Winter Garden
Historic Charm Meets Modern Growth West of Orlando
Winter Garden, FL
A thriving city west of Orlando with a beloved historic downtown, Hamlin Town Center, and master-planned communities drawing families from across Central Florida.
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Ryan's Take on Winter Garden
Winter Garden splits into two distinct markets, and knowing which one a buyer wants is half the job. There's the Plant Street historic core — Craftsman bungalows under heritage oaks, the West Orange Trail running right through the downtown median, Crooked Can and Axum Coffee a walk from the front porch. Then there's Hamlin and the Horizon West villages like Waterleigh and Oakland Park, where the appeal is new construction, Lake Hancock's town center, and amenity density. They share a ZIP and almost nothing else.
What ties it together is West Orange High and the SR-429 run to Disney in about twenty minutes, which is why families from across the metro target this area specifically. Demand stays tight in the desirable tiers, and trail-adjacent homes near Plant Street carry a real premium because that half-mile is the most competitive stretch in West Orange County. Buyers weighing Winter Garden usually also look at Windermere for Butler Chain lakefront or Clermont for a lower entry point.
— Ryan Solberg, Broker/Owner, MaxLife Realty
Recent Sales Map
60 recent individual sales in and around Winter Garden · FL public records · no addresses published
Approximate sale locations — dots are offset ±1 home for privacy
| Beds | Baths | Sq Ft | Listed | Sold ▼ | List Price | Sold Price | $/Sq Ft | DOM |
|---|---|---|---|---|---|---|---|---|
| — | — | 5,390 | — | 12/1/25 | — | $2,340,000 | $434 | — |
| — | — | 4,679 | — | 12/1/25 | — | $2,300,000 | $492 | — |
| — | — | 4,092 | — | 12/1/25 | — | $2,165,000 | $529 | — |
| — | — | 3,524 | — | 12/1/25 | — | $1,950,000 | $553 | — |
| — | — | 2,790 | — | 12/1/25 | — | $1,400,100 | $502 | — |
| — | — | 3,623 | — | 12/1/25 | — | $1,330,000 | $367 | — |
| — | — | 4,293 | — | 12/1/25 | — | $1,140,000 | $266 | — |
| — | — | 3,113 | — | 12/1/25 | — | $1,125,000 | $361 | — |
| — | — | 3,104 | — | 12/1/25 | — | $1,095,000 | $353 | — |
| — | — | 3,616 | — | 12/1/25 | — | $1,070,000 | $296 | — |
| — | — | 3,881 | — | 12/1/25 | — | $1,070,000 | $276 | — |
| — | — | 4,857 | — | 12/1/25 | — | $1,025,000 | $211 | — |
| — | — | 3,248 | — | 12/1/25 | — | $960,000 | $296 | — |
| — | — | 2,325 | — | 12/1/25 | — | $929,500 | $400 | — |
| — | — | 3,101 | — | 12/1/25 | — | $900,000 | $290 | — |
| — | — | 2,061 | — | 12/1/25 | — | $888,000 | $431 | — |
| — | — | 3,145 | — | 12/1/25 | — | $865,000 | $275 | — |
| — | — | 2,700 | — | 12/1/25 | — | $860,000 | $319 | — |
| — | — | 2,935 | — | 12/1/25 | — | $850,000 | $290 | — |
| — | — | 2,992 | — | 12/1/25 | — | $845,000 | $282 | — |
| — | — | 3,598 | — | 12/1/25 | — | $835,000 | $232 | — |
| — | — | 3,599 | — | 12/1/25 | — | $820,000 | $228 | — |
| — | — | 3,742 | — | 12/1/25 | — | $811,000 | $217 | — |
| — | — | 2,499 | — | 12/1/25 | — | $810,000 | $324 | — |
| — | — | 2,683 | — | 12/1/25 | — | $809,100 | $302 | — |
| — | — | 2,750 | — | 12/1/25 | — | $800,000 | $291 | — |
| — | — | 3,316 | — | 12/1/25 | — | $800,000 | $241 | — |
| — | — | 3,367 | — | 12/1/25 | — | $799,000 | $237 | — |
| — | — | 3,097 | — | 12/1/25 | — | $780,000 | $252 | — |
| — | — | 2,637 | — | 12/1/25 | — | $775,000 | $294 | — |
| — | — | 3,668 | — | 12/1/25 | — | $775,000 | $211 | — |
| — | — | 3,074 | — | 12/1/25 | — | $775,000 | $252 | — |
| — | — | 3,140 | — | 12/1/25 | — | $775,000 | $247 | — |
| — | — | 3,472 | — | 12/1/25 | — | $760,000 | $219 | — |
| — | — | 4,258 | — | 12/1/25 | — | $755,000 | $177 | — |
| — | — | 4,686 | — | 12/1/25 | — | $755,000 | $161 | — |
| — | — | 4,247 | — | 12/1/25 | — | $750,000 | $177 | — |
| — | — | 3,157 | — | 12/1/25 | — | $749,000 | $237 | — |
| — | — | 3,074 | — | 12/1/25 | — | $740,000 | $241 | — |
| — | — | 3,316 | — | 12/1/25 | — | $740,000 | $223 | — |
| — | — | 3,493 | — | 12/1/25 | — | $737,500 | $211 | — |
| — | — | 3,517 | — | 12/1/25 | — | $730,000 | $208 | — |
| — | — | 2,347 | — | 12/1/25 | — | $720,000 | $307 | — |
| — | — | 3,690 | — | 12/1/25 | — | $715,000 | $194 | — |
| — | — | 3,046 | — | 12/1/25 | — | $710,000 | $233 | — |
| — | — | 2,970 | — | 12/1/25 | — | $705,000 | $237 | — |
| — | — | 2,889 | — | 12/1/25 | — | $700,000 | $242 | — |
| — | — | 2,840 | — | 12/1/25 | — | $689,000 | $243 | — |
| — | — | 2,617 | — | 12/1/25 | — | $685,000 | $262 | — |
| — | — | 3,336 | — | 12/1/25 | — | $665,000 | $199 | — |
| — | — | 2,903 | — | 12/1/25 | — | $660,000 | $227 | — |
| — | — | 2,191 | — | 12/1/25 | — | $649,000 | $296 | — |
| — | — | 2,889 | — | 12/1/25 | — | $645,000 | $223 | — |
| — | — | 2,117 | — | 12/1/25 | — | $645,000 | $305 | — |
| — | — | 2,010 | — | 12/1/25 | — | $638,000 | $317 | — |
| — | — | 1,844 | — | 12/1/25 | — | $615,000 | $334 | — |
| — | — | 2,409 | — | 12/1/25 | — | $606,000 | $252 | — |
| — | — | 2,218 | — | 12/1/25 | — | $600,000 | $271 | — |
| — | — | 2,508 | — | 12/1/25 | — | $585,200 | $233 | — |
| — | — | 2,614 | — | 12/1/25 | — | $580,000 | $222 | — |
Currently For Sale
0 active listings in Winter Garden
Winter Garden Market — Common Questions
Is Winter Garden a buyer's or seller's market in 2026?+
Recent public-record sales volume in Winter Garden is currently too low to call the market definitively. Contact Ryan Solberg at MaxLife Realty for a current read.
How many homes are for sale in Winter Garden?+
There are currently 0 active listings in Winter Garden.
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What Is Your Winter Garden Home Worth?
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Ryan Solberg
MaxLife Realty
321.373.3536
Report generated August 6, 2026 at 11:13 AM ET· Powered by Stellar MLS
MLS Data:Active and pending listing data is sourced from the Stellar MLS as distributed by MLS GRID. 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. The MLS GRID does not guarantee the accuracy of this data, which may not reflect all real estate activity in the area.
Sold Data: Sales analysis is derived from Florida Department of Revenue public property records(arm's-length transactions). Ryan Solberg and MaxLife Realty LLC are not affiliated with Winter Gardenor its HOA. This report is not intended to solicit properties already listed for sale nor to cause a breach of an existing agency relationship. Data should be independently verified. E&OE.
Based on information submitted to the MLS GRID as of August 6, 2026 at 11:13 AM 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.
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 August 6, 2026. 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