Winter Park Homes $750K–$1M for Sale
Every home priced $750K–$1M 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, 36 homes $750K–$1M are listed for sale in Winter Park (ZIPs 32789 and 32792), from $769,000 to $999,500, with a median list price of about $855,000 (about $390 per square foot). That count includes 28 single-family homes, 4 townhomes or villas and 4 condominiums; single-family homes alone have a median list price of $850,000. Listings have been up a median of 58 days; 3 came on the market in the last 7 days; 18 (50%) have cut the asking price, by a median of 5.6%; 4 more are already under contract. Source: active listings on Stellar MLS via MLS GRID.
- for sale
- 36
- median list price
- $855,000
- median price / sq ft
- $390
- median days listed
- 58 days
- new in last 7 days
- 3
- price reductions
- 18 (50%)
- under contract
- 4
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 36 Homes $750K–$1M in Winter Park
$999,500
1220 Howell Branch Rd
Winter Park, FL 32789
3 bd · 2 ba · 1,487 sqft
Lake Maitland
MLS ID #O6437591, PARK PLACE REAL ESTATE.
Listing provided by Stellar MLS
$999,000
616 Brechin Dr
Winter Park, FL 32792
4 bd · 5 ba · 2,638 sqft
Kenilworth Shores Sec 04
MLS ID #O6409911, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$989,500
269 E Canton Ave #269
Winter Park, FL 32789
1 bd · 2 ba · 1,109 sqft
Village Winterset Inc
MLS ID #O6404706, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$985,000
2667 Cochise Trl
Winter Park, FL 32789
4 bd · 3 ba · 2,868 sqft
Park Pointe Rep
MLS ID #O6429844, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$960,000
447 N Phelps Ave
Winter Park, FL 32789
2 bd · 1 ba · 1,290 sqft
Ethel Park
MLS ID #O6441415, KELLER WILLIAMS ADVANTAGE REALTY.
Listing provided by Stellar MLS
$950,000
471 Holt Ave
Winter Park, FL 32789
4 bd · 3 ba · 2,528 sqft
Winter Park
MLS ID #O6437590, FLORIDA HOME TEAM REALTY LLC.
Listing provided by Stellar MLS
$950,000
1256 S Pennsylvania Ave #9
Winter Park, FL 32789
3 bd · 3 ba · 1,957 sqft
Casa Jardin Condo
MLS ID #O6439864, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$950,000
913 Moss Ln
Winter Park, FL 32789
3 bd · 2 ba · 1,887 sqft
Maitland Shores First Add
MLS ID #O6441449, VECTOR REALTY.
Listing provided by Stellar MLS
$925,000
311 E Morse Blvd #4-5
Winter Park, FL 32789
2 bd · 2 ba · 1,763 sqft
Phillips Circle Rep
MLS ID #O6432808, KELLER WILLIAMS ADVANTAGE REALTY.
Listing provided by Stellar MLS
$925,000
3006 Northwood Blvd
Winter Park, FL 32789
4 bd · 3 ba · 2,075 sqft
Northwood Terrace
MLS ID #O6419056, ORLANDO HOMES GROUP LLC.
Listing provided by Stellar MLS
$925,000
1138 S Pennsylvania Ave
Winter Park, FL 32789
3 bd · 3 ba · 2,434 sqft
Virginia Heights Rep
MLS ID #O6420090, COLDWELL BANKER REALTY.
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
$918,000
Lot #21 Karolina Ave
Winter Park, FL 32789
4 bd · 3 ba · 2,662 sqft
Karolina On Killarney
MLS ID #O6387812, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$915,000
1927 S Lakemont Ave
Winter Park, FL 32792
3 bd · 4 ba · 2,093 sqft
Lake Spier Xing
MLS ID #O6426102, IAD REAL ESTATE.
Listing provided by Stellar MLS
$899,000
1621 Chestnut Ave
Winter Park, FL 32789
3 bd · 3 ba · 2,022 sqft
Lake Knowles Terrace
MLS ID #O6435086, KELLY PRICE & COMPANY LLC.
Listing provided by Stellar MLS
$899,000
560 Ololu Dr
Winter Park, FL 32789
2 bd · 2 ba · 1,086 sqft
Killarney Circle
MLS ID #O6344540, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$895,000
618 Blairshire Cir
Winter Park, FL 32792
4 bd · 3 ba · 1,876 sqft
Brookshire Heights 4th Add
MLS ID #O6439298, REAL BROKER, LLC.
Listing provided by Stellar MLS
$860,000
120 Longbranch Rd
Winter Park, FL 32792
5 bd · 4 ba · 3,284 sqft
Lake Ann Estates Unit 3
MLS ID #O6434232, OPENDOOR BROKERAGE LLC.
Listing provided by Stellar MLS
$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
$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
$850,000
2345 Brookshire Ave
Winter Park, FL 32792
3 bd · 3 ba · 2,488 sqft
Brookshire Heights
MLS ID #O6439369, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$849,000
437 N Capen Ave
Winter Park, FL 32789
3 bd · 3 ba · 1,904 sqft
Canton Ave Cottages 1
MLS ID #O6414283, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$836,000
338 Blue Heron Dr
Winter Park, FL 32789
3 bd · 3 ba · 2,017 sqft
Flamingo Shores
MLS ID #O6410174, STOCKWORTH REALTY GROUP.
Listing provided by Stellar MLS
$829,500
1521 Heron Wood Pl
Winter Park, FL 32792
4 bd · 2 ba · 3,950 sqft
None
MLS ID #O6379884, RE/MAX INNOVATION.
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 $750K–$1M are for sale in Winter Park right now?+
As of October 2, 2026, 36 homes $750K–$1M are listed for sale in Winter Park (ZIPs 32789 and 32792), priced from $769,000 to $999,500; the middle half are listed between $810,000 and $925,000. That count includes 28 single-family homes, 4 townhomes or villas and 4 condominiums; single-family homes alone have a median list price of $850,000. This updates automatically from the Stellar MLS.
What is the median list price for homes $750K–$1M in Winter Park?+
The median list price is about $855,000, roughly $390 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 $750K–$1M in Winter Park?+
18 (50%) of the active homes $750K–$1M in Winter Park are listed below their original asking price, by a median of 5.6%, 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 $750K–$1M in Winter Park been on the market?+
As of October 2, 2026, the homes $750K–$1M for sale in Winter Park have been listed a median of 58 days, and 3 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 $750K–$1M in Winter Park are already under contract?+
4 homes $750K–$1M in Winter Park show as pending or under contract as of October 2, 2026, alongside 36 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.