You don't have to be a Sarasota native to grasp the cachet of living here. The siren call of these coastal neighborhoods dates back to 1875, when Richard Cunliff, a citrus grower and one of Sarasota's early pioneers, built the first house in Bayview Heights, Sarasota's oldest neighborhood. In fact, his namesake street, Cunliff Lane, was Sarasota's first Main Street, where the building that housed Sarasota's first post office still stands.

Today, Sarasota's historic West of Trail touts the most sought-after residential neighborhoods, including Bay Point Park, Harbor Acres, Avondale, McClellan Park, Bayview Heights, Cherokee Park, the Flower Streets, Granada and Oyster Bay.

As Sarasota grows to the east, the allure of West of Trail grows evermore.

Facts of the Sarasota West of Trail You Should Know:

Total single-family homes: 1,952, 100 percent
Homes $500,000-plus: 1,391, 71 percent
Homes $750,000-plus: 786, 40 percent
Homes $1 million-plus: 499, 25 percent
Homes for sale: 146, 7 percent

Oldest House: 2525 Pleasant Place

Richard Cunliff's two-story house at 2525 Pleasant Place is the oldest home in Sarasota County. It was recently renovated and is still used as a residence. It is also on the National Registry of Historic Places.

Address: 2525 Pleasant Place
Neighborhood: Bayview Heights
Lot size: 12,500 square feet; .28 acre
Home size: 3,648 square feet under a/c; 5,486 square feet total
Year built: 1874; 2004 remodel
Last sale: 2016, $899,900

Newest House: 1333 Vista Drive

The newest addition to Sarasota’s West of Trail neighborhood has an impressive pedigree—the result of a creative collaboration between home designer Brian Phipps, interior designer Tanya Burley and Eason Builders, whose artistic vision lavishes love on the home via nuanced elegance, eclectic accents and custom finishes hand-crafted by local artisans. The style is New Traditional. The result is an extremely classic home with everlasting appeal.

Address: 1333 Vista Drive
Neighborhood: Harbor Acres
Lot size: 24,252 square feet; .56 acre
Home size: 5,768 square feet under a/c; 8,682 square feet total
Year built: 2019
List price: $5.99 million 

Biggest House: 1420 Bay Point Drive

Located in Bay Point Park, the largest home West of Trail has an astounding 34,070 square feet – 16,014 of which are air-conditioned. Built by former Representative Katherine Harris in 2012, the palatial waterfront mansion has been described as a "French-inspired mini palace." Bay Point Park is the closest West of Trail neighborhood to downtown. It's small, exclusive and home to some of the most prominent Sarasota's, including Katherine Harris and the Lindsay family, who used to own the Herald-Tribune.

Address: 1420 Bay Point Drive
Neighborhood: Bay Point Park
Lot size: 41,593 square feet; .95 acre
Home size: 16,014 square feet under a/c; 34,070 square feet total
Year built: 2012
Last sale: 2003; $3.8 million 

Smallest House: 1642 Bahia Vista Street

At 668 square feet, the smallest home West of Trail is not quite as minuscule as a tiny house, but it comes close. However, the location is grand. Tucked behind a wooden fence within an old oak grove, these homeowners are privileged to live within walking distance of Selby Gardens, Burns Court, Towles Court, Island Park, Downtown Sarasota, Sarasota Memorial Hospital, Southside Village and a great many restaurants, cultural amenities, shops and services.

Address: 1642 Bahia Vista St.
Neighborhood: Hudson Bayou
Lot size: 8,850 square feet; .20 acre
Home size: 626 square feet under a/c; 668 square feet total
Year built: 1926; 1986 remodel
Last sale: 2002; $225,000 

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Peter G. Laughlin
Broker-Associate
Premier Sotheby's International Realty
941.356.8428
Link: tel:19413568428
PeterGLaughlin.com