Windward Square
Homes for Sale in Winter Park, FL
All 337 homes for sale in Winter Park, FL · median $664,900 · Seminole County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 57 closed sales in Windward Square Sec 2 in Winter Park, FL since 2006, the most recent in April 2026. Recorded prices since 2024 ran from $151,000 to $330,000 (median $290,000), on homes of 912 to 1,771 sq ft. Across Winter Park as a whole, 494 homes closed in the last 12 months at a median of $459,450, 34 median days on market, with 124 homes for sale today. At that median and Seminole County's FY2025-26 rate of 15.18 mills, annual property tax runs about $4,400 ($3,800 with the full homestead exemption).
Windward Square is a tight, consistent pocket built out between 1976 and 1980, with a median year built of 1978. That narrow construction window matters more than usual here: buyers aren't weighing decades of style and system differences, they're weighing condition and how each specific owner has maintained a home of roughly the same age and roughly the same footprint, a median of 1,280 square feet.
With 180 homes in the section and no distinguishing community amenities identified from current MLS listings, this is a market where the property itself, not a clubhouse or gate, carries the value conversation. A homestead share of 61.7% tells us a majority of owners are in these homes on a primary-residence basis, which tends to support steadier turnover and fewer flip-driven surprises, but it's not a guarantee of anything about future pricing.
Nearby homes for sale
No active listings inside Windward Square Sec 2 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
A small, single-era section of Winter Park in Seminole County, built almost entirely between 1976 and 1980 with a consistent median living area near 1,280 square feet — a market defined by home condition and age-related maintenance rather than by shared amenities.
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 Windward Square is best for.
Best for
- Buyers focused on a smaller, single-story-era home and comfortable evaluating condition property-by-property.
- Owner-occupant buyers looking for a primary residence rather than a rental or short-term flip, consistent with the section's majority homestead share.
- Buyers who prioritize location and a manageable footprint over amenity packages.
Probably not for
- Buyers who want a newer build with fewer age-related maintenance questions.
- Buyers who expect a gated community, clubhouse, or other shared amenities as part of the purchase.
- Investors seeking a large pool of comparable listings to move on quickly, given the section's limited size and steady owner-occupancy.
The market around Windward Square
Windward Square is a small community — 26 recorded sales on file, most recently in 2026 — too few for its own price trend. Here is the market around it.
Across Seminole County, 1,538 homes are active and 629 pending (29% under contract).
The housing mix here is 78% townhouse, 10% villa, 6% condominium.
ZIP and county figures describe the wider market, not Windward Square specifically. Momentum Research analysis of MLS records.
The Windward Square buying strategy.
If we were buying in Windward Square 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.
One decade, one footprint, one variable
There isn't much spread to explain here. Every home in Windward Square was built within a four-year window, and the median size sits around 1,280 square feet — so the usual real estate questions about 'which era' or 'how big' mostly answer themselves. What's left to evaluate is the individual home: roofing, systems, kitchen and bath updates, and how a given owner has treated a now nearly fifty-year-old structure.
No community amenities were identified from current MLS listings, so this isn't a section where buyers are paying for a pool, gate, or clubhouse. The homestead share of 61.7% suggests the section leans toward owner-occupancy rather than heavy investor or rental turnover, which typically means listings come to market on the owner's timeline rather than in bulk, and buyers should expect to evaluate each home on its own maintenance history rather than assume uniform condition across the section.
The location and the amenities are priced into every listing in Windward Square. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a section this uniform in age and size, the differentiator is almost always condition and update history rather than location or floor plan. We walk each listing against that same 1976-1980 baseline, so you know whether you're looking at a home that's been kept current or one where deferred maintenance is priced in — and we help you price and negotiate accordingly on both the buy and sell side.
Windward Square 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 Windward Square 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 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, 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 home worth?
Get a no-obligation home value based on real comparable sales in Windward Square, 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 Windward Square?
What share of Windward Square is owner-occupied?
When were the homes in Windward Square built?
Do cash buyers compete in Windward Square?
Who is the best real estate agent for Windward Square?
How do I find a top Winter Park real estate agent who knows Windward Square?
Can Momentum Realty connect me with an agent for Windward Square?
Should you buy in Windward Square?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Housing stock & ownership | Florida DOR assessment roll (street-list match (6 streets, ZIP 32707/32792)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2006 (57 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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