WINTER OAKS
Homes for Sale in WINTER GARDEN, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
WINTER OAKS right now
🟢 Still climbing. The trailing-12-month median ($715K) is up 39.7% from the prior 12 months ($512K). With about 3 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: Low (3 and 7 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated August 2, 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
WINTER OAKS market snapshot (as of August 2, 2026): the median sale price is about $715K ($240 per sq ft over the trailing 12 months of closed sales), and a median 42 days on market for closed sales. The trailing-12-month median is up 40% from the prior 12 months, computed from record-level Stellar MLS closed sales (3 closings in the current window).
WINTER OAKS is a community of 106 homes in WINTER GARDEN, Orange County, built between 2003 and 2007 (median 2004), with a median living area of about 2,178 square feet. 85% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of WINTER OAKS. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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WINTER OAKSPrice History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($715K) IS the median in the snapshot above, and the move from 2025 ($512K) IS the +39.7% one-year change.
Windows contain 0 to 7 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 2006 through 2026. Deemed reliable but not guaranteed.
WINTER OAKS Market Scorecard
WINTER OAKS is currently a balanced market. About 4.0 months of supply, a median asking price of $594,000, and homes go under contract in about 20 days.
Go deeper: county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in WINTER OAKS, 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 August 2026 through August 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in WINTER OAKS
Live MLS inventory for WINTER OAKS. 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 WINTER OAKS listings as of 2026-08-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2026. Tap any home to ask about it.
WINTER OAKS 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, tiles © CARTO.
Life at WINTER OAKS
- Playground · reported on 4 of 4 listings
- Pool · reported on 4 of 4 listings
- Community Mailbox · reported on 4 of 4 listings
- Deed Restrictions · reported on 4 of 4 listings
- Golf Carts OK · reported on 3 of 4 listings
- Park · reported on 2 of 4 listings
- Association Recreation - Owned · reported on 2 of 4 listings
- Fence Restrictions · reported on 1 of 4 listings
- Maintenance · reported on 1 of 4 listings
- Secured Garage/Parking · reported on 1 of 4 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
- Tildenville Elem · Elementary
- Lakeview Middle · Middle
- West Orange High · High
Zoned schools reflect the assignments reported on recent WINTER OAKS 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 WINTER OAKS address.
The WINTER OAKS buying strategy.
If we were buying in WINTER 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 WINTER OAKS.
A closer look at the WINTER OAKS market
At a median of $240 per square foot, WINTER 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 trailing-12-month median up 40% year over year. Homes that do trade take a median 42 days on market, useful leverage on any listing that has lingered.
The housing stock is 106 homes built between 2003 and 2007, and 85% 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 WINTER OAKS. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in WINTER OAKS buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (8.6). Basis: Recent Direction +39.7% year-over-year; Owner Commitment 85% owner-occupied; Pricing Power 96.1% sale-to-list. Refreshed with each data update.
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 WINTER 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 WINTER OAKS sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in WINTER 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 WINTER OAKS home worth?
Get a no-obligation home value based on real comparable sales in WINTER 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.
See homes for sale in WINTER OAKS on the map →
Frequently Asked Questions
What is the median home price in WINTER OAKS?
How long do homes in WINTER OAKS take to sell?
How many homes are in WINTER OAKS?
What share of WINTER OAKS is owner-occupied?
When were the homes in WINTER OAKS built?
Do cash buyers compete in WINTER OAKS?
Who is the best real estate agent for WINTER OAKS?
How do I find a top WINTER GARDEN real estate agent who knows WINTER OAKS?
Can Momentum Realty connect me with an agent for WINTER OAKS?
Nearby Communities
Explore more neighborhoods near WINTER OAKS with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: August 2, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (community parcel extract) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2006 (50 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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