Cobblestone
Homes for Sale in Winter Garden, FL
All 749 homes for sale in Winter Garden, FL · median $589,900 · 706 homes for sale in 34787 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 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, 1,339 homes closed in the last 12 months at a median of $595,000, 38 median days on market, with 694 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.
Figures in this note are as of July 21, 2026. The live market numbers elsewhere on this page update nightly and are newer.
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.
County records show 6 qualified sales in Cobblestone/Winter Garden across 2024–2025 (3 in 2024, 3 in 2025), median $547,500 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
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), 2,123 homes closed in the last 12 months at a median of $595K ($252/sq ft), down 0.9% year over year, with a median 37 days on market. Right now 352 active and 181 pending listings put supply at about 3.7 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.
Recent Developments in Cobblestone
Development, infrastructure, retail, and school activity affecting Cobblestone, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- September 2026Development
Orange County commissioners approve Tuscana land use plan in Shingle Creek Basin on 4-3 vote
Commissioners voted 4-3 to approve the Tuscana land use application from Shingle Creek Co-Owners LLC and Geyer Development, reversing a unanimous rejection in May 2025. The plan includes more than 1,000 hotel rooms, about 4,000 apartments and commercial buildings, with conditions for a raised road, flood mitigation and wetland protection. The developer projects thousands of jobs at full build-out.
What it may mean for the marketThe approval could add substantial rental housing, hotel capacity and commercial space in the Shingle Creek area, while flood-mitigation conditions will shape how and when it is built. The site is about 7 miles southeast of Cobblestone.
Source: Spectrum News 13 - September 2026Development
Lake County approves 2,241-acre Panther Run rezoning for up to 2,624 homes near Clermont
The Lake County Commission voted 3-1 on Sept. 1 to rezone about 2,241 acres in the Wellness Way area, north of Sawgrass Bay Boulevard, for GT Homes. The planned unit development allows up to 2,624 residential units and more than 1 million square feet of non-residential space, with sites reserved for a future public high school and public safety facilities. Plans include extending County Road 455 and about 11 miles of public trails.
What it may mean for the marketThe plan adds long-term housing supply, employment space and new connector roads in south Lake County, with infrastructure planned ahead of residential growth. The site is about 9 miles west of Cobblestone.
Source: Clermont Sun - August 2026Retail & Dining
Plans for Mattel indoor water park near Lake Buena Vista Factory Stores expand to 13 acres
Updated plans for the site off State Road 535 show a 95,000-square-foot indoor water park designed by Martin Aquatic, a separate 45,000-square-foot entertainment building and nearly 900 parking spaces. The tower height rises to as much as 100 feet and still needs Orange County approval. About 200 jobs are expected, and no opening date has been announced.
What it may mean for the marketThe project would add visitor attractions, dining and roughly 200 jobs near the State Road 535 corridor, with added traffic and parking demand nearby. The site is about 5 miles southeast of Cobblestone.
Source: FOX 35 Orlando - July 2026Development
Orange County opens Enclave at Canopy Park with 104 affordable units
Orange County opened The Enclave at Canopy Park, a 104-unit affordable apartment community at 4440 Canopy Park Loop developed by Archway Partners. The county contributed 3 million dollars from its Affordable Housing Trust Fund. The community includes one and two bedroom homes plus a community center, fitness center, technology lab, and EV charging.
What it may mean for the marketAdds 104 income-restricted apartment homes to the local rental supply along with new community amenities and green-certified construction. The project is about 10 miles east of Cobblestone, elsewhere in Orange County.
Source: ClickOrlando - July 2026Civic
Orange County previews new Innovation Center on West Colonial Drive
Orange County previewed its new Innovation Center at 7149 West Colonial Drive, located within the county's Multicultural Center and Senior Center complex, with an official opening set for Fall 2026. The center will offer technology programs including 3D printing and makerspace prototyping through the Orange County Library System, plus career exploration and workforce training through CareerSource Central Florida.
What it may mean for the marketAdds a county operated civic and technology facility with library and workforce programming to the West Colonial corridor. The project is about 9 miles northeast of Cobblestone, elsewhere in Orange County.
Source: Orange County Newsroom - June 2026Development
Planning board approves zoning for 37-story tower at 170 East Washington Street
Orlando's Municipal Planning Board voted to approve a Planned Development amendment for a 37-story, 425-foot mixed-use tower at 170 East Washington Street across from Lake Eola Park. The project would include 252 residential units, a 221-room hotel, a three-story restaurant, and structured parking. It still requires City Council consideration before construction.
What it may mean for the marketWould add a 37 story tower with 252 residences and a hotel to the downtown skyline, replacing a prior approval for a 7 story hotel and increasing high density housing and parking supply. The project is about 12 miles northeast of Cobblestone, elsewhere in Orange County.
Source: Florida YIMBY
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in the Orlando Metro.
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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.
| Location | Winter Garden, Orange County, FL · ZIP 34787 |
|---|---|
| Homes in the community | 51 (FL DOR 2025 assessment roll) |
| Years built | 2006–2007 (median 2007) |
| Typical living area | 2,470 sq ft (median) |
| Owner-occupied (homestead) share | 59% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2024 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Cobblestone key facts,” movewithmomentum.com/neighborhoods/cobblestone-winter-garden, data as of September 20, 2026.
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Winter Garden guides & data
- Market data
- Cost of living
- Best neighborhoods
- Flood zones
- Property taxes (Orange County)
- Homestead exemption (Orange County)
- Home insurance cost
- New construction
Florida buyer guides
- Florida home insurance rates by county
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- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Black Springs Lane (4 homes on record)
Nearby Communities
Explore more neighborhoods near Cobblestone with Momentum Realty’s local guides.