Quick Weston MA MLS Search

Browse All Weston MA Historical Properties for Sale

863 Boston Post Road, Weston
$3,495,000
6 Beds ⋅ 6 Baths ⋅ 73587759 MLS
Privately set on 2.7 acre, this distinguished 16-room landmark residence embodies the timeless elegance and gracious scale of a classic New England estate, thoughtfully enhanced for modern living. A stately entry welcomes you to beautifully preserved architectural details, including dramatic ceilings and windows, exquisite millwork and hardwood floors throughout. Designed equally for grand entertaining and intimate gatherings, the formal living room is anchored by a handsome fireplace, while the richly appointed library, with its own fireplace and built-in bookcases, offers a warm and inviting retreat. A comfortable family room provides a relaxed setting for everyday living. At the heart of the home, the exceptional chef’s kitchen features a generous dining area and beautifully appointed butler’s pantry with direct service to the expansive formal dining room, where a fireplace creates an elegant backdrop for memorable occasions. A first-floor guest bedroom or dedicated home office provides exceptional flexibility. The second floor offers a private bedroom level with a spacious primary with full bath, three additional bedrooms and two more full baths. A separate staircase leads to a private accessory apartment with its own kitchen, sitting room, two bedrooms and full bath—ideal for extended family, guests or staff. Expansive covered porches overlook the heated pool and broad open lawns, creating a beautiful setting for summer entertaining and relaxed outdoor living. Rarely does a property combine such gracious proportions, historic character, versatility and convenience. The 2.7 acres include an approximately 1-acre buildable lot currently going through the town of Weston Flexible Development zoning and subdivision process. Ask listing agent for details.

863 Boston Post Road, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.

73 Chestnut Street, Weston
$9,450,000
7 Beds ⋅ 11 Baths ⋅ 73577074 MLS
Magnificent residence sited on 2.78 private and pristine acres in one of Weston’s most coveted locations. Completely renovated with the highest level of finishes offering every modern amenity. This exceptional home offers estate-like living designed equally for comfortable family life and sophisticated entertaining. The modern designer kitchen anchors the center of the home and flows seamlessly into the sumptuous fireplaced family room with access to private deck overlooking the pool and grounds and spacious screened porch, creating an inviting open floor plan. The formal dining room enhanced by a butler’s pantry is complemented by a well-proportioned formal living. Multiple home offices, a generous mudroom, dog-washing room and a large gym are just a few of the exceptional features this home offers. This home offers two luxurious primary suite options, one on each of first and seconds levels providing exceptional flexibility. All bedrooms are generously sized and feature ensuite baths. The lower level provides dedicated play, craft and billiard spaces along with ample storage. A sleek and private two-bedroom accessory dwelling with separate entrance and two-car garage offers additional accommodations. Resort-like grounds are enhanced with a beautiful pool, well equipped cabana, expansive patios, and private tennis court, creating an extraordinary setting for year-round living and entertaining. The incomparable residence provides the ultimate in private living while offering easy access to Boston and Weston’s renowned schools.

73 Chestnut Street, Weston

Listing courtesy of Listing Agent: Deena Powell from Listing Office: Gibson Sotheby's International Realty.

4 Cherry Brook Road, Weston
$2,075,000
4 Beds ⋅ 3 Baths ⋅ 73575393 MLS
Move-in ready Colonial in one of Weston’s most sought-after cul-de-sac neighborhoods, with sidewalks to Weston Center and the commuter rail. Set on a flat, private 1.39-acre lot near the Cherry Brook ball field, this exceptional home blends timeless architectural character with thoughtful modern updates and a welcoming community known for its block parties. Designed for gracious living and effortless entertaining, the main level features beautiful hardwood floors, an expansive front-to-back living room with fireplace and picture window, private den/office with fireplace, formal dining room with custom built-in, and an updated eat-in kitchen flowing seamlessly into the family room with picture window and fireplace. The light-filled sunroom overlooks a bluestone patio and vast, fenced backyard—perfect for play, gardening, pets, and summer gatherings. Upstairs, the primary suite offers a peaceful retreat with renovated en-suite bath featuring heated floors, hardwood floors, fireplace, and three closets, along with three additional bedrooms and an updated family bath also with heated floors. The finished lower level provides flexible space for a playroom, home gym, media room, or office. Central air, attached two-car garage, abundant natural light, and excellent storage complete the home. Moments to top-ranked Weston schools, boutique shopping and dining, commuter rail, and miles of conservation trails. A rare opportunity to enjoy privacy, community, and convenience in a coveted Weston setting.

4 Cherry Brook Road, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.

118 - 120 Summer Street, Weston
$1,350,000
3 Beds ⋅ 4 Baths ⋅ 73566247 MLS
Rarely does a property offer this combination of history, acreage, versatility and potential. Set on 1.38 picturesque acres, this exceptional antique property includes four separate structures—an expanded main residence, accessory dwelling, remarkable three-story barn, and oversized two-car garage—plus a storage shed and two greenhouses. Formerly used as a farm, the property offers a unique opportunity to create a private estate, homestead or multi-generational retreat.The main house is rich in historic character, featuring wide-plank wood floors, beamed ceilings, a welcoming living room, dining room and home office. The spacious primary suite is a true retreat with a vaulted, beamed ceiling, en suite bath and walk-in closet. Historic details blend beautifully with thoughtful updates, including a newer gas heating system and updated electrical.The accessory house features an eat-in kitchen with abundant cabinetry, comfortable family room, spacious bedroom and walk-in closet. Mini-splits provide efficient heating and cooling. The impressive three-story barn, complete with a full bath and potential bedroom, offers endless possibilities for studio, office, guest space, recreation or additional living space.Renovate, expand or move right in—this one-of-a-kind property invites you to imagine what’s possible. Ask about the $250,000 preservation fund available to buyer.

118 - 120 Summer Street, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.

120 Summer St, Weston
$1,350,000
3 Beds ⋅ 4 Baths ⋅ 73565840 MLS
Rarely does a property offer this combination of history, acreage, versatility and potential. Set on 1.38 picturesque acres, this exceptional antique property includes four separate structures—an expanded main residence, accessory dwelling, remarkable three-story barn, and oversized two-car garage—plus a storage shed and two greenhouses. Formerly used as a farm, the property offers a unique opportunity to create a private estate, homestead or multi-generational retreat.The main house is rich in historic character, featuring wide-plank wood floors, beamed ceilings, a welcoming living room, dining room and home office. The spacious primary suite is a true retreat with a vaulted, beamed ceiling, en suite bath and walk-in closet. Historic details blend beautifully with thoughtful updates, including a newer gas heating system and updated electrical.The accessory house features an eat-in kitchen with abundant cabinetry, comfortable family room, spacious bedroom and walk-in closet. Mini-splits provide efficient heating and cooling. The impressive three-story barn, complete with a full bath and potential bedroom, offers endless possibilities for studio, office, guest space, recreation or additional living space.Renovate, expand or move right in—this one-of-a-kind property invites you to imagine what’s possible. Ask about the $250,000 preservation fund available to buyer.

120 Summer St, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.

64 Country Drive, Weston
$3,495,000
7 Beds ⋅ 7 Baths ⋅ 73515642 MLS
Stately brick-front Colonial nestled on 2.45 spectacular acres in Weston’s highly coveted South Side Estates. A grand foyer welcomes you into a front-to-back living room with a cozy fireplace and an elegant formal dining room. The newly renovated chef’s kitchen is equipped with top-tier appliances, including Wolf gas and induction cooktops, Sub-Zero refrigeration, and a Miele coffee maker, dishwasher, and steam oven. The sunny breakfast area opens to a bright sunroom and an expansive deck, perfect for overlooking idyllic grounds complete with a soothing waterfall and Koi pond. Directly adjacent, the open family room features its own fireplace, alongside a practical mudroom and powder room. Upstairs houses 5 generously sized bedrooms, including a princess suite and 2 primary suites. The primary retreat showcases a luxurious 2025 addition featuring a spa-like steam bath, IR sauna, heated flooring, his-and-her walk-in closets, and a dedicated laundry room. The walkout lower level serves as a private in-law or au-pair apartment, complete with a 6th bedroom, kitchenette, home office, gym, and flexible bonus room. Outdoor living is unmatched, featuring a coveted clay tennis court, mature professional landscaping, a circular driveway, and a 3-car garage. Incredible infrastructure updates include a new roof, a new 7-bedroom septic system, new bathrooms, new mechanicals, and integrated smart switches, lighting, and security. Enjoy peaceful privacy with easy access to Boston and Weston’s top-rated schools. To motivate Buyers, the Seller will entertain a buy down interest rate credit at closing.

64 Country Drive, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Weston Historical Real Estate

Our website features the best real estate search for historical properties available in Weston and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

How much is your home worth?

Get instant property value now!