Revolutionizing · Modernizing · SimplifyingRevolutionizing · Modernizing · Simplifying63 homes sold in the last twelve months, median $1,090,000, a median of 130 days to sell. What they closed at, not what was asked.
Sold prices in Winter Park ran from $352,000 to $2,910,156, on a median home of about 1,436 square feet with 3 bedrooms. The most recent sale recorded here closed on 14 Aug 2026.
Of the 63 homes that sold in Winter Park with a recorded asking price over the last twelve complete months, 5 went for more than the seller asked and 45 went for less. The typical sale landed at 98% of asking.
| Home | Sold | Sold price | Asking | % of asking | Per sq ft | Days to sell |
|---|---|---|---|---|---|---|
| 189 County Road 702 Unit 5-2022 bd · 2 ba · 940 sq ft · built 1978Condominium | 14 Aug 2026 | $575,000 | $589,000 | 98% | $612 | 84 |
| 310 Iron Horse Way Unit D50241 bd · 1 ba · 563 sq ft · built 1983Condominium | 7 Aug 2026 | $575,000 | $575,000 | 100% | $1,021 | 117 |
| 471 Hi Country Drive Unit 11-122 bd · 1 ba · 651 sq ft · built 1969Condominium | 31 Jul 2026 | $432,000 | $450,000 | 96% | $664 | 63 |
| 78321 Highway 40 Unit 222 bd · 3 ba · 1,130 sq ft · built 2018Condominium | 28 Jul 2026 | $769,000 | $785,000 | 98% | $681 | 88 |
| 185 Vasquez Unit B34 bd · 3 ba · 2,329 sq ft · built 2026Townhouse | 27 Jul 2026 | $1,925,000 | $1,975,000 | 97% | $827 | 167 |
| 64 Overlook Place4 bd · 5 ba · 3,057 sq ft · built 2023Single Family Residence | 17 Jul 2026 | $2,801,361 | $2,774,642 | 101% | $916 | 627 |
| 185 Vasquez Road Unit B14 bd · 3 ba · 2,476 sq ft · built 2025Townhouse | 14 Jul 2026 | $1,975,400 | $1,995,000 | 99% | $798 | 560 |
| 185 Vasquez Road Unit B54 bd · 3 ba · 2,476 sq ft · built 2025Townhouse | 13 Jul 2026 | $2,024,300 | $1,995,000 | 101% | $818 | 553 |
| 185 Vasquez Road Unit B24 bd · 3 ba · 2,314 sq ft · built 2025Townhouse | 13 Jul 2026 | $1,966,800 | $1,950,000 | 101% | $850 | 552 |
| 185 Vasquez Road Unit B44 bd · 3 ba · 2,329 sq ft · built 2026Townhouse | 10 Jul 2026 | $1,911,300 | $1,950,000 | 98% | $821 | 246 |
| 41 Forest Trail Unit 73 bd · 3 ba · 1,764 sq ft · built 1983Condominium | 9 Jul 2026 | $1,005,000 | $1,025,000 | 98% | $570 | 48 |
| 765 Elk Trail4 bd · 3 ba · 2,489 sq ft · built 2000Single Family Residence | 2 Jul 2026 | $1,827,925 | $1,850,000 | 99% | $734 | 19 |
| 35 Sunny Ridge Lane3 bd · 4 ba · 2,404 sq ft · built 2023Single Family Residence | 23 Jun 2026 | $2,366,097 | $2,366,327 | 100% | $984 | 243 |
| 144 Ski Idlewild Road Unit 22032 bd · 2 ba · 1,030 sq ft · built 2022Condominium | 18 Jun 2026 | $990,000 | $1,037,000 | 95% | $962 | 101 |
| 185 Vasquez Road Unit 54 bd · 4 ba · 2,476 sq ft · built 2025Townhouse | 10 Jun 2026 | $1,908,800 | $1,910,000 | 100% | $771 | 604 |
| 115 Bear Trail Court3 bd · 3 ba · 2,145 sq ft · built 2006Townhouse | 3 Jun 2026 | $1,230,000 | $1,295,000 | 95% | $573 | 61 |
| 572 Telemark Court Unit 5723 bd · 2 ba · 1,536 sq ft · built 2006Condominium | 22 May 2026 | $1,150,000 | $1,199,000 | 96% | $749 | 88 |
| 357 Hi Country Drive Unit 12 bd · 2 ba · 1,051 sq ft · built 1978Condominium | 20 May 2026 | $589,000 | $589,000 | 100% | $560 | 151 |
| 580 Winter Park Drive Unit 44742 bd · 2 ba · 991 sq ft · built 2007Condominium | 15 May 2026 | $944,000 | $949,000 | 99% | $953 | 35 |
| 801 Trailhead Circle Unit 8133 bd · 3 ba · 1,485 sq ft · built 2008Condominium | 4 May 2026 | $1,150,000 | $1,180,000 | 97% | $774 | 45 |
| 401 Nystrom Lane Unit 15113 bd · 3 ba · 1,525 sq ft · built 1999Condominium | 9 Apr 2026 | $1,441,661 | $1,475,000 | 98% | $945 | 31 |
| 374 Lake Trail3 bd · 3 ba · 1,306 sq ft · built 2024Townhouse | 3 Apr 2026 | $969,000 | $1,099,000 | 88% | $742 | 247 |
| 38 Wheeler Road4 bd · 4 ba · 2,115 sq ft · built 2025Townhouse | 1 Apr 2026 | $1,595,000 | $1,595,000 | 100% | $754 | 106 |
| 78415 US Highway 40 Unit 22 bd · 2 ba · 1,335 sq ft · built 2022Condominium | 31 Mar 2026 | $772,000 | $777,000 | 99% | $578 | 49 |
| 220 Village Drive Unit 2032 bd · 2 ba · 940 sq ft · built 1980Condominium | 31 Mar 2026 | $549,000 | $549,000 | 100% | $584 | 33 |
| 313 N Woods Place4 bd · 5 ba · 2,972 sq ft · built 2020Townhouse | 30 Mar 2026 | $2,700,000 | $2,850,000 | 95% | $908 | 68 |
| 115 Wheeler Road3 bd · 4 ba · 1,870 sq ft · built 2025Townhouse | 24 Mar 2026 | $1,450,000 | $1,450,000 | 100% | $775 | 162 |
| 203 Antler Way Unit 2-2033 bd · 3 ba · 1,742 sq ft · built 2002Townhouse | 23 Mar 2026 | $1,225,000 | $1,225,000 | 100% | $703 | 110 |
| 294 Vasquez Road3 bd · 2 ba · 1,120 sq ft · built 1964Single Family Residence | 12 Mar 2026 | $920,000 | $1,015,000 | 91% | $821 | 70 |
| 273 Hi Country Drive Unit 15121 bd · 1 ba · 460 sq ft · built 1971Condominium | 4 Mar 2026 | $389,500 | $399,000 | 98% | $847 | 380 |
| 246 Hi Country Drive Unit 32 bd · 2 ba · 935 sq ft · built 1978Condominium | 2 Mar 2026 | $625,000 | $625,000 | 100% | $668 | 327 |
| 189 Pine Cone Lane6 bd · 5 ba · 4,268 sq ft · built 1977Single Family Residence | 27 Feb 2026 | $2,500,000 | $2,500,000 | 100% | $586 | 260 |
| 580 Winter Park Drive Unit 43572 bd · 2 ba · 900 sq ft · built 2007Condominium | 20 Feb 2026 | $925,000 | $945,000 | 98% | $1,028 | 588 |
| 165 Whistlestop Circle4 bd · 6 ba · 2,840 sq ft · built 2025Townhouse | 18 Feb 2026 | $1,900,000 | $1,955,000 | 97% | $669 | 138 |
| 509 Summit Place4 bd · 5 ba · 3,186 sq ft · built 2017Single Family Residence | 13 Feb 2026 | $2,721,211 | $2,875,000 | 95% | $854 | 104 |
| 300 Kings Crossing Road Unit B33 bd · 3 ba · 1,378 sq ft · built 1980Condominium | 12 Feb 2026 | $770,000 | $815,000 | 94% | $559 | 153 |
| 215 Bear Trail Court3 bd · 4 ba · 2,184 sq ft · built 2006Townhouse | 8 Jan 2026 | $1,400,000 | $1,450,000 | 97% | $641 | 160 |
| 510 Kings Crossing Unit C 2022 bd · 2 ba · 813 sq ft · built 1978Condominium | 17 Dec 2025 | $535,000 | $535,000 | 100% | $658 | 55 |
| 670 Winter Park Drive Unit 33022 bd · 2 ba · 1,047 sq ft · built 2007Condominium | 16 Dec 2025 | $925,600 | $950,000 | 97% | $884 | 255 |
| 128 GCR 702 Unit 4-1042 bd · 2 ba · 850 sq ft · built 1976Condominium | 24 Nov 2025 | $577,500 | $599,900 | 96% | $679 | 293 |
| 378 Lake Trail3 bd · 3 ba · 1,948 sq ft · built 2024Townhouse | 21 Nov 2025 | $1,379,000 | $1,399,000 | 99% | $708 | 116 |
| 432 Hi Country Drive Unit 151 bd · 1 ba · 465 sq ft · built 1970Condominium | 21 Nov 2025 | $405,000 | $415,000 | 98% | $871 | 155 |
| 294 Lions Gate Drive3 bd · 3 ba · 1,436 sq ft · built 2017Townhouse | 14 Nov 2025 | $1,180,000 | $1,265,000 | 93% | $822 | 168 |
| 377 Hi Country Drive Unit 62 bd · 2 ba · 960 sq ft · built 1976Condominium | 12 Nov 2025 | $594,900 | $594,900 | 100% | $620 | 149 |
| 1080 Winter Park Drive Unit 172 bd · 2 ba · 1,377 sq ft · built 1981Condominium | 10 Nov 2025 | $761,250 | $799,000 | 95% | $553 | 68 |
| 175 Whistlestop Circle4 bd · 5 ba · 2,650 sq ft · built 2025Townhouse | 7 Nov 2025 | $1,762,000 | $1,795,000 | 98% | $665 | 212 |
| 720 Baker Drive Unit 2103 bd · 3 ba · 1,483 sq ft · built 2025Condominium | 6 Nov 2025 | $1,090,000 | $1,200,000 | 91% | $735 | 274 |
| 125 Whistlestop Circle4 bd · 6 ba · 2,905 sq ft · built 2025Townhouse | 4 Nov 2025 | $1,975,000 | $2,000,000 | 99% | $680 | 130 |
| 455 Bear Trail3 bd · 4 ba · 2,184 sq ft · built 2006Townhouse | 31 Oct 2025 | $1,310,000 | $1,310,000 | 100% | $600 | 35 |
| 144 Ski Idlewild Road Unit 24032 bd · 2 ba · 1,030 sq ft · built 2022Condominium | 24 Oct 2025 | $1,075,000 | $1,100,000 | 98% | $1,044 | 24 |
| 79114 US Highway 40 Unit E2011 ba · 439 sq ft · built 1986Condominium | 21 Oct 2025 | $352,000 | $369,000 | 95% | $802 | 292 |
| 71 Overlook Place4 bd · 4 ba · 3,361 sq ft · built 2024Single Family Residence | 16 Oct 2025 | $2,910,156 | $2,893,346 | 101% | $866 | 353 |
| 78491 US Highway 40 Unit 52 bd · 1 ba · 1,125 sq ft · built 1995Condominium | 14 Oct 2025 | $470,000 | $499,000 | 94% | $418 | 89 |
| 288 Lions Gate Drive3 bd · 3 ba · 1,436 sq ft · built 2017Townhouse | 10 Oct 2025 | $1,160,000 | $1,190,000 | 97% | $808 | 124 |
| 507 Hi Country Drive Unit 7-873 bd · 2 ba · 804 sq ft · built 1969Condominium | 1 Oct 2025 | $645,000 | $630,000 | 102% | $802 | 96 |
| 147 Forest Trail Unit 32 bd · 2 ba · 1,002 sq ft · built 1999Condominium | 26 Sep 2025 | $698,500 | $715,000 | 98% | $697 | 126 |
| 12 Wheeler Road3 bd · 3 ba · 2,124 sq ft · built 2025Townhouse | 25 Sep 2025 | $1,625,000 | $1,625,000 | 100% | $765 | 91 |
| 65 Lake Trail Court3 bd · 4 ba · 2,900 sq ft · built 2005Townhouse | 25 Sep 2025 | $1,550,000 | $1,625,000 | 95% | $534 | 175 |
| 247 Hi Country Drive Unit 161 bd · 1 ba · 492 sq ft · built 1971Condominium | 25 Sep 2025 | $410,000 | $413,000 | 99% | $833 | 140 |
| 217 Van Anderson Drive Unit 62 bd · 2 ba · 847 sq ft · built 1971Condominium | 23 Sep 2025 | $455,000 | $475,000 | 96% | $537 | 202 |
| Month | Homes sold | Median sold price | |
|---|---|---|---|
| Sep 2025 | 8 | $661,750 | |
| Oct 2025 | 7 | $1,075,000 | |
| Nov 2025 | 9 | $1,090,000 | |
| Dec 2025 | 2 | $730,300 | |
| Jan 2026 | 1 | $1,400,000 | |
| Feb 2026 | 5 | $1,900,000 | |
| Mar 2026 | 8 | $846,000 | |
| Apr 2026 | 3 | $1,441,661 | |
| May 2026 | 4 | $1,047,000 | |
| Jun 2026 | 4 | $1,569,400 | |
| Jul 2026 | 10 | $1,918,150 | |
| Aug 2026 | 2 | $575,000 |
| Sold price | Sold | Share | Median per sq ft |
|---|---|---|---|
| $300k to $500k | 8 | 13% | $770 |
| $500k to $750k | 11 | 17% | $668 |
| $750k to $1M | 10 | 16% | $782 |
| $1M to $1.5M | 14 | 22% | $742 |
| $1.5M and up | 20 | 32% | $784 |
| Bedrooms | Sold | Share | Median sold |
|---|---|---|---|
| 1 bedroom | 4 | 6% | $407,500 |
| 2 bedrooms | 21 | 34% | $625,000 |
| 3 bedrooms | 21 | 34% | $1,225,000 |
| 4 bedrooms | 15 | 24% | $1,966,800 |
| 5+ bedrooms | 1 | 2% | $2,500,000 |
| Kind of home | Sold | Share | Median sold |
|---|---|---|---|
| Condominium | 33 | 52% | $625,000 |
| Townhouse | 23 | 37% | $1,598,307 |
| Single Family Residence | 7 | 11% | $2,500,000 |
Each of these neighbourhoods has its own guide, with what the area is like to live in and what is for sale there now.
Winter Park sits in Grand County. These towns have their own sold pages:
This page is what already sold. These cover what is on the market there now.
The median home in Winter Park sold for $1,090,000, about $742 per square foot, across 63 sales over the last twelve complete calendar months. Sold prices ran from $352,000 to $2,910,156.
2 homes closed in Winter Park in the last 30 days and 15 in the last 90, out of 63 over the last twelve complete months. The most recent sale recorded here closed on 14 Aug 2026.
The typical Winter Park sale closed at 98% of the asking price. Of 63 sales with a recorded asking price, 5 (8%) sold for MORE than the seller asked, 13 sold at asking and 45 sold below it.
A median of 130 days in Winter Park, measured from the listing contract date to the closing date, across the last twelve complete months.
They answer different questions. Homes on the market in Winter Park are asking a median of $1,247,500; homes that actually closed went for a median of $1,090,000. A sold price is what somebody paid; an asking price is what somebody hopes for.
It is computed the moment you open this page, straight from the live MLS feed - not a monthly report. Residential sales only; rentals, land, commercial and fractional co-ownership shares are excluded so they cannot distort the medians.
Every figure on this page is computed from the live MLS feed at the moment the page loads, not published monthly and left to go stale. "Last twelve months" means the last twelve COMPLETE calendar months, the same window the market reports use, so the two never disagree; the 30- and 90-day counts are rolling. Figures cover residential sales only - rentals, land and commercial are excluded, as are fractional co-ownership shares, which are priced per share and would distort the medians. Days to sell is measured from the listing contract date to the closing date. Sold data is deemed reliable but not guaranteed - talk to us before making a decision on it.