Clearwater FL Realtor | Barrett Henry, Your Clearwater Real Estate Expert

Clearwater, Florida sits on the western edge of Pinellas County along the Gulf Coast, roughly 20 miles west of downtown Tampa. It is a city of sharp contrasts: some of the most photographed white-sand beach in the country on one side, and established, affordable suburban neighborhoods just a few miles inland on the other. That range of options is what makes Clearwater appealing to such a wide pool of buyers, and it is also what makes working with a knowledgeable agent so important.

Barrett Henry is a Broker Associate with RE/MAX Collective and has been serving the Tampa Bay area, including Pinellas County, for more than 23 years. Whether you are looking at a Gulf-front condo on Clearwater Beach, a waterfront home on Island Estates, or a family-sized house in Countryside, Barrett brings the same approach: accurate information, honest pricing guidance, and clear communication from first showing to closing.

Why Barrett Henry is Your Clearwater Real Estate Agent

Clearwater is not a simple, one-size-fits-all market. A beachside condo on Clearwater Beach carries different flood zone considerations, insurance requirements, and HOA structures than a single-family home in the Countryside neighborhood. Buyers relocating from outside Florida often underestimate how much these variables matter to the total cost of ownership and long-term value.

Barrett’s approach starts with understanding what you actually need. Are you buying a primary residence, a second home, or an investment property? Do you want Gulf views and walkability, or do you want a quieter inland neighborhood with lower insurance and better school access? Are short-term rental restrictions a concern? These questions shape the search strategy before you ever tour a home.

As a Broker Associate at RE/MAX Collective, Barrett has access to the full MLS and the RE/MAX global referral network. His designations include e-PRO, MRP (Military Relocation Professional), and SRS (Seller Representative Specialist). His office locations in Tampa, Largo, and Brandon keep him accessible throughout the Tampa Bay region, including Pinellas County.

The tagline says it plainly: MOVE WITH CONFIDENCE. Straight talk. Smart Strategy. That is the standard Barrett holds himself to in every Clearwater transaction.

Clearwater’s Most Popular Neighborhoods

Clearwater is home to a wide range of neighborhoods, from Gulf-front communities to suburban subdivisions well east of the water. Here is a rundown of the areas buyers most frequently ask about.

Clearwater Beach

Clearwater Beach is the crown of the market. This barrier island community is home to Gulf-front condos, elevated new construction, boating access, and strong short-term rental demand in many buildings. The median list price for Clearwater Beach properties was reported around $828,000 in late 2025, though the market saw year-over-year price corrections through much of 2025 as rates and inventory adjusted. Buyers here need to pay close attention to flood zone designations, building age, reserve fund health, and HOA rules on rentals. Barrett works through all of this systematically before any offer is made. For broader coastal context, see our Tampa Bay beaches guide.

Island Estates

Island Estates sits approximately one mile east of Clearwater Beach, connected by the Clearwater Memorial Causeway. It is a waterfront neighborhood where the vast majority of homes offer water views, private docks, and direct access to Clearwater Bay and the Intracoastal Waterway. Single-family homes range from roughly $500,000 to over $2 million, while condominiums in the area start closer to $270,000. Island Estates attracts boaters, full-time residents, and second-home buyers in roughly equal measure.

Sand Key

Sand Key is a narrow barrier island just south of Clearwater Beach, offering a quieter beachfront alternative with a more residential character. Condominiums are the dominant property type here, and the area is known for Gulf views, beach access, and a somewhat less tourist-heavy atmosphere than the Clearwater Beach core. Sand Key properties require the same careful flood and insurance analysis as any beachfront purchase.

Countryside

Countryside is a planned inland community in the northeastern part of Clearwater, built around Countryside Mall and Countryside Country Club. It is a family-friendly area with good schools, parks, and established streetscapes. Homes in Countryside typically start in the high $200,000s and range upward depending on size and condition. Importantly, Countryside sits largely in FEMA Zone X, meaning significantly lower flood insurance premiums compared to coastal properties. This is a real cost advantage that buyers sometimes overlook when comparing beach vs. inland options.

Northwood Estates and Del Oro

These established inland neighborhoods offer affordable single-family homes for buyers who want to be in Clearwater proper without beach-area prices or flood zone exposure. Northwood Estates and Del Oro are consistently cited among Clearwater’s well-regarded residential areas, appealing to first-time buyers, downsizers, and investors. Median prices in parts of this area have been more accessible than coastal Clearwater, often in the range of the city’s overall median near $300,000.

Downtown Clearwater and the Old Bay District

Downtown Clearwater and the Old Bay District sit along the eastern shore of Clearwater Harbor. The Old Bay District has seen renewed interest from buyers looking for walkability and an urban feel within Clearwater. Median prices in the Old Bay District area have been reported around $532,500, above the broader city median, reflecting the premium buyers place on the waterfront proximity and in-town character of this corridor.

Clearwater Schools and School Zones

Clearwater is served by the Pinellas County School District. School quality and attendance zone boundaries vary significantly across the city, and for many buyers, especially families with children, school zone research is a primary filter for the home search.

Clearwater High School

Clearwater High School is the dominant public high school serving much of Clearwater’s population. Located at 540 S. Hercules Ave., the school serves approximately 1,543 students in grades 9 through 12 with a 15.9:1 student-to-teacher ratio. Clearwater High offers AP coursework, with an AP participation rate of 35%. The school’s history in the community runs back to 1906 and the current Hercules Avenue campus dates to 1954. The Washington Post ranked it the most challenging high school in Pinellas County in 2017 based on AP and IB participation as a share of graduating seniors.

Other Pinellas County High Schools Serving Clearwater

Depending on the specific address within Clearwater, students may also be zoned for Dunedin High School, Countryside High School, or Largo High School. Buyers with school zone concerns should verify the exact attendance zone for any specific property through the Pinellas County Schools website before committing to a purchase. Zone boundaries are subject to change and vary at the street level.

Elementary and Middle Schools

Clearwater is served by numerous Pinellas County elementary and middle schools. GreatSchools ratings for Clearwater schools vary from school to school. Neighborhoods like Countryside tend to feed into schools with higher ratings. Buyers who prioritize school ratings should ask Barrett to run a zone check on any address they are seriously considering. It takes five minutes and prevents a significant disappointment later.

Buying in Clearwater: Waterfront vs. Inland

This is one of the most consequential decisions Clearwater buyers face, and it goes well beyond the simple question of price. Here is how Barrett frames the comparison.

Waterfront and Beach Properties: What to Know

Clearwater Beach, Island Estates, and Sand Key properties carry Gulf and bay views, beach access, and in many cases strong short-term rental income potential. They also carry meaningfully higher insurance costs, stricter lending requirements for flood elevation, and in condos, potential exposure to HOA reserve deficiencies that have become a significant concern across Florida following the Surfside tragedy and new state legislation. Buyers considering Florida beachfront or waterfront condos need to review financials and reserve studies carefully. Barrett walks every buyer through the Florida flood zone and insurance landscape before any coastal offer is made. See our Florida flood zones guide for context, and our flood insurance guide for cost framing.

Inland Clearwater: The Cost Advantage

Inland Clearwater, including Countryside, Northwood, and Del Oro, generally sits in FEMA Zone X, which carries standard homeowners insurance without a separate flood policy requirement in most cases. For buyers on a budget, the difference in total monthly cost between a coastal condo and an inland single-family home of comparable price can be substantial once insurance is fully accounted for. Inland buyers also face fewer short-term restrictions and typically have better school zone access.

Investment and Short-Term Rental Buyers

Clearwater Beach and nearby coastal areas attract buyers seeking short-term rental income. This can be a viable strategy in the right building with the right HOA rules. However, many Clearwater Beach condo buildings have restrictions on rental frequency or minimum rental durations, and some have tightened those rules in recent years. If short-term rental income is part of your investment thesis, Barrett verifies the HOA rental rules for every building you consider before you make an offer. See our investment resources for broader context.

Selling Your Clearwater Home

Selling in Clearwater means understanding which buyer pool your home appeals to and positioning it accordingly. A beach condo markets differently than a Countryside single-family home. Barrett builds a custom strategy for each listing.

Pricing Strategy

Clearwater’s market has seen notable price corrections in the coastal segment, with Clearwater Beach median prices declining year-over-year through portions of 2025 as the broader Florida coastal condo market absorbed the impact of higher insurance costs, new reserve requirements, and a more cautious buyer pool. Inland homes in areas like Countryside have been more stable. Barrett pulls neighborhood-level comps, not just city-wide averages, to price your home accurately.

Presentation and Marketing

Every listing Barrett takes includes professional photography. For coastal and waterfront listings, the right photography is even more important because buyers from out of state, and frequently from out of the country, are making decisions based on digital content before ever visiting in person. Barrett’s marketing plan includes full MLS syndication, targeted digital advertising, and the RE/MAX international referral network, which is particularly valuable for Clearwater Beach properties that attract European and Canadian buyers.

Timing and Preparation

Clearwater’s seasonal market sees stronger buyer activity in the fall and winter months as snowbirds and relocators drive demand. Spring can also be active. If your timeline allows, Barrett can advise on the optimal listing window for your specific property type and neighborhood. Start with a free home valuation to understand where your property sits in the current market.

Clearwater Market Snapshot

The Clearwater market covers a wide range of price points and property types, from sub-$300,000 inland homes to multi-million dollar Gulf-front estates. Here are some reference figures drawn from publicly available 2025 data.

Segment	Reference Price	Note
Clearwater overall median	~$299,000 to $340,000	Varied by source and month, 2025
Clearwater Beach median list	~$725,000 to $828,000	2025 data; prices declined YoY
Island Estates median sale	~$525,000	Last 12 months per available data
Island Estates condos from	~$270,000	Entry-level condo pricing
Countryside / inland range	High $200s and up	Single-family homes
Old Bay District median	~$532,500	Downtown-adjacent area
Avg. days on market	~78 days	City-wide average, 2025

These figures are reference points drawn from publicly available sources. Clearwater’s market moves at the neighborhood and building level. For current pricing relevant to your specific search or property, contact Barrett directly.

For context on neighboring markets, see St. Petersburg, Tampa, and our Clearwater community guide. For buyers considering luxury options, see our luxury real estate resources.

Frequently Asked Questions About Clearwater FL Real Estate

What is the median home price in Clearwater, FL?

The overall Clearwater median home price was reported in the range of roughly $299,000 to $340,000 depending on the source and month during 2025. Clearwater Beach and waterfront areas carry significantly higher medians, with Clearwater Beach listing prices in the $725,000 to $828,000 range during the same period. Inland neighborhoods like Countryside offer more accessible entry points, often starting in the high $200,000s for single-family homes.

Is Clearwater Beach a good investment?

Clearwater Beach has historically generated strong short-term rental interest and benefits from year-round tourism. That said, rising insurance costs, new Florida condo reserve requirements, and a post-peak market correction through 2025 have made the investment calculus more nuanced. The right building and unit can still perform well. The wrong one, with a financially stressed HOA or high insurance exposure, carries real risk. Barrett verifies HOA financials, reserve study status, and rental rules for every condo purchase before an offer is made. See our investment resources for broader guidance.

What are the flood zone risks in Clearwater?

Clearwater Beach, Island Estates, Sand Key, and other coastal areas sit in high-risk FEMA flood zones (typically AE or VE), which require mandatory flood insurance for federally backed mortgages. Flood insurance costs in these zones can range from several hundred to several thousand dollars annually depending on the property’s elevation, flood zone designation, and coverage amount. Inland Clearwater neighborhoods like Countryside, Northwood, and Del Oro are generally in Zone X, which carries no mandatory flood insurance requirement. Our Florida flood zones guide has a full breakdown of zone types and cost implications.

What high schools serve Clearwater, FL?

Clearwater addresses feed into several Pinellas County high schools depending on the specific location. Clearwater High School at 540 S. Hercules Ave. is the primary school for much of the city. Other schools that serve Clearwater zip codes include Countryside High School, Dunedin High, and Largo High. Attendance zone boundaries vary at the street level. Barrett recommends verifying the exact zone assignment for any specific address through the Pinellas County Schools website before purchasing.

Can I buy a short-term rental property in Clearwater?

Short-term rentals are permitted in parts of Clearwater, particularly in beach-adjacent areas, but building-level HOA rules vary significantly. Some Clearwater Beach condo buildings allow nightly or weekly rentals with minimal restrictions. Others have minimum rental periods of 30 or 90 days, which effectively eliminates Airbnb-style income. City of Clearwater and Pinellas County also have licensing requirements for short-term rentals. Barrett checks the HOA rules for every building you consider if rental income is part of your plan. Do not assume a beach address means short-term rentals are allowed.

What is the difference between Clearwater Beach and Island Estates?

Clearwater Beach is a barrier island directly on the Gulf of Mexico, known for white sand beaches, tourism infrastructure, and a vibrant restaurant and nightlife scene. Island Estates sits roughly one mile east of Clearwater Beach, connected by causeway, and is a primarily residential waterfront neighborhood on the Intracoastal and Clearwater Bay. Island Estates generally has a quieter character, more single-family homes, and private dock access. Both areas require careful flood zone and insurance analysis. Prices are comparable in many segments, though the Gulf-front units on Clearwater Beach carry a premium.

Is Clearwater a good place to live for families?

Clearwater offers a range of family-friendly options, particularly in inland areas like Countryside and Northwood. These neighborhoods offer good school access, lower flood insurance costs, more yard space, and a suburban character that suits families well. Clearwater Beach is popular with families too, but the condo-heavy housing stock and tourist environment make it better suited for empty nesters and investors in most cases. Barrett can walk you through the tradeoffs based on your family’s specific priorities, including schools, commute, and budget.

Does Barrett Henry serve buyers outside of Hillsborough County?

Yes. Barrett Henry is a Broker Associate at RE/MAX Collective and serves buyers and sellers throughout the Tampa Bay area, including Pinellas County. His RE/MAX office locations in Tampa, Largo, and Brandon position him well for transactions across both Hillsborough and Pinellas. Clearwater, St. Petersburg, and the beaches are all within his core service area. Contact Barrett to discuss your search.

What should I know about buying a condo in Clearwater?

Florida condo purchases require additional due diligence beyond a standard single-family home transaction. Key items include: reviewing the HOA reserve study (post-Surfside legislation has increased reserve requirements significantly), checking the HOA’s financial health and any pending special assessments, confirming the building’s flood zone and insurance coverage, reviewing rental and pet restrictions, and understanding the HOA’s history of special assessments. Barrett walks every condo buyer through all of these items systematically. A condo that looks affordable at the purchase price can carry substantial ongoing costs if the HOA is underfunded.

How long do homes typically stay on the market in Clearwater?

In 2025, the city-wide average days on market in Clearwater was approximately 78 days. That average masks significant variation: well-priced, well-presented homes in strong locations move faster, while overpriced listings or properties with condition or insurance issues can sit for months. Barrett’s pricing strategy is calibrated to position your home competitively from day one rather than chasing the market downward after a stale listing. Contact Barrett for a free home valuation.