Deer Island
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.
Over the 12 months ending 2026-09-12, 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.
Nearby homes for sale
No active listings inside Deer Island Ph 02 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 12, 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), 2,162 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.
Stellar MLS sales records identify 63 homes in Deer Island that have changed hands since 2005, built between 1985 and 2023 (median 1997), with a median living area of about 3,747 sq ft and a typical 4-bedroom, 3.5-bath layout; 98% 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.
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 12 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.
30% 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 (2026-09-08).
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.
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Frequently Asked Questions
What is the median home price in Deer Island?
How long do homes in Deer Island take to sell?
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?
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 12, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| 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.
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 Deer Island Ph 02 fits the bigger picture — live prices, inventory, and Momentum Scores:
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