Winter Garden Trails
Homes for Sale in Winter Garden, FL
All 720 homes for sale in WINTER GARDEN, FL · median $575,000 · 509 homes for sale in 34787 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-09-12, 4 recorded sales closed at a median of $485,000, $210 per square foot, a median 29 days on market, sellers accepting 96% of original asking. Homes listed or recently sold were built 2005 - 2007; 4 of 4 report an HOA (median $55/mo); none of the 4 geocoded homes sit in a FEMA special flood hazard zone (median elevation 116 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $8,090 ($7,410 with the full homestead exemption).
This is a small, tightly built pocket of 55 homes, all constructed within a narrow 2005-2007 window, which keeps the housing stock consistent in age and layout. With zero active listings at the time of this snapshot, there is effectively nothing on the market to compare against - pricing here has to be read from recent closings rather than current competition.
The median sale of $500,000 against a median of 2,381 square feet works out to roughly $212.95 per square foot, and the median 51 days on market suggests these homes don't move instantly but also aren't sitting stale. With a large majority of owners carrying a homestead exemption, this reads as a community where people buy to stay, not to flip, which is part of why turnover and inventory both run thin.
Nearby homes for sale
No active listings inside Winter Garden Trls 01 3 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.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Winter Garden Trails market snapshot (as of September 12, 2026): the median sale price is about $485K ($210 per sq ft over the trailing 12 months of closed sales), and a median 29 days on market for closed sales.
In ZIP 34787 (WINTER GARDEN), 2,162 homes closed in the last 12 months at a median of $595K ($251/sq ft), down 0.6% year over year, with a median 36 days on market. Right now 357 active and 169 pending listings put supply at about 3.8 months - a balanced market. See the live ZIP 34787 housing market and the Orange County market.
Stellar MLS sales records identify 20 homes in Winter Garden Trails that have changed hands since 2015, built between 2005 and 2007 (median 2006), with a median living area of about 2,460 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.
A single-phase, deed-restricted community in Winter Garden built out over a tight two-to-three year span in the mid-2000s, offering a consistent size and age profile rather than a mix of eras.
The setting & the homes.
Aerial and on-site photos of Winter Garden Trails. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Winter Garden Trails
Winter Garden Trails
Winter Garden Trails
Winter Garden TrailsPhotos from Stellar MLS listings in Winter Garden Trails; content deemed reliable but not guaranteed.
Who Winter Garden Trails is best for.
Best for
- A buyer who has already identified this specific community and is willing to wait for the right listing rather than needing options today.
- A buyer comfortable with a mid-2000s-built home in the roughly 2,381-square-foot range and a median price near $500,000.
- A buyer who values a deed-restricted, single-phase community with a consistent build era over a mixed-vintage neighborhood.
Probably not for
- A buyer who wants to shop multiple active listings and compare condition, price, and layout before deciding.
- A buyer working under a hard deadline who cannot absorb the uncertainty of near-zero current inventory.
- A buyer specifically seeking a wider range of home sizes or ages than this narrow 2005-2007 build window offers.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 12 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($485K) IS the median in the snapshot above.
Windows contain 0 to 4 sales each (4 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 2016 through 2026. Deemed reliable but not guaranteed.
WINTER GARDEN TRLS 01-3 Market Scorecard
WINTER GARDEN TRLS 01-3 is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 34787 ZIP is $574,696, right around the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, 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 Garden Trls 01 3, 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 September 2026 through September 2026. Deemed reliable but not guaranteed.
Winter Garden Trails 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 Garden Trails
- Deed Restrictions · reported on 1 of 3 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.
The Winter Garden Trails buying strategy.
If we were buying in Winter Garden Trails 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 Garden Trails.
A tight, consistent pocket with almost no inventory
Because Winter Garden Trls 01 3 was built out entirely between 2005 and 2007, buyers aren't choosing between old and new construction here - every home shares a similar age and general construction era, with the main variables being condition, updates, and lot position. At a median 2,381 square feet, these are mid-sized homes, not the smallest or largest product in the broader Winter Garden market.
The current snapshot shows zero active listings, based on the last 3 months of closing activity used to establish these figures. That combination - no listings, a homestead share suggesting most owners are settled in as primary residences, and a median 51-day market time - points to a community where available homes are the exception, not the rule, and where a serious buyer needs to move with a plan already in place rather than expecting a deep pool to shop from.
The location and the amenities are priced into every listing in Winter Garden Trails. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community with no active listings, the work happens before a sign ever goes up - tracking off-market activity, understanding what recent closings actually looked like inside these 55 homes, and being ready to act the moment something surfaces. We treat a near-zero-inventory pocket like this one as a watch-and-wait assignment, not a browse-the-listings one.
Winter Garden Trails in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $55/month (about $660/yr) · median of 12 MLS listings, most billed annually
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $55 per month ($660 a year) - the median AssociationFee across 12 MLS records, normalised to a monthly figure; most are billed annually. 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, 2026-09.
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 Garden Trails 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 Garden Trails sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winter Garden Trails, 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 Garden Trails home worth?
Get a no-obligation home value based on real comparable sales in Winter Garden Trails, 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 →
Frequently Asked Questions
What is the median home price in Winter Garden Trails?
How long do homes in Winter Garden Trails take to sell?
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Should you buy in Winter Garden Trails?
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: September 14, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2016 (14 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 local comps.
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See how Winter Garden Trls 01 3 fits the bigger picture — live prices, inventory, and Momentum Scores:
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