175 properties for sale in Berkshire Heights, Great Barrington town Berkshire County Massachusetts

Imagine waking up in a sun-splashed home just steps from Great Barrington's lively Main Street-where every cafe, bookstore, and gallery feels like an extension of your neighborhood. This second-floor floor-through condo is more than a home; it's a canvas for your life. Over 1,800 sq. ft. of expansive living space unfolds with towering ceilings, oversized windows, and graceful arched doorways that evoke another era. Every detail-from the textured walls to the light pouring in at all hours-creates a sense of romance and possibility. The home is thoughtfully divided: one wing offers a spacious bedroom and lounge with guest alcove, while the other wing hosts a dining area, kitchen, and charming nook for work or rest. A central hall with clawfoot tub bath and laundry ties the spaces together, blending beauty with everyday comfort. Here, you are at the center of it allBroadway-quality theater, world-class dining, outdoor adventuresall just beyond your front door. Own a piece of Great Barring

Situated on Great Barrington's highly sought after neighborhood of 'The Hill', 11 Prospect delivers on style, convenience and of course, location! This four bedroom home with two and a half baths over three floors and hardwood floors throughout, offers lots of room for family and friends. An oversized screened in porch, attached two car garage and a finished basement are just some of the 'must haves' to enjoy in this recently updated property. Steps away from the shoreline of Lake Mansfield and a simple stroll to downtown Great Barrington's many coffee shops, restaurants, bakeries and theaters, this property is the perfect move in ready home!

Rare offering of over six acres 'On the Hill', sprawling residence with first floor primary, large eat-in kitchen with cozy fireplace. porch-privacy-garage. open acreage bordered by woods. walking distance to Main Street, Skiing and Lake Mansfield nearby. Five bedrooms, three baths. Formal living room. Plenty of room for expansion

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 integrating the surroundings of the natural world. This luxurious three-story residential enclave comprises 30 condominium units, including 13 one-bedroom and 17 two-bedroom residences. The units offer breathtaking mountain-views with private balconies or secluded terraces, providing optimal space for both entertainment and tranquil relaxation

Luxurious, fully-modernized 1850s Victorian in the heart of Great Barrington. Elegant, four-story 3600 sq. ft. newly renovated clapboard and shingle house with covered porch. Meticulous renovation features chef's kitchen, four+ bedrooms, 4.5 bath, second floor and basement laundry, walk-out finished basement with private entrance and bathroom, perfect for guest suite or professional office. High-end appliances, including 6-burner Wolf stove and Bosch French door refrigerator with two freezer drawers, Bosch dishwasher, wine cooler and microwave in the island. Full-size prep sink in the kitchen island, 36' farmhouse sink in the main counter. Cabinets are all-wood with soft-close drawers and doors; vented whole-house A/C and heat pump with propane back-up; primary bath with heated floor gas grill. EV charging station in driveway. Walking distance to Lake Mansfield and Main Street shops, restaurants and theaters. House can be sold furnished

Prime Downtown Great Barrington Gem - Endless Possibilities! Welcome to 406 Main Street, a rare opportunity in the heart of downtown Great Barrington, MA. Just steps from bustling Main Street shops and restaurants, this versatile 5,180 sq ft building offers exceptional potential for residential, commercial, or creative mixed-use transformation. Zoned B2, the property allows for single-family, multi-unit, or live/work conversion-with no sprinkler system required for up to 3 residential units. Already equipped with 1 full bath and 4 powder rooms, and featuring two finished floors, the layout adapts effortlessly to your vision-be it modern apartments, stylish offices, retail space, or a dynamic studio. - Spacious and bright with 5,180 sq ft across two levels - Excellent bone

Enjoy the best of Great Barrington from this beautifully updated ground-level condominium in On the Hill. Offering easy one-level living, this inviting home features an updated kitchen with abundant storage, new appliances, and bar seating, plus a spacious dining area perfect for gathering with family and friends. The sunken living room boasts a wood-burning fireplace and opens to a private patio for relaxing outdoors. The primary suite includes a walk-in closet and ensuite bath, while the second bedroom enjoys its own full bath. Complete with in-unit laundry, a private garage stall, community pool, and beautifully maintained grounds, this is Berkshire living at its best

Timeless Craftsmanship Meets Modern Living-Built in 2004, this exquisitely crafted historic reproduction home seamlessly blends old-world charm with contemporary comfort. Set on 1.82 acres with sweeping mountain views, this 3-bedroom, 2.5-bathroom home features meticulous hand-crafted details throughout-honoring traditional design while offering the conveniences of modern construction. The welcoming gourmet eat-in kitchen is perfect for everyday living and entertaining. Step out to the inviting covered porch-an ideal spot to savor morning coffee and evening sunsets with mountain vistas. The primary suite captures stunning views, while the expansive yard provides additional room to roam. 2-car oversized garage. Secluded setting just minutes to downtown Great Barrington and Berkshire attractions

Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless interaction during meals and gatherings. The living area extends outward to two distinct private spaces: a screened-in porch for three-season relaxation and a separate private deck. Designed for convenience and longevity, the first floor features a primary bedroom suite complete with a spacious en-suite bathroom and laundry

Enjoy the best of Great Barrington from this beautifully updated ground-level condominium in On the Hill. Offering easy one-level living, this inviting home features an updated kitchen with abundant storage, new appliances, and bar seating, plus a spacious dining area perfect for gathering with family and friends. The sunken living room boasts a wood-burning fireplace and opens to a private patio for relaxing outdoors. The primary suite includes a walk-in closet and ensuite bath, while the second bedroom enjoys its own full bath. Complete with in-unit laundry, a private garage stall, community pool, and beautifully maintained grounds, this is Berkshire living at its best

Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless interaction during meals and gatherings. The living area extends outward to two distinct private spaces: a screened-in porch for three-season relaxation and a separate private deck. Designed for convenience and longevity, the first floor features a primary bedroom suite complete with a spacious en-suite bathroom and laundry

Imagine waking up in a sun-splashed home just steps from Great Barrington's lively Main Street-where every cafe, bookstore, and gallery feels like an extension of your neighborhood. This second-floor floor-through condo is more than a home; it's a canvas for your life. Over 1,800 sq. ft. of expansive living space unfolds with towering ceilings, oversized windows, and graceful arched doorways that evoke another era. Every detail-from the textured walls to the light pouring in at all hours-creates a sense of romance and possibility. The home is thoughtfully divided: one wing offers a spacious bedroom and lounge with guest alcove, while the other wing hosts a dining area, kitchen, and charming nook for work or rest. A central hall with clawfoot tub bath and laundry ties the spaces together, blending beauty with everyday comfort. Here, you are at the center of it allBroadway-quality theater, world-class dining, outdoor adventuresall just beyond your front door. Own a piece of Great Barring

Luxurious, fully-modernized 1850s Victorian in the heart of Great Barrington. Elegant, four-story 3600 sq. ft. newly renovated clapboard and shingle house with covered porch. Meticulous renovation features chef's kitchen, four+ bedrooms, 4.5 bath, second floor and basement laundry, walk-out finished basement with private entrance and bathroom, perfect for guest suite or professional office. High-end appliances, including 6-burner Wolf stove and Bosch French door refrigerator with two freezer drawers, Bosch dishwasher, wine cooler and microwave in the island. Full-size prep sink in the kitchen island, 36' farmhouse sink in the main counter. Cabinets are all-wood with soft-close drawers and doors; vented whole-house A/C and heat pump with propane back-up; primary bath with heated floor gas grill. EV charging station in driveway. Walking distance to Lake Mansfield and Main Street shops, restaurants and theaters. House can be sold furnished

Rare offering of over six acres 'On the Hill', sprawling residence with first floor primary, large eat-in kitchen with cozy fireplace. porch-privacy-garage. open acreage bordered by woods. walking distance to Main Street, Skiing and Lake Mansfield nearby. Five bedrooms, three baths. Formal living room. Plenty of room for expansion

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 integrating the surroundings of the natural world. This luxurious three-story residential enclave comprises 30 condominium units, including 13 one-bedroom and 17 two-bedroom residences. The units offer breathtaking mountain-views with private balconies or secluded terraces, providing optimal space for both entertainment and tranquil relaxation

Timeless Craftsmanship Meets Modern Living-Built in 2004, this exquisitely crafted historic reproduction home seamlessly blends old-world charm with contemporary comfort. Set on 1.82 acres with sweeping mountain views, this 3-bedroom, 2.5-bathroom home features meticulous hand-crafted details throughout-honoring traditional design while offering the conveniences of modern construction. The welcoming gourmet eat-in kitchen is perfect for everyday living and entertaining. Step out to the inviting covered porch-an ideal spot to savor morning coffee and evening sunsets with mountain vistas. The primary suite captures stunning views, while the expansive yard provides additional room to roam. 2-car oversized garage. Secluded setting just minutes to downtown Great Barrington and Berkshire attractions

Situated on Great Barrington's highly sought after neighborhood of 'The Hill', 11 Prospect delivers on style, convenience and of course, location! This four bedroom home with two and a half baths over three floors and hardwood floors throughout, offers lots of room for family and friends. An oversized screened in porch, attached two car garage and a finished basement are just some of the 'must haves' to enjoy in this recently updated property. Steps away from the shoreline of Lake Mansfield and a simple stroll to downtown Great Barrington's many coffee shops, restaurants, bakeries and theaters, this property is the perfect move in ready home!

FOR SALE: Prime Downtown Great Barrington Gem - Endless Possibilities! Welcome to 406 Main Street, a rare opportunity in the heart of downtown Great Barrington, MA. Just steps from bustling Main Street shops and restaurants, this versatile 5,180 sq ft building offers exceptional potential for residential, commercial, or creative mixed-use transformation. Zoned B2, the property allows for single-family, multi-unit, or live/work conversion-with no sprinkler system required for up to 3 residential units. Already equipped with 1 full bath and 4 powder rooms, and featuring two finished floors, the layout adapts effortlessly to your vision-be it modern apartments, stylish offices, retail space, or a dynamic studio. - Spacious and bright with 5,180 sq ft across two levels - Excellent bone

Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless interaction during meals and gatherings. The living area extends outward to two distinct private spaces: a screened-in porch for three-season relaxation & separate private deck. Designed for convenience and longevity, the first floor features a primary bedroom suite complete with a spacious en-suite bathroom and laundry

Imagine waking up in a sun-splashed home just steps from Great Barrington's lively Main Street—where every café, bookstore, and gallery feels like an extension of your neighborhood. This second-floor floor-through condo is more than a home; it's a canvas for your life. Over 1,800 sq. ft. Of expansive living space unfolds with towering ceilings, oversized windows, and graceful arched doorways that evoke another era. Every detail—from the textured walls to the light pouring in at all hours—creates a sense of romance and possibility. The home is thoughtfully divided: one wing offers a spacious bedroom and lounge with guest alcove, while the other wing hosts a dining area, kitchen, and charming nook for work or rest. A central hall with clawfoot tub bath and laundry ties the spaces together, blending beauty with everyday comfort. Here, you are at the center of it all: Broadway-quality theater, world-class dining, outdoor adventures, all just beyond your front door. Own a piece of Great Bar

Timeless Craftsmanship Meets Modern Living-Built in 2004, this exquisitely crafted historic reproduction home seamlessly blends old-world charm with contemporary comfort. Set on 1.82 acres with sweeping mountain views, this 3-bedroom, 2.5-bathroom home features meticulous hand-crafted details throughout-honoring traditional design while offering the conveniences of modern construction. The welcoming gourmet eat-in kitchen is perfect for everyday living & entertaining. Step out to the inviting covered porch-an ideal spot to savor morning coffee & evening sunsets with mountain vistas. The primary suite captures stunning views, while the expansive yard provides additional room to roam. 2-car oversized garage. Secluded setting just minutes to downtown Great Barrington & Berkshire attractions

WHISPERING PINES. This tranquil property will call to you as you wind your way through the tall pine-lined driveway. It is a very private setting and just minutes to Butternut, town, and everything else the Berkshires have to offer. Beautiful mature gardens, Gunite Pool, screen porch, and 3600 sq ft of living space to dwell. This 4 bedroom home has 2-Primary en-suite, a large den over the 2-car attached garage. First floor office space or overflow room for guests. A newer first floor Primary Suite wing added in 2017 boasts a very large walk-in closet, steam shower and an ample-sized bedroom. The expansive screen porch looks out on the yard, pool, yard and gardens. Partially finished will easily help you expand upon this magnificent home. A second 2-car garage for enhanced storage space. equipment, or that vintage car you've always wanted the space for. Come see, you'll be pleased you did

Stunning contemporary nestled in tranquility. The main level boasts a gracious great room with cathedral ceilings, fireplace and walls of windows that wash the common spaces with natural light and bring nature in. Gourmet chefs kitchen with ample storage and dining room with direct access to the oversized porch that features a gas stove for the chillier days. First floor primary en suite with walk in closet, direct access to your deck and primary bath with beautiful textures throughout. The second level has three guest bedrooms and two full baths. Lower level features a large family room walkout, additional guest bedroom and full bath. Two car oversized garage with studio space above that gives flexibility in its use. Private setting with expansive lawn and professionally maintained gardens. Great location within a comfortable distance to the Berkshires cultural attractions. Truly a special property both inside and out!

An 1825 colonial has much of its original charm and features in place - wide plank floors, beamed ceiling, original hardware and fully renovated kitchen. Many new appliances, new windows, and foam insulation in the basement. The well insulated attic and walls along with a high efficiency furnace gives you modern comfort. The house is a legal two family. The Studio apartment is attached and could be a private primary 1st floor suite. The current owner has solid Air BnB income from it as is, or it could be rented year-round. The fully insulated barn/garage has it's own 100-amp service and is currently being used as a woodworking shop. A wood stove and a large loft for storage adds to its utility

An 1825 colonial has much of its original charm and features in place - wide plank floors, beamed ceiling, original hardware and fully renovated kitchen. Many new appliances, new windows, and foam insulation in the basement. The well insulated attic and walls along with a high efficiency furnace gives you modern comfort. The house is a legal two family. The Studio apartment is attached and could be a private primary 1st floor suite. The current owner has solid Air BnB income from it as is, or it could be rented year-round. The fully insulated barn/garage has it's own 100-amp service and is currently being used as a woodworking shop. A wood stove and a large loft for storage adds to its utility