Cobblestone Of Winter Garden
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.
As of September 2026, the MLS records 9 closed sales in Cobblestone Of Winter Garden in Winter Garden, FL since 2008, the most recent in October 2025. Across Winter Garden as a whole, 1,316 homes closed in the last 12 months at a median of $595,000, 38 median days on market, with 348 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $9,920 ($9,250 with the full homestead exemption).
Cobblestone reads as a tight, single-era build: every home here went up in 2006 or 2007, so there is no decades-spanning mix of construction styles or systems ages to sort through. The value story is about floor plan and finish, not build vintage, since almost every home shares the same age profile.
With 83 homes in the community and homestead exemptions on file for about two-thirds of them, this is a base that skews toward owner-occupancy rather than transient rental turnover. For a buyer, that generally means fewer absentee-owner surprises at the HOA table; for a seller, it means your comp set is genuinely comparable in age and scale, which simplifies pricing conversations.
Nearby homes for sale
No active listings inside Cobblestone Of Winter Garden 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
Cobblestone Of Winter Garden is a compact, single-phase community built out entirely in 2006 and 2007, with a typical home running around 2,516 square feet. No community amenities are currently listed in MLS data for this neighborhood, so buyers should treat this as a homes-and-location play rather than a lifestyle-amenity purchase.
Stellar MLS sales records identify 25 homes in Cobblestone Of Winter Garden that have changed hands since 2007, built between 2006 and 2007 (median 2007), with a median living area of about 2,464 sq ft and a typical 4-bedroom, 2.5-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.
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.
Who Cobblestone Of Winter Garden is best for.
Best for
- Buyers who want a consistent, single-era build rather than a mixed-vintage neighborhood
- Move-up buyers targeting a larger footprint, around the 2,500-square-foot range, without amenity fees attached
- Buyers prioritizing a straightforward comp set for easier price comparison
Probably not for
- Buyers who specifically want an HOA-run pool, clubhouse, or fitness facility as part of the purchase
- Buyers seeking the widest possible spread of home ages and architectural styles within one community
- Investors expecting a high concentration of non-homestead, rental-oriented inventory
The market around Cobblestone Of Winter Garden
Cobblestone Of Winter Garden is too small for its own price trend, so here is the market around it.
In ZIP 34787, 957 homes are on the market and 30% are under contract — a steady corner of Winter Garden.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
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.
ZIP and county figures describe the wider market, not Cobblestone Of Winter Garden specifically. Momentum Research analysis of MLS records.
Cobblestone Of Winter Garden by the numbers
From county property records and closed MLS sales for the Cobblestone Of Winter Garden subdivision: 25 homes on record; built 2006–2007; typical size about 2,464 heated sq ft; 4 bedrooms is the median. Housing mix: single-family 100%.
| Year | Recorded sales | Median price |
|---|---|---|
| 2015 | 3 | $300,000 |
| 2016 | 2 | $283,250 |
| 2019 | 1 | $372,500 |
| 2020 | 1 | $385,000 |
| 2021 | 1 | $425,000 |
| 2025 | 2 | $541,850 |
Newest recorded sale: $538,700 on 2025-10-10.
Recorded data as of 2026-09-12; counts cover addresses tagged to this subdivision in the public record, not every parcel. Not an appraisal.
The Cobblestone Of Winter Garden buying strategy.
If we were buying in Cobblestone Of Winter Garden 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 Cobblestone Of Winter Garden.
One build era, one clear comp set
Because every home in Cobblestone dates to 2006 or 2007, the usual noise that complicates pricing in older or phased communities — mixed construction codes, wide vintage gaps, a patchwork of renovation states — mostly falls away here. What differentiates one listing from another is condition, updates, and layout, not decade of construction.
At a median of roughly 2,516 living square feet, this is a mid-to-larger single-family footprint for the immediate area, which tends to suit buyers who have outgrown a starter home but are not necessarily shopping the high end of the market. With no HOA-run amenities identified in current MLS data, due diligence should focus on the individual home and any private community documents rather than assuming a clubhouse, pool, or gate is part of the package.
The location and the amenities are priced into every listing in Cobblestone Of Winter Garden. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
A community this uniform in age and size still has real spread in condition and updates from one listing to the next. We track those distinctions house by house rather than leaning on a generic neighborhood average, so pricing conversations are grounded in what is actually on the market, not a placeholder figure.
Cobblestone Of Winter Garden in 15 seconds.
HOA, CDD & Fees
- 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.
Tools for a Cobblestone Of Winter Garden 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 Cobblestone Of Winter Garden sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Cobblestone Of Winter Garden, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Cobblestone Of Winter Garden home worth?
Get a no-obligation home value based on real comparable sales in Cobblestone Of Winter Garden, 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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Should you buy in Cobblestone Of Winter Garden?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2008 (9 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 Cobblestone Of Winter Garden fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Cobblestone Of Winter Garden
Where is Cobblestone Of Winter Garden?
Cobblestone Of Winter Garden is a community in Winter Garden, Orange County, Florida, ZIP 34787.
How many homes are in Cobblestone Of Winter Garden?
County property records list 25 homes in Cobblestone Of Winter Garden, built between 2006 and 2007; the typical home is about 2,464 heated square feet.
What do homes in Cobblestone Of Winter Garden sell for?
Cobblestone Of Winter Garden has no MLS sales in the last 12 months. The most recent year with recorded sales on file is 2025 (2 sales, median $541,850). For context, ZIP 34787 has 957 homes on the market with 30% under contract.
Are there homes for sale in Cobblestone Of Winter Garden right now?
No active listings inside Cobblestone Of Winter Garden at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Cobblestone Of Winter Garden have an HOA or CDD?
No HOA is on record for Cobblestone Of Winter Garden in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
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