Winter Springs, FL Price Reductions
A price reduction is the clearest signal a seller sends: the first number did not work. This tracker lists every Winter Springs listing that lowered its asking price, updated nightly from the live MLS record — the old price, the new price, the size of the cut and how long the home has been on the market — so buyers can see where sellers are moving and sellers can see what their competition just did.
14 homes for sale in Winter Springs, FL cut their asking price in the last 7 days and 42 in the last 30, out of 132 active listings (25% reduced at least once this month). The median reduction is 2.1% ($10,000). The largest cut this week was $35,000 on 133 Redtail Place in Winter Springs ($510,000 → $475,000).
Latest price reductions in Winter Springs
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 711 Thistle Place Oct 14 · 3 bd · 2 ba · 960 sf | — | $284,900 | $279,900 | −1.8% | 12 |
| 654 Cypress Lane Oct 14 · 3 bd · 2 ba · 1,201 sf | — | $325,000 | $322,500 | −0.8% | 28 |
| 116 Partridge Circle Oct 13 · 3 bd · 2.5 ba · 2,272 sf | — | $624,500 | $599,000 | −4.1% | 25 |
| 131 Kristi Ann Court Oct 13 · 2 bd · 1.5 ba · 898 sf | Moss Cove | $206,999 | $206,499 | −0.2% | 16 |
| 248 Huntridge Way Oct 12 · 4 bd · 3 ba · 2,840 sf | — | $629,900 | $595,000 | −5.5% | 47 |
| 1041 Northern Way Oct 12 · 5 bd · 3.5 ba · 3,014 sf | — | $989,000 | $969,000 | −2.0% | 17 |
| 992 Sleeping Rock Court Oct 11 · 4 bd · 2.5 ba · 2,701 sf | tuscawilla | $750,000 | $725,000 | −3.3% | 4 |
| 227 Mcleods Way Oct 10 · 3 bd · 3.5 ba · 1,872 sf | Jesups Reserve Townhomes | $390,000 | $387,500 | −0.6% | 78 |
| 133 Redtail Place Oct 9 · 3 bd · 2 ba · 1,978 sf | — | $510,000 | $475,000 | −6.9% | 55 |
| 700 Castlewood Drive Oct 9 · 3 bd · 2 ba · 1,366 sf | — | $275,000 | $269,900 | −1.9% | 13 |
| 728 Ridgewood Way Oct 9 · 3 bd · 2 ba · 1,366 sf | — | $275,000 | $269,900 | −1.9% | 13 |
| 992 Sleeping Rock Court Oct 8 · 4 bd · 2.5 ba · 2,701 sf | tuscawilla | $779,000 | $750,000 | −3.7% | 4 |
| 288 Ringwood Drive Oct 8 · 3 bd · 2 ba · 1,700 sf | deer run casselberry | $460,000 | $450,000 | −2.2% | 28 |
| 1041 Northern Way Oct 7 · 5 bd · 3.5 ba · 3,014 sf | — | $999,000 | $989,000 | −1.0% | 17 |
| 476 Club Drive Oct 6 · 3 bd · 2 ba · 1,460 sf | Cypress Club | $267,500 | $250,000 | −6.5% | 151 |
| 50 Sheoah Boulevard #33 Oct 6 · 2 bd · 2 ba · 972 sf | — | $167,777 | $154,950 | −7.6% | 117 |
| 70 Moree Loop #61 Oct 6 · 2 bd · 1.5 ba · 1,080 sf | — | $179,900 | $178,900 | −0.6% | 47 |
| 629 Alton Road Oct 2 · 3 bd · 2 ba · 1,210 sf | — | $384,900 | $374,900 | −2.6% | 69 |
| 417 Sheoah Boulevard #17 Oct 2 · 2 bd · 2 ba · 936 sf | — | $170,000 | $166,000 | −2.4% | 22 |
| 142 Bayberry Court Oct 1 · 4 bd · 2 ba · 1,425 sf | — | $359,000 | $355,000 | −1.1% | 85 |
| 1610 Fox Glen Court Sep 30 · 4 bd · 2.5 ba · 1,992 sf | Fox Glen At Chelsea Parc Tuscawilla | $497,000 | $486,900 | −2.0% | 21 |
| 1112 Orange Avenue Sep 29 · 5 bd · 6.5 ba · 8,685 sf | Lake Jessup | $3,998,000 | $3,700,000 | −7.5% | 388 |
| 1357 Mill Stream Lane Sep 29 · 3 bd · 2.5 ba · 1,606 sf | Jesups Landing | $390,000 | $384,000 | −1.5% | 103 |
| 909 Devon Creek Road Sep 29 · 4 bd · 3 ba · 2,256 sf | parkstone | $499,900 | $497,500 | −0.5% | 19 |
| 864 Bentley Green Circle Sep 28 · 4 bd · 3 ba · 2,272 sf | Bentley Club At Bentley Green | $799,000 | $699,000 | −12.5% | 16 |
| 288 Ringwood Drive Sep 28 · 3 bd · 2 ba · 1,700 sf | deer run casselberry | $475,000 | $460,000 | −3.2% | 28 |
| 717 Adidas Road Sep 28 · 2 bd · 2 ba · 1,812 sf | Wedgewood Tennis Villas | $414,900 | $399,900 | −3.6% | 100 |
| 212 S Cortez Avenue Sep 27 · 4 bd · 3 ba · 1,680 sf | — | $375,000 | $369,900 | −1.4% | 68 |
| 744 Barrington Circle Sep 25 · 3 bd · 2 ba · 1,658 sf | — | $425,000 | $409,000 | −3.8% | 25 |
| 248 Huntridge Way Sep 25 · 4 bd · 3 ba · 2,840 sf | — | $644,900 | $629,900 | −2.3% | 47 |
| 709 Sailfish Road Sep 25 · 3 bd · 2 ba · 1,737 sf | — | $392,500 | $387,500 | −1.3% | 280 |
| 156 Seville Chase Drive Sep 25 · 4 bd · 3 ba · 2,509 sf | Seville Chase | $649,000 | $647,500 | −0.2% | 166 |
| 864 Bentley Green Circle Sep 24 · 4 bd · 3 ba · 2,272 sf | Bentley Club At Bentley Green | $879,000 | $799,000 | −9.1% | 16 |
| 506 Club Drive Sep 24 · 2 bd · 2 ba · 1,002 sf | Cypress Club | $215,000 | $199,000 | −7.4% | 307 |
| 1714 Fox Glen Court Sep 23 · 3 bd · 2 ba · 1,484 sf | Fox Glen At Chelsea Parc Tuscawilla | $439,000 | $429,000 | −2.3% | 37 |
| 498 Green Spring Cir Sep 22 · 2 bd · 1.5 ba · 1,363 sf | — | $249,000 | $244,000 | −2.0% | 107 |
| 227 Mcleods Way Sep 19 · 3 bd · 3.5 ba · 1,872 sf | Jesups Reserve Townhomes | $392,500 | $390,000 | −0.6% | 78 |
| 864 Bentley Green Circle Sep 18 · 4 bd · 3 ba · 2,272 sf | Bentley Club At Bentley Green | $930,000 | $879,000 | −5.5% | 16 |
| 1714 Fox Glen Court Sep 18 · 3 bd · 2 ba · 1,484 sf | Fox Glen At Chelsea Parc Tuscawilla | $449,000 | $439,000 | −2.2% | 37 |
| 335 Kirkcaldy Drive Sep 18 · 3 bd · 2 ba · 1,178 sf | Highland Village | $329,900 | $324,900 | −1.5% | 135 |
| 662 Nighthawk Circle Sep 17 · 3 bd · 3 ba · 1,583 sf | Greenspointe | $374,900 | $374,400 | −0.1% | 37 |
| 717 Adidas Road Sep 16 · 2 bd · 2 ba · 1,812 sf | Wedgewood Tennis Villas | $419,900 | $414,900 | −1.2% | 100 |
Biggest cuts this week
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 133 Redtail Place Oct 9 · 3 bd · 2 ba · 1,978 sf | — | $510,000 | $475,000 | −6.9% | 55 |
| 248 Huntridge Way Oct 12 · 4 bd · 3 ba · 2,840 sf | — | $629,900 | $595,000 | −5.5% | 47 |
| 992 Sleeping Rock Court Oct 8 · 4 bd · 2.5 ba · 2,701 sf | tuscawilla | $779,000 | $750,000 | −3.7% | 4 |
| 116 Partridge Circle Oct 13 · 3 bd · 2.5 ba · 2,272 sf | — | $624,500 | $599,000 | −4.1% | 25 |
| 992 Sleeping Rock Court Oct 11 · 4 bd · 2.5 ba · 2,701 sf | tuscawilla | $750,000 | $725,000 | −3.3% | 4 |
| 1041 Northern Way Oct 12 · 5 bd · 3.5 ba · 3,014 sf | — | $989,000 | $969,000 | −2.0% | 17 |
| 1041 Northern Way Oct 7 · 5 bd · 3.5 ba · 3,014 sf | — | $999,000 | $989,000 | −1.0% | 17 |
| 288 Ringwood Drive Oct 8 · 3 bd · 2 ba · 1,700 sf | deer run casselberry | $460,000 | $450,000 | −2.2% | 28 |
| 700 Castlewood Drive Oct 9 · 3 bd · 2 ba · 1,366 sf | — | $275,000 | $269,900 | −1.9% | 13 |
| 728 Ridgewood Way Oct 9 · 3 bd · 2 ba · 1,366 sf | — | $275,000 | $269,900 | −1.9% | 13 |
Communities with the most reductions (30 days)
| Community | City | Reductions | Median cut |
|---|---|---|---|
| Bentley Club At Bentley Green | Winter Springs | 3 | −9.1% |
| Fox Glen At Chelsea Parc Tuscawilla | Winter Springs | 3 | −2.2% |
| Jesups Reserve Townhomes | Winter Springs | 2 | −0.6% |
| deer run casselberry | Winter Springs | 2 | −2.7% |
| Wedgewood Tennis Villas | Winter Springs | 2 | −2.4% |
| Cypress Club | Winter Springs | 2 | −7.0% |
| tuscawilla | Winter Springs | 2 | −3.5% |
How to read this
Reductions are detected by comparing each listing’s asking price night over night in the MLS feed; a listing appears once per cut, and the share reduced counts each listing once. Relists at a new price under a new MLS number are not matched. Prices are asking prices. Source: live MLS feeds compiled by Momentum Research, updated October 14, 2026.