558 Old Windsor Rd, Dalton, MA 01226
Property image
Property image
OFF MARKET

$730,200

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

558 Old Windsor Rd, Dalton, MA 01226

Est. Refi. Payment $4,520/mo*
Refinance Your Home
Currently Off Market - Sold Nov 29, 2023 for $648,500

Home Value

Trulia Estimate
$730K
Since last month
Decreased$7K (-1%)
Since last year
Increased$26K (+3.6%)
Since last sale
Increased$82K (+12.7%)
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 +107% in the last 10 years
MonthEstimated value
2026
August 2026$731K
August 2026$731K
July 2026$738K
June 2026$742K
May 2026$736K
April 2026$727K
March 2026$721K
February 2026$709K
January 2026$706K
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
191 Fox Rd, Dalton, MA
0.67
Single-Family Home
$575,000
08/28/26
3
2
3,542
224 East St, Dalton, MA
1.12
Single-Family Home
$485,000
10/21/25
4
3.5
2,318
230 E Housatonic St, Dalton, MA
1.39
Single-Family Home
$457,500
07/21/26
3
2
2,848
32 Marcella Way, Dalton, MA
1.33
Single-Family Home
$542,000
06/30/26
4
2.5
2,540
96 Anthony Rd, Dalton, MA
1.38
Single-Family Home
$510,000
07/23/26
3
2
2,310
298 E Housatonic St, Dalton, MA
1.29
Single-Family Home
$359,900
06/01/26
4
2
2,320
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
1130 Main Dalton Rd, Windsor, MA
1.61
Single-Family Home
$425,000
08/14/26
4
2
2,616

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
511 Old Windsor Rd, Dalton, MA 01226
0.11
$352,100
3
1.5
1,638
Off Market
471 Old Windsor Rd, Dalton, MA 01226
0.18
$284,900
4
1
1,826
Off Market
720 Old Windsor Rd, Dalton, MA 01226
0.30
$692,300
3
2.5
3,279
Off Market
288 Johnson Rd, Dalton, MA 01226
0.62
$548,100
3
1.5
2,043
Off Market
191 Fox Rd, Dalton, MA 01226
0.67
$575,000
3
2
3,542
Recently Sold
190 Fox Rd, Dalton, MA 01226
0.74
$150,000
-
-
-
Recently Sold
163 Cleveland Rd, Dalton, MA 01226
0.79
$825,000
5
3
3,210
For Sale
30 Ridgeview Dr, Hinsdale, MA 01235
1.01
$617,500
4
2.5
2,642
Off Market
18 Diamond Ter, Dalton, MA 01226
0.97
$278,900
3
1
925
Off Market
12 Diamond Ter, Dalton, MA 01226
0.97
$298,900
4
1
1,176
Off Market
14 Pease Ave, Dalton, MA 01226
0.98
$246,000
3
1
981
Off Market

Local Information

  • Map ViewExplore the area around 558 Old Windsor Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1985
Lot Size
1.9 acres
Living Area
3,191 sqft
Price/Sqft
$229
Parking
2 Car Garage

About this House

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.
558 Old Windsor Rd, Dalton, MA 01226 is a 4 bedroom, 4 bathroom, 3,191 sqft single-family home built in 1985. It last sold for the $648,500 asking price on Nov 29, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $730,200, with a rent estimate of $5,014/month.
Last check for updates: about 4 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

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

Price and Tax history

DateEventPrice
Nov 29, 2023
Source: BCMLS #241799
Sold
$648,500
Nov 2, 2023
Source: BCMLS #241799
Pending
$648,500
Oct 18, 2023
Source: BCMLS #241799
Listed For Sale
$648,500
Sep 27, 2023
Source: BCMLS #241401
ListingRemoved
Aug 25, 2023
Source: BCMLS #241401
Listed For Sale
$695,900

Market trends in Dalton

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
24
4MoM

Around this home

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

LGBTQ Local Legal Protections

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.

Frequently asked questions about 558 Old Windsor Rd

  • What is 558 Old Windsor Rd estimated to be worth?
    Trulia's estimated value for 558 Old Windsor Rd in Dalton, MA is $730,200.
  • What is the price history for 558 Old Windsor Rd?
    558 Old Windsor Rd in Dalton, MA last sold for $648,500 in November 2023.
  • Is Dalton a buyer's or seller's market?
    Dalton is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Dalton?
    Residents describe Dalton, MA as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Dalton, MA.
  • Does 558 Old Windsor Rd have air conditioning?
    Yes, 558 Old Windsor Rd in Dalton, MA has air conditioning.
  • Does 558 Old Windsor Rd have laundry facilities?
    Yes, 558 Old Windsor Rd in Dalton, MA has in-unit laundry.

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