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 22, 2026, 453 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 $780,000 (about $277 per square foot). That count includes 431 single-family homes, 21 townhomes or villas and 1 condominium; single-family homes alone have a median list price of $785,000. Listings have been up a median of 71 days; 26 came on the market in the last 7 days; 233 (51%) have cut the asking price, by a median of 3.5%; 166 more are already under contract. Source: active listings on Stellar MLS via MLS GRID.
- for sale
- 453
- median list price
- $780,000
- median price / sq ft
- $277
- median days listed
- 71 days
- new in last 7 days
- 26
- price reductions
- 233 (51%)
- under contract
- 166
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 453 Homes $500K and Up in the Winter Garden area
$518,000
524 S Highland Ave
Winter Garden, FL 34787
3 bd · 2 ba · 1,782 sqft
Rep Pt Pleasant Park Sub
MLS ID #O6451915, TARA MOORE REAL ESTATE.
Listing provided by Stellar MLS
$2,575,000
16773 Broadwater Ave
Winter Garden, FL 34787
7 bd · 6 ba · 6,235 sqft
Waterside On Johns Lake
MLS ID #O6450394, RE/MAX PRIME PROPERTIES.
Listing provided by Stellar MLS
$860,494
11390 Bourbon Rose Cir
Winter Garden, FL 34787
4 bd · 3 ba · 2,717 sqft
Esplanade At Mckinnon Groves
MLS ID #O6451559, TAYLOR MORRISON REALTY OF FLORIDA INC.
Listing provided by Stellar MLS
$620,000
108 Doe Run Dr
Winter Garden, FL 34787
4 bd · 3 ba · 2,835 sqft
Deerfield Place A-G
MLS ID #O6451420, CENTURY 21 CARIOTI.
Listing provided by Stellar MLS
$570,000
921 Westcliffe Dr
Winter Garden, FL 34787
4 bd · 3 ba · 2,354 sqft
Fullers Lndg B
MLS ID #O6449499, RE/MAX EXCLUSIVE COLLECTION.
Listing provided by Stellar MLS
$535,000
14355 Braemar St
Winter Garden, FL 34787
3 bd · 3 ba · 2,206 sqft
Highland Rdg Ph 2
MLS ID #S5160001, MY REALTY GROUP, LLC..
Listing provided by Stellar MLS
$869,000
14779 Mcclane Rd
Winter Garden, FL 34787
5 bd · 4 ba · 3,118 sqft
Oxford Chase
MLS ID #S5159916, REAL BROKER, LLC.
Listing provided by Stellar MLS
$1,895,000
16143 Barkly Ridge Ct
Winter Garden, FL 34787
6 bd · 7 ba · 5,247 sqft
Avalon Rdg
MLS ID #O6450042, DOUGLAS ELLIMAN.
Listing provided by Stellar MLS
$849,900
8270 Topsail Pl
Winter Garden, FL 34787
4 bd · 3 ba · 2,306 sqft
Lakeshore Preserve Ph 5
MLS ID #O6451144, REALTY HUB.
Listing provided by Stellar MLS
$695,000
726 Regina Cir
Oakland, FL 34787
5 bd · 4 ba · 3,641 sqft
Johns Landing Ph 01 44/47
MLS ID #O6450677, HOUWZER INC.
Listing provided by Stellar MLS
$629,900
14230 Sunridge Blvd
Winter Garden, FL 34787
3 bd · 2 ba · 2,270 sqft
Cypress Reserve Ph 1
MLS ID #O6450563, VALIANT REALTY GROUP LLC.
Listing provided by Stellar MLS
$1,150,000
816 E Fullers Cross Rd
Winter Garden, FL 34787
4 bd · 4 ba · 3,262 sqft
Crown Point Town
MLS ID #O6449104, MILLENNIUM REALTY CENTER LLC.
Listing provided by Stellar MLS
$960,200
9901 Avalon Woods Dr
Winter Garden, FL 34787
3 bd · 2 ba · 2,239 sqft
001
MLS ID #O6450619, ACME REAL ESTATE FLORIDA LLC.
Listing provided by Stellar MLS
$925,000
6262 Argent Wood Dr
Winter Garden, FL 34787
5 bd · 4 ba · 3,643 sqft
Silverleaf Oaks/Hamlin Ph 3a
MLS ID #O6450359, IVRE ORLANDO.
Listing provided by Stellar MLS
$740,000
3275 Buoy Cir
Winter Garden, FL 34787
5 bd · 5 ba · 3,663 sqft
Lakeview Preserve
MLS ID #O6449571, REDFIN CORPORATION.
Listing provided by Stellar MLS
$697,240
620 Sigler Dr
Winter Garden, FL 34787
4 bd · 3 ba · 1,852 sqft
Lakeview Village Estates
MLS ID #O6447836, DAVILA HOMES.
Listing provided by Stellar MLS
$685,240
618 Sigler Dr
Winter Garden, FL 34787
3 bd · 3 ba · 1,852 sqft
Lakeview Village Estates
MLS ID #O6447410, DAVILA HOMES.
Listing provided by Stellar MLS
$635,000
13160 Dendy Way
Winter Garden, FL 34787
3 bd · 3 ba · 2,207 sqft
Horizon Isle
MLS ID #O6450625, TALENT REALTY SOLUTIONS.
Listing provided by Stellar MLS
$604,580
622 Sigler Dr
Winter Garden, FL 34787
3 bd · 3 ba · 1,634 sqft
Lakeview Village Estates
MLS ID #O6447381, DAVILA HOMES.
Listing provided by Stellar MLS
$1,749,000
728 Garden West Ter
Winter Garden, FL 34787
5 bd · 5 ba · 3,555 sqft
Garden West
MLS ID #O6450273, REGENCY REAL ESTATE LLC.
Listing provided by Stellar MLS
$750,000
12934 Harvest Rain Ave
Winter Garden, FL 34787
3 bd · 4 ba · 2,858 sqft
Harvest At Ovation
MLS ID #O6450081, TAYLOR MORRISON REALTY OF FLORIDA INC.
Listing provided by Stellar MLS
$659,000
17055 Seville Orange Rd
Winter Garden, FL 34787
3 bd · 3 ba · 2,134 sqft
Northlake At Ovation
MLS ID #O6449811, PREMIUM PROPERTIES R.E SERVICE.
Listing provided by Stellar MLS
$654,718
14743 Field Daisy Dr
Winter Garden, FL 34787
3 bd · 5 ba · 2,618 sqft
Harvest At Ovation
MLS ID #O6450084, TAYLOR MORRISON REALTY OF FLORIDA INC.
Listing provided by Stellar MLS
$599,000
16012 Micelli Dr
Winter Garden, FL 34787
4 bd · 3 ba · 2,428 sqft
Winding Bay Ph 1b
MLS ID #O6450178, ALVES AND HOWELL 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 October 22, 2026, 453 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 $620,000 and $925,000. That count includes 431 single-family homes, 21 townhomes or villas and 1 condominium; single-family homes alone have a median list price of $785,000. 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 $780,000, roughly $277 per square foot (active listings in Winter Garden, October 22, 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?+
233 (51%) 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 22, 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 22, 2026, the homes $500K and up for sale in Winter Garden have been listed a median of 71 days, and 26 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?+
166 homes $500K and up in Winter Garden show as pending or under contract as of October 22, 2026, alongside 453 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 22, 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 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.