29
$235,000
2 bd · 2 ba · 1,144 sqft
1229 Winter Green Way, Winter Garden, FL
Nancy Postorino · REDFIN CORPORATION
Homes Under $1M in Winter Garden, FL
Hide MapHomes Under $1M in Winter Garden, FL
24 of 653 Listings
29$235,000
2 bd · 2 ba · 1,144 sqft
1229 Winter Green Way, Winter Garden, FL
Nancy Postorino · REDFIN CORPORATION
New88$679,000
5 bd · 3 ba · 3,021 sqft
922 Marsh Reed Dr, Winter Garden, FL
Kyle Madorin PA · UPWELL REALTY LLC
26$604,990
3 bd · 2 ba · 1,772 sqft
5960 Flowering Cherry Bnd, Winter Garden, FL
Ken Pozek · REAL BROKER, LLC
8$93,000
3 bd · — ba · — sqft
14395 Salamanca Drive, Winter Garden, FL
28$210,000
2 bd · 2 ba · 930 sqft
421 Eron Way #36, Winter Garden, FL
Erica Diaz · HOMEVEST REALTY
Open house Sun, Nov 15 · 1:00 PM34$715,000
4 bd · 3 ba · 3,074 sqft
8199 Gray Kingbird Dr, Winter Garden, FL
Jennifer King · CORCORAN PREMIER REALTY
Open house Sun, Nov 15 · 11:00 AM40$675,000
4 bd · 3 ba · 2,834 sqft
580 First Cape Coral Dr, Winter Garden, FL
Michelle Brierley · COLDWELL BANKER REALTY
38$650,000
3 bd · 3 ba · 2,613 sqft
15625 Murcott Harvest Loop, Winter Garden, FL
Margo Rochelle · WEICHERT REALTORS HALLMARK PROPERTIES
31$378,000
3 bd · 3 ba · 1,568 sqft
9991 Schroeder Alley, Winter Garden, FL
Melissa Burke-Cabral · MARK SPAIN REAL ESTATE
42$649,900
5 bd · 4 ba · 3,391 sqft
13728 Fox Glove St, Winter Garden, FL
Crystal Duckworth · CRYSTAL CLEAR REALTY LLC
51$550,000
4 bd · 2 ba · 2,487 sqft
906 Woodson Hammock Cir, Winter Garden, FL
John Muccigrosso, PA · RE/MAX 200 REALTY
51$774,900
4 bd · 4 ba · 2,935 sqft
9953 Summerlake Groves St, Winter Garden, FL
David Berlant · KELLER WILLIAMS REALTY AT THE PARKS
52$655,000
4 bd · 3 ba · 2,580 sqft
17385 Bal Harbour Dr, Winter Garden, FL
Huizi Li · MULTI CHOICE REALTY LLC
37$640,000
4 bd · 3 ba · 2,642 sqft
2004 Lake Roberts Landing Dr, Winter Garden, FL
Fernanda Negromonte · NOVA REAL ESTATE SERVICES INC
15$130,000
2 bd · 1 ba · 660 sqft
386 Railroad Ave, Winter Garden, FL
Bill Jefferson · ORANGE REALTY MASTERS
Open house Sat, Nov 21 · 11:00 AM21$600,000
4 bd · 3 ba · 2,569 sqft
14517 Black Lake Preserve St, Winter Garden, FL
Lyna Ramirez De Mayorga · BHHS FLORIDA REALTY
Open house Sun, Nov 15 · 1:00 PM34$829,496
4 bd · 3 ba · 3,038 sqft
6099 Flowering Cherry Bnd, Winter Garden, FL
Nancy Pruitt, PA · OLYMPUS EXECUTIVE REALTY INC
3$859,990
4 bd · 3 ba · 2,754 sqft
17443 Water Hemlock Rd, Winter Garden, FL
Stacie Brown Kelly · KELLER WILLIAMS ADVANTAGE REALTY
48$730,000
3 bd · 3 ba · 2,614 sqft
15628 Gentle Rain Dr, Winter Garden, FL
Caroline De Castro Marcellini · COMPASS FLORIDA, LLC
3$869,990
4 bd · 4 ba · 2,908 sqft
17437 Water Hemlock Rd, Winter Garden, FL
Stacie Brown Kelly · KELLER WILLIAMS ADVANTAGE REALTY
48$389,900
3 bd · 3 ba · 1,748 sqft
14838 Driftwater Dr, Winter Garden, FL
Ronda Christiansen · KELLER WILLIAMS ADVANTAGE REALTY
99$975,000
5 bd · 5 ba · 3,602 sqft
9228 Bradleigh Dr, Winter Garden, FL
Autumn Makin · LAKEFIELD REALTY GROUP LLC
Open house Sun, Nov 15 · 1:00 PM25$599,000
4 bd · 3 ba · 2,703 sqft
5531 Myrtle Pine Ln, Winter Garden, FL
Emily McCarthy · LOKATION
53$860,000
4 bd · 4 ba · 3,087 sqft
9218 Holliston Creek Pl, Winter Garden, FL
Gustavo Furtado · WRA BUSINESS & REAL ESTATE
Homes Under $1M in Winter Garden, FL: 653 active listings as of .
| Property type | Listings | Share |
|---|---|---|
| Single Family Residence | 382 | 58.5% |
| Condominium | 129 | 19.8% |
| Townhouse | 100 | 15.3% |
| Manufactured Home | 29 | 4.4% |
Stellar MLSOctober 2026 · This period is still settling
Selling at 98.5% of asking price
Buyers here are paying below asking. MLS · 184 sales · as of Oct 31, 2026
Source: HJN community data
