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Christopher L Cheshire

Christopher L Cheshire
Real Estate Agent (Salesperson)
Saint Petersburg FL

Salesperson (FL: 3507071)

7 years experience

REALTOR® 1 Active Listings Serves Pinellas County, FL
View on Realtor.com

Contact Information

Brokerage
Dalton Wade Inc

Office Website
Office Address
260 1st Ave S Ste 200
Saint Petersburg, FL  33701
(Pinellas County)
Office Phone
888-668-8283
Office Fax
Mobile
352-446-6174
Email
ches*******@*****.com
Show Email for $5
Website

Service Areas

Fruitland Park: FL The Villages: FL Lady Lake: FL Wildwood: FL Oxford: FL Coleman: FL Leesburg: FL Silver Lake: FL Lisbon: FL Haines Creek: FL Mascotte: FL Groveland: FL Tavares: FL Deer Island: FL Eustis: FL Mid Florida: FL Tangerine: FL Mount Dora: FL Zellwood: FL

About Christopher Cheshire

Chris, originally from Long Island, New York, discovered his passion for real estate at the age of 20 when he purchased his first home. Since that pivotal moment, he has engaged in numerous transactions, including buying, selling, flipping, and renting properties, establishing himself as a knowledgeable expert in the local market.

For the past 16 years, Chris has also owned a medical practice in The Villages, which has afforded him valuable insights into the community's perspectives on real estate. His role as Mayor of Fruitland Park further enhances his understanding of the market dynamics.

With a commitment to straightforward communication and exceptional customer service, Chris is dedicated to helping clients successfully sell their current homes or find the dream home they have always envisioned.

Pinellas County, FL Real Estate Market Analysis (Single Family Homes)

$838,520
Avg. Listing Price
From Christopher's portfolio
3.2 / 2.4
Avg. Beds/Baths
Typical property size
1,910 sf
Avg. Square Footage
Interior living space
5556
Active Listings
Current inventory

Pinellas County's real estate market stands out as one of Florida's most dynamic and densely populated markets, encompassing a peninsula surrounded by Tampa Bay and the Gulf of Mexico. This unique geography creates distinct micro-markets ranging from waterfront luxury properties to urban condominiums and suburban family neighborhoods. The county's 21,550 actively licensed real estate agents reflect the intense competition and high transaction volume that characterize this coastal market.

What makes Pinellas County particularly fascinating is its compact size combined with extraordinary diversity in property types and price points. From the bustling downtown St. Petersburg market to the beach communities of Clearwater and Indian Rocks Beach, agents here must navigate everything from historic bungalows to high-rise condos and waterfront estates. The fact that all 21,550 agents maintain current email addresses demonstrates the market's tech-savvy approach to business communications.

Major Pinellas County, Florida Real Estate Markets

St. Petersburg dominates as the county's largest market, experiencing a remarkable transformation with its revitalized downtown core, thriving arts district, and expanding job market. The city's diverse neighborhoods range from the historic Kenwood area to the waterfront luxury of Snell Isle. Clearwater represents the second major market hub, particularly strong in vacation rentals and second homes due to its renowned beaches and tourism infrastructure.

Smaller but significant markets include Dunedin with its charming downtown and spring training appeal, Belleair and Belleair Bluffs for luxury residential properties, and Largo representing more affordable family housing options. Coastal communities like Redington Beach, Indian Shores, and Treasure Island create specialized markets focused on vacation properties and waterfront living, each requiring agents with specific local expertise.

Market Dynamics and Geographic Complexity

Pinellas County's real estate market operates with unusual intensity due to limited land availability and continuous development pressure. The peninsula's geography creates natural boundaries that drive property values and influence development patterns differently than typical mainland markets. Waterfront access, flood zones, and hurricane considerations play outsized roles in property valuations and buyer decisions.

The market experiences significant seasonal fluctuations driven by snowbird migration patterns and vacation rental demand. This creates complex inventory cycles where agents must understand both permanent resident needs and temporary resident preferences. The high concentration of agents relative to land area means specialization becomes crucial, with many focusing on specific neighborhoods, property types, or client demographics.

Why Businesses Need Pinellas County, Florida Agent Contact Data

The concentration of 21,550 agents in a relatively compact geographic area creates exceptional opportunities for businesses serving the real estate industry. Mortgage lenders, insurance companies, home inspectors, and construction contractors can efficiently reach a large number of active professionals within a defined market area. The high transaction volume and property values in Pinellas County translate to agents with substantial purchasing power and frequent service needs.

Having verified email contacts for all active agents enables targeted marketing campaigns based on geographic specialization, property type focus, or brokerage affiliation. Title companies can reach closing-focused agents, while luxury service providers can target waterfront and high-end specialists. The market's seasonal nature also creates opportunities for businesses offering temporary or seasonal services to time their outreach effectively.

Current Property Listings

As of 1/31/2026, Christopher Cheshire has 1 property for sale in Saint Petersburg and surrounding areas.

$865,000

Listed 2025-11-11

4239 Deskin Ln
The Villages, FL  32163

Beds: 3.0
Baths: 2.0
Sq Ft: 1,925
Lot: 8,276 sf
Single Family Map
View Full Details

Current Property Rentals

Christopher Cheshire currently has no rental properties available in Saint Petersburg and surrounding areas. Check back later.