Buying or selling? Call (904) 351-6461
Trails Of Countryside in Clearwater

Trails Of Countryside
Homes for Sale in Clearwater, FL

Buying in Clearwater? Get matched with a local agent →Selling? Get your Clearwater home value →or call (904) 351-6461

All 1,265 homes for sale in Clearwater, FL · median $315,000 · 131 homes for sale in 33761 · Pinellas County homes for sale

Community in Clearwater · Pinellas County · ZIP 33761
78 homesBuilt 1978–2000
Free · No obligation
Talk to a Trails Of Countryside Expert

True comps, carrying-cost math, and listings before the portals.

Photo via Stellar MLS

Built fromLive Stellar MLS data14 years of closingsFL DOR public recordsUpdated twice daily

As of October 2026, Trails Of Countryside in Clearwater, FL has 1 home for sale. Homes listed or recently sold were built 1986–1989; 4 of 4 report an HOA (median $8/mo); none of the 4 geocoded homes sit in a FEMA special flood hazard zone (median elevation 71 ft).

Part of the Countryside master-planned community in Clearwater, FL — see all Countryside homes for sale (42 listings across 20 villages and sections in the MLS).

Last 30 days in Trails Of Countryside: 1 under contract right now, 1 closed sale (median $849,000). As of October 20, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.

Live · Trails Of Countryside Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Tempo
6.0mo
Supply
3 to 6 months is the balanced band
50%
Under contract
Pinellas: 20% (1,627 of 8,166)
1 · 1
For sale · pending
live counts, refreshed twice daily
2
Sold · last 12 mo
10-yr average: about 1 a year
Ownership and context
91%
Owner-occupied · Trails Of Countryside
71 of 78 parcels homesteaded (FL DOR 2025)
9%
Non-owner-occupied · Trails Of Countryside
incl. 5% trust or LLC-held · 0% out-of-state
78
Homes in the community
78 residential parcels (FL DOR 2025)
Track record · 14 years of records
4
Recorded sales · 2024-2025
median $830K · qualified sales on the county roll (FL DOR 2025)
Est. 1978
Community established
homes built 1978-2000, median 1987 (FL DOR 2025)
2.6%/yr
Turnover rate
about 2 of 78 homes trade a year
Trails Of Countryside Housing Pulse · Momentum Research · as of September 20, 2026

Trails Of Countryside right now

🟡 Balanced market. 6.0 months of supply and 50% of the inventory already under contract put buyers and sellers on roughly even footing.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 September 20, 2026. Confidence: Low (2 active and pending listings, 2 closed sales in 12 months).

Jump to: Price history & scorecard · Homes for sale · Schools · FAQ

By , Co-Founder, Momentum Realty · Updated October 20, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness

The Area Market

The market around Trails Of Countryside

Trails Of Countryside is too small for its own price trend, so here is the market around it.

In ZIP 33761, 159 homes are on the market and 25% are under contract — a steady corner of Clearwater.

Across Pinellas County, 6,539 homes are active and 1,627 pending (20% under contract).

ZIP and county figures describe the wider market, not Trails Of Countryside specifically. Momentum Research analysis of MLS records.

Homes For Sale Right Now in Trails Of Countryside

Live MLS inventory for Trails Of Countryside. 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.

3408 FAIRFIELD TRAIL home for sale in Trails Of CountrysidePending · 278 days
$699,000
4 bd · 2 ba · 2,411 sqft · built 1987
3408 FAIRFIELD TRAIL, CLEARWATER, 33761
Listed by WATERFRONT REALTY TAMPABAY

Active and pending Trails Of Countryside listings as of 2026-10-19, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2012 through 2026. Tap any home to ask about it.

Interactive Map

Trails Of Countryside 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 contributors.

Schools

In short
  • Pinellas County Public Schools
  • Verify the zoned schools by address
  • Magnet and choice options may be available
  • Curlew Creek Elementary-PN · Elementary
  • Palm Harbor Middle-PN · Middle
  • Palm Harbor Univ High-PN · High

Zoned schools reflect the assignments reported on recent Trails Of Countryside listings and can change; always confirm with Pinellas County Public Schools for a specific address.

Buying with schools in mind? We can confirm the exact zoned schools for any Trails Of Countryside address.

Shop the zone: Homes zoned for Palm Harbor Univ High-Pn High School

The Strategy

The Trails Of Countryside buying strategy.

If we were buying in Trails Of Countryside today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 Trails Of Countryside.

The Deep Dive

A closer look at the Trails Of Countryside market

Inventory runs at 6.0 months of supply, a balanced market.

The housing stock is 78 homes built between 1978 and 2000, and 91% 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 Trails Of Countryside. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

What it really costs to own in Trails Of Countryside

The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.

HOA duesMLS listings here mostly enter dues as billed annually, but the median entry is only $100/year across 3 listings (2026-10-20), which usually means a quarterly or monthly amount was entered as annual. Ask the association for the current dues.
Home and flood insuranceThe average Citizens Property Insurance premium in Pinellas County is $1,911/yr (20,791 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction.
Roof and ageMedian build year 1986 across 3 listings. An original roof here would be about 40 years old; under Florida's 2022 reform (SB 2-D) carriers may require an inspection past 15 years, so budget for a roof report, and for replacement where it fails.

Email me new listings in Trails Of Countryside

One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.

Equal Housing Opportunity. Every community is open to everyone; alerts are about homes, never about who lives here.

Ask an agent about Trails Of Countryside

Have a question about the homes, fees, rules or commute here? A Momentum agent who works Trails Of Countryside will answer, and the answer is published on this page for the next buyer.

Property facts only: homes, fees, rules, commute. Every community is open to everyone; agents do not answer questions about who lives here.

HOA, CDD & Fees

A note on who we are: Momentum Realty is a real estate brokerage. We are not the Trails Of Countryside homeowners association, its management company or its developer, and we cannot help with dues, gate access, violations, amenity bookings or association documents. To reach the association, check your closing package, the recorded declaration at the county clerk, or search the association’s name at sunbiz.org for its registered agent. Call or message us to buy or sell a home in Trails Of Countryside.
In short
  • HOA dues in MLS listings look inconsistent here (median entry $100/year across 3 listings). Confirm the current dues with the association
  • Any club/amenity membership is billed separately

MLS listings here mostly enter association dues as billed annually, but the median entry is only $100 a year across 3 records, which usually means a quarterly or monthly amount was entered as annual. Ask the association or the listing agent for the current dues and what they cover before you offer. Source: MLS listing records, 2026-10.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.

Run Your Numbers

Tools for a Trails Of Countryside buy.

Free calculators to pressure-test the real cost before you tour.

Mortgage paymentPrincipal, interest, taxes, and insurance on a specific price.Property taxPinellas County millage and the homestead picture.Rent vs buyThe breakeven on owning in Trails Of Countryside.Save Our HomesProject your homestead tax cap over time.
The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Trails Of Countryside sales matched to your home.

Selling in Trails Of Countryside

Price it to the comps and condition, not an automated estimate.

If you are thinking about selling in Trails Of Countryside, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.

What is your Trails Of Countryside home worth?

Get a no-obligation home value based on real comparable sales in Trails Of Countryside, 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 all homes for sale in Clearwater →

Real comps, not an automated estimate.

Recently off market in Trails Of Countryside

Homes in Trails Of Countryside that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 1 on record.

Trails Of Countryside key facts
LocationClearwater, Pinellas County, FL · ZIP 33761
Homes in the community78 (FL DOR 2025 assessment roll)
Years built1978–2000 (median 1987.0)
Typical living area2,908 sq ft (median)
Amenities listed by sellersDeed Restrictions, Golf Carts OK, Security System
For sale right now1 active, 1 pending · median asking $849,000 · 6.0 months of supply
Owner-occupied (homestead) share91%

Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2012 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Trails Of Countryside key facts,” movewithmomentum.com/neighborhoods/trails-of-countryside, data as of September 20, 2026.

Housing distress & ownership in Trails Of Countryside, Clearwater

Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.

Active inventory in distress
0.0%
0 of 5 listings
Distress share trend — 0.0% now (2026-09-13 → 2026-10-17)

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 October 2026 through October 2026. Deemed reliable but not guaranteed.

Every Home for Sale in Trails Of Countryside Right Now (1)

All 1 active and pending Trails Of Countryside listings with a detail page, newest first, refreshed twice a day from the MLS.

How much local inventory is already under contract

22% of homes for sale in ZIP 33761 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 (2026-10-18).

Frequently Asked Questions

Is Trails Of Countryside a buyer's or seller's market right now?
As of September 20, 2026, Trails Of Countryside is roughly balanced: 6.0 months of supply at the current sales pace (Stellar MLS live counts).
How many homes are in Trails Of Countryside?
The Florida DOR 2025 assessment roll shows 78 homes in Trails Of Countryside (public records).
What share of Trails Of Countryside is owner-occupied?
91% of Trails Of Countryside parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Trails Of Countryside built?
Homes in Trails Of Countryside were built between 1978 and 2000, with a median year built of 1987.0 (FL DOR 2025 roll).
Who is the best real estate agent for Trails Of Countryside?
The best agent for Trails Of Countryside is one who actively works Clearwater and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Trails Of Countryside.
How do I find a top Clearwater real estate agent who knows Trails Of Countryside?
Share a few details in the form on this page. Momentum Realty has 320+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Trails Of Countryside and the wider Clearwater area.
Can Momentum Realty connect me with an agent for Trails Of Countryside?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Trails Of Countryside purchase or sale - no call center and no pressure.
Where is Trails Of Countryside, and what county is it in?
Trails Of Countryside is in Clearwater, Pinellas County, FL, ZIP 33761. The community's center is about 5 miles northwest of the center of Clearwater (straight-line).

Data sources & freshness

Live listingsStellar MLS, refreshed twice daily (last: October 19, 2026)
Housing stock & ownershipFlorida DOR assessment roll (street-list match (6 streets, ZIP 33761))
Under-contract sharesStellar MLS records, as of 2026-09-20
Historical depthClosed-sale records back to 2012 (27 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 local comps.

Looking to buy here? Search homes for sale →

What’s your home worth in your area?

A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.

By submitting, you agree that EAB RE INVESTMENTS LLC (Momentum Realty) and its agents may call, email, and text you about your inquiry, which may involve automated means and prerecorded or artificial voices. You do not need to consent as a condition of buying any property, goods, or services. To opt out, reply STOP at any time or reply HELP for assistance. You can also click the unsubscribe link in emails. Message and data rates may apply. Message frequency may vary. See our Privacy Policy and SMS Terms.or call (904) 351-6461
CallFree valuation →

Nearby Communities

Explore more neighborhoods near Trails Of Countryside with Momentum Realty’s local guides.

CCCurlew City0.2 mi away · median $448K, 4 sales/12 moCurlew City0.2 mi away · median $368K, 6 sales/12 moATAspen Trails0.2 mi awayWLWynwoods Landing0.2 mi away · median $799K, 4 sales/12 moCClubhouse0.3 mi away · 37 homes, built 1981–92CGCurlew Groves0.3 mi away · 238 homes, built 1973–07

Browse all neighborhood guides →

Thinking of selling in Trails Of Countryside? 2 recorded closings (window ending 2026-09-20). See the Pinellas County sell-now-or-wait data, what made 201,552 Florida listings fail in the last 12 months, or compare a cash offer vs. listing. Compiled from MLS records; deemed reliable but not guaranteed.
Talk to a Local Trails Of Countryside Expert
Call Get Listings