Townhomes for Sale in Winter Park, FL
24 townhomes are for sale in Winter Park, FL as of 2026-09-06. The median list price is $575,000 ($318/sq ft), most townhomes list between $270K to $2.62M, and the median listing has been on the market 42 days. 7 townhomes came on the market this week and 357 sold in the last 12 months at a median of $447,000.
Newest townhomes for sale in Winter Park
The most recently listed homes in Winter Park, newest first, with photos. Each card opens the full listing with every photo, the community’s sales history and a tour request. Homes marked New listed in the last seven days.
Winter Park townhomes for sale by price
Every active listing in Winter Park grouped by price, with the newest listings in each band. The median is $575,000; the busiest band is $500K – $750K.
Under $200K: 1 home
$200K – $300K: 4 homes
- $285,000 · 3 bd / 2 ba / 1,467 sq ft · 2657 EXUMA WAY
- $270,000 · 3 bd / 3 ba / 1,803 sq ft · 2487 HARBOUR WAY
- $296,500 · 3 bd / 2 ba / 1,324 sq ft · 2339 INAGUA WAY
- $255,000 · 2 bd / 2 ba / 1,020 sq ft · 2651 CAYMAN WAY
$300K – $400K: 3 homes
- $305,000 · 3 bd / 2 ba / 1,467 sq ft · 2370 BARBADOS DRIVE
- $309,900 · 3 bd / 2.5 ba / 1,545 sq ft · 7530 CRANES CREEK COURT
- $365,000 · 3 bd / 2.5 ba / 1,861 sq ft · 7506 CRANES CREEK COURT #30
$500K – $750K: 8 homes
- $575,000 · 2 bd / 2.5 ba / 1,851 sq ft · 1071 ARAGON AVENUE
- $575,000 · 2 bd / 2.5 ba / 1,648 sq ft · 1259 INDIANA AVENUE (Townhomes/Harper Place)
- $575,000 · 2 bd / 2.5 ba / 1,704 sq ft · 2881 TEMPLE TRAIL
- $660,000 · 3 bd / 3 ba / 1,690 sq ft · 1256 MELISSA COURT
$750K – $1M: 2 homes
- $999,000 · 3 bd / 3 ba / 2,434 sq ft · 1138 S PENNSYLVANIA AVENUE (Virginia Heights)
- $810,000 · 3 bd / 3.5 ba / 2,030 sq ft · 1265 ARLINGTON PL (Virginia Hgts Rep)
$1M and up: 6 homes
- $3.15M · 3 bd / 4 ba / 3,244 sq ft · 125 S INTERLACHEN AVENUE #2
- $2.80M · 3 bd / 3.5 ba / 3,286 sq ft · 660 W MORSE BOULEVARD
- $1.40M · 3 bd / 2.5 ba / 2,585 sq ft · 512 W SWOOPE AVENUE (Vilasa Twnhms)
- $2.62M · 3 bd / 3.5 ba / 3,048 sq ft · 413 W MORSE BOULEVARD
Townhomes for sale in Winter Park by ZIP code
Where the inventory is: active listings and the median asking price by ZIP. ZIPs link to their housing scorecard.
Winter Park communities with the most townhomes for sale
The Winter Park neighborhoods and subdivisions with active listings, the median asking price in each, and what homes there actually sold for over the last 12 months. Community names open the community guide with live inventory, sales history, HOA and schools.
| Community | For sale | Median list | Median sold (12 mo) | Days on market |
|---|---|---|---|---|
| Swoope Park | 2 | $697,000 | — | — |
| The Enclave Winter Park | 2 | $1.50M | — | — |
| Townhomes/Harper Place | 2 | $557,500 | — | — |
| Urban Green 12 | 1 | $550,000 | — | — |
| Vilasa Twnhms | 1 | $1.40M | — | — |
| Virginia Heights | 1 | $999,000 | — | — |
| Virginia Hgts Rep | 1 | $810,000 | — | — |
The Winter Park housing market right now
Over the last 12 months 357 homes sold in Winter Park at a median of $447,000 (-3.3% year over year), $270 per square foot. Sellers received 95% of list price and homes took a median 32 days to go under contract. With 24 townhomes for sale against that sales pace, months of supply is 0.8, a seller’s market by the six-month rule. Cash buyers accounted for 41% of sales. New construction was 2% of sales.
Winter Park supply by price band
| Price band | Active | Sold, 12 mo | Months of supply | DOM |
|---|---|---|---|---|
| Under $300K | 23 | 76 | 3.6 | 55 |
| $300K–$500K | 20 | 55 | 4.4 | 26 |
| $500K–$750K | 22 | 97 | 2.7 | 30 |
| $750K+ | 27 | 129 | 2.5 | 38 |
Winter Park home prices by year
Median sold price, closed sales, days on market and sale-to-list ratio by year, from Momentum’s MLS record.
| Year | Median sold price | Homes sold | Days on market | Sale-to-list |
|---|---|---|---|---|
| 2019 | $473,163 | 64 | 100 | 93% |
| 2021 | $398,855 | 58 | 7 | 100% |
| 2022 | $475,714 | 1,277 | 9 | 99% |
| 2023 | $441,910 | 386 | 19 | 97% |
| 2024 | $616,104 | 929 | 19 | 96% |
| 2025 | $604,724 | 980 | 32 | 94% |
| 2026 | $596,865 | 845 | 32 | 95% |
What a home in Winter Park costs to own
Take the median $575,000 listing with 20% down at today’s 6.71% 30-year rate: principal and interest run about $2,971/month. Orange County’s typical millage of 16.67 puts property tax near $8,754/year after the $50,000 homestead exemption — and that is the reset bill a buyer pays, not the seller’s capped one. Citizens’ average premium in Orange County is about $1,409/year; newer roofs and inland addresses usually quote below it. All in, plan on roughly $3,818/month plus any HOA or CDD assessment.
Explore Winter Park
- All townhomes for sale in Orange County, FL
- Winter Park market intelligence: prices, supply and trends
- Moving to Winter Park: the data guide
- Cost of living in Winter Park
- New construction homes in Winter Park
- Best neighborhoods in Winter Park
- Orange County property tax guide
- Search every Winter Park community
- All Florida cities and counties
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Common questions
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Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Winter Park as of 2026-09-06 and refresh as homes list and sell. Listings courtesy of Stellar MLS as distributed by MLS GRID. The data relating to real estate for sale on this page comes in part from the Internet Data Exchange (IDX) program of the MLS(s) named above; listings held by brokerages other than Momentum Realty are marked with the listing brokerage’s name. Information is deemed reliable but not guaranteed. Estimates are not guarantees. Equal Housing Opportunity.