Cobblestone
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 3 closed sales in Cobblestone/Winter Garden in Winter Garden, FL since 2024, the most recent in May 2026. 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 in Winter Garden doesn't come with a headline amenity package in the current MLS data, which means pricing here tends to track the house itself — lot, layout, condition, and finish level — rather than a shared clubhouse or gate. That puts more weight on a line-by-line look at each listing rather than leaning on a community brand.
For sellers, that translates into presentation mattering more than usual: with no amenity story to lean on, the home has to make its own case on condition and updates. For buyers, it means the community is worth evaluating property by property rather than assuming a uniform standard across the neighborhood.
Nearby homes for sale
No active listings inside Cobblestone/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 sits within Winter Garden in Orange County, and current MLS listings don't surface a defined set of community amenities, so buyers should treat this as a location and housing-stock decision rather than an amenity-driven one.
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 is best for.
Best for
- Buyers focused on the home itself — layout, condition, lot — over a community amenity package
- Buyers who want a Winter Garden location and are comfortable verifying any shared features directly
- Buyers comparing several Winter Garden pockets on housing stock rather than clubhouse or pool access
Probably not for
- Buyers whose top priority is a defined, documented amenity set like a pool or clubhouse
- Buyers unwilling to do extra diligence on community features not reflected in current listings
- Buyers set on a community with an established recreational or social amenity as the primary draw
The market around Cobblestone
Cobblestone 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 specifically. Momentum Research analysis of MLS records.
The Cobblestone buying strategy.
If we were buying in Cobblestone 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.
What's Actually Driving Value Here
Without a documented amenity package showing up in listings, the usual community-level pricing levers — pool access, clubhouse, planned green space — aren't part of the current picture for Cobblestone. That doesn't mean none exist on the ground, only that they aren't showing up as a factor in how homes are currently marketed and priced through the MLS feed.
That shifts the evaluation toward the individual property: layout, lot position, age and condition of the home, and proximity to the rest of Winter Garden. Buyers comparing Cobblestone to other Winter Garden communities should ask directly about any shared features, since that information isn't consistently reflected in listing data right now.
The location and the amenities are priced into every listing in Cobblestone. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
When a community's listing data doesn't spell out shared amenities, the diligence has to happen off the page — verifying what's actually on site, how it's maintained, and whether it factors into value. That's the kind of legwork we do before a showing, not after an offer.
Cobblestone 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 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 sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Cobblestone, 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 home worth?
Get a no-obligation home value based on real comparable sales in Cobblestone, 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 →
Should you buy in Cobblestone?
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 2024 (3 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.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Cobblestone/Winter Garden fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Cobblestone
Where is Cobblestone?
Cobblestone is a community in Winter Garden, Orange County, Florida, ZIP 34787.
Are there homes for sale in Cobblestone right now?
No active listings inside Cobblestone 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 have an HOA or CDD?
No HOA is on record for Cobblestone 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.
Nearby Communities
Explore more neighborhoods near Cobblestone with Momentum Realty’s local guides.