Winter Garden Homes $500K and Up for Sale
Every home priced $500K and up currently for sale in Winter Garden — pulled live from the Stellar MLS and updated continuously. Pair this with the free Winter Garden 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, 422 homes $500K and up are listed for sale in Winter Garden (ZIP 34787, which includes Horizon West and Oakland), from $500,000 to $5,995,000, with a median list price of about $795,000 (about $278 per square foot). That count includes 401 single-family homes, 20 townhomes or villas and 1 condominium; single-family homes alone have a median list price of $800,000. Listings have been up a median of 71 days; 45 came on the market in the last 7 days; 210 (50%) have cut the asking price, by a median of 3.5%; 169 more are already under contract. Source: active listings on Stellar MLS via MLS GRID.
- for sale
- 422
- median list price
- $795,000
- median price / sq ft
- $278
- median days listed
- 71 days
- new in last 7 days
- 45
- price reductions
- 210 (50%)
- under contract
- 169
Active listings on Stellar MLS via MLS GRID in ZIP 34787, which includes Horizon West and Oakland, including condos and townhomes, updated automatically. List prices are asking prices, not sale prices.
Newest 24 of 422 Homes $500K and Up in Winter Garden
$740,500
12349 Westfield Lakes Cir
Winter Garden, FL 34787
4 bd · 3 ba · 2,777 sqft
Westfield Lakes Ph 04 A-F
MLS ID #O6445527, KELLER WILLIAMS ADVANTAGE REALTY.
Listing provided by Stellar MLS
$589,900
517 Garden Heights Dr
Winter Garden, FL 34787
4 bd · 2 ba · 1,960 sqft
Garden Heights
MLS ID #O6446560, LOKATION.
Listing provided by Stellar MLS
$585,000
1442 Coluso Dr
Winter Garden, FL 34787
3 bd · 2 ba · 2,133 sqft
Magnolia Wood Fifth Add
MLS ID #V4951594, RE/MAX ADVANTAGE.
Listing provided by Stellar MLS
$560,000
4540 Gliding Wave St
Winter Garden, FL 34787
3 bd · 2 ba · 2,144 sqft
Lakeview Preserve Ph 2
MLS ID #O6442258, RUBIO REALTY INVESTMENTS LLC.
Listing provided by Stellar MLS
$550,000
9918 Pallida Hickory Way
Winter Garden, FL 34787
3 bd · 3 ba · 1,892 sqft
Water Mark Phase 4
MLS ID #O6445324, REAL BROKER, LLC.
Listing provided by Stellar MLS
$2,400,000
7747 Green Mountain Way
Winter Garden, FL 34787
6 bd · 7 ba · 5,572 sqft
Summerlake Pd Ph 3a
MLS ID #O6445847, BELLA VIEW REALTY LLC.
Listing provided by Stellar MLS
$1,500,000
261 Zachary Wade St
Winter Garden, FL 34787
4 bd · 4 ba · 3,728 sqft
Lakeview Reserve 46/149
MLS ID #O6446065, BALDWIN PARK REALTY LLC.
Listing provided by Stellar MLS
$789,000
923 Allenhurst St
Winter Garden, FL 34787
3 bd · 2 ba · 1,978 sqft
Oakland Park
MLS ID #O6444634, FLORIDA REALTY MARKETPLACE.
Listing provided by Stellar MLS
$569,900
4780 Terrace Bluff St
Winter Garden, FL 34787
4 bd · 4 ba · 2,342 sqft
Enclave/Hamlin
MLS ID #O6446681, COMPASS FLORIDA LLC.
Listing provided by Stellar MLS
$4,300,000
15614 Espalier Way
Winter Garden, FL 34787
5 bd · 7 ba · 6,601 sqft
Signature Lakes Ph 2
MLS ID #O6445414, WRA BUSINESS & REAL ESTATE.
Listing provided by Stellar MLS
$1,100,000
206 N Highland Ave
Winter Garden, FL 34787
3 bd · 3 ba · 1,950 sqft
Cooper & Sewell Add
MLS ID #O6444632, HOMEVEST REALTY.
Listing provided by Stellar MLS
$925,000
313 Merin Ct
Winter Garden, FL 34787
4 bd · 3 ba · 2,860 sqft
Lake Cove Pointe 46/58
MLS ID #O6444052, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$910,000
1362 Union Club Dr
Winter Garden, FL 34787
3 bd · 3 ba · 1,822 sqft
Oakland Parka F1 & F2
MLS ID #O6443584, OAK AVENUE REAL ESTATE LLC.
Listing provided by Stellar MLS
$865,000
1021 Huntspoint St
Winter Garden, FL 34787
4 bd · 4 ba · 2,445 sqft
Oakland Park
MLS ID #O6445538, BHHS FLORIDA REALTY.
Listing provided by Stellar MLS
$849,000
3413 Turningwind Ln
Winter Garden, FL 34787
4 bd · 3 ba · 2,917 sqft
Windward Cay
MLS ID #O6445840, FOLIO REALTY LLC.
Listing provided by Stellar MLS
$790,000
15007 Night Heron Dr
Winter Garden, FL 34787
5 bd · 4 ba · 3,874 sqft
Summerlake Pd Ph 3b
MLS ID #O6438331, TALENT REALTY SOLUTIONS.
Listing provided by Stellar MLS
$635,000
16283 Honey Harvest St
Winter Garden, FL 34787
4 bd · 5 ba · 2,927 sqft
Harvest/Ovation
MLS ID #O6446119, KELLER WILLIAMS ELITE PARTNERS III REALTY.
Listing provided by Stellar MLS
$575,000
995 Sadie Ln
Winter Garden, FL 34787
4 bd · 2 ba · 2,005 sqft
Island Pointe Sub
MLS ID #O6445793, OLYMPUS EXECUTIVE REALTY INC.
Listing provided by Stellar MLS
$525,000
7584 Summerlake Groves St
Winter Garden, FL 34787
3 bd · 3 ba · 2,175 sqft
Panther View
MLS ID #O6446076, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$515,000
6329 Manuscript St
Winter Garden, FL 34787
5 bd · 4 ba · 2,379 sqft
Signature Lakes Ph 02 A B H I J
MLS ID #O6445557, CARDINAL REALTY GROUP, LLC..
Listing provided by Stellar MLS
$1,175,000
8836 Lakeshore Pointe Dr
Winter Garden, FL 34787
4 bd · 4 ba · 2,914 sqft
Lakeshore Preserve Ph 1
MLS ID #O6421088, THE AGENCY FL.
Listing provided by Stellar MLS
$974,706
11851 Shine View Ln
Winter Garden, FL 34787
4 bd · 4 ba · 3,327 sqft
Waterleigh
MLS ID #O6445304, DR HORTON REALTY OF CENTRAL FLORIDA LLC.
Listing provided by Stellar MLS
$912,961
11929 Shine View Ln
Winter Garden, FL 34787
4 bd · 4 ba · 3,327 sqft
Waterleigh
MLS ID #O6445293, DR HORTON REALTY OF CENTRAL FLORIDA LLC.
Listing provided by Stellar MLS
$799,900
15562 Waterleigh Cove Dr
Winter Garden, FL 34787
4 bd · 4 ba · 2,962 sqft
Waterleigh Phase 1a
MLS ID #O6445203, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
More Winter Garden Homes for Sale
Winter Garden buyer questions
How many homes $500K and up are for sale in Winter Garden right now?+
As of October 2, 2026, 422 homes $500K and up are listed for sale in Winter Garden (ZIP 34787, which includes Horizon West and Oakland), priced from $500,000 to $5,995,000; the middle half are listed between $625,000 and $950,000. That count includes 401 single-family homes, 20 townhomes or villas and 1 condominium; single-family homes alone have a median list price of $800,000. This updates automatically from the Stellar MLS.
What is the median list price for homes $500K and up in Winter Garden?+
The median list price is about $795,000, roughly $278 per square foot (active listings in Winter Garden, 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 Garden?+
210 (50%) of the active homes $500K and up in Winter Garden are listed below their original asking price, by a median of 3.5%, 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 Garden been on the market?+
As of October 2, 2026, the homes $500K and up for sale in Winter Garden have been listed a median of 71 days, and 45 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 Garden are already under contract?+
169 homes $500K and up in Winter Garden show as pending or under contract as of October 2, 2026, alongside 422 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 Garden?+
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 5:16 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 Garden?
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.