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Lenox, MA Houses for Sale

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  • /42

    $2,649,000

    • 6 Beds
    • 6.5 Baths
    • 6,225 Sq Ft

    250 West St, Lenox, MA 01240

    Seconds—not minutes—from Tanglewood’s main gate, this reimagined contemporary estate in Lenox is tucked into a sunlit woodland setting offering rare privacy and unrivaled proximity. Originally built in 2017 and completely updated in 2020, the home features soaring ceilings, rich mahogany and cherry finishes, a chef’s kitchen, and multiple entertaining spaces. The ground-floor primary suite is

    Agent Photo

    Selina Lamb

    Birch Properties

    (413) 423-1264

    250 West St, Lenox, MA 01240
  • /56

    $1,490,000

    • 4 Beds
    • 4.5 Baths
    • 3,991 Sq Ft

    9 October Hill Dr, Lenox, MA 01240

    Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a

    Paula McLean PAULA MCLEAN REALTORS INC.

    9 October Hill Dr, Lenox, MA 01240
  • /50

    $7,975,000

    • 8 Beds
    • 6.5 Baths
    • 9,364 Sq Ft

    399 Under Mountain Rd, Lenox, MA 01240

    Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket

    Molly Thomas COMPASS MASSACHUSETTS , LLC GB

    399 Under Mountain Rd, Lenox, MA 01240
  • /53

    $449,000

    • 3 Beds
    • 2 Baths
    • 1,720 Sq Ft

    500 Walker St, Lenox, MA 01242

    Charming 3 bedroom, 2 bath spacious New England Farmhouse with wide board pine floors, updated kitchen & baths, natural gas heat & hot water, vinyl replacement windows, home office/den and first floor laundry room/mudroom. New beautiful 20x18 bluestone patio & retaining wall installed in 2022.

    Matt Carlino MACCARO REAL ESTATE

    500 Walker St, Lenox, MA 01242
  • /35

    $535,000

    • 3 Beds
    • 2 Baths
    • 1,753 Sq Ft

    31 Saint Ann's Ave, Lenox, MA 01240

    This charming bungalow offers the Lenox lifestyle you've been dreaming of. Tucked on a quiet dead-end street just steps from downtown, you can grab morning coffee, enjoy dinner at local favorites, or spend an evening at Tanglewood before strolling home under the stars.Inside, about 1,700 square feet of warm, inviting space blends character and comfort, creating a perfect retreat for every season.

    Amy Shufelt BERKSHIRE LISTINGS

    31 Saint Ann's Ave, Lenox, MA 01240
  • /23

    $215,000

    • 3 Beds
    • 1 Bath
    • 2,552 Sq Ft

    1 Pittsfield Rd, Lenox, MA 01240

    Don't miss this rare chance to acquire and revitalize a property brimming with original character. Located on a well-traveled road with excellent visibility, this 1.25-acre lot offers endless possibilities for personal or business use. Featuring a brand new roof, the property is ideal for a variety of purposes, including retail, restaurant, residential, professional offices, or even a bed and

    Laiken Rapisarda Lamacchia Realty, Inc.

    1 Pittsfield Rd, Lenox, MA 01240
  • /23

    $215,000 New Construction

    • 3 Beds
    • 1 Bath
    • 2,552 Sq Ft

    1 Pittsfield Rd, Lenox, MA 01240

    Don't miss this rare chance to acquire and revitalize a property brimming with original character. Located on a well-traveled road with excellent visibility, this 1.25-acre lot offers endless possibilities for commercial use.Featuring a brand new roof, the property is ideal for a variety of purposes, including retail, restaurant, professional offices, etc. Inside, you'll find an abundance of

    Laiken Rapisarda LAMACCHIA REALTY, INC

    1 Pittsfield Rd, Lenox, MA 01240
  • /60

    $4,950,000

    • 7 Beds
    • 8.5 Baths
    • 7,073 Sq Ft

    1 Pinecroft Dr, Lenox, MA 01240

    Gated Berkshire Stone Estate in exclusive Pinecroft compound with Canyon Ranch Living and its 125 maintenance-free acres. Optional membership. Turnkey home features elevator, 300-year-old reclaimed timber floors and large gourmet kitchen. Great room boasts floor-to-ceiling stone fireplace, wet bar, Nano doors to screened lanai. Two primary en suite bedrooms with cedar closets. Lower level: gym,

    Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    1 Pinecroft Dr, Lenox, MA 01240
  • /13

    $299,900

    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft

    528 Walker St, Lenox Dale, MA 01242

    Large well maintained Colonial on a half acre lot. Large open kitchen with lots of cabinet space. Sliders off kitchen leading to back deck. Bright and sunny living space with a bonus den or office. 3 full sized bedrooms. 2 full baths. Laundry hookups on 2nd floor for convenience. Seller willing to buy down the mortgage rate on this home. PLEASE BOOK SHOWINGS THROUGH SHOWINGTIME.

    Tyler Scaglione Cameron Real Estate Group

    528 Walker St, Lenox Dale, MA 01242
  • /89

    $1,590,000

    • 4 Beds
    • 3.5 Baths
    • 3,805 Sq Ft

    130 E Dugway Rd, Lenox, MA 01240

    Two beautifully landscaped acres with perennial gardens blooming throughout the season. An exceptional 10-room home offers privacy, views, and effortless Berkshire living just minutes from downtown Lenox and Tanglewood. The home features an open and inviting layout with a fireplaced living room and a chef's kitchen designed for gathering and entertaining. A stunning four-season sunroom

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    130 E Dugway Rd, Lenox, MA 01240
  • /23

    $3,400,000

    • 14 Beds
    • 16.5 Baths
    • 11,945 Sq Ft

    615 Laurel St, Lee, MA 01238

    An exceptional opportunity awaits at 615 Laurel Street, Lee, MA, presenting a property of enduring character with 530 feet of lakefront. The expansive interior environment encompasses fourteen dedicated bedrooms, each offering an individual sanctuary for rest and rejuvenation. Complementing these private quarters are sixteen full bathrooms, providing unparalleled comfort and convenience

    Mitchell B Muroff Mitchell B. Muroff

    615 Laurel St, Lee, MA 01238
  • /20

    $3,599,000

    • 15 Beds
    • 15 Baths
    • 11,945 Sq Ft

    615 Laurel St, Lee, MA 01238

    The Lakehouse enjoys a spectacular setting on a westerly facing cliff overlooking pristine Laurel Lake in the heart of The Berkshires. The Lakehouse is a classic three-story, shingle style mansion with 530' of lake frontage including its own dock. Built in 1903, the architecture denotes the unpretentious, timeless elegance of a turn-of-the-century lakeside cottage. There are 15 bedrooms and

    Pamela J Long EAST COAST INN BROKERS

    615 Laurel St, Lee, MA 01238

Why Live in Lenox

Lenox, Massachusetts, is a distinguished retreat in the central Berkshires, known for its vibrant arts scene and upscale atmosphere. This small town, with a population of around 5,000, is a summer haven for the Boston Symphony Orchestra, drawing over 350,000 visitors annually to Tanglewood for concerts featuring artists like James Taylor and John Legend. The town's rich cultural offerings extend to the historic estate of author Edith Wharton, now a museum and a significant attraction. Lenox's housing market is competitive, with a mix of preserved 19th-century mansions, custom contemporary homes, and architectural styles such as Cape Cod and Colonial Revival. The median home price is notably high for the region, reflecting its desirability. Outdoor enthusiasts can explore Kennedy Park's extensive trails or the Massachusetts Audubon Society's Pleasant Valley Wildlife Sanctuary, offering year-round activities from snowshoeing to hiking. Lenox Public Schools are highly rated, providing a robust curriculum with advanced placement options. The walkable downtown area is free of big box stores, featuring local shops, art galleries, and diverse dining options like Alta Restaurant & Wine Bar. Lenox's location along Route 7 provides easy access to nearby towns like Pittsfield, though summer traffic can be heavy. The town's unique blend of cultural richness, natural beauty, and educational excellence makes it a sought-after destination for both residents and visitors.

Home Trends in Lenox, MA

Housing Trends

Median Sale Price
$610,000
Median Single Family Sale Price
$651,250
Median Townhouse Sale Price
$350,000
Median 2 Bedroom Sale Price
$358,000
Median 1 Bedroom Sale Price
$273,687
Average Price Per Sq Ft
$398
Number of Homes for Sale
15
Last 12 months Home Sales
75
Months of Supply
2.40
Median List Price
$642,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
1%
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