Oakglen Estates
Homes for Sale in Winter Garden, FL
All 749 homes for sale in Winter Garden, FL · median $589,900 · 706 homes for sale in 34787 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
As of October 2026, Oakglen Estates in Winter Garden, FL has 1 home for sale. As of October 2026, the MLS records 22 closed sales in Oakglen Estates in Winter Garden, FL since 2005, the most recent in August 2025. Across Winter Garden as a whole, 1,339 homes closed in the last 12 months at a median of $595,000, 38 median days on market, with 694 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $9,920 ($9,250 with the full homestead exemption).
Oakglen Estates is a compact, built-out pocket in Winter Garden, with just 62 homes that all went up in a tight window between 2005 and 2007. That uniformity matters: when the housing stock is this consistent in age and layout, price is driven less by square footage on paper and more by condition and updates. A home carrying its original 2005 finishes will trade very differently from one that has been renovated, even at the same footprint around the 2,337-square-foot median.
This is a small market, so read it carefully. With few homes and a limited closings window, a single sale can distort the picture, and inventory can be thin. For sellers, that scarcity can work in your favor when a well-kept home hits the market. For buyers, patience matters — you may wait for the right listing rather than choose among several. The high homestead share, roughly three in four homes, suggests an owner-occupied community that turns over slowly.
Figures in this note are as of July 13, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Oakglen Estates right now
🟢 Buyer-leaning market. 12.0 months of supply and 0% of the inventory already under contract give buyers above-average negotiating leverage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of September 20, 2026. Confidence: Low (1 active and pending listings, 0 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 24, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Oakglen Estates is a mid-2000s enclave of 62 homes in Winter Garden's Orange County footprint, where the roughly 2,337-square-foot median home and consistent build era make condition the real differentiator between one listing and the next.
Stellar MLS sales records identify 43 homes in Oakglen Estates that have changed hands since 2006, built between 2005 and 2007 (median 2006), with a median living area of about 2,337 sq ft and a typical 4-bedroom, 3-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
County records show 5 qualified sales in Oakglen Estates across 2024–2025 (2 in 2024, 3 in 2025), median $515,300 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Oakglen Estates is best for.
Best for
- Buyers seeking a settled, built-out community and comfortable waiting for the right listing
- Those with a renovation budget who can capture value in a home carrying original finishes
- Long-hold buyers who value a stable, owner-occupied street over quick turnover
Probably not for
- Buyers who need several homes to compare and want to close quickly
- Anyone set on new construction or contemporary open-plan layouts
- Buyers with no budget for the roof, HVAC, or other aging-system replacements a two-decade-old home may need
The market around Oakglen Estates
Oakglen Estates is too small for its own price trend, so here is the market around it.
In ZIP 34787, 932 homes are on the market and 29% are under contract — a steady corner of Winter Garden.
Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).
In ZIP 34787 (Winter Garden), 2,123 homes closed in the last 12 months at a median of $595K ($252/sq ft), down 0.9% year over year, with a median 37 days on market. Right now 352 active and 181 pending listings put supply at about 3.7 months — a balanced market. See the live ZIP 34787 housing market and the Orange County market.
ZIP and county figures describe the wider market, not Oakglen Estates specifically. Momentum Research analysis of MLS records.
Homes For Sale Right Now in Oakglen Estates
Live MLS inventory for Oakglen Estates. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Oakglen Estates listings as of 2026-10-19, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2025. Tap any home to ask about it.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Dillard Street Elem · Elementary
- Lakeview Middle · Middle
- Ocoee High · High
Zoned schools reflect the assignments reported on recent Oakglen Estates listings and can change; always confirm with Orange County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Oakglen Estates address.
Shop the zone: Homes zoned for Ocoee High High School
The Oakglen Estates buying strategy.
If we were buying in Oakglen Estates today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Oakglen Estates.
A built-out mid-2000s enclave
Everything here was built within a three-year span, so you are looking at a single architectural generation rather than a mix of eras. Homes now roughly two decades old are at the age where major systems — roofs, HVAC, water heaters — either have been replaced already or are due. That is the first thing to check on any Oakglen listing, and it is where value gaps open up between otherwise similar homes.
With about three-quarters of homes homesteaded, this reads as a stable, owner-occupied community that does not churn quickly. That stability tends to keep the stock maintained, but it also means listings are limited. Expect to evaluate homes one at a time as they come available rather than comparing a deep bench of options.
The location and the amenities are priced into every listing in Oakglen Estates. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a 62-home community with limited turnover, the difference between a fair price and an overpay comes down to condition and updates, not headline square footage. We track what actually closes here, help you weight the cost of pending system replacements against a home's asking price, and tell you plainly when a listing is priced for its finishes rather than its bones.
Oakglen Estates in 15 seconds.
Email me new listings in Oakglen Estates
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Oakglen Estates
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Oakglen Estates will answer, and the answer is published on this page for the next buyer.
HOA, CDD & Fees
- HOA dues reported around $64/month (about $768/yr) · median of 34 MLS listings, most billed twice a year
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $64 per month ($768 a year) — the median AssociationFee across 34 MLS records, normalised to a monthly figure; most are billed twice a year. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-10.
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Oakglen Estates buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Oakglen Estates sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Oakglen Estates, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Oakglen Estates home worth?
Get a no-obligation home value based on real comparable sales in Oakglen Estates, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Winter Garden →
Last 30 days in Oakglen Estates: 1 closed sale (median $615,000). As of October 24, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
| Location | Winter Garden, Orange County, FL · ZIP 34787 |
|---|---|
| Homes in the community | 62 (FL DOR 2025 assessment roll) |
| Years built | 2005–2007 (median 2005) |
| Typical living area | 2,337 sq ft (median) |
| For sale right now | 1 active, 0 pending · median asking $649,000 · 12.0 months of supply |
| Owner-occupied (homestead) share | 74% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2025; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Oakglen Estates key facts,” movewithmomentum.com/neighborhoods/oakglen-estates, data as of September 20, 2026.
Housing distress & ownership in Oakglen Estates, Winter Garden
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period October 2026 through October 2026. Deemed reliable but not guaranteed.
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Winter Garden guides & data
- Market data
- Cost of living
- Best neighborhoods
- Flood zones
- Property taxes (Orange County)
- Homestead exemption (Orange County)
- Home insurance cost
- New construction
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
Real estate agent in Winter Garden? Join Momentum in Winter Garden: 100% commission, one $12K cap.
Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Hearthglen Boulevard (20 homes on record)
- Hearthglen Boulevard (11 homes on record)
30% of homes for sale in ZIP 34787 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-13).
Recent Developments in Oakglen Estates
Development, infrastructure, retail, and school activity affecting Oakglen Estates, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- September 2026Development
Orange County commissioners approve Tuscana land use plan in Shingle Creek Basin on 4-3 vote
Commissioners voted 4-3 to approve the Tuscana land use application from Shingle Creek Co-Owners LLC and Geyer Development, reversing a unanimous rejection in May 2025. The plan includes more than 1,000 hotel rooms, about 4,000 apartments and commercial buildings, with conditions for a raised road, flood mitigation and wetland protection. The developer projects thousands of jobs at full build-out.
What it may mean for the marketThe approval could add substantial rental housing, hotel capacity and commercial space in the Shingle Creek area, while flood-mitigation conditions will shape how and when it is built. The site is about 6 miles northeast of Oakglen Estates.
Source: Spectrum News 13 - September 2026Development
Lake County approves 2,241-acre Panther Run rezoning for up to 2,624 homes near Clermont
The Lake County Commission voted 3-1 on Sept. 1 to rezone about 2,241 acres in the Wellness Way area, north of Sawgrass Bay Boulevard, for GT Homes. The planned unit development allows up to 2,624 residential units and more than 1 million square feet of non-residential space, with sites reserved for a future public high school and public safety facilities. Plans include extending County Road 455 and about 11 miles of public trails.
What it may mean for the marketThe plan adds long-term housing supply, employment space and new connector roads in south Lake County, with infrastructure planned ahead of residential growth. The site is about 10 miles northwest of Oakglen Estates.
Source: Clermont Sun - August 2026Retail & Dining
Plans for Mattel indoor water park near Lake Buena Vista Factory Stores expand to 13 acres
Updated plans for the site off State Road 535 show a 95,000-square-foot indoor water park designed by Martin Aquatic, a separate 45,000-square-foot entertainment building and nearly 900 parking spaces. The tower height rises to as much as 100 feet and still needs Orange County approval. About 200 jobs are expected, and no opening date has been announced.
What it may mean for the marketThe project would add visitor attractions, dining and roughly 200 jobs near the State Road 535 corridor, with added traffic and parking demand nearby. The site is about 4 miles northeast of Oakglen Estates.
Source: FOX 35 Orlando - July 2026Development
Capstone begins construction on The Gateway luxury apartments
Capstone Building Corp began construction on The Gateway, a 270-unit apartment community at 7250 Shadowridge Drive in Orlando, developed by JBL Development. The five-story gated project spans more than 417,000 square feet and is expected to be completed in late 2027. Amenities include a saltwater pool, fitness center, pickleball court, and a clubhouse with a restaurant and bar.
What it may mean for the marketAdds 270 market rate apartments in a five story building with resort style amenities, expanding the local rental housing stock in the Airport Lakes area of south Orlando. The project is about 15 miles northeast of Oakglen Estates, elsewhere in Orange County.
Source: Construction Owners - July 2026Development
Orange County opens Enclave at Canopy Park with 104 affordable units
Orange County opened The Enclave at Canopy Park, a 104-unit affordable apartment community at 4440 Canopy Park Loop developed by Archway Partners. The county contributed 3 million dollars from its Affordable Housing Trust Fund. The community includes one and two bedroom homes plus a community center, fitness center, technology lab, and EV charging.
What it may mean for the marketAdds 104 income-restricted apartment homes to the local rental supply along with new community amenities and green-certified construction. The project is about 13 miles northeast of Oakglen Estates, elsewhere in Orange County.
Source: ClickOrlando - July 2026Civic
Orange County previews new Innovation Center on West Colonial Drive
Orange County previewed its new Innovation Center at 7149 West Colonial Drive, located within the county's Multicultural Center and Senior Center complex, with an official opening set for Fall 2026. The center will offer technology programs including 3D printing and makerspace prototyping through the Orange County Library System, plus career exploration and workforce training through CareerSource Central Florida.
What it may mean for the marketAdds a county operated civic and technology facility with library and workforce programming to the West Colonial corridor. The project is about 16 miles north of Oakglen Estates, elsewhere in Orange County.
Source: Orange County Newsroom
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
Frequently Asked Questions
Is Oakglen Estates a buyer's or seller's market right now?
How many homes are in Oakglen Estates?
What share of Oakglen Estates is owner-occupied?
When were the homes in Oakglen Estates built?
Who is the best real estate agent for Oakglen Estates?
How do I find a top Winter Garden real estate agent who knows Oakglen Estates?
Can Momentum Realty connect me with an agent for Oakglen Estates?
Where is Oakglen Estates, and what county is it in?
Should you buy in Oakglen Estates?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 19, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 34787)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2005 (22 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
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