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Winter Springs Single Family Homes For Sale - 140 homes

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

Location: Winter Springs

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  • 710 BRIARWOOD DR, WINTER SPRINGS, FL 32708

    $372,50048 Days on yellowkey   MLS ID: O6396343

    REDUCED by $2,500 (0.7%) on 05/08/2026

    For Sale O6396343 - 710 BRIARWOOD DR, WINTER SPRINGS, FL 32708 22 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1769
       Built: 1974
    Monthly Fee: $90
       Tax: $4,070 (2025)
    Community: Wildwood
    Single Family


    Estimated Monthly Payment: $2,470 (change assumption)
    Mortgage ($2,041) + Fees ($90) + Taxes in 2025 ($339)


    Taxes:$4,070

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 221 SHERRY AVE, WINTER SPRINGS, FL 32708

    $366,90015 Days on yellowkey   MLS ID: O6404854

    For Sale O6404854 - 221 SHERRY AVE, WINTER SPRINGS, FL 32708 18 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1700
       Built: 1971   Tax: $523 (2025)
    Community: North Orlando Townsite Fourth Add Replat
    Single Family


    Estimated Monthly Payment: $2,054 (change assumption)
    Mortgage ($2,010) + Taxes in 2025 ($44)


    Taxes:$523

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 203 WISE OWL WAY, WINTER SPRINGS, FL 32708

    $599,900104 Days on yellowkey   MLS ID: O6380678

    0 Days Off yellowkey (back on 5/8/2026)

    REDUCED by $14,600 (2.4%) on 03/31/2026

    For Sale O6380678 - 203 WISE OWL WAY, WINTER SPRINGS, FL 32708 60 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2531
       Built: 2020
    Monthly Fee: $130
       Tax: $6,177 (2024)
    Community: Tuskawilla Crossings
    Single Family


    Estimated Monthly Payment: $3,932 (change assumption)
    Mortgage ($3,287) + Fees ($130) + Taxes in 2024 ($515)


    Taxes:$6,177

    Elementary School: Layer Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 120 N FAIRFAX AVE, WINTER SPRINGS, FL 32708

    $263,00041 Days on yellowkey   MLS ID: O6398133

    FORECLOSURE O6398133 - 120 N FAIRFAX AVE, WINTER SPRINGS, FL 32708 13 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1148
       Built: 1959   Tax: $2,741 (2025)
    Community: North Orlando
    Single Family


    Estimated Monthly Payment: $1,669 (change assumption)
    Mortgage ($1,441) + Taxes in 2025 ($228)


    Taxes:$2,741

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1686 EAGLE NEST CIR, WINTER SPRINGS, FL 32708

    $714,90029 Days on yellowkey   MLS ID: O6401291

    0 Days Off yellowkey (back on 4/24/2026)

    For Sale O6401291 - 1686 EAGLE NEST CIR, WINTER SPRINGS, FL 32708 95 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2233
       Built: 1989
    Monthly Fee: $48
       Tax: $4,456 (2025)
    Community: Glen Eagle Unit 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,336 (change assumption)
    Mortgage ($3,917) + Fees ($48) + Taxes in 2025 ($371)


    Taxes:$4,456

    Elementary School: Rainbow Elementary

    High School: Oviedo High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 820 WAKULLA LN, WINTER SPRINGS, FL 32708

    $424,90015 Days on yellowkey   MLS ID: TB8504175

    For Sale TB8504175 - 820 WAKULLA LN, WINTER SPRINGS, FL 32708 15 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1658
       Built: 2012
    Monthly Fee: $167
       Tax: $5,649 (2025)
    Community: Winter Spgs Village Ph 1
    Single Family


    Estimated Monthly Payment: $2,966 (change assumption)
    Mortgage ($2,328) + Fees ($167) + Taxes in 2025 ($471)


    Taxes:$5,649

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1716 FOX GLEN CT, WINTER SPRINGS, FL 32708

    $479,000177 Days on yellowkey   MLS ID: O6362670

    For Sale O6362670 - 1716 FOX GLEN CT, WINTER SPRINGS, FL 32708 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1889
       Built: 2000
    Monthly Fee: $115
       Tax: $2,322 (2024)
    Community: Fox Glen At Chelsea Parc Tuscawilla Ph 2
    Single Family


    Estimated Monthly Payment: $2,933 (change assumption)
    Mortgage ($2,625) + Fees ($115) + Taxes in 2024 ($194)


    Taxes:$2,322

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1307 ORTEGA ST, WINTER SPRINGS, FL 32708

    $438,00064 Days on yellowkey   MLS ID: O6391915

    REDUCED by $7,000 (1.6%) on 04/27/2026

    For Sale O6391915 - 1307 ORTEGA ST, WINTER SPRINGS, FL 32708 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1881
       Built: 1984
    Monthly Fee: $29
       Tax: $4,874 (2026)
    Community: Sunrise Unit 2-B
    Single Family


    Estimated Monthly Payment: $2,835 (change assumption)
    Mortgage ($2,400) + Fees ($29) + Taxes in 2026 ($406)


    Taxes:$4,874

    Elementary School: Rainbow Elementary

    High School: Oviedo High

    Tax Year: 2026

    Middle School: Indian Trails Middle


  • 1385 SAN DIEGO CT, WINTER SPRINGS, FL 32708

    $349,00043 Days on yellowkey   MLS ID: O6397680

    REDUCED by $8,500 (2.4%) on 05/06/2026

    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: $2,070 (change assumption)
    Mortgage ($1,912) + 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


  • 1825 SENECA BLVD, WINTER SPRINGS, FL 32708

    $675,00045 Days on yellowkey   MLS ID: O6396955

    REDUCED by $25,000 (3.6%) on 05/06/2026

    For Sale O6396955 - 1825 SENECA BLVD, WINTER SPRINGS, FL 32708 82 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2711
       Built: 1989
    Monthly Fee: $8
       Tax: $1,171 (2025)
    Community: Tuscawilla Unit 14B
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,804 (change assumption)
    Mortgage ($3,699) + Fees ($8) + Taxes in 2025 ($98)


    Taxes:$1,171

    Elementary School: Lawton Elementary

    High School: Oviedo High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 335 KIRKCALDY DR, WINTER SPRINGS, FL 32708

    $339,90017 Days on yellowkey   MLS ID: O6400818

    For Sale O6400818 - 335 KIRKCALDY DR, WINTER SPRINGS, FL 32708 50 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1178
       Built: 1984
    Monthly Fee: $36
       Tax: $3,693 (2025)
    Community: Highland Village 1
    Single Family


    Estimated Monthly Payment: $2,206 (change assumption)
    Mortgage ($1,862) + Fees ($36) + Taxes in 2025 ($308)


    Taxes:$3,693

    Elementary School: Highlands Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: South Seminole Middle


  • 788 ANDOVER CIR, WINTER SPRINGS, FL 32708

    $445,00038 Days on yellowkey   MLS ID: O6397299

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

    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


  • 120 E BAHAMA RD, WINTER SPRINGS, FL 32708

    $1,299,900108 Days on yellowkey   MLS ID: O6379165

    REDUCED by $100,000 (7.1%) on 04/09/2026

    For Sale O6379165 - 120 E BAHAMA RD, WINTER SPRINGS, FL 32708 49 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 4464
       Built: 1989   Tax: $12,488 (2025)
    Community: Bahama Ranches
    Spa: No

    Single Family


    Estimated Monthly Payment: $8,163 (change assumption)
    Mortgage ($7,123) + Taxes in 2025 ($1,041)


    Taxes:$12,488

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


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

    $815,00054 Days on yellowkey   MLS ID: S5146734

    REDUCED by $32,500 (3.8%) on 05/06/2026

    For Sale S5146734 - 135 W TRADE WINDS RD, WINTER SPRINGS, FL 32708 45 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: $4,834 (change assumption)
    Mortgage ($4,466) + Taxes in 2024 ($368)


    Taxes:$4,421

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1452 CONNORS LN, WINTER SPRINGS, FL 32708

    $475,00018 Days on yellowkey   MLS ID: O6404505

    0 Days Off yellowkey (back on 5/5/2026)

    For Sale O6404505 - 1452 CONNORS LN, WINTER SPRINGS, FL 32708 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1766
       Built: 1986
    Monthly Fee: $90
       Tax: $4,752 (2024)
    Community: Wedgewood Tennis Villas
    Single Family


    Estimated Monthly Payment: $3,089 (change assumption)
    Mortgage ($2,603) + Fees ($90) + Taxes in 2024 ($396)


    Taxes:$4,752

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 4951 COURTLAND LOOP, WINTER SPRINGS, FL 32708

    $690,000127 Days on yellowkey   MLS ID: O6374007

    REDUCED by $10,000 (1.4%) on 05/05/2026

    For Sale O6374007 - 4951 COURTLAND LOOP, WINTER SPRINGS, FL 32708 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2562
       Built: 1984
    Monthly Fee: $40
       Tax: $7,807 (2024)
    Community: Tuskabay Ph 1
    Single Family


    Estimated Monthly Payment: $4,471 (change assumption)
    Mortgage ($3,781) + Fees ($40) + Taxes in 2024 ($651)


    Taxes:$7,807

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 736 SUMMERLAND DR, WINTER SPRINGS, FL 32708

    $298,90028 Days on yellowkey   MLS ID: O6402028

    REDUCED by $1,100 (0.4%) on 05/05/2026

    For Sale O6402028 - 736 SUMMERLAND DR, WINTER SPRINGS, FL 32708 67 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1298
       Built: 1983
    Monthly Fee: $95
       Tax: $2,905 (2025)
    Community: Wildwood
    Single Family


    Estimated Monthly Payment: $1,975 (change assumption)
    Mortgage ($1,638) + Fees ($95) + Taxes in 2025 ($242)


    Taxes:$2,905

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1029 E PEBBLE BEACH CIR, WINTER SPRINGS, FL 32708

    $395,00021 Days on yellowkey   MLS ID: O6404082

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

    For Sale O6404082 - 1029 E PEBBLE BEACH CIR, WINTER SPRINGS, FL 32708 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1314
       Built: 1993
    Monthly Fee: $117
       Tax: $1,736 (2025)
    Community: Country Club Village Unit 3
    Single Family


    Estimated Monthly Payment: $2,426 (change assumption)
    Mortgage ($2,164) + Fees ($117) + Taxes in 2025 ($145)


    Taxes:$1,736

    Elementary School: Keeth Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle


  • 903 TORREY PINE DR, WINTER SPRINGS, FL 32708

    $469,900105 Days on yellowkey   MLS ID: O6377459

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

    For Sale O6377459 - 903 TORREY PINE DR, WINTER SPRINGS, FL 32708 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1501
       Built: 1998
    Monthly Fee: $126
       Tax: $2,155 (2024)
    Community: Greenbriar Sub Ph 2
    Single Family


    Estimated Monthly Payment: $2,880 (change assumption)
    Mortgage ($2,575) + Fees ($126) + Taxes in 2024 ($180)


    Taxes:$2,155

    Elementary School: Rainbow Elementary

    High School: Winter Springs High

    Tax Year: 2024

    Middle School: Indian Trails Middle


  • 421 HORIZON DR, WINTER SPRINGS, FL 32708

    $299,90084 Days on yellowkey   MLS ID: O6384932

    REDUCED by $15,100 (4.8%) on 04/29/2026

    For Sale O6384932 - 421 HORIZON DR, WINTER SPRINGS, FL 32708 29 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1069
       Built: 1998
    Monthly Fee: $142
       Tax: $3,681 (2025)
    Community: Seasons The
    Single Family


    Estimated Monthly Payment: $2,092 (change assumption)
    Mortgage ($1,643) + Fees ($142) + Taxes in 2025 ($307)


    Taxes:$3,681

    Elementary School: Winter Springs Elementary

    High School: Winter Springs High

    Tax Year: 2025

    Middle School: Indian Trails Middle




Why Bother Searching Elsewhere for Winter Springs Single Family Homes for Sale?

Winter Springs home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Springs. You can use our website to view Multiple Listing Service (MLS) data on Winter Springs single family homes. 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 single family home 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.