Oakshire Estates
Homes for Sale in Orlando, FL

All 4,060 homes for sale in Orlando, FL · median $384,945 · 150 homes for sale in 32824 · Orange County homes for sale

Community in Orlando · Orange County
112 homesBuilt 2001–2004
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True comps, carrying-cost math, and listings before the portals.

Built fromLive Stellar MLS dataFL DOR public recordsUpdated twice daily

Nearby homes for sale

No active listings inside Oakshire Estates Ph I right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.

949 WHISPERING CYPRESS LANE
$360K · 0.2 mi away
3 bd · 2 ba · 1,718 sqft
949 WHISPERING CYPRESS LANE
Listed by EXP REALTY LLC
14424 BABYLON WAY
$579K · 0.2 mi away
4 bd · 2 ba · 2,657 sqft
14424 BABYLON WAY
Listed by MILLENIUM REALTY GROUP
14001 FAIRWINDS COURT
$385K · 0.2 mi away
3 bd · 2 ba · 1,700 sqft
14001 FAIRWINDS COURT
Listed by COMPASS FLORIDA LLC
147 CORALWOOD CIRCLE
$352K · 0.5 mi away
4 bd · 2.5 ba · 2,324 sqft
147 CORALWOOD CIRCLE
Listed by OPENDOOR BROKERAGE LLC
13923 CORRINE KEY PLACE
$260K · 0.5 mi away
3 bd · 2 ba · 1,246 sqft
13923 CORRINE KEY PLACE
Listed by RICHARD REALTY MGMT GROUP LLC
930 WINDROSE DRIVE #2
$390K · 0.5 mi away
4 bd · 3 ba · 1,982 sqft
930 WINDROSE DRIVE #2
Listed by VENCORP RE, LLC

Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.

Oakshire Estates Ph I is a community in Orlando, Orange County, FL. Across Orlando as a whole, 5,915 homes closed in the last 12 months at a median of $412,500, 41 median days on market, with 1,608 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $6,880 ($6,210 with the full homestead exemption).

Live · Oakshire Estates Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Ownership and context
70%
Owner-occupied · Oakshire Estates
78 of 112 parcels homesteaded (FL DOR 2025)
30%
Non-owner-occupied · Oakshire Estates
incl. 4% trust or LLC-held · 100% out-of-state
112
Homes in the community
112 residential parcels (FL DOR 2025)
Track record · years of records
Est. 2001
Community established
homes built 2001-2004, median 2002 (FL DOR 2025)
1
Failed listings · 2026
peaked at 11 in 2008

The market around Oakshire Estates

Oakshire Estates is a small community — 24 recorded sales on file, most recently in 2026 — too few for its own price trend. Here is the market around it.

Across Orange County, 5,886 homes are active and 2,019 pending (26% under contract).

Homes here are single family residence.

ZIP and county figures describe the wider market, not Oakshire Estates specifically. Momentum Research analysis of MLS records.

If we were buying in Oakshire Estates today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 closer look at the Oakshire Estates market

The housing stock is 112 homes built between 2001 and 2004, and 70% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.

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.

Jon Brooks · Founder, Momentum Realty

HOA, CDD & Fees

In short
  • HOA status not on record. Verify any dues before you offer
  • Any club/amenity membership is billed separately

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.

The takeaway

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.

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 →

Real comps, not an automated estimate.

Frequently Asked Questions

How many homes are in Oakshire Estates?
The Florida DOR 2025 assessment roll shows 112 homes in Oakshire Estates (public records).
What share of Oakshire Estates is owner-occupied?
70% of Oakshire Estates parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Oakshire Estates built?
Homes in Oakshire Estates were built between 2001 and 2004, with a median year built of 2002.0 (FL DOR 2025 roll).
Who is the best real estate agent for Oakshire Estates?
The best agent for Oakshire Estates is one who actively works Orlando and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Oakshire Estates.
How do I find a top Orlando real estate agent who knows Oakshire Estates?
Share a few details in the form on this page. Momentum Realty has 320+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Oakshire Estates and the wider Orlando area.
Can Momentum Realty connect me with an agent for Oakshire Estates?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Oakshire Estates purchase or sale - no call center and no pressure.

Data sources & freshness

Housing stock & ownershipFlorida DOR assessment roll (street-list match (4 streets, ZIP 32824))
Under-contract sharesStellar MLS records, as of 2026-07-12

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.

Own a home here?

You just read the data. Now see what your home is worth.

The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live your area comps.

Looking to buy here? Search homes for sale →

What’s your home worth in your area?

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More Orlando & Orlando & Orange County guides

Compare before you commit - every guide covers pricing, HOA/CDD, insurance posture, and fit. Browse all of Orlando & Orange County or the full Neighborhood Finder.

Nearby Communities

Explore more neighborhoods near Oakshire Estates with Momentum Realty’s local guides.

Oakshire Estates0.1 mi away · 1 for saleWPWillow Pond0.2 mi away · median $399K, 3 sales/12 moPCPebble Creek0.4 mi away · 3 for sale

Browse all neighborhood guides →

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