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 |