Winterbrook
Homes for Sale in Winter Park, FL

All 356 homes for sale in Winter Park, FL · median $697,000 · 124 homes for sale in 32792 · Seminole County homes for sale

Community in Winter Park · Seminole County · ZIP 32792
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True comps, carrying-cost math, and listings before the portals.

Built fromLive Stellar MLS data6 years of closingsUpdated twice daily

As of October 2026, the MLS records 5 closed sales in Winterbrook in Winter Park, FL since 2020, the most recent in October 2025. Across Winter Park as a whole, 494 homes closed in the last 12 months at a median of $449,000, 33 median days on market, with 128 homes for sale today. At that median and Seminole County's FY2025-26 rate of 15.18 mills, annual property tax runs about $6,820 ($6,220 with the full homestead exemption).

Live · Winterbrook Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Tempo
0 · 0
For sale · pending
live counts, refreshed twice daily
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Winterbrook does not have an active pricing story to tell right now. There is no meaningful volume in the current Stellar MLS feed for this Winter Park pocket of Seminole County, which means we are not going to manufacture a median, a days-on-market figure, or a trend line that does not exist. Anyone telling you otherwise for this specific community is guessing.

That thin data picture is itself useful information for a buyer or seller. It usually means one of two things: the community is small and turns over rarely, or listings here get grouped under a broader area name in the MLS. Either way, the right move is a direct pull of whatever is currently listed or has recently closed, not a reliance on aggregated stats that do not actually reflect Winterbrook.

Nearby homes for sale

No active listings inside WinterbrookHomes for Sale in Winter Park, 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.

2008 HOUNDSLAKE DRIVE
$475K · 0.2 mi away
4 bd · 2 ba · 2,250 sqft
2008 HOUNDSLAKE DRIVE
Listed by MARK SPAIN REAL ESTATE
5405 JUSTINE WAY
$400K · 0.3 mi away
3 bd · 2 ba · 1,247 sqft
5405 JUSTINE WAY
Listed by LPT REALTY, LLC
3020 NICHOLSON DRIVE
$495K · 0.4 mi away
4 bd · 2 ba · 1,756 sqft
3020 NICHOLSON DRIVE
Listed by CHARLES RUTENBERG REALTY ORLANDO
5303 PINE LILY CIRCLE
$659K · 0.7 mi away
3 bd · 2 ba · 2,265 sqft
5303 PINE LILY CIRCLE
Listed by PM ELITE REALTY LLC
1117 WADING WATERS CIRCLE
$1.32M · 0.7 mi away
6 bd · 4 ba · 4,307 sqft
1117 WADING WATERS CIRCLE
Listed by THE AGENCY FL
5334 LANYARD COURT
$480K · 0.7 mi away
3 bd · 2 ba · 1,561 sqft
5334 LANYARD COURT
Listed by BHHS FLORIDA REALTY

Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.

The 60-Second Overview

Winterbrook sits in Winter Park, Seminole County, an area where nearby communities carry more MLS history than this one does at present. No community amenities are identified in current listings, so any pool, clubhouse, or recreational feature would need to be confirmed at the individual property level.

Stellar MLS sales records identify 10 homes in Winterbrook that have changed hands since 2020, built between 2020 and 2021 (median 2020), with a median living area of about 2,164 sq ft and a typical 4-bedroom, 2.5-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.

Best for

  • A buyer who already has a specific Winterbrook property in mind and wants direct, verified due diligence rather than market averages
  • A seller comfortable pulling comps from nearby, better-documented Winter Park communities with careful adjustment
  • Someone prioritizing the Winter Park, Seminole County location itself over a specific slate of on-site amenities

Probably not for

  • A buyer who wants to compare median price and days-on-market trends before narrowing a search
  • Someone shopping primarily for a specific listed amenity, such as a clubhouse or pool, without independent confirmation
  • A seller who needs a same-community comp set to support pricing strategy

The market around Winterbrook

Winterbrook is too small for its own price trend, so here is the market around it.

In ZIP 32792, 137 homes are on the market and 21% are under contract — a steady corner of Winter Park.

Across Seminole County, 1,646 homes are active and 585 pending (26% under contract).

In ZIP 32792 (Winter Park), 617 homes closed in the last 12 months at a median of $408K ($256/sq ft), down 1.9% year over year, with a median 28 days on market. Right now 49 active and 13 pending listings put supply at about 3.4 months — a balanced market. See the live ZIP 32792 housing market and the Orange County market.

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

If we were buying in Winterbrook 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 Winterbrook.

Best Buy
Best for a buyer or seller who wants a direct, verified read on a specific Winterbrook property rather than a community-wide market summary.
Biggest Risk
The risk is data scarcity - with no current pricing or amenity statistics, you are relying on individual property verification rather than trend data.
Sweet Spot
The sweet spot is a buyer targeting a specific address in Winterbrook who is prepared to verify HOA status and amenities directly rather than lean on aggregated stats.
Avoid If
Avoid if you need robust comparable data before committing - that data does not currently exist for this community in isolation.

What the data gap actually means

When a community shows no current MLS amenity data and no reliable price statistics, it is tempting to fill in the blanks with assumptions borrowed from the surrounding Winter Park market. We do not do that. A community with this little current listing activity could mean very low turnover, a naming quirk in how the MLS tags the subdivision, or simply a quiet stretch with nothing on the market as of this snapshot.

For a buyer, that means going in with fewer assumptions and more direct verification: pull the plat, check the HOA (if one exists) directly, and treat any amenity claim from a listing agent as something to confirm rather than take at face value. For a seller, it means your comps may need to be pulled from adjacent, better-documented communities and adjusted carefully, since Winterbrook itself will not generate a clean, defensible dataset on its own.

“

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

Jon Brooks · Founder, Momentum Realty

Why work with Momentum here

This is exactly the kind of community where a broker's local footwork matters more than a dashboard. We do not have a stat sheet to hand you for Winterbrook, so instead we pull public records, check for an active HOA, and verify amenities and recent activity property by property before you make a decision either way.

Winterbrook in 15 seconds.

Best forBest for a buyer or seller who wants a direct, verified read on a specific Winterbrook property rather than a community-wide market summary.
Biggest advantageThe advantage here is low competition for information - little current MLS noise means less second-guessing from other buyers working off the same data.
Biggest riskThe risk is data scarcity - with no current pricing or amenity statistics, you are relying on individual property verification rather than trend data.
Sweet spotThe sweet spot is a buyer targeting a specific address in Winterbrook who is prepared to verify HOA status and amenities directly rather than lean on aggregated stats.
Avoid ifAvoid if you need robust comparable data before committing - that data does not currently exist for this community in isolation.

HOA, CDD & Fees

A note on who we are: Momentum Realty is a real estate brokerage. We are not the Winterbrook homeowners association, its management company or its developer, and we cannot help with dues, gate access, violations, amenity bookings or association documents. To reach the association, check your closing package, the recorded declaration at the county clerk, or search the association’s name at sunbiz.org for its registered agent. Call or message us to buy or sell a home in Winterbrook.
In short
  • HOA dues reported around $230/month (about $2,760/yr) · median of 22 MLS listings, most billed monthly
  • Any club/amenity membership is billed separately

Listings in this community report association dues of about $230 per month ($2,760 a year) — the median AssociationFee across 22 MLS records, normalised to a monthly figure; most are billed monthly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-10.

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 Winterbrook sales matched to your home.

What is your Winterbrook home worth?

Get a no-obligation home value based on real comparable sales in Winterbrook, 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 Park →

Real comps, not an automated estimate.
A buyer who already has a specific Winterbrook property in mind and wants direct, verified due diligence rather than market averagesExcellent fit
A seller comfortable pulling comps from nearby, better-documented Winter Park communities with careful adjustmentExcellent fit
Someone prioritizing the Winter Park, Seminole County location itself over a specific slate of on-site amenitiesExcellent fit
A buyer who wants to compare median price and days-on-market trends before narrowing a searchProbably not
Someone shopping primarily for a specific listed amenity, such as a clubhouse or pool, without independent confirmationProbably not
A seller who needs a same-community comp set to support pricing strategyProbably not

Data sources & freshness

Live listingsStellar MLS, refreshed twice daily (last: September 19, 2026)
Under-contract sharesStellar MLS records, as of 2026-09-08
Historical depthClosed-sale records back to 2020 (5 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.

Looking to buy here? Search homes for sale →

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Common questions about Winterbrook

Where is Winterbrook?

Winterbrook is a community in Winter Park, Seminole County, Florida, ZIP 32792.

Are there homes for sale in Winterbrook right now?

No active listings inside Winterbrook at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.

Does Winterbrook have an HOA or CDD?

No HOA is on record for Winterbrook in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.

Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.

Nearby Communities

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

WWrenwood0.2 mi away · 190 homes, built 1975–23Cedar Ridge0.2 mi away · median $340K, 7 sales/12 moHowell Branch Woods0.3 mi away · 235 homes, built 1962–83Country Lane0.3 mi away · median $386K, 14 sales/12 moRReplat0.4 mi away · 8 homes, built 1976–77Lake Florence Preserve0.4 mi away · 29 homes, built 2018–19

Browse all neighborhood guides →

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Winterbrook Market Scorecard

No active listings

Winterbrook is currently a no active listings market. Limited supply, a median asking price of n/a.

n/a
Months supply
n/a
Median list
$730,000
Median sold
n/a
Per sqft
n/a
Days on mkt
0/0/1
Active/Pend/Sold

Typical home value in the 32792 ZIP is $398,663, about 20.6% above the Florida norm (Zillow Home Value Index).

Go deeper: ZIP market scorecard · 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.