OVERSTREET CRATE in WINTER GARDEN

OVERSTREET CRATE
Homes for Sale in WINTER GARDEN, FL

Community in WINTER GARDEN · Orange County · ZIP 34787
340 homesBuilt 1909–2024
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Built fromLive Stellar MLS data11 years of closingsFL DOR public recordsUpdated twice daily
Live · OVERSTREET CRATE Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Tempo
12.0mo
Supply
3 to 6 months is the balanced band
0%
Under contract
Orange: 26% (2,054 of 7,927)
2 · 0
For sale · pending
live counts, refreshed twice daily
1
Sold · last 12 mo
10-yr average: about 2 a year
Ownership and context
51%
Owner-occupied · OVERSTREET CRATE
185 of 361 parcels homesteaded (FL DOR 2025)
49%
Non-owner-occupied · OVERSTREET CRATE
incl. 16% trust or LLC-held · 100% out-of-state
25%
Cash buyers · OVERSTREET CRATE
1 of 4 sales, 12 mo ending June 2025
340
Homes in the community
plus 21 vacant residential lots · 361 residential parcels (FL DOR 2025)
Track record · 11 years of records
Est. 1909
Community established
homes built 1909-2024, median 1959 (FL DOR 2025)
1
Failed listings · 2026
peaked at 4 in 2018
0.3%/yr
Turnover rate
about 1 of 340 homes trade a year
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Overstreet Crate is an older pocket of Winter Garden, with a median build year of 1959 sitting inside a much wider span that runs from 1909 up through 2024. That spread means condition and vintage do more to set price here than location alone - a fully updated newer build and a century-old original can sit on the same street with very different numbers behind them.

With only 2 active listings against a 12-month supply, this is a thin market by any measure. That combination points to a buyer-leaning posture on paper, but it is really a low-volume one: few homes trade at any given time, so pricing conversations here are decided listing by listing rather than by broad trend.

OVERSTREET CRATE Housing Pulse · Momentum Research · as of August 2, 2026

OVERSTREET CRATE right now

🟢 Buyer-leaning market. 12.0 months of supply and 0% of the inventory already under contract give buyers above-average negotiating leverage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of August 2, 2026. Confidence: Low (2 active and pending listings, 1 closed sales in 12 months).

Jump to: Price history & scorecard · Homes for sale · Schools · FAQ

Updated August 2, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness

The 60-Second Overview

A small, established pocket of Winter Garden - 340 homes total - where build years run from 1909 to 2024 and the typical home sits at 1,367 square feet. Just over half of homes here carry homestead status, consistent with an area built out gradually rather than in a single development cycle.

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.

Best for

  • Buyers focused on Winter Garden who are flexible on home age and willing to evaluate condition property by property.
  • Buyers comfortable moving quickly when one of the few active listings matches their needs.
  • Sellers with a home in solid, updated condition who can stand out in a market with very few competing listings.

Probably not for

  • Buyers who want to compare several active listings side by side before deciding.
  • Buyers seeking a home with established community amenities, since none are currently identified from MLS data.
  • Sellers expecting a fast, high-volume sale process given the current 12-month supply.

The market around OVERSTREET CRATE

OVERSTREET CRATE is a small community — 22 recorded sales on file, most recently in 2026 — 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).

The housing mix here is 90% single family residence, 7% mobile home - pre 1976, 3% half duplex.

ZIP and county figures describe the wider market, not OVERSTREET CRATE specifically. Momentum Research analysis of MLS records.

Housing distress & ownership in OVERSTREET CRATE, WINTER GARDEN

Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.

Active inventory in distress
0.0%
0 of 3 listings
Distress share trend - 0.0% now (2026-08-12 → 2026-08-18)

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 August 2026 through August 2026. Deemed reliable but not guaranteed.

Homes For Sale Right Now in OVERSTREET CRATE

Live MLS inventory for OVERSTREET CRATE. 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 OVERSTREET CRATE listings as of 2026-08-20, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2015 through 2026. Tap any home to ask about it.

Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.

Schools

In short
  • Orange County Public Schools
  • Verify the zoned schools by address
  • Magnet and choice options may be available
  • William Frangus Elem · Elementary
  • Lakeview Middle · Middle
  • West Orange High · High

Zoned schools reflect the assignments reported on recent OVERSTREET CRATE 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 OVERSTREET CRATE address.

If we were buying in OVERSTREET CRATE today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 OVERSTREET CRATE.

Best Buy
Buyers or sellers comfortable navigating a low-inventory, older housing stock where each home is evaluated on its own merits.
Biggest Risk
With only 2 active listings and 12 months of supply, there is limited current inventory to gauge pricing trends against.
Sweet Spot
Buyers targeting a modest-footprint home, around 1,367 square feet, in an established part of Winter Garden.
Avoid If
You need a wide active selection to compare against right now - this is not a high-volume market.

A market defined by scarcity, not volume

With 2 active listings and 12 months of supply, Overstreet Crate does not behave like a typical subdivision market. There simply is not enough current inventory to establish a clear trend line - every listing that does come up carries outsized weight in shaping perception of value for the area.

The age range of the housing stock, 1909 through 2024, is the other defining variable. A community built out over more than a century means lot size, layout, and system age vary far more than in a single-phase build. Buyers should expect to evaluate each home on its own condition and recent updates rather than assuming consistency across the area.

The location and the amenities are priced into every listing in OVERSTREET CRATE. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

Why work with Momentum here

In a market this thin - 2 active listings against a full year of supply - pricing a home or making an offer requires reading condition and recent comparable activity carefully rather than leaning on volume trends that do not exist yet. We track the Overstreet Crate listings as they surface and help buyers and sellers price against the realistic pool of comparable homes rather than assumptions built for larger, more active subdivisions.

OVERSTREET CRATE in 15 seconds.

Best forBuyers or sellers comfortable navigating a low-inventory, older housing stock where each home is evaluated on its own merits.
Biggest advantageA wide build-year range gives buyers options between original-condition and newer construction within the same small area.
Biggest riskWith only 2 active listings and 12 months of supply, there is limited current inventory to gauge pricing trends against.
Sweet spotBuyers targeting a modest-footprint home, around 1,367 square feet, in an established part of Winter Garden.
Avoid ifYou need a wide active selection to compare against right now - this is not a high-volume market.

HOA, CDD & Fees

In short
  • Mandatory HOA. Confirm current dues
  • 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.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed OVERSTREET CRATE sales matched to your home.

What is your OVERSTREET CRATE home worth?

Get a no-obligation home value based on real comparable sales in OVERSTREET CRATE, 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 homes for sale in OVERSTREET CRATE on the map →

Real comps, not an automated estimate.

OVERSTREET CRATE Market Scorecard

Strong buyer's market

OVERSTREET CRATE is currently a strong buyer's market. About 12.0 months of supply, a median asking price of $442,500, and homes go under contract in about 22 days.

12.0
Months supply
$442,500
Median list
$275,500
Median sold
$266
Per sqft
22
Days on mkt
2/0/2
Active/Pend/Sold

Go deeper: county scorecard · true cost calculator · affordability calculator.

Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.

Frequently Asked Questions

Is OVERSTREET CRATE a buyer's or seller's market right now?
As of August 2, 2026, OVERSTREET CRATE leans toward buyers: 12.0 months of supply at the current sales pace (Stellar MLS live counts).
How many homes are in OVERSTREET CRATE?
The Florida DOR 2025 assessment roll shows 340 homes plus 21 vacant residential lots in OVERSTREET CRATE (public records).
What share of OVERSTREET CRATE is owner-occupied?
51% of OVERSTREET CRATE parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in OVERSTREET CRATE built?
Homes in OVERSTREET CRATE were built between 1909 and 2024, with a median year built of 1959 (FL DOR 2025 roll).
Do cash buyers compete in OVERSTREET CRATE?
Cash buyers took 25% of OVERSTREET CRATE sales in the 12 months ending June 2025 (1 of 4 closings, Stellar MLS).
Who is the best real estate agent for OVERSTREET CRATE?
The best agent for OVERSTREET CRATE is one who actively works WINTER GARDEN and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for OVERSTREET CRATE.
How do I find a top WINTER GARDEN real estate agent who knows OVERSTREET CRATE?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows OVERSTREET CRATE and the wider WINTER GARDEN area.
Can Momentum Realty connect me with an agent for OVERSTREET CRATE?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your OVERSTREET CRATE purchase or sale - no call center and no pressure.
Buyers focused on Winter Garden who are flexible on home age and willing to evaluate condition property by property.Excellent fit
Buyers comfortable moving quickly when one of the few active listings matches their needs.Excellent fit
Sellers with a home in solid, updated condition who can stand out in a market with very few competing listings.Excellent fit
Buyers who want to compare several active listings side by side before deciding.Probably not
Buyers seeking a home with established community amenities, since none are currently identified from MLS data.Probably not
Sellers expecting a fast, high-volume sale process given the current 12-month supply.Probably not

Nearby Communities

Explore more neighborhoods near OVERSTREET CRATE with Momentum Realty’s local guides.

Bay St Park Winter Garden0.3 mi awayJoe Louis Park First Add Winter Garden0.4 mi awayLoveless J S Add 01 Winter Garden0.5 mi awayMerchants Sub Winter Garden0.5 mi awayJSJ S Loveless Add Winter Garden0.6 mi awayEast Garden Manor Add 03 Winter Garden0.7 mi awayMJMary Jean Sub Winter Garden0.7 mi awayHeritage Plant Street Winter Garden0.9 mi away

Browse all Florida neighborhood guides →

Data sources & freshness

Live listingsStellar MLS, refreshed twice daily (last: August 2, 2026)
Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (6 streets, ZIP 34787))
Under-contract sharesStellar MLS records, as of 2026-08-01
Historical depthClosed-sale records back to 2015 (21 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 your area comps.

Looking to buy here? Search homes for sale →

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CallFree valuation →
Thinking of selling in OVERSTREET CRATE? 1 recorded closings (window ending 2026-08-02). See the Orange County sell-now-or-wait data, what made 201,552 Florida listings fail in the last 12 months, or compare a cash offer vs. listing. Compiled from MLS records; deemed reliable but not guaranteed.
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