2 Chestnut St, Winchester, MA 01890
Property image
Property image
OFF MARKET

$3,075,700

Trulia Estimate
  • 6 Beds
  • 5 Baths
  • 5,500 sqft (on 0.25 acres)

2 Chestnut St, Winchester, MA 01890

Est. Refi. Payment $19,233/mo*
Refinance Your Home
Currently Off Market - Sold Jun 26, 2025 for $3,450,000

Home Value

Trulia Estimate
$3.08M
Since last month
Increased$56K (+1.8%)
Since last year
Decreased$394K (-11.3%)
Since last sale
Decreased$356K (-10.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +165% in the last 10 years
MonthEstimated value
2026
September 2026$3.09M
August 2026$3.04M
July 2026$3.49M
June 2026$3.44M
May 2026$3.43M
April 2026$3.41M
March 2026$3.44M
February 2026$3.46M
January 2026$3.39M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
29 Ginn Rd, Winchester, MA
0.34
Single-Family Home
$3,799,000
09/02/26
6
7.5
6,000
58 Bacon St, Winchester, MA
0.38
Single-Family Home
$2,030,000
12/01/25
6
5.5
5,791
39 Town Way, Winchester, MA
0.54
Single-Family Home
$3,200,000
05/13/26
6
6
5,709
4 Norwood St, Winchester, MA
0.62
Single-Family Home
$3,242,250
10/17/25
5
4.5
5,250
10 Edgehill Rd, Winchester, MA
0.30
Single-Family Home
$2,200,000
05/05/26
7
3.5
3,926
19 Town Way, Winchester, MA
0.54
Single-Family Home
$2,750,000
04/03/26
5
5.5
5,257
45 Bacon St, Winchester, MA
0.36
Single-Family Home
$2,650,000
04/21/26
7
7
7,043
30 Rangeley Rd, Winchester, MA
0.39
Single-Family Home
$2,300,000
07/21/26
5
3.5
4,744
21 Willowdale Rd, Winchester, MA
0.46
Single-Family Home
$2,170,000
07/31/26
5
3.5
4,591
8 Felsdale Close, Winchester, MA
0.22
Single-Family Home
$1,930,000
01/09/26
4
2.5
3,658

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
8 Chestnut St, Winchester, MA 01890
0.05
$2,672,100
5
5
5,354
Off Market
319 Main St #&-0, Winchester, MA 01890
0.05
-
7
6.5
6,864
Off Market
14 Chestnut St, Winchester, MA 01890
0.09
$2,423,100
5
2.5
3,480
Off Market
23 Lawson Rd, Winchester, MA 01890
0.10
$3,211,200
6
5.5
5,757
Off Market
7 Herrick St, Winchester, MA 01890
0.11
$2,562,400
6
3.5
3,969
Off Market
5 Herrick St, Winchester, MA 01890
0.11
$2,581,900
5
3.5
3,862
Off Market
20 Winslow Rd, Winchester, MA 01890
0.11
$1,938,400
4
4
3,522
Off Market
31 Lawson Rd, Winchester, MA 01890
0.14
$2,474,100
4
3.5
5,218
Off Market
30 Symmes Rd, Winchester, MA 01890
0.13
$1,285,200
5
2
2,341
Off Market
48 Lloyd St, Winchester, MA 01890
0.13
$1,754,900
5
2.5
2,747
Off Market
9 Prospect St, Winchester, MA 01890
0.15
$2,209,600
6
3.5
4,667
Off Market

Local Information

  • Map ViewExplore the area around 2 Chestnut St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2025
0.25 acre lot
5,500 sqft
$559/sqft
2 Car Garage

About this House

What's unique:Open layoutDining roomFirst-floor officePersonalized outdoor experienceLarge open-concept kitchen
Welcome to 2 Chestnut Street, an exquisite new construction home in progress by Mark Stephen Development. Situated off coveted Main Street in one of Winchester’s most sought-after neighborhoods, this residence is thoughtfully designed to blend timeless charm with modern conveniences. The home will feature five spacious bedrooms, five full bathrooms, a first-floor office, and a basement offering flexible space for an additional office, playroom, exercise room, or living area. The open-concept kitchen will include premium appliances, a grand nine-foot island, and custom cabinetry, while the primary suite will boast luxurious his-and-her closets and a spa-like bathroom with a soaking tub and marble-tiled shower. A third-floor bonus space adds versatility. With mature landscaping providing privacy and a spacious patio for outdoor living, this property is conveniently located near Winchester town center, top-rated schools, offers easy access to Boston, and promises an unparalleled lifestyle
2 Chestnut St, Winchester, MA 01890 is a 6 bedroom, 5 bathroom, 5,500 sqft single-family home built in 2025. It last sold for $3,450,000 on Jun 26, 2025 (4% below the $3,599,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,075,700.
Last check for updates: about 5 hours ago
Listed by Mark Donnellan, (781) 608-9970
Advisors Living - Winchester, (978) 423-5235
Bought with: The Marrocco Group, (781) 799-0666, Coldwell Banker Realty - Lexington, (781) 862-2600
Source: MLS PIN, MLS#73333668

Home Details for 2 Chestnut St

Interior Features

Interior Details
Basement: Full,Partially Finished,Walk-Out AccessNumber of Rooms: 15Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 5Number of Bathrooms (full): 5
Dimensions and Layout
Living Area: 5500 Square Feet
Appliances & Utilities
Appliances: Electric Water HeaterLaundry: Flooring - Stone/Ceramic Tile,Second Floor
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central Air,Heat PumpHas HeatingHeating Fuel: Central
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Living RoomHas a FireplaceNo Spa
Windows, Doors, Floors & Walls
Flooring: Wood, Flooring - Stone/Ceramic Tile, Flooring - Hardwood, Flooring - Wall to Wall Carpet, Flooring - Wood
Levels, Entrance, & Accessibility
Floors: Wood, Flooring Stone Ceramic Tile, Flooring Hardwood, Flooring Wall To Wall Carpet, Flooring Wood

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: PatioExterior: Patio, Professional Landscaping, Sprinkler System, Decorative Lighting, Stone WallFoundation: Concrete PerimeterSprinkler System
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 4Parking: Attached,Off Street
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 4540Finished Area (below surface): 960

Property Information

Year Built
Year Built: 2025
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: M:005 B:0132 L:0, 895591

Price & Status

Price
List Price: $3,599,000
Status Change & Dates
Off Market Date: Fri Apr 18 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: Winchester

Building

Building Area
Building Area: 5500 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.25 acres

Offer

Contingencies: Pending P&S

Miscellaneous

BasementMls Number: 73333668Above Grade Unfinished Area: 4540

Price and Tax history

DateEventPrice
Jun 26, 2025
Source: MLS PIN #73333668
Sold
$3,450,000
Apr 5, 2025
Source: MLS PIN #73333668
Contingent
$3,599,000
Feb 9, 2025
Source: MLS PIN #73333668
Listed For Sale
$3,599,000
Nov 11, 2024
Source: MLS PIN #73302972
ListingRemoved
$3,649,000
Oct 16, 2024
Source: MLS PIN #73302972
Listed For Sale
$3,649,000

Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
62
2MoM

Around this home

What Locals Say about Winchester

At least 93 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 88 % Say yards are well-kept

  • 87 % Say people would walk alone at night

  • 85 % Say parking is easy

  • 79 % Say there are sidewalks

  • 79 % Say car is needed

  • 77 % Say it's walkable to restaurants

  • 77 % Say kids play outside

  • 75 % Say streets are well-lit

  • 74 % Say there's holiday spirit

  • 67 % Say they plan to stay for at least 5 years

  • 67 % Say there's wildlife

  • 66 % Say neighbors are friendly

  • 65 % Say it's walkable to grocery stores

  • 64 % Say it's quiet

  • 54 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Diana P.
    "Winchester is the cutest town, perfect for families. There is Town Say, and Enka, and everything is very family oriented. We even have great pubs/restaurants as well as sub shops, Greek food, nail salons, anything you could want in a home town!"
    7
    Flag
  • Dominic
    "Phenomenal public school system beginning from Kindergarten and extremely welcoming to new residents transferring in."
    0
    Flag
  • Stacie
    "Very family oriented. Not a great neighborhood if you don’t have children. Great, easy commute into the city. Not enough good restaurants that aren’t overpriced though. "
    0
    Flag
  • Yjchoi7
    "Very safe neighborhood.there are often summer events on the common. Teenagers can take train into Boston area fairly easily as there are two stops within Winchester. Fells is a great place for summer walks. "
    2
    Flag
  • Luis B.
    "perfect for my family It is livable stores Closer to me Barbershop computer store Restaurants I will love to buy a house in this area "
    2
    Flag
  • Yjchoiyjchoi
    "It’s very quiet and safe generally. Yet it’s close to Boston and Cambridge city life within a few stops of the commuter from Winchester. "
    0
    Flag
  • Tara
    "I have lived in this neighborhood for 25 years. I love it. Everybody is friendly and kind. The crime is minimal and it’s very quiet. "
    2
    Flag
  • Katie41287
    "I’m not afraid to walk home at 11pm, the town is clean and has plenty of events around town, the people are friendly and it is near public transportation. "
    1
    Flag
  • Anna S.
    "Excellent school Easy commute to Boston Downtown Great parks and pond nearby"
    0
    Flag
  • tod g.
    "Lovely town with easy access to Boston and easy getaway to northern New England."
    0
    Flag
  • jfrancis6
    "Family community built around three streets that form a circle that only has traffic of residents. The area borders the Town of Winchester forest that is great for walks and snow shoeing in winter. All homes are large and attract families were children can safely play and bike in the neighborhood. Many homes have residents who grow up in the neighborhood as children and returned to raise their families. A short walk 4/10 of a mile to train station for those who work in Boston a trip that takes 12 minutes with only one stop. Schools in Winchester are among the best in Massachusetts, a primary attraction to the Town. The Town center is only one mile away and has an addition train station there as well. The Mystic lakes are just beyond the train station with a Town beach and boating opportunities. The Town also borders a 2500 acre forest known as the Fells consisting of the Town water supply and miles of hiking or mountain biking."
    0
    Flag
  • marta3467
    "Can see kids playing ball in street; people walking their dog and Horn Pond and several nice restaurants all within walking distance"
    1
    Flag

LGBTQ Local Legal Protections

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.

Frequently asked questions about 2 Chestnut St

  • What is 2 Chestnut St estimated to be worth?
    Trulia's estimated value for 2 Chestnut St in Winchester, MA is $3,075,700.
  • What is the price history for 2 Chestnut St?
    2 Chestnut St in Winchester, MA last sold for $3,450,000 in June 2025.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Winchester?
    Residents describe Winchester, MA as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Winchester, MA.
  • Does 2 Chestnut St have air conditioning?
    Yes, 2 Chestnut St in Winchester, MA has air conditioning.
  • Does 2 Chestnut St have laundry facilities?
    Yes, 2 Chestnut St in Winchester, MA has laundry facilities.

Explore by feature - Pet Friendly

8 pet-friendly rentals in Winchester, MA

Explore by feature - Garage

9 rentals with a garage in Winchester, MA

Explore by feature - Air Conditioning

24 rentals with air conditioning in Winchester, MA

Explore by feature - Pool

12 rentals with a pool in Winchester, MA

Explore by feature - Washer/dryer

29 rentals with a washer/dryer in Winchester, MA

Explore by feature - Outdoor Space

9 rentals with an outdoor space in Winchester, MA

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 2 Chestnut St

Skip to last item
Skip to first item

Homes for sale near 2 Chestnut St

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item