Winter Park Homes $1M–$2M for Sale
Every home priced $1M–$2M 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, 61 homes $1M–$2M are listed for sale in Winter Park (ZIPs 32789 and 32792), from $1,049,000 to $1,999,900, with a median list price of about $1,550,000 (about $548 per square foot). That count includes 55 single-family homes, 4 townhomes or villas and 2 condominiums; single-family homes alone have a median list price of $1,550,000. Listings have been up a median of 82 days; 2 came on the market in the last 7 days; 27 (44%) have cut the asking price, by a median of 7.1%; 20 more are already under contract. Source: active listings on Stellar MLS via MLS GRID.
- for sale
- 61
- median list price
- $1,550,000
- median price / sq ft
- $548
- median days listed
- 82 days
- new in last 7 days
- 2
- price reductions
- 27 (44%)
- under contract
- 20
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 61 Homes $1M–$2M in Winter Park
$1,999,900
1133 Bella Lago Cv
Winter Park, FL 32792
3 bd · 2 ba · 1,765 sqft
None
MLS ID #O6425181, LPT REALTY, LLC.
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
751 Pansy Ave
Winter Park, FL 32789
3 bd · 4 ba · 2,703 sqft
Dixie Terrace
MLS ID #O6432554, ONE LUXURY INTERNATIONAL LLC.
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
$1,949,500
1420 Aloma Ave
Winter Park, FL 32789
3 bd · 4 ba · 2,422 sqft
Sylvan Lake Shores
MLS ID #O6430343, METROPOLITAN R.E SOLUTIONS INC.
Listing provided by Stellar MLS
$1,925,000
2260 Mulbry Dr
Winter Park, FL 32789
5 bd · 4 ba · 3,246 sqft
Lake Forest Park
MLS ID #O6441026, KONA REALTY SERVICES LLC.
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
$1,875,000
922 N Pennsylvania Ave
Winter Park, FL 32789
4 bd · 4 ba · 3,440 sqft
Tantum Add
MLS ID #O6424685, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$1,829,000
1550 Palm Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,706 sqft
Lake Knowles Terrace 2nd Add
MLS ID #O6436458, RE/MAX 200 REALTY.
Listing provided by Stellar MLS
$1,800,000
281 Brewer Ave
Winter Park, FL 32789
5 bd · 5 ba · 4,029 sqft
Osceola Shores Sec 02
MLS ID #O6424364, HENTHORN REAL ESTATE.
Listing provided by Stellar MLS
$1,775,000
101 S New York Ave #311
Winter Park, FL 32789
3 bd · 4 ba · 3,112 sqft
Winter Park Residential
MLS ID #O6416927, KELLY PRICE & COMPANY LLC.
Listing provided by Stellar MLS
$1,750,000
1750 Carollee Lane
Winter Park, FL 32789
4 bd · 4 ba · 3,249 sqft
Green Terrace V/140 Lot 3 Blk B
MLS ID #O6391179, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$1,750,000
1840 Anzle Ave
Winter Park, FL 32789
4 bd · 3 ba · 2,350 sqft
Sylvan Heights
MLS ID #O6374102, B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE.
Listing provided by Stellar MLS
$1,749,000
2525 Lafayette Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,715 sqft
Winter Park Village
MLS ID #O6428823, CORCORAN PREMIER REALTY.
Listing provided by Stellar MLS
$1,725,000
1840 Bryan Ave
Winter Park, FL 32789
4 bd · 4 ba · 3,727 sqft
Lakeview Terrace
MLS ID #O6431360, REAL BROKER, LLC.
Listing provided by Stellar MLS
$1,699,000
2343 Versailles Ave
Winter Park, FL 32789
4 bd · 4 ba · 3,307 sqft
Fontainebleau
MLS ID #O6432029, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$1,699,000
2308 Mulbry Dr
Winter Park, FL 32789
4 bd · 4 ba · 2,530 sqft
Lake Forest Park
MLS ID #O6432803, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$1,649,000
1903 N Park Ave
Winter Park, FL 32789
4 bd · 4 ba · 2,807 sqft
Twin Acres
MLS ID #O6375766, CREEGAN GROUP.
Listing provided by Stellar MLS
$1,625,000
2407 Lafayette Ave
Winter Park, FL 32789
5 bd · 5 ba · 3,133 sqft
Fontainebleau
MLS ID #O6431314, FANNIE HILLMAN & ASSOCIATES.
Listing provided by Stellar MLS
$1,600,000
723 Symonds Ave
Winter Park, FL 32789
4 bd · 4 ba · 3,065 sqft
Horton Aaron
MLS ID #O6406823, KELLER WILLIAMS WINTER PARK.
Listing provided by Stellar MLS
$1,600,000
2207 Kindel Ave
Winter Park, FL 32789
3 bd · 3 ba · 2,733 sqft
Albert Lee Ridge Annex
MLS ID #O6436815, THE SIMON SIMAAN GROUP.
Listing provided by Stellar MLS
$1,600,000
250 Killarney
Winter Park, FL 32789
4 bd · 4 ba · 2,568 sqft
Killarney Estates
MLS ID #O6419382, FLORIDA PROPERTY SPECIALIST.
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
$1,599,000
1864 Grinnell Ter
Winter Park, FL 32789
5 bd · 4 ba · 3,028 sqft
Fremar
MLS ID #O6403822, COLDWELL BANKER 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 $1M–$2M are for sale in Winter Park right now?+
As of October 2, 2026, 61 homes $1M–$2M are listed for sale in Winter Park (ZIPs 32789 and 32792), priced from $1,049,000 to $1,999,900; the middle half are listed between $1,350,000 and $1,700,000. That count includes 55 single-family homes, 4 townhomes or villas and 2 condominiums; single-family homes alone have a median list price of $1,550,000. This updates automatically from the Stellar MLS.
What is the median list price for homes $1M–$2M in Winter Park?+
The median list price is about $1,550,000, roughly $548 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 $1M–$2M in Winter Park?+
27 (44%) of the active homes $1M–$2M in Winter Park are listed below their original asking price, by a median of 7.1%, 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 $1M–$2M in Winter Park been on the market?+
As of October 2, 2026, the homes $1M–$2M for sale in Winter Park have been listed a median of 82 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 $1M–$2M in Winter Park are already under contract?+
20 homes $1M–$2M in Winter Park show as pending or under contract as of October 2, 2026, alongside 61 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 5:42 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.