Cliff Road, Wellesley

Cliff Road is one of the best known and prestigious addresses in Wellesley. While the majority of Cliff Road is in Wellesley, the most northern half mile is in Weston. Starting at the intersection of Oak Street and Glenn Road in Weston, Cliff Road heads in a south westerly direction in Weston, then turn 90 degrees heading southeast for another mile and a half, crossing Rte. 9, before coming to an end at Washington Street. 

The homes along Cliff Road in Wellesley are typically large estates consisting of 5 or more bedroom, 4 to 5 baths, and over 5,000 square feet of living space. The houses rest on large lots of a half acre or more. While the homes on Cliff Road vary in age, most have had extensive renovations over the years, and typically sell in the $2 to $4 million range. 

Cliff Road - Current Listings

Cliff Road Wellesley May 27, 2024
Avg. DOM
Avg. $ / Sq.Ft.
Med. List Price
1 Property

Cliff Road Recent Sales1 Property

Address Beds Baths Sq.Ft. List Price Sold Price $/Sq.Ft. Sold Date
15 Woodcliff Rd Wellesley,  MA 02481 15 Woodcliff Rd
Wellesley, MA 02481
6 8 8,430 $4,895,000 $4,850,000 $575.33 5/30/23

Cliff Road Wellesley