Homes for Sale near Berkshire Country Day School

/58
$1,595,000
- 6 Beds
- 3.5 Baths
- 3,905 Sq Ft
21 Stockbridge Rd, West Stockbridge, MA 01266

Tucked away on a private 2.35-acre knoll, this beautifully updated residence offers a rare blend of antique charm and modern ease in one of the Berkshires' most sought-after villages. With six generously sized bedrooms, a chef's kitchen designed for entertaining, and multiple inviting living spaces with fireplaces, the home is ideal for gatherings or quiet retreats alike. A stunning contemporary

Dan Alden

ALDEN COUNTRY REAL ESTATE SERVICES

(413) 675-5317

21 Stockbridge Rd, West Stockbridge, MA 01266
/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
/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
/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
/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
/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) 329-0435

165 Kemble St Unit 17, Lenox, MA 01240
/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
/6
$650,000
- Land
- 19 Acres
- $34,211 per Acre
0 Mohawk Lake Rd, Stockbridge, MA 01262

Discover a rare opportunity to own a piece of history in Stockbridge, available for the first time in over 120 years. This stunning land offers a private setting perfect for building your dream home, while being just moments away from the renowned Norman Rockwell Museum, Chesterwood, the enchanting Berkshire Botanical Gardens, and the charming downtown Stockbridge, all within a 3-mile radius.

Gary Fuls Jr

RE/MAX TRANSITIONS

(413) 884-5511

0 Mohawk Lake Rd, Stockbridge, MA 01262
/82
$2,550,000
- 6 Beds
- 6.5 Baths
- 7,143 Sq Ft
13 Taconic Ave, Lenox, MA 01240

An Unrivaled 8-Acre Sanctuary of Beauty, Privacy & SophisticationNestled in the cultural heart of the Berkshires, just steps from downtown Lenox, this extraordinary property offers a rare and coveted blend of seclusion and sophistication set on an unheard-of 8 acres of wooded, professionally designed, and maturely landscaped grounds.Inside, the home has been completely reimagined, with every

Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

13 Taconic Ave, Lenox, MA 01240
/61
$1,790,000
- 6 Beds
- 6.5 Baths
- 5,115 Sq Ft
76 Lenox Rd, West Stockbridge, MA 01266

New World meets Old in this impeccably designed and elegant French Country inspired estate nestled perfectly on the hillside, affording gorgeous westerly mountain and sunset views. Situated on 3.76 acres, the home offers ample privacy, yet it is just a stone's throw from Tanglewood and downtown Lenox and West Stockbridge. Designed for hosting extended family and friends, it offers generously

Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

76 Lenox Rd, West Stockbridge, MA 01266
/47
$889,000
- 4 Beds
- 2 Baths
- 3,599 Sq Ft
2507 State Rd, Richmond, MA 01254

Welcome to Blue Spruce Farm, a magnificent 23-acre estate rich in history and brimming with enchanting features. Nestled in a serene setting, this certified wildlife habitat offers a sanctuary for nature lovers and a retreat from the bustle of everyday life. Enjoy leisurely walks on the maintained trails that meander through the 23 acres, offering tranquil views and a connection with nature. A

Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

2507 State Rd, Richmond, MA 01254
/43
$725,000
- 4 Beds
- 3 Baths
- 2,610 Sq Ft
770 Summer St Unit 15A, Lee, MA 01238

Enjoy unobstructed views of Laurel Lake from this first-floor unit at Lakeside at Foxhollow. This spacious 4-bedroom, 3-bath condo features two fully finished levels, two outdoor decks (including one waterfront), and two primary suites--one on each floor--plus resort-style amenities. The perfect opportunity to create your ideal lakeside retreat.The professionally managed community offers an

Tracy Crawford COMPASS MASSACHUSETTS , LLC GB

770 Summer St Unit 15A, Lee, MA 01238
/54
$979,000
- 5 Beds
- 4.5 Baths
- 2,800 Sq Ft
850 Summer St, Lee, MA 01238

Welcome to the Katydid Cottage, a thoughtfully updated Berkshire home full of modern amenities and historic charm. This five bedroom, four and a half bath freestanding condominium features a bright kitchen, large dining room, living room with gas fireplace insert, powder room, and a primary suite all on the first floor. Upstairs you will find four more bedrooms, two with ensuite bathrooms, and

Katie Williams STONE HOUSE PROPERTIES, LLC

850 Summer St, Lee, MA 01238
/56
$979,000
- 5 Beds
- 4.5 Baths
- 2,800 Sq Ft
850 Summer St Unit M14, Lee, MA 01238

Welcome to the Katydid Cottage, a thoughtfully updated Berkshire home full of modern amenities and historic charm. This five bedroom, four and a half bath freestanding condominium features a bright kitchen, large dining room, living room with gas fireplace insert, powder room, and a primary suite all on the first floor. Upstairs you will find four more bedrooms, two with ensuite bathrooms, and

Katie Williams STONE HOUSE PROPERTIES, LLC

850 Summer St Unit M14, Lee, MA 01238
/45
$1,499,000
- 4 Beds
- 4.5 Baths
- 3,190 Sq Ft
121 E Dugway Rd, Lenox, MA 01240

Stunning Georgian Colonial style home on a lovely 4A private lot is ready for its new owners! In pristine condition, this 4 BR, 4.5 baths home offers hardwood floors throughout, first floor Primary Suite, open great room concept with cherry cabinetry in kitchen and granite counters, gas fireplace in the great room, formal dining or music room and first floor study with full bath. The second

Mary Jo Piretti PIRETTI REAL ESTATE

121 E Dugway Rd, Lenox, MA 01240
/70
$1,290,000
- 3 Beds
- 2.5 Baths
- 2,844 Sq Ft
257 W Mountain Rd, Lenox, MA 01240

Nestled in the heart of the Berkshires, 257 W Mountain Road offers a rare blend of luxury and tranquility. This exquisite property is set on a serene, tree-lined road just minutes from downtown Lenox and Tanglewood. With refined finishes, spacious living areas, and walls of windows framing the lush landscape, every detail reflects elegance and comfort. The landscaped grounds feature stone

Nicole Moore KELLER WILLIAMS REALTY

257 W Mountain Rd, Lenox, MA 01240
/114
$929,900
- 4 Beds
- 2.5 Baths
- 3,608 Sq Ft
67 Dunmore Ct, Lenox, MA 01240

This gorgeous 4-bedroom, 3-bathroom home sits on a spacious corner lot surrounded by beautiful native landscaping, offering both privacy and curb appeal. Step inside to find a bright and inviting layout with ample space for entertaining and everyday living. The kitchen features newly redone floors (2025), and the large back deck provides the perfect space for outdoor gatherings or quiet

Sara Bresett NOCHER REALTY

67 Dunmore Ct, Lenox, MA 01240
/62
$1,750,000
- 4 Beds
- 4.5 Baths
- 4,349 Sq Ft
11 Blossom Hill, Lenox, MA 01240

Nestled within the beautifully landscaped grounds of Miraval Lenox, formerly the famed Cranwell Resort Spa and Golf Club, this spacious and light-filled residence offers a coveted Berkshire lifestyle with exclusive access to resort amenities.Enjoy a reduced-rate membership to Wyndhurst Club & Manor, featuring tennis courts, indoor and outdoor pools, a full fitness center, spa services, dining,

Paula McLean PAULA MCLEAN REALTORS INC.

11 Blossom Hill, Lenox, MA 01240
/68
$1,400,000
- 4 Beds
- 5 Baths
- 6,500 Sq Ft
160 High St, Lee, MA 01238

Once the First Methodist Episcopal Church, built in 1898, this incredible 6,500 sq ft property has been thoughtfully reimagined as a two-family residence and offers unparalleled potential for an artist's dream live/work space. Located just a short walk from downtown on a 3/4 lot abutting an 18 acre nature reserve, this building is ideally positioned to offer both the tranquility of the Berkshires

Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

160 High St, Lee, MA 01238
/49
$949,000
- 1 Bed
- 1.5 Baths
- 3,810 Sq Ft
30 Great Barrington Rd, West Stockbridge, MA 01266

The renovation of this 1930's Cape Cod by a master craftsman and his designer wife into the stunning modern day Contemporary it is today, while preserving some of the original highlights,is nothing short of a design miracle. The immense Great Room with the 60 foot wall of glass overlooking the terraced stone wall that leads to a stream and pine forest is the focal point of this special home. The

Cortney Dupont COHEN & WHITE ASSOCIATES

30 Great Barrington Rd, West Stockbridge, MA 01266
/70
$1,299,000
- 5 Beds
- 4 Baths
- 3,289 Sq Ft
49 Main St, Stockbridge, MA 01262

Improved stunning Stockbridge Village property that boasts an updated main house and includes a separate three apartment carriage house. The main property offers great natural light and ample common spaces that are gracious in size, updated lovely kitchen, five bedrooms, four baths, screened porch and inviting outdoor spaces. It has been thoughtfully updated while keeping the charm and character

Cortney Dupont COHEN & WHITE ASSOCIATES

49 Main St, Stockbridge, MA 01262
/48
$989,000
- 4 Beds
- 2.5 Baths
- 2,576 Sq Ft
144 Shore Rd, Richmond, MA 01254

WATERFRONT home on Richmond Pond. With 65' of frontage and over half an acre, this charming four season home has 4 bedrooms, 2 1/2 bathrooms and wonderful outdoor living areas. Gorgeous perennial gardens, a spacious patio off the kitchen/great room, fire pit, dock,and a rear garage door (perfect for boat access and storage) all while enjoying the beautiful lake views.. Once inside is a

Lori Rose STONE HOUSE PROPERTIES, LLC

144 Shore Rd, Richmond, MA 01254
/29
$912,000
- 4 Beds
- 4 Baths
- 2,280 Sq Ft
21 East St, Stockbridge, MA 01262

**Price Improvement** Nestled in the heart of the Berkshires, this spacious Colonial sits on over 14 acres, offering privacy, potential, and long-term value. Currently operating as a doggy day care, but you wouldn't know it when you walk inside! Well-maintained & cared for. Recent updates include the kitchen, bathrooms, carpets, back deck, and front landscaping, while still leaving room for

Brianna Boffoli Cameron Prestige, LLC

21 East St, Stockbridge, MA 01262
/38
$1,100,000
- 5 Beds
- 3.5 Baths
- 3,194 Sq Ft
33 Interlaken Rd, Stockbridge, MA 01262

Enjoy convenient one level living in this expanded contemporary ranch. Super location - Located less than 5 minutest to the main gates of Tanglewood, the Stockbridge Bowl for swimming, and Gould Meadows for a nature lovers hike. Sited at the end of a long winding driveway this 2+ acre parcel is level and sunny (ideal for a pool). 5+ bedrooms and 3 1/2 bathrooms including a suite with a

Lori Rose STONE HOUSE PROPERTIES, LLC

33 Interlaken Rd, Stockbridge, MA 01262
/63
$1,100,000
- 4 Beds
- 3.5 Baths
- 2,861 Sq Ft
1 Train Hill Rd, Stockbridge, MA 01262

This Stockbridge Colonial has it all....location, separate guest suite and plenty of country chic design. This historic home boasts all the charm of yesteryear with fabulous wide pine floors, state of the art country kitchen that retains it's charm, formal dining room with fireplace, gracious banister to the second floor of guest bedrooms with renovated bath all while seamlessly blending with the

Cortney Dupont COHEN & WHITE ASSOCIATES

1 Train Hill Rd, Stockbridge, MA 01262
/20
$3,995,000
- 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
/14
$240,000
- 1 Bed
- 1 Bath
- 800 Sq Ft
260 Pittsfield Rd Unit B-5, Lenox, MA 01240

Freshly updated 1 BR/1 BA condo at Lenox Heights. This light‑filled, 800 sq ft condo boasts a thoughtfully renovated kitchen with new cabinetry and stainless‑steel appliances, plus plush wall‑to‑wall carpeting for a fresh, clean aesthetic. Step outside onto your private balcony to enjoy your morning coffee. On‑site amenities include an outdoor

Samantha Homeyer BIRCH PROPERTIES

260 Pittsfield Rd Unit B-5, Lenox, MA 01240
/42
$485,000 Open Sat 10AM - 12PM
- 2 Beds
- 2 Baths
- 1,296 Sq Ft
42 East St, Stockbridge, MA 01262

Set on 6.4 scenic acres, this classic New England farmhouse captures the timeless spirit of Stockbridge, a town beloved for its rich history and cultural legacy. This 2-bed 2-bath home offers authentic charm, featuring beautiful hardwood floors, a spacious kitchen, family room + 1st floor full bath, and a welcoming front porch that evokes a slower, simpler time. Thoughtful updates include a newer

Conor Meehan STONE HOUSE PROPERTIES, LLC

42 East St, Stockbridge, MA 01262
/13
$290,000
- 1 Bed
- 1 Bath
- 709 Sq Ft
3 Morgan Manor Unit 3 - 8, Lenox, MA 01240

Welcome to 3‑8 Morgan Manor, a charming one-bedroom condo nestled in the heart of Lenox Village. This move-in-ready unit offers a sunlit layout with cozy carpeting, and efficient space. The condo fee includes heat, hot water, gas, water, and sewer, making for truly hassle-free living. Located in a well-maintained building just steps from downtown Lenox, you'll enjoy easy access to

Katie Soules WILLIAM RAVEIS REAL ESTATE

3 Morgan Manor Unit 3 - 8, Lenox, MA 01240
/5
$129,900
- 3 Beds
- 2 Baths
- 1,000 Sq Ft
11 Jennifer Ln, West Stockbridge, MA 01266

Spacious 1998 Titan double-wide with 3 bedrooms, 2 baths, cathedral ceilings, and an open living area. Features a cozy fireplace and efficient pellet stove. The primary suite includes a private bath and ample closet space. Bright kitchen and dining area with plenty of storage. Great layout for comfortable living in a peaceful setting.

John Ciepiela BISHOP WEST REAL ESTATE

11 Jennifer Ln, West Stockbridge, MA 01266
/48
$379,000
- 4 Baths
- 10,712 Sq Ft
1515 State Rd, Richmond, MA 01254

Discover the possibilities in this stunning 10,712-square-foot former church, gracefully situated on a serene rural parcel surrounded by open skies and quiet landscapes. With soaring ceilings, architectural glass accents, and original contemporary details, this one-of-a-kind property blends timeless beauty with endless potential.Currently zoned for residential use, this expansive structure offers

Tim Gallagher STONE HOUSE PROPERTIES, LLC

1515 State Rd, Richmond, MA 01254
/13
$313,000
- 2 Beds
- 3 Baths
- 1,770 Sq Ft
2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240

If you are looking for location, Rolling Hills is the place to be. Just minutes from Tanglewood, Shakespeare & Company, skiing, arts, and all of the Culture the Berkshires has to offer. This unit is right across from the Clubhouse/Pool/fitness room. This unit has 2 bedrooms, 3 baths, and additional family room on the lower level. Enjoy the Tennis/pickle ball courts or take swim in the pool or

Toni Marie Gage SIGNATURE ASSOCIATES

2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240
/58
$4,995,000
- 7 Beds
- 8 Baths
- 13,261 Sq Ft
319 Under Mountain Rd, Lenox, MA 01240

Pine Needles.Built circa 1900 as a Berkshire ''cottage'' in the era of grand summer estates, this historic property blends the dignity of Colonial Revival architecture with the relaxed elegance of an Italian villa and the artisanal detail of the Arts & Crafts movement. Sited on 80 private acres just minutes from the heart of Lenox, the estate offers breathtaking southern views, rolling forest,

Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

319 Under Mountain Rd, Lenox, MA 01240
/37
$289,000
- 2 Beds
- 1 Bath
- 1,155 Sq Ft
19 Great Barrington Rd, West Stockbridge, MA 01266

Two to three bedroom country colonial just minutes from West Stockbridge Village. Large 1.26 acre level lot is perfect for entertaining and relaxation day or night! Direct access to Card Pond; close proximity to Tanglewood, shopping, dining, galleries, theatre, hiking/biking, boating and all the cultural and recreational amenities of South Berkshire County and beyond. Bring your vision and

Amy Wood STEEPLEVIEW REALTY - N. ADAMS

19 Great Barrington Rd, West Stockbridge, MA 01266
/47
$579,000
- 4 Beds
- 2.5 Baths
- 2,040 Sq Ft
65 Pease Terrace, Lee, MA 01238

This lovely home boasts 4 generously sized bedrooms with hardwood floors, primary has ensuite bath. It also has a 2nd full and 1 half bath. Large family room with vaulted ceiling, substantial deck on one side & screened porch on opposite side. Hardwood floors in formal dining room & beautiful living room with fireplace. French doors from living room to screened-in porch. A Buderus Boiler for

Mary Blair SIGNATURE ASSOCIATES

65 Pease Terrace, Lee, MA 01238
/58
$635,000
- 3 Beds
- 3 Baths
- 2,476 Sq Ft
4 Main St, West Stockbridge, MA 01266

Don't miss this one-of-a-kind opportunity to own a commercially zoned, mixed-use property offering exceptional live/work potential in a prime in-town location along the Williams River. This uniquely designed 3-bedroom, 3-bath home includes a versatile accessory apartment, making it ideal for those seeking a combination of residential comfort and business flexibility. Enjoy water views from two

Conor Meehan STONE HOUSE PROPERTIES, LLC

4 Main St, West Stockbridge, MA 01266
/23
$523,995
- Land
- 10 Acres
- $52,279 per Acre
0 Swamp Rd, Richmond, MA 01254

This 10-acre parcel in scenic Richmond, available for the first time in generations, offers a rare chance to build your dream home in the heart of the Berkshires. Surrounded by open farmland and natural beauty, this property provides a peaceful and inspiring setting for a country retreat or a year-round residence. The land features gently rolling meadows filled with wildflowers and native

Conor Meehan STONE HOUSE PROPERTIES, LLC

0 Swamp Rd, Richmond, MA 01254
/38
$710,000
- 3 Beds
- 2 Baths
- 2,081 Sq Ft
51 New Lenox Rd, Lenox, MA 01240

Meticulous craftsmanship and timber frame construction define this charming Colonial Dutch gambrel residence, combining comfort and practicality for everyday living. High-grade timber framing and solid construction give this home character and a warm, inviting atmosphere with its wood accents.Gather around the stone fireplace in the inviting living room, or whip up meals in the kitchen equipped

Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

51 New Lenox Rd, Lenox, MA 01240
/26
$425,000
- 3 Beds
- 1 Bath
- 1,344 Sq Ft
153 E Dugway Rd, Lenox, MA 01240

**Opportunity Awaits!**Great Lenox location. Three bedroom, one bath Ranch style home is nestled on 1.14 acres of land on a picturesque street, this gem offers 1344 sq ft on the main floor, with a full walkout lower level to a beautiful large yard. Minutes to downtown, Tanglewood and the best of the Berkshires.

Matt Carlino MACCARO REAL ESTATE

153 E Dugway Rd, Lenox, MA 01240
/57
$635,000
- 3 Beds
- 2.5 Baths
- 1,720 Sq Ft
4 Evergreen Trail, Lenox, MA 01240

Heirloom peonies and fragrant David Austin rose varieties adorn the walkway of this Berkshire hidden gem inviting you into tranquillity, peace and calm. Once indoors, you'll find easy living. The first level has an open kitchen and living area with a gas fireplace, large primary bedroom with a full bath and walk-in closet along with a screened in patio which overlooks a well established low

Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

4 Evergreen Trail, Lenox, MA 01240

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