Hillcrest
Homes for Sale in Winter Garden, FL
All 720 homes for sale in WINTER GARDEN, FL · median $575,000 · 509 homes for sale in 34787 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, Hillcrest in Winter Garden, FL has 1 home for sale. As of September 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, 1,316 homes closed in the last 12 months at a median of $595,000, 38 median days on market, with 348 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).
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 Hillcrest buying strategy.
If we were buying in Hillcrest 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 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.
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 Hillcrest 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 Hillcrest sales matched to your home.
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 →
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-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.
See how HILLCREST fits the bigger picture — live prices, inventory, and Momentum Scores:
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.
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.
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
HILLCREST is currently a no active listings market. Limited supply, a median asking price of n/a.
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.