Neighborhood · Clearwater, Florida
Winding Wood 2
Practical Clearwater living at a mid-market price
2
Homes for sale
$248,950
Median list price
$177
Avg price / sqft
33
Median days on market
Winding Wood 2 is a quiet residential pocket in Clearwater's inland Countryside area, where modestly sized homes averaging around 1,405 square feet sit within easy reach of the shops and everyday errands that define this part of Pinellas County. It's the kind of neighborhood that appeals to buyers who want a settled, low-key setting without paying beach-adjacent prices — and it's assigned to Safety Harbor Middle School, Countryside High School, and Leila Davis Elementary School. You're a short drive from bigger Clearwater draws, from the sand at Sand Key to the restaurants and events of Downtown.
The market here is small and moves at a measured pace. Right now there are just two active listings, with a median list price of $248,950 and homes taking a median of about 31 days to sell. Over the past year 14 homes sold at a median of $215,500, with sellers netting roughly 94% of asking — useful context whether you're comparing against nearby Clearwater homes for sale or a larger community like On Top Of The World.
Winding Wood 2 is a community in Clearwater, Florida.
Quick facts
$247,999 – $250K price range
1,405 sqft median home
$688/mo median HOA
14 sold in 12 months
On the market now
Homes for sale in Winding Wood 2
$247,999
2630 CEDAR VIEW COURT UNIT 0, CLEARWATER
3 bd · 2 ba · 1,405 sqft
$249,900$259,900
2617 BARKSDALE COURT, CLEARWATER
3 bd · 2 ba · 1,405 sqft
Every active listing inside the Winding Wood 2 boundary
Open full map search →Find your fit
Browse Winding Wood 2
By feature — on the live map
The numbers that matter
The Winding Wood 2 market
14
Sold, last 12 months
$215,500
Median sold price
94%
Sale-to-list ratio
What sellers actually get vs asking
26 days
Median time to sell
Winding Wood 2 vs Clearwater
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 25.3% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Winding Wood 2 boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Winding Wood 2 is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Winding Wood 2 home
≈ $2,507/mo
$248,950 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$688/mo
Median HOA
From current listings inside the boundary
Population
620
Median age
59
Median income
$58,980
Median home value
$181,800
Beyond the listings
Living in Winding Wood 2
Appearance oriented
Top 1% in the U.S.Smart Chic
Passionate about style, smart chic searches high and low for the perfect look - but not one that will break the bank.
Appearance oriented
Top 1% in the U.S.Trend Trackers
This population lives as fast as the culture. They like to keep up with the latest trends, especially when it comes to apparel and accessories.
Hobbies & Interests
Top 2% in the U.S.Handcrafted
The only thing more beautiful than handmade decor? The hands that made it. This population appreciates the time and care put into one-of-a-kind pieces.
Attitudes
Top 2% in the U.S.Deal Seekers
These people are hunting discounts, contests, and promotions. The population loves a good sale, and they can't wait to share their bargain finds and winnings with friends and family.
Appearance oriented
Top 4% in the U.S.Body Art
Who says the body isn't a canvas? This population loves talking about tattoos, body art and piercings.
Lifestyles
Top 6% in the U.S.Nerd Culture
These people aren't afraid to nerd out. Common activities include comic books, video games, and often intellectual pursuits.
People who close here
Our Clearwater experts
Straight answers
Winding Wood 2 FAQs
Is Winding Wood 2 a good place to live?+
It's a good fit if you want a quiet, residential Clearwater neighborhood with right-sized homes and solid school assignments — Safety Harbor Middle, Countryside High, and Leila Davis Elementary. The setting is low-key and central, with easy access to shopping and a short drive to beaches and Downtown.
Is Winding Wood 2 expensive?+
No — it sits comfortably in Clearwater's mid-market range, with a median list price of $248,950 and homes selling at a median of $215,500 over the past year. Compared to waterfront pockets like Sand Key, it's an accessible entry point into the area.
What do homes cost in Winding Wood 2?+
Active listings currently run between $247,999 and $249,900, with a median around $248,950 and an average of $177 per square foot. Over the last 12 months the median sold price was $215,500, so buyers should expect list and sale prices to differ.
How is the market in Winding Wood 2?+
It's a small, steady market with just two active listings and 14 sales in the past year. Homes take a median of about 31 days to sell, and sellers are getting roughly 94% of asking on average — a sign there's room to negotiate.
What about HOA fees and property taxes?+
The median HOA fee here is $688 per month, which is on the higher side and typically reflects maintained common areas or included services worth confirming per listing. Median property taxes run about $3,565 per year.
Keep exploring
More Clearwater neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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