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Homes for Sale in Winter Park, FL

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390 homes are for sale in Winter Park, FL as of 2026-10-26, with 17 more under contract. The median list price is $614,250 ($341/sq ft), most homes list between $205K to $2.70M, and the median listing has been on the market 60 days. That is 261 houses, 91 condos and 38 townhouses. 34 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 now390 active, 17 under contract
Asking prices$614,250 median · $341 per sq ft · most homes $205K–$2.70M
Median days on market (active listings)60
Property types for sale261 houses, 91 condos, 38 townhouses
New listings this week34
Homes sold, last 12 months494 at a median of $449,000

Listing counts and prices as of 2026-10-26; 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 2026-10-26.

390
Homes for sale
$614,250
Median list price
$205K to $2.70M
Typical range
60
Median days on market
34
New this week
17
Under contract
$4,277
Est. monthly cost at median
9.5
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
Eastbrook Sub
photos on the listing
$419,900 New
4 bd · 2 ba · 1,427 sq ft · built 1960
603 CARNATION DRIVE, 32792
Eastbrook Sub
Listing courtesy of A-WARD WINNING REALTY LLC
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
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
Eastgate Sub Winter Park
photos on the listing
$450,000 New
3 bd · 2 ba · 1,346 sq ft · built 1958
506 LANDER ROAD, 32792
Eastgate Sub Winter Park
Listing courtesy of DERENTHAL REALTY
Winter Park
photos on the listing
$2.19M New
5 bd · 4.5 ba · 4,213 sq ft · built 1999
304 SANTIAGO DRIVE, 32789
Winter Park
Listing courtesy of FANNIE HILLMAN & ASSOCIATES
Glencoe Sub Winter Park
photos on the listing
$985,000 New
5 bd · 3 ba · 3,296 sq ft · built 1928
2330 WESTMINSTER CT., 32789
Glencoe Sub Winter Park
Listing courtesy of FANNIE HILLMAN & ASSOCIATES
Kenilworth Shores
photos on the listing
$620,000 New
3 bd · 2 ba · 1,762 sq ft · built 1963
624 DUNRAVEN DRIVE, 32792
Kenilworth Shores
Listing courtesy of KELLER WILLIAMS WINTER PARK
Ellno Willo
photos on the listing
$4.50M New
5 bd · 5.5 ba · 4,754 sq ft · built 2023
1631 HILLCREST AVENUE, 32789
Ellno Willo
Listing courtesy of CHRIS QUARLES PROPERTIES LLC
Waterbridge
photos on the listing
$699,900 New
3 bd · 2 ba · 1,666 sq ft · built 1985
1884 JESSICA COURT, 32789
Waterbridge
Listing courtesy of RE/MAX 200 REALTY
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
2174 SHADYHILL TERRACE, home for sale in Winter Park
$529,900 New
4 bd · 2 ba · 1,983 sq ft · built 1987
2174 SHADYHILL TERRACE, 32792
Winter Park
Listing courtesy of SET HOMES REALTY LLC
Winter Park Estates
photos on the listing
$509,999 New
3 bd · 2 ba · 1,460 sq ft · built 1960
808 DENSMORE DRIVE, 32792
Winter Park Estates
Listing courtesy of NOVA REAL ESTATE SERVICES INC
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
Kenilworth Shores
photos on the listing
$3.19M New
4 bd · 5 ba · 4,311 sq ft · built 2026
1825 WHITEHALL DRIVE, 32789
Kenilworth Shores
Listing courtesy of COMPASS FLORIDA LLC
Wrenwood Condominium
photos on the listing
$188,800 New
2 bd · 2 ba · 1,058 sq ft · built 1973
4832 TANGERINE AVENUE #4832, 32792
Wrenwood Condominium
Listing courtesy of STARHOMES REALTY LLC
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
2825 MULFORD AVENUE, home for sale in Winter Park
$629,000 New
2 bd · 2 ba · 1,249 sq ft · built 1952
2825 MULFORD AVENUE, 32789
Winter Park
Listing courtesy of RE/MAX TOWN & COUNTRY REALTY
1409 ASTER COURT, home for sale in Winter Park
$589,900 New
4 bd · 2 ba · 2,050 sq ft · built 1983
1409 ASTER COURT, 32792
Winter Park
Listing courtesy of RE/MAX SELECT GROUP
510 FITZWALTER DRIVE, home for sale in Winter Park
$530,000 New
3 bd · 2 ba · 1,385 sq ft · built 1960
510 FITZWALTER DRIVE, 32792
Winter Park
Listing courtesy of FANNIE HILLMAN & ASSOCIATES
2356 SHADOWLAND LOOP, home for sale in Winter Park
$460,000 New
3 bd · 2.5 ba · 2,076 sq ft · built 2020
2356 SHADOWLAND LOOP, 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
3150 SHADY PINE AVENUE, home for sale in Winter Park
$439,900 New
4 bd · 2 ba · 1,624 sq ft · built 1983
3150 SHADY PINE AVENUE, 32792
Winter Park
Listing courtesy of WATSON REALTY CORP

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 $614,250; the busiest band is $1M and up.

Under $200K: 38 homes

$200K – $300K: 39 homes

$300K – $400K: 35 homes

$400K – $500K: 54 homes

$500K – $750K: 64 homes

$750K – $1M: 38 homes

$1M and up: 122 homes

Every home for sale in Winter Park right now (390)

All 390 active Winter Park listings with a detail page, newest first, refreshed twice a day from the MLS.

Pending and under contract in Winter Park (17)

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.

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
32789197$1.18M
32792192$429,950
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 Shores10$1.60M——
Winter Park Pines7$695,000——
The Enclave Winter Park6$2.10M——
Winter Park Estates6$514,950——
Winter Park Villas5$1.50M——
Killarney Estates5$1.18M——
Orwin Manor Westminster5$524,900——
Golfside Villas Condo5$138,000——
Charmont4$1.89M——
Stratford A Winter Park Condo4$168,450——
Eastbrook Sub Unit 06 2Nd Rep3$374,000——
Forest Hills3$3.39M——
J Kronenberger Sub3$5.20M——
Lake Knowles Terrace Add 023$2.55M——
Lawndale3$1.40M——
Park West Condo3$650,000——
Seville Park3$575,000——
Sylvan Heights3$1.75M——
Wrenwood Condominium3$188,800——
Colonies3$140,000——
Comstock Park3$2.63M——
Lake Killarney Condo3$285,000——
Lakeside Manor Apts Condo3$184,400——
Maitland Shores First Add3$5.50M——
Mead Garden3$245,000——
Phillips Circle Rep3$925,000——
Winter Park Gardens Condo2$352,000——
Winter Park Village2$1.27M——
Winter Park Woods Condo2$104,500——
Chateaux Du Lac2$245,000——

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 (91) · Townhomes for sale in Winter Park (38).

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 390 homes for sale against that sales pace, months of supply is 9.5, 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 $614,250 listing with 20% down at today’s 7.32% 30-year rate: principal and interest run about $3,376/month. Orange County’s typical millage of 16.67 puts property tax near $9,408/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 $4,277/month plus any HOA or CDD assessment.

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

Common questions

How many homes are for sale in Winter Park, FL?
As of 2026-10-26, Momentum's MLS record shows 390 residential homes actively listed for sale in Winter Park and 17 under contract. 34 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 $614,250, about $341 per square foot for a typical 1,856-square-foot home. Ten percent of listings are under $205K and ten percent are above $2.70M. 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 60 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 9.5 months of supply, a buyer's market by the usual six-month rule.
What does a $614,250 home in Winter Park cost per month?
Roughly $4,277 a month with 20% down at 7.32%: principal and interest of $3,376, Orange County property tax of about $784/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 (10), Winter Park Pines (7), The Enclave Winter Park (6), Winter Park Estates (6), Winter Park Villas (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?
261 single-family houses are for sale in Winter Park today, out of 390 total listings (91 condos, 38 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: 390 homes are for sale in Winter Park today at a median asking price of $614,250, so a 20% down payment on the median home is about $122,850 and principal and interest run near $3,376/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 2026-10-26 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.

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Just listed in Winter Park

New on the market in the last 48 hours, newest first. Updated every hour (as of 2026-10-27 23:38 UTC).

all new listings in this MLS

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