Lenox Dale, MA Homes

/40
$1,795,000
- 4 Beds
- 3 Baths
- 5,469 Sq Ft
17 East St, Lenox, MA 01240

Nestled just north of Stockbridge, MA, this elegantly expanded brick Federal estate offers a harmonious blend of historic charm and modern design on 13+/- acres (9 conserved.) Originally built in the 1830s, the Carter Estate has been artfully expanded and renovated and boasts over 5,400sf of light-filled, luxurious living space, ideal for those seeking a private yet gracious lifestyle.As you

Selina Lamb

BIRCH PROPERTIES

(413) 300-6860

17 East St, Lenox, MA 01240
/17
$12,500 per month
- 3 Beds
- 2 Baths
- 1,861 Sq Ft
- House for Rent
5 Beachwood Dr, Stockbridge, MA 01262

Delightful, classic Berkshires summer cottage in the Beachwood enclave. Shares in gorgeous community beach at south end of the Stockbridge Bowl (Lake Mahkeenac.) Enjoy swimming, kayaking, etc. Minutes to Tanglewood and all the cultural delights of the Berkshires. 3BR including primary suite with bath. 1 Queen BR, 1 Br with double bunk beds. Fantastic large screened porch with dining. LR with

Selina Lamb

Birch Properties

(413) 610-3637

5 Beachwood Dr, Stockbridge, MA 01262
/52
$975,000 Sold Jul 25, 2025
- 2,010 Sq Ft
- $485/SF
- 10 Days On Market
- 4 Beds
- 3 Baths
- Built 1948
66 Interlaken Rd, Stockbridge, MA 01262

Handsome redesign and total renovation in 2017. Living space all on one convenient level. Light bright interior. Well-designed kitchen opens to the great room with cathedral ceiling, fireplace and access to the three-season porch. Primary suite privately set at one end of the house and additional 3 bedrooms and 2 baths (1 ensuite) at the other end of the house. Den. Beautiful wood floors.

Sheila Thunfors STONE HOUSE PROPERTIES, LLC

66 Interlaken Rd, Stockbridge, MA 01262

/36
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,269 Sq Ft
4 Lee Rd, Lee, MA 01238

4 Lee Rd, Lee, MA 01238

/6
$425,000
- Land
- 3.30 Acres
- $128,788 per Acre
9 Wheatleigh Dr, Stockbridge, MA 01262

RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

Selina Lamb

Birch Properties

(413) 343-5283

9 Wheatleigh Dr, Stockbridge, MA 01262
/4

$1,305 - $3,447 per month

Forge

1-3 Beds

66 Brushwood Way, Lenox, MA 01240

Forge is a brand new mixed-income housing community currently under construction in Lenox, MA. The development will include 65 apartments within 13 townhome-style buildings, and a community clubhouse. Each building at Forge will contain 5-6 apartments, with a mix of one-, two-, and three-bedroom apartments available at various income tiers (30, 60, 120% AMI). Apartments will have their own

66 Brushwood Way, Lenox, MA 01240
/27
$265,000 Sold Jul 23, 2025
- 800 Sq Ft
- $331/SF
- 89 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1860
34 Church St Unit 2, Lenox, MA 01240

Discover the perfect opportunity in the heart of downtown Lenox with a Church Street view! This charming condo is an ideal choice for investors, second homeowners, or those seeking a convenient lifestyle. This unit boasts two bedrooms, two full baths, beautiful wood floors, and a cozy gas fireplace. You will immediately have access to various shops, restaurants, and Tanglewood just minutes away!

Jessica Rizzo Lamacchia Realty, Inc.

34 Church St Unit 2, Lenox, MA 01240

/36
Est $2,050,987 Not Listed For Sale
Unlisted Address

Unlisted Address

/6
$425,000
- Land
- 3.30 Acres
- $128,788 per Acre
9 Wheatleigh Dr, Stockbridge, MA 01262

RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

Selina Lamb

BIRCH PROPERTIES

(413) 722-5098

9 Wheatleigh Dr, Stockbridge, MA 01262
/11
$2,600 per month
- 3 Beds
- 1.5 Baths
- 1,165 Sq Ft
- Apartment for Rent
125 Center St Unit 2, Lee, MA 01238

Available Immediately! Second floor apartment. Three bedroom with a full bathroom and a half bathroom. In unit washer and dryer. The house is equipped with generator so you never have to worry about power outages again. Pets negotiable. First, last and security due at signing. Employment verification, background check, credit check and references required.

Timothy Dunn Venture

125 Center St Unit 2, Lee, MA 01238
/25
$610,000 Sold Jul 22, 2025
- 1,720 Sq Ft
- $355/SF
- 11 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2011
2 Evergreen Trail, Lenox, MA 01240

Enjoy the peaceful life at Lenox Woods...look out your back windows or screened porch at conservation land and the occasional deer. And inside, you'll enjoy the open living with great room and gas fireplace, kitchen with granite, first floor Primary Suite with vaulted ceiling, plus the finished 2nd floor with family room, 2 large bedrooms with full bath in between and a sweet, newly finished 4th

Mary Jo Piretti PIRETTI REAL ESTATE

2 Evergreen Trail, Lenox, MA 01240

/5
Est $29,006 Not Listed For Sale
Unlisted Address

Unlisted Address

/9
$149,000 Pending
- 5 Beds
- 3 Baths
- 2,316 Sq Ft
705 Cape St Unit 2, Lee, MA 01238

Fixer Upper Opportunity/Two Family Home on .69 acres. Town Sewer/Separate utilities.Spring Fed. Separate driveways.PROPERTY BEING SOLD ''AS -IS''.SALE IS CONTINGENT UPON APPROVAL FROM COMMONWEALTH OF MASSACHUSETTS MASSHEALTH RECOVERY.

Lisa Kelley

MACCARO REAL ESTATE

(413) 296-2834

705 Cape St Unit 2, Lee, MA 01238
/20

$1,082 per month

Lenox Schoolhouse Apartments

Studio

109 Housatonic St, Lenox, MA 01240

The Berkshires' newest community is NOW OPEN!!! Newly renovated studios and one bedrooms with ALL UTILITIES INCLUDED* - Spacious open layouts, brand new interiors, plush carpet, sunlit windows, abundant closet space. Lenox Schoolhouse Apartments is within walking distance to the center of town. Enjoy the local shops, art galleries, restaurants and entertainment. You'll be sure to experience

109 Housatonic St, Lenox, MA 01240
/14
$396,200 Sold Jul 21, 2025
- 938 Sq Ft
- $422/SF
- 5 Days On Market
- 2 Beds
- 1 Bath
- Built 1968
5 Morgan Manor Unit 9, Lenox, MA 01240

This unit is the ''trifecta'' of Morgan Manor: first floor, 2 BR and with garage! Plus it's been fully renovated and has a gorgeous eat in cherry/granite/stainless kitchen, updated bath and beautiful hardwood floors throughout. Maintenance fees of $716/month include your heat, hot water, basic cable/internet and all exterior maintenance....furnishings available if you want to just bring your

Mary Jo Piretti PIRETTI REAL ESTATE

5 Morgan Manor Unit 9, Lenox, MA 01240

/26
Est $481,591 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,538 Sq Ft
26 Old Stockbridge Rd Unit 4, Lenox, MA 01240

26 Old Stockbridge Rd Unit 4, Lenox, MA 01240

/57
$499,000 Under Contract
- 3 Beds
- 2.5 Baths
- 2,202 Sq Ft
970 Cape St, Lee, MA 01238

Welcome to your perfect escape in the Berkshries! This open and inviting raised ranch on 1.75 beautiful acres, just minutes from Goose Pond, Jacob's Pillow, Mass Pike, the Appalachian Trail, and many other nearby cultural and outdoor attractions.Built in 2007, the home features radiant heat throughout, with bamboo floors upstairs and decorative Crete floors on the finished lower level. The heart

Lisa Kelley

MACCARO REAL ESTATE

(413) 779-3166

970 Cape St, Lee, MA 01238
/13
$2,500 per month
- 2 Beds
- 1.5 Baths
- 1,156 Sq Ft
- Apartment for Rent
125 Center St Unit 1, Lee, MA 01238

Available Immediately! First-floor 2-bedroom, 2-bath apartment located a short distance from downtown Lee. Features include hardwood floors, a gas fireplace, front porch, dishwasher, and in-unit washer/dryer. Equipped with a generator for added peace of mind. Tenant pays all utilities. Pets considered. Move-in costs include first and last month’s rent and security deposit. All applicants subject

Timothy Dunn Venture

125 Center St Unit 1, Lee, MA 01238
/37
$350,000 Sold Jul 18, 2025
- 1,919 Sq Ft
- $182/SF
- 37 Days On Market
- 4 Beds
- 2 Baths
- Built 1979
881 Holmes Rd, Pittsfield, MA 01201

Enjoy beautiful mountain views from this spacious 4-bedroom, 2-bath Pittsfield split-level on Holmes Road. Featuring a bright open layout, large picture windows, and fresh interior updates, this home offers a flexible floor plan with generous living space. The lower level includes space ideal for a home office or family room. Enjoy outdoor living on the rear deck and a large private yard. With a

Ed Rich BISHOP WEST REAL ESTATE

881 Holmes Rd, Pittsfield, MA 01201

/22
Est $356,785 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,257 Sq Ft
410 Greylock St, Lee, MA 01238

410 Greylock St, Lee, MA 01238

/30
$2,450,000
- 2 Beds
- 2.5 Baths
- 1,950 Sq Ft
165 Kemble St Unit 17, Lenox, MA 01240

Nestled within the serene, world-renowned Canyon Ranch Lenox campus, this bespoke two-bedroom, two-and-a-half-bath home is among the most private and luxuriously appointed in the Berkshires. A rare opportunity to own a residence where every detail--from architecture to finishes--echoes sophisticated European elegance while embracing the wellness-centered ethos of Canyon Ranch living.Inside,

Selina Lamb

BIRCH PROPERTIES

(413) 547-4966

165 Kemble St Unit 17, Lenox, MA 01240
/4
$2,400 per month
- 2 Beds
- 1 Bath
- 130 Sq Ft
- House for Rent
177 Laurel St, Lee, MA 01238

Located in Lee, is this 2BR, 1 Bath, duplex home, with updated bathroom tile floor, hardwood and laminated flooring throughout, freshly painted. No smoking 1st and last references and credit check

177 Laurel St, Lee, MA 01238
/37
$400,000 Sold Jul 16, 2025
- 1,152 Sq Ft
- $347/SF
- 431 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
15 Elk Dr, Lee, MA 01238

Welcome to Leisure Lee -- where natural beauty meets modern comfort in the heart of the Berkshires.Nestled in a serene setting just moments from the crystal-clear waters of Goose Pond, this contemporary ranch-style home offers the perfect blend of relaxation, recreation, and year-round living. Leisure Lee is a private community treasured for its peaceful ambiance, exclusive lake access, and

Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

15 Elk Dr, Lee, MA 01238

/25
Est $493,948 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,872 Sq Ft
280 Mandalay Rd, Lee, MA 01238

280 Mandalay Rd, Lee, MA 01238

/53
$2,649,000
- 6 Beds
- 6.5 Baths
- 4,289 Sq Ft
250 West St, Lenox, MA 01240

Just seconds not minutes from the main gates of Tanglewood, this stunning contemporary estate is tucked into a sunlit site surrounded by woodland, offering a rare blend of proximity and seclusion. In a region renowned for its natural beauty, it's almost unheard of to find a home this close to the cultural heart of the Berkshires that also feels so entirely removed.Perfectly positioned for

Selina Lamb

BIRCH PROPERTIES

(413) 423-1264

250 West St, Lenox, MA 01240
/20
$1,800 per month
- 1.5 Baths
- 1,920 Sq Ft
- Property for Rent
236 Main St, Lee, MA 01238

Prime location located on Main St. in Downtown Lee within a short walking distance to new EAGLE MILL development project with a total of 135 new housing units. This turnkey unit has been designed and used as a restaurant, deli and sandwich shop and has seating for 12 with parking in front and behind the building. Highly visible centrally located to serve the business and residential community.

Tim Gallagher STONE HOUSE PROPERTIES, LLC

236 Main St, Lee, MA 01238
/49
$487,500 Sold Jul 15, 2025
- 3,210 Sq Ft
- $152/SF
- 17 Days On Market
- 6 Beds
- 2.5 Baths
- Built 1901
9 High St, Lenox, MA 01240

Nestled in one of the most desirable towns in the Berkshires, this charming multi-family home presents a rare and exciting opportunity for investors, contractors, or visionary homeowners. Set on a spacious and desirable lot, this as-is property is ready to be reimagined--offering the perfect canvas for renovation, expansion, or transformation. The home features two side-by-side living units, each

Diane Thorson WILLIAM PITT SOTHEBY'S - GT BARRINGTON

9 High St, Lenox, MA 01240

/34
Est $567,304 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 2,761 Sq Ft
15 Greylock St, Lee, MA 01238

15 Greylock St, Lee, MA 01238

/59
$895,000
- 4 Beds
- 3 Baths
- 2,732 Sq Ft
135 East St, Lee, MA 01238

Rustic Style Expansive Cape. Embrace the eastern views and warmth of New England's Mountains from the beautiful open front porch! Amazing custom home built by a true craftsman. Beautiful natural wood elements & exposed beams throughout, make for a wonderful Berkshire retreat! Large custom kitchen with granite & butcher block countertops, open dining room for easy entertaining with double French

Lisa Kelley

MACCARO REAL ESTATE

(413) 308-6698

135 East St, Lee, MA 01238
/16
$3,600 per month
- 2 Beds
- 1 Bath
- 1,300 Sq Ft
- House for Rent
165 Stockbridge Rd, Lee, MA 01238

Modern 2bdrm guesthouse w/ private porch with sweeping views on historic property. Price does not include utilities, but we can offer an all-inclusive monthly rate. Primary bedroom and the living room have skylights (sun-filled daytime). Primary bdrm has door to porch. Bathroom has Rain-shower and tub. Top of line W/D. Kitchen used and loved by chefs. Farmhouse dining table + kitchen

165 Stockbridge Rd, Lee, MA 01238
/23
$355,000 Sold Jul 15, 2025
- 1,552 Sq Ft
- $229/SF
- 3 Days On Market
- 2 Beds
- 3 Baths
- Built 1976
9 Rolling Hills Unit 5, Lenox, MA 01240

This immaculate 2Bd, 3 Ba Move In condition unit is being offered Turn Key - fully furnished and fully stocked! But what really makes this unit special are the gorgeous Berkshire views from your private deck!The unit is completely updated & painted. Just bring your clothes and enjoy the pool, tennis & pickle ball courts, kayak racks, community victory garden, book club, mah jong, Bridge.

Susan Baum BERKSHIRE HOMES AND CONDOS

9 Rolling Hills Unit 5, Lenox, MA 01240

/38
Est $413,270 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,569 Sq Ft
180 Forest St, Lee, MA 01238

180 Forest St, Lee, MA 01238

/36
$299,000
- 3 Beds
- 2 Baths
- 1,494 Sq Ft
20 Summer St, Lee, MA 01238

Antique Greek Revival style home overlooking downtown Lee! Beautiful view with splendid sunrises over October Mountain. Wise investment, located within the up-and-coming downtown redevelopment district in historic Lee, Ma. ''Gateway to the Berkshires'', voted one of the top ten small towns, known for the scenery, the arts and activities. This lovely home offers wood flooring throughout, light &

Lisa Kelley

MACCARO REAL ESTATE

(413) 779-8698

20 Summer St, Lee, MA 01238
/5
$12 per month
- 0.5 Baths
- 2,106 Sq Ft
- Property for Rent
10 Valley St, Lee, MA 01238

2106 SF OFFICE SPACE. Building B available for immediate occupancy. New bathroom. Ample power. LED lighting. Central Air. In addition to base rent of $12.00/sf/yr tenant pays for heat, electricity, security, trash removal, telecommunications renter's/liability insurance and taxes. Tenant, at tenants expense, may make alterations. Landlord pays for insurance, water & sewer, snow removal and

Rich Aldrich WILLIAM PITT SOTHEBY'S - LENOX

10 Valley St, Lee, MA 01238
/11
$1,370,000 Sold Jul 15, 2025
- 1,109 Sq Ft
- $1235/SF
- 34 Days On Market
- 1 Bed
- 1.5 Baths
- Built 2017
165 Kemble St Unit 2, Lenox, MA 01240

Discover luxury living at Canyon Ranch with this 1-bedroom condo, boasting a chef's kitchen with marble countertops, and an expansive great room with a marble gas fireplace. Savor your morning coffee on the serene private balcony. The primary suite is a retreat with a spa-like marble bathroom, ample walk-in closet, and a cozy fireplace. Exclusive resort membership provides access to unparalleled

Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

165 Kemble St Unit 2, Lenox, MA 01240

/34
Est $279,716 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,360 Sq Ft
208 High St, Lee, MA 01238

208 High St, Lee, MA 01238

/5
$998,000
- Land
- 9 Acres
- $109,670 per Acre
19 and 21 Wheatleigh Dr, Stockbridge, MA 01240

RARE LUXURY: READY-to-BUILD MODERNIST RETREAT on EXCLUSIVE PRIVATE POND minutes to TANGLEWOODWelcome to a once-in-a-lifetime opportunity in the heart of the Berkshires. Set on 9.1 acres approximately acres of pristine land, this exceptional estate parcel offers frontage on tranquil Lily Pond, a private, non-motorized body of water that ensures peace, privacy, nature and views. Comprising the

Selina Lamb

BIRCH PROPERTIES

(413) 343-4919

19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
/28
$253,207 Sold Jul 14, 2025
- 1,552 Sq Ft
- $163/SF
- 47 Days On Market
- 3 Beds
- 3 Baths
- Built 1976
8 Rolling Hills Unit 9, Lenox, MA 01240

Welcome to The Rolling Hills Townhouse Community in the glorious town of Lenox, Mass. The facility boasts the finest of amenities including a fully equipped clubhouse, fitness center, pool, tennis, community gardens and walking trails for you and your furry friends. Only minutes from downtown fine restaurants, shopping , Shakespeare&Company and Tanglewood. The school system is one of the most

Buddy Lewis BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

8 Rolling Hills Unit 9, Lenox, MA 01240

/49
Est $487,586 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,352 Sq Ft
85 Highfield Dr, Lee, MA 01238

85 Highfield Dr, Lee, MA 01238

/10
$199,000
- Land
- 1.31 Acres
- $151,907 per Acre
245 Spring St, Lee, MA 01238

One of two beautiful building lots available on Spring Street, Lee. Lee has been voted one of the top 10 northeastern small towns in New England. Idyllic setting on quiet country road yet 2 miles from Stockbridge, 3 miles to Tanglewood, and 5 minutes to Laurel Lake! Build your dream home and enjoy all the Berkshires has to offer! Beautiful place to live, ample outdoor recreation, farm to table

Lisa Kelley

MACCARO REAL ESTATE

(413) 722-5964

245 Spring St, Lee, MA 01238

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