Extreme West of Trail: From This Old House to Not So Tiny House

Extreme West of Trail: From This Old House to Not So Tiny House

You don’t have to be a Sarasota native to grasp the cachet of living in Sarasota’s West of Trail. 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.

West of Trail Facts You Should Know

Total Single Family Homes 1,946 100%
Homes $500,000+ 1,387 71%
Homes $750,000+ 802 41%
Homes $1,000,000+ 538 28%
Homes for Sale 54 3%

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 sq. ft. / 0.28 acre
Home Size 3,648 sq. ft. A/C / 5,486 sq. ft. Total
Year Built 1874 (2004 remodel)
Last Sale 2016: $790,000

Newest House: 1555 Sandpiper Lane

From award-winning Allegra Homes, this coastal contemporary residents is infused with an atmosphere of sophistication and refinement. You’ll want to take in each and every nuance — features like incredible work-of-art ceilings with dramatic accents, stone-backed wall behind the fireplace, designer free-standing tub in master bath, great room with wall of PGT windows and sliders, professional kitchen with every accessory at your fingertips.

Address 1555 Sandpiper Lane
Neighborhood Paradise Shores
Lot Size 14,784 sq. ft. / 0.34 acre
Home Size 3,498 sq. ft. A/C / 5,235 sq. ft. Total
Year Built 2020
Offered At $2,292,000

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 sq. ft. / 0.95 acre
Home Size 16,014 sq. ft. A/C / 34,070 sq. ft. Total
Year Built 2012
Last Sale 2003: $3,800,000

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 Street
Neighborhood Hudson Bayou
Lot Size 8,850 sq. ft. / 0.20 acre
Home Size 626 sq. ft. A/C / 668 sq. ft. Total
Year Built 1926
Last Sale 2002: $225,000


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