8 Chestnut St

5,354 Sq. Ft.
$492 / Sq. Ft.
5,354
Sq. Ft.
$492
per Sq. Ft.

Description

Newly constructed 5,366 sq ft luxury home with attached 2 car garage! Featuring 5 bedrooms, 4 full and 2 half bath, and 4 levels of living, discover thoughtful elegance at every turn . The designer kitchen offers high-end appliances including a gas stove, double oven, and wet-bar with beverage fridge. Featuring an open-concept, the kitchen effortlessly flows into the sun-drenched living and dining areas, with home office, first floor bedroom, and large mudroom nearby. Ascend to the 2nd floor to find...Newly constructed 5,366 sq ft luxury home with attached 2 car garage! Featuring 5 bedrooms, 4 full and 2 half bath, and 4 levels of living, discover thoughtful elegance at every turn . The designer kitchen offers high-end appliances including a gas stove, double oven, and wet-bar with beverage fridge. Featuring an open-concept, the kitchen effortlessly flows into the sun-drenched living and dining areas, with home office, first floor bedroom, and large mudroom nearby. Ascend to the 2nd floor to find the spacious primary suite with walk-in closet, stunning bath with soaking tub, and attached deck, along with 3 other bedrooms and laundry. The 3rd floor features a bonus room with 1/2 bath, along with additional flexible space in the finished basement. Outside, the beautifully landscaped yard with cozy fire pit and patio creates the ultimate oasis. Winchester center and commuter rail less than 1 mile away. Don’t miss the chance to make 8 Chestnut home!

Listing Agents

  1. Susan C. McLaren

    Susan C. McLaren

    Alternative Listing Agent

    Compass

    susan.mclaren@compass.com

    P: (617)-605-8348

Property Details for 8 Chestnut Street

Town
Winchester
Area
MA-Winchester
Architectural Style
Colonial
Style
Colonial
Garage Spaces
2
Parking Spaces
4.00
Parking Spaces Total
6
LISTING UPDATED: 08/15/2025 07:30 PM

Property Details for 8 Chestnut Street

StatusSold
MLS #73342518
Days on Market127
Taxes$26,633 / year
HOA Fees-
Compass TypeSingle Family
MLS TypeSingle Family / Detached
Year Built1850
CountyMiddlesex County
Buyer's Agent Compensation2.5%
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Building Information for 8 Chestnut Street

Stories-Year Built1850Building Size-Lot Size0.38 AC / 16,335 SF

Payment Calculator

$15,062 per month

30 year fixed, 6.15% Interest

Principal and Interest

$12,843

Property Taxes

$2,219

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 8 Chestnut Street

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Shopping, Swimming Pool, Tennis Court, Park, Walk/Jog Trails, Golf Course, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Public School, T-Station
  • Current Financing: Conv. Fixed
  • Living Area: 5354.0
  • Color: White
  • SqFt with Basement: Yes
  • Property Attached: No
  • Property Condition: Updated/Remodeled, Remodeled
  • Single Family Type: Detached
  • Waterfront: No
  • Water View: No
  • Year Built Details: Actual
  • Year Built Source: Public Records
Location/School
  • Grade School: Lincoln
  • High School: Winchester Hs
  • Middle School: Mccall
  • Neighborhood: In Town Location
Features
Interior Features
  • Appliances: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Range Hood
  • Basement Features: Partial, Partially Finished
  • Num of Baths: 6.0
  • Num of Full Baths: 4
  • Num of Half Baths: 2
  • Bathrooms Total Decimal: 5.00
  • Bathrooms Total Integer: 6
  • DoorFeatures: French Doors
  • FireplaceFeatures: Living Room
  • FireplaceYN: Yes
  • Fireplaces: 1
  • Flooring: Tile, Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Hardwood, Flooring - Vinyl
  • Interior Features: Bathroom - Full, Bathroom - Tiled With Tub & Shower, Recessed Lighting, Lighting - Sconce, Bathroom - Tiled With Shower Stall, Bathroom - Half, Open Floorplan, Window Seat, Bathroom, Office, Bonus Room, Internet Available - DSL
  • Interior Features: Internet Available - DSL, French Doors
  • Laundry Features: Closet/Cabinets - Custom Built, Flooring - Stone/Ceramic Tile, Electric Dryer Hookup, Recessed Lighting, Remodeled, Washer Hookup, Sink, Second Floor
  • Primary Bath: Yes
  • SpaYN: No
  • Window Features: Insulated Windows
Exterior Features
  • Construction: Frame
  • Exterior Features: Patio, Fenced Yard
  • Exterior Features: Fenced Yard, Patio
  • Fencing: Fenced
  • Lot Description: Gentle Sloping
  • Patio And Porch Features: Patio
Parking Features
  • Attached Garage: Yes
  • Carport: No
  • Covered Spaces: 2.00
  • Garage: Yes
  • Garage Parking: Attached, Garage Door Opener, Paved Drive, Paved Driveway
  • Open Parking: Yes
  • Parking Features: Attached, Garage Door Opener, Paved Drive, Paved Driveway
  • Parking Features: Paved Driveway
Utilities
  • Cooling: Central Air
  • Cooling: Yes
  • Electric: 200+ Amp Service
  • Heating: Forced Air, Natural Gas
  • Heating: Yes
  • Sewer: City/Town Sewer
  • Utility Connections: for Gas Range, for Electric Dryer, Washer Hookup
  • Water: Public
Room Information
Primary Bedroom
  • Room Primary Bedroom Area: 386.666666666
  • Room Primary Bedroom Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Walk-In Closet(s),Flooring - Hardwood,Balcony / Deck,Recessed Lighting,Remodeled
  • Room Primary Bedroom Length: 16.0
  • Primary Bedroom Level: Second Floor
  • Room Primary Bedroom Width: 24.166666666
Bedroom 2
  • Bedroom2 Area: 156.027777777
  • Bedroom2 Features: Walk-In Closet(s),Recessed Lighting,Remodeled
  • Bedroom2 Length: 11.416666666
  • Bedroom2 Level: Second
  • Bedroom2 Width: 13.666666666
Bedroom 3
  • Bedroom3 Area: 176.006944444
  • Bedroom3 Features: Closet,Flooring - Hardwood,Recessed Lighting,Remodeled
  • Bedroom3 Length: 11.416666666
  • Bedroom3 Level: Second
  • Bedroom3 Width: 15.416666666
Bedroom 4
  • Bedroom4 Area: 252.777777777
  • Bedroom4 Features: Bathroom - Full,Closet,Flooring - Hardwood,Recessed Lighting,Remodeled
  • Bedroom4 Length: 11.666666666
  • Bedroom4 Level: Second
  • Bedroom4 Width: 21.666666666
Bedroom 5
  • Bedroom5 Area: 178.208333333
  • Bedroom5 Features: Bathroom - Full,Walk-In Closet(s),Flooring - Hardwood,Recessed Lighting,Remodeled
  • Bedroom5 Length: 11.75
  • Bedroom5 Level: First
  • Bedroom5 Width: 15.166666666
Bathroom 1
  • Bathroom1 Area: 28.875
  • Bathroom1 Features: Bathroom - Half,Flooring - Hardwood,Recessed Lighting,Remodeled,Lighting - Sconce
  • Bathroom1 Length: 5.5
  • Bathroom1 Level: First
  • Bathroom1 Width: 5.25
Bathroom 2
  • Bathroom2 Area: 49.875
  • Bathroom2 Features: Bathroom - Full,Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile,Recessed Lighting,Remodeled
  • Bathroom2 Length: 4.75
  • Bathroom2 Level: Second
  • Bathroom2 Width: 10.5
Bathroom 3
  • Bathroom3 Area: 112.784722222
  • Bathroom3 Features: Bathroom - Full,Bathroom - Tiled With Tub,Bathroom - With Shower Stall,Flooring - Stone/Ceramic Tile,Countertops - Upgraded,Double Vanity,Recessed Lighting,Remodeled,Lighting - Sconce,Soaking Tub
  • Bathroom3 Length: 9.083333333
  • Bathroom3 Level: Second
  • Bathroom3 Width: 12.416666666
Dining Room
  • Dining Room Area: 235.104166666
  • Dining Room Features: Flooring - Wood,Open Floorplan,Recessed Lighting,Remodeled
  • Dining Room Length: 15.416666666
  • Dining Room Level: Main,First
  • Dining Room Width: 15.25
Kitchen
  • Kitchen Area: 237.222222222
  • Kitchen Features: Countertops - Upgraded,Kitchen Island,Wet Bar,Cabinets - Upgraded,Open Floorplan,Recessed Lighting,Remodeled,Stainless Steel Appliances,Gas Stove
  • Kitchen Length: 10.166666666
  • Kitchen Level: Main,First
  • Kitchen Width: 23.333333333
Laundry
  • Laundry Dimen: 9'1X7'9
Living Room
  • Room Living Room Area: 449.166666666
  • Room Living Room Features: Open Floorplan,Recessed Lighting,Remodeled,Tray Ceiling(s)
  • Room Living Room Length: 19.25
  • Room Living Room Level: Main,First
  • Room Living Room Width: 23.333333333
Other Room 1
  • Room Office Area: 94.979166666
  • Room Office Features: Flooring - Hardwood,French Doors,Recessed Lighting,Remodeled
  • Room Office Length: 11.75
  • Room Office Level: First
  • Room Office Width: 8.083333333
Property Information
Property Info
  • Year Round: Yes
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Road Frontage Type: Public
  • Disclosures: PIctures include virtually staged photos.
Tax Information
  • Tax ID: M:005 B:0129 L:0,895588
  • Assessments: $2,401,500
  • Book: 82411
  • Tax Year: 2025
  • Zoning: RDB
Building / Association Information
Living Characteristics
  • Beds Total: 5
Other Building Characteristics
  • Foundation: Concrete Perimeter
  • Cooling Zones: 3
  • Heat Zones: 3
Complex & Association Information
  • Adult Community: No
Market and Agent Information
Sale Info
  • Buyer Broker Comp: 2.5

Property History for 8 Chestnut Street

DateEvent & SourcePriceAppreciation
Jul 31, 2025

Sold

MLS PIN #73342518

$2,635,000
Jul 1, 2025

Under Agreement

MLS PIN #73342518

Jul 1, 2025

Contingent

MLS PIN #73342518

Jun 26, 2025

Price Change

MLS PIN #73342518

$2,790,000
May 14, 2025

Price Change

MLS PIN #73342518

$2,890,000
Mar 6, 2025

Price Change

MLS PIN #73342518

$2,999,000
Mar 6, 2025

Price Change

MLS PIN #73342518

$29,999,000
Mar 6, 2025

Listed (Active)

MLS PIN #73342518

$2,999,000
Feb 3, 2025

Canceled

MLS PIN #73305360

$3,299,000
Oct 23, 2024

Listed (Active)

MLS PIN #73305360

$3,299,000
Jan 29, 2024

Sold

MLS PIN #73193478

$1,400,000
Jan 14, 2024

Contingent

MLS PIN #73193478

Jan 14, 2024

Listed (Active)

MLS PIN #73193478

$1,400,000
Jul 10, 2012

Sold (Public Record)

Public Record #334928740

$1

-51.0% / yr

Jul 1, 1994

Sold (Public Record)

Public Record #88227093

$380,000
Jun 28, 1994

Sold (Public Record)

Public Record #88227081

$20,000
DateEvent & SourcePrice
07/31/2025

Sold

MLS PIN #73342518

$2,635,000
07/01/2025

Under Agreement

MLS PIN #73342518

07/01/2025

Contingent

MLS PIN #73342518

06/26/2025

Price Change

MLS PIN #73342518

$2,790,000
05/14/2025

Price Change

MLS PIN #73342518

$2,890,000
03/06/2025

Price Change

MLS PIN #73342518

$2,999,000
03/06/2025

Price Change

MLS PIN #73342518

$29,999,000
03/06/2025

Listed (Active)

MLS PIN #73342518

$2,999,000
02/03/2025

Canceled

MLS PIN #73305360

$3,299,000
10/23/2024

Listed (Active)

MLS PIN #73305360

$3,299,000
01/29/2024

Sold

MLS PIN #73193478

$1,400,000
01/14/2024

Contingent

MLS PIN #73193478

01/14/2024

Listed (Active)

MLS PIN #73193478

$1,400,000
07/10/2012

Sold (Public Record)

Public Record #334928740

$1

-51.0% / yr

07/01/1994

Sold (Public Record)

Public Record #88227093

$380,000
06/28/1994

Sold (Public Record)

Public Record #88227081

$20,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 8 Chestnut Street

Taxable ValueLand$1,272,700Additions$1,128,800Total$2,401,500
Tax Record2025$26,633 ($2,219 / month)
Home Facts
Beds5Baths2.5Total Finished SqFt5,354 SqFtAbove Grade Finished SqFt5,354 SqFtUnfinished Basement SqFt502 SqFtStories3Lot Size16,335 SqFtStyleSingle Family ResidenceYear Built1850Year Renovated2024ZoningRDBCountyMIDDLESEXAPNWINC M:005 B:0129 L:0Fireplace TypeHas Fireplace

Schools near 8 Chestnut Street

This home is within Winchester School District.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - 6 to 8
Public - 9 to 12
Rating
School
Distance
Lincoln Elementary School
PublicK to 5

McCall Middle School
Public6 to 8

Winchester High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. 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 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., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS 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.