Deer Island
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.
Over the 12 months ending 2026-09-20, 4 recorded sales closed at a median of $1,437,500, $444 per square foot, a median 108 days on market, sellers accepting 86% of original asking. At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $23,970 ($23,300 with the full homestead exemption).
Deer Island Ph 02 is a small subdivision inside Winter Garden, and with only a two-closing window to work from, this is a thin-data market. What that means in practice: individual sales carry outsized weight, and no single comp should be treated as the market. Price here is driven by the specifics of each home — condition, updates, lot, and how the property shows — far more than by any neighborhood-wide trend you could pin a number to.
For a seller, thin volume cuts both ways: it can protect a well-presented home from being dragged down by weaker comps, but it also means buyers and appraisers have little to anchor to, so preparation and pricing discipline matter more than usual. For a buyer, the takeaway is patience. With few closings to reference, do the work on the individual house rather than assuming the block sets the value.
Figures in this note are as of July 14, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside Deer IslandHomes for Sale in Winter Garden, 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
Deer Island market snapshot (as of September 20, 2026): the median sale price is about $1.44M ($444 per sq ft over the trailing 12 months of closed sales), and a median 108 days on market for closed sales.
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.
County records show 4 qualified sales in Deer Island across 2024–2025 (3 in 2024, 1 in 2025), median $1.32M — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Deer Island is a community of 122 homes in Winter Garden, Orange County, built between 1985 and 2023 (median 1999), with a median living area of about 3,760 square feet. 79% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Deer Island Ph 02 is a compact pocket of Winter Garden in Orange County. Because so few homes trade here in any given window, it behaves like a boutique market where each listing stands largely on its own merits.
Who Deer Island is best for.
Best for
- Buyers targeting a particular Winter Garden pocket and willing to wait for the right home to come up
- Buyers comfortable evaluating a property on its own condition and features rather than a wall of comparable sales
- Sellers with an updated, show-ready home who want to stand out in a low-inventory setting
Probably not for
- Buyers who need extensive recent sales data to feel confident on price
- Buyers on a tight timeline who cannot wait for limited inventory to turn over
- Sellers hoping a broad neighborhood trend will carry a home that needs work
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($1.44M) IS the median in the snapshot above.
Windows contain 0 to 7 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 2004 through 2026. Deemed reliable but not guaranteed.
29% of homes for sale in ZIP 34787 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-09-20).
The Deer Island buying strategy.
If we were buying in Deer Island 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 Deer Island.
Reading a thin market
The single most important thing to understand about Deer Island Ph 02 right now is scale. This is a limited-inventory community, and the closing activity we can verify is small. That is not a knock on the neighborhood — it is simply the reality of a smaller subdivision — but it changes how you should read every data point you encounter. One updated home or one dated home can swing the apparent picture, so we weight condition and features over headline averages.
Practically, that argues for a comp-by-comp approach rather than a market-wide narrative. We look at what has actually closed, how those homes presented, and how they compare feature-for-feature to the property in front of you. Winter Garden's broader location and amenities give this pocket its underlying appeal; the pricing work happens house by house.
The location and the amenities are priced into every listing in Deer Island. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a low-volume community like Deer Island Ph 02, the value we add is judgment where the data runs out. We do not lean on a formula or an automated estimate; we build the case for a specific home from the closings that exist, adjust for condition and features, and tell you plainly where the number is soft. Whether you are buying or selling, that discipline matters most exactly when there are few comps to hide behind.
Deer Island 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 Deer Island 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 Deer Island sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Deer Island, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Deer Island home worth?
Get a no-obligation home value based on real comparable sales in Deer Island, 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 →
| Location | Winter Garden, Orange County, FL · ZIP 34787 |
|---|---|
| Homes in the community | 122 (FL DOR 2025 assessment roll) |
| Years built | 1985–2023 (median 1999) |
| Typical living area | 3,760 sq ft (median) |
| Sale prices, last 12 months | $1,437,500 median across 4 closed sales · $444 per sq ft |
| Days on market (closed sales) | 108 median |
| Owner-occupied (homestead) share | 79% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2004 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Deer Island key facts,” movewithmomentum.com/neighborhoods/deer-island-ph-02, data as of September 20, 2026.
Housing distress & ownership in Deer Island Ph 02, 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.
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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
- Florida property tax by county
- 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.
- Deer Isle Circle (33 homes on record)
- Deer Isle Circle (12 homes on record)
- Deer Isle Circle (3 homes on record)
- Deer Isle Circle (1 homes on record)
Email me new listings in Deer Island
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Deer IslandHomes for Sale
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Deer IslandHomes for Sale will answer, and the answer is published on this page for the next buyer.
Recent Developments in Deer Island Ph 02
Development, infrastructure, retail, and school activity affecting Deer Island Ph 02, 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 6 miles northeast of Deer Island Ph 02.
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 10 miles northwest of Deer Island Ph 02.
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 4 miles northeast of Deer Island Ph 02.
Source: FOX 35 Orlando - July 2026Development
Capstone begins construction on The Gateway luxury apartments
Capstone Building Corp began construction on The Gateway, a 270-unit apartment community at 7250 Shadowridge Drive in Orlando, developed by JBL Development. The five-story gated project spans more than 417,000 square feet and is expected to be completed in late 2027. Amenities include a saltwater pool, fitness center, pickleball court, and a clubhouse with a restaurant and bar.
What it may mean for the marketAdds 270 market rate apartments in a five story building with resort style amenities, expanding the local rental housing stock in the Airport Lakes area of south Orlando. The project is about 15 miles northeast of Deer Island Ph 02, elsewhere in Orange County.
Source: Construction Owners - 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 13 miles northeast of Deer Island Ph 02, 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 15 miles north of Deer Island Ph 02, elsewhere in Orange County.
Source: Orange County Newsroom
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.
Frequently Asked Questions
What is the median home price in Deer Island?
How long do homes in Deer Island take to sell?
How many homes are in Deer Island?
What share of Deer Island is owner-occupied?
When were the homes in Deer Island built?
Who is the best real estate agent for Deer Island?
How do I find a top Winter Garden real estate agent who knows Deer Island?
Can Momentum Realty connect me with an agent for Deer Island?
Where is Deer Island, and what county is it in?
Should you buy in Deer Island?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (3 streets, ZIP 34787)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2004 (50 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.
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