Winter Garden Homes $1M–$2M for Sale
Every home priced $1M–$2M 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, 64 homes $1M–$2M are listed for sale in Winter Garden (ZIP 34787, which includes Horizon West and Oakland), from $1,000,000 to $1,999,000, with a median list price of about $1,200,000 (about $359 per square foot). That count includes 62 single-family homes, 2 townhomes or villas; single-family homes alone have a median list price of $1,200,000. Listings have been up a median of 92 days; 5 came on the market in the last 7 days; 26 (41%) have cut the asking price, by a median of 8.4%; 18 more are already under contract. Source: active listings on Stellar MLS via MLS GRID.
- for sale
- 64
- median list price
- $1,200,000
- median price / sq ft
- $359
- median days listed
- 92 days
- new in last 7 days
- 5
- price reductions
- 26 (41%)
- under contract
- 18
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.
Highest-priced 24 of 64 Homes $1M–$2M in Winter Garden
$1,999,000
9110 Morgana Ct
Winter Garden, FL 34787
5 bd · 5 ba · 4,661 sqft
Avalon Cove
MLS ID #O6409413, MAINFRAME REAL ESTATE.
Listing provided by Stellar MLS
$1,999,000
16077 Barkly Ridge Ct
Winter Garden, FL 34787
6 bd · 7 ba · 5,248 sqft
Avalon Ridge
MLS ID #O6429381, MS LAND & BUILDING LLC.
Listing provided by Stellar MLS
$1,975,000
1106 Sarah Mathews Dr
Oakland, FL 34787
5 bd · 6 ba · 3,596 sqft
Grove At The Harvest District
MLS ID #O6375487, REGENCY REAL ESTATE LLC.
Listing provided by Stellar MLS
$1,950,000
15680 Panther Lake Dr
Winter Garden, FL 34787
5 bd · 6 ba · 4,329 sqft
Lakeshore Preserve Ph 2
MLS ID #O6438584, KELLER WILLIAMS CLASSIC.
Listing provided by Stellar MLS
$1,924,999
15210 E Oakland Ave
Winter Garden, FL 34787
4 bd · 3 ba · 3,789 sqft
Oakland Hills
MLS ID #O6442327, EXP REALTY LLC.
Listing provided by Stellar MLS
$1,790,000
16945 W Phil C Peters Rd
Winter Garden, FL 34787
6 bd · 4 ba · 4,396 sqft
Na
MLS ID #O6418208, WINDERMERE COCOA BEACH CENTER.
Listing provided by Stellar MLS
$1,775,000
17224 Old Country Ln
Winter Garden, FL 34787
6 bd · 4 ba · 3,629 sqft
Lake Avalon Groves Rep
MLS ID #O6384075, LOKATION.
Listing provided by Stellar MLS
$1,750,000
7573 Green Mountain Way
Winter Garden, FL 34787
4 bd · 4 ba · 3,388 sqft
West Lake Hancock Estates
MLS ID #O6429288, PRISTINE INTERNATIONAL REALTY LLC.
Listing provided by Stellar MLS
$1,725,000
906 Allendale Ln
Winter Garden, FL 34787
5 bd · 4 ba · 3,784 sqft
Oakland Park B-2
MLS ID #G5107489, CENTURY 21 CARIOTI.
Listing provided by Stellar MLS
$1,724,500
8750 Bayview Crossing Dr
Winter Garden, FL 34787
5 bd · 6 ba · 4,641 sqft
Waterleigh Ph 1
MLS ID #O6416046, CHARLES RUTENBERG REALTY ORLANDO.
Listing provided by Stellar MLS
$1,675,000
279 Zachary Wade St
Winter Garden, FL 34787
5 bd · 4 ba · 4,473 sqft
Lakeview Reserve
MLS ID #O6408014, INDEPENDENCE REALTY GROUP LLC.
Listing provided by Stellar MLS
$1,650,000
1032 Galston Aly
Winter Garden, FL 34787
5 bd · 5 ba · 3,506 sqft
Oakland Parka
MLS ID #O6441542, OAK AVENUE REAL ESTATE LLC.
Listing provided by Stellar MLS
$1,644,999
1101 Eagles Pass Way
Winter Garden, FL 34787
6 bd · 5 ba · 4,104 sqft
Oakland Park
MLS ID #O6408835, LAKESIDE REALTY WINDERMERE INC.
Listing provided by Stellar MLS
$1,600,000
325 Crystal Wood Dr
Winter Garden, FL 34787
5 bd · 5 ba · 4,442 sqft
Winter Grv
MLS ID #O6408089, WRA BUSINESS & REAL ESTATE.
Listing provided by Stellar MLS
$1,599,000
17372 Glossy Pomelo Way
Winter Garden, FL 34787
5 bd · 6 ba · 4,977 sqft
Lake Star/Ovation Ph 1b
MLS ID #O6406639, WRA BUSINESS & REAL ESTATE.
Listing provided by Stellar MLS
$1,550,000
7031 Billie Ct
Winter Garden, FL 34787
4 bd · 4 ba · 3,487 sqft
West Lake Hancock Estates
MLS ID #O6445243, CASTRO REALTY GROUP.
Listing provided by Stellar MLS
$1,550,000
16788 Muskgrass Dr
Winter Garden, FL 34787
4 bd · 5 ba · 4,733 sqft
Lake Star At Ovation Phase 1b
MLS ID #O6388174, MS LAND & BUILDING 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
$1,500,000
2010 Boss Hewett St
Winter Garden, FL 34787
5 bd · 4 ba · 3,781 sqft
Hull Island/Oakland Ph 2
MLS ID #O6423216, RE/MAX ASSURED.
Listing provided by Stellar MLS
$1,499,999
241 N Dillard St
Winter Garden, FL 34787
4 bd · 3 ba · 3,507 sqft
J L Dillard Sub 3
MLS ID #O6353975, HOMEVEST REALTY.
Listing provided by Stellar MLS
$1,499,990
2450 Dahlgren Way
Winter Garden, FL 34787
5 bd · 5 ba · 4,365 sqft
Bronsons Lndgs F & M
MLS ID #TB8481106, LPT REALTY, LLC.
Listing provided by Stellar MLS
$1,400,000
1112 Hull Island Dr
Oakland, FL 34787
4 bd · 4 ba · 3,562 sqft
Hull Island At Oakland
MLS ID #O6434371, HOMEVEST REALTY.
Listing provided by Stellar MLS
$1,399,999
1720 Lake Roberts Landing Dr
Winter Garden, FL 34787
5 bd · 5 ba · 4,919 sqft
Lake Roberts Lndg E
MLS ID #O6436608, ACCORD REAL ESTATE SERVICES.
Listing provided by Stellar MLS
$1,350,000
16730 Rusty Anchor Rd
Winter Garden, FL 34787
6 bd · 5 ba · 4,451 sqft
Waterside/Johns Lk-Ph 1
MLS ID #S5156404, TITAN REALTY GROUP LLC.
Listing provided by Stellar MLS
More Winter Garden Homes for Sale
All Winter Garden homes $500K and up, with the live market brief →
Winter Garden buyer questions
How many homes $1M–$2M are for sale in Winter Garden right now?+
As of October 2, 2026, 64 homes $1M–$2M are listed for sale in Winter Garden (ZIP 34787, which includes Horizon West and Oakland), priced from $1,000,000 to $1,999,000; the middle half are listed between $1,100,000 and $1,550,000. That count includes 62 single-family homes, 2 townhomes or villas; single-family homes alone have a median list price of $1,200,000. This updates automatically from the Stellar MLS.
What is the median list price for homes $1M–$2M in Winter Garden?+
The median list price is about $1,200,000, roughly $359 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 $1M–$2M in Winter Garden?+
26 (41%) of the active homes $1M–$2M in Winter Garden are listed below their original asking price, by a median of 8.4%, 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 $1M–$2M in Winter Garden been on the market?+
As of October 2, 2026, the homes $1M–$2M for sale in Winter Garden have been listed a median of 92 days, and 5 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 Garden are already under contract?+
18 homes $1M–$2M in Winter Garden show as pending or under contract as of October 2, 2026, alongside 64 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 4:21 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.