Winter Park Homes $500K–$750K for Sale
Every home priced $500K–$750K 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, 47 homes $500K–$750K are listed for sale in Winter Park (ZIPs 32789 and 32792), from $500,000 to $739,777, with a median list price of about $630,000 (about $330 per square foot). That count includes 37 single-family homes, 6 townhomes or villas and 4 condominiums; single-family homes alone have a median list price of $630,000. Listings have been up a median of 64 days; 2 came on the market in the last 7 days; 26 (55%) have cut the asking price, by a median of 4.9%; 19 more are already under contract. Source: active listings on Stellar MLS via MLS GRID.
- for sale
- 47
- median list price
- $630,000
- median price / sq ft
- $330
- median days listed
- 64 days
- new in last 7 days
- 2
- price reductions
- 26 (55%)
- under contract
- 19
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.
Highest-priced 24 of 47 Homes $500K–$750K in Winter Park
$739,777
4039 Cool Water Ct
Winter Park, FL 32792
4 bd · 2 ba · 2,267 sqft
Lake Waunatta Woods
MLS ID #O6437904, RE/MAX CENTRAL REALTY.
Listing provided by Stellar MLS
$739,000
250 Carolina Ave #205
Winter Park, FL 32789
2 bd · 2 ba · 1,311 sqft
Park West Condo
MLS ID #O6433913, BHHS FLORIDA REALTY.
Listing provided by Stellar MLS
$725,000
1850 Bryan Ave
Winter Park, FL 32789
3 bd · 2 ba · 1,563 sqft
Lakeview Terrace
MLS ID #O6438184, CORCORAN PREMIER REALTY.
Listing provided by Stellar MLS
$725,000
1316 Blue Stem Ln
Winter Park, FL 32792
4 bd · 3 ba · 2,196 sqft
Landings At Hawks Crest
MLS ID #O6416828, AFFINITY REALTY LLC.
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
$710,000
300 Carolina Ave #402c
Winter Park, FL 32789
3 bd · 2 ba · 1,350 sqft
Park West Condo
MLS ID #O6410016, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$699,500
1418 Lone Feather Trl
Winter Park, FL 32792
4 bd · 3 ba · 2,197 sqft
Landings At Hawks Crest
MLS ID #O6417341, PREMIER SOTHEBY'S INTL. REALTY.
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
$695,000
715 S Ranger Blvd
Winter Park, FL 32792
4 bd · 3 ba · 2,312 sqft
Winter Park Pines
MLS ID #O6410899, DAHLIA REALTY GROUP.
Listing provided by Stellar MLS
$680,000
432 W Swoope Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,664 sqft
Swoope Park
MLS ID #O6375719, COLDWELL BANKER RESIDENTIAL RE.
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
$675,000
2260 Coldstream Dr
Winter Park, FL 32792
4 bd · 2 ba · 1,509 sqft
Brookshire Heights
MLS ID #O6437438, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$669,900
433 Gilbert Rd
Winter Park, FL 32792
3 bd · 2 ba · 1,800 sqft
Winter Park Pines
MLS ID #O6428430, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$665,000
1122 Wildmeadow Run
Winter Park, FL 32792
4 bd · 3 ba · 1,770 sqft
Meadows At Hawks Crest
MLS ID #O6429492, REAL BROKER, LLC.
Listing provided by Stellar MLS
$664,000
900 Carver St
Winter Park, FL 32789
3 bd · 3 ba · 1,794 sqft
Magnolia Gardens Sub
MLS ID #O6435435, EXP REALTY LLC.
Listing provided by Stellar MLS
$660,000
1016 Aragon Ave
Winter Park, FL 32789
4 bd · 4 ba · 1,840 sqft
Seville Park
MLS ID #O6433576, PALMANO GROUP RE BROKERAGE LLC.
Listing provided by Stellar MLS
$660,000
1256 Melissa Ct
Winter Park, FL 32789
3 bd · 3 ba · 1,690 sqft
Waterbridge
MLS ID #O6432855, KELLER WILLIAMS REALTY AT THE PARKS.
Listing provided by Stellar MLS
$659,900
274 N Ranger Blvd
Winter Park, FL 32792
3 bd · 2 ba · 1,420 sqft
Winter Park Pines
MLS ID #O6440062, EXPLORE FLORIDA REALTY SERVICES 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
$655,000
2831 Mulford Ave
Winter Park, FL 32789
4 bd · 3 ba · 1,647 sqft
Orangewood Park
MLS ID #O6414319, UNITED REAL ESTATE PREFERRED.
Listing provided by Stellar MLS
$650,000
943 Fairway Dr
Winter Park, FL 32792
4 bd · 3 ba · 2,067 sqft
Golfside Sec 03
MLS ID #O6426672, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$649,900
840 W Canton Ave
Winter Park, FL 32789
3 bd · 2 ba · 1,370 sqft
N/A
MLS ID #O6412754, REAL BROKER, LLC.
Listing provided by Stellar MLS
$649,900
860 N Denning Dr
Winter Park, FL 32789
3 bd · 3 ba · 1,411 sqft
Magnolia Gardens Sub
MLS ID #O6412589, OUTLET REALTY.
Listing provided by Stellar MLS
$630,000
2600 Euston Rd
Winter Park, FL 32789
6 bd · 3 ba · 3,145 sqft
Glencoe Sub
MLS ID #O6397890, AROD PARTNERS REALTY.
Listing provided by Stellar MLS
More Winter Park Homes for Sale
All Winter Park homes $500K and up, with the live market brief →
Winter Park buyer questions
How many homes $500K–$750K are for sale in Winter Park right now?+
As of October 2, 2026, 47 homes $500K–$750K are listed for sale in Winter Park (ZIPs 32789 and 32792), priced from $500,000 to $739,777; the middle half are listed between $575,000 and $675,000. That count includes 37 single-family homes, 6 townhomes or villas and 4 condominiums; single-family homes alone have a median list price of $630,000. This updates automatically from the Stellar MLS.
What is the median list price for homes $500K–$750K in Winter Park?+
The median list price is about $630,000, roughly $330 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–$750K in Winter Park?+
26 (55%) of the active homes $500K–$750K in Winter Park are listed below their original asking price, by a median of 4.9%, 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–$750K in Winter Park been on the market?+
As of October 2, 2026, the homes $500K–$750K for sale in Winter Park have been listed a median of 64 days, and 2 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–$750K in Winter Park are already under contract?+
19 homes $500K–$750K in Winter Park show as pending or under contract as of October 2, 2026, alongside 47 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 5:11 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.