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Berkshire County, MA Homes for Sale with Pool

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  • 250 West St, Lenox, MA 01240
    250 West St, Lenox, MA 01240
    250 West St, Lenox, MA 01240
    /54

    $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

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 423-1264

    250 West St, Lenox, MA 01240
  • 8 Apache Dr, North Adams, MA 01247
    8 Apache Dr, North Adams, MA 01247
    8 Apache Dr, North Adams, MA 01247
    /14

    $149,000

    • 2 Beds
    • 1 Bath
    • 757 Sq Ft

    8 Apache Dr, North Adams, MA 01247

    Be the first to live in this brand-new, never-occupied single-wide manufactured home! Thoughtfully designed with upgraded features throughout, this home offers modern style and comfort. The spacious living room features an accent wall with built-in shelving and cabinet storage. The kitchen is beautifully appointed with a deep sink, dishwasher, and side-by-side stainless refrigerator with ice

    Agent Photo

    Peter West

    BISHOP WEST REAL ESTATE

    (413) 423-0613

    8 Apache Dr, North Adams, MA 01247
  • 1333 Norfolk Rd, Southfield, MA 01259
    1333 Norfolk Rd, Southfield, MA 01259
    1333 Norfolk Rd, Southfield, MA 01259
    /64

    $3,250,000

    • 6 Beds
    • 5.5 Baths
    • 4,681 Sq Ft

    1333 Norfolk Rd, Southfield, MA 01259

    Set on 11 enchanting acres in the pastoral town of New Marlborough, Massachusetts, this exceptional Berkshires estate offers a rare convergence of architectural refinement, natural splendor, and modern luxury. Designed by an architect and originally built in 1984, the main house, guest house, and pool house were all fully renovated in early 2025 to create a cohesive, contemporary compound with

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 327-9228

    1333 Norfolk Rd, Southfield, MA 01259
  • 100 Elaine Dr, Pittsfield, MA 01201
    100 Elaine Dr, Pittsfield, MA 01201
    100 Elaine Dr, Pittsfield, MA 01201
    /45

    $399,999

    • 4 Beds
    • 2 Baths
    • 1,470 Sq Ft

    100 Elaine Dr, Pittsfield, MA 01201

    Welcome to this beautifully maintained ranch offering the perfect blend of comfort, style and functionality. This move in ready home features 4 bedrooms , 2 full baths and a finished basement. Step inside to find wood floors, a warm and inviting layout with plenty of natural lightening. The kitchen opens to the dinning area. Outside enjoy a lovely front porch for morning coffee, in the backyard

    Agent Photo

    Kellie Perrault

    KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

    (413) 422-6204

    100 Elaine Dr, Pittsfield, MA 01201
  • 764 E Hill Rd, New Marlborough, MA 01230
    764 E Hill Rd, New Marlborough, MA 01230
    764 E Hill Rd, New Marlborough, MA 01230
    /40

    $4,995,000

    • 5 Beds
    • 5.5 Baths
    • 5,002 Sq Ft

    764 E Hill Rd, New Marlborough, MA 01230

    WHERE THE WORLD FALLS AWAY 227 acres. 227 years. At East Hill Road's summit, East Hill Farm is a fully realized estate where infrastructure, land, and possibility are complete and in place. The 1798 Thomas Shepard House-museum-quality restoration featuring 5 bedrooms, 5.5 baths, 5 fireplaces, original King's board floors, hand-blown glass windows-awaits your vision for kitchens and baths. Modern

    Karen Climo William Pitt Sotheby's Int'l

    764 E Hill Rd, New Marlborough, MA 01230
  • 1 Rolling Hills Unit 10, Lenox, MA 01240
    1 Rolling Hills Unit 10, Lenox, MA 01240
    1 Rolling Hills Unit 10, Lenox, MA 01240
    /18

    $389,900

    • 2 Beds
    • 2 Baths
    • 1,576 Sq Ft

    1 Rolling Hills Unit 10, Lenox, MA 01240

    Unique opportunity to own a beautifully updated condo. This inviting home offers 2 bedrooms and 2 full bathrooms, a gorgeous updated kitchen, and a finished room in the basement perfect for a home office, gym, or additional living space. Enjoy outdoor living with two porches, and note that the unit may be offered furnished for added convenience. All this nestled in the heart of the picturesque

    Michele Purcell Lamacchia Realty, Inc.

    1 Rolling Hills Unit 10, Lenox, MA 01240
  • 37 Corey Rd Unit 73, Hancock, MA 01237
    37 Corey Rd Unit 73, Hancock, MA 01237
    37 Corey Rd Unit 73, Hancock, MA 01237
    /24

    $255,000

    • 2 Beds
    • 2 Baths
    • 842 Sq Ft

    37 Corey Rd Unit 73, Hancock, MA 01237

    Country Village living...just listed is this recently renovated 2-bedroom unit which offers 2 full bathrooms also recently renovated. New floors throughout with no carpet. A gorgeous redone stone wood burning fireplace for those cold nights. A recently renovated kitchen with new appliances, granite countertops and wood cabinets. Enjoy the back deck with beautiful views of the mountains.

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 73, Hancock, MA 01237
  • 890 Bald Mountain Rd, Austerlitz, NY 12017
    890 Bald Mountain Rd, Austerlitz, NY 12017
    890 Bald Mountain Rd, Austerlitz, NY 12017
    /39

    $7,950,000

    • 5 Beds
    • 4.5 Baths
    • 6,438 Sq Ft

    890 Bald Mountain Rd, Austerlitz, NY 12017

    Located in a private gated community of large acreage land holders, this exquisite enclave of 3 homes on 84 acres has been listed in Interior Design magazine. The main house is a stunning post and beam contemporary home, combining steel, stone, wood and glass panels. It overlooks the gunite pool, surrounded by stone walls and the two additional designed and inviting cottages. Continuing past the

    Janet Kain The Kinderhook Group, Inc.

    890 Bald Mountain Rd, Austerlitz, NY 12017
  • 9 October Hill Dr, Lenox, MA 01240
    9 October Hill Dr, Lenox, MA 01240
    9 October Hill Dr, Lenox, MA 01240
    /60

    $1,585,000

    • 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
  • 33 Alpine Trail, Pittsfield, MA 01201
    33 Alpine Trail, Pittsfield, MA 01201
    33 Alpine Trail, Pittsfield, MA 01201
    /69

    $730,000

    • 5 Beds
    • 4.5 Baths
    • 3,381 Sq Ft

    33 Alpine Trail, Pittsfield, MA 01201

    Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The main level boasts vaulted ceilings with open bright common areas, great room with wood flooring and gas fireplace, updated kitchen, dining room with views, primary bedroom with newly renovated en suite bath, oversized garage, half bathroom and private screened porch and deck to take in the fresh air and

    Cortney Dupont COHEN & WHITE ASSOCIATES

    33 Alpine Trail, Pittsfield, MA 01201
  • 103 Alpine Trail, Pittsfield, MA 01201
    103 Alpine Trail, Pittsfield, MA 01201
    103 Alpine Trail, Pittsfield, MA 01201
    /39

    $759,000

    • 3 Beds
    • 2.5 Baths
    • 2,381 Sq Ft

    103 Alpine Trail, Pittsfield, MA 01201

    Thoughtfully updated end unit located at the Pines at Bousquet The first level includes a gracious entry with custom flooring and cedar hall closet that flows beautifully into the great room with vaulted ceilings, gas fireplace and glass doors to the screened porch and deck with a scenic view of the woods. The lovely updated kitchen is open to the dining area and great room for comfortable open

    Cortney Dupont COHEN & WHITE ASSOCIATES

    103 Alpine Trail, Pittsfield, MA 01201
  • 6 Thrushwood Ln, Great Barrington, MA 01230
    6 Thrushwood Ln, Great Barrington, MA 01230
    6 Thrushwood Ln, Great Barrington, MA 01230
    /32

    $1,475,000

    • 5 Beds
    • 4 Baths
    • 4,200 Sq Ft

    6 Thrushwood Ln, Great Barrington, MA 01230

    MOTIVATED SELLER; WILLING TO NEGOTIATE ON UPGRADES AND IMPROVEMENTS. Indulge in refined Berkshire living on an exclusive cul-de-sac, where effortless HOA services complement this exquisite new construction. Offering 4,200 sq ft of thoughtfully designed, environmentally conscious living less than a mile from downtown Great Barrington, this home is the perfect modern retreat. Enter through a

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    6 Thrushwood Ln, Great Barrington, MA 01230
  • 165 Kemble St Unit 5, Lenox, MA 01240
    165 Kemble St Unit 5, Lenox, MA 01240
    165 Kemble St Unit 5, Lenox, MA 01240
    /25

    $3,200,000

    • 2 Beds
    • 2.5 Baths
    • 1,956 Sq Ft

    165 Kemble St Unit 5, Lenox, MA 01240

    A Rare South-Facing Retreat at The Residences at Canyon RanchNestled within the serene, world-renowned Canyon Ranch Lenox campus, this two-bedroom, two-and-a-half-bath end unit is a rare offering--south-facing, luminous, and among the most private of its kind. More than a residence, it is an invitation to a life of balance, wellness, and quiet sophistication in the cultural heart of the

    Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    165 Kemble St Unit 5, Lenox, MA 01240
  • 1786 S Undermountain Rd, Sheffield, MA 01257
    1786 S Undermountain Rd, Sheffield, MA 01257
    1786 S Undermountain Rd, Sheffield, MA 01257
    /17

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 2,408 Sq Ft

    1786 S Undermountain Rd, Sheffield, MA 01257

    Classic 3-Bedroom Cape with Pool - Perfectly positioned between NW Connecticut and Sheffield, MA in the Berkshires. Sheffield is the oldest Town in Berkshire County - the township was purchased in 1724 from Chief Konkapot and other Stockbridge Native Americans. This bright, lovely 3-Bedroom Cape features a beautiful, heated pool, a Bedroom and Full Bath on the Main Floor, 2 Bedrooms and another

    Juliet Moore ELYSE HARNEY REAL ESTATE

    1786 S Undermountain Rd, Sheffield, MA 01257
  • 1476 County Route 5, Canaan, NY 12029
    1476 County Route 5, Canaan, NY 12029
    1476 County Route 5, Canaan, NY 12029
    /40

    $579,000

    • 3 Beds
    • 2 Baths
    • 2,300 Sq Ft

    1476 County Route 5, Canaan, NY 12029

    Set on three peaceful acres along a quiet country road, this 3-bedroom ranch home captures the very best of Upstate living. With long views of the Berkshire Hills as the backdrop from your in-ground pool, the 3-acre property offers both privacy and convenience as well as nearby Berkshire attractions such as Tanglewood, Red Lion Inn and The Norman Rockwell Museum. You are also less than 30 minutes

    Chris Getman Houlihan Lawrence Inc.

    1476 County Route 5, Canaan, NY 12029
  • 221 Bailey Rd, Lanesborough, MA 01237
    221 Bailey Rd, Lanesborough, MA 01237
    221 Bailey Rd, Lanesborough, MA 01237
    /56

    $1,200,000

    • 3 Beds
    • 3.5 Baths
    • 4,248 Sq Ft

    221 Bailey Rd, Lanesborough, MA 01237

    Welcome to 221 Bailey Road in Lanesboro, MA., an exquisite ranch-style home offering approximately 4,200 sqft of luxurious living space. Nestled on 87 acres atop a mountain, this property provides unparalleled privacy and breathtaking views that enhance its serene atmosphere. The open-concept living area is perfect for entertaining, featuring abundant natural light and seamless flow between

    Doug Collins LAMACCHIA REALTY, INC

    221 Bailey Rd, Lanesborough, MA 01237
  • 19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
    /47

    $585,000

    • 2 Beds
    • 2.5 Baths
    • 1,935 Sq Ft

    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262

    MOTIVATED SELLER! Beautiful Carriage Barn Unit located in the sought after White Pines. The main level has open common spaces that include a gracious great room with a wall of windows to let in the natural light, wet bar and wood burning fireplace. Generous dining room overlooking the picturesque sun porch with serene view and galley kitchen that is oversized with ample storage space and laundry

    Cortney Dupont COHEN & WHITE ASSOCIATES

    19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
  • 37 Corey Rd Unit 234, Hancock, MA 01237
    37 Corey Rd Unit 234, Hancock, MA 01237
    37 Corey Rd Unit 234, Hancock, MA 01237
    /13

    $159,900

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft

    37 Corey Rd Unit 234, Hancock, MA 01237

    TOP FLOOR COUNTRY INN UNIT! At the base of Jiminy Peak, skiing is just steps from your door in one of these one bedroom all suites' condominiums with kitchens that offer the charm of a countryside inn and the conveniences of a slope side hotel. Whirlpools, year-round outdoor swimming pool, exercise room, in house restaurant and on-site front desk services makes this and easy decision to own.

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 234, Hancock, MA 01237
  • 148 Maple Ave Unit 12, Great Barrington, MA 01230
    148 Maple Ave Unit 12, Great Barrington, MA 01230
    148 Maple Ave Unit 12, Great Barrington, MA 01230
    /15

    $397,600

    • 1 Bed
    • 1 Bath
    • 568 Sq Ft

    148 Maple Ave Unit 12, Great Barrington, MA 01230

    Nestled amidst the picturesque embrace of Great Barrington, where the harmonious blend of nature and small-town charm unfolds, The Laurel beckons you into a realm of opulence and refinement. As you step inside, a grand two-story glass atrium lobby welcomes you with a breathtaking display of contemporary design and lavish furnishings. Lush plants and waterfalls adorn the walls, seamlessly

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    148 Maple Ave Unit 12, Great Barrington, MA 01230
  • 21A Interlaken Rd, Stockbridge, MA 01262
    21A Interlaken Rd, Stockbridge, MA 01262
    21A Interlaken Rd, Stockbridge, MA 01262
    /43

    $3,850,000

    • 4 Beds
    • 3.5 Baths
    • 4,000 Sq Ft

    21A Interlaken Rd, Stockbridge, MA 01262

    Modern country living at its finest--crafted with exceptional quality, refined taste, and a true sense of warmth. A dramatic double-height entry and living room create a seamless dialogue with the surrounding landscape while offering the comfort of home. The main level features an open-concept kitchen, living, and dining area, anchored on one side by the primary suite and on the other by a

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    21A Interlaken Rd, Stockbridge, MA 01262
  • 100 Northumberland Rd, Pittsfield, MA 01201
    100 Northumberland Rd, Pittsfield, MA 01201
    100 Northumberland Rd, Pittsfield, MA 01201
    /62

    $549,000

    • 4 Beds
    • 4 Baths
    • 3,008 Sq Ft

    100 Northumberland Rd, Pittsfield, MA 01201

    Welcome to 100 Northumberland Road - Storybook Berkshire Retreat where timeless charm meets exceptional space and possibility. Located in south east Pittsfield this home sits on .44 acres offering an inviting blend of elegance, comfort & room to grow. Inside, generous living spaces, sun filled rooms, rich architectural details and thoughtful updates create an environment perfect for both everyday

    Laura Arseneau PAULA MCLEAN REALTORS INC.

    100 Northumberland Rd, Pittsfield, MA 01201
  • 84 Undermountain Rd, Egremont, MA 01230
    84 Undermountain Rd, Egremont, MA 01230
    84 Undermountain Rd, Egremont, MA 01230
    /63

    $2,495,000

    • 5 Beds
    • 3.5 Baths
    • 6,254 Sq Ft

    84 Undermountain Rd, Egremont, MA 01230

    Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it

    Tony Segalla LANCE VERMEULEN RE, INC

    84 Undermountain Rd, Egremont, MA 01230
  • 9102 Mountainside Dr, Hancock, MA 01237
    9102 Mountainside Dr, Hancock, MA 01237
    9102 Mountainside Dr, Hancock, MA 01237
    /32

    $689,000

    • 3 Beds
    • 3 Baths
    • 1,968 Sq Ft

    9102 Mountainside Dr, Hancock, MA 01237

    Step into this beautifully updated 3-bedroom, 3-bathroom retreat nestled in one of Jiminy's most family-friendly neighborhoods. 2 bedrooms and 2 Full baths on the 1st floor. The open-concept living area features floor-to-ceiling windows that flood the space with natural light, highlighting the elegant hardwood flooring and cozy fireplace. The gourmet kitchen boasts quartz countertops and

    Kevin Moderski JIMINY REALTY

    9102 Mountainside Dr, Hancock, MA 01237
  • 37 Corey Rd Unit 526, Hancock, MA 01237
    37 Corey Rd Unit 526, Hancock, MA 01237
    37 Corey Rd Unit 526, Hancock, MA 01237
    /18

    $147,000

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft

    37 Corey Rd Unit 526, Hancock, MA 01237

    At the base of Jiminy Peak, skiing is just steps from your door in one of these one bedroom all suites' condominiums with kitchens that offer the charm of a countryside inn and the conveniences of a slope side hotel. Whirlpools, year-round outdoor swimming pool, exercise room, in house restaurant and on-site front desk services makes this and easy decision to own. Excellent rental history and no

    Kevin Moderski JIMINY REALTY

    37 Corey Rd Unit 526, Hancock, MA 01237
  • 905 West Rd, Great Barrington, MA 01230
    905 West Rd, Great Barrington, MA 01230
    905 West Rd, Great Barrington, MA 01230
    /60

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 2,204 Sq Ft

    905 West Rd, Great Barrington, MA 01230

    Welcome to Serenity Hill.This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road.

    William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    905 West Rd, Great Barrington, MA 01230
  • 25 Calumet St, Pittsfield, MA 01201
    25 Calumet St, Pittsfield, MA 01201
    25 Calumet St, Pittsfield, MA 01201
    /61

    $365,000

    • 4 Beds
    • 1.5 Baths
    • 1,600 Sq Ft

    25 Calumet St, Pittsfield, MA 01201

    This well-loved home offers 4 bedrooms and 1.5 baths on a very large lot with beautiful open views. A classic enclosed front porch welcomes you inside, where old-world molding, window seats, hardwood floors, and handsome laminate flooring add warmth and character throughout.The spacious kitchen is fully applianced and features plenty of cabinetry, flowing into a separate breakfast/dining room

    Nick Geranios WILLIAM PITT SOTHEBY'S - LENOX

    25 Calumet St, Pittsfield, MA 01201
  • 65 Crofut St, Pittsfield, MA 01201
    65 Crofut St, Pittsfield, MA 01201
    65 Crofut St, Pittsfield, MA 01201
    /68

    $1,350,000

    • 5 Beds
    • 4.5 Baths
    • 4,948 Sq Ft

    65 Crofut St, Pittsfield, MA 01201

    Designed in 1929 by noted architect Henry Seaver (Berkshire Museum, Lenox Town Hall), this distinguished Georgian Colonial was once the centerpiece of Pittsfield's social scene. The home preserves exquisite 18th-century details - mantels, wainscoting, and finely crafted woodwork salvaged from two of the city's earliest residences, making it a living piece of Berkshire history. Set back on 2.5

    Conor Meehan STONE HOUSE PROPERTIES, LLC

    65 Crofut St, Pittsfield, MA 01201
  • 2999 New York 23, Hillsdale, NY 12529
    2999 New York 23, Hillsdale, NY 12529
    2999 New York 23, Hillsdale, NY 12529
    /32

    $895,000

    • 4 Beds
    • 2.5 Baths
    • 2,225 Sq Ft

    2999 New York 23, Hillsdale, NY 12529

    Classic Country Home with Pond, Pool & Barns Located just minutes from Catamount Ski Area, Hudson, NY, and Great Barrington, MA. Steeped in history and charm, this distinctive residence—believed to date back to the late 1800s—offers timeless character with thoughtful updates and plenty of space to enjoy country living.This 4 BR, 2.5 BA, 2,225± sq. ft. home is sited on 12+ acres. The rocking

    Lindsay Lebrecht Copake Lake Realty Corp.

    2999 New York 23, Hillsdale, NY 12529
  • 377 Highland Way, Sandisfield, MA 01255
    377 Highland Way, Sandisfield, MA 01255
    377 Highland Way, Sandisfield, MA 01255
    /62

    $475,000

    • 4 Beds
    • 3 Baths
    • 1,188 Sq Ft

    377 Highland Way, Sandisfield, MA 01255

    Welcome to your dream getaway in Otis Woodlands, one of the Berkshires' premiere private communities. This beautiful home offers the perfect blend of rustic elegance and modern comfort, ideal for year-round living or a serene weekend escape.Nestled among the trees, this spacious 4-bedroom, 3-bathroom home features a dramatic great room with vaulted ceilings and exposed beams, complemented by a

    Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

    377 Highland Way, Sandisfield, MA 01255
  • 30 East Rd, West Stockbridge, MA 01266
    30 East Rd, West Stockbridge, MA 01266
    30 East Rd, West Stockbridge, MA 01266
    /95

    $13,500,000

    • 7 Beds
    • 9 Baths
    • 10,429 Sq Ft

    30 East Rd, West Stockbridge, MA 01266

    Majestic 71 acre Tudor Estate atop Tom Ball Mountain in the quaint hamlet of Alford, MA. Enjoy total privacy and breathtaking views from nearly every room. The main house features 5 en-suite bedrooms, a gourmet kitchen, formal living and dining rooms, den, family room, gym, billiard room and massage room. A separate 2-bedroom guest house offers beamed ceilings and full amenities. Manicured

    Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    30 East Rd, West Stockbridge, MA 01266
  • 319 Under Mountain Rd, Lenox, MA 01240
    319 Under Mountain Rd, Lenox, MA 01240
    319 Under Mountain Rd, 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
  • 3243 County Route 9, East Chatham, NY 12060
    3243 County Route 9, East Chatham, NY 12060
    3243 County Route 9, East Chatham, NY 12060
    /51

    $2,000,000

    • 3 Beds
    • 3 Baths
    • 3,030 Sq Ft

    3243 County Route 9, East Chatham, NY 12060

    Welcome to Bear Paw Creek. Explore this captivating 24.68-acre retreat in East Chatham, New York, where a private drive leads to an idyllic blend of historic charm and contemporary elegance in an 1825 farmhouse. Featured in Domino Magazine this designer home is nestled amid rolling pastoral valleys, dense woods, and a gently flowing stream, the property unfolds with sublime gardens, a unique

    Patrick Heffernan Compass Greater NY, LLC

    3243 County Route 9, East Chatham, NY 12060
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /60

    $5,475,000

    • 5 Beds
    • 8 Baths
    • 9,400 Sq Ft

    Unlisted Address

    Nestled in the heart of Alford, Massachusetts, this extraordinary 35.6-acre Berkshire County estate offers unparalleled privacy with sweeping western Catskill Mountain views and direct access to conservation land. The impressive 9,400 sq ft main residence, built in 2003 and comprehensively updated beginning in 2020, features 4 bedrooms, 5 full baths, and resort-caliber amenities throughout its

    Elyse Morris ELYSE HARNEY REAL ESTATE

    Unlisted Address
  • 200 Old Stockbridge Rd, Stockbridge, MA 01262
    200 Old Stockbridge Rd, Stockbridge, MA 01262
    200 Old Stockbridge Rd, Stockbridge, MA 01262
    /30

    $895,000

    • 3 Beds
    • 2.5 Baths
    • 2,218 Sq Ft

    200 Old Stockbridge Rd, Stockbridge, MA 01262

    Welcome to The Vanna Building at Winden Hill. An excuisite example of Period living, this sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms and two baths on the second floor. The primary suite

    Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

    200 Old Stockbridge Rd, Stockbridge, MA 01262
  • 45 Forest St, Lee, MA 01238
    45 Forest St, Lee, MA 01238
    45 Forest St, Lee, MA 01238
    /42

    $1,399,900

    • 12 Beds
    • 7 Baths
    • 7,956 Sq Ft

    45 Forest St, Lee, MA 01238

    This stunning 6-family home sits on 1.5 acres, a large lot that goes from Forest St to Silver St, a convenient location with easy access to the Mass Pike and just a couple minutes away from the Lee Outlets. This multi-family consists of 3 two-bedroom units, 2 one-bedroom units, and a 4 bedroom 2 bath unit. The large unit offers a welcoming front porch, living room, eat-in kitchen, full bath and

    Maria Liccardi Kempf-Vanderburgh Realty Consultants, Inc.

    45 Forest St, Lee, MA 01238
  • 15 East St, Stockbridge, MA 01262
    15 East St, Stockbridge, MA 01262
    15 East St, Stockbridge, MA 01262
    /16

    $1,800,000

    • 40 Beds
    • 20 Baths
    • 30,000 Sq Ft

    15 East St, Stockbridge, MA 01262

    Located in a Sngle Family zoned area on a desirablle, private parcel consisting of nine total buildings with an in-ground pool amongst other amenities. Property is available for sale, lease or equity investment by new partners. This is an amazing property on the border of Stockbridge and Lenox with close proximity to Albany / Hartford / I-91. Many opportunities for possible hotel, B&B, family

    Tim Damon Mercury Real Estate

    15 East St, Stockbridge, MA 01262
  • 14 Calvin Cole Rd, Stephentown, NY 12169
    14 Calvin Cole Rd, Stephentown, NY 12169
    14 Calvin Cole Rd, Stephentown, NY 12169
    /66

    $679,000

    • 5 Beds
    • 3.5 Baths
    • 3,200 Sq Ft

    14 Calvin Cole Rd, Stephentown, NY 12169

    Masterfully crafted and custom-built 5BR/3.5BA home perfectly blending luxurious amenities w/resort style living from the theatre room to the backyard oasis. Gourmet kitchen w/quartz counters/island, prep sink, custom cabinets & professional-grade appliances including a Sub Zero Refrigerator. Upscale porcelain/LVP flooring & fun patchwork carpet complement high-end features. HUGE primary w/lavish

    John DiBlasi DiBlasi Real Estate

    14 Calvin Cole Rd, Stephentown, NY 12169
  • 0 Island Acres Rd Unit 73459836, Blandford, MA 01008
    0 Island Acres Rd Unit 73459836, Blandford, MA 01008
    0 Island Acres Rd Unit 73459836, Blandford, MA 01008
    /11

    $30,000

    • Land
    • 1.9 Acres
    • $15,789 per Acre

    0 Island Acres Rd Unit 73459836, Blandford, MA 01008

    Discover nearly two acres of tranquil, buildable land tucked away in a peaceful and private setting just moments from the beautiful Otis Reservoir. Whether you’re dreaming of a year-round residence or a relaxing vacation retreat, this property offers the perfect backdrop. Enjoy easy access to four-season recreation with skiing close by in the winter and boating, swimming, and outdoor adventures

    Nicole Baginski Chestnut Oak Associates

    0 Island Acres Rd Unit 73459836, Blandford, MA 01008
  • 20 Cooper Rd, Great Barrington, MA 01230
    20 Cooper Rd, Great Barrington, MA 01230
    20 Cooper Rd, Great Barrington, MA 01230
    /53

    $935,000

    • 4 Beds
    • 2.5 Baths
    • 2,631 Sq Ft

    20 Cooper Rd, Great Barrington, MA 01230

    This is the one you've been waiting for. A classic mid-century home on over 4 private acres, offering the ultimate Berkshire lifestyle. The bright, open-mid century floor plan provides a seamless flow, while two fireplaces add classic comfort. The home features 4 bedrooms, 3 baths, large office and a media room, offering flexibility for family and guests. Outside, your private resort awaits. A

    Tony Segalla LANCE VERMEULEN RE, INC

    20 Cooper Rd, Great Barrington, MA 01230
  • 241 Cunningham Hill Rd, Canaan, NY 12029
    241 Cunningham Hill Rd, Canaan, NY 12029
    241 Cunningham Hill Rd, Canaan, NY 12029
    /64

    $12,500,000

    • 4 Beds
    • 6 Baths
    • 6,829 Sq Ft

    241 Cunningham Hill Rd, Canaan, NY 12029

    A Home like no other. You will simply not find a Property like PIERCE PEAK, anywhere. AIA Award Winning Architectural Design by Burr & Mc Callum, crested upon the summit of Cunningham Hill (site cleared for HELIPAD). Open plan living with Indoor and Outdoor Living Rooms. Gourmet Kitchen, 2 Primary and 2 connnected Loft spaces. 2 Bedroom Guest Quarters (that can sleep 8), and Infinity Pool with

    Steven Weisz William Pitt Sothebys Intn'l

    241 Cunningham Hill Rd, Canaan, NY 12029

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In Berkshire County, there are currently 73 homes for sale with a pool, providing a refreshing retreat and a space for leisure. Whether it's a house for sale with a pool for those warm summer days, or a property featuring an indoor or screened-in pool for year-round enjoyment, these homes offer recreation right at home. Additionally, buyers can consider properties with access to community pools, offering a convenient space for relaxation and socializing. Whether you prefer a private pool or the convenience of a community pool, browse homes for sale with a pool in Berkshire County, MA and discover your ideal residence.

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