OAK PARK AT WINTER GARDEN
Homes for Sale in WINTER GARDEN, FL

Community in WINTER GARDEN · Orange County · ZIP 34787
43 homesBuilt 1997–1999
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Built fromLive Stellar MLS data18 years of closingsFL DOR public recordsUpdated twice daily
Live · OAK PARK AT WINTER GARDEN Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Tempo
2
Sold · last 12 mo
10-yr average: about 1 a year
Ownership and context
74%
Owner-occupied · OAK PARK AT WINTER GARDEN
32 of 43 parcels homesteaded (FL DOR 2025)
26%
Non-owner-occupied · OAK PARK AT WINTER GARDEN
incl. 5% trust or LLC-held · 100% out-of-state
33%
Cash buyers · OAK PARK AT WINTER GARDEN
1 of 3 sales, 12 mo ending June 2026
43
Homes in the community
43 residential parcels (FL DOR 2025)
Track record · 18 years of records
Est. 1997
Community established
homes built 1997-1999, median 1998 (FL DOR 2025)
1
Failed listings · 2026
peaked at 2 in 2007
4.7%/yr
Turnover rate
about 2 of 43 homes trade a year
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Oak Park At Winter Garden is a small, tightly built pocket of 43 homes, all raised between 1997 and 1999, with a median year built of 1998. That narrow construction window means buyers are shopping a consistent product line rather than a mix of eras, so the differentiators come down to updates, lot position, and condition rather than age.

A median of just 6 days on market and a closings window of 3 tell you this is a fast-moving pocket right now — homes that are priced and presented correctly are not sitting. With a median price of $482,500 against a median living area of 1,476 square feet, per-square-foot value (median $381.72) is the number to watch, since it will vary more with finish level and lot than with floor plan here.

The 60-Second Overview

A compact, single-era community in Winter Garden where nearly three-quarters of homes (74.4%) are owner-occupied under homestead exemption, pointing to a market with limited turnover and a base of long-tenured owners rather than frequent resale churn.

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 who want a home built within a known, narrow construction window (1997-1999) rather than a mixed-age subdivision.
  • Buyers comfortable moving quickly on a listing, given a recent median of just 6 days on market.
  • Buyers targeting a living area near 1,476 square feet at a price point near the community's $482,500 median.

Probably not for

  • Buyers who want confirmed on-site community amenities before writing an offer, since none are currently identified from MLS data.
  • Buyers who prefer browsing a large pool of active listings before deciding, given the community's limited size of 43 homes.
  • Buyers hoping to negotiate a long due-diligence timeline in a market currently moving at a median of 6 days.

The market around OAK PARK AT WINTER GARDEN

OAK PARK AT WINTER GARDEN is a small community — 8 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).

Homes here are single family residence.

ZIP and county figures describe the wider market, not OAK PARK AT WINTER GARDEN specifically. Momentum Research analysis of MLS records.

If we were buying in OAK PARK AT WINTER GARDEN 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

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

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 OAK PARK AT WINTER GARDEN.

Best Buy
Buyers who want a consistent, single-era home base in Winter Garden without shopping across decades of construction styles.
Biggest Risk
Thin inventory (just 43 homes) means limited selection at any given moment.
Sweet Spot
Buyers focused on move-in condition homes near the community's established $482,500 median price point.
Avoid If
You need to compare many active listings side by side or want community amenities confirmed before you shop — neither is guaranteed here.

A small, consistent pocket with limited current listings

With only 43 homes in the community and a homestead share of 74.4%, inventory here is inherently thin — this is not a subdivision where dozens of comparable listings hit the market at once. Buyers should expect to move decisively when something in their range and condition preference appears, since the recent median of 6 days on market suggests limited time to deliberate once a listing goes active.

Current MLS data does not identify specific community amenities, so any recreational features, common areas, or HOA-maintained facilities should be confirmed directly rather than assumed. Pricing should be evaluated on a per-home basis: with homes built within a tight 1997-1999 window, the spread in value is more likely driven by renovation level, lot specifics, and finish quality than by structural age differences.

The location and the amenities are priced into every listing in OAK PARK AT WINTER GARDEN. 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 community this small, with only 43 homes and a fast median timeline of 6 days, missing a listing by a day can mean missing it entirely. We track this pocket closely enough to flag new listings and shifts in condition-driven pricing before they become common knowledge, and we help you verify amenity and HOA details directly rather than relying on assumptions.

OAK PARK AT WINTER GARDEN in 15 seconds.

Best forBuyers who want a consistent, single-era home base in Winter Garden without shopping across decades of construction styles.
Biggest advantageA tight, fast-moving market where well-presented homes do not linger.
Biggest riskThin inventory (just 43 homes) means limited selection at any given moment.
Sweet spotBuyers focused on move-in condition homes near the community's established $482,500 median price point.
Avoid ifYou need to compare many active listings side by side or want community amenities confirmed before you shop — neither is guaranteed here.

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 OAK PARK AT WINTER GARDEN sales matched to your home.

What is your OAK PARK AT WINTER GARDEN home worth?

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Real comps, not an automated estimate.

Frequently Asked Questions

How many homes are in OAK PARK AT WINTER GARDEN?
The Florida DOR 2025 assessment roll shows 43 homes in OAK PARK AT WINTER GARDEN (public records).
What share of OAK PARK AT WINTER GARDEN is owner-occupied?
74% of OAK PARK AT WINTER GARDEN parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in OAK PARK AT WINTER GARDEN built?
Homes in OAK PARK AT WINTER GARDEN were built between 1997 and 1999, with a median year built of 1998 (FL DOR 2025 roll).
Do cash buyers compete in OAK PARK AT WINTER GARDEN?
Cash buyers took 33% of OAK PARK AT WINTER GARDEN sales in the 12 months ending June 2026 (1 of 3 closings, Stellar MLS).
Who is the best real estate agent for OAK PARK AT WINTER GARDEN?
The best agent for OAK PARK AT WINTER GARDEN 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 OAK PARK AT WINTER GARDEN.
How do I find a top WINTER GARDEN real estate agent who knows OAK PARK AT WINTER GARDEN?
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 OAK PARK AT WINTER GARDEN and the wider WINTER GARDEN area.
Can Momentum Realty connect me with an agent for OAK PARK AT WINTER GARDEN?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your OAK PARK AT WINTER GARDEN purchase or sale - no call center and no pressure.
Buyers who want a home built within a known, narrow construction window (1997-1999) rather than a mixed-age subdivision.Excellent fit
Buyers comfortable moving quickly on a listing, given a recent median of just 6 days on market.Excellent fit
Buyers targeting a living area near 1,476 square feet at a price point near the community's $482,500 median.Excellent fit
Buyers who want confirmed on-site community amenities before writing an offer, since none are currently identified from MLS data.Probably not
Buyers who prefer browsing a large pool of active listings before deciding, given the community's limited size of 43 homes.Probably not
Buyers hoping to negotiate a long due-diligence timeline in a market currently moving at a median of 6 days.Probably not

Data sources & freshness

Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (3 streets, ZIP 34787))
Under-contract sharesStellar MLS records, as of 2026-08-01
Historical depthClosed-sale records back to 2008 (16 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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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.

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Thinking of selling in OAK PARK AT WINTER GARDEN? 2 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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