Winter Garden Shores
Homes for Sale in Winter Garden, FL
All 701 homes for sale in WINTER GARDEN, FL · median $585,000 · 645 homes for sale in 34787 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
As of October 2026, the MLS records 17 closed sales in Winter Garden Shores Add 02 in Winter Garden, FL since 2005, the most recent in December 2025. Across Winter Garden as a whole, 1,339 homes closed in the last 12 months at a median of $597,500, 38 median days on market, with 342 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $9,960 ($9,290 with the full homestead exemption).
| Location | WINTER GARDEN, Orange County, FL · ZIP 34787 |
|---|---|
| Homes in the community | 453 (FL DOR 2025 assessment roll) |
| Years built | 1906–2024 (median 1959.0) |
| Typical living area | 1,744 sq ft (median) |
| Amenities listed by sellers | Security Gate, Security System |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 61% |
Data as of August 2, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2025; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “WINTER GARDEN SHORES ADD 02 key facts,” movewithmomentum.com/neighborhoods/winter-garden-shores-add-02, data as of August 2, 2026.
Winter Garden Shores Add 02 is an older pocket by Northeast Florida standards, with a median build year of 1959 and a housing stock that stretches all the way from 1906 to 2024. That range is the story: price here is driven less by a headline number than by condition and by how much of the original structure a given seller has touched. Two homes on the same street can trade very differently depending on renovation, systems, and lot.
With a median living area around 1,744 square feet, this is a mid-size, established inventory rather than a new-construction tract. About 60% of homes carry a homestead exemption, which points to an owner-occupied core and typically thinner turnover. For buyers that means less to choose from at any given moment; for sellers it means a well-prepared, correctly-priced home does not have to compete against a flood of listings.
Nearby homes for sale
No active listings inside WINTER GARDEN SHORES ADD 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
This is an established Winter Garden community of 295 homes where the age spread — a century of building from 1906 through 2024 — matters more than any single price point. Expect to evaluate each house on its own condition and updates.
Stellar MLS sales records identify 80 homes in WINTER GARDEN SHORES that have changed hands since 2006, built between 1928 and 2019 (median 1960), with a median living area of about 1,718 sq ft and a typical 3-bedroom, 2-bath layout; 100% 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.
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 Winter Garden Shores is best for.
Best for
- Buyers who want an established Winter Garden location and will budget for inspections and updates
- Renovation-minded buyers looking for an older home with upside from targeted improvements
- Long-hold owner-occupants who value a stable, low-turnover community
Probably not for
- Buyers who need new construction with modern systems and warranties
- Buyers wanting a uniform subdivision where every home is comparable
- Buyers with no budget or appetite for maintenance on an older structure
The market around Winter Garden Shores
Winter Garden Shores is a small community — 21 recorded sales on file, most recently in 2025 — too few for its own price trend. Here is the market around it.
In ZIP 34787, 984 homes are on the market and 28% are under contract — a steady corner of Winter Garden.
Across Orange County, 5,873 homes are active and 2,054 pending (26% under contract).
Homes here are single family residence.
In ZIP 34787 (WINTER GARDEN), 2,147 homes closed in the last 12 months at a median of $598K ($252/sq ft), down 0.8% year over year, with a median 36 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 Winter Garden Shores specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in WINTER GARDEN SHORES ADD 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.
Homes For Sale Right Now in Winter Garden Shores
Live MLS inventory for Winter Garden Shores. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Winter Garden Shores listings as of 2026-10-01, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2025. Tap any home to ask about it.
Every Home for Sale in Winter Garden Shores Add 02 Right Now (1)
All 1 active and pending Winter Garden Shores Add 02 listings with a detail page, newest first, refreshed twice a day from the MLS.
- 368 N Boyd Street · $799,000 · 4 bd / 2.5 ba · listed Sep 2, 2026 · listed by Fathom Realty Fl Llc
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Dillard Street Elem · Elementary
- Lakeview Middle · Middle
- West Orange High · High
Zoned schools reflect the assignments reported on recent Winter Garden Shores listings and can change; always confirm with Orange County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Winter Garden Shores address.
Shop the zone: Homes zoned for West Orange High High School
The Winter Garden Shores buying strategy.
If we were buying in Winter Garden Shores 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 Winter Garden Shores.
Why condition sets the price here
When the median home dates to 1959 and the oldest stock reaches back to 1906, the variable that moves value is the work that has — or has not — been done. Roof, plumbing, electrical, and foundation age are the real line items, and a renovated home and a time-capsule original in the same 1,744-square-foot range can command very different numbers. Buyers should underwrite inspection and update costs, not just the sticker.
The mix of ages also means variety: newer infill built as recently as 2024 sits alongside genuinely old homes. That keeps the community from feeling uniform, but it also means comps require judgment. Momentum's job here is to read those differences accurately rather than lean on a single average.
The location and the amenities are priced into every listing in Winter Garden Shores. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
A community with a century-wide build range and a condition-driven market rewards local pricing judgment over automated estimates. We evaluate each home against its true peers — accounting for age, updates, and square footage — so buyers avoid overpaying for deferred maintenance and sellers price to the work they have actually done.
Winter Garden Shores 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 Winter Garden Shores 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 Winter Garden Shores sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winter Garden Shores, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Winter Garden Shores home worth?
Get a no-obligation home value based on real comparable sales in Winter Garden Shores, 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 →
27% 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 (2026-10-02).
Frequently Asked Questions
How many homes are in Winter Garden Shores?
What share of Winter Garden Shores is owner-occupied?
When were the homes in Winter Garden Shores built?
Do cash buyers compete in Winter Garden Shores?
Who is the best real estate agent for Winter Garden Shores?
How do I find a top Winter Garden real estate agent who knows Winter Garden Shores?
Can Momentum Realty connect me with an agent for Winter Garden Shores?
Where is Winter Garden Shores, and what county is it in?
Should you buy in Winter Garden Shores?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 1, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (8 streets, ZIP 34787)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2005 (17 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 WINTER GARDEN SHORES ADD 02 fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Winter Garden Shores with Momentum Realty’s local guides.