Courtlea Oaks
Homes for Sale in Winter Garden, FL
True comps, carrying-cost math, and listings before the portals.
The 60-Second Overview
Courtlea Oaks market snapshot (as of July 13, 2026): the median sale price is about $1.16M ($302 per sq ft over the trailing 12 months of closed sales), and a median 24 days on market for closed sales.
Courtlea Oaks is a community of 36 homes in Winter Garden, Orange County, built between 1996 and 2007 (median 2000.0), with a median living area of about 2,980 square feet. 92% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending July 13 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($1.16M) IS the median in the snapshot above.
Windows contain 0 to 3 sales each (3 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period %s through %s. Deemed reliable but not guaranteed.
The Courtlea Oaks buying strategy.
If we were buying in Courtlea Oaks 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 Courtlea Oaks.
A closer look at the Courtlea Oaks market
At a median of $302 per square foot, Courtlea Oaks prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
The housing stock is 36 homes built between 1996 and 2007, and 92% 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 Courtlea Oaks. The deal is won or lost on condition, the comps, and the renovation math.
HOA, CDD & Fees
- Mandatory HOA — confirm current dues
- 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.
Tools for a Courtlea Oaks 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 Courtlea Oaks sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Courtlea Oaks, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Courtlea Oaks home worth?
Get a no-obligation home value based on real comparable sales in Courtlea Oaks, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Frequently Asked Questions
What is the median home price in Courtlea Oaks?
How long do homes in Courtlea Oaks take to sell?
How many homes are in Courtlea Oaks?
What share of Courtlea Oaks is owner-occupied?
When were the homes in Courtlea Oaks built?
Do cash buyers compete in Courtlea Oaks?
Who is the best real estate agent for Courtlea Oaks?
How do I find a top Winter Garden real estate agent who knows Courtlea Oaks?
Can Momentum Realty connect me with an agent for Courtlea Oaks?
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending July 13, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (2 streets, ZIP 34787)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2008 (6 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.
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.
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See how Courtlea Oaks fits the bigger picture — live prices, inventory, and Momentum Scores:
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