74 Chestnut St, Weston, MA 02493
OFF MARKET

74 Chestnut St
Weston, MA 02493

  • 5 Beds
  • 3.5 Baths
  • 3,112 sqft (on 2.35 acres)

$1,818,300

Trulia Estimate
as of Jul 7, 2026

$1,818,300

Trulia Estimate
as of Jul 7, 2026
5 Beds
3.5 Baths
3,112 sqft
(on 2.35 acres)

Local Information

  • Map ViewExplore the area around 74 Chestnut St.
  • Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Welcome to this charming 5-bedroom, 4-bathroom Colonial estate, gracefully located on a sprawling 2.35-acre lot. This home seamlessly blends historic charm with modern convenience. Step inside to find original hardwood floors, custom built-ins, and a warm, inviting atmosphere. The spacious gourmet kitchen features updated appliances, granite countertops, and an eat-in area perfect for casual dining. A formal dining room and multiple living areas, including a family room with a fireplace, offer ample space for entertaining and flexible living areas. The primary suite boasts an en suite bath while additional bedrooms are generously sized. Outside, mature trees and a fenced in yard create a serene backdrop, with a large deck ideal for gatherings. This remarkable property offers both privacy and an incredible opportunity to create your own dream home in one of Weston's most sought-after locations!
74 Chestnut St, Weston, MA 02493 is a 5 bedroom, 4 bathroom, 3,112 sqft single-family home built in 1881. It last sold for $1,828,000 on Apr 10, 2025 (2% above the $1,795,000 asking price). It is currently off market. The Trulia Estimate is $1,818,300, with a rent estimate of $7,125/month.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
172 days ago

Home Details for 74 Chestnut St

Interior Features

Interior Details
Basement: Walk-Out AccessNumber of Rooms: 11Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3112 Square Feet
Appliances & Utilities
Utilities: for Gas Range, Washer HookupAppliances: Oven, Dishwasher, Microwave, Range, Refrigerator, Freezer, Wine RefrigeratorDishwasherLaundry: In Basement,Washer HookupMicrowaveRefrigerator
Heating & Cooling
Heating: Baseboard,Natural GasHas CoolingAir Conditioning: Window Unit(s)Has HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 2Fireplace: Family RoomHas a FireplaceNo Spa
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Window: ScreensFlooring: Tile, Carpet, Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Hardwood
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood, Flooring Stone Ceramic Tile, Flooring Hardwood

Exterior Features

Exterior Home Features
Roof: WoodPatio / Porch: DeckFencing: FencedExterior: Deck, Rain Gutters, Screens, Fenced YardFoundation: Concrete Perimeter
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 4No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 6Parking: Detached,Garage Door Opener,Garage Faces Side,Paved Drive,Off Street,Paved
Frontage
Road Frontage: PublicNot on Waterfront
Water & Sewer
Sewer: Private Sewer
Finished Area
Finished Area (above surface): 3112Finished Area (below surface): 1556

Property Information

Year Built
Year Built: 1881
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Not Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: M:031.0 L:0011 S:000.0, 868178

Price & Status

Price
List Price: $1,795,000
Status Change & Dates
Off Market Date: Fri Mar 14 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: Weston
School Information
Elementary School: WestonJr High / Middle School: WestonHigh School: Weston

Building

Building Area
Building Area: 3112 Square Feet

Community

Community Features: Public Transportation, Shopping, Walk/Jog Trails, Public SchoolNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 2.3474 Acres

Offer

Contingencies: Pending P&S

Miscellaneous

BasementMls Number: 73342813Above Grade Unfinished Area: 3112

Additional Information

Public TransportationShoppingWalk/Jog TrailsPublic School
Last check for updates: about 17 hours ago
Listed by Debi Benoit, (617) 962-9292
William Raveis R.E. & Home Services, (781) 235-5000
Bought with: Amy Caffrey, (508) 479-4542, Compass, (781) 365-9954
Source: MLS PIN, MLS#73342813

Price History for 74 Chestnut St

DatePriceEventSource
04/10/2025$1,828,000Sold
MLS PIN #73342813
03/10/2025$1,795,000PendingWilliam Raveis Real Estate, Mortgage & Insurance #73342813
03/10/2025$1,795,000ContingentMLS PIN #73342813
03/07/2025$1,795,000Listed For SaleMLS PIN #73342813
08/04/1997$695,000Sold
N/A

Market trends in Weston

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
70
14MoM
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Property Tax and Assessment

Year2025
Tax$17,265
Assessment$1,555,400
Home facts updated by county records

Comparable Sales for 74 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
142 Wellesley St, Weston, MA
0.58
Single-Family Home
$1,930,000
08/22/25
4
3
3,760
22 Chadwick Rd, Weston, MA
0.25
Single-Family Home
$3,350,000
08/29/25
5
5
6,252
137 Wellesley St, Weston, MA
0.58
Single-Family Home
$2,600,000
11/17/25
5
3.5
5,100
100 Chestnut St, Weston, MA
0.22
Single-Family Home
$7,255,000
10/02/25
5
6.5
8,205
823 Boston Post Rd, Weston, MA
1.03
Single-Family Home
$1,972,500
06/02/26
5
2.5
3,847
19 Warren Ln, Weston, MA
0.97
Single-Family Home
$1,500,000
12/11/25
4
3
2,667
148 Highland St, Weston, MA
0.41
Single-Family Home
$6,500,000
07/15/25
5
8
11,412
48 Golden Ball Rd, Weston, MA
0.43
Single-Family Home
$1,275,000
11/21/25
3
2.5
1,800
180 Highland St, Weston, MA
0.46
Single-Family Home
$6,600,000
03/31/26
5
7.5
11,300

Nearby homes

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Assigned Schools

These are the assigned schools for 74 Chestnut St.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Weston

At least 28 Trulia users voted on each feature.

  • 90 % Say car is needed

  • 85 % Say it's dog friendly

  • 82 % Say it's quiet

  • 80 % Say parking is easy

  • 77 % Say people would walk alone at night

  • 76 % Say there's holiday spirit

  • 74 % Say they plan to stay for at least 5 years

  • 73 % Say yards are well-kept

  • 71 % Say there's wildlife

  • 52 % Say kids play outside

  • 50 % Say neighbors are friendly

  • 44 % Say there are community events

  • 38 % Say there are sidewalks

  • 33 % Say it's walkable to grocery stores

  • 29 % Say streets are well-lit

  • 26 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Woman
    "It’s a Commuter’s dream. 3 minutes to the Pike or 128, Rt. 30, 20, or 9. 2 acres tucked in. Very convenient & private. "
    0
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  • marc
    "I like in particular the BBQ in the June/July timeframe. Many events are also organized with different themes such as the old,car’,contest."
    3
    Flag
  • Marc
    "Some nice trails to take your dog along with easy access. Plenty of space in the center of town too where you can do long walks. Many people have them which is a plus. "
    0
    Flag
  • Marc d. g.
    "Commute is rather easy since I work in waltham. Best time is to go to work either at 7am or after 9am. The return to home is usually a bit crowded in the 4-6 window but alternative roads exist."
    1
    Flag
  • suez
    "Weston is perfect for families. Excellent schools and this area is a true neighborhood of the old style. Houses are spaced far apart but connected by trials in the abundant conservation land. The neighbors are connected by a love of privacy and nature. They have specifically sought out an area close to Boston that still feels like you are in rural Massachusetts. A mix of historic homes and new modern works well , and the community is united by a love of this very unique environment. We are close to all the amenities of a city yet a world away. You will have to drive to restaurants and shopping and there is no public transportation but you will not have to pack up and vacation in NH or VT, you will live that life everyday and still be 25 minutes from downtown Boston."
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  • frkmus
    "Open land, a community playground for all homeowners on Kendal Common Rd. and Ellis Rd., allows children to play free of traffic in their virtually private domain. With 20 homes on 40 acres, all constructed in the 1950's, all designed by three architects, this area is unique for many reasons, not the least of which the total absence of fences has for over sixty years firmly implanted a communal spirit among all participating homeowners. The entire land mass is away from main thoroughfares on two virtually private roads; a special haven for young and old alike. Here is where we live and brought up our children."
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Apartments for Rent

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8 pet-friendly rentals in Weston, MA

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Homes for sale near 74 Chestnut St

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Off Market Homes Near 74 Chestnut St

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The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing 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 or leasing. 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 set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.