Townhomes for Sale in Winter Park, FL
41 townhomes are for sale in Winter Park, FL as of 2026-11-06. The median list price is $440,000 ($221/sq ft), most townhomes list between $285K to $2.62M, and the median listing has been on the market 63 days. 6 townhomes came on the market this week and 887 sold in the last 12 months at a median of $499,000.
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 $440,000; the busiest band is $300K – $400K.
Under $200K: 1 home
$200K – $300K: 5 homes
- $220,000 · 2 bd / 1.5 ba / 1,281 sq ft · 4786 TANGERINE AVENUE #4786 (Wrenwood Condominium)
- $299,000 · 3 bd / 2.5 ba / 1,602 sq ft · 5468 BRACKEN COURT
- $285,000 · 3 bd / 2 ba / 1,467 sq ft · 2657 EXUMA WAY
- $275,000 · 2 bd / 2 ba / 1,544 sq ft · 2302 BARBADOS DRIVE
$300K – $400K: 13 homes
- $305,000 · 3 bd / 2 ba / 1,467 sq ft · 2370 BARBADOS DRIVE
- $325,000 · 3 bd / 2 ba / 1,783 sq ft · 2535 LEEWARD WAY
- $325,000 · 3 bd / 2.5 ba / 1,628 sq ft · 1462 SICILIANO POINT
- $325,000 · 3 bd / 2.5 ba / 1,866 sq ft · 7560 ALOMA PINES COURT
$400K – $500K: 4 homes
- $440,000 · 3 bd / 2.5 ba / 2,308 sq ft · 1552 LITTLE WREN LANE
- $460,000 · 3 bd / 2.5 ba / 2,076 sq ft · 2356 SHADOWLAND LOOP
- $482,000 · 3 bd / 2.5 ba / 2,308 sq ft · 1407 BROAD WING LANE
- $425,000 · 3 bd / 2.5 ba / 1,755 sq ft · 2349 SHADOWLAND LOOP
$500K – $750K: 7 homes
- $650,000 · 3 bd / 2.5 ba / 1,798 sq ft · 1261 MICHIGAN AVENUE (Park Shore)
- $695,000 · 2 bd / 2.5 ba / 1,801 sq ft · 2887 TEMPLE TRAIL
- $575,000 · 2 bd / 2.5 ba / 1,648 sq ft · 1259 INDIANA AVENUE (Townhomes/Harper Place)
- $660,000 · 3 bd / 3 ba / 1,690 sq ft · 1256 MELISSA COURT
$750K – $1M: 3 homes
- $915,000 · 3 bd / 3.5 ba / 2,093 sq ft · 1927 S LAKEMONT AVENUE (Lake Spier Xing)
- $925,000 · 3 bd / 3 ba / 2,434 sq ft · 1138 S PENNSYLVANIA AVENUE
- $774,900 · 3 bd / 3.5 ba / 2,030 sq ft · 1265 ARLINGTON PL (Virginia Hgts Rep)
$1M and up: 8 homes
- $4.00M · 3 bd / 4 ba / 3,885 sq ft · 125 S INTERLACHEN AVENUE #4
- $3.65M · 3 bd / 4 ba / 3,878 sq ft · 125 S INTERLACHEN AVENUE #1
- $3.00M · 3 bd / 4 ba / 3,244 sq ft · 125 S INTERLACHEN AVENUE #2
- $2.69M · 3 bd / 3.5 ba / 3,286 sq ft · 660 W MORSE BOULEVARD
Every home for sale in Winter Park right now (41)
All 41 active Winter Park listings with a detail page, newest first, refreshed twice a day from the MLS.
- $305,000 · 3 bd / 2 ba / 1,467 sq ft · 2370 BARBADOS DRIVE
- $650,000 · 3 bd / 2.5 ba / 1,798 sq ft · 1261 MICHIGAN AVENUE (Park Shore)
- $325,000 · 3 bd / 2 ba / 1,783 sq ft · 2535 LEEWARD WAY
- $440,000 · 3 bd / 2.5 ba / 2,308 sq ft · 1552 LITTLE WREN LANE
- $4.00M · 3 bd / 4 ba / 3,885 sq ft · 125 S INTERLACHEN AVENUE #4
- $460,000 · 3 bd / 2.5 ba / 2,076 sq ft · 2356 SHADOWLAND LOOP
- $325,000 · 3 bd / 2.5 ba / 1,628 sq ft · 1462 SICILIANO POINT
- $220,000 · 2 bd / 1.5 ba / 1,281 sq ft · 4786 TANGERINE AVENUE #4786 (Wrenwood Condominium)
- $695,000 · 2 bd / 2.5 ba / 1,801 sq ft · 2887 TEMPLE TRAIL
- $299,000 · 3 bd / 2.5 ba / 1,602 sq ft · 5468 BRACKEN COURT
- $482,000 · 3 bd / 2.5 ba / 2,308 sq ft · 1407 BROAD WING LANE
- $169,000 · 2 bd / 2.5 ba / 1,031 sq ft · 3307 AMBER WOOD WAY #106
- $325,000 · 3 bd / 2.5 ba / 1,866 sq ft · 7560 ALOMA PINES COURT
- $285,000 · 3 bd / 2 ba / 1,467 sq ft · 2657 EXUMA WAY
- $355,000 · 3 bd / 2.5 ba / 1,872 sq ft · 7498 ALOMA PINES COURT
- $275,000 · 2 bd / 2 ba / 1,544 sq ft · 2302 BARBADOS DRIVE
- $425,000 · 3 bd / 2.5 ba / 1,755 sq ft · 2349 SHADOWLAND LOOP
- $915,000 · 3 bd / 3.5 ba / 2,093 sq ft · 1927 S LAKEMONT AVENUE (Lake Spier Xing)
- $365,000 · 3 bd / 2.5 ba / 1,861 sq ft · 7506 CRANES CREEK COURT #30
- $279,999 · 3 bd / 2 ba / 1,467 sq ft · 2275 ISLAND RUN
- $306,900 · 3 bd / 2.5 ba / 1,545 sq ft · 7530 CRANES CREEK COURT
- $575,000 · 2 bd / 2.5 ba / 1,648 sq ft · 1259 INDIANA AVENUE (Townhomes/Harper Place)
- $660,000 · 3 bd / 3 ba / 1,690 sq ft · 1256 MELISSA COURT
- $349,000 · 3 bd / 2.5 ba / 1,872 sq ft · 7605 ALOMA PINES COURT
- $394,500 · 3 bd / 2.5 ba / 1,782 sq ft · 2857 CLEVER LANE
- $379,998 · 3 bd / 2.5 ba / 1,907 sq ft · 2017 CANNY COVE
- $575,000 · 2 bd / 2.5 ba / 1,851 sq ft · 1071 ARAGON AVENUE (Seville Park)
- $3.65M · 3 bd / 4 ba / 3,878 sq ft · 125 S INTERLACHEN AVENUE #1
- $3.00M · 3 bd / 4 ba / 3,244 sq ft · 125 S INTERLACHEN AVENUE #2
- $389,000 · 3 bd / 2.5 ba / 1,907 sq ft · 2033 CANNY COVE
- $925,000 · 3 bd / 3 ba / 2,434 sq ft · 1138 S PENNSYLVANIA AVENUE
- $2.69M · 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)
- $774,900 · 3 bd / 3.5 ba / 2,030 sq ft · 1265 ARLINGTON PL (Virginia Hgts Rep)
- $2.62M · 3 bd / 3.5 ba / 3,048 sq ft · 413 W MORSE BOULEVARD
- $535,000 · 3 bd / 3.5 ba / 1,937 sq ft · 1250 FORMOSA AVENUE (Urban Green 12)
- $375,000 · 3 bd / 2.5 ba / 1,872 sq ft · 7522 ALOMA PINES COURT
- $399,000 · 3 bd / 2.5 ba / 1,907 sq ft · 1995 CANNY COVE
- $1.55M · 4 bd / 3.5 ba / 2,756 sq ft · 905 ENCLAVE PLACE (The Enclave Winter Park)
- $1.55M · 4 bd / 3.5 ba / 2,738 sq ft · 901 ENCLAVE PLACE (The Enclave Winter Park)
- $680,000 · 4 bd / 3.5 ba / 2,664 sq ft · 432 W SWOOPE AVENUE (Swoope Park)
Pending and under contract in Winter Park (1)
Winter Park homes that have an accepted offer and are working toward closing. They can still fall through, so each one keeps its page until it closes.
Browse every listing on Momentum Realty.
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 |
|---|---|---|---|---|
| The Enclave Winter Park | 2 | $1.55M | — | — |
| Lake Spier Xing | 1 | $915,000 | — | — |
| Seville Park | 1 | $575,000 | — | — |
| Townhomes/Harper Place | 1 | $575,000 | — | — |
| Urban Green 12 | 1 | $535,000 | — | — |
| Vilasa Twnhms | 1 | $1.40M | — | — |
| Virginia Hgts Rep | 1 | $774,900 | — | — |
| Wrenwood Condominium | 1 | $220,000 | — | — |
| Swoope Park | 1 | $680,000 | — | — |
| Park Shore | 1 | $650,000 | — | — |
The Winter Park real estate market right now
Over the last 12 months 887 homes sold in Winter Park at a median of $499,000 (-0.2% year over year), $270 per square foot. Sellers received 98% of list price and homes took a median 37 days to go under contract. With 41 townhomes for sale against that sales pace, months of supply is 0.6, a seller’s market by the six-month rule. Cash buyers accounted for 32% of sales. New construction was 6% of sales.
Winter Park supply by price band
| Price band | Active | Sold, 12 mo | Months of supply | DOM |
|---|---|---|---|---|
| Under $300K | 10 | 65 | 1.8 | 93 |
| $300K–$500K | 2 | 26 | 0.9 | 19 |
| $500K–$750K | 8 | 55 | 1.7 | 15 |
| $750K+ | 22 | 74 | 3.6 | 40 |
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 |
|---|---|---|---|---|
| 2018 | $256,629 | 67 | 29 | 97% |
| 2021 | $361,230 | 13 | 8 | 100% |
| 2022 | $406,045 | 278 | 7 | 100% |
| 2023 | $492,843 | 64 | 27 | 96% |
| 2024 | $558,975 | 177 | 18 | 97% |
| 2025 | $454,585 | 214 | 24 | 95% |
| 2026 | $608,096 | 312 | 38 | 96% |
What a home in Winter Park costs to own
Take the median $440,000 listing with 20% down at today’s 7.18% 30-year rate: principal and interest run about $2,385/month. Orange County’s typical millage of 16.67 puts property tax near $6,503/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 $3,044/month plus any HOA or CDD assessment.
Explore Winter Park
- All townhomes for sale in Orange County, FL
- What is my house worth in Winter Park? Home values, $/sq ft and days to contract
- 4-bedroom townhomes for sale in Winter Park
- Homes under $300K in Winter Park
- Homes from $300K to $500K in Winter Park
- Winter Park pool townhomes for sale
- Winter Park waterfront townhomes for sale
- Gated communities in Winter Park
- Luxury townhomes for sale in Winter Park
- New listings this week in Winter Park
- Price reductions this week in Winter Park
- Winter Park homes by street
- What $500K buys in Orange County
- Winter Park market intelligence: prices, supply and trends
- Winter Park ZIP codes: every ZIP, map and home prices
- 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
- Orange County down payment assistance limits
- First-time home buyer guide for Florida
- Search every Winter Park community
- Best places to live in Florida: every city ranked by the numbers
- All Florida cities and counties
Townhomes for sale near Winter Park
- Townhomes for sale in Orlando, FL — 4361 listings
- Townhomes for sale in Winter Garden, FL — 723 listings
- Townhomes for sale in Apopka, FL — 547 listings
- Townhomes for sale in Windermere, FL — 269 listings
- Townhomes for sale in Ocoee, FL — 153 listings
- Townhomes for sale in Maitland, FL — 124 listings
- Townhomes for sale in Zellwood, FL — 56 listings
- Townhomes for sale in Oakland, FL — 35 listings
- Townhomes for sale in Belle Isle, FL — 32 listings
- Townhomes for sale in Gotha, FL — 19 listings
- Townhomes for sale in Christmas, FL — 8 listings
- Townhomes for sale in Golden Oak, FL — 6 listings
Recently off market in Winter Park
Homes in Winter Park that left the market most recently, with their last list price and a public-record page for each address. Off-market pages keep the community, tax and sales-history context after a listing closes or expires.
- 269 E Canton Avenue #269 · last listed $899,000 · off market Nov 6, 2026
- 2157 Lake Drive · last listed $689,000 · off market Nov 6, 2026
- 1320 Buckingham Road · last listed $449,000 · off market Nov 6, 2026
- 7302 Swallow Run #7302 · last listed $134,900 · off market Nov 3, 2026
- 2054 Eastbrook Boulevard · last listed $500,000 · off market Nov 3, 2026
- 1592 Arbor Park Drive · last listed $700,000 · off market Nov 3, 2026
- 274 N Ranger Boulevard · last listed $629,900 · off market Nov 2, 2026
- 2372 Sun Valley Circle #2372 · last listed $285,000 · off market Nov 2, 2026
- 7327 Forest Hill Court #223 · last listed $175,000 · off market Nov 1, 2026
- 525 S Lakemont Avenue · last listed $1,999,990 · off market Nov 1, 2026
- 525 Ololu Drive · last listed $490,900 · off market Nov 1, 2026
- 2948 Antique Oaks Circle #94 · last listed $150,000 · off market Nov 1, 2026
Common questions
How many townhomes are for sale in Winter Park, FL?
What is the median home price in Winter Park?
How long do homes take to sell in Winter Park?
What does a $440,000 home in Winter Park cost per month?
Which Winter Park neighborhoods have the most townhomes for sale?
How do I see a home for sale in Winter Park?
Where is Winter Park, FL, and what county is it in?
What ZIP codes are in Winter Park, FL?
How do I buy a house in Winter Park, FL?
Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Winter Park as of 2026-11-06 and refresh as homes list and sell. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. 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.