249 Main St, Lenox, MA 01240
Property image
Property image
OFF MARKET

249 Main St
Lenox, MA 01240

  • 3 Beds
  • 3 Baths
  • 1,500 sqft (on 0.78 acres)

$591,300

Trulia Estimate
as of Aug 2, 2026
Est. Refi. Payment $3,700/mo*

$591,300

Trulia Estimate
as of Aug 2, 2026
Est. Refi. Payment $3,700/mo*
3 Beds
3 Baths
1,500 sqft
(on 0.78 acres)

Local Information

  • Map ViewExplore the area around 249 Main St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1962
Lot Size
0.78 acres
Living Area
1,500 sqft
Price/Sqft
$394
Parking
Garage

About this House

Duplex located in Lenox only one mile to town
Close to Route 7
Kennedy Park access in backyard
Ample parking
Two one bedroom apartments
One upstairs suitable for single $1500 includes heat, electricity and garbage
Larger downstairs apartment $1800 includes heat, electricity and garbage
Or whole house rental $3000
Can be furnished if need be

Seasonal rental
Now thru May 15
249 Main St, Lenox, MA 01240 is a 3 bedroom, 3 bathroom, 1,500 sqft single-family home built in 1962. It last sold for $150,342 on Jan 4, 2002. More recently, it was listed as a rental in October 2022 with an asking price of $1,500 per month. That rental listing was removed on November 10, 2022. It is currently off market. The Trulia Estimate is $591,300, with a rent estimate of $4,530/month.

Home Details for 249 Main St

Interior Features

Interior Details
BasementNumber of Rooms: 9
Heating & Cooling
Heating: Other, OilHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DryerWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodPatio
Parking & Garage
GarageParking: Garage Detached, Off Street

Property Information

Year Built
Year Built: 1962Year Updated: 1980
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.78 acres

Additional Information

On Site Laundry Available

Price History for 249 Main St

DatePriceEventSource
11/10/2022ListingRemovedZillow Rental Manager
10/25/2022$1,500Listed For RentZillow Rental Manager
06/21/2022ListingRemovedZillow Rental Manager
06/09/2022$4,000PriceChange
Zillow Rental Manager
06/02/2022$5,000PriceChange
Zillow Rental Manager
05/25/2022$6,000Listed For RentZillow Rental Manager
04/01/2021ListingRemovedZillow Rental Manager
03/30/2021$1,500Listed For RentZillow Rental Manager
12/06/2015$299,900ListingRemovedAgent Provided
07/15/2015$299,900PriceChange
Agent Provided
06/06/2015$319,900Listed For SaleAgent Provided
01/04/2002$150,342Sold
N/A

Market trends in Lenox

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
36
1
MoM
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Property Tax and Assessment

Year2025
Tax$4,360
Assessment$481,800
Home facts updated by county records

Comparable Sales for 249 Main St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.66
Single-Family Home
$625,000
08/12/25
3
2
1,687
0.39
Single-Family Home
$1,550,000
08/06/25
4
2.5
4,049
0.62
Single-Family Home
$638,000
04/15/26
4
2.5
1,856
0.73
Single-Family Home
$675,000
10/15/25
3
2
1,444
0.61
Single-Family Home
$495,000
06/15/26
3
2
1,753
1.04
Single-Family Home
$392,000
02/27/26
3
2.5
1,765
0.85
Single-Family Home
$399,000
11/25/25
3
1
1,344
1.01
Single-Family Home
$856,000
10/01/25
3
2
1,630
1.19
Single-Family Home
$425,000
09/22/25
3
2
1,375
0.77
Single-Family Home
$660,000
08/22/25
4
2
2,242

Nearby homes

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Assigned Schools

These are the assigned schools for 249 Main St.
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 Lenox

At least 23 Trulia users voted on each feature.
  • 96 % Say car is needed

  • 91 % Say yards are well-kept

  • 83 % Say it's dog friendly

  • 80 % Say parking is easy

  • 78 % Say people would walk alone at night

  • 72 % Say kids play outside

  • 69 % Say there's wildlife

  • 68 % Say it's walkable to grocery stores

  • 68 % Say there's holiday spirit

  • 61 % Say it's walkable to restaurants

  • 60 % Say it's quiet

  • 60 % Say streets are well-lit

  • 56 % Say there are sidewalks

  • 56 % Say there are community events

  • 52 % Say they plan to stay for at least 5 years

  • 51 % Say neighbors are friendly

Sourced by Trulia users. Learn more about our methodology.
  • Maurice Matteodo
    "Safe and walkable. Excellent schools. Beat downtown. Tanglewood down the road. Lots of parks and woods nearby."
  • Johnmac
    "We look out for each other and look out for one another. Lived here my entire life! Lots of art, dance, etc. "
  • Stephen Alsdorf
    "Car-dependent, but easy. There’s almost never any traffic (and even what we think of as “traffic” doesn’t really qualify). I drive through what is literally Norman Rockwell America to get to work, passed a farm, and through the center of Stockbridge, Rockwell’s home. Basically the entire thing is on a two-lane country road."
  • Marlene M.
    "Expensive to live. Some Lenox public service people are out of touch. (Selectman and boards) People who visit in the summer are mean and dislike the locals which is very sad! locals are fun loving! Great Schools and teachers and plenty of artsy things to do! "
  • Ksprague
    "The Berkshires is a great place to live, raise a family or retire. I've lived here most of my life and you can't beat the clean air, friendly people, great schools and the outdoors. I'm a skiier, hiker, and bicycle rider and there is no where else so accommodating to all these pursuits. We brought up our kids here and they are happy, healthy, well-adjusted and turning into great young adults. It's a great place to live."

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Homes for sale near 249 Main St

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Off Market Homes Near 249 Main St

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