Oakshire Estates
Homes for Sale in Orlando, FL
True comps, carrying-cost math, and listings before the portals.
Oakshire Estates is a tight, single-phase build — all 124 homes went up between 2001 and 2004, with a median build year of 2002. That kind of construction window means consistent lot sizes, similar rooflines, and comparable systems age across the community, which simplifies comparisons for anyone evaluating a home here against another.
Right now there are zero active listings and the most recent closings window covers just one month, so there is very little live inventory or fresh transaction data to read from. That is not unusual for a small, established community — it just means a buyer who wants in should be ready to move when something does list, and a seller has almost no active competition to price against.
Figures in this note are as of July 20, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Oakshire Estates right now
🟡 Balanced market. 6.0 months of supply and 0% of the inventory already under contract put buyers and sellers on roughly even footing.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 September 20, 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
Oakshire Estates is a gated community of 124 homes built in a tight window between 2001 and 2004, with a median living area of 2,145 square feet and a homestead share of roughly 67% — a strong signal that most owners here live in the home rather than hold it as a rental or second property.
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.
The setting & the homes.
Aerial and on-site photos of Oakshire Estates. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Oakshire Estates
Oakshire Estates
Oakshire Estates
Oakshire EstatesPhotos from Stellar MLS listings in Oakshire Estates; content deemed reliable but not guaranteed.
Who Oakshire Estates is best for.
Best for
- Buyers who want a gated, single-phase community with homes of consistent age and size
- Buyers planning to occupy the home long-term in a community where most owners are homesteaded
- Buyers comfortable waiting for the right listing given the current lack of active inventory
Probably not for
- Buyers who need to choose from multiple active listings right away
- Buyers looking for a resort-style amenity package beyond a gated entry and playground
- Investors seeking a community with a high rate of non-owner-occupied turnover
The market around Oakshire Estates
Oakshire Estates is too small for its own price trend, so here is the market around it.
In ZIP 32824, 243 homes are on the market and 21% are under contract — a steady corner of Orlando.
Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).
ZIP and county figures describe the wider market, not Oakshire Estates specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in Oakshire Estates, ORLANDO
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.
Homes For Sale Right Now in Oakshire Estates
Live MLS inventory for Oakshire 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 Oakshire Estates listings as of 2026-10-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2007 through 2025. Tap any home to ask about it.
Oakshire Estates on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap contributors.
Life at Oakshire Estates
- Gated · reported on 1 of 1 listings
- Playground · reported on 1 of 1 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Oakshire Elem · Elementary
- Meadow Wood Middle · Middle
- Cypress Creek High · High
Zoned schools reflect the assignments reported on recent Oakshire 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 Oakshire Estates address.
Recent Developments in Oakshire Estates
Development, infrastructure, retail, and school activity affecting Oakshire 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 west of Oakshire Estates.
Source: Spectrum News 13 - September 2026Infrastructure
CFX holds public meetings on 14-mile toll road through part of Split Oak Forest
The Central Florida Expressway Authority held public meetings on Sept. 16 and 17 for a 14-mile road from State Road 417 near Boggy Creek Road in Orange County to Nova Road in Osceola County. CFX says portions could begin construction next year and that the road would ease traffic on Narcoossee Road. The agency faces a legal challenge from Orange County and is pursuing an eminent domain case.
What it may mean for the marketIf built, the road would add a new east-west route between Lake Nona and St. Cloud, changing commute options and access to east Orange and Osceola land. The site is about 11 miles east of Oakshire Estates.
Source: Spectrum News 13 - 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 9 miles west of Oakshire 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 6 miles northeast of Oakshire 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 9 miles north of Oakshire Estates, elsewhere in Orange County.
Source: ClickOrlando - March 2026Development
Orlando approves the 380-acre Dowden Central Community Development District in Lake Nona
Orlando approved the Dowden Central Community Development District, a roughly 380-acre district in the Lake Nona area of southeast Orlando, in March 2026. The district provides the framework to build roads, drainage, utilities, and parks for future development phases.
What it may mean for the marketA new community development district lays the groundwork for large-scale growth in the Lake Nona area, a step that typically precedes new housing and commercial activity nearby. The site is about 6 miles east of Oakshire Estates.
Source: ClickOrlando
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 the Orlando Metro.
The Oakshire Estates buying strategy.
If we were buying in Oakshire 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.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
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 Oakshire Estates.
A single-era build behind the gate
Because every home in Oakshire Estates was built within a three-year span, the community reads as one cohesive product rather than a patchwork of eras and builders. The median living size of 2,145 square feet puts most homes in a mid-size single-family range — enough room to differentiate on floor plan and lot without the wide size swings you see in communities built over a decade or more.
The gated entry and playground are the amenities reported across MLS listings for this community; they point to a self-contained layout rather than a resort-style amenity package. With a homestead share near 67%, this reads as a community where ownership skews toward long-term occupancy rather than turnover-driven investment activity, which tends to support a steadier day-to-day feel to the streets and common areas.
The location and the amenities are priced into every listing in Oakshire Estates. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
With zero active listings and a single month of closing data to work from, reading this market takes more than a portal search — it takes someone tracking the MLS feed closely enough to catch a listing the moment it surfaces and to put the build-year, size, and homestead data in context before you make an offer.
Oakshire Estates in 15 seconds.
Tools for a Oakshire 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 Oakshire Estates sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Oakshire 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 Oakshire Estates home worth?
Get a no-obligation home value based on real comparable sales in Oakshire 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 homes for sale in Oakshire Estates on the map →
Frequently Asked Questions
Is Oakshire Estates a buyer's or seller's market right now?
How many homes are in Oakshire Estates?
What share of Oakshire Estates is owner-occupied?
When were the homes in Oakshire Estates built?
Who is the best real estate agent for Oakshire Estates?
How do I find a top Orlando real estate agent who knows Oakshire Estates?
Can Momentum Realty connect me with an agent for Oakshire Estates?
Should you buy in Oakshire Estates?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near Oakshire Estates with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 23, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (5 streets, ZIP 32824)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2007 (31 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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See how Oakshire Estates fits the bigger picture — live prices, inventory, and Momentum Scores: