22

Lenox, MA Houses for Sale

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  • /42

    $3,750,000

    • 34 Beds
    • 31 Baths
    • 40,241 Sq Ft

    349 Old Stockbridge Rd, Lenox, MA 01240

    Rare 16.76± acre contiguous institutional campus and redevelopment opportunity in Lenox, MA, in the heart of the Berkshires. Anchored by Overlee, a historic 1903 estate, the property includes multiple buildings with 32 dormitory-style bedrooms, classroom and administrative space, dining facilities, shared common areas, and a large gymnasium. Existing infrastructure includes internal roadways,

    Agent Photo

    Selina Lamb

    Birch Properties

    (413) 343-7496

    349 Old Stockbridge Rd, Lenox, MA 01240
  • /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
  • /33

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft

    870 East St, Lenox, MA 01240

    Beautifully Remodeled Mid Century Ranch in Lenox! Outstanding finished Lower Level. This Home Features 3 Bedrooms and 2 Full baths. A cleared backyard. Patio outside to enjoy your summer afternoons. Deck off of the dining area to relish your morning coffee. Updated kitchen, Natural gas to the house. Newer combi boiler. Updated insulation through entire home. Newer windows. Newer appliances. Newer

    Agent Photo

    Cristian Sanchez

    COHEN & WHITE ASSOCIATES

    (413) 591-7091

    870 East St, Lenox, MA 01240
  • /56

    $1,350,000

    $235K PRICE DROP
    • 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
  • /51

    $2,698,000

    • 5 Beds
    • 5 Baths
    • 4,581 Sq Ft

    109 Under Mountain Rd, Lenox, MA 01240

    A rare and captivating Berkshire offering, this architect-designed home is filled with spectacular natural light, where expansive windows frame protected views of rolling meadows and hills, seamlessly bringing the outdoors in. Located across from conservation land and less than half a mile from Tanglewood, this pristine property offers the perfect balance of sophisticated country living and

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    109 Under Mountain Rd, Lenox, MA 01240
  • /95

    $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
  • /45

    $550,000

    • 3 Beds
    • 2 Baths
    • 2,058 Sq Ft

    200 Hubbard St, Lenox, MA 01240

    Tucked away on 4 acres of wooded and partially cleared land, this lovingly maintained 1960 cape-style home offers the perfect blend of privacy, character, and opportunity. Set back from the road by a long driveway, the property creates a peaceful retreat just minutes from the heart of Lenox and outdoor destinations like October Mountain State Forest & Kennedy Park. Inside, the home is ready for

    Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

    200 Hubbard St, Lenox, MA 01240
  • /29

    $675,000

    • 3 Beds
    • 1.5 Baths
    • 1,562 Sq Ft

    18 Willow Ln, Lenox, MA 01240

    Nestled on a peaceful street, this inviting 3 bedroom, 1.5 bath home offers the perfect blend of comfort and convenience. Step inside to find a bright and welcoming living space filled with natural light, a cozy dining area, and a functional kitchen ready for your personal touch. The three bedrooms provide plenty of room for family, guests, or a home office, while the updated half bath adds extra

    Timothy Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    18 Willow Ln, 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

    $30K PRICE DROP
    • 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
  • /41

    $4,850,000

    • 13 Beds
    • 13.5 Baths
    • 9,510 Sq Ft

    2 Kemble St, Lenox, MA 01240

    The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental.The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a

    Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

    2 Kemble St, Lenox, MA 01240
  • /28

    $279,000

    $20K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,140 Sq Ft

    74 Holmes Rd, Lenox, MA 01240

    Charming Cape in Lenox! Spacious eat in kitchen with access to a screened porch and large deck overlooking the private backyard, living room with wood flooring, quaint dining area, mudroom that connects to the garage, first floor bedroom and full bath. Second level has two bedrooms and finished family room in lower level walkout. Property has had several improvements made within the last 15 years

    Cortney Dupont COHEN & WHITE ASSOCIATES

    74 Holmes Rd, Lenox, MA 01240
  • /33

    $799,000

    • 4 Beds
    • 3 Baths
    • 2,123 Sq Ft

    70 Galway Ct, Lenox, MA 01240

    Beautifully maintained and updated, this charming Cape offers 2 first floor bedrooms and baths, 2 second floor bedrooms with full bath in between, updated cherry kitchen wtih granite counters, formal dining and living and a family room with fireplace, vaulted ceilings and sliders to the large deck. Enjoy this wonderful ''walking neighborhood'', closet to Miraval Resort for pool, golf & fitness

    Mary Jo Piretti PIRETTI REAL ESTATE

    70 Galway Ct, Lenox, MA 01240
  • /33

    $350,000

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft

    16 E New Lenox Rd, Lenox, MA 01240

    OFFER DEADLINE 5PM MONDAY MAY 4THWelcome to this classic 1950s ranch on East New Lenox Road, offering bright, simple living in the Berkshires. This three-bedroom, one-bath home features wood floors, fresh paint, and a clean, functional layout.A three-season porch connects to the attached two-car garage and overlooks a fenced backyard—ideal for relaxing or entertaining. While there is no basement,

    Bresdin Mihlek Coldwell Banker Realty - Western MA

    16 E New Lenox Rd, Lenox, MA 01240
  • /23

    $399,000

    • 3 Beds
    • 1 Bath
    • 1,616 Sq Ft

    792 East St, Lenox, MA 01240

    Nestled into the hillside on East St., this one owner home is awaiting your touches! Set on 1.4 private acres, there is plenty of space to expand this 3 BR embankment ranch. Two fireplaces, one in the first floor LR, the 2nd in the walk out lower level FR, there are also 2 decks, a screened porch and a 3 season room off the family room. All electric and a new septic system to be installed post

    Mary Jo Piretti PIRETTI REAL ESTATE

    792 East St, Lenox, MA 01240
  • /45

    $847,000

    • 3 Beds
    • 2.5 Baths
    • 2,680 Sq Ft

    63 Sherwood Dr, Lenox, MA 01240

    Don't miss this Lenox beauty! Tucked away on a quiet street and abutting preserved land, this colonial is a must see. Main level features hardwood flooring, living room with crown molding, formal dining w. large bay window, open updated kitchen with extensive storage. Family room with gas fireplace opens to spacious screened porch. First floor laundry and half bath. Three bedrooms on the upper

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    63 Sherwood Dr, Lenox, MA 01240
  • /30

    $489,000

    • 2 Beds
    • 2 Baths
    • 1,457 Sq Ft

    181 New Lenox Rd, Lenox, MA 01240

    Enchanting Lenox Cottage minutes to Tanglewood- 2 Bedroom / 2 Full Bath RetreatThe bright, airy living room features warm wood floors that lead into a cozy eat-in kitchen. With a heated sunporch and 1st floor full bath, the home offers multiple inviting spaces to relax or entertain. Step outside to a brand-new back deck, an ideal setting for summer evenings. 2 Bedrooms on second floor, with full

    Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    181 New Lenox Rd, Lenox, MA 01240
  • /13

    $279,900

    $190K PRICE DROP
    • 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. One year American Home Shield Warranty included. PLEASE

    Tyler Scaglione Cameron Real Estate Group

    528 Walker St, Lenox Dale, MA 01242
  • /46

    $749,000

    • 4 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    360 Housatonic St, Lenox, MA 01240

    Lenox MA Colonial on 0.92 acres with 4 bedrooms, 2.5 baths, and 2,184 sq ft of well maintained living space. This move in ready Berkshire home features a spacious eat-in kitchen, formal dining room, bright living room with wood floors, and a screened porch overlooking the yard. Enjoy outdoor living with two decks, a paver patio with BBQ area, and beautiful perennial gardens. Upstairs offers four

    Samantha Homeyer BIRCH PROPERTIES

    360 Housatonic St, Lenox, MA 01240
  • /76

    $825,000

    $25K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,405 Sq Ft

    36 Dunmore Ct, Lenox, MA 01240

    Located in one of Lenox most sought after neighborhoods. Surrounded by woods, it gives you a rural feel, yet you're only minutes to the center of town. This Home features 5 bedrooms 3 Full Bathrooms and a Den with a connecting door to the 1st floor bath which gives you the options of a 6th Bedroom / Suite, Large finished sunroom, Family room with fireplace, a beautiful Kitchen, Combined Formal

    Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

    36 Dunmore Ct, Lenox, MA 01240
  • /20

    $3,599,000

    $396K PRICE DROP
    • 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
$594,000
Median Single Family Sale Price
$675,000
Median Townhouse Sale Price
$374,000
Median 2 Bedroom Sale Price
$370,000
Median 1 Bedroom Sale Price
$250,000
Average Price Per Sq Ft
$368
Number of Homes for Sale
24
Last 12 months Home Sales
73
Months of Supply
3.90
Median List Price
$635,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-2%
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