53 Windsor Rd

Wellesley MA 02481

3272 sq. ft.

23694 sq. ft.

Single-Family

Last sold for $2,900,000

Debi Benoit, last sold this property on 24 July 2025 after 56 days on market.

Overview

Settled in the heart of Wellesley’s coveted Country Club neighborhood, 53 Windsor Road is an enchanting, thoughtfully updated Cape-style home that blends classic charm with modern comfort. The open floor plan features spacious sunlit rooms, including a welcoming living room with beamed ceiling and oversized fireplace that flows seamlessly into a formal dining room adorned with large picture windows. The kitchen with quartz counter tops and high end appliances boasts a central island, hardwood floors and a generous eat-in area with access to a deck - perfect for outdoor living. A bright family room with gas fireplace overlooks the beautifully landscaped level grounds. Upstairs find a lovely primary suite and 2 additional bedrooms with 2 baths. A finished lower level adds versatility with a guest suite with full bath and a playroom or exercise room. Ideally located close to town, the train, and shops, this home is a rare opportunity in one of Wellesley’s most desirable locations!

Features

4 bedrooms

5 bathrooms

4 carspaces

2 garage spaces

3272 sq. ft. floor area

23694 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Wellesley over the last 12 months, the estimated median property value of 53 Windsor Rd is $2.24m.

Median value

$2.24m

Estimated value range

$1.34m - $5.1m

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 53 Windsor Rd

2025

Sold

$2,900,000

24 Jul 2025 by Debi Benoit, of William Raveis R.E. & Home Services

2013

Sold

$1,191,000

29 Jul 2013 by Debi Benoit, of Benoit Mizner Simon & Co. - Wellesley - Central St

2009

Sold

$1,035,000

01 Oct 2009 by Mary Duffy, 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.