44 Whiting Road

Wellesley MA 02481

7632 sq. ft.

23328 sq. ft.

Single-Family

Last sold for $5,100,000

Debi Benoit, last sold this property on 30 September 2026 after 33 days on market.

Overview

Welcome to 44 Whiting Road, an exceptional residence set within Wellesley’s coveted Country Club neighborhood. Built in 2009 by renowned builder McLaughlin/DeBenedictis, this distinguished five bedroom, six full bath center entrance Colonial offers three thoughtfully designed levels of refined living. An inviting grand foyer sets the tone for the stunning open-concept floor plan, anchored by a custom designed gourmet kitchen appointed with high-end appliances, marble countertops, and a generous center island. The kitchen flows effortlessly into a sunlit breakfast room with expansive picture windows and a gracious family room, where a stone-front gas fireplace provides a warm focal point and frames views of the bluestone terrace and beautifully landscaped grounds. A handsome wood-paneled office, elegant formal living room, formal dining room and well-appointed butler’s pantry further enhance the main level.The second floor features four en-suite bedrooms, including a luxurious primary suite with marble bath and a private sitting room. The third floor offers an additional bedroom, full bath, and cedar closet, providing extra flexibility for guests, a bonus room, or private retreat. The lower level is equally impressive, with a spacious recreation room, exercise room, full bath with steam shower, and abundant storage. Outside, the private grounds and bluestone terrace create an inviting setting for both quiet relaxation and sophisticated entertaining. Ideally situated near the Wellesley Country Club and golf, with convenient access to the town’s renowned shops and restaurants. A truly not-to-be-missed opportunity!

Features

5 bedrooms

8 bathrooms

5 carspaces

3 open car spaces

2 garage spaces

7632 sq. ft. floor area

23328 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Wellesley over the last 12 months, the estimated median property value of 44 Whiting Road is $2.92m.

Median value

$2.92m

Estimated value range

$1.67m - $5.5m

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Wellesley. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 44 Whiting Road

2026

Sold

$5,100,000

30 Sep 2026 by Debi Benoit, of William Raveis R.E. & Home Services

2002

Sold

$1,660,000

29 Apr 2002 by Ginny Murray, of Coldwell Banker Residential Brokerage - Wellesley - Central St.

1996

Sold

$940,000

12 Apr 1996 by Barbara Olmsted, of Hammond Residential

Happy sellers in Wellesley

We have insufficient information to provide an overview of customer satisfaction for Wellesley. Viewing the agent profiles, reviews and sales for Wellesley can provide insights for this location.