Buying or selling? Call (904) 351-6461

Homes for Sale in Winter Park, FL

By , Co-Founder, Momentum Realty · Updated October 23, 2026

Buying in Winter Park? Get matched with a local agent →Selling? Get your Winter Park home value →or call (904) 351-6461

398 homes are for sale in Winter Park, FL as of 2026-10-23, with 23 more under contract. The median list price is $607,000 ($342/sq ft), most homes list between $210K to $2.62M, and the median listing has been on the market 56 days. That is 267 houses, 92 condos and 39 townhouses. 42 homes came on the market this week and 494 sold in the last 12 months at a median of $449,000.

Winter Park, FL key facts
LocationOrange County, FL
ZIP codes with their own page2
For sale right now398 active, 23 under contract
Asking prices$607,000 median · $342 per sq ft · most homes $210K–$2.62M
Median days on market (active listings)56
Property types for sale267 houses, 92 condos, 39 townhouses
New listings this week42
Homes sold, last 12 months494 at a median of $449,000

Listing counts and prices as of 2026-10-23; MLS data, refreshed nightly; sold figures are trailing 12 months of closed sales. Market figures describe homes, not residents. Cite as: Momentum Realty, “Winter Park, FL key facts,” movewithmomentum.com/homes-for-sale/winter-park-fl/, data as of 2026-10-23.

398
Homes for sale
$607,000
Median list price
$210K to $2.62M
Typical range
56
Median days on market
42
New this week
23
Under contract
$4,227
Est. monthly cost at median
9.7
Months of supply

Newest homes 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.

2812 MULFORD AVENUE, home for sale in Winter Park
$2.50M New
5 bd · 5.5 ba · 3,656 sq ft · built 2026
2812 MULFORD AVENUE, 32789
Winter Park
Listing courtesy of CORCORAN PREMIER REALTY
2887 TEMPLE TRAIL, home for sale in Winter Park
$695,000 New
2 bd · 2.5 ba · 1,801 sq ft · built 1984
2887 TEMPLE TRAIL, 32789
Winter Park
Listing courtesy of ADAIR REALTY INC
1458 LONE FEATHER TRAIL, home for sale in Winter Park
$650,000 New
4 bd · 2.5 ba · 1,770 sq ft · built 2022
1458 LONE FEATHER TRAIL, 32792
Winter Park
Listing courtesy of PREMIER SOTHEBY'S INTL. REALTY
2332 SHERBROOKE ROAD, home for sale in Winter Park
$549,000 New
4 bd · 3 ba · 1,842 sq ft · built 1967
2332 SHERBROOKE ROAD, 32792
Winter Park
Listing courtesy of KELLER WILLIAMS WINTER PARK
239 ORANGE TERRACE DRIVE, home for sale in Winter Park
$450,000 New
4 bd · 2.5 ba · 1,866 sq ft · built 1954
239 ORANGE TERRACE DRIVE, 32789
Winter Park
Listing courtesy of CREEGAN GROUP
2370 BARBADOS DRIVE, home for sale in Winter Park
$305,000 New
3 bd · 2 ba · 1,467 sq ft · built 1979
2370 BARBADOS DRIVE, 32792
Winter Park
Listing courtesy of COLDWELL BANKER REALTY
4786 TANGERINE AVENUE #4786, home for sale in Winter Park
$220,000 New
2 bd · 1.5 ba · 1,281 sq ft · built 1973
4786 TANGERINE AVENUE #4786, 32792
Wrenwood Condominium
Listing courtesy of EXP REALTY LLC
617 N INTERLACHEN AVENUE, home for sale in Winter Park
$4.70M New
11 bd · 7.5 ba · 3,615 sq ft · built 1929
617 N INTERLACHEN AVENUE, 32789
Winter Park Villas
Listing courtesy of EASY REALTY
1600 LEGION DRIVE, home for sale in Winter Park
$3.50M New
5 bd · 5.5 ba · 4,483 sq ft · built 2008
1600 LEGION DRIVE, 32789
Green Oaks Rep
Listing courtesy of COLDWELL BANKER REALTY
1681 WOODLAND AVENUE, home for sale in Winter Park
$2.63M New
5 bd · 4.5 ba · 3,682 sq ft · built 2027
1681 WOODLAND AVENUE, 32789
Comstock Park
Listing courtesy of ONE LUXURY INTERNATIONAL LLC
775 MCINTYRE AVENUE #9, home for sale in Winter Park
$849,999 New
3 bd · 2.5 ba · 2,052 sq ft · built 1987
775 MCINTYRE AVENUE #9, 32789
Winter Park
Listing courtesy of PARKSIDE PROPERTIES, LLC
7536 VILLAGE GREEN DRIVE, home for sale in Winter Park
$479,900 New
3 bd · 2 ba · 1,647 sq ft · built 1972
7536 VILLAGE GREEN DRIVE, 32792
Winter Park
Listing courtesy of RE/MAX TOWN & COUNTRY REALTY
5468 BRACKEN COURT, home for sale in Winter Park
$309,000 New
3 bd · 2.5 ba · 1,602 sq ft · built 1984
5468 BRACKEN COURT, 32792
Winter Park
Listing courtesy of EXP REALTY LLC
2873 OLD CASTLE DRIVE, home for sale in Winter Park
$1.40M New
4 bd · 4 ba · 4,247 sq ft · built 1993
2873 OLD CASTLE DRIVE, 32792
Winter Park
Listing courtesy of FANNIE HILLMAN & ASSOCIATES
1939 WOODCREST DRIVE, home for sale in Winter Park
$1.35M New
4 bd · 3.5 ba · 2,575 sq ft · built 2020
1939 WOODCREST DRIVE, 32792
Winter Park
Listing courtesy of LA ROSA REALTY PREMIER LLC
8061 PLEASANT PINE CIRCLE, home for sale in Winter Park
$750,000 New
5 bd · 3.5 ba · 3,496 sq ft · built 2013
8061 PLEASANT PINE CIRCLE, 32792
Enclave At Aloma
Listing courtesy of RE/MAX ASSURED
8113 LAZY BEAR LANE, home for sale in Winter Park
$585,000 New
4 bd · 2.5 ba · 2,267 sq ft · built 2015
8113 LAZY BEAR LANE, 32792
Winter Park
Listing courtesy of WATSON REALTY CORP
1818 DOVER ROAD, home for sale in Winter Park
$439,900 New
3 bd · 2 ba · 1,873 sq ft · built 1956
1818 DOVER ROAD, 32792
Winter Park
Listing courtesy of REAL ESTATE FIRM OF ORLANDO
2640 BEVERLY AVENUE, home for sale in Winter Park
$305,000 New
3 bd · 1 ba · 1,216 sq ft · built 1949
2640 BEVERLY AVENUE, 32789
Killarney Circle
Listing courtesy of REAL BROKER, LLC
1011 MCKEAN CIRCLE, home for sale in Winter Park
$6.00M New
5 bd · 6 ba · 4,806 sq ft · built 2027
1011 MCKEAN CIRCLE, 32789
Palmer Park
Listing courtesy of UNITED REAL ESTATE PREFERRED
1445 VIA SANGRO PLACE, home for sale in Winter Park
$1.25M New
6 bd · 5.5 ba · 5,021 sq ft · built 2015
1445 VIA SANGRO PLACE, 32792
Winter Park
Listing courtesy of COLDWELL BANKER REALTY
4599 WHIMBREL PLACE, home for sale in Winter Park
$675,000 New
4 bd · 3 ba · 2,366 sq ft · built 1994
4599 WHIMBREL PLACE, 32792
Winter Park
Listing courtesy of RE/MAX TOWN & COUNTRY REALTY
3409 FERNDELL DRIVE, home for sale in Winter Park
$415,900 New
3 bd · 2 ba · 1,412 sq ft · built 1967
3409 FERNDELL DRIVE, 32792
Winter Park
Listing courtesy of LPT REALTY, LLC
1740 PURITAN AVENUE, home for sale in Winter Park
$329,000 New
3 bd · 2 ba · 1,229 sq ft · built 1963
1740 PURITAN AVENUE, 32792
Eastbrook Sub Unit 06 2Nd Rep
Listing courtesy of KELLER WILLIAMS REALTY SMART 1

Winter Park homes for sale by price

Every active listing in Winter Park grouped by price, with the newest listings in each band. The median is $607,000; the busiest band is $1M and up.

Under $200K: 37 homes

$200K – $300K: 40 homes

$300K – $400K: 42 homes

$400K – $500K: 51 homes

$500K – $750K: 66 homes

$750K – $1M: 38 homes

$1M and up: 124 homes

Every home for sale in Winter Park right now (398)

All 398 active Winter Park listings with a detail page, newest first, refreshed twice a day from the MLS.

Showing the newest 150 of 398; the price bands above and the map cover the rest.

Homes 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.

ZIPHomes for saleMedian list price
32789203$1.15M
32792194$426,000
341121$259,900

Winter Park communities with the most homes 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.

CommunityFor saleMedian listMedian sold (12 mo)Days on market
Kenilworth Shores8$1.60M——
The Enclave Winter Park6$2.10M——
Winter Park Pines6$709,950——
Winter Park Villas5$1.50M——
Orwin Manor Westminster5$524,900——
Winter Park Estates5$519,900——
Golfside Villas Condo5$138,000——
Killarney Estates5$1.25M——
Stratford A Winter Park Condo4$168,450——
Charmont4$1.89M——
Maitland Shores First Add3$5.50M——
Mead Garden3$245,000——
Phillips Circle Rep3$925,000——
Seville Park3$575,000——
Sylvan Heights3$1.75M——
Comstock Park3$2.63M——
Lazy Oaks Condo3$274,900——
Park West Condo3$650,000——
Virginia Heights3$925,000——
Colonies3$140,000——
Eastbrook Sub Unit 06 2Nd Rep3$379,000——
Forest Hills3$3.39M——
J Kronenberger Sub3$5.20M——
Lake Killarney Condo3$285,000——
Lake Knowles Terrace Add 023$2.55M——
Lakeside Manor Apts Condo3$184,400——
Lawndale3$1.40M——
Palmer Ave Lakeside Prop2$4.88M——
Park Grove2$3.92M——
Parkview Village2$142,500——

What is for sale in Winter Park: property types

Another 3 listings in Winter Park are land, commercial or other non-residential property and are not counted above.

Browse by type: Condos for sale in Winter Park (92) · Townhomes for sale in Winter Park (39).

The Winter Park real estate market right now

Over the last 12 months 494 homes sold in Winter Park at a median of $449,000 (+1.6% year over year), $270 per square foot. Sellers received 96% of list price and homes took a median 33 days to go under contract. With 398 homes for sale against that sales pace, months of supply is 9.7, a buyer’s market by the six-month rule. Cash buyers accounted for 31% of sales. New construction was 3% of sales.

Winter Park supply by price band

Price bandActiveSold, 12 moMonths of supplyDOM
Under $300K381313.568
$300K–$500K15862.123
$500K–$750K21972.625
$750K+541803.646

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.

YearMedian sold priceHomes soldDays on marketSale-to-list
2019$457,423639892%
2021$490,389193799%
2022$462,5431,182999%
2023$497,7613682096%
2024$607,8629282196%
2025$619,7229593394%
2026$647,8258503496%

What a home in Winter Park costs to own

Take the median $607,000 listing with 20% down at today’s 7.32% 30-year rate: principal and interest run about $3,336/month. Orange County’s typical millage of 16.67 puts property tax near $9,287/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 $4,227/month plus any HOA or CDD assessment.

Communities buyers are searching in Winter Park. The Winter Park community pages people are opening from Google right now: Park Hill.

Explore Winter Park

Homes for sale near Winter Park

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.

Neighborhoods buyers are searching for in Winter Park

Winter Park guides & data

Everything we publish about Winter Park: live listings by type, prices and market data, taxes, insurance and what it costs to live here.

Common questions

How many homes are for sale in Winter Park, FL?
As of 2026-10-23, Momentum's MLS record shows 398 residential homes actively listed for sale in Winter Park and 23 under contract. 42 of them came on the market in the last 7 days.
What is the median home price in Winter Park?
The median list price of homes for sale in Winter Park is $607,000, about $342 per square foot for a typical 1,848-square-foot home. Ten percent of listings are under $210K and ten percent are above $2.62M. Over the last 12 months the median SOLD price was $449,000, +1.6% year over year.
How long do homes take to sell in Winter Park?
Homes currently listed have been on the market a median of 56 days. Homes that sold in the last 12 months took a median of 33 days and sold at 96% of list price. At today's inventory that is 9.7 months of supply, a buyer's market by the usual six-month rule.
What does a $607,000 home in Winter Park cost per month?
Roughly $4,227 a month with 20% down at 7.32%: principal and interest of $3,336, Orange County property tax of about $774/month after the $50,000 homestead exemption, and insurance near $117/month at the Citizens county average. HOA or CDD fees, where they apply, come on top.
Which Winter Park neighborhoods have the most homes for sale?
The communities with the most active listings right now are Kenilworth Shores (8), The Enclave Winter Park (6), Winter Park Pines (6), Winter Park Villas (5), Orwin Manor Westminster (5). Each community page carries its own sales history, live inventory and schools.
How do I see a home for sale in Winter Park?
Every listing on this page opens a full page with all photos, the community's data and a tour request. A Momentum agent who works Winter Park can show any home here, whether it is our listing or another brokerage's, at no cost to a buyer. Call (904) 351-6461 or use the form below.
Where is Winter Park, FL, and what county is it in?
Winter Park is in Orange County, Florida. Homes for sale there today carry the ZIP codes 32789, 32792, 34112. Nearby cities in the same county with homes for sale: Orlando, Winter Garden, Apopka, Windermere, Ocoee.
What ZIP codes are in Winter Park, FL?
Listings in Winter Park are currently in 3 ZIP codes: 32789, 32792, 34112. The ZIP table above shows how many homes are for sale in each and the median asking price.
How many houses are for sale in Winter Park, FL?
267 single-family houses are for sale in Winter Park today, out of 398 total listings (92 condos, 39 townhouses). The property-type section above breaks the inventory down, and each card opens the full listing.
How do I buy a house in Winter Park, FL?
Start with the numbers: 398 homes are for sale in Winter Park today at a median asking price of $607,000, so a 20% down payment on the median home is about $121,400 and principal and interest run near $3,336/month at today's 7.32% 30-year rate. Get pre-approved first, sign a written buyer agreement with your agent (required before touring since August 2024), then search by price band, ZIP or community above. Our Florida buyer closing-cost calculator itemizes the cash to close, and the Florida first-time buyer guide covers programs and down-payment help.
What county is Winter Park in?
Winter Park is in Orange County, Florida; a smaller share of Winter Park addresses fall in Seminole County. Orange County's 12-month median sale price is $462K on 14,110 closings. Property tax, school zoning and permitting for Winter Park run through Orange County.
Is Winter Park a good place to live?
That depends on your budget, commute and the kind of home you want, so here is what the housing data says about Winter Park: the median sale price over the last 12 months was $449K across 494 closings (+1.6% year over year), about the same as the Orange County median of $462K; homes took a median 33 days to go under contract; 327 homes are for sale today, 4.5 months of supply at the current pace, which is balanced; the communities with the most sales are Kenilworth Shores Sec 1, Eastbrook Sub Unit 8, EASTBROOK SUB UNIT 05, KENILWORTH SHORES SEC 06. The market tracker, price bands and community pages on this site carry the full numbers.
Is Winter Park in a flood zone?
Mostly no. Across 48 homes sampled in Winter Park's largest communities, nearly all sit outside a FEMA Special Flood Hazard Area (Zone X). Flood zones are drawn parcel by parcel, so check the exact address on FEMA's flood map; each community page here shows its own mix.

Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Winter Park as of 2026-10-23 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.

More communities in Winter Park

Maccallum

Free monthly report

Get the Central Florida Market Pulse every month

One email when the new edition is out: median price and the same-home change, days on market, months of supply, price cuts and what failed to sell, computed from MLS closed records. See the current edition. Unsubscribe any time.

By subscribing, you agree that EAB RE INVESTMENTS LLC (Momentum Realty) and its agents may email you about the report and the local market. You do not need to consent as a condition of buying any property, goods, or services. See our Privacy Policy.

Buying in Winter Park?

See any home on this page with a local agent.

A Momentum agent who works Winter Park every week will set up showings, pull the comps before you offer, and tell you which of these homes is actually priced right. No cost to a buyer.

Selling instead? See what your home would list for.

Tour homes in Winter Park

Tell us what you are looking for and a local agent will reach out, usually within one business day.

or call (904) 351-6461