Winter Park Homes $500K and Up for Sale
Every home priced $500K and up currently for sale in Winter Park — pulled live from the Stellar MLS and updated continuously. Pair this with the free Winter Park market report to see what's actually selling, days on market, and sold-to-list ratios before you make an offer.
Live market brief ·
As of October 22, 2026, 187 homes $500K and up are listed for sale in Winter Park (ZIPs 32789 and 32792), from $500,000 to $6,995,000, with a median list price of about $1,300,000 (about $519 per square foot). That count includes 157 single-family homes, 18 townhomes or villas and 12 condominiums; single-family homes alone have a median list price of $1,370,000. Listings have been up a median of 70 days; 9 came on the market in the last 7 days; 83 (44%) have cut the asking price, by a median of 5.4%; 47 more are already under contract. Source: active listings on Stellar MLS via MLS GRID.
- for sale
- 187
- median list price
- $1,300,000
- median price / sq ft
- $519
- median days listed
- 70 days
- new in last 7 days
- 9
- price reductions
- 83 (44%)
- under contract
- 47
Active listings on Stellar MLS via MLS GRID in ZIPs 32789 and 32792, including condos and townhomes, updated automatically. List prices are asking prices, not sale prices.
Newest 24 of 187 Homes $500K and Up in the Winter Park area
$4,500,000
1631 Hillcrest Ave
Winter Park, FL 32789
5 bd · 6 ba · 4,754 sqft
Ellno Willo
MLS ID #O6443872, CHRIS QUARLES PROPERTIES LLC.
Listing provided by Stellar MLS
$699,900
1884 Jessica Ct
Winter Park, FL 32789
3 bd · 2 ba · 1,666 sqft
Waterbridge
MLS ID #O6450978, RE/MAX 200 REALTY.
Listing provided by Stellar MLS
$3,195,000
1825 Whitehall Dr
Winter Park, FL 32789
4 bd · 6 ba · 4,311 sqft
Kenilworth Shores Sec 06
MLS ID #O6450811, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$4,695,000
617 N Interlachen Ave
Winter Park, FL 32789
11 bd · 8 ba · 3,615 sqft
Winter Park
MLS ID #R4912183, EASY REALTY.
Listing provided by Stellar MLS
$3,495,000
1600 Legion Dr
Winter Park, FL 32789
5 bd · 6 ba · 4,483 sqft
Green Oaks Rep
MLS ID #O6450869, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$2,629,000
1681 Woodland Ave
Winter Park, FL 32789
5 bd · 5 ba · 3,682 sqft
Comstock Park
MLS ID #O6449440, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$695,000
2887 Temple Trl
Winter Park, FL 32789
2 bd · 3 ba · 1,801 sqft
Temple Trail Village
MLS ID #O6450536, ADAIR REALTY INC.
Listing provided by Stellar MLS
$6,000,000
1011 Mckean Cir
Winter Park, FL 32789
5 bd · 7 ba · 4,806 sqft
Palmer Park
MLS ID #O6449269, UNITED REAL ESTATE PREFERRED.
Listing provided by Stellar MLS
$750,000
8061 Pleasant Pine Cir
Winter Park, FL 32792
5 bd · 4 ba · 3,496 sqft
Enclave At Aloma
MLS ID #O6449669, RE/MAX ASSURED.
Listing provided by Stellar MLS
$3,390,000
1751 Glencoe Rd
Winter Park, FL 32789
5 bd · 7 ba · 4,520 sqft
Forest Hills
MLS ID #O6442410, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$1,249,000
1445 Via Sangro Pl
Winter Park, FL 32792
6 bd · 6 ba · 5,021 sqft
Lakeside Estates
MLS ID #O6449663, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$575,000
1399 Aloma Ave
Winter Park, FL 32789
3 bd · 2 ba · 1,804 sqft
Galloway Place Rep
MLS ID #O6449858, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$1,349,000
1939 Woodcrest Dr
Winter Park, FL 32792
4 bd · 4 ba · 2,575 sqft
MLS ID #O6449666, LA ROSA REALTY PREMIER LLC.
Listing provided by Stellar MLS
$950,000
1411 Devon Rd
Winter Park, FL 32789
2 bd · 2 ba · 1,947 sqft
Orwin Manor Westminster
MLS ID #O6449441, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$985,000
1611 Chestnut Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,916 sqft
Lake Knowles Terrace
MLS ID #O6449003, OLYMPUS EXECUTIVE REALTY INC.
Listing provided by Stellar MLS
$1,399,900
1737 Indiana Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,984 sqft
Lawndale
MLS ID #S5158760, LOKATION.
Listing provided by Stellar MLS
$519,900
731 Bongart Rd
Winter Park, FL 32792
4 bd · 3 ba · 1,842 sqft
Winter Park Estates
MLS ID #O6448911, BEYCOME OF FLORIDA LLC.
Listing provided by Stellar MLS
$575,000
2228 King Charles Ct
Winter Park, FL 32792
4 bd · 3 ba · 2,551 sqft
Winter Woods Unit 03
MLS ID #O6434929, KELLER WILLIAMS ADVANTAGE REALTY.
Listing provided by Stellar MLS
$649,000
518 Gilbert Rd
Winter Park, FL 32792
3 bd · 2 ba · 1,573 sqft
Winter Park Pines
MLS ID #O6442915, PALMANO GROUP RE BROKERAGE LLC.
Listing provided by Stellar MLS
$560,000
2067 Poinciana Rd
Winter Park, FL 32792
4 bd · 2 ba · 2,352 sqft
Winter Woods Unit 04
MLS ID #O6446898, WATSON REALTY CORP.
Listing provided by Stellar MLS
$1,699,900
2613 Lafayette Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,661 sqft
Charmont
MLS ID #O6447662, CORCORAN PREMIER REALTY.
Listing provided by Stellar MLS
$650,000
2322 Woodcrest Dr
Winter Park, FL 32792
4 bd · 2 ba · 1,650 sqft
Kenilworth Estates 1st Add
MLS ID #O6445796, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$2,125,000
918 Enclave Pl
Winter Park, FL 32792
5 bd · 5 ba · 3,713 sqft
The Enclave Winter Park
MLS ID #O6439116, CORCORAN PREMIER REALTY.
Listing provided by Stellar MLS
$900,000
2052 Wood Thrush Ln
Winter Park, FL 32792
4 bd · 3 ba · 2,807 sqft
Waters Edge At Hawks Crest
MLS ID #O6446652, KELLER WILLIAMS ADVANTAGE REALTY.
Listing provided by Stellar MLS
More Winter Park Homes for Sale
Winter Park buyer questions
How many homes $500K and up are for sale in Winter Park right now?+
As of October 22, 2026, 187 homes $500K and up are listed for sale in Winter Park (ZIPs 32789 and 32792), priced from $500,000 to $6,995,000; the middle half are listed between $740,000 and $2,195,000. That count includes 157 single-family homes, 18 townhomes or villas and 12 condominiums; single-family homes alone have a median list price of $1,370,000. This updates automatically from the Stellar MLS.
What is the median list price for homes $500K and up in Winter Park?+
The median list price is about $1,300,000, roughly $519 per square foot (active listings in Winter Park, October 22, 2026). List price is what sellers are asking, not what homes sell for; Ryan can walk you through what comparable homes have actually closed for in a private consultation.
Are sellers cutting prices on homes $500K and up in Winter Park?+
83 (44%) of the active homes $500K and up in Winter Park are listed below their original asking price, by a median of 5.4%, as of October 22, 2026. A price cut is a negotiating signal worth asking your agent about, along with how long the home has been listed.
How long have homes $500K and up in Winter Park been on the market?+
As of October 22, 2026, the homes $500K and up for sale in Winter Park have been listed a median of 70 days, and 9 came on the market in the last 7 days. This measures how long current listings have been up, not how long homes take to sell.
How many homes $500K and up in Winter Park are already under contract?+
47 homes $500K and up in Winter Park show as pending or under contract as of October 22, 2026, alongside 187 still active. A home can come back on the market if a contract falls through, so it is worth setting an alert.
How do mortgage rates affect what I can afford in Winter Park?+
Your monthly payment depends on the price, your down payment, your loan type and your rate, plus Florida taxes, insurance and any HOA dues. See this week's national rate averages and a payment calculator on the mortgage rates page, or ask Ryan, who is a licensed mortgage loan originator (NMLS #1784218, Mortgageinc NMLS #2028516) as well as the broker, for a personal quote. You are never required to use his lending services.
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of October 22, 2026 at 4:07 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA
Buying in Winter Park?
Tour with the broker. Ask about financing in the same conversation.
Ryan Solberg is the broker-owner of MaxLife Realty and a licensed mortgage loan originator (NMLS #1784218, Mortgageinc NMLS #2028516), so he can coordinate your home search and your financing. You are never required to use his lending services to work with him as your agent.
Freddie Mac U.S. weekly average, not a quote or an offer to lend.