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Hillcrest in Winter Garden

Hillcrest
Homes for Sale in Winter Garden, FL

By , Co-Founder, Momentum Realty · Updated October 24, 2026

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All 749 homes for sale in Winter Garden, FL · median $589,900 · 706 homes for sale in 34787 · Orange County homes for sale

Community in Winter Garden · Orange County · ZIP 34787
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True comps, carrying-cost math, and listings before the portals.

Built fromLive Stellar MLS data10 years of closingsUpdated twice daily

As of October 2026, Hillcrest in Winter Garden, FL has 1 home for sale. As of October 2026, the MLS records 2 closed sales in Hillcrest in Winter Garden, FL since 2016, the most recent in July 2021. Across Winter Garden as a whole, 1,339 homes closed in the last 12 months at a median of $595,000, 38 median days on market, with 694 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $9,920 ($9,250 with the full homestead exemption).

Live · Hillcrest Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Tempo
0%
Under contract
Orange: 26% (2,054 of 7,927)
1 · 0
For sale · pending
live counts, refreshed twice daily
Track record · 10 years of records
2
Failed listings · 2026
peaked at 2 in 2008
The Area Market

The market around Hillcrest

Hillcrest is a small community — 6 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 Hillcrest specifically. Momentum Research analysis of MLS records.

The Strategy

The Hillcrest buying strategy.

If we were buying in Hillcrest 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 Hillcrest.

“

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

Jon Brooks · Founder, Momentum Realty

HOA, CDD & Fees

A note on who we are: Momentum Realty is a real estate brokerage. We are not the Hillcrest 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 Hillcrest.
In short
  • 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.

Run Your Numbers

Tools for a Hillcrest buy.

Free calculators to pressure-test the real cost before you tour.

Mortgage paymentPrincipal, interest, taxes, and insurance on a specific price.Property taxOrange County millage and the homestead picture.Rent vs buyThe breakeven on owning in Hillcrest.Save Our HomesProject your homestead tax cap over time.
The takeaway

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

Selling in Hillcrest

Price it to the comps and condition, not an automated estimate.

If you are thinking about selling in Hillcrest, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.

What is your Hillcrest home worth?

Get a no-obligation home value based on real comparable sales in Hillcrest, 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 Hillcrest on the map →

Real comps, not an automated estimate.

Data sources & freshness

Live listingsStellar MLS, refreshed twice daily (last: October 19, 2026)
Under-contract sharesStellar MLS records, as of 2026-08-01
Historical depthClosed-sale records back to 2016 (2 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 →

What’s your home worth in your area?

A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.

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Email me new listings in HillcrestHomes for Sale

One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.

Equal Housing Opportunity. Every community is open to everyone; alerts are about homes, never about who lives here.

Ask an agent about HillcrestHomes for Sale

Have a question about the homes, fees, rules or commute here? A Momentum agent who works HillcrestHomes for Sale will answer, and the answer is published on this page for the next buyer.

Property facts only: homes, fees, rules, commute. Every community is open to everyone; agents do not answer questions about who lives here.

Common questions about Hillcrest

Where is Hillcrest?

Hillcrest is a community in Winter Garden, Orange County, Florida, ZIP 34787.

Are there homes for sale in Hillcrest right now?

Yes - 1 active and 0 pending listings as of the last feed refresh (twice daily). They are listed on this page.

Does Hillcrest have an HOA or CDD?

No HOA is on record for Hillcrest 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 Hillcrest with Momentum Realty’s local guides.

MWMagnolia Wood0.1 mi away · 139 homes, built 1943–23FLFullers Landing B0.2 mi away · 62 homes, built 2005–06MWMagnolia Woods0.2 mi away · 23 homes, built 1958–02Teacup Springs Cove0.2 mi away · 9 homes, built 1994–04, 1 for saleCrown Point Springs0.3 mi away · median $530K, 3 sales/12 moGlenview Estates0.3 mi away

Browse all neighborhood guides →

Talk to a Local Hillcrest Expert
Call Get Listings

The real cost & risk here

Before the list price, the Florida math the portals skip. These are Orange County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.

$2,571/mo
Orange County typical true cost to own
$117/mo
Orange County typical home insurance
Check CDD
Confirm before you offer

Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Orange County scorecard.

County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.

HILLCREST Market Scorecard

No active listings

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

n/a
Months supply
n/a
Median list
$1,350,000
Median sold
n/a
Per sqft
n/a
Days on mkt
0/0/1
Active/Pend/Sold

Typical home value in the 34787 ZIP is $574,696, right around the Florida norm (Zillow Home Value Index).

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

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