Winding Hollow Winter Springs
Homes for Sale in WINTER SPRINGS, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
Winding Hollow Winter Springs right now
🔴 Seller-leaning market. 1.0 months of supply and 80% of the inventory already under contract give sellers the pressure advantage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of July 15, 2026. Confidence: High (5 active and pending listings, 12 closed sales in 12 months).
🟡 Still climbing. The trailing-12-month median ($600K) is up 1.7% from the prior 12 months ($590K) and up 108% since 2012. With about 7 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 15. Confidence: Medium (12 and 9 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated July 15, 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
Winding Hollow Winter Springs market snapshot (as of July 15, 2026): the median sale price is about $600K ($238 per sq ft over the trailing 12 months of closed sales), a median 17 days on market for closed sales, and 1.0 months of supply, a seller-leaning market. The trailing-12-month median is up 2% from the prior 12 months and up 108% since 2012, computed from record-level Stellar MLS closed sales (12 closings in the current window).
Winding Hollow Winter Springs is a community of 296 homes in WINTER SPRINGS, Seminole County, built between 1995 and 2000 (median 1998), with a median living area of about 2,374 square feet. 92% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of Winding Hollow Winter Springs. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Winding Hollow Winter Springs
Winding Hollow Winter Springs
Winding Hollow Winter Springs
Winding Hollow Winter Springs
Winding Hollow Winter Springs
Winding Hollow Winter SpringsPrice History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending July 15 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($600K) IS the median in the snapshot above, and the move from 2025 ($590K) IS the +1.7% one-year change.
Windows contain 0 to 22 sales each (12 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.
WINDING HOLLOW Market Scorecard
WINDING HOLLOW is currently a strong seller's market. About 1.8 months of supply, a median asking price of $660,000, and homes go under contract in about 4 days.
Go deeper: 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.
Housing distress & ownership in Winding Hollow Winter Springs, WINTER SPRINGS
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 August 2026 through August 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in Winding Hollow Winter Springs
Live MLS inventory for Winding Hollow Winter Springs. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Winding Hollow Winter Springs listings as of 2026-08-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period %s through %s. Tap any home to ask about it.
Winding Hollow Winter Springs on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at Winding Hollow Winter Springs
- Playground · reported on 11 of 14 listings
- Deed Restrictions · reported on 5 of 14 listings
- Park · reported on 4 of 14 listings
- Fence Restrictions · reported on 1 of 14 listings
- Dog Park · reported on 1 of 14 listings
- Basketball Court · reported on 1 of 14 listings
- Association Recreation - Owned · reported on 1 of 14 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Seminole County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Layer Elementary · Elementary
- Indian Trails Middle · Middle
- Winter Springs High · High
Zoned schools reflect the assignments reported on recent Winding Hollow Winter Springs listings and can change; always confirm with Seminole County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Winding Hollow Winter Springs address.
The Winding Hollow Winter Springs buying strategy.
If we were buying in Winding Hollow Winter Springs 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.
Come strong and clean. Homes here move, so lead with your best terms and financing ready rather than a low anchor.
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 Winding Hollow Winter Springs.
A closer look at the Winding Hollow Winter Springs market
At a median of $238 per square foot, Winding Hollow Winter Springs prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 1.0 months of supply, a seller-leaning market and the trailing-12-month median up 2% year over year. Homes that do trade take a median 17 days on market, useful leverage on any listing that has lingered.
The housing stock is 296 homes built between 1995 and 2000, and 92% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in Winding Hollow Winter Springs. 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 Winding Hollow Winter Springs 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 5 factors (8.1). Basis: Long-Term Appreciation +108% since 2012; Recent Direction +1.7% year-over-year; Liquidity & Demand 1.0 months of supply; Owner Commitment 92% owner-occupied; Pricing Power 97.5% sale-to-list. Refreshed with each data update.
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 Winding Hollow Winter Springs 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 Winding Hollow Winter Springs sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winding Hollow Winter Springs, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Winding Hollow Winter Springs home worth?
Get a no-obligation home value based on real comparable sales in Winding Hollow Winter Springs, 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 Winding Hollow Winter Springs on the map →
Frequently Asked Questions
What is the median home price in Winding Hollow Winter Springs?
How long do homes in Winding Hollow Winter Springs take to sell?
Is Winding Hollow Winter Springs a buyer's or seller's market right now?
How many homes are in Winding Hollow Winter Springs?
What share of Winding Hollow Winter Springs is owner-occupied?
When were the homes in Winding Hollow Winter Springs built?
Do cash buyers compete in Winding Hollow Winter Springs?
Have Winding Hollow Winter Springs home prices gone up?
Who is the best real estate agent for Winding Hollow Winter Springs?
How do I find a top WINTER SPRINGS real estate agent who knows Winding Hollow Winter Springs?
Can Momentum Realty connect me with an agent for Winding Hollow Winter Springs?
Nearby Communities
Explore more neighborhoods near Winding Hollow Winter Springs with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: July 16, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending July 15, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (community parcel extract) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2005 (137 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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