Golfside
Homes for Sale in Winter Park, FL
All 404 homes for sale in Winter Park, FL · median $649,000 · 156 homes for sale in 32792 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-08-02, 6 recorded sales closed at a median of $602,500, $292 per square foot, a median 45 days on market, sellers accepting 95% of original asking. At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $10,050 ($9,370 with the full homestead exemption).
Golfside is an established Winter Park pocket where price is driven less by a single formula and more by condition and vintage. With a median build year of 1968 and homes dating from 1956 up through 2023, you are looking at a spread that runs from original mid-century houses to full rebuilds. That range is why the median sits at $660,000 at roughly $307 per square foot on about 2,027 square feet — the number reflects a middle point across very different levels of updating, not a uniform product.
The current posture is patient. A median of 51 days on market says buyers here take their time, and year-over-year pricing is flat at 0.0%, so neither side has a clear upper hand. For sellers, that means condition and honest pricing matter more than momentum. For buyers, it means there is room to be selective and to underwrite each house on its own merits rather than chasing a rising tape.
Figures in this note are as of July 13, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Golfside right now
🔴 Off the recent peak. The trailing-12-month median ($602K) is down 14.5% from the prior 12 months ($705K). With about 3 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: Medium (6 and 7 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated November 8, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Nearby homes for sale
No active listings inside GOLFSIDE SEC 03 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
Golfside market snapshot (as of August 2, 2026): the median sale price is about $602K ($292 per sq ft over the trailing 12 months of closed sales), and a median 46 days on market for closed sales. The trailing-12-month median is down 14% from the prior 12 months, computed from record-level Stellar MLS closed sales (6 closings in the current window).
In ZIP 32792 (Winter Park), 230 homes closed in the last 12 months at a median of $423K ($260/sq ft), down 7.0% year over year, with a median 32 days on market. Right now 11 active and 11 pending listings. See the live ZIP 32792 housing market and the Orange County market.
Golfside is a community of 256 homes in Winter Park, Orange County, built between 1956 and 2023 (median 1971.5), with a median living area of about 2,056 square feet. 81% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
A small, long-settled Winter Park neighborhood of about 153 homes where a homestead share near 80% signals a stable, owner-occupied street rather than a rental-heavy turnover market.
Who Golfside is best for.
Best for
- Long-hold buyers who value a stable, owner-occupied neighborhood over quick turnover
- Renovation-minded buyers willing to update an older home to their own standard
- Buyers targeting a practical, roughly 2,000-square-foot house in an established Winter Park location
Probably not for
- Buyers who need to resell quickly, given a median of 51 days on market
- Anyone expecting near-term price gains, with year-over-year pricing flat at 0.0%
- Buyers who want new construction throughout and no involvement with older systems
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($602K) IS the median in the snapshot above, and the move from 2025 ($705K) IS the -14.5% one-year change.
Windows contain 0 to 7 sales each (6 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2026. Deemed reliable but not guaranteed.
33% of homes for sale in ZIP 32792 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-08-01).
The Golfside buying strategy.
If we were buying in Golfside 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 Golfside.
Vintage, condition, and a thin resale count
The defining variable here is age and what has been done about it. A median year built of 1968 inside a 1956-to-2023 window tells you the housing stock predates most current systems, so the practical question on any given house is how much of it has been renovated. Two homes of similar size can price very differently depending on roof, systems, and kitchens, which is the main reason the median at $660,000 should be read as a midpoint, not a going rate.
Volume is light — only 5 closings in the measured window across 153 homes — so comps are scarce and each new sale carries outsized weight. That thinness cuts both ways: a single well-prepared listing can reset expectations, and a single dated sale can drag the read. Median living space around 2,027 square feet keeps this in solidly practical territory rather than estate scale.
The location and the amenities are priced into every listing in Golfside. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Golfside buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (5.6). Basis: Recent Direction -14.5% year-over-year; Owner Commitment 81% owner-occupied; Pricing Power 94.6% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a neighborhood this small with only a handful of recent closings, the difference between a fair price and a guess is knowing which of those sales was updated and which was original. We walk the specific house, weigh it against the thin comp set, and price to condition instead of to a headline median — the discipline that matters most when there is little data to hide behind.
Golfside in 15 seconds.
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 Golfside 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 Golfside sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Golfside, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Golfside home worth?
Get a no-obligation home value based on real comparable sales in Golfside, 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 Golfside on the map →
| Location | Winter Park, Orange County, FL · ZIP 32792 |
|---|---|
| Homes in the community | 256 (FL DOR 2025 assessment roll) |
| Years built | 1956–2023 (median 1971.5) |
| Typical living area | 2,056 sq ft (median) |
| Sale prices, last 12 months | $602,500 median across 6 closed sales · $292 per sq ft · -14.5% vs the prior 12 months |
| Days on market (closed sales) | 45 median |
| Owner-occupied (homestead) share | 81% |
Data as of August 2, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Golfside key facts,” movewithmomentum.com/neighborhoods/golfside-sec-03, data as of August 2, 2026.
More Winter Park home searches
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- Homes under $300K in Winter Park
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- Winter Park home values: what is my house worth?
- ZIP 32792 housing scorecard
Winter Park guides & data
- Market data
- Cost of living
- Best neighborhoods
- Flood zones
- Property taxes (Orange County)
- Homestead exemption (Orange County)
- Home insurance cost
- New construction
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
- Florida housing market map
- Interactive housing market map (county, ZIP and community)
- Save Our Homes tax estimator
- How to stop a foreclosure in Florida
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Fairway Drive (19 homes on record)
- Golfside Drive (12 homes on record)
- Fairway Drive (10 homes on record)
- Golfside Drive (8 homes on record)
- Summerfield Road (6 homes on record)
- Summerfield Road (4 homes on record)
- Golfside Drive (2 homes on record)
- Fairway Drive (1 homes on record)
- Fairway Drive (1 homes on record)
Email me new listings in Golfside
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.
Ask an agent about Golfside
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Golfside will answer, and the answer is published on this page for the next buyer.
Frequently Asked Questions
What is the median home price in Golfside?
How long do homes in Golfside take to sell?
How many homes are in Golfside?
What share of Golfside is owner-occupied?
When were the homes in Golfside built?
Do cash buyers compete in Golfside?
Who is the best real estate agent for Golfside?
How do I find a top Winter Park real estate agent who knows Golfside?
Can Momentum Realty connect me with an agent for Golfside?
Where is Golfside, and what county is it in?
Is Golfside a good place to live?
Should you buy in Golfside?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (3 streets, ZIP 32792)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2005 (38 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. A Momentum agent can price yours against live local comps.
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More Winter Park & Orlando & Orange County guides
Compare before you commit - every guide covers pricing, HOA/CDD, insurance posture, and fit. Browse all of Orlando & Orange County or the full Neighborhood Finder.
See how GOLFSIDE SEC 03 fits the bigger picture — live prices, inventory, and Momentum Scores: