $4,811 (2025)
    Community: Jesups Landing
    Townhouse


    Estimated Monthly Payment: $2,822 (change assumption)
    Mortgage ($2,191) + Fees ($230) + Taxes in 2025 ($401)


    Taxes:$4,811

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 358 BRUSHWOOD LN, WINTER SPRINGS, FL 32708

    $468,00026 Days on yellowkey   MLS ID: O6412915

    For Sale O6412915 - 358 BRUSHWOOD LN, WINTER SPRINGS, FL 32708 20 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1922
       Built: 1986
    Monthly Fee: $29
       Tax: $3,177 (2025)
    Community: Deer Run Unit 23C
    Single Family


    Estimated Monthly Payment: $2,858 (change assumption)
    Mortgage ($2,564) + Fees ($29) + Taxes in 2025 ($265)


    Taxes:$3,177

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2025

    Middle School: Tuskawilla Middle




Why Bother Searching Elsewhere for Winter Springs Homes for Sale and Other Real Estate?

Winter Springs home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Winter Springs . You can use our website to view Multiple Listing Service (MLS) data on Winter Springs Real Estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Winter Springs listings.



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.