Vineyard Square
Homes for Sale in Windermere, FL
All 240 homes for sale in Windermere, FL · median $950,000 · 209 homes for sale in 34786 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, the MLS records 5 closed sales in Vineyard Square in Windermere, FL since 2014, the most recent in March 2024. Across Windermere as a whole, 449 homes closed in the last 12 months at a median of $640,000, 39 median days on market, with 225 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $10,670 ($10,000 with the full homestead exemption).
Vineyard Square is a tightly built pocket of Windermere, all 201 homes going up within a six-year window between 2013 and 2019. That kind of construction consistency means less variation in systems age or building materials than you'd find in a neighborhood assembled over decades, which narrows the usual due-diligence questions to lot position, floor plan, and how well a given owner has maintained finishes since closing.
With just over half of homes carrying a homestead exemption, this reads as a community with a real mix of owner-occupants and non-homesteaded owners, rather than one dominated by either long-term holders or short-term rental turnover. For buyers, that suggests inventory here comes from ordinary life-stage moves as much as investment exits — worth confirming occupancy status on any listing before you assume how move-in-ready it will be.
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 Vineyard SquareHomes for Sale in Windermere, FL 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
Vineyard Square sits in Windermere, Orange County, as a single-era community built out almost entirely between 2013 and 2019 — a footprint of 201 homes with a median size around 2,090 square feet and a median year built of 2015.
Stellar MLS sales records identify 18 homes in Vineyard Square that have changed hands since 2014, built between 2014 and 2019 (median 2017), with a median living area of about 2,090 sq ft and a typical 3-bedroom, 2.5-bath layout; 94% are townhomes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
County records show 7 qualified sales in Vineyard Square across 2024–2025 (4 in 2024, 3 in 2025), median $465,000 — 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 Vineyard Square is best for.
Best for
- Buyers who want a home built within the last decade-plus without needing to compare eras of construction
- Buyers targeting a mid-size footprint around 2,000+ square feet in Windermere
- Buyers comfortable doing direct diligence on HOA and amenity terms rather than relying on listing summaries
Probably not for
- Buyers who need a confirmed, listed amenity package before touring
- Buyers seeking older or architecturally varied housing stock
- Buyers who want a neighborhood with a long, established resale history spanning multiple decades
The market around Vineyard Square
Vineyard Square is too small for its own price trend, so here is the market around it.
In ZIP 34786, 336 homes are on the market and 26% are under contract — a steady corner of Windermere.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
In ZIP 34786 (Windermere), 788 homes closed in the last 12 months at a median of $640K ($261/sq ft), down 0.6% year over year, with a median 40 days on market. Right now 131 active and 43 pending listings put supply at about 3.7 months — a balanced market. See the live ZIP 34786 housing market and the Orange County market.
ZIP and county figures describe the wider market, not Vineyard Square specifically. Momentum Research analysis of MLS records.
Vineyard Square by the numbers
From county property records and closed MLS sales for the Vineyard Square subdivision: 17 homes on record; built 2014–2017; typical size about 1,913 heated sq ft; 3 bedrooms is the median. Housing mix: townhome 94%, single-family 5%.
| Year | Recorded sales | Median price |
|---|---|---|
| 2014 | 2 | $250,592 |
| 2015 | 2 | $242,358 |
| 2017 | 4 | $296,724 |
| 2018 | 8 | $289,970 |
| 2024 | 1 | $625,000 |
Newest recorded sale: $625,000 on 2024-03-14.
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 Vineyard Square buying strategy.
If we were buying in Vineyard Square 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 Vineyard Square.
One build era, one clear question mark
The story of Vineyard Square starts with its age band: every home dates to a narrow 2013–2019 stretch, with the median build year sitting at 2015. That uniformity is useful for buyers comparing homes on paper — you're largely evaluating floor plan, lot, and finish level rather than decade-to-decade construction differences. At a median living area of 2,090 square feet, the homes here land in a mid-size range that works for a variety of layouts without skewing toward either compact or expansive.
One point buyers should press on directly: current MLS listings show no community amenities identified. That doesn't necessarily mean there are none — it means the amenity picture isn't documented in the data feed we're working from, so confirming HOA structure, any shared facilities, and what (if anything) dues cover should be an early step in any offer, not an afterthought.
The location and the amenities are priced into every listing in Vineyard Square. 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 rewards a close read of the details that actually differ — lot placement, orientation, updates since original construction, and true HOA terms where public listing data goes quiet. We pull those threads before you write an offer, not after.
Vineyard Square 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 Vineyard Square 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 Vineyard Square sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Vineyard Square, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Vineyard Square home worth?
Get a no-obligation home value based on real comparable sales in Vineyard Square, 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 Windermere →
Should you buy in Vineyard Square?
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 2014 (5 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 Vineyard Square
Development, infrastructure, retail, and school activity affecting Vineyard Square, 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 9 miles south of Vineyard Square.
Source: Spectrum News 13 - 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 9 miles south of Vineyard Square.
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 4 miles southeast of Vineyard Square, 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 site is about 2 miles north of Vineyard Square.
Source: Orange County Newsroom - June 2026Development
Mixed-use high-rise redesigned for 924 and 934 North Magnolia Avenue
A redesigned 17-story mixed-use high-rise was proposed for 924 and 934 North Magnolia Avenue in Orlando's North Quarter district by Acram Group. The project would include 350 residential units, about 3,300 square feet of ground-floor commercial space, and a parking garage with 510 spaces, replacing two 1972 office buildings. A public plaza is planned at the corner of Magnolia and Weber Street.
What it may mean for the marketWould replace two aging office buildings with 350 residences, ground floor retail, and structured parking, adding housing density and a public plaza along the Orlando Urban Trail. The project is about 5 miles northeast of Vineyard Square, elsewhere in Orange County.
Source: Florida YIMBY - 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 5 miles east of Vineyard Square, 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 Northeast Florida.
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Common questions about Vineyard Square
Where is Vineyard Square?
Vineyard Square is a community in Windermere, Orange County, Florida, ZIP 34786.
How many homes are in Vineyard Square?
County property records list 17 homes in Vineyard Square, built between 2014 and 2017; the typical home is about 1,913 heated square feet.
What do homes in Vineyard Square sell for?
Vineyard Square has no MLS sales in the last 12 months. The most recent year with recorded sales on file is 2024 (1 sale, median $625,000). For context, ZIP 34786 has 336 homes on the market with 26% under contract.
Are there homes for sale in Vineyard Square right now?
No active listings inside Vineyard Square at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Vineyard Square have an HOA or CDD?
No HOA is on record for Vineyard Square 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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Windermere guides & data
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