MLS data updated Oct 14, 2026
Oakland TrlsReal Estate Market Report · October 2026
Oakland Trls real estate market report · Winter Garden, FL
Winter Garden, FL
Oakland Trls is a residential community in Winter Garden, Florida. This live report tracks active and pending listings, 12-month sale prices and days on market, and public-record sales for the surrounding ZIP.
Median sold: $537K · Median days on market: 112 · Sold-to-list: 97.2% · Source: Stellar MLS, last 12 mo
About 6.7 months of inventory — supply is outpacing demand, so buyers have room to negotiate (over 6 months = buyer's market).
Aggregate statistics from Stellar MLS closed sales over the last 12 months and live MLS inventory. A market read, not an appraisal of any home or a listing of individual sales.
Want this as a printable report?
Generate a clean, branded multi-page PDF of the Oakland Trls market — perfect to print or email.
Under Contract
1 home pending in Oakland Trls · Avg. $515K
Oakland Trls · 4th Quarter 2026
9 sales · Stellar MLS · last 12 mo
$537K
Median Sale Price
112 days
Median Days on Market
97.2%
Sold-to-List
$223
Median $/sqft
Recent Sales Map
60 recent individual sales in and around Oakland Trls · 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 | — |
| — | — | 3,668 | — | 12/1/25 | — | $775,000 | $211 | — |
| — | — | 3,074 | — | 12/1/25 | — | $775,000 | $252 | — |
| — | — | 2,637 | — | 12/1/25 | — | $775,000 | $294 | — |
| — | — | 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
5 active listings in Oakland Trls
$219/sqft
View details
$230/sqft
View details
$237/sqft
View details
$226/sqft
View details
$196/sqft
View details
| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM |
|---|---|---|---|---|---|
| 4 | 3 | 2,576 | $565,000 | $219 | 17 |
| 3 | 3 | 2,082 | $479,900 | $230 | 36 |
| 3 | 3 | 2,152 | $510,000 | $237 | 139 |
| 5 | 3 | 3,528 | $796,000 | $226 | 337 |
| 4 | 3 | 2,854 | $559,000 | $196 | 48 |
Oakland Trls Market — Common Questions
Is Oakland Trls a buyer's or seller's market in 2026?+
Oakland Trls is currently a buyer's market with about 6.7 months of inventory. About 6.7 months of inventory — supply is outpacing demand, so buyers have room to negotiate (over 6 months = buyer's market).
What is the median home sale price in Oakland Trls?+
Based on Stellar MLS closed sales over the last 12 months, the median sale price in Oakland Trls is approximately $537K.
How many homes are for sale in Oakland Trls?+
There are currently 5 active listings in Oakland Trls, with homes selling at roughly 0.8 per month. That works out to about 6.7 months of inventory.
Free · No Obligation
What Is Your Oakland Trls Home Worth?
I analyze active competition, recent sales, and neighborhood trends to give you a precise estimate of what your home is worth right now — no automated Zestimate, a real analysis from a local expert.
Ryan Solberg
MaxLife Realty
321.373.3536
5.0 ★ · 42 reviews
What clients say
All 42 reviews on Zillow“Ryan was very helpful and quick to answer any questions I had. I was on a deadline to be out of my house and he made it happen — and in the end my family and I have a beautiful house.”
“Highly likely to recommend! Ryan helped us sell my mother's condo when she needed to move to assisted living. But that was just the start — he helped us find repairmen for the things that needed fixing.”
More communities in Winter Garden
- Overlook 2/Hamlin18 sales in 12 mo
- Johns Lake Pointe17 sales in 12 mo
- Highlands/Summerlake Groves16 sales in 12 mo
- Parkview/Hamlin15 sales in 12 mo
- Winter Grove13 sales in 12 mo
- Wintermere Pointe13 sales in 12 mo
- Covington Chase12 sales in 12 mo
- Hawksmoor12 sales in 12 mo
- Orchard Park/Stillwater Crossing12 sales in 12 mo
- Waterside/Johns Lake12 sales in 12 mo
- Southern Pines11 sales in 12 mo
- Northlake/Ovation10 sales in 12 mo
Report generated October 15, 2026 at 12:26 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 Oakland Trlsor 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 October 14, 2026 at 10:52 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.
Moving to Oakland Trls
Utilities & Services
Oakland Trls is in Orange County, Florida. Here's who to call to get power, water, and trash service set up in your name before closing.
Electric
Orlando Utilities Commission (OUC) · (407) 423-9018City of Orlando and parts of unincorporated Orange County. OUC also provides water in its territory.
Duke Energy Florida · (800) 700-8744Most of unincorporated Orange County, plus Winter Garden, Apopka, and Ocoee.
Water & Sewer
Orange County Utilities · (407) 836-5515Unincorporated Orange County (water & sewer).
OUC — Water (City of Orlando) · (407) 423-9018City of Orlando — OUC provides both water and electric.
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 14, 2026 at 10:52 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.
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