Berkshire County MA Homes for Sale with Pool

/32
$449,000
- 3 Beds
- 2 Baths
- 1,931 Sq Ft
16 Windflower Way, Williamstown, MA 01267

Welcome to this charming, freshly painted throughout and carpeted, 3-bedroom, 2 -bathroom condominium located in the desirable Greylock Village. This end unit offers comfort, convenience, and access to a peaceful and picturesque setting in the heart of the Berkshires. Whether you're looking for a full-time residence or a vacation getaway, this property is perfect for all lifestyles. The large

Kim Burnham BURNHAM GOLD REAL ESTATE, LLC

16 Windflower Way, Williamstown, MA 01267
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/24
$359,000
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
37 Corey Rd Unit 63, Hancock, MA 01237

Country Village living at its finest. This 3-bedroom 2 bath unit also has a loft. The views off the back deck are amazing. Keep warm during the winter months with the wood burning fireplace in the living room. 3 levels of living so plenty of space for the larger families or friends. Full size kitchen. Full size washer & dryer are included.

Kevin Moderski JIMINY REALTY

37 Corey Rd Unit 63, Hancock, MA 01237
/32
$129,000
- 1 Bed
- 1 Bath
- 800 Sq Ft
759 N Main Rd, Otis, MA 01253

Well maintained vinyl sided Mobil Home with stick built 12x34 room built onto it. Lot is included in sale. Vinyl sided, full bath, updated flooring, deck for grilling. Two sheds, Furnishings remain. Very private corner lot. Walk to the Clubhouse/pool from this location. Great amenities at Klondike Camp Resort for $150 monthly/ $1800 yearlyCANNOT be used as a primary home. CASH sales only.

Susan Deacon RE/MAX COMPASS

759 N Main Rd, Otis, MA 01253
/36
$6,250,000
- 4 Beds
- 3.5 Baths
- 5,000 Sq Ft
53 Whites Hill Rd, Egremont, MA 01230

Set against a backdrop of sweeping mountain views, this stunning modern residence offers an unparalleled combination of privacy, energy efficiency, and understated refinement. The award-winning home is designed to passive house standards and constructed with an emphasis on durability and sustainability. Natural light streams through high-performance triple-glazed windows and floor to ceiling

Claudia Crane COMPASS MASSACHUSETTS , LLC GB

53 Whites Hill Rd, Egremont, MA 01230
/39
$308,000
- 3 Beds
- 2.5 Baths
- 1,500 Sq Ft
11 Corey Rd, Hancock, MA 01237

Country Village furnished end unit condo with 3 bedrooms, 2.5 baths walkable to pool, slopes, main lodge and country store.Living room has wood burning fireplace with upstairs open seating area/loft overlooking lower level. nice rear deck with distant west views over back meadow. Good storage for skis and outdoor equipment.

Carolyn Umlauf HARSCH ASSOCIATES

11 Corey Rd, 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
/18
$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, additional family room on the lower level and newer appliances. Enjoy the Tennis/pickle ball courts or take swim

Toni Marie Gage SIGNATURE ASSOCIATES

2-5 Rolling Hill Build 2 Unit 5 Ln, Lenox, MA 01240
/37
$159,900
- 3 Beds
- 2 Baths
- 2,491 Sq Ft
155 River Rd, Clarksburg, MA 01247

Charming Farmhouse Fixer-Upper with Endless Potential Discover the charm and possibilities in this classic farmhouse ready for your personal touch! This spacious home features large rooms filled with natural light, original hardwood floors, and timeless character throughout. With a little vision and TLC, it can be transformed into your dream country retreat. Outside, enjoy a beautifully

Michele Purcell Lamacchia Realty, Inc.

155 River Rd, Clarksburg, MA 01247
/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
/46
$399,000
- 4 Beds
- 2 Baths
- 2,015 Sq Ft
149 Fort Hill Ave, Pittsfield, MA 01201

Embrace countryside tranquility in this 4-bedroom, 2-bath home that blends rustic charm with modern amenities. Nestled in serenity, this property is the perfect retreat for those seeking peace without sacrificing convenience.As you step through the front door, the welcoming atmosphere of this country home envelops you. The living spaces are bathed in natural light, highlighting the comfortable

Carrie Wright WILLIAM PITT SOTHEBY'S - LENOX

149 Fort Hill Ave, Pittsfield, MA 01201
/51
$775,000
- 3 Beds
- 3.5 Baths
- 4,160 Sq Ft
2232 Jacobs Ladder Rd, Becket, MA 01223

Experience the perfect blend of nature, sophistication, and comfort in this thoughtfully crafted home and carriage house on 4.25 acres. This property is packed with personality.Enjoy the mature gardens, the fabulous deck for entertaining, the inviting swimming pool, and a wooded path leading to a stone fire pit, one mile from Jacob's Pillow.The photographs will offer a clue as to why you need to

Claudia Crane COMPASS MASSACHUSETTS , LLC GB

2232 Jacobs Ladder Rd, Becket, MA 01223
/39
$440,000
- 2 Beds
- 2 Baths
- 1,683 Sq Ft
5 Windflower Way, Williamstown, MA 01267

Welcome to your dream condo located at 5 Windflower Way. This beautifully updated residence offers a blend of comfort & convenience, making it a perfect place for those seeking low maintenance. The well-equipped kitchen features modern appliances, quartz countertops, a beautiful, tiled floor, & ample cabinets. This condo includes 2 generously sized bedrooms, and two bathrooms. The attached

Jessica Rizzo LAMACCHIA REALTY, INC

5 Windflower Way, Williamstown, MA 01267
/38
$299,000
- 3 Beds
- 2 Baths
- 1,634 Sq Ft
1052 Beaver Pond Meadows, Hancock, MA 01237

Charming 3-Bedroom Country Condo with Scenic ViewsEscape the hustle and embrace the tranquility of country living with this beautifully maintained 3-bedroom, 2-bathroom condo, nestled in a peaceful rural setting. Perfect for families, retirees, or weekend getaways, this home offers a perfect blend of comfort, style, and natural beauty.Spacious Open Floor Plan: Enjoy a sun-filled living and dining

Lisa Mendel BURNHAM GOLD REAL ESTATE, LLC

1052 Beaver Pond Meadows, Hancock, MA 01237
/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
/45
$379,900
- 5 Beds
- 2 Baths
- 2,120 Sq Ft
127 Gamwell Ave, Pittsfield, MA 01201

Owned Solar Panels! Tucked away at the end of a quiet cul-de-sac, this spacious five bedroom, two bathroom home offers 2,020 square feet of living space along with additional space in the basement. As you enter the home, you will notice hardwood floors throughout the main level that features three of the bedrooms, laundry, and one full bathroom. The bright living area flows easily into the dining

Cory Evangelisto NOCHER REALTY

127 Gamwell Ave, Pittsfield, MA 01201
/40
$299,999
- 3 Beds
- 1.5 Baths
- 1,560 Sq Ft
192 Curran Rd, Cheshire, MA 01225

Tucked away on a quiet country road in central Cheshire, this charming 3-bedroom, 1.5-bath home offers peace, privacy, and a connection to nature--yet it's just a short drive to both North and South County amenities. Set on nearly 2 acres bordered by woods and state land, enjoy walking trails, wildflowers, and young pear and apple trees right outside your door. The home is neat and well-kept,

Dennis D'Arcangelo MONARCH REALTY, INC.

192 Curran Rd, Cheshire, MA 01225
/62
$499,000
- 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
/18
$154,000
- 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
/66
$2,250,000
- 5 Beds
- 6 Baths
- 5,477 Sq Ft
1030 West St, Pittsfield, MA 01201

1030 West is a bespoke family compound on 6 acres between Onota Lake and Pittsfield State Forest, offering refined country living with city convenience. The historic main house, decorated by designer Heidi Caillier and featured in her book Memories of Home, has been thoughtfully renovated with timeless materials - custom cabinetry, marble, limestone, Waterworks fixtures, designer and vintage

Tracy Crawford COMPASS MASSACHUSETTS , LLC GB

1030 West St, Pittsfield, MA 01201
/27
$255,000
- 3 Beds
- 1 Bath
- 888 Sq Ft
157 Maple Grove Dr, Pittsfield, MA 01201

Welcome to easy, one-level living in this 3-bedroom ranch, nestled in the sought-after southeast section of Pittsfield. The property features vinyl siding, modern appliances, and on-demand hot water. Outside you will find a fully fenced-in yard ideal for relaxing or entertaining. Enjoy summer days on the expansive deck or take a dip in the above-ground pool. Two storage sheds provide space for

Jessica Rizzo LAMACCHIA REALTY, INC

157 Maple Grove Dr, Pittsfield, MA 01201
/48
$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
/43
$699,000
- 3 Beds
- 2.5 Baths
- 2,135 Sq Ft
770 Summer St Unit 3A, Lee, MA 01238

Welcome home to Lakeside condominiums at Foxhollow! An established condo community perfectly positioned between Lee/Lenox/Stockbridge close to all area attractions! Desirable ground level unit features easy living. Enjoy morning coffee on your spacious deck taking in open rolling lawns and mountain views. Open living/dining with fireplace, updated kitchen w quartz counters, stainless

Pamela Roberts ROBERTS & ASSOC. REALTY, INC

770 Summer St Unit 3A, Lee, MA 01238
/70
$875,000
- 3 Beds
- 2 Baths
- 1,567 Sq Ft
171 Lake Shore Dr, Otis, MA 01253

Welcome to this exceptional 3-bedroom, 2-bathroom lakefront retreat w/an in-ground pool,located in the highly sought-after Otis Woodlands community. Perfectly situated on OWL Lake, this home offers a rare combination of natural beauty, modern upgrades, and an array of resort-style amenities, making it the ideal country escape or full-time residence.Step inside to an open-concept living area with

Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

171 Lake Shore Dr, Otis, MA 01253
/50
$1,825,000
- 5 Beds
- 5.5 Baths
- 3,225 Sq Ft
5 Easland Rd, West Stockbridge, MA 01266

A Home Designed for Living and RetreatNestled at the base of Tom Ball Mountain on over 10 private acres, 5 Easland Road is a custom-designed contemporary sanctuary where nature, luxury, and thoughtful craftsmanship come together in perfect harmony.This 5-bedroom, 5.5-bath home features soaring vaulted ceilings, dramatic walls of glass, and gleaming hardwood floors throughout. Each of the three

Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

5 Easland Rd, West Stockbridge, MA 01266
/55
$5,499,500
- 8 Beds
- 6.5 Baths
- 6,986 Sq Ft
140 Hancock Rd, Pittsfield, MA 01201

Welcome to an extraordinary opportunity on the shores of Pontoosuc Lake. This remarkable estate sets a new standard for lakefront living in Pittsfield and beyond, offering a rare combination of luxury, scale, and setting.With over 18,700 square feet of total space, including an impressive amount of garage space suitable for car collectors or hobbyists, this home provides room to live, relax, and

Cameron Volastro STONE HOUSE PROPERTIES, LLC

140 Hancock Rd, Pittsfield, MA 01201
/48
$620,000
- 3 Beds
- 3 Baths
- 1,680 Sq Ft
770 Summer St Unit 5D, Lee, MA 01238

Welcome to 5D Lakeside at Foxhollow - a beautifully updated 3-bedroom, 3-full-bath condo offering the perfect blend of modern comfort and classic Berkshire charm.Enjoy seasonal views of sparkling Laurel Lake from your enclosed summer porch, the ideal spot for morning coffee or evening gatherings. Inside, you'll find a thoughtfully updated kitchen and baths, a cozy wood-burning fireplace, and

Paula McLean PAULA MCLEAN REALTORS INC.

770 Summer St Unit 5D, Lee, MA 01238
/52
$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
/25
$659,000
- 4 Beds
- 3 Baths
- 2,122 Sq Ft
9201 Mountainside Dr, Hancock, MA 01237

Turnkey ski home at Jiminy Peak—New England’s premier mountain resort under 2.5hrs to NYC & Boston. Steps from the slopes, it offers 2 living rooms, a fireplace for cozy winter evenings, master bedroom with ensuite jacuzzi, deck overlooking forest and mountain, and ample parking. Enjoy heated pools, hot tubs, tennis courts, onsite dining from the Mezze Hospitality Group, the convenience of an

Derek Greene The Greene Realty Group

9201 Mountainside Dr, Hancock, MA 01237
/52
$639,000
- 4 Beds
- 3.5 Baths
- 3,084 Sq Ft
232 Harrington Rd, Otis, MA 01253

There's room for everyone in this four bedroom contemporary cape set on 13+ acres. Designed by the owner for one level living, the lower and upper levels feature full baths, additional bedrooms and a second living area. Highlights of the main level include a private office, screened porch, deck, laundry & attached garage. The main floor living area incorporates a living room with gas fireplace,

Kim Bergland RED HORSE REAL ESTATE, LLC

232 Harrington Rd, Otis, MA 01253
/48
$3,750,000
- 4 Beds
- 4.5 Baths
- 5,300 Sq Ft
116 Brush Hill Rd, Great Barrington, MA 01230

Custom Built Craftsman Contemporary Home nestled in a beautifully landscaped property with an orchard, gardens and path to a seasonal brook. Inside this well appointed home you will find large rooms Vaulted ceilings, whimsical lighting, Fireplaces, Indoor pool, hot tub and sauna, radiant floor & forced air throughout. Two primary suites on main floor and 2/3 more bedrooms in the lower walkout

Mark Rosengren LANCE VERMEULEN RE, INC

116 Brush Hill Rd, Great Barrington, MA 01230
/17
$845,000
- 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
/29
$625,000
- 4 Beds
- 3.5 Baths
- 3,296 Sq Ft
14 Alpine Trail Unit 14, Pittsfield, MA 01201

Welcome to your dream mountain retreat! This stunning end unit in a community of 96 units offers an unparalleled lifestyle for outdoor enthusiasts. With effortless access to ski trails right from your back screened-in porch, you can hit the slopes at Bousquet Mountain anytime you desire.Spanning over 3,200 square feet, this 4-bedroom, 3.5-bath condo has a spacious three-level layout. Step inside

Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

14 Alpine Trail Unit 14, Pittsfield, MA 01201
/54
$939,000
- 5 Beds
- 4.5 Baths
- 3,700 Sq Ft
127 Alpine Trail, Pittsfield, MA 01201

This unit is absolutely stunning! It has breathtaking views of the mountains and spacious open common areas filled with natural light. The main Great room has soaring ceilings, a cozy gas fireplace, wood floors, and direct access to your private screened porch and deck. The kitchen, dining area, and first-floor primary en-suite are all open and inviting. Additionally, there is a main level

Cortney Dupont COHEN & WHITE ASSOCIATES

127 Alpine Trail, Pittsfield, MA 01201
/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
/40
$425,000
- 4 Beds
- 2 Baths
- 1,740 Sq Ft
792 Middle Rd, Clarksburg, MA 01247

Welcome home to this spacious Ranch/Rambler home with 4 bedrooms and two full bathrooms. Vaulted ceiling in the living room. The floor plan conveniently flows well through the kitchen and dining room. The kitchen has a penincela with seating. Off the dining room is a slider out to the large deck that also connects to the swimming pool. The lower level has a bonus/family room with a bar. Two car

Michael Hernandez 360BERKSHIRE REALTY GROUP

792 Middle Rd, Clarksburg, MA 01247
/39
$549,000
- 3 Beds
- 3 Baths
- 1,864 Sq Ft
305 Shadow Ln, Sandisfield, MA 01255

This beautiful 3-bed, 3-bath home in the Otis Wood Lands offers modern comforts in a serene setting. The property boasts a screen porch, sun deck, and 2 wood burning fireplaces! The sunlit great room, with floor-to-ceiling windows, is perfect for entertaining with its open concept living room, dining area, and kitchen. The large primary suite features a wood burning fireplace, walk-in closet, and

Sarah Dixon LANCE VERMEULEN RE, INC

305 Shadow Ln, Sandisfield, MA 01255
/26
$629,000
- 4 Beds
- 2.5 Baths
- 2,340 Sq Ft
54 Egremont Plain Rd, Great Barrington, MA 01230

Great New England farmhouse with really nice views. Common rooms are amply sized and the kitchen great room is perfect for many different activities. Extra room on the first floor can be used as a bedroom or an office (not pictured.) Many extras - structural renovations in 2004, central air, in line generator, in ground pool, screened porch and so much charm. Nice 3.89 acre parcel with detached

Katie Williams STONE HOUSE PROPERTIES, LLC

54 Egremont Plain Rd, Great Barrington, MA 01230
/31
$4,900,000
- 5 Beds
- 6.5 Baths
- 5,890 Sq Ft
390 Tamaridge Rd, Great Barrington, MA 01230

STUNNING LONG VIEWS, RARE 330+ ACRE PARCEL, ABUTS CONSERVATION LAND! Total seclusion and privacy, bucolic countryside with some open meadows and wooded hillside. Once a grand Berkshire estate, the property is comprised of the main Tudor style residence with indoor pool, shingled barn, Dutch colonial multi family dwelling, a guest house & several smaller sheds and workshop. The buildings are all

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

390 Tamaridge Rd, Great Barrington, MA 01230
/53
$3,150,000
- 5 Beds
- 4.5 Baths
- 5,238 Sq Ft
56 Crooked Hill Rd, Great Barrington, MA 01230

Alford Stunner! Exceptionally Designed Turnkey Home with Mountain Views!Completed in 2006, this 5200+ sq ft architect-designed home comes to the market for the first time. Meticulously curated materials, interior designer finishes, and a high-end build culminate in this showpiece home on 19.3 acres, with gunite pool and pool house.Upon entry, this home exudes warmth, style, and comfort - the

Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

56 Crooked Hill Rd, Great Barrington, MA 01230
/19
$799,000
- 3 Beds
- 2 Baths
- 2,000 Sq Ft
5 Aspen Way Unit 17, Pittsfield, MA 01201

Great opportunity to custom design your 2000 square foot free-standing condo home at Berkshire Country Meadows! This is one of only a few remaining sites in this established community. Close to Pontoosuc Lake and centrally located for all Berkshire attractions. Association has a club house with fitness equipment, pool and tennis. Select from several floor plans which feature a contemporary

Pamela Roberts ROBERTS & ASSOC. REALTY, INC

5 Aspen Way Unit 17, Pittsfield, MA 01201

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