25 Hillside Dr, Lenox, MA 01240
OFF MARKET

25 Hillside Dr
Lenox, MA 01240

  • 3 Beds
  • 4 Baths
  • 1,899 sqft (on 0.38 acres)

$556,000

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $3,370/mo*

$556,000

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $3,370/mo*
3 Beds
4 Baths
1,899 sqft
(on 0.38 acres)

Local Information

  • Map ViewExplore the area around 25 Hillside Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

One owner custom built home with a nice wooded setting,yet just a 5 minute walk to downtown Lenox. Cathedral ceiling in greatroom open to kitchen and sliders to deck. Lower level would make great guest or in-Law quarters. Much to like about this well built downtown Lenox home. Come See! Brokered And Advertised By: MCLEAN REALTORS Listing Agent: John L. McLean
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.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 25 Hillside Dr

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: Other, GasHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1991Year Updated: 1992
Property Type / Style
Property Type: Single Family HomeArchitecture: ranch

Community

Units in Building: 1

Lot Information

Lot Area: 0.38 acres

Price History for 25 Hillside Dr

DatePriceEventSource
04/29/2011$275,300Sold
BCMLS #191806
09/11/2010$279,000Listed For SaleAgent Provided
12/24/1996$180,000Sold
N/A

Market trends in Lenox

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
37
7
MoM
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Property Tax and Assessment

Year2025
Tax$4,000
Assessment$442,000
Home facts updated by county records

Comparable Sales for 25 Hillside Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.06
Single-Family Home
$638,000
04/15/26
4
2.5
1,856
0.09
Single-Family Home
$660,000
08/22/25
4
2
2,242
0.07
Single-Family Home
$495,000
06/15/26
3
2
1,753
0.38
Single-Family Home
$392,000
02/27/26
4
2
1,764
0.32
Single-Family Home
$675,000
10/15/25
3
2
1,444
0.33
Single-Family Home
$475,000
08/12/25
3
1
1,380
0.28
Single-Family Home
$1,550,000
08/06/25
4
2.5
4,049
0.73
Single-Family Home
$856,000
10/01/25
3
2
1,630
0.93
Single-Family Home
$425,000
09/22/25
3
2
1,375
0.92
Single-Family Home
$587,500
11/05/25
3
2.5
1,680

Nearby homes

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Assigned Schools

These are the assigned schools for 25 Hillside Dr.
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 25 Hillside Dr

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Off Market Homes Near 25 Hillside Dr

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25 Hillside Dr, Lenox, MA 01240 is a 3 bedroom, 4 bathroom, 1,899 sqft single-family home built in 1991. This property is not currently available for sale. 25 Hillside Dr was last sold on Apr 29, 2011 for $275,300. The current Trulia Estimate for 25 Hillside Dr is $556,000.