Winding Hollow
Homes for Sale in Winter Springs, FL
All 126 homes for sale in WINTER SPRINGS, FL · median $422,445 · 62 homes for sale in 32708 · Seminole County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
Over the 12 months ending 2026-08-02, 11 recorded sales closed at a median of $600,000, $241 per square foot, a median 21 days on market, sellers accepting 97% of original asking (-1% versus the prior year). At the median price and Seminole County's FY2025-26 rate of 15.18 mills, annual property tax runs about $9,110 ($8,510 with the full homestead exemption).
Winding Hollow is a built-out pocket of 161 homes in Winter Springs, with construction running from 1995 to 2000 and a median build year of 1999. At a median of roughly 2,529 square feet, these are substantial homes, and with the neighborhood fully established, price here is driven less by lot premiums or new-build competition and more by condition and updates. A home that has had its kitchen, baths, roof, and systems addressed will separate itself from one still wearing its original late-1990s finishes.
A homestead share above 90% tells you this is a long-hold, owner-occupied street rather than an investor churn. That usually means tighter, less frequent supply. With so few homes turning over in the current window, a seller with a genuinely updated home has leverage, and a buyer should be prepared to move decisively and to underwrite renovation cost honestly on anything that has not been touched in years.
Winding Hollow right now
🟡 Off the recent peak. The trailing-12-month median ($600K) is down 0.8% from the prior 12 months ($605K) and up 115% 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 August 2. Confidence: Medium (11 and 9 sales in the two windows).
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· Updated September 15, 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 WINDING HOLLOW UNIT 5 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
Winding Hollow market snapshot (as of August 2, 2026): the median sale price is about $600K ($241 per sq ft over the trailing 12 months of closed sales), and a median 21 days on market for closed sales. The trailing-12-month median is down 1% from the prior 12 months and up 115% since 2012, computed from record-level Stellar MLS closed sales (11 closings in the current window).
In ZIP 32708 (WINTER SPRINGS), 668 homes closed in the last 12 months at a median of $412K ($242/sq ft), down 1.5% year over year, with a median 33 days on market. Right now 32 active and 21 pending listings put supply at about 1.9 months — a healthy market. See the live ZIP 32708 housing market and the Seminole County market.
Winding Hollow is a community of 387 homes in Winter Springs, Seminole County, built between 1994 and 2000 (median 1997), 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).
This is a mature, owner-occupied enclave of larger single-family homes from the late 1990s in Winter Springs, where the spread in asking prices reflects how much work each house has or hasn't had, not differences in the neighborhood itself.
Who Winding Hollow is best for.
Best for
- Long-term owner-occupants wanting space in the 2,500-square-foot range and willing to hold
- Buyers comfortable budgeting for updates on a home built in the late 1990s
- Purchasers who value an established, low-churn neighborhood over a brand-new subdivision
Probably not for
- Buyers set on new construction or contemporary open-concept floor plans
- Investors seeking quick turnover or heavy rental supply, given the high owner-occupancy
- Anyone needing to close fast on limited inventory or unwilling to take on any renovation work
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 ($600K) IS the median in the snapshot above, and the move from 2025 ($605K) IS the -0.8% one-year change.
Windows contain 0 to 22 sales each (11 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.
36% of homes for sale in ZIP 32708 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 Winding Hollow buying strategy.
If we were buying in Winding Hollow 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 Winding Hollow.
A built-out street where updates set the price
With 161 homes built in a tight 1995–2000 window, Winding Hollow offers a consistent product: sizeable floor plans around the 2,529-square-foot median, on established lots with mature landscaping. There is no phase still under construction and no builder inventory to compete against, so the market here is purely resale.
The practical implication is that two homes of similar size can sit far apart on price depending on roof age, HVAC, kitchens, and baths. Read every listing through that lens. A higher number often reflects real capital already spent; a lower one may carry deferred work you'll inherit. Budget for inspection and, where needed, a renovation reserve rather than assuming turnkey.
The location and the amenities are priced into every listing in Winding Hollow. 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 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 4 factors (7.7). Basis: Long-Term Appreciation +115% since 2012; Recent Direction -0.8% year-over-year; Owner Commitment 92% owner-occupied; Pricing Power 97.4% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a low-turnover, owner-held community like this, the edge comes from knowing which homes have been updated and which are trading on original condition. We help sellers price to their actual improvements and help buyers separate a fair renovation discount from a problem, so you're negotiating on facts, not finishes.
Winding Hollow 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 Winding Hollow 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 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, 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 home worth?
Get a no-obligation home value based on real comparable sales in Winding Hollow, 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
What is the median home price in Winding Hollow?
How long do homes in Winding Hollow take to sell?
How many homes are in Winding Hollow?
What share of Winding Hollow is owner-occupied?
When were the homes in Winding Hollow built?
Do cash buyers compete in Winding Hollow?
Have Winding Hollow home prices gone up?
Who is the best real estate agent for Winding Hollow?
How do I find a top Winter Springs real estate agent who knows Winding Hollow?
Can Momentum Realty connect me with an agent for Winding Hollow?
Should you buy in Winding Hollow?
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 (14 streets, ZIP 32708)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| 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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More Winter Springs & Seminole County & North Orlando guides
Compare before you commit - every guide covers pricing, HOA/CDD, insurance posture, and fit. Browse all of Seminole County & North Orlando or the full Neighborhood Finder.
See how WINDING HOLLOW UNIT 5 fits the bigger picture — live prices, inventory, and Momentum Scores:
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