Homes for sale · Clearwater, FloridaCountryside
North Clearwater living with pools, golf-course greens and gulf access
46
Homes for sale
$434,450
Median list price
$262
Avg price / sqft
34
Median days on market
Countryside sits in the northern reaches of Clearwater, a well-established pocket of Pinellas County where mature oaks shade quiet residential streets and daily life runs on short drives to shopping, parks and the gulf beaches. It's the kind of place that suits buyers who want a settled, suburban rhythm without giving up proximity to the water — with communities like Cove Cay and Sand Key rounding out the range of what's nearby. The housing leans toward single-family homes and condos, many with pools, and the overall feel is lived-in rather than brand-new.
For a buyer today, the market reads as active but measured. There are 47 active listings with a median list price of $350,000, though the 135 homes sold over the past year closed at a median of $545,000 — a reminder that list and sold figures track different mixes of property. Homes move in about 37 days and sellers are getting 97% of asking on average, so there's room to negotiate but not to lowball. Compared with the broader Clearwater market, Countryside offers a wide price band, from entry-level condos around $110,000 to a handful of listings above $1M.
Countryside is a community in Clearwater, Florida.
Quick facts
$110,000 – $1.5M price range
1,592 sqft median home
$451/mo median HOA
$2,100/mo median rent
135 sold in 12 months
Drive times
Living in Countryside
Countryside is an established residential area in the northern part of Clearwater, within Pinellas County on Florida's gulf coast. The streets are lined with mature trees and homes that have had decades to settle into their surroundings, giving the area a grounded, lived-in character rather than the uniform feel of a new subdivision. Daily life here revolves around short drives to shopping, golf and the beaches that define this stretch of the coast.
The area draws a wide range of residents, from first-time buyers finding value in condos to families in single-family homes and downsizers drawn to maintained communities. Pools are a common feature — 18 of the 47 active listings have one — which tells you a lot about how people spend their time. The emphasis is on comfortable, practical Florida living with the water never far away.
Because Countryside sits in the broader Clearwater market, buyers benefit from proximity to the gulf beaches and the amenities of a larger coastal city while living in a quieter, more residential pocket. It's a place that suits people who value established neighborhoods and convenience over the shine of brand-new construction.
Neighborhoods and communities in Countryside
The area around Countryside includes several distinct communities, each with its own character. On Top Of The World is one of the largest and most recognizable, a planned community that tends to appeal to buyers looking for an amenity-rich, lower-maintenance lifestyle. Its scale and layout set it apart from the surrounding single-family streets.
Cove Cay and Sand Key offer different takes on waterfront and resort-style living, with Sand Key in particular tied to Clearwater's gulf-front identity. Imperial Cove rounds out the picture as another established community in the area. Each has its own fee structure and property mix, so it pays to compare carefully.
For buyers who want a more urban setting, Downtown Clearwater is within easy reach and offers a different lifestyle altogether. The variety across these communities means a buyer can find anything from a maintained condo to a single-family home with a pool without straying far from the Countryside area.
Homes for sale in Countryside: prices and housing
There are currently 47 active listings in Countryside, with a median list price of $350,000 and a range that stretches from $110,000 to nearly $1.5M. That spread reflects a genuine mix of property types, from affordable condos to larger single-family homes and a small number of high-end listings. The average price works out to about $258 per square foot, with a median home size of roughly 1,349 square feet.
Over the past 12 months, 135 homes have sold at a median price of $545,000 — notably higher than the median list price, which points to strong demand for larger homes. Homes sell in a median of 37 days, and sellers are getting about 97% of their asking price on average, signaling a balanced market where realistic pricing matters. Among active listings, 18 have pools, two are gated, one is waterfront, and two are priced above $1M.
On the cost-of-ownership side, the median HOA fee is about $451 per month, which reflects the prevalence of condos and maintained communities in the area. Median property taxes run around $3,270 per year. There is no new-construction inventory currently on the market, so buyers here are shopping established homes — always confirm the specific HOA and tax figures for any property, since they vary widely by community.
Schools in Countryside
Countryside is served by the Pinellas County school district, which assigns schools based on a student's home address. The current data does not confirm specific assigned schools for the area, so buyers should not rely on assumptions about which schools serve a given street.
The most reliable way to check zoning is to use the Pinellas County Schools attendance locator and enter the exact address of any home you're considering. Assignments can differ between nearby streets, and they are subject to change, so verifying directly is essential.
If schools are a priority in your search, build that verification step into your process early. Confirm not only the assigned schools but also any magnet, choice or charter options available through the district.
Getting around Countryside
Countryside's northern Clearwater location gives it solid access across the Tampa Bay region. Tampa International Airport is roughly a 32-minute drive, which is convenient both for travel and for the many residents who commute across the bay. Downtown Tampa is about 35 minutes away under typical conditions.
Most of that travel relies on the major regional roads and bridges connecting Pinellas County to the Tampa side of the bay. As with anywhere in the region, peak-hour traffic can extend those times, so it's worth testing your specific commute at the hours you'd actually drive it.
Within the area itself, daily errands — shopping, dining and recreation — are generally short drives, which is part of what makes Countryside practical for everyday life. The gulf beaches are also close, a defining feature of living in this part of Clearwater.
Is Countryside a good place to live?
For buyers who want an established, convenient slice of northern Clearwater, Countryside makes a strong case. The wide price range — from $110,000 condos to homes near $1.5M — means there's an entry point for very different budgets, and the prevalence of pools and proximity to the gulf support a relaxed Florida lifestyle. Communities like On Top Of The World, Cove Cay and Sand Key add variety to what's available.
The trade-offs are worth weighing honestly. There's no new construction on the market, so buyers wanting modern builds will be looking at resales or renovated homes. The median HOA of around $451 per month is meaningful and reflects the area's condo and maintained-community makeup, so factor that into your budget alongside the roughly $3,270 median annual property tax.
The market itself is balanced and active, with homes selling in about 37 days at 97% of asking. That rewards buyers who come in prepared and sellers who price realistically. For someone who values settled neighborhoods, water access and easy regional connectivity over newness, Countryside is a sensible and livable choice within the wider Clearwater area.
On the market now
Homes for sale in Countryside
View all 46 →
$110,000
2452 ENTERPRISE ROAD UNIT 9, CLEARWATER
1 bd · 1 ba · 593 sqft
$1,129,000
3168 MASTERS DRIVE, CLEARWATER
5 bd · 3 ba · 3,446 sqft
$198,000
2650 COUNTRYSIDE BOULEVARD UNIT A306, CLEARWATER
2 bd · 2 ba · 1,110 sqft
$689,000
2670 SAINT ANDREWS DRIVE, CLEARWATER
3 bd · 2 ba · 2,550 sqft
$558,000
2831 LONG VIEW DRIVE, CLEARWATER
3 bd · 2 ba · 1,635 sqft
$789,000
2769 NORTHRIDGE DRIVE E, CLEARWATER
5 bd · 3 ba · 3,316 sqft
$489,900
2704 WOODVIEW COURT, CLEARWATER
3 bd · 2 ba · 1,642 sqft
$160,500
2650 COUNTRYSIDE BOULEVARD UNIT F110, CLEARWATER
2 bd · 2 ba · 1,110 sqft
$379,000
3266 PINE HAVEN DR, CLEARWATER
3 bd · 2 ba · 1,122 sqft
$839,000$849,000
2942 CLUBHOUSE DRIVE W, CLEARWATER
4 bd · 3 ba · 2,291 sqft
$1,499,900
2518 HICKORY COURT, CLEARWATER
3 bd · 2 ba · 2,194 sqft
$525,000
2347 BARKWOOD PASS, CLEARWATER
3 bd · 2 ba · 1,888 sqft
Every active listing inside the Countryside boundary
Open full map search →Find your fit
Browse Countryside
By feature — on the live map
Where the market lives
The numbers that matter
The Countryside market
135
Sold, last 12 months
$545,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
30 days
Median time to sell
Countryside vs Clearwater
Median list price
Price per sqft
Days on market
Live Stellar MLS data — every listing and closed sale inside the Countryside boundary. Rolling medians smooth single-month swings in small communities.
What it really costs
Owning here
Owning the median Countryside home
≈ $3,226/mo
$434,450 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$451/mo
Median HOA
From current listings inside the boundary
$2,100/mo
Median rent
Homes for rent inside the boundary
People who close here
Our Clearwater experts
Straight answers
Countryside FAQs
Is Countryside a good place to live?+
Countryside suits buyers who want an established, suburban Clearwater setting with easy access to shopping, golf and the gulf. The mix of single-family homes and condos — many with pools — appeals to a broad range of households, from first-time buyers to downsizers. Its northern Pinellas location keeps you close to the water while staying connected to the wider Clearwater area.
Is Countryside expensive?+
It spans a wide range. The median list price is $350,000, but active listings run from $110,000 at the condo end up to nearly $1.5M, so there's genuine choice across budgets. The median sold price over the past year was higher at $545,000, which reflects stronger demand for larger single-family homes.
What do homes cost in Countryside?+
The median list price is $350,000 and the average price works out to about $258 per square foot, with a median home size around 1,349 square feet. Over the last 12 months, 135 homes sold at a median of $545,000. Only two active listings are currently priced above $1M, and one is waterfront.
How is the market in Countryside right now?+
It's active and fairly balanced. There are 47 homes on the market, selling in a median of 37 days, and sellers are receiving about 97% of their asking price. That gives buyers some negotiating room while still rewarding sellers who price realistically.
What are HOA fees and property taxes like?+
The median HOA fee is about $451 per month, which is on the higher side and often reflects condo and maintained-community living in areas like Cove Cay. The median property tax runs around $3,270 per year. Always confirm the specific HOA and tax figures for any home, since they vary widely by community and property type.
What about schools in Countryside?+
Countryside falls within the Pinellas County school district, but specific assigned schools vary by address and aren't confirmed in the current data. Before you buy, verify the exact zoning through the Pinellas County Schools locator using the property address. School assignments can differ even between nearby streets.
How is the commute from Countryside?+
Tampa International Airport is roughly a 32-minute drive, and Downtown Tampa is about 35 minutes. Those times make Countryside workable for commuters crossing the bay, with the main regional roads carrying most of that traffic. Allow extra time during peak hours.
Is there new construction in Countryside?+
There is no new-construction inventory among the current active listings, so this is an area of established homes. Buyers looking for newer builds would typically need to look at renovated resales or expand their search within the broader Clearwater area. The trade-off is mature landscaping and settled neighborhoods.
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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