Bennington
Homes for Sale in Winter Park, FL
All 361 homes for sale in Winter Park, FL · median $695,000 · 82 homes for sale in 32792 · Seminole County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, the MLS records 10 closed sales in Bennington in Winter Park, FL since 2007, the most recent in August 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).
Bennington is a small Winter Park address sitting in Seminole County, and with a snapshot this lean, the honest move is to treat price here as condition-driven rather than sticker-driven. What separates one sale from the next is the state of the home itself — updates, systems, and lot position — far more than any published range, because there isn't one worth quoting.
For a buyer, that means underwriting each listing on its own merits and not assuming the last sale sets your number. For a seller, it means condition and presentation are doing the heavy lifting; a well-prepared home tends to define the top of what this pocket will pay, and a tired one gets discounted quickly.
Nearby homes for sale
No active listings inside BenningtonHomes 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.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Bennington is a compact community in Winter Park's Seminole County footprint, which keeps it close to the amenities and connectivity of the broader Winter Park area while remaining small enough that inventory turns over quietly.
Stellar MLS sales records identify 12 homes in Bennington that have changed hands since 2011, built between 2002 and 2003 (median 2003), with a median living area of about 2,000 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 Bennington is best for.
Best for
- Buyers set on a Winter Park address who value a small, low-turnover pocket
- Buyers willing to underwrite a home on its own condition rather than a market range
- Buyers who want to lean on the wider area's amenities rather than an internal amenity set
Probably not for
- Buyers who need a large amenity package inside the community itself
- Buyers who want deep comp data and frequent recent sales to anchor a price
- Buyers shopping a strict published price range rather than pricing by condition
The market around Bennington
Bennington 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 Bennington specifically. Momentum Research analysis of MLS records.
The Bennington buying strategy.
If we were buying in Bennington 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 Bennington.
A small pocket in a well-known name
Buying in a limited community like Bennington is different from shopping a large master-planned tract. With fewer homes trading, comparisons are thinner and each individual sale carries more weight, so getting the pricing and inspection work right matters more than usual.
Location does a lot of the talking here. Sitting inside Winter Park's Seminole County reach, Bennington leans on the surrounding area's roads, retail, and services rather than a large internal amenity set. Judge the home and its immediate setting first; the address handles the rest.
The location and the amenities are priced into every listing in Bennington. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a thin, condition-driven pocket like Bennington, the difference between a fair deal and an overpay comes down to reading each home on its own terms. We price and negotiate off the specifics in front of us — systems, updates, and lot — instead of leaning on a range that doesn't exist, and we'll tell you plainly when a listing doesn't justify its number.
Bennington in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $35/month (about $420/yr) · median of 3 MLS listings, most billed annually
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $35 per month ($420 a year) — the median AssociationFee across 3 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 Bennington 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 Bennington sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Bennington, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Bennington home worth?
Get a no-obligation home value based on real comparable sales in Bennington, 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 →
Should you buy in Bennington?
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: September 15, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2007 (10 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.
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Common questions about Bennington
Where is Bennington?
Bennington is a community in Winter Park, Seminole County, Florida, ZIP 32792.
Are there homes for sale in Bennington right now?
No active listings inside Bennington at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Bennington have an HOA or CDD?
No HOA is on record for Bennington 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 Bennington with Momentum Realty’s local guides.
Bennington Market Scorecard
Bennington is currently a no active listings market. Limited supply, a median asking price of n/a.
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.