Neighborhood · Clearwater, Florida
Trails Of Countryside
Established Countryside Living Near Top Clearwater Schools
1
Homes for sale
$745,000
Median list price
$309
Avg price / sqft
205
Median days on market
Trails Of Countryside sits in the northeast pocket of Clearwater, an area defined by mature landscaping, quiet streets, and roomy single-family homes that appeal to buyers who want space without giving up proximity to Pinellas County's beaches and shopping. The neighborhood feeds into some of the area's most sought-after schools, and it's a short drive from the Gulf beaches at Sand Key and the revitalized Downtown waterfront. Compared with condo-heavy communities like On Top Of The World or Cove Cay, this is a family-oriented enclave of established homes.
Inventory here is tight — there's currently just one active listing on the market, priced at $745,000, so buyers should be ready to move when the right home appears. Over the past year four homes sold at a median of $765,000, with sellers collecting about 99% of their asking price, a sign of steady demand. If you're comparing options across Clearwater homes for sale, expect larger lots and higher price points than the county's condo segments.
Trails Of Countryside is a community in Clearwater, Florida.
Quick facts
$745,000 – $745K price range
2,411 sqft median home
$8/mo median HOA
2 sold in 12 months
On the market now
Homes for sale in Trails Of Countryside
Every active listing inside the Trails Of Countryside boundary
Open full map search →Find your fit
Browse Trails Of Countryside
By feature — on the live map
The numbers that matter
The Trails Of Countryside market
2
Sold, last 12 months
$737,500
Median sold price
99%
Sale-to-list ratio
What sellers actually get vs asking
115 days
Median time to sell
Trails Of Countryside vs Clearwater
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 2.8% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Trails Of Countryside boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Trails Of Countryside is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Trails Of Countryside home
≈ $5,059/mo
$745,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$8/mo
Median HOA
From current listings inside the boundary
Population
350
Median age
35
Median income
$99,828
Median home value
$418,300
Beyond the listings
Living in Trails Of Countryside
Appearance oriented
Top 5% in the U.S.All About Hair
Passionate about all things hair, this population is talking about hair tutorials or the hottest celebrity blowout.
Hobbies & Interests
Top 6% in the U.S.Engine Enthusiast
This population loves working on and showing off their cars, trucks and motorcycles. You can find them researching car shows and the hottest models on the lot.
Hobbies & Interests
Top 8% in the U.S.Wanderlust
Always thinking about their next destination, this population loves exploring new places abroad or right in their own backyard. They hold onto past trips by sharing their favorite memories and pictures year round.
Attitudes
Top 16% 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 20% in the U.S.Body Art
Who says the body isn't a canvas? This population loves talking about tattoos, body art and piercings.
Appearance oriented
Smart Chic
Passionate about style, smart chic searches high and low for the perfect look - but not one that will break the bank.
Straight answers
Trails Of Countryside FAQs
Is Trails Of Countryside a good place to live?+
It's an established, family-friendly neighborhood in northeast Clearwater with mature streets and roomy homes. The assignment to Countryside High, Palm Harbor Middle, and Curlew Creek Elementary makes it especially appealing to families, and you're a short drive from the Gulf beaches at Sand Key.
Is Trails Of Countryside expensive?+
It sits at the higher end of the Clearwater single-family market, with the current listing at $745,000 and a median sold price of $765,000 over the past year. That reflects the larger home sizes and the strong school zone rather than any luxury or waterfront premium.
What do homes cost in Trails Of Countryside?+
Recent sales cluster around $765,000, and the one active listing is priced at $745,000, working out to roughly $309 per square foot. The typical home is about 2,411 square feet, so you're paying for genuine living space.
How is the market in Trails Of Countryside?+
It's a low-inventory market — just one active listing right now, with four homes sold in the last 12 months. Sellers are getting about 99% of asking, though homes can sit for a while, with a median of 205 days on market, so pricing and patience both matter.
What about HOA fees and property taxes?+
The HOA is minimal here, with a median of about $8 a month, so it won't weigh on your budget. Property taxes are the larger line item, running a median of roughly $10,993 a year in line with the neighborhood's home values.
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.
Never miss a listing
New Trails Of Countryside homes, in your inbox
A daily digest of new Clearwater listings — straight from the MLS. Unsubscribe anytime.