Windward Square Sec 1
Homes for Sale in Winter Park, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
Windward Square Sec 1 is a compact pocket of 198 homes built in a tight window between 1975 and 1980, and that consistency is the story. With a median around 1,236 square feet and a median price of $272,250, you are buying a specific era of construction. What actually moves price here is condition — original versus updated interiors, roof and system age, kitchen and bath work. The spread between a tired house and a renovated one will be wide, so read each listing on its merits rather than the headline median.
The market posture is balanced, not frantic. A median 15 days on market and a heat score of 48 point to steady demand without a bidding-war frenzy, and year-over-year price movement is essentially flat at 0.5%. For buyers, that means room to inspect and negotiate on condition rather than chase. For sellers, it means presentation and pricing to comparable condition matter more than riding a rising tide.
Windward Square Sec 1 right now
🟡 Still climbing. The trailing-12-month median ($272K) is up 0.5% from the prior 12 months ($271K). 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 July 13. Confidence: Medium (9 and 6 sales in the two windows).
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Updated July 13, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Windward Square Sec 1 market snapshot (as of July 13, 2026): the median sale price is about $272K ($244 per sq ft over the trailing 12 months of closed sales), and a median 15 days on market for closed sales. The trailing-12-month median is up 0% from the prior 12 months, computed from record-level Stellar MLS closed sales (9 closings in the current window).
Windward Square Sec 1 is a community of 198 homes in Winter Park, Seminole County, built between 1975 and 1980 (median 1978), with a median living area of about 1,236 square feet. 60% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
This is a small, uniform late-1970s subdivision in Winter Park within Seminole County, where nearly all homes share a similar size and vintage — which makes updates and condition, not floorplan variety, the main differentiator.
Who Windward Square Sec 1 is best for.
Best for
- Buyers targeting a mid-$200s Winter Park entry who value a smaller, low-maintenance footprint
- Renovation-minded buyers willing to update an original home and build equity through the work
- Long-hold buyers who want an established, uniform neighborhood over new construction
Probably not for
- Buyers who need substantially more than the ~1,236-square-foot median living space
- Buyers wanting move-in-ready newer construction with no system or finish updates ahead
- Buyers expecting fast appreciation, given the essentially flat year-over-year movement
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending July 13 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($272K) IS the median in the snapshot above, and the move from 2025 ($271K) IS the +0.5% one-year change.
Windows contain 0 to 9 sales each (9 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 %s through %s. Deemed reliable but not guaranteed.
The Windward Square Sec 1 buying strategy.
If we were buying in Windward Square Sec 1 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 Windward Square Sec 1.
A single-era neighborhood where condition is everything
With every home built between 1975 and 1980 and a median year of 1978, Windward Square Sec 1 offers a predictable envelope: modest single-story footprints near the 1,236-square-foot median, at a median of $244.12 per square foot. Because the bones are so similar across the 198 homes, the value question is almost entirely about what has been done since — roof, HVAC, plumbing, electrical, windows, and interior finishes from an era that often needs attention.
About 60% of homes here carry a homestead exemption, which points to a core of long-term ownership and, generally, fewer listings turning over at once — the closing window reflects a small number of recent sales. That thinner flow means comparable sales require care to interpret, and a single well-renovated or badly-dated sale can skew the read. Work the specifics of each property rather than the averages.
The location and the amenities are priced into every listing in Windward Square Sec 1. 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 Windward Square Sec 1 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 (6.5). Basis: Recent Direction +0.5% year-over-year; Owner Commitment 60% owner-occupied; Pricing Power 96.1% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a small, single-era community, comps are scarce and condition-driven, so a lazy pull of the median tells you almost nothing. We underwrite each home on its actual updates and system ages, weigh the handful of recent closings honestly, and price or negotiate to condition — not to a headline number. That discipline is where deals are won or lost in a neighborhood this uniform.
Windward Square Sec 1 in 15 seconds.
HOA, CDD & Fees
- Mandatory HOA — confirm current dues
- 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 Windward Square Sec 1 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 Windward Square Sec 1 sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windward Square Sec 1, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Windward Square Sec 1 home worth?
Get a no-obligation home value based on real comparable sales in Windward Square Sec 1, 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 Windward Square Sec 1 on the map →
Frequently Asked Questions
What is the median home price in Windward Square Sec 1?
How long do homes in Windward Square Sec 1 take to sell?
How many homes are in Windward Square Sec 1?
What share of Windward Square Sec 1 is owner-occupied?
When were the homes in Windward Square Sec 1 built?
Do cash buyers compete in Windward Square Sec 1?
Who is the best real estate agent for Windward Square Sec 1?
How do I find a top Winter Park real estate agent who knows Windward Square Sec 1?
Can Momentum Realty connect me with an agent for Windward Square Sec 1?
Should you buy in Windward Square Sec 1?
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 July 13, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (6 streets, ZIP 32792)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2005 (51 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 your area comps.
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