Winter Hill
Homes for Sale in Orlando, FL
All 4,065 homes for sale in Orlando, FL · median $380,000 · 214 homes for sale in 32835 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
As of October 2026, the MLS records 16 closed sales in Winter Hill in Orlando, FL since 2006, the most recent in September 2026. Across Orlando as a whole, 6,171 homes closed in the last 12 months at a median of $415,000, 42 median days on market, with 1,694 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $6,920 ($6,250 with the full homestead exemption).
| Location | Orlando, Orange County, FL · ZIP 32835 |
|---|---|
| Homes in the community | 83 (FL DOR 2025 assessment roll) |
| Years built | 1991–2007 (median 1993) |
| Typical living area | 1,954 sq ft (median) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 78% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Winter Hill key facts,” movewithmomentum.com/neighborhoods/winter-hill, data as of September 20, 2026.
Last 30 days in Winter Hill: 1 closed sale (median $325,000). As of October 5, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Winter Hill is a compact, built-out pocket in Orlando where the homes came up in a fairly tight window, from 1991 to 2007, with the median year built landing in 1993. That means what sets price here is not the vintage or the floor plan so much as condition and updates. At a median of just under 2,000 square feet of living space, most of these homes sit in the same size class, so a renovated interior separates itself from a dated one far more than square footage does.
With only 83 homes in the community and a homestead share near 78 percent, turnover is thin and most owners are living in what they own rather than renting it out. For a seller, that scarcity is leverage when a home shows well. For a buyer, it means you may wait for the right listing rather than choosing from many, and you should be ready to move when a well-kept one surfaces.
Nearby homes for sale
No active listings inside Winter Hill 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.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Winter Hill is a small, established Orange County community of 83 homes built in a compact early-1990s-to-2000s window, where day-to-day pricing is driven far more by condition than by size or age.
Stellar MLS sales records identify 38 homes in Winter Hill that have changed hands since 2004, built between 1991 and 2002 (median 1992), with a median living area of about 1,956 sq ft and a typical 4-bedroom, 2-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.
Who Winter Hill is best for.
Best for
- Buyers targeting a home around 1,954 square feet who value a single, consistent size class
- Owner-occupants planning a long hold in an established community
- Buyers willing to wait for a well-maintained or updated listing rather than settle
Probably not for
- Buyers who need many active listings to compare at once
- Investors seeking a rental-heavy building with high turnover
- Buyers wanting new construction or a broad mix of floor plans and sizes
The market around Winter Hill
Winter Hill is too small for its own price trend, so here is the market around it.
In ZIP 32835, 268 homes are on the market and 17% are under contract — a slower corner of Orlando.
Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).
In ZIP 32835 (Orlando), 367 homes closed in the last 12 months at a median of $290K ($221/sq ft), down 7.6% year over year, with a median 58 days on market. Right now 123 active and 27 pending listings put supply at about 6.2 months — a buyer's market. See the live ZIP 32835 housing market and the Orange County market.
ZIP and county figures describe the wider market, not Winter Hill specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in Winter Hill, Orlando
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
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 October 2026 through October 2026. Deemed reliable but not guaranteed.
The Winter Hill buying strategy.
If we were buying in Winter Hill 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 Winter Hill.
A condition-driven small market
The homes here cluster around a median living area just under 2,000 square feet and a median build year of 1993, so the housing stock is more uniform than most Orlando neighborhoods. When floor plans and footprints are this similar, the spread in what homes actually sell for comes down to the work that has been done inside: kitchens, baths, roofs, systems. Expect a wide gap between a home that has been kept current and one that has not.
The high homestead share, close to 78 percent, tells you this is largely an owner-occupied community rather than an investor block. That tends to correlate with homes that have been maintained for the long haul, but it also means inventory is limited and does not refresh quickly. Anyone shopping Winter Hill should treat it as a patience play, not a browse-and-pick market.
The location and the amenities are priced into every listing in Winter Hill. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community this small, a handful of comparable sales moves the whole conversation, so pricing and negotiation depend on reading condition against the median rather than leaning on volume. We track Winter Hill closely enough to tell a seller which updates actually separate their home from the pack, and to tell a buyer whether a listing's price reflects real work or just a dated interior dressed up.
Winter Hill in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $17/month · median of 44 MLS listings, most billed annually
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $17 per month — the median AssociationFee across 44 MLS records, normalised to a monthly figure; most are billed annually. 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.
Tools for a Winter Hill 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 Winter Hill sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winter Hill, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Winter Hill home worth?
Get a no-obligation home value based on real comparable sales in Winter Hill, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Frequently Asked Questions
How many homes are in Winter Hill?
What share of Winter Hill is owner-occupied?
When were the homes in Winter Hill built?
Who is the best real estate agent for Winter Hill?
How do I find a top Orlando real estate agent who knows Winter Hill?
Can Momentum Realty connect me with an agent for Winter Hill?
Where is Winter Hill, and what county is it in?
Should you buy in Winter Hill?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 4, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (3 streets, ZIP 32835)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2006 (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 local comps.
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Nearby Communities
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