Homes under $300K in Winter Springs, FL

20 for sale · 80 homes listed · Updated September 27, 2026 · Page 1 of 2

• 311 san miguel street, Winter Springs 32708 $178,900 · 2 bd · 2 ba · 945 sqft
• 499 club drive, Winter Springs 32708 $210,000 · 2 bd · 2 ba · 1,224 sqft
• 600 northern way #201, Winter Springs 32708 $274,900 · 3 bd · 2 ba · 1,425 sqft
• 299 woodgreen lane, Winter Springs 32708 $275,000 · 3 bd · 3 ba · 1,326 sqft
• 240 moree loop #3, Winter Springs 32708 $170,000 · 3 bd · 2 ba · 1,187 sqft
• 417 sheoah boulevard #17, Winter Springs 32708 $170,000 · 2 bd · 2 ba · 936 sqft
• 412 horizon drive, Winter Springs 32708 $284,000 · 3 bd · 2 ba · 1,101 sqft
• 343 san miguel street #343, Winter Springs 32708 $145,000 · 2 bd · 2 ba · 945 sqft
• 600 northern way #1108, Winter Springs 32708 $257,500 · 3 bd · 3 ba · 1,411 sqft
• 207 birch terrace, Winter Springs 32708 $297,000 · 3 bd · 2 ba · 1,318 sqft
• 506 club drive, Winter Springs 32708 $199,000 · 2 bd · 2 ba · 1,002 sqft
• 498 green spring circle, Winter Springs 32708 $244,000 · 2 bd · 2 ba · 1,363 sqft
• 130 rhoden lane, Winter Springs 32708 $220,000 · 2 bd · 2 ba · 896 sqft
• 736 summerland drive, Winter Springs 32708 $295,900 · 3 bd · 2 ba · 1,298 sqft
• 728 ridgewood way, Winter Springs 32708 $275,000 · 3 bd · 2 ba · 1,366 sqft
• 272 san gabriel street, Winter Springs 32708 $275,000 · 3 bd · 2 ba · 1,105 sqft
• 1453 casa park circle, Winter Springs 32708 $244,999 · 2 bd · 2 ba · 1,156 sqft
• 311 san miguel street #311, Winter Springs 32708 $178,900 · 2 bd · 2 ba · 945 sqft
• 429 sheoah boulevard #9, Winter Springs 32708 $199,000 · 3 bd · 2 ba · 1,187 sqft
• 131 kristi ann court, Winter Springs 32708 $206,999 · 2 bd · 2 ba · 898 sqft
• 510 green spring circle, Winter Springs 32708 Pending $211,000 · 2 bd · 3 ba · 1,180 sqft
• 600 northern way 1804, Winter Springs 32708 Pending $290,000 · 4 bd · 3 ba · 1,726 sqft
• 162 constitution way, Winter Springs 32708 Pending $289,900 · 3 bd · 3 ba · 1,468 sqft
• 3880 white birch run, Winter Springs 32708 Pending $263,000 · 3 bd · 3 ba · 1,306 sqft
• 476 tradition lane, Winter Springs 32708 Pending $280,000 · 3 bd · 3 ba · 1,468 sqft
• 600 northern way 502, Winter Springs 32708 Active Under Contract $249,900 · 3 bd · 2 ba · 1,425 sqft
• 411 green spring circle, Winter Springs 32708 Active Under Contract $199,900 · 3 bd · 2 ba · 1,130 sqft
• 4431 brook hollow circle, Winter Springs 32708 Active Under Contract $220,000 · 3 bd · 2 ba · 1,367 sqft
• 120 north fairfax avenue, Winter Springs 32708 Active Under Contract $214,000 · 2 bd · 1 ba · 1,148 sqft
• 4490 brook hollow circle, Winter Springs 32708 Active Under Contract $230,000 · 3 bd · 2 ba · 1,359 sqft
• 180 constitution way, Winter Springs 32708 Active Under Contract $294,999 · 2 bd · 3 ba · 1,275 sqft
• 603 casa park court g, Winter Springs 32708 Active Under Contract $244,900 · 2 bd · 3 ba · 1,156 sqft
• 504 green spring circle, Winter Springs 32708 Active Under Contract $235,000 · 2 bd · 3 ba · 1,363 sqft
• 71 bombay avenue, Winter Springs 32708 Active Under Contract $205,900 · 2 bd · 2 ba · 1,134 sqft
• 1393 san diego court, Winter Springs 32708 Active Under Contract $296,000 · 2 bd · 2 ba · 987 sqft
• 118 deer song drive, Winter Springs 32708 Active Under Contract $230,000 · 3 bd · 2 ba · 1,105 sqft
• 600 northern way 906, Winter Springs 32708 Active Under Contract $288,000 · 3 bd · 3 ba · 1,609 sqft
• 236 panorama drive, Winter Springs 32708 Active Under Contract $279,900 · 3 bd · 2 ba · 1,161 sqft
• 1329 heritage commons drive, Winter Springs 32708 Active Under Contract $287,500 · 3 bd · 3 ba · 1,492 sqft
• 220 moree loop 1, Winter Springs 32708 Active Under Contract $130,000 · 1 bd · 1 ba · 710 sqft
• 284 woodgreen lane, Winter Springs 32708 Active Under Contract $175,000 · 2 bd · 2 ba · 1,108 sqft
• 526 seasons court, Winter Springs 32708 Active Under Contract $285,000 · 3 bd · 2 ba · 1,161 sqft
• 498 club drive, Winter Springs 32708 Off market since Jul 2026 $225,000 · 2 bd · 2 ba · 1,224 sqft
• 30 moree loop 39, Winter Springs 32708 Off market since Aug 2026 $210,000 · 3 bd · 3 ba · 1,400 sqft
• 270 san gabriel street, Winter Springs 32708 Off market since Sep 2026 $242,000 · 3 bd · 2 ba · 1,089 sqft
• 506 club drive, Winter Springs 32708 Off market since Sep 2026 $199,000 · 2 bd · 2 ba · 1,002 sqft
• 446 club drive, Winter Springs 32708 Off market since Sep 2026 $269,000 · 3 bd · 2 ba · 1,460 sqft
• 600 northern way 201, Winter Springs 32708 Off market since Sep 2026 $274,900 · 3 bd · 2 ba · 1,425 sqft
• 600 northern way 1608, Winter Springs 32708 Off market since Sep 2026 $272,000 · 3 bd · 2 ba · 1,425 sqft
• 421 horizon drive, Winter Springs 32708 Off market since Sep 2026 $285,000 · 3 bd · 2 ba · 1,069 sqft