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 2, 2026, 195 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 $528 per square foot). That count includes 165 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 65 days; 7 came on the market in the last 7 days; 83 (43%) have cut the asking price, by a median of 6%; 55 more are already under contract. Source: active listings on Stellar MLS via MLS GRID.
- for sale
- 195
- median list price
- $1,300,000
- median price / sq ft
- $528
- median days listed
- 65 days
- new in last 7 days
- 7
- price reductions
- 83 (43%)
- under contract
- 55
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 195 Homes $500K and Up in Winter Park
$850,000
100 S Interlachen Ave #401
Winter Park, FL 32789
3 bd · 2 ba · 1,639 sqft
Cloisters Condo
MLS ID #O6443942, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$589,900
1409 Aster Ct
Winter Park, FL 32792
4 bd · 2 ba · 2,050 sqft
Garden Lake Estates
MLS ID #S5158750, RE/MAX SELECT GROUP.
Listing provided by Stellar MLS
$1,995,000
2007 Edwin Blvd
Winter Park, FL 32792
4 bd · 4 ba · 3,314 sqft
Eastgate Sub
MLS ID #O6439783, DREAM FINDERS REALTY GROUP CORP.
Listing provided by Stellar MLS
$1,950,000
513 Dunraven Dr
Winter Park, FL 32792
5 bd · 5 ba · 3,560 sqft
Kenilworth Shores Sec 03
MLS ID #O6444889, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$850,000
870 N Phelps Ave
Winter Park, FL 32789
4 bd · 3 ba · 2,301 sqft
Osceola Or Lakeview Deed
MLS ID #O6445731, RE/MAX TOWN & COUNTRY REALTY.
Listing provided by Stellar MLS
$724,900
266 N Ranger Blvd
Winter Park, FL 32792
4 bd · 3 ba · 1,692 sqft
Winter Park Pines
MLS ID #O6444727, ELITE PROPERTY REAL ESTATE LLC.
Listing provided by Stellar MLS
$769,900
1003 Golfside Dr
Winter Park, FL 32792
3 bd · 3 ba · 2,145 sqft
Golfside Sec 02
MLS ID #O6444366, QP HOMES REALTY LLC.
Listing provided by Stellar MLS
$780,000
739 Roughbeard Rd
Winter Park, FL 32792
5 bd · 3 ba · 2,194 sqft
Winter Park Pines
MLS ID #O6444000, SERHANT.
Listing provided by Stellar MLS
$2,990,000
532 Langholm Dr
Winter Park, FL 32789
5 bd · 5 ba · 4,050 sqft
Kenilworth Shores Sec 01
MLS ID #O6442823, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$2,089,000
1951 Winter Park Rd
Winter Park, FL 32789
4 bd · 4 ba · 3,479 sqft
Charmont
MLS ID #O6441816, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$1,890,000
2614 Parkland Dr
Winter Park, FL 32789
4 bd · 4 ba · 3,307 sqft
Parklando 03
MLS ID #O6444165, JW GASTON LLC.
Listing provided by Stellar MLS
$1,450,000
100 S Virginia Ave #201
Winter Park, FL 32789
3 bd · 3 ba · 2,756 sqft
Winter Park Residential
MLS ID #O6442678, KELLY PRICE & COMPANY LLC.
Listing provided by Stellar MLS
$1,599,000
533 Country Club Dr
Winter Park, FL 32789
4 bd · 4 ba · 2,942 sqft
Lake Killarney Shores
MLS ID #O6440841, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$1,250,000
120 Broadview Ave
Winter Park, FL 32789
3 bd · 2 ba · 1,747 sqft
Killarney Estates
MLS ID #O6440960, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$3,695,999
1742 Temple Dr
Winter Park, FL 32789
4 bd · 5 ba · 3,658 sqft
Lake Knowles Terrace Add 02
MLS ID #O6443437, ROI AVE LLC.
Listing provided by Stellar MLS
$659,000
5303 Pine Lily Cir
Winter Park, FL 32792
3 bd · 2 ba · 2,265 sqft
Sanctuary At Aloma
MLS ID #O6443662, PM ELITE REALTY LLC.
Listing provided by Stellar MLS
$599,000
4260 Bear Gully Rd
Winter Park, FL 32792
4 bd · 4 ba · 2,322 sqft
Bear Gully Forest
MLS ID #O6443414, WRA BUSINESS & REAL ESTATE.
Listing provided by Stellar MLS
$3,495,000
662 Granville Drive
Winter Park, FL 32789
5 bd · 6 ba · 4,478 sqft
Park Grove
MLS ID #O6442030, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$1,095,000
1517 Harmon Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,135 sqft
Lawndale
MLS ID #O6443217, BEYCOME OF FLORIDA LLC.
Listing provided by Stellar MLS
$699,000
250 Carolina Ave #202
Winter Park, FL 32789
3 bd · 2 ba · 1,450 sqft
Park West Condo
MLS ID #O6442686, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$5,500,000
1166 Palmer Ave
Winter Park, FL 32789
5 bd · 7 ba · 5,181 sqft
Palmer Ave Lakeside Prop
MLS ID #O6442798, KELLER WILLIAMS ADVANTAGE REALTY.
Listing provided by Stellar MLS
$2,095,000
555 E Lake Sue Ave
Winter Park, FL 32789
4 bd · 4 ba · 3,776 sqft
Lake Virgina Shores
MLS ID #O6442775, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$925,000
2572 Fifeshire Dr
Winter Park, FL 32792
4 bd · 3 ba · 2,578 sqft
Brookshire Heights 2nd Add
MLS ID #O6442325, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$675,000
2215 Woodcrest Dr
Winter Park, FL 32792
4 bd · 2 ba · 1,688 sqft
Kenilworth Estates 1st Add
MLS ID #O6442348, KELLER WILLIAMS WINTER PARK.
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 2, 2026, 195 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 $770,000 and $2,090,000. That count includes 165 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 $528 per square foot (active listings in Winter Park, October 2, 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 (43%) of the active homes $500K and up in Winter Park are listed below their original asking price, by a median of 6%, as of October 2, 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 2, 2026, the homes $500K and up for sale in Winter Park have been listed a median of 65 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?+
55 homes $500K and up in Winter Park show as pending or under contract as of October 2, 2026, alongside 195 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 2, 2026 at 5:15 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.