17

Lenox, MA Homes for Sale with Garage

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  • /84

    $1,650,000

    • 7 Beds
    • 6.5 Baths
    • 5,693 Sq Ft

    20 E Dugway Rd, Lenox, MA 01240

    Just 3 miles from Tanglewood and moments from the heart of Lenox, this 36+ acre estate offers rare scale, privacy, and flexibility in one of the Berkshires' most sought-after settings. A long, tree-lined driveway creates a strong sense of arrival, unfolding into two separate residences surrounded by woods, open land, and long-range possibility. The acreage offers both seclusion and the ability to

    Agent Photo

    Nick Geranios

    WILLIAM PITT SOTHEBY'S - LENOX

    20 E Dugway Rd, Lenox, MA 01240
  • /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

    349 Old Stockbridge Rd, Lenox, MA 01240
  • /54

    $1,190,000

    $485K 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
  • /49

    $1,775,000

    • 6 Beds
    • 5.5 Baths
    • 4,099 Sq Ft

    14 Fairway Dr, Lenox, MA 01240

    Experience refined Berkshire living at Coldbrooke East, where timeless elegance meets exceptional privacy. Perfectly sited at the end of a quiet cul-de-sac and abutting the golf course, this extraordinary six-bedroom, 5.5-bath residence offers luxurious single-level living with a thoughtfully designed 1,000-square-foot addition. Custom designer finishes, exceptional craftsmanship, and substantial

    Paula McLean PAULA MCLEAN REALTORS INC.

    14 Fairway 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
  • /35

    $689,000

    • 3 Beds
    • 2 Baths
    • 1,532 Sq Ft

    19 Kemble St, Lenox, MA 01240

    Unbeatable Lenox location! Near the top of Kemble Street, you'll find this charming 1950's-vintage ranch home that's a super short walk to the village. Timeless details merge with everyday comfort! Hardwood floors flow throughout. Living room features a wood-burning fireplace. Dining opens to expanded galley kitchen on one end and to a den/office flexible space on the other. Three bedrooms, two

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    19 Kemble St, Lenox, MA 01240
  • /78

    $2,100,000

    • 5 Beds
    • 3.5 Baths
    • 3,387 Sq Ft

    19 Cliffwood St, Lenox, MA 01240

    Iconic Lenox home: very rarely does a home with this historic integrity come on the market...now is your time to continue its legacy . Built in 1915 as one of the focal points of Cliffwood Street, this charming home has been updated for today's life style without sacrificing its significant architectural details. Beautiful common rooms including a dream kitchen with marble counters, formal Dining

    Mary Jo Piretti PIRETTI REAL ESTATE

    19 Cliffwood St, Lenox, MA 01240
  • /36

    $4,150,000

    • 3 Beds
    • 3.5 Baths
    • 3,348 Sq Ft

    165 Kemble St Unit 18, Lenox, MA 01240

    Experience elevated wellness living in this exceptional Canyon Ranch penthouse in Lenox. This 3,300+ sq. ft. residence offers three spacious ensuite bedrooms, a powder room, an expansive great room, a chef's kitchen and three fireplaces that create a warm, inviting atmosphere. A private patio provides the perfect retreat to relax and enjoy the natural beauty of the Berkshires. Ownership includes

    Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    165 Kemble St Unit 18, Lenox, MA 01240
  • /27

    $664,500

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,100 Sq Ft

    28 Evergreen Trail Unit 28, Lenox, MA 01240

    Fantastic Offer for a Custom-designed & beautifully maintained one-owner residence offers 4 bedrooms, 3.5 baths, in the most desirable location in the verdant Berkshires. Calm & Quiet with direct access to Kennedy Park - you'll enjoy the perfect balance of nature, community & the Arts. Lenox offers quality shops, farmers markets, Botanic Gardens & music. A beautiful open floor plan features a

    Heather Gallagher STONE HOUSE PROPERTIES, LLC

    28 Evergreen Trail Unit 28, Lenox, MA 01240
  • /56

    $1,149,000

    $130K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,691 Sq Ft

    18 Highcrest Rd, Lenox, MA 01240

    Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots of Privacy being an end unit. Come enjoy Tennis Swimming pool and Fitness center all on property. 3 Full floors of living space with Primary Suite/Walk in Closet on 1st floor. Spacious open floor plan to enjoy entertaining with plenty of outdoor space with screened in porch and private deck. Enjoy Easterly

    Suzann Ward HOUSATONIC REAL ESTATE

    18 Highcrest Rd, Lenox, MA 01240
  • /60

    $2,498,000

    $200K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 4,581 Sq Ft

    109 Under Mountain Rd, Lenox, MA 01240

    Some homes are purchased. Others become part of a family's legacy. Welcome to 109 Under Mountain Road. There is something unmistakably special about a Berkshire summer- evening stroll to Tanglewood, morning coffee overlooking protected meadows, or relaxing on the patio as the music of the Boston Symphony Orchestra drifts softly through the evening air. Bathed in extraordinary natural light, this

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    109 Under Mountain Rd, Lenox, MA 01240
  • /44

    $789,900

    $57K PRICE DROP
    • 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 side street. Main level w hardwood flooring, living room with crown molding, formal dining w. large bay window, updated kitchen w extensive cabinetry. Family room w gas fireplace opens to large screened porch / patio. First floor laundry and 1/2 bath. Three bedrooms on the upper level; primary suite w adjoining dressing room/ primary bath with

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    63 Sherwood Dr, Lenox, MA 01240
  • /47

    $1,399,000

    $51K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,968 Sq Ft

    3 A Coldbrooke Dr, Lenox, MA 01240

    Four-bedroom homes are a rarity at Coldbrooke, where most residences offer three. This one combines that hard-to-find layout and one of the community's more generous floor plans with a location beside the Miraval Berkshires resort and the historic Wyndhurst estate, putting world-class spa, dining, and golf just steps from the door. Inside, vaulted ceilings and an open layout fill the home with

    Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

    3 A Coldbrooke Dr, Lenox, MA 01240
  • /42

    $1,200,000

    • 4 Beds
    • 5.5 Baths
    • 2,540 Sq Ft

    8 Stoneledge Rd, Lenox, MA 01240

    Beautifully maintained home set on a private one-acre lot on a quiet cul-de-sac in one of Lenox's most desirable neighborhoods. This thoughtfully designed residence offers four bedrooms and 5.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The inviting floor plan is ideal for both everyday living and entertaining. Step outside to a beautifully landscaped

    Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    8 Stoneledge Rd, Lenox, MA 01240
  • /37

    $685,000

    • 3 Beds
    • 2.5 Baths
    • 1,620 Sq Ft

    200 Old Stockbridge Rd Unit VA-6, Stockbridge, MA 01262

    STUNNING VIEWS for as far as you can see from this modern unit located in Winden Hills Vanna building. Open common spaces washed in natural light; Great room with scenic views, fireplace and built ins, kitchen with charm and character open to dining. Primary w/en suite full bath, two guest bedrooms and additional one and half baths. This unit comes with access to the elevator for convenience, a

    Cortney Dupont COHEN & WHITE ASSOCIATES

    200 Old Stockbridge Rd Unit VA-6, Stockbridge, MA 01262
  • /61

    $675,000

    • 3 Beds
    • 2.5 Baths
    • 1,765 Sq Ft

    9 Bolton Dr, Lenox, MA 01240

    Located in the Heart of Downtown Lenox on a dead-end street, this move-in ready Colonial is beautifully renovated and features a comfortable open floor plan perfect for the holidays and entertaining. A new Kitchen with a farm sink and 36'' range, hardwood floors, Living Room with fireplace, a half bath on the first floor, 3 bedrooms, 2 full baths and laundry on the second floor and finished

    Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

    9 Bolton Dr, Lenox, MA 01240
  • /50

    $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

Home Price Trends

Median Sale Price
$632,750
Median Single Family Sale Price
$742,000
Median Townhouse Sale Price
$524,500
Median 2 Bedroom Sale Price
$457,000
Median 1 Bedroom Sale Price
$187,000
Average Price Per Sq Ft
$368
Number of Homes for Sale
14
Last 12 months Home Sales
66
Months of Supply
2.50
Median List Price
$717,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
5%
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