Countryside Homes for Sale in Clearwater, FL

Established master-planned community · North Clearwater · ZIP 33761

A large, established master-planned community in north Clearwater, built mostly in the 1970s and 1980s around the Countryside Country Club and Countryside Mall. The read is which sub-association governs the home, the year built and condition, and the full carrying cost including insurance.

North ClearwaterEstablished 1970s to 1980sCountry club and mall nearby

Live Market Pulse

50/100
Momentum

Buyer-Leaning Market (limited data)

Resale here turns on the specific sub-neighborhood, the year built, the condition and any updates; confirm the governing sub-association, its dues and rules, and the flood and insurance picture before anchoring on a number.

Free · No obligation

Unlock Off-Market Countryside

Listings before the portals, true comps, and the renovation and carrying-cost math, before you tour.

Built fromLive Stellar MLS data14 years of closingsLocal renovation analysisUpdated twice daily

LiveMarket PulseStellar MLS

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Median Price

0mo

Supply

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Avg DOM

Soft

Seller Leverage

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Median $/Sqft

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1-Yr Price Change

0now

Distress

Jon's Current Read

"Countryside is a large, established master-planned community in north Clearwater, developed mostly in the 1970s and 1980s and made up of many distinct sub-neighborhoods clustered around the private Countryside Country Club and the Countryside Mall on U.S. 19. The housing stock is predominantly single-story ranch and split-plan single-family homes on generous lots, many now updated. Because the community is a patchwork of separate sub-associations, the governing documents, dues and rules differ block to block, so the first read is which association applies to the specific home. The second read is the year built and condition, since 1970s and 1980s systems and roofs drive insurance and renovation cost. The location is the durable strength: shopping, dining, U.S. 19 and Tampa-area commuting are all close."

Jon Brooks, founder, Momentum Realty · Updated June 2026

The 60-Second Overview

Countryside is a large, established master-planned community in north Clearwater (ZIP 33761), Pinellas County, developed mostly in the 1970s and 1980s. It is made up of many distinct sub-neighborhoods, such as Countryside Pines, Bryn Mawr, Clubhouse Estates and Cypress Bend, clustered around the private Countryside Country Club and the Countryside Mall on U.S. 19.

The housing stock is predominantly single-story ranch and split-plan single-family homes on generous lots, built in the 1970s and 1980s, with many now carrying modern updates. Each sub-neighborhood has its own character, so value and feel vary from street to street rather than across one uniform plan.

Because the community is a patchwork of separate sub-associations, the governing documents, dues and rules differ by sub-neighborhood. Confirm which association applies to the specific home, its dues, and any rental, pet or exterior rules before you offer.

Confirm the year built, roof and major-system age, the flood zone and current insurance quotes, and the school assignment by address with Pinellas County Schools if that matters to you, since these are parcel-specific and drive the carrying cost.

Quick Match

Who Countryside is best for.

Best for

Buyers who want an established single-family home on a generous north Clearwater lot
Buyers who value being close to shopping, dining, golf and U.S. 19
Buyers comfortable with a 1970s or 1980s home they may update
Buyers who will confirm the governing sub-association, insurance and roof age

Probably not for

Buyers who want uniform new construction
Buyers who want one community-wide HOA and amenity bundle
Buyers unwilling to confirm roof age, insurance and sub-association rules
Buyers who want a short-term vacation-rental property

Market Pulse

How Countryside is performing right now

50/100
momentum

Buyer-Leaning Market (limited data)

Seller's marketBalancedBuyer's market

0Months of supplytight

56Median days on marketdays

0 : 0Under contract vs for salestrong demand

0Sold in last 12 monthsliquidity

+127%Median price since 2012appreciation

+0%Asking vs recent sold $/sqftroom to negotiate

Tight supply and strong demand favor sellers here. Homes still take about two months to sell, though, and with asking prices running above recent sales per square foot, a prepared buyer has room on anything overpriced. Reading each home against the real comps, not the headline trend, is where the edge is.

Live from Stellar MLS, as of June 24, 2026. Refreshed twice daily. Months of supply, days on market, and the contract-to-listing ratio are computed from current Countryside listings and the trailing twelve months of closed sales.

Where prices are going$850K2026 YTD

Median sale price by year. Tap a label to compare Curlew City or Clearwater. The 1-year price change is the median sold price over the most recent year versus the prior year, the same measure most listing sites and local Realtor reports use. It reflects the mix of homes that sold, not the change in any single home's value, which is why median price per square foot is shown alongside it to adjust for home size. In thinly traded neighborhoods, where a sale or two can swing the median, we lead with the mix-resistant price-per-square-foot trend instead.

Price per square foot$3072026 YTD

Median $/sqft by year. 2026 is year to date.

Supply and demand now0 : 0active : pending

For sale0

Pending0

Sold 12mo0

Active and pending listings now vs homes sold in the last 12 months.

8.6A- score

Momentum intelligence

Momentum buy score

Our proprietary read on how a home in Countryside buys, holds, and resells. See the five factors.

Interactive Map

Countryside on the map.

Every active, pending, and recently sold home, plotted. Toggle the layers, color the dots by status or lot type, and tap a home for the details.

Listing locations from Stellar MLS; lot type inferred from listing descriptions. Destination pins are approximate. Map data © OpenStreetMap, tiles © CARTO. Flood, school, and commute overlays are on the roadmap.

The Club & Membership

15-Second Take

The Countryside Country Club is a separate private membership, not bundled with most homes
Confirm golf, tennis, pool and dining membership options and costs with the club
Sub-association amenities and dues vary by sub-neighborhood; confirm in writing
The sub-neighborhood, lot and condition drive resale here
Confirm any special assessment for the specific home

Countryside is a large, established master-planned community in north Clearwater (ZIP 33761), Pinellas County, developed mostly in the 1970s and 1980s and made up of many distinct sub-neighborhoods clustered around the private Countryside Country Club and the Countryside Mall on U.S. 19. The housing stock is predominantly single-story ranch and split-plan single-family homes on generous lots, many now updated. Because the community is a patchwork of separate sub-associations, confirm which association governs the specific home, its dues and rules, the year built and roof and system age, the flood zone and insurance quotes, the short-term rental rules per the city and sub-association, and the school assignment by address with Pinellas County Schools, since details change.

Nearby & Commute

How far is everything?

The takeaway

The north Clearwater location is the point: shopping, golf, U.S. 19, Dunedin and the Gulf beaches are all within a reasonable drive.

Drive times from the community area; the central north Clearwater location puts shopping, golf, major roads and the coast within reach.

Countryside Mall and shopping~3 to 8 min · ~1 to 4 miles

Countryside Country Club~3 to 8 min · ~1 to 4 miles

U.S. 19 corridor~3 to 8 min · ~1 to 4 miles

Downtown Dunedin~10 to 18 min · ~5 to 8 miles

Honeymoon Island and Gulf beaches~15 to 25 min · ~8 to 13 miles

Tampa International Airport~25 to 40 min · ~18 to 26 miles

Drive times are approximate and vary with traffic and your exact departure point. Confirm your real commute at your real departure time.

Nearby Communities

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

EPEstancia PlaceClearwater, FL · 0.3 mi WLWestchester Lake TownhomesClearwater, FL · 0.4 mi WOWestchester ofCountrysideClearwater, FL · 0.4 mi CEClubhouse Estatesof Countryside, ClearwaterClearwater, FL · 0.5 mi BMBryn Mawr atCountrysideClearwater, FL · 0.6 mi VOVillage onthe GreenClearwater, FL · 0.7 mi TCTownhomes of CountrysideClearwater, FL · 0.7 mi OFOak Forest ofCountrysideClearwater, FL · 0.8 mi TWOn Top of the WorldClearwaterClearwater, FL · 0.8 mi

Browse all Florida neighborhood guides →

Carrying cost · the no-CDD edge

No CDD bond means thousands less per year than newer master plans.

Typical CDD community~$2,500/yr

Countryside (no CDD)$0/yr

Roughly $25,000 saved over 10 years in carrying cost, before resale.

Illustrative. NE Florida CDD assessments commonly run $1,500-$3,500+/yr and vary by community; verify per property.

Schools

15-Second Take

Pinellas County Public Schools
Verify the zoned schools by address
Magnet and choice options may be available
Confirm current ratings before relying on them
Private and parochial options nearby

Countryside is served by Pinellas County Public Schools. Assignment is by address and can change, so confirm the exact zoned elementary, middle, and high schools for any specific home, plus any magnet or choice options. Treat published ratings as a starting point, not the full story.

Public

Pinellas County Public Schools (verify by address)

Verifyrating

By address

Confirm zoned elementary, middle, and high

Verifyrating

Choice

Magnet and choice options may apply

Verifyrating

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

The takeaway

What is actually shaping value in this north Clearwater community, sourced and dated. We do not publish rumor.

Recent Developments in Countryside

Development Intelligence

Our read on what is being built around Countryside, scored for direction, significance, and how close the effect lands. The full sourced timeline follows below.

Net OutlookBullishThe structural story is an established, well-located community where the specific sub-neighborhood, the year built and condition, and the full carrying cost drive outcomes. Watch Florida property-insurance costs and roof age on 1970s and 1980s homes against durable demand for established north Clearwater single-family housing near shopping and golf, and confirm the sub-association, roof, flood and insurance picture per home.

Location near shopping, golf and U.S. 19 anchors demand

Ongoing

BullishNotable impact

SignificanceRadius: Community

Proximity to the Countryside Mall, the Countryside Country Club and U.S. 19 keeps durable demand for these established homes; confirm the specific sub-neighborhood and condition per home.

Many separate sub-associations across the community

Ongoing

NeutralNotable impact

SignificanceRadius: Community

Countryside is a patchwork of distinct sub-associations, so dues and rules differ by street; confirm which association governs the specific home and its costs before you offer.

Florida property insurance is a real cost layer on older homes

Ongoing

BearishNotable impact

SignificanceRadius: Area

Insurance and roof age on 1970s and 1980s homes can move the carrying cost; confirm current quotes and roof age for the specific home before you offer.

Clearwater limits short-term residential rentals

2023

NeutralMinor impact

SignificanceRadius: Area

The city enforces an about-a-month minimum rental period in most residential districts; confirm the city code and any sub-association rule if rental use matters.

Direction, significance, and effect-radius ratings are Momentum's proprietary, qualitative read of the sourced items below, not investment advice or a prediction for any specific home.

Development, infrastructure, retail, and school activity affecting Countryside, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated June 2026.

Showing the latest, scroll for all updates ↓

April 2023
Regulation
Pinellas County adopts short-term rental ordinance
Pinellas County reported that on April 25, 2023 the Board of County Commissioners adopted a short-term rental ordinance establishing registration and operating standards for vacation rentals in unincorporated Pinellas County, part of a broader county and municipal push, including in Clearwater, to regulate short-term residential rentals. Why it matters: Short-term rental rules across Pinellas and Clearwater limit vacation-rental use in most residential areas. Treat Countryside homes as primary or long-term, not short-term rentals, and confirm the city code and any sub-association rule per home. Source

Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.

The Strategy

The Countryside buying strategy.

If we were buying in Countryside, this is the order of operations we would run, and the one we run for our clients.

Confirm which sub-association governs the home. Countryside is many separate associations, so dues, rules and amenities differ by sub-neighborhood.

Read the roof and major-system age first. On a 1970s or 1980s home, roof and system age drive insurance and renovation cost.

Confirm the flood zone and insurance quotes for the specific parcel before anchoring on a number.

Comp by sub-neighborhood, year built and updates, not by the Countryside name alone, since value varies block to block.

Weigh the nearby alternative, Curlew City, on lot, condition and total carrying cost.

The Quick Decision

Best Buy

A well-updated single-family home in a strong Countryside sub-neighborhood with a newer roof, the governing association confirmed, and the flood and insurance picture clear.

Biggest Risk

Paying for the Countryside name without confirming the specific sub-association rules, the roof age, or the insurance math on an older home.

Best Lot

Generous lots and the specific sub-neighborhood drive value; quiet interior streets and golf-adjacent positions defend price best.

Smart Timing

Inventory turns steadily across the many sub-neighborhoods; the right combination of sub-association, condition and roof age is worth waiting for, with insurance confirmed first.

Deep-Dive Intelligence

The full read, only if you want it.

The takeaway

On mobile, tap any heading below to open it. This is the home by home, lot by lot, club and renovation detail, organized so you can jump straight to what matters to you.

Community Details at a Glance

Countryside Homes For Sale

What your money buys in Countryside.

The takeaway

Three honest price bands. Condition and lot, not the square footage alone, decide where a home lands.

Here are the broad resale bands in Countryside today. The right home is the one matched to your budget and the renovation math, so seeing fitting listings early is the edge.

Entry: more original homes

The more original 1970s and 1980s homes in the smaller-lot or busier-street sub-neighborhoods, the entry door into Countryside. Confirm current pricing on the live listings below.

Lowest entry

Core: updated homes on quiet streets

The updated single-family homes on generous lots and quiet interior streets, the core of the community. Confirm current pricing on the live listings below.

Most inventory

High: golf-adjacent or fully renovated

The golf-adjacent positions and fully renovated homes with newer roofs. Sub-neighborhood and condition separate these most. Confirm current pricing on the live listings below.

Strongest resale

Approximate 2026 resale bands from third-party listing data and public records, not NEFAR statistics. Confirm pricing for a specific home.

See Off-Market & Private Listings

What Your Money Buys

What ~$900K buys here.

Three realistic price bands. Where a home lands comes down to condition and lot, not square footage alone.

Entry: more original homes

The more original 1970s and 1980s homes in the smaller-lot or busier-street sub-neighborhoods, the entry door into Countryside. Confirm current pricing on the live listings below.

Core: updated homes on quiet streets

The updated single-family homes on generous lots and quiet interior streets, the core of the community. Confirm current pricing on the live listings below.

High: golf-adjacent or fully renovated

The golf-adjacent positions and fully renovated homes with newer roofs. Sub-neighborhood and condition separate these most. Confirm current pricing on the live listings below.

Approximate 2026 resale bands from third-party listing data and public records, not NEFAR statistics. Confirm pricing for a specific home.

Operator Intelligence

Renovation & Resale Intelligence

The factors that actually move value in Countryside, condition, lot, and the renovation math, read from current listings and recent sales.

15-Second Take

Renovation math decides the deal
Golf and lake lots resell strongest
Roof and HVAC age drive the insurance quote
Interior lots are where buyers overpay

Proprietary Data

The renovation premium.

Renovated-listing inventory in Countryside is too thin right now to compute a reliable renovation premium. We read condition home by home against real comps before you offer.

Lot Value

The lot premium.

On golf, lake, and preserve frontage, the homesite is the part of your money the market gives back at resale. The house can be renovated; the lot cannot, so premium lots hold their value better than interior ones. How much more they command varies by frontage, view, and condition, which is why we read it home by home against real comparable sales rather than a single headline figure.

Operator Note

Most buyers overpay on interior lots in the back half of the community. A sharp renovation can distract you, but the weaker resale position follows the lot, not the finishes. We read the homesite before the kitchen.

Resale Strength Scorecard

How well Countryside holds value.

Our read on the factors that protect resale here, and the one to manage.

Established single-family housing stockSolid

North Clearwater location near shopping and golfStrong

Confirm which sub-association governs the homeManage it

Read roof and system age on a 1970s or 1980s homeWatch it

Confirm flood zone and insurance per parcelManage it

Momentum analysis based on the no-CDD structure, central location, built-out lot scarcity, the funded club plan, and the all-resale 1990s housing stock. Not a guarantee of future value.

Operator Note

The strongest value pocket is usually a renovated golf or lake home priced just under the next tier up. Buyers chasing the single biggest estate often pay estate prices for what is really a renovation project.

5 Mistakes Buyers Make in Countryside

15-Second Take

Calling the listing agent (who works for the seller)
Misjudging the renovation budget
Overpaying for an interior lot
Ignoring the optional club cost
Skipping the roof, HVAC, and systems check

In an all-resale, seven-figure, renovation-driven market, the same five mistakes cost buyers the most. Every one is avoidable with the right preparation before you tour.

Calling the listing agent

The agent on the sign works for the seller. In a market where condition swings price by hundreds of thousands, negotiating against that agent with no one in your corner is the costliest move of all.

Misjudging the renovation math

A dated home looks like a deal until you price the roof, HVAC, pool, and full modernization honestly. Underbudget the reno and the bargain becomes the expensive house.

Overpaying for an interior lot

Golf frontage, lakefront, and preserve lots carry real, durable premiums. Pay an estate price for an interior lot and you are buying the weakest version of the value.

Ignoring the club decision

The club is optional and separate, so two similar homes can cost very differently to own. Buyers who do not price the membership they will actually use misread their real monthly number.

Skipping the systems check

A 1990s home means 1990s-era systems unless updated. Roof age, HVAC age, pool equipment, and prior renovations drive both price and insurability, and a thorough inspection matters more here than in a new build.

“

Countryside is not one neighborhood, it is many. The deal is won or lost on which sub-association governs the home, the roof and system age, and the insurance math, confirmed before you offer.

Jon Brooks · Founder, Momentum Realty

Momentum Intelligence

Momentum Buy Score.

Our proprietary 0 to 10 read across the five factors that decide how a home here buys, holds, and resells.

7.9B+ · Buy Score

Resale Strength8.0/10

Renovation Risk6.8/10

Location Efficiency8.6/10

Long-Term Defensibility8.0/10

Carrying Cost Advantage6.6/10

Momentum Intelligence Scores are our proprietary, qualitative assessment based on the analysis on this page, on a 0 to 10 scale. They are a framework for comparing communities, not a guarantee of future value or advice on a specific home.

Momentum Housing Intelligence

Why our read on Countryside is different.

Most pages on this community are an automated estimate wrapped in stock copy. This one is built from the live Stellar MLS feed, fourteen years of closed sales, and a renovation-by-renovation read of what actually moves value here, lot by lot. No Zestimate, no guesswork.

Live Stellar MLS feed14 years of closed salesRenovation-premium analysisLot-by-lot, no automated estimates

Jon Brooks, founder of Momentum Realty. A housing economist with a background in real estate investment banking at Deutsche Bank and consulting at Ernst & Young, who has built and analyzed Northeast Florida real estate from the ground up.

About the analyst · Our methodology

Which Lots & Views Hold Value Best

Proprietary Data · Lot Value Map

Where the value actually sits. Each home is shaded by its price per square foot (a value read, not just a price) and ringed by lot type, so you can see at a glance which pockets carry a real, durable premium and where a renovation play makes sense.

Value ($/sqft)

$261 value$401 premium

GolfLake / waterPreserveInterior

Fill = price per square foot; ring = lot type, inferred from listing descriptions. Sold homes are shown by realized $/sqft (lot type not always recorded). Asking and recent-sold figures from Stellar MLS; for orientation, not an appraisal.

15-Second Take

The sub-neighborhood and lot drive resale more than finishes
Confirm the homesite, position and any golf or preserve exposure
Read roof and system age on the specific home
Confirm flood zone and insurance where applicable
Comp the specific home, not the Countryside average

In a community this large, the specific sub-neighborhood and the homesite set the floor on resale while the house itself can be updated. Read the lot, the position and any golf or preserve exposure first, confirm the roof and system age and the flood and insurance picture, then price the condition of the home against the closest comparable sale in the same sub-neighborhood rather than a Countryside-wide average.

The 15-Second Verdict

Countryside in 15 seconds.

Best forBuyers who want an established single-family home on a generous lot close to shopping, golf and U.S. 19 in north Clearwater.

Strong onLocation, generous lots, mature setting, and easy access to the Countryside Country Club, Countryside Mall and Tampa-area commuting.

WatchThe governing sub-association, the roof and system age, and the insurance. Confirm each per home, since Countryside is many separate associations.

Sweet spotA well-updated home with a newer roof in a strong sub-neighborhood, with the association rules and insurance confirmed.

Not forBuyers who want uniform new construction, one community-wide HOA, or a short-term vacation-rental property.

HOA, CDD & Fees

15-Second Take

Confirm which sub-association governs the specific home
Confirm dues, rules and any special assessment in writing
Treat the Countryside Country Club as a separate private membership
Confirm rental, pet and exterior rules for the sub-neighborhood
Budget roof and insurance separately on an older home

Countryside is made up of many separate sub-associations, so dues vary widely by sub-neighborhood, and some streets may have little or no mandatory association while others do. Confirm which association governs the specific home, its dues, and any special assessment in writing before you offer; we pull the documents for any home you consider.

What dues cover, if anything, depends entirely on the sub-association, ranging from common-area upkeep to little or nothing. The Countryside Country Club is a separate private membership and is not bundled with most homes. Confirm exactly what is and is not included for the specific home.

Run Your Numbers

Tools for a 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 Countryside.Save Our HomesProject your homestead tax cap over time.

The takeaway

Selling here is won on condition and view, not the Zestimate. The right number comes from closed comps matched to your renovation level and lot.

Selling in Countryside

Price it to your sub-neighborhood, condition and updates, with the carrying cost shown.

If you are selling in Countryside, the right list price comes from recent sales matched to your specific sub-neighborhood, year built, condition and updates, not the Countryside name alone. Clear roof, system, association and insurance information is a real asset.

Momentum listings (YTD)

97.98%

Sold-to-list ratio across our market for our agents, sellers keeping more of their price.

Market average (YTD)

96.73%

The broader metro average sold-to-list ratio over the same period.

Momentum days on market

64 days

Median days on market for our listings, faster sales mean less carrying cost and stronger leverage.

Market days on market

72 days

The broader metro median over the same period.

Sold-to-list and days-on-market figures reflect Momentum Realty listings versus our market average, year to date. Your home's result depends on pricing, condition, lot, view, and preparation.

In Countryside, condition and view decide your number

Because buyers here are weighing your home against renovated comps and cross-shopping Curlew City, a home priced to the community average instead of its true condition and view either leaves money on the table or sits. A renovated kitchen, newer roof and HVAC, and a golf or lake view all deserve to show up in your price, and a buyer pool reading renovation math needs to be shown why your home is worth it. We build that case with real comps and a pricing strategy for the current market.

What is your Countryside home worth?

Get a no-obligation home value based on real comparable sales in Countryside matched to your condition, lot, and view, 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 homes for sale in Countryside on the map →
Or get your Countryside home value & selling guide →

Real comps, not a Zestimate.

Countryside Market Scorecard

Strong seller's market

Countryside is currently a strong seller's market. About 1.8 months of supply, a median asking price of $1,019,500, and homes go under contract in about 79 days.

1.8

Months supply

$1,019,500

Median list

$847,500

Median sold

$313

Per sqft

Days on mkt

6/8/41

Active/Pend/Sold

Typical home value in the 32224 ZIP is $456,759, about 13.7% above the Florida norm (Zillow Home Value Index).

Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.

Live data: Stellar MLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.

Frequently Asked Questions

Where is Countryside located?

Countryside is a large established master-planned community in north Clearwater, FL (ZIP 33761), Pinellas County, clustered around the Countryside Country Club and the Countryside Mall on U.S. 19, with easy access to Dunedin, Palm Harbor, Safety Harbor and Tampa-area commuting.

What kind of homes are in Countryside?

Predominantly single-story ranch and split-plan single-family homes on generous lots, built mostly in the 1970s and 1980s, with many now updated. Confirm the specific size, year built, condition and lot for any home.

Is Countryside one neighborhood or several?

It is many. Countryside is a patchwork of distinct sub-neighborhoods such as Countryside Pines, Bryn Mawr, Clubhouse Estates and Cypress Bend, each with its own character and, often, its own association.

Does Countryside have an HOA?

It depends on the sub-neighborhood. Countryside is made up of many separate sub-associations, so dues and rules differ by street, and some areas may have little or no mandatory association. Confirm which association governs the specific home and its dues before you offer.

Is the Countryside Country Club included with a home?

No. The Countryside Country Club is a separate private membership with its own golf, tennis, pools and dining, and is generally not bundled with most homes. Confirm membership options and costs directly with the club if that matters to you.

What amenities are near Countryside?

The private Countryside Country Club offers golf, tennis, pools and dining, and the Countryside Mall on U.S. 19 anchors shopping and dining nearby. The Pinellas Trail and Gulf beaches are a reasonable drive.

What does a home in Countryside cost?

We do not publish a price figure here. Pricing tracks the specific sub-neighborhood, year built, condition and updates. Confirm current pricing on the live listings on this page; we pull exact comps before you offer.

Is Countryside in a flood zone?

Flood zones are parcel-specific across a community this large. Confirm the flood zone and current flood and wind insurance quotes for the specific home before you offer.

Can I use a home in Countryside as a short-term vacation rental?

Generally no. The City of Clearwater requires a minimum rental period of about a month in most residential districts, and individual sub-associations may add their own rental rules. Confirm the city code and the sub-association rules for the specific home before counting on rental income.

What schools serve Countryside?

The community is in Pinellas County Schools, with assignment by address. Zoning can change, so confirm the current zoned campuses for any specific home with the district.

How old are the homes in Countryside?

Most were built in the 1970s and 1980s as the community was developed. Roof and major-system age vary widely by home and updates, so confirm both for the specific property, since they drive insurance and renovation cost.

Is now a good time to buy in Countryside?

Inventory turns steadily across the many sub-neighborhoods, so it depends on the specific home, its condition and roof age. We pull live inventory and comps so you can judge value and the full carrying cost.

Is Countryside a good place to buy?

It can be, for a buyer who wants an established single-family home on a generous north Clearwater lot near shopping and golf, and who confirms the sub-association, the roof age and the insurance picture. We pull live inventory and comps so you can judge value on the actual property.

Do I need my own agent to buy in Countryside?

Yes. The listing agent works for the seller. Your own agent confirms which sub-association governs the home, its dues and rules, the roof and system age, and the flood and insurance picture, pulls true comps, and negotiates for you. Momentum Realty represents you, not the seller.

Who is the best real estate agent for Countryside?

The best agent for Countryside is one who actively works Clearwater and knows the community's pricing, HOA and CDD details, 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 Countryside.

How do I find a top Clearwater real estate agent who knows Countryside?

Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Countryside and the wider Clearwater area.

Can Momentum Realty connect me with an agent for Countryside?

Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Countryside purchase or sale — no call center and no pressure.

The Verdict

Should you buy in Countryside?

An honest fit check. We will tell you when it is not your community.

You want an established single-family home on a generous north Clearwater lotExcellent fit

You value being close to shopping, dining, golf and U.S. 19Excellent fit

You are comfortable with a 1970s or 1980s home you may updateExcellent fit

You will confirm the governing sub-association, insurance and roof ageExcellent fit

You want a settled, mature community with quick Tampa-area accessExcellent fit

You want uniform new constructionProbably not

You want one community-wide HOA and amenity bundleProbably not

You will not confirm roof age, insurance and sub-association rulesProbably not

You want a short-term vacation-rental propertyProbably not

You want the lowest possible monthly carry on an older homeProbably not

Get the inside read on Countryside

Whether you are buying a renovation project, comparing the lots and views, weighing the optional club, or selling your Countryside home, tell us what you need. Every inquiry comes straight to us. We represent you, not the seller, and what your agent is paid is negotiable and set in a written buyer agreement up front. No obligation, no spam, no high-pressure follow-up.

You are all set.

A Momentum Realty Countryside specialist will reach out personally, usually the same day.

Thinking about hiring an agent here? How to find the best real estate agent in Countryside — what to look for, questions to ask, and your local expert.

Photography on this page is sourced from active and recently sold MLS listings in this community and remains the property of the listing brokerage and/or photographer. Listings courtesy of Stellar MLS as distributed by MLS GRID. 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; deemed reliable but not guaranteed by MLS GRID.

Countryside Homes for Sale in Clearwater, FL

The 60-Second Overview

Who Countryside is best for.

Best for

Probably not for

How Countryside is performing right now

Countryside on the map.

The Club & Membership

How far is everything?

Nearby Communities

Schools

Pinellas County Public Schools (verify by address)

Confirm zoned elementary, middle, and high

Magnet and choice options may apply

Recent Developments in Countryside

Location near shopping, golf and U.S. 19 anchors demand

Many separate sub-associations across the community

Florida property insurance is a real cost layer on older homes

Clearwater limits short-term residential rentals

Pinellas County adopts short-term rental ordinance

The Countryside buying strategy.

The full read, only if you want it.

What your money buys in Countryside.

What ~$900K buys here.

Renovation & Resale Intelligence

The renovation premium.

The lot premium.

How well Countryside holds value.

5 Mistakes Buyers Make in Countryside

Calling the listing agent

Misjudging the renovation math

Overpaying for an interior lot

Ignoring the club decision

Skipping the systems check

Momentum Buy Score.

Why our read on Countryside is different.

Which Lots & Views Hold Value Best

Countryside in 15 seconds.

HOA, CDD & Fees

Tools for a Countryside buy.

Price it to your sub-neighborhood, condition and updates, with the carrying cost shown.

In Countryside, condition and view decide your number

What is your Countryside home worth?

Price History: What Homes Here Have Actually Sold For

Countryside Market Scorecard

Frequently Asked Questions

Should you buy in Countryside?

Get the inside read on Countryside

You are all set.

Need to sell fast in Pinellas County?

You just read the data. Now see what your home is worth.