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 November 11, 2026, 447 homes $500K and up are listed for sale in Winter Garden (ZIP 34787, which includes Horizon West and Oakland), from $502,500 to $5,995,000, with a median list price of about $790,000 (about $277 per square foot). That count includes 421 single-family homes, 26 townhomes or villas; single-family homes alone have a median list price of $800,000. Listings have been up a median of 63 days; 37 came on the market in the last 7 days; 220 (49%) have cut the asking price, by a median of 4%; 164 more are already under contract. Source: active listings on Stellar MLS via MLS GRID.
- for sale
- 447
- median list price
- $790,000
- median price / sq ft
- $277
- median days listed
- 63 days
- new in last 7 days
- 37
- price reductions
- 220 (49%)
- under contract
- 164
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 447 Homes $500K and Up in the Winter Garden area
$1,099,990
17449 Water Hemlock Rd
Winter Garden, FL 34787
5 bd · 5 ba · 3,825 sqft
Lake Star At Ovation
MLS ID #O6456119, KELLER WILLIAMS ADVANTAGE REALTY.
Listing provided by Stellar MLS
$869,990
17437 Water Hemlock Rd
Winter Garden, FL 34787
4 bd · 4 ba · 2,908 sqft
Lake Star At Ovation
MLS ID #O6456066, KELLER WILLIAMS ADVANTAGE REALTY.
Listing provided by Stellar MLS
$859,990
17443 Water Hemlock Rd
Winter Garden, FL 34787
4 bd · 3 ba · 2,754 sqft
Lake Star At Ovation
MLS ID #O6456099, KELLER WILLIAMS ADVANTAGE REALTY.
Listing provided by Stellar MLS
$829,496
6099 Flowering Cherry Bnd
Winter Garden, FL 34787
4 bd · 3 ba · 3,038 sqft
Avalon Woods
MLS ID #G5120149, OLYMPUS EXECUTIVE REALTY INC.
Listing provided by Stellar MLS
$655,000
17385 Bal Harbour Dr
Winter Garden, FL 34787
4 bd · 3 ba · 2,580 sqft
Waterside/Johns Lk-Ph 2b
MLS ID #S5161214, MULTI CHOICE REALTY LLC.
Listing provided by Stellar MLS
$640,000
2004 Lake Roberts Landing Dr
Winter Garden, FL 34787
4 bd · 3 ba · 2,642 sqft
Lake Roberts Landing
MLS ID #O6456161, NOVA REAL ESTATE SERVICES INC.
Listing provided by Stellar MLS
$860,000
9218 Holliston Creek Pl
Winter Garden, FL 34787
4 bd · 4 ba · 3,087 sqft
Watermark Ph 2b
MLS ID #O6456443, WRA BUSINESS & REAL ESTATE.
Listing provided by Stellar MLS
$650,000
15530 Kinnow Mandarin Ln
Winter Garden, FL 34787
3 bd · 3 ba · 2,579 sqft
Summerlakes / Highlands At Summerlake Groves
MLS ID #O6456320, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$599,000
5531 Myrtle Pine Ln
Winter Garden, FL 34787
4 bd · 3 ba · 2,703 sqft
Orchard Hills Ph 3
MLS ID #O6456000, LOKATION.
Listing provided by Stellar MLS
$860,000
15348 Firelight Dr
Winter Garden, FL 34787
6 bd · 4 ba · 3,877 sqft
Belle Meade Ph 02 H
MLS ID #O6456009, LPT REALTY, LLC.
Listing provided by Stellar MLS
$1,570,000
1076 Sadler Oaks Way
Oakland, FL 34787
4 bd · 4 ba · 3,589 sqft
Oakland Park
MLS ID #O6455257, BHHS FLORIDA REALTY.
Listing provided by Stellar MLS
$1,525,000
12922 Canopy Woods Way
Winter Garden, FL 34787
5 bd · 5 ba · 4,671 sqft
Canopy Oaks Ph 1
MLS ID #S5160455, SIGNATURE COLLECTION REALTY IN.
Listing provided by Stellar MLS
$1,034,940
13011 Sunset Garden Ln
Winter Garden, FL 34787
5 bd · 5 ba · 3,894 sqft
Westhaven At Ovation
MLS ID #O6455923, ORLANDO TBI REALTY LLC.
Listing provided by Stellar MLS
$973,550
231 Tbd Dr
Winter Garden, FL 34787
5 bd · 5 ba · 3,894 sqft
Westhaven At Ovation
MLS ID #O6455929, ORLANDO TBI REALTY LLC.
Listing provided by Stellar MLS
$899,990
10732 Petrillo Way
Winter Garden, FL 34787
5 bd · 6 ba · 4,014 sqft
Winding Bay Ph 1b
MLS ID #S5160989, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$867,555
233 Tbd Dr
Winter Garden, FL 34787
4 bd · 4 ba · 3,000 sqft
Westhaven At Ovation
MLS ID #O6455925, ORLANDO TBI REALTY LLC.
Listing provided by Stellar MLS
$702,570
15162 Flannan St
Winter Garden, FL 34787
5 bd · 4 ba · 2,686 sqft
Westhaven At Ovation
MLS ID #O6455901, ORLANDO TBI REALTY LLC.
Listing provided by Stellar MLS
$659,008
12818 Sunset Walk Dr
Winter Garden, FL 34787
4 bd · 4 ba · 1,930 sqft
Westhaven At Ovation
MLS ID #O6455882, ORLANDO TBI REALTY LLC.
Listing provided by Stellar MLS
$599,900
645 Autumn Oaks Loop
Winter Garden, FL 34787
4 bd · 3 ba · 2,410 sqft
Winter Oaks
MLS ID #O6455873, INVESTOR'S REAL ESTATE LLC.
Listing provided by Stellar MLS
$539,239
12826 Sunset Walk Dr
Winter Garden, FL 34787
4 bd · 3 ba · 1,897 sqft
Westhaven At Ovation
MLS ID #O6455888, ORLANDO TBI REALTY LLC.
Listing provided by Stellar MLS
$534,170
15126 Flannan Ln
Winter Garden, FL 34787
3 bd · 3 ba · 2,062 sqft
Westhaven At Ovation
MLS ID #O6455914, ORLANDO TBI REALTY LLC.
Listing provided by Stellar MLS
$528,396
12822 Sunset Walk Dr
Winter Garden, FL 34787
3 bd · 3 ba · 1,857 sqft
Westhaven At Ovation
MLS ID #O6455895, ORLANDO TBI REALTY LLC.
Listing provided by Stellar MLS
$1,675,000
14253 Country Estate Dr
Winter Garden, FL 34787
5 bd · 5 ba · 5,504 sqft
Country Lakes
MLS ID #O6453112, ONE LUXURY INTERNATIONAL LLC.
Listing provided by Stellar MLS
$640,000
1414 Portmoor Way
Winter Garden, FL 34787
4 bd · 3 ba · 2,603 sqft
Stoneybrook West 44/134
MLS ID #O6455589, KELLER WILLIAMS ELITE PARTNERS III REALTY.
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 November 11, 2026, 447 homes $500K and up are listed for sale in Winter Garden (ZIP 34787, which includes Horizon West and Oakland), priced from $502,500 to $5,995,000; the middle half are listed between $625,000 and $945,000. That count includes 421 single-family homes, 26 townhomes or villas; 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 $790,000, roughly $277 per square foot (active listings in Winter Garden, November 11, 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?+
220 (49%) of the active homes $500K and up in Winter Garden are listed below their original asking price, by a median of 4%, as of November 11, 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 November 11, 2026, the homes $500K and up for sale in Winter Garden have been listed a median of 63 days, and 37 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?+
164 homes $500K and up in Winter Garden show as pending or under contract as of November 11, 2026, alongside 447 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 November 11, 2026 at 8:47 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.