158 houses for sale in Tanglewood, Stockbridge town Berkshire County Massachusetts

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Located in Lee MA is a waterfront property a home built in 1880 and renovated in 1994. A bucolic location with views of rushing water and mountains. A perfect home for a variety of birds and established gardens. This 3500 sq. ft home offers an open floor plan that includes living room with fireplace, cooks kitchen with island and dining area. Main level includes a private bedroom and bath; screen porch, deck, laundry room/office, powder room, attached one car garage and office with separate entrance. The second floor offers 2 guest bedroom with private baths and PRIMARY with walk in closet, access to a Juliet deck and private studio space. Free standing single garage located at the rear of the property. This property has multiple uses!

Welcome to 184 Melbourne Road in Pittsfield. This ranch style home boast two generously sized bedrooms, full bath, an open concept living room, kitchen and dining room. This home has been beautifully renovated and maintained throughout the years and it shows. Some of the recent updates include freshly refinished hardwood floors throughout, fresh interior paint, granite countertops, a large island complete with prep sink amongst many others. As you enter the home you are warmly greeted by an abundance of natural light. An attached one car garage adds to the functionality of this move in ready home. It is perfectly placed on approximately 0.59 acres of flat terrain. Don't miss the opportunity to make this your forever home!

Charming and full of character, this in town Lee home blends timeless original details with thoughtful modern updates. Beautiful hardwood floors, original woodwork, and classic architectural features create warmth throughout. The spacious layout offers comfortable living with abundant natural light and inviting spaces for everyday life or entertaining. A Tesla charger adds modern convenience, while the walkable location puts shops, restaurants, and local amenities just moments away. Located in Lee's Commercial Business Corridor (CBC) District, the property also offers added flexibility with a variety of permitted residential and commercial uses, subject to town zoning regulations. A unique opportunity combining historic charm, convenience, and future potential

9-Unit Victorian Investment Property - Prime South County Location This is an exceptional opportunity to own a fully occupied, income-producing Victorian multifamily property set on 2.5 beautifully landscaped acres in a highly desirable South County location. Combining classic charm with strong rental performance, this property is ideal for investors seeking both stability and long-term potential-MLS listing only displays 8 units. Please see rent roll under documents. The building features a total of nine residential units, thoughtfully configured to attract a diverse tenant base. There are two efficiency one-bedroom units, one spacious two-bedroom unit, and six standard one-bedroom units, each offering a comfortable layout with a living room and full kitchen. The property is currently fully occupied, providing immediate and consistent rental income. It has a strong occupancy history and appealing unit mix contribute to long-term tenant retention and investment reliability. The grounds

Discover this breathtaking timber-frame home sited on a peaceful and private 10-acre park-like setting central to the Berkshires. Redesigned by architect Pam Sandler, who added a vaulted great room ceiling, a welcoming front porch, a spacious screened porch, and a 3-car garage. Featuring a first-floor en-suite primary bedroom, a generous living and dining area anchored by a commanding fieldstone fireplace, and a well-planned kitchen with all stainless appliances. Three upstairs bedrooms have ample closet space, and the basement family room with a wood-burning stove offers a cozy winter retreat. This eco-friendly home features a newly built barn, solar panels, and heat-pump climate control. There is so much to experience in this beautifully updated home, just 10 minutes from Tanglewood

Charming and full of character, this in town Lee home blends timeless original details with thoughtful modern updates. Beautiful hardwood floors, original woodwork, and classic architectural features create warmth throughout. The spacious layout offers comfortable living with abundant natural light and inviting spaces for everyday life or entertaining. A Tesla charger adds modern convenience, while the walkable location puts shops, restaurants, and local amenities just moments away. Located in Lee's Commercial Business Corridor (CBC) District, the property also offers added flexibility with a variety of permitted residential and commercial uses, subject to town zoning regulations. A unique opportunity combining historic charm, convenience, and future potential

Renovated 3 bedroom 3 bathrooms, 1875 historic colonial house on two acres, detached garage, big sunroom, deck for entertaining, bubbling brook on property, 5 min to Red Lion Inn/Stockbridge center, 5 min to Lee's Main Street, private, abutting Beartown Mountain Preserve/State Forest, minutes to trails, ski, golf, lakes, restaurants, supermarket, outlets, Tanglewood, Jacobs Pillow, Shakespeare Theatre Company, museums, Housatonic River and more

Just around the corner from world-renowned Tanglewood, this exceptional Richmond property offers a truly prime Berkshires location - where music, culture, and natural beauty meet. Set on just over five picturesque acres with shared ownership in a charming small pond, the setting is as special as the home itself. Beautiful open landscaping creates an inviting approach, with sweeping lawns and thoughtfully maintained grounds that enhance the sense of privacy and serenity. The home itself is bright and airy, filled with natural light and designed for both comfortable everyday living and gracious entertaining. The kitchen is the heart of the home, seamlessly open to a sunny breakfast nook and a sun-filled family room - perfect for gathering with friends and family. A large pantry provides exceptional storage and functionality. For more formal occasions, enjoy a separate dining room, elegant sitting room, and formal living room. A heated sunroom offers year-round enjoyment, while a dedicate

Tucked away on just under an acre of absolute privacy in beautiful Lee MA This modified Cape-style home is a masterclass in character. Over the years, thoughtful renovations have seamlessly blended classic architecture with contemporary living. Step inside to find hardwood floors that guide you into a spectacular living room, where dramatic vaulted ceilings create an airy, sanctuary. Two cozy pellet stoves offer the ultimate in warmth and ambiance during crisp New England autumns. 4 spacious bedrooms and 2 full baths, the layout is as functional as it is inviting. Outside, your private yard oasis awaits-featuring an inground pool wrapped in serene privacy, a spacious two-car garage, and plenty of room to breathe. Don't just buy a house; inherit a lifestyle of Berkshires beauty

Tucked into a convenient Pittsfield location, 9 Donovan Street offers a rare opportunity to own a home that has been lovingly held for 36 years. Featuring 3 bedrooms and 2 bathrooms, including a desirable primary en suite, this property offers a functional layout with comfortable living spaces filled with natural light. Step outside to enjoy the back deck overlooking the yard, perfect for relaxing or entertaining, along with the ease of a paved driveway. While the home reflects a more classic style, the bones are fantastic and provide the perfect canvas for a buyer to update and make it their own. Ideally situated near local amenities, shopping, dining, and just a short drive to the NY State line, this home blends everyday convenience with regional accessibility

Thoughtfully crafted custom home offering timeless New England character, quality craftmanship, and beautiful eastern mountain views. Rich natural woodwork and exposed beams create a warm, inviting atmosphere throughout. The custom kitchen with granite, marble and butcher block countertops opens to the dining area with French doors leading to a screened in sunroom. Enjoy the expansive deck, stone patio with firepit, and beautifully landscaped grounds. Spacious living and family rooms with woodburning fireplace and generous mudroom/office. Offering three bedrooms, three baths, plus a versatile creative space, studio/sitting room, endless possibilities. Minutes to downtown Lee, Stockbridge, Lenox, Tanglewood, shopping, dining and all that the Berkshires has to offer for year-round living

IMMACULATE 3 BEDROOM COLONIAL with IN LAW APARTMENT in SOUTH LEE on a quiet cul de sac. Zoned 2 family, Partially fenced back yard, attached garage and central air conditioning. Great investment or family home

Great price for this charming three bedroom, one full bath single level home with detached garage and outbuilding. Many improvements made over the years, including vinyl windows, connection to town sewer, electrical service and breaker box, well, galvanized oil tank and furnace. Some TLC needed but a great starter home with amazing potential. Conveniently located just minutes to the center of Lee, Prime Outlets, and Turnpike. Please note that Cape Street is also Route 20 and the MASS Pike is nearby so you will hear traffic noise. Quaint and comfortable. a must see!

Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes -one a four bedroom home and a 1000 sq ft guest house-both surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming 1BR guest cottage, with large living room and mini-splits, is ideal for rental income or private guests. Spacious garage allows room for cars, hobbies and workshop, perfect pool site, and privacy ensured by abutting protected land. Generator for both houses.Access to town beach

Renovated 3 bedroom 3 bathrooms, 1875 historic colonial house on two acres, detached garage, big sunroom, deck for entertaining, bubbling brook on property, 5 min to Red Lion Inn/Stockbridge center, 5 min to Lee's Main Street, private, abutting Beartown Mountain Preserve/State Forest, minutes to trails, ski, golf, lakes, restaurants, supermarket, outlets, Tanglewood, Jacobs Pillow, Shakespeare Theatre Company, museums, Housatonic River and more

Welcome to 184 Melbourne Road in Pittsfield. This ranch style home boast two generously sized bedrooms, full bath, an open concept living room, kitchen and dining room. This home has been beautifully renovated and maintained throughout the years and it shows. Some of the recent updates include freshly refinished hardwood floors throughout, fresh interior paint, granite countertops, a large island complete with prep sink amongst many others. As you enter the home you are warmly greeted by an abundance of natural light. An attached one car garage adds to the functionality of this move in ready home. It is perfectly placed on approximately 0.59 acres of flat terrain. Don't miss the opportunity to make this your forever home!

Thoughtfully crafted custom home offering timeless New England character, quality craftmanship, and beautiful eastern mountain views. Rich natural woodwork and exposed beams create a warm, inviting atmosphere throughout. The custom kitchen with granite, marble and butcher block countertops opens to the dining area with French doors leading to a screened in sunroom. Enjoy the expansive deck, stone patio with firepit, and beautifully landscaped grounds. Spacious living and family rooms with woodburning fireplace and generous mudroom/office. Offering three bedrooms, three baths, plus a versatile creative space, studio/sitting room, endless possibilities. Minutes to downtown Lee, Stockbridge, Lenox, Tanglewood, shopping, dining and all that the Berkshires has to offer for year-round living

Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes -one a four bedroom home and a 1000 sq ft guest house-both surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming 1BR guest cottage, with large living room and mini-splits, is ideal for rental income or private guests. Spacious garage allows room for cars, hobbies and workshop, perfect pool site, and privacy ensured by abutting protected land. Generator for both houses.Access to town beach

Located in Lee MA is a waterfront property a home built in 1880 and renovated in 1994. A bucolic location with views of rushing water and mountains. A perfect home for a variety of birds and established gardens. This 3500 sq. ft home offers an open floor plan that includes living room with fireplace, cooks kitchen with island and dining area. Main level includes a private bedroom and bath; screen porch, deck, laundry room/office, powder room, attached one car garage and office with separate entrance. The second floor offers 2 guest bedroom with private baths and PRIMARY with walk in closet, access to a Juliet deck and private studio space. Free standing single garage located at the rear of the property. This property has multiple uses!

Renovated 3 bedroom 3 bathrooms, 1875 historic colonial house on two acres, detached garage, big sunroom, deck for entertaining, bubbling brook on property, 5 min to Red Lion Inn/Stockbridge center, 5 min to Lee's Main Street, private, abutting Beartown Mountain Preserve/State Forest, minutes to trails, ski, golf, lakes, restaurants, supermarket, outlets, Tanglewood, Jacobs Pillow, Shakespeare Theatre Company, museums, Housatonic River and more

Charming and full of character, this in town Lee home blends timeless original details with thoughtful modern updates. Beautiful hardwood floors, original woodwork, and classic architectural features create warmth throughout. The spacious layout offers comfortable living with abundant natural light and inviting spaces for everyday life or entertaining. A Tesla charger adds modern convenience, while the walkable location puts shops, restaurants, and local amenities just moments away. Located in Lee's Commercial Business Corridor (CBC) District, the property also offers added flexibility with a variety of permitted residential and commercial uses, subject to town zoning regulations. A unique opportunity combining historic charm, convenience, and future potential

Tucked into a convenient Pittsfield location, 9 Donovan Street offers a rare opportunity to own a home that has been lovingly held for 36 years. Featuring 3 bedrooms and 2 bathrooms, including a desirable primary en suite, this property offers a functional layout with comfortable living spaces filled with natural light. Step outside to enjoy the back deck overlooking the yard, perfect for relaxing or entertaining, along with the ease of a paved driveway. While the home reflects a more classic style, the bones are fantastic and provide the perfect canvas for a buyer to update and make it their own. Ideally situated near local amenities, shopping, dining, and just a short drive to the NY State line, this home blends everyday convenience with regional accessibility

IMMACULATE 3 BEDROOM COLONIAL with IN LAW APARTMENT in SOUTH LEE on a quiet cul de sac. Zoned 2 family, Partially fenced back yard, attached garage and central air conditioning. Great investment or family home

Just around the corner from world-renowned Tanglewood, this exceptional Richmond property offers a truly prime Berkshires location - where music, culture, and natural beauty meet. Set on just over five picturesque acres with shared ownership in a charming small pond, the setting is as special as the home itself. Beautiful open landscaping creates an inviting approach, with sweeping lawns and thoughtfully maintained grounds that enhance the sense of privacy and serenity. The home itself is bright and airy, filled with natural light and designed for both comfortable everyday living and gracious entertaining. The kitchen is the heart of the home, seamlessly open to a sunny breakfast nook and a sun-filled family room - perfect for gathering with friends and family. A large pantry provides exceptional storage and functionality. For more formal occasions, enjoy a separate dining room, elegant sitting room, and formal living room. A heated sunroom offers year-round enjoyment, while a dedicate