Winter Park Homes Over $2M for Sale
Every home priced over $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, 51 homes over $2M are listed for sale in Winter Park (ZIPs 32789 and 32792), from $2,050,000 to $6,995,000, with a median list price of about $3,265,000 (about $820 per square foot). That count includes 45 single-family homes, 4 townhomes or villas and 2 condominiums; single-family homes alone have a median list price of $3,300,000. Listings have been up a median of 53 days; 12 (24%) have cut the asking price, by a median of 6.4%; 12 more are already under contract. Source: active listings on Stellar MLS via MLS GRID.
- for sale
- 51
- median list price
- $3,265,000
- median price / sq ft
- $820
- median days listed
- 53 days
- new in last 7 days
- 0
- price reductions
- 12 (24%)
- under contract
- 12
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 51 Homes Over $2M in Winter Park
$6,995,000
901 Golfview Ter
Winter Park, FL 32789
5 bd · 6 ba · 5,479 sqft
Golfview Terrace
MLS ID #O6437917, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$6,900,000
1260 Alabama Dr
Winter Park, FL 32789
6 bd · 7 ba · 6,396 sqft
J Kronenberger Sub
MLS ID #O6387200, KELLY PRICE & COMPANY LLC.
Listing provided by Stellar MLS
$6,195,000
698 N New York Ave
Winter Park, FL 32789
5 bd · 6 ba · 5,096 sqft
Greens/Pk
MLS ID #O6439388, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$6,000,000
1571 Woodland Ave
Winter Park, FL 32789
5 bd · 8 ba · 7,397 sqft
Comstock Park
MLS ID #O6411706, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$5,999,990
2661 Via Tuscany
Winter Park, FL 32789
4 bd · 5 ba · 3,880 sqft
Maitland Shores First Add
MLS ID #O6439181, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$5,600,000
2228 Azalea Pl
Winter Park, FL 32789
5 bd · 6 ba · 5,152 sqft
Maitland Shores First Add
MLS ID #O6416342, COMPASS FLORIDA LLC.
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
$5,195,900
825 Palmer Ave
Winter Park, FL 32789
5 bd · 7 ba · 5,122 sqft
J Kronenberger Sub
MLS ID #O6435679, CORCORAN PREMIER REALTY.
Listing provided by Stellar MLS
$4,700,000
231 Chelton Cir
Winter Park, FL 32789
4 bd · 7 ba · 5,550 sqft
Forest Hills
MLS ID #O6414890, BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY.
Listing provided by Stellar MLS
$4,400,000
702 Via Bella
Winter Park, FL 32789
4 bd · 6 ba · 3,720 sqft
Palmer Ave Lakeside Prop
MLS ID #O6437125, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$4,350,000
857 Brock St
Winter Park, FL 32789
5 bd · 6 ba · 4,827 sqft
Park Grove
MLS ID #O6432219, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$4,325,000
250 W Reading Way
Winter Park, FL 32789
5 bd · 5 ba · 4,853 sqft
Forrest Hills
MLS ID #O6441165, RE/MAX 200 REALTY.
Listing provided by Stellar MLS
$3,995,000
1441 Cardinal Ct
Winter Park, FL 32789
4 bd · 6 ba · 4,066 sqft
Winflor Court Pt Rep
MLS ID #O6399395, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$3,950,000
540 N Pennsylvania Ave
Winter Park, FL 32789
4 bd · 2 ba · 1,652 sqft
Winter Park
MLS ID #O6436046, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$3,895,000
125 S Interlachen Ave #1
Winter Park, FL 32789
3 bd · 5 ba · 3,878 sqft
South Interlachen Place
MLS ID #O6428952, COLLADO REAL ESTATE.
Listing provided by Stellar MLS
$3,890,000
620 Virginia Dr
Winter Park, FL 32789
6 bd · 5 ba · 4,677 sqft
Timberlane Shores
MLS ID #O6432790, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$3,750,000
2622 Lake Howell Ln
Winter Park, FL 32792
4 bd · 3 ba · 3,377 sqft
Acreage & Unrec
MLS ID #O6433534, THE AGENCY FL.
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
$3,600,000
207 E Kings Way
Winter Park, FL 32789
5 bd · 5 ba · 3,719 sqft
Charmont
MLS ID #O6337304, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$3,600,000
276 Detmar Dr
Winter Park, FL 32789
4 bd · 5 ba · 4,202 sqft
Detmar Terrace Winter Park
MLS ID #O6434825, CALL IT CLOSED INTL REALTY.
Listing provided by Stellar MLS
$3,500,000
2240 Venetian Way
Winter Park, FL 32789
4 bd · 4 ba · 4,036 sqft
Maitland Shores 1st Add
MLS ID #O6413398, COLDWELL BANKER REALTY.
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
$3,395,000
160 W Rockwood Way
Winter Park, FL 32789
5 bd · 6 ba · 4,015 sqft
Forest Hills
MLS ID #O6437722, PREMIER SOTHEBY'S INTL. REALTY.
Listing provided by Stellar MLS
$3,300,000
1627 Mizell Ave
Winter Park, FL 32789
5 bd · 6 ba · 3,421 sqft
Sylvan Lake Shores
MLS ID #O6406300, PREMIER SOTHEBY'S INTL. 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 over $2M are for sale in Winter Park right now?+
As of October 2, 2026, 51 homes over $2M are listed for sale in Winter Park (ZIPs 32789 and 32792), priced from $2,050,000 to $6,995,000; the middle half are listed between $2,475,000 and $3,995,000. That count includes 45 single-family homes, 4 townhomes or villas and 2 condominiums; single-family homes alone have a median list price of $3,300,000. This updates automatically from the Stellar MLS.
What is the median list price for homes over $2M in Winter Park?+
The median list price is about $3,265,000, roughly $820 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 over $2M in Winter Park?+
12 (24%) of the active homes over $2M in Winter Park are listed below their original asking price, by a median of 6.4%, 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 over $2M in Winter Park been on the market?+
As of October 2, 2026, the homes over $2M for sale in Winter Park have been listed a median of 53 days, and 0 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 over $2M in Winter Park are already under contract?+
12 homes over $2M in Winter Park show as pending or under contract as of October 2, 2026, alongside 51 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 11:52 AM 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.