- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
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164 Properties Available In Winter Springs
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
![212 PERTH CT #A, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6255244/b982bf5d/1730840471/w600_original_BMBRDsIwCADQE7WQFZh4AP_88QZdS-qMuEWWmHj6vedx7HEFiJKr1__2qb_IbXPwd4zv2mH1OizgfnvMhJMgowCWS0ftSxIlS0TGSYU1sfBUGs-0aMuv3cYZAAD__w-jpg.webp)
$1,800
212 PERTH CT #A, Winter Springs, FL 32708
Listed by ALFANO PROPERTY MANAGEMENT
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1229 WINDING CHASE BLVD, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6254075/5151f7a7/1730658670/w600_original_BMBRDsIgDADQE0HJOsvqAfzzxxsUWHHGusWSmHj6vecYh18BHKOY_PeP_DzW3cDe3r9bg82krw732yMjM-GcE-iFlBOVQLhImFvSwFmnQGXJRWudGmJ8HWs_AwAA__8-jpg.webp)
$630,000
1229 WINDING CHASE BLVD, Winter Springs, FL 32708
Listed by EXP REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![429 SHEOAH BLVD #2, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6254313/8a1ce7a9/1733841971/w600_original_BMBRDsIwCADQE7V0jEzqAfzzxxtAh3VG3CJNTDy97zHGEWeAmLO4_Pa3fCO33cFf0T_bCptLt4Dr5XaiUmZceAJtuKApp2qqiWrhJFhb4jvZShMhkubnYf0fAAD__w-jpg.webp)
$199,500
429 SHEOAH BLVD #2, Winter Springs, FL 32708
Listed by COMPASS FLORIDA LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1042 WINDING WATERS CIR, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6253533/3032adcb/1733166076/w600_original_BMBRCsIwDAbgE7UZ7Lc1HsA3X7zBT9PViXHDDARP7_c4jj0uIjFnOn_bm9_IbXPxV4zParI6Rw-5Xe911qo4AbLACkux1DqYALVEXZjs3DDpRFjt-bn38Q8AAP__-jpg.webp)
$649,000
1042 WINDING WATERS CIR, Winter Springs, FL 32708
Listed by RE/MAX TOWN & COUNTRY REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![154 TUSKAWILLA RD #400, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6253792/6ca4014d/1730388672/w600_original_BMBRDoIwDAbgE22dsLnVA_jmizf4oXVirBBLYuLp-Z77vvmFyMcIw3_94OdxXo3s7f27CC2Grk63672O3OpwLo2EJznVLAHlkUKekcKUdAgCzamCWyscX5v2IwAA__8-jpg.webp)
$2,475
154 TUSKAWILLA RD #400, Winter Springs, FL 32708
Listed by LIGHTHOUSE REALTY GROUP OF FLORIDA
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![302 INGLENOOK CIR, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6253195/b78f1f7d/1730380572/w600_original_BMDLDcIwDAbgiRLHzQsYgBsXNvgVh1CEaYUjITF9v-ecu12ILHoo_tsHP_NtU9K3je8qtCpGN7pd7zWeK-eFC1UujTmLi0mqS23pDqHARTzAklM4SfCvvY8jAAD__w-jpg.webp)
$465,000
302 INGLENOOK CIR, Winter Springs, FL 32708
Listed by CFRP REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![154 TUSKAWILLA RD #112, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6253415/3879a11d/1730300484/w600_original_BMBRDsIwCADQE7UsrhTqAfzzxxswSuqMuEWWmHj6vedx7HEFiDmLy3_7yC-ybg7-jvFdO6wuwwLutwfNjWolRuBJtF0Kps5FU6FpSYzSk2irVhc0LJhfu40zAAD__w-jpg.webp)
$2,075
154 TUSKAWILLA RD #112, Winter Springs, FL 32708
Listed by LIGHTHOUSE REALTY GROUP OF FLORIDA
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![4249 E WEEPING WILLOW CIR, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6252806/86e6b6b3/1730244670/w600_original_BMBRDsIgDADQE0FhuGI9gH_-eINKC85Yt9glJp5-77nvm18AvEQ2_q8f_nlsq4G9fXwXgcV4qMPteq-FMNdzQZhxwt5JQqoyhZOkObBiC61jypofSIXia9NxBAAA__8-jpg.webp)
$309,900
4249 E WEEPING WILLOW CIR, Winter Springs, FL 32708
Listed by CHARLES RUTENBERG REALTY ORLANDO
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![204 S MOSS RD, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRS5113329/65a019d5/1730252769/w600_original_BMBRDsIwCADQE7W4dh3gAfzzxxsgkjojbpEmJp5-7znGHmeAqFlc_ttHfpF1c_B39O_6gNWlW8D1csOKxIUJYZFW7qVNSStbmnFeElG1pNbohELIOuXXbv0IAAD__w-jpg.webp)
$2,500
204 S MOSS RD, Winter Springs, FL 32708
Listed by FLORIDA FIVE STAR REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1111 TROTWOOD BLVD, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6252313/404e9dad/1733858177/w600_original_BMBRDsIwCADQE7XElVrwAP754w1go3VG3CJLTDy973Ece1wAomRx-W1v-UaeNwd_xfisC6wuwwJu13srjJUmZNCF29xPlOTMlpA6Jy1aUy1tMiKkrpKfu41_AAAA__8-jpg.webp)
$552,500
1111 TROTWOOD BLVD, Winter Springs, FL 32708
Listed by BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![504 SAN GABRIEL CT, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRG5088562/547c79d9/1729807271/w600_original_BMBRDsIgDADQE0GZULt6AP_88QYFOpyxbrFLTDy973Ecu18APEcx-W1v-Xpsm4G9fHzWDqvJUIfb9U6ZS6LMBFlnnbBgWOpcQuGJQ-XlHE6NuPaUOmKLz13HPwAA__8-jpg.webp)
$295,000
504 SAN GABRIEL CT, Winter Springs, FL 32708
Listed by OLYMPUS EXECUTIVE REALTY INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![535 CRIMSON LN, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6251030/43e3f80a/1729562469/w600_original_BMBRDsIwCADQE7W0tATmAfzzxxsgm3VG3CJLTDy973Ece5wAomV1_W1v_Ua2zcFfMT7rDKvrWAIu5yu3qWIRJGiGWjqVJHrj1AU5iSGlqeIsTFXu1vNzX8Y_AAD__w-jpg.webp)
$400,000
535 CRIMSON LN, Winter Springs, FL 32708
Listed by KELLER WILLIAMS WINTER PARK
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![50 SHEOAH BLVD #34, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6250683/8f078dbf/1729543575/w600_original_BMBRDsIwCADQE7V0gGH1AP754w2wljojbpElJp5-77nvW5wBgrK6_teP_iK31cHfMb7LAxbX0QOul5tQLcRCE7ChVDNM9dQp8X1qSeciqdjcEIspi-XX1scRAAD__w-jpg.webp)
$160,000
50 SHEOAH BLVD #34, Winter Springs, FL 32708
Listed by PAINE-ANDERSON PROPERTIES, INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1198 GULFSTAR DR, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRV4939008/faf31abb/1729534575/w600_original_BMBRDoIwDADQE3WFrdDVA_jnjzfoYEyMFWKXmHh636P30y-InoKa_o63fj0sh6G9vH32FXfTVh1v1zunLDIPQrjFMSemEVhjAaozQeEiENdhkizTxguF51nbPwAA__8-jpg.webp)
$479,900
1198 GULFSTAR DR, Winter Springs, FL 32708
Listed by GLORY INTL. REAL ESTATE CO
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![311 STREAMVIEW WAY, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6249652/5ce12f2d/1731523623/w600_original_BMBRDsIwCADQE7WgsLZ4AP_88QY4WZ0Rt0gTE0_ve4yxxwkgKKvrb3vrN_K8Ofgr-me9w-raLeByvlZqlYkLwSJFjqZzaoxT4tIwiUhNN8WJVXhBO-Tnbv0fAAD__w-jpg.webp)
$2,975
311 STREAMVIEW WAY, Winter Springs, FL 32708
Listed by COLDWELL BANKER RESIDENTIAL RE
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1174 SPOTTED SANDPIPER LOOP, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6249843/1365b144/1729180873/w600_original_BMBRDsIgDAbgE0HXwQA9gG--eIM_0uKMdYtdYuLp_R7HsfuZyFOE4be98fV434zs5eOzdloNQ5yul1tNrbalTpV6EdVZOfCMEnKbcjgxSlg6WHpOquD43GX8AwAA__8-jpg.webp)
$2,590
1174 SPOTTED SANDPIPER LOOP, Winter Springs, FL 32708
Listed by SUNSHINE GROUP USA, INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![1349 MILL STREAM LN, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6249447/2d98af17/1729116068/w600_original_BMBRDsIgDADQE0GBjtB6AP_88QYda3DGusWSmHh632PO0y8AjlFMfsdbvh77YWAvH599g91kqMPtem9ILeWWCRR76UwpcElrWBgxUM01lIKovC11zRyfp45_AAAA__8-jpg.webp)
$385,000
1349 MILL STREAM LN, Winter Springs, FL 32708
Listed by WATSON REALTY CORP
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![336 SAN MIGUEL ST, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6248771/1404cbc6/1728798368/w600_original_BMBRDoIwDAbgE20dHXPOA_jmizf4C2VirBBLYuLp_R7HsfuFyHOE4be98fU4bUb28v5ZZ1oNXZ1u13vN51K4pIEWGXPLE4cZCWGsgwZZWEOSVJnbSRoQn7v2fwAAAP__-jpg.webp)
$1,600
336 SAN MIGUEL ST, Winter Springs, FL 32708
Listed by ROMAN'S PRO REALTY LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![413 DAVID ST, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6248491/70bfc0b2/1728570669/w600_original_BMBRDsIgDADQE0HblcHmAfzzxxuUijhj3WJJTDy97zHG4ScA5ygmv_0tX4-6G9jL-2e7wWbSm8PlfC28pDwXRsBaJtVpCWtmConaHCTdKfBakbJiRaX4PFr_BwAA__8-jpg.webp)
$1,890
413 DAVID ST, Winter Springs, FL 32708
Listed by MAIN STREET RENEWAL LLC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![411 BOXWOOD CIR, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6247758/aa09a64c/1730140276/w600_original_BMBRDsIgDADQE0FlA7p6AP_88QZdqThj3WJJTDy97zHG4WcAnyMb__Y3fz3KbmAv75-twWbc1eF6ueG8TJWmXECFuLSMQe-8hLzWNXBtEhKiUDqVVEjj89D-DwAA__8-jpg.webp)
$345,900
411 BOXWOOD CIR, Winter Springs, FL 32708
Listed by RE/MAX EXCLUSIVE COLLECTION
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![423 SHEOAH BLVD #19, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6247738/64676216/1728145871/w600_original_BMBdDsIgDADgE0EdjNF4AN988QasPzhj3WJJTDz9vucYh18BPMdm7b9_2s8j7Qb29v7dGDZrXRzut0fNmJYJsQLrXNfMaxC8aJhpKgEJS9ClJlFiLinH1yH9DAAA__8-jpg.webp)
$1,650
423 SHEOAH BLVD #19, Winter Springs, FL 32708
Listed by PAINE-ANDERSON PROPERTIES, INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![381 S MOSS RD, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6244688/55686e7c/1727964973/w600_original_BMDdDYJADADgie569EfUAXzzxQ1KaU6MFWJJTJye77nvW14BkqqG_teP_rLaGhDv7N9lhiW0e8L99hhpZB6EG7ijnk_TVAY0KmytFW0kZRZkuRAaItfX5v0IAAD__w-jpg.webp)
$1,249,900
381 S MOSS RD, Winter Springs, FL 32708
Listed by LAUREATE PARK REALTY
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)
![888 CHOKECHERRY DR, Winter Springs, FL 32708](https://img.chime.me/imageemb/mls-listing/586/MFRO6247352/b8297459/1728013603/w600_original_BMBRDoIwDAbgE21lK6ObB_DNF2_wa3FirBBLYuLp-Z77vvmJyDnC8F8_-Hm8r0b29v5dlBZDn50u56twTZwmYUKr6dFUg0hGGKfCodasoeSbDGNDGRria5v7EQAA__8-jpg.webp)
$449,900
888 CHOKECHERRY DR, Winter Springs, FL 32708
Listed by SOUTHERN PRESTIGE REALTY INC
![Stellar MLS](https://cdn.chime.me/image/fs/sitebuild/2019724/10/h80_original_2135182e-0cfe-4d4c-baf8-af78ae782892-png.webp)