558 Old Windsor Rd, Dalton, MA 01226
OFF MARKET

558 Old Windsor Rd
Dalton, MA 01226

  • 4 Beds
  • 3.5 Baths
  • 3,191 sqft (on 1.90 acres)

$736,400

Trulia Estimate
as of Jun 6, 2026
Est. Refi. Payment $4,535/mo*
Refinance Your Home

$736,400

Trulia Estimate
as of Jun 6, 2026
Est. Refi. Payment $4,535/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,191 sqft
(on 1.90 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Nestled on just under 2 well-manicured acres alongside the meandering Cleveland Brook, this stunning post and beam construction home seamlessly combines the warmth of nature with modern convenience that lends to the perfect blend of privacy and functionality. Currently zoned as a 2-family with a first-floor in-law suite, this home offers lots of flexibility to rent and help pay for your mortgage, offer multigenerational living, or convert the in-law suite into more living space for the main house.

The main house, with 3 bedrooms and 2.5 bathrooms, is warm and inviting with natural wood details throughout the home. The first floor offers a large eat-in kitchen with new appliances, a living room with a pellet stove and floor to ceiling windows overlooking the Cleveland Brook, a sun-filled vaulted dining room, a first-floor primary bedroom with balconied deck, and a full bathroom. Sit and enjoy your coffee on the new trex porch or the large deck on the back of the house with sliding glass doors to both the living room and dining room, perfect for hosting and entertaining. Upstairs, two more bedrooms and a full bathroom offer additional living space and comfort. The partially finished walkout basement invites your creativity making it a flexible space for hobbies, recreation, or storage. The cozy den provides a peaceful space for unwinding or working from home, while ample storage space ensures your belongings have their place. A half bathroom on this level adds to the home's practicality. Access to the two-car garage is a convenient feature, especially during challenging Berkshire winters.

The in-law suite with its own private entrance offers a recently renovated kitchen open to a large dining and living room area with a slider to the front trex deck, a gracious bedroom, full bathroom, and separate laundry facilities. Also accessible through the main house's dining room, it offers an opportunity to reimagine the space if an in-law quarter is not needed. A 2-car garage, house generator, vinyl siding, large shed, newly paved driveway and newer buderus furnace complete this wonderful home that has been lovingly maintained and updated throughout their ownership. Discover the art of living at one with the great outdoors in this beautiful Berkshire home.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from August 30, 2024

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 558 Old Windsor Rd

Interior Features

Interior Details
Basement: Walk-Out Access,Interior Entry,Garage Access,Full,Partially Finished,ConcreteNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Full Bathroom, Half Bathroom, Dining Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3191 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, WasherDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Pellet Stove,Oil,Electric,Boiler,Hot WaterHas CoolingAir Conditioning: ElectricHas HeatingHeating Fuel: Pellet Stove
Fireplace & Spa
Spa: Hot Tub OutdoorHas a Spa
Gas & Electric
Electric: 200 Amp, Circuit Breakers
Windows, Doors, Floors & Walls
Window: Skylight(s)Flooring: Carpet, Ceramic Tile, Wood
Levels, Entrance, & Accessibility
Accessibility: Accessible Bedroom, Accessible Full BathFloors: Carpet, Ceramic Tile, Wood
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Patio / Porch: Porch, DeckOther Structures: Outbuilding
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Other Parking: Garaged & Off-StreetHas a GarageHas an Attached GarageParking Spaces: 2Parking: Paved Drive
Frontage
Waterfront: BrookNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 1985
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Post and Beam,Contemporary
Property Information
Parcel Number: DALT M:221 L:44

Price & Status

Price
List Price: $648,500
Status Change & Dates
Off Market Date: Wed Nov 29 2023Possession Timing: Close Of Escrow

Active Status

MLS Status: Closed

Location

Direction & Address
City: Dalton
School Information
Elementary School: CranevilleJr High / Middle School: Nessacus RegionalHigh School: Wahconah Regional

Building

Building Area
Building Area: 3191 Square Feet

Lot Information

Lot Area: 1.9 Acres

Miscellaneous

BasementMls Number: 241799Water ViewWater View: Water
Last check for updates: about 16 hours ago
Listed by Maggie Gavin, (413) 822-4580
WILLIAM PITT SOTHEBY'S - LENOX
Danielle Giulian, (413) 461-8985
WILLIAM PITT SOTHEBY'S - LENOX
Bought with: Mary Laurin Blair, (413) 441-6648, SIGNATURE ASSOCIATES
Source: BCMLS, MLS#241799

Price History for 558 Old Windsor Rd

DatePriceEventSource
11/29/2023$648,500Sold
BCMLS #241799
11/02/2023$648,500PendingBCMLS #241799
10/18/2023$648,500Listed For SaleBCMLS #241799
09/27/2023ListingRemovedBCMLS #241401
08/25/2023$695,900Listed For SaleBCMLS #241401
04/30/2001$303,750Sold
N/A

Market trends in Dalton

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
14
3MoM
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Property Tax and Assessment

Year2025
Tax$11,612
Assessment$640,500
Home facts updated by county records

Comparable Sales for 558 Old Windsor Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
288 Johnson Rd, Dalton, MA
0.62
Single-Family Home
$532,500
08/27/25
3
1.5
2,043
59 Orchard Rd, Dalton, MA
1.03
Single-Family Home
$485,000
08/29/25
3
2
2,522
224 East St, Dalton, MA
1.12
Single-Family Home
$485,000
10/21/25
4
3.5
2,318
440 E Housatonic St, Dalton, MA
1.10
Single-Family Home
$455,000
07/02/25
4
2.5
1,760
7 Whippoorwill Ln, Dalton, MA
1.47
Single-Family Home
$595,000
08/19/25
4
3
2,875
298 E Housatonic St, Dalton, MA
1.29
Single-Family Home
$359,900
06/01/26
4
2
2,320
64 Marcella Way, Dalton, MA
1.31
Single-Family Home
$405,000
06/12/25
3
2.5
2,503
1157 Main St, Dalton, MA
1.06
Single-Family Home
$299,900
04/14/26
2
1.5
1,544
235 Pleasant St, Dalton, MA
1.76
Single-Family Home
$440,000
09/15/25
4
3
2,973

Nearby homes

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Assigned Schools

These are the assigned schools for 558 Old Windsor Rd.
View nearby schools on GreatSchools
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 Dalton

At least 20 Trulia users voted on each feature.

  • 97 % Say parking is easy

  • 92 % Say it's dog friendly

  • 91 % Say yards are well-kept

  • 85 % Say kids play outside

  • 85 % Say people would walk alone at night

  • 83 % Say there's holiday spirit

  • 81 % Say streets are well-lit

  • 79 % Say car is needed

  • 77 % Say there are sidewalks

  • 74 % Say there's wildlife

  • 70 % Say it's walkable to restaurants

  • 70 % Say they plan to stay for at least 5 years

  • 65 % Say neighbors are friendly

  • 64 % Say it's quiet

  • 41 % Say there are community events

  • 10 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Alicia T.
    "Not much traffic which is nice.Buses are available if needed and comes to my front door.Finding apartments is tough because no one ever moves it seems."
    3
    Flag
  • Caitlin P.
    "Dalton is a great town to raise a family - nice playground, schools, library, and neighbors. It's quiet but close to the city of Pittsfield, where there are restaurants, museums, theater, and other cultural attractions. "
    4
    Flag
  • Metaleater45
    "I just moved into the area but it seems really homely and a great place to raise a family.And also everything is close by or a short bike ride away."
    4
    Flag
  • Kristie B.
    "Nice small town. A new high school will be built soon. There are many community events and resources for children like sports and summer activities "
    3
    Flag
  • Mark A. K. J.
    "Everything is near by wether in town or into coatsville in pittsfield . The town is small and friendly , great community support"
    2
    Flag
  • Mark A. K. J.
    "Our neighborhood is special with a tight community and we take crime and bad acts seriously here. Everyone always looks out for another "
    2
    Flag
  • Mark a. K. J.
    "This neighborhood is full of polite and nice people. All friendly and willing to extend a helping hand. Lots of kids and kid friendly street. "
    2
    Flag
  • Tayseer A.
    "I am living in this neighborhood for 3 years and I love it. I already made friendship with 3 families. Very quite neighborhood and close to shops however you need a car to go around. "
    3
    Flag
  • Julieluvs4
    "It’s friendly and safe, we all look out for one another. The park and school are within walking distance."
    0
    Flag
  • Donnavirg
    "I’ve lived in this neighborhood for 38 years. It’s a quiet place and neighbors are friendly. There is a wide range of wildlife. "
    0
    Flag

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Apartments for Rent

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Homes for sale near 558 Old Windsor Rd

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Off Market Homes Near 558 Old Windsor Rd

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IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed to be reliable but not guaranteed.
The data relating to real estate for sale on this website comes from Berkshire County Board of Realtors and the Broker Reciprocity Program. Copyright 2026 Berkshire County Board of Realtors. All rights reserved.

Homes for rent near 558 Old Windsor Rd

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558 Old Windsor Rd, Dalton, MA 01226 is a 4 bedroom, 4 bathroom, 3,191 sqft single-family home built in 1985. This property is not currently available for sale. 558 Old Windsor Rd was last sold on Nov 29, 2023 for $648,500 (0% higher than the asking price of $648,500). The current Trulia Estimate for 558 Old Windsor Rd is $736,400.