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 November 11, 2026, 183 homes $500K and up are listed for sale in Winter Park (ZIPs 32789 and 32792), from $509,999 to $6,900,000, with a median list price of about $1,370,000 (about $517 per square foot). That count includes 153 single-family homes, 18 townhomes or villas and 12 condominiums; single-family homes alone have a median list price of $1,400,000. Listings have been up a median of 73 days; 7 came on the market in the last 7 days; 80 (44%) have cut the asking price, by a median of 5.7%; 52 more are already under contract. Source: active listings on Stellar MLS via MLS GRID.
- for sale
- 183
- median list price
- $1,370,000
- median price / sq ft
- $517
- median days listed
- 73 days
- new in last 7 days
- 7
- price reductions
- 80 (44%)
- under contract
- 52
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 183 Homes $500K and Up in the Winter Park area
$2,100,000
Winter Park, FL 32789
4 bd · 5 ba · 2,830 sqft
Lake Killarney Shores
MLS ID #O6456614, PLATINUM REALTY GROUP FLORIDA INC.
Listing provided by Stellar MLS
$1,850,000
2507 Lafayette Ave
Winter Park, FL 32789
4 bd · 6 ba · 2,675 sqft
Winter Park Village
MLS ID #O6450302, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$1,100,000
531 Worthington Dr
Winter Park, FL 32789
3 bd · 3 ba · 2,626 sqft
Kenilworth Shores
MLS ID #O6455524, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$968,000
1400 Pelican Bay Trl
Winter Park, FL 32792
5 bd · 4 ba · 3,600 sqft
Pelican Bay
MLS ID #O6456240, ABSOLUTE REALTY GROUP, LLC.
Listing provided by Stellar MLS
$739,000
1140 Washington Ave #16c
Winter Park, FL 32789
3 bd · 3 ba · 2,069 sqft
Quarters At Winter Park Condo
MLS ID #O6456091, CHEVON EATON.
Listing provided by Stellar MLS
$2,750,000
1663 N Park Ave
Winter Park, FL 32789
4 bd · 5 ba · 3,640 sqft
Dixie Terrace
MLS ID #O6453687, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$1,149,000
1824 Jessica Ct
Winter Park, FL 32789
4 bd · 3 ba · 2,582 sqft
Waterbridge
MLS ID #O6452920, RE/MAX 200 REALTY.
Listing provided by Stellar MLS
$895,000
1118 Washington Ave #5c
Winter Park, FL 32789
3 bd · 3 ba · 2,170 sqft
Quarters At Winter Park Condo
MLS ID #O6455084, BEYCOME OF FLORIDA LLC.
Listing provided by Stellar MLS
$739,000
2315 Kestrel Perch Pl
Winter Park, FL 32792
4 bd · 4 ba · 2,553 sqft
Meadows At Hawks Crest
MLS ID #O6455230, U S GLORY REALTY.
Listing provided by Stellar MLS
$849,000
1507 Golfside Dr
Winter Park, FL 32792
3 bd · 2 ba · 2,003 sqft
Greenview At Winter Pines
MLS ID #S5160711, LPT REALTY, LLC.
Listing provided by Stellar MLS
$650,000
1261 Michigan Ave
Winter Park, FL 32789
3 bd · 3 ba · 1,798 sqft
Park Shore
MLS ID #O6450090, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$5,950,000
1441 Grove Ter
Winter Park, FL 32789
5 bd · 6 ba · 5,796 sqft
Sylvan Lake Shores
MLS ID #O6450422, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$3,995,000
125 S Interlachen Ave #4
Winter Park, FL 32789
3 bd · 5 ba · 3,885 sqft
South Interlachen Place
MLS ID #O6453558, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$2,449,000
1441 Palm Ave
Winter Park, FL 32789
5 bd · 5 ba · 3,391 sqft
Lake Knowles Terrace Add 02
MLS ID #O6452896, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$1,499,000
1350 Lyndale Blvd
Winter Park, FL 32789
4 bd · 4 ba · 3,478 sqft
Dixie Terrace
MLS ID #O6453655, PREMIER BROKERS INTERNATIONAL.
Listing provided by Stellar MLS
$1,425,000
2237 Woodcrest Dr
Winter Park, FL 32792
4 bd · 5 ba · 3,563 sqft
Kenilworth Estates
MLS ID #TB8563139, WEEKLEY HOMES REALTY COMPANY.
Listing provided by Stellar MLS
$1,379,900
1534 Miller Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,984 sqft
Lawndale
MLS ID #O6454003, RE/MAX EXCLUSIVE COLLECTION.
Listing provided by Stellar MLS
$1,175,000
1500 Harris Cir
Winter Park, FL 32789
3 bd · 3 ba · 2,096 sqft
Sylvan Lake Shores
MLS ID #O6453807, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$5,995,000
1200 Via Salerno
Winter Park, FL 32789
5 bd · 6 ba · 5,476 sqft
Cloister Grove Sub
MLS ID #O6447322, KELLY PRICE & COMPANY LLC.
Listing provided by Stellar MLS
$849,900
2011 Harmon Ave
Winter Park, FL 32789
4 bd · 3 ba · 2,434 sqft
Lawndale
MLS ID #O6453173, RE/MAX EXCLUSIVE COLLECTION.
Listing provided by Stellar MLS
$985,000
2330 Westminster Ct.
Winter Park, FL 32789
5 bd · 3 ba · 3,296 sqft
Glencoe Sub
MLS ID #O6452380, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$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
$509,999
808 Densmore Dr
Winter Park, FL 32792
3 bd · 2 ba · 1,460 sqft
Winter Park Estates
MLS ID #O6451977, NOVA REAL ESTATE SERVICES INC.
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 November 11, 2026, 183 homes $500K and up are listed for sale in Winter Park (ZIPs 32789 and 32792), priced from $509,999 to $6,900,000; the middle half are listed between $795,000 and $2,350,000. That count includes 153 single-family homes, 18 townhomes or villas and 12 condominiums; single-family homes alone have a median list price of $1,400,000. 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 $1,370,000, roughly $517 per square foot (active listings in Winter Park, November 11, 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?+
80 (44%) of the active homes $500K and up in Winter Park are listed below their original asking price, by a median of 5.7%, as of November 11, 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 November 11, 2026, the homes $500K and up for sale in Winter Park have been listed a median of 73 days, and 7 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?+
52 homes $500K and up in Winter Park show as pending or under contract as of November 11, 2026, alongside 183 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 November 11, 2026 at 6:40 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.