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
Sold for $3,450,000
$3,450,000
2 Chestnut St, Winchester, MA 01890
6beds
5,500sqft
Single Family Residence
Built in 2025
0.25 Acres Lot
$3,478,900 Zestimate®
$627/sqft
$7,654 Estimated rent
Home value
$3,478,900
$3.20M - $3.79M
$7,654/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
Mark Donnellan 781-608-9970,
Advisors Living - Winchester 978-423-5235
Bought with:
The Marrocco Group
Coldwell Banker Realty - Lexington
Source: MLS PIN,MLS#: 73333668
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 5
- Full bathrooms: 5
Primary bedroom
- Features: Bathroom - Full, Walk-In Closet(s), Flooring - Hardwood
- Level: Second
- Area: 320
- Dimensions: 20 x 16
Bedroom 2
- Features: Walk-In Closet(s), Flooring - Hardwood
- Level: Second
- Area: 182
- Dimensions: 14 x 13
Bedroom 3
- Features: Bathroom - Full, Walk-In Closet(s), Flooring - Hardwood
- Level: Second
- Area: 154
- Dimensions: 14 x 11
Bedroom 4
- Features: Walk-In Closet(s), Flooring - Hardwood
- Level: Second
- Area: 204
- Dimensions: 17 x 12
Bedroom 5
- Features: Flooring - Hardwood
- Level: Third
- Area: 196
- Dimensions: 14 x 14
Primary bathroom
- Features: Yes
Bathroom 1
- Features: Bathroom - Full, Bathroom - Tiled With Shower Stall
- Level: First
- Area: 40
- Dimensions: 8 x 5
Bathroom 2
- Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall, Soaking Tub
- Level: Second
- Area: 168
- Dimensions: 14 x 12
Bathroom 3
- Features: Bathroom - Full, Bathroom - Tiled With Shower Stall
- Level: Second
- Area: 72
- Dimensions: 12 x 6
Dining room
- Features: Flooring - Hardwood
- Level: First
- Area: 165
- Dimensions: 15 x 11
Kitchen
- Features: Flooring - Hardwood, Countertops - Stone/Granite/Solid, Kitchen Island
- Level: First
- Area: 270
- Dimensions: 18 x 15
Living room
- Features: Flooring - Hardwood
- Level: First
- Area: 320
- Dimensions: 20 x 16
Office
- Features: Flooring - Wall to Wall Carpet
- Level: Basement
- Area: 182
- Dimensions: 14 x 13
Heating
- Central, Electric
Cooling
- Central Air, Heat Pump
Appliances
- Included: Electric Water Heater
- Laundry: Flooring - Stone/Ceramic Tile, Second Floor
Features
- Bathroom - Full, Bathroom - Tiled With Shower Stall, Mud Room, Bedroom, Study, Play Room, Office, Exercise Room
- Flooring: Wood, Flooring - Stone/Ceramic Tile, Flooring - Hardwood, Flooring - Wall to Wall Carpet, Flooring - Wood
- Basement: Full,Partially Finished,Walk-Out Access
- Number of fireplaces: 1
- Fireplace features: Living Room
Interior area
- Total structure area: 5,500
- Total interior livable area: 5,500 sqft
- Finished area above ground: 4,540
- Finished area below ground: 960
Property
Parking
- Total spaces: 4
- Parking features: Attached, Off Street
- Attached garage spaces: 2
- Uncovered spaces: 2
Features
- Patio & porch: Patio
- Exterior features: Patio, Professional Landscaping, Sprinkler System, Decorative Lighting, Stone Wall
Lot
- Size: 0.25 Acres
- Features: Corner Lot
Details
- Parcel number: M:005 B:0132 L:0,895591
- Zoning: RDB
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Concrete Perimeter
- Roof: Shingle
Condition
- Year built: 2025
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $627/sqft
- Tax assessed value: $1,410,400
- Annual tax amount: $15,641
- Date on market: 11/18/2025
Price history
| Date | Event | Price |
|---|---|---|
| 6/26/2025 | Sold | $3,450,000-4.1%$627/sqft |
Source: MLS PIN #73333668 Report a problem | ||
| 4/5/2025 | Contingent | $3,599,000$654/sqft |
Source: MLS PIN #73333668 Report a problem | ||
| 2/9/2025 | Listed for sale | $3,599,000-1.4%$654/sqft |
Source: MLS PIN #73333668 Report a problem | ||
| 11/11/2024 | Listing removed | $3,649,000$663/sqft |
Source: MLS PIN #73302972 Report a problem | ||
| 10/16/2024 | Listed for sale | $3,649,000+130.9%$663/sqft |
Source: MLS PIN #73302972 Report a problem | ||
| 6/11/2024 | Sold | $1,580,000-7%$287/sqft |
Source: MLS PIN #73211061 Report a problem | ||
| 4/18/2024 | Contingent | $1,699,000$309/sqft |
Source: MLS PIN #73211061 Report a problem | ||
| 3/12/2024 | Listed for sale | $1,699,000+179.9%$309/sqft |
Source: MLS PIN #73211061 Report a problem | ||
| 11/30/2009 | Sold | $607,000$110/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $15,641 +2.8% | $1,410,400 +5% |
| 2024 | $15,215 +6.7% | $1,342,900 +11.2% |
| 2023 | $14,256 +3.7% | $1,208,100 +10% |
| 2022 | $13,741 +3% | $1,098,400 +5.7% |
| 2021 | $13,336 +3.6% | $1,039,400 |
| 2020 | $12,878 +11.4% | $1,039,400 +8.8% |
| 2019 | $11,564 +2.8% | $954,900 +3.5% |
| 2018 | $11,244 +2.3% | $922,400 +3.1% |
| 2017 | $10,986 +5.1% | $894,600 |
| 2016 | $10,449 +4.9% | $894,600 +9% |
| 2015 | $9,963 -5.4% | $820,700 -1.3% |
| 2014 | $10,529 -0.3% | $831,700 +0.6% |
| 2013 | $10,558 +4.4% | $826,800 +2.6% |
| 2012 | $10,112 -1.3% | $805,700 -4.8% |
| 2011 | $10,240 +9.4% | $846,300 +4% |
| 2010 | $9,362 +2.1% | $813,400 |
| 2009 | $9,167 +3% | $813,400 -3.4% |
| 2008 | $8,902 +1.3% | $842,200 -1% |
| 2007 | $8,791 +2.9% | $851,000 +3.3% |
| 2006 | $8,542 +5.3% | $823,700 +5.8% |
| 2005 | $8,111 +1.6% | $778,400 +10.9% |
| 2004 | $7,984 +2.8% | $701,600 +2.8% |
| 2003 | $7,768 +17.4% | $682,600 +14.1% |
| 2002 | $6,618 +21.7% | $598,400 +38.7% |
| 2000 | $5,440 -5.6% | $431,500 +9.6% |
| 1999 | $5,762 | $393,600 |
Find assessor info on the county website
Neighborhood: 01890
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Nearby schools
GreatSchools rating
- 9/10Lincoln Elementary SchoolGrades: K-5Distance: 0.4 mi
- 9/10McCall Middle SchoolGrades: 6-8Distance: 0.4 mi
- 10/10Winchester High SchoolGrades: 9-12Distance: 0.8 mi
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Estimated market value
$3,478,900
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Estimated market value
$3,478,900
- Massachusetts
- Middlesex County
- Winchester
- 01890
- 2 Chestnut St
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