209 properties for sale in Larrywaug

Steeped in the timeless elegance of historic Stockbridge, this exceptional Colonial captures the enduring charm of a bygone era, evoking the quintessential New England scenes made famous by Norman Rockwell. Beautifully sited just moments from the heart of town, this distinguished four-bedroom residence blends classic architectural details with gracious, comfortable living. Inside, three fireplaces anchor inviting gathering spaces filled with warmth and character, while three spacious ensuite bedrooms offer exceptional comfort and privacy. Rich period details, handsome proportions, and abundant natural light create a home that is both sophisticated and welcoming. Beyond the main residence, a separate guest cottage provides the perfect retreat for visitors, extended family, a home office, or creative studio. The expansive, level lawn presents a rare opportunity to create a private estate setting with ample room for a pool, tennis court, or beautifully landscaped gardens. Completing the p

HOME BEING SOLD AS IS NO NEGOTIATION ON INSPECTION ISSUES. THE PRICE IS NOT NEGOTIABLE. Two family minutes from downtown Lenox. First floor unit has 2 bedrooms with spacious living area and kitchen. Upstairs unit is a 1 bedroom, 1 bath with fireplace and back deck. Roof replaced in 2021, natural gas, town water and sewer

Nestled in the heart of West Stockbridge, this stunning 5-bedroom, 5.5-bath Federal/Greek Revival style home at 4 Stockbridge Road combines historic charm with modern luxury. Built in 1825, the residence has been beautifully renovated, maintaining its classic character while offering contemporary amenities. The spacious interior features generous living areas, perfect for family gatherings and entertaining. Outside, you'll find a large barn, a greenhouse and impeccable gardens ideal for gardening enthusiasts or creative projects. This property is not just a home; it's an opportunity to enjoy the tranquil beauty of West Stockbridge, with its vibrant community and picturesque surroundings. Located minutes from many local attractions including Tanglewood and minutes from the highway

Offered for the first time in 40 years, this White Pines condo is a rare opportunity to own a residence within one of Stockbridge's most storied properties. Rich with musical history, both White Pines and this particular residence have fascinating ties to local and international music scenes. Filled with natural light, this gracious two-bedroom, two-bath condominium offers generous living spaces and an inviting, easy flow. The beautiful great room is the heart of the home, with two distinct sitting areas and a dedicated dining space-ideal for both relaxed everyday living and entertaining. A large primary suite provides a private retreat, while the second bedroom and full bath offer flexible space for guests or creative pursuits. Set moments from Tanglewood and with exceptional access to Stockbridge Bowl, White Pines captures so much of what makes life in the Berkshires special. Residents enjoy a private beach on the Bowl with dedicated kayak storage, along with an indoor swimming pool

This well-maintained mixed-use property offers excellent flexibility for both commercial and residential use. The building is currently configured as two separate units. The first floor features a bright commercial space with large front-facing windows that provide excellent visibility and natural light-ideal for office or retail use. The space includes a private bathroom, dedicated heating and air conditioning, and a water filtration system for added convenience. The second floor offers a comfortable three-bedroom residential unit with a full bathroom, an open-concept kitchen and dining area, and attractive wood flooring throughout. The property is equipped with two separate heating systems to efficiently serve each unit. Additional highlights include ample parking in front and back

A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90+/- acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams and Warren in an Elizabethan/Jacobean Revival style. The original mansion remains at the heart of the property, surrounded by broad lawns and a collection of buildings added during its later evolution into an educational campus. Despite decades of institutional use, much of the character of the original country house remains. Handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom recall Overlee's Gilded Age origins. Most recently used for classrooms and administrative functions, the mansion was originally designed as a residence, with bedrooms on its upper floors, creating an intriguing foundation for its return to residential use. Beyond the main house, the campus includes two dormitory residences with appro

A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90+/- acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams and Warren in an Elizabethan/Jacobean Revival style. The original mansion remains at the heart of the property, surrounded by broad lawns and a collection of buildings added during its later evolution into an educational campus. Despite decades of institutional use, much of the character of the original country house remains. Handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom recall Overlee's Gilded Age origins. Most recently used for classrooms and administrative functions, the mansion was originally designed as a residence, with bedrooms on its upper floors, creating an intriguing foundation for its return to residential use. Beyond the main house, the campus includes two dormitory residences with appro

Beautifully sited to capture light and long-range views, this architect-designed residence offers timeless elegance within a serene natural setting. Bright, sophisticated interiors open seamlessly to a screened porch and stone terraces overlooking the pool and manicured grounds. Generous proportions and refined architectural details define the living spaces, complemented by a beautifully reimagined library/office, dining, living media/den and kitchen. First-floor primary suite serves as a private retreat, while additional en-suite bedrooms provide comfort and discretion for guests. An upper-level loft (w/ elevator)offers space for gym, studio, or media. A rare offering of privacy, design, and distinction in the Berkshires

This well-maintained mixed-use property offers excellent flexibility for both commercial and residential use. The building is currently configured as two separate units. The first floor features a bright commercial space with large front-facing windows that provide excellent visibility and natural light-ideal for office or retail use. The space includes a private bathroom, dedicated heating and air conditioning, and a water filtration system for added convenience. The second floor offers a comfortable three-bedroom residential unit with a full bathroom, an open-concept kitchen and dining area, and attractive wood flooring throughout. The property is equipped with two separate heating systems to efficiently serve each unit. Additional highlights include ample parking in front and back

This home is the perfect chance to live in a sweet neighborhood with a short stroll to the village. With solid bones, a welcoming front porch, and a detached garage ideal for work shop/studio/storage. Located in a convenient setting, it's ready for your vision, with opportunities for modern updates. A little work could mean a big reward. Housatonic Village a few steps away. Lovely back yard! Being sold as-is

Introducing a beautiful in-town 4-family investment opportunity on the picturesque Main St, offering separate utilities for each unit. With a new roof, fresh paint, and renovations completed in units, 1,2 and3 all in 2023.Can also be purchased as part of a investment portfolio 13 Park Street Stockbridge, MA MLS#249532

Rare, renovated Berkshire investment compound on 0.59 acres in walkable Housatonic. This turnkey property features two separate legal duplexes (4 units total) offering stellar cash flow. The front home (392 Park St) features a 5BR/2BA unit, a sleek 2BR flat, and a prominent street-front walk-out lower level with incredible commercial/addition potential. The rear Swiss-Gothic home (394 Park St) hosts two updated 2BR units. Enjoy a sprawling backyard with mountain views, a community garden, and fruit-bearing trees. Fully insulated and optimized for easy management with 4 separate heating/electric systems, town sewer/water, and off-street parking for 10+ cars. Walk to Berkshire Mountain Bakery; minutes to Great Barrington and Tanglewood. A rare, turnkey find!

Motivated sellers are ready to move! Built in 2019 on 1.73 private acres in Housatonic, this well-maintained 3-bedroom, 3-bath ranch offers approximately 2,915 sq. ft. of finished space. The main level features a primary suite with walk-in closet and private bath, laundry, and red oak flooring milled from trees harvested on the property. The finished walkout lower level offers a large recreation room, full bath, and additional rooms for guests, hobbies, an office, or entertaining. Enjoy a Trex deck, covered patio, above-ground pool, and wooded surroundings. This detached condominium includes exclusive use of the home, yard, pool, deck, driveway, sheds, and grounds-offering single-family privacy. Annual property taxes are approximately $8,164; buyers should verify with the municipality

Set well back from a quiet road beneath mature trees, this one-owner West Stockbridge home offers an immediate sense of privacy, with gardens, lawn and woods gathered around it. Peaceful without feeling isolated, the house has the easy spirit of a modern farmhouse and a relaxed connection to its Berkshire setting.Inside, generous windows bring the landscape into nearly every room. Sunlight moves across bamboo floors, radiant heat adds warmth underfoot, and long sightlines connect the living, dining and kitchen spaces while allowing each to retain its own character. The kitchen sits naturally at the center of daily life with generous workspace and garden views.A light-filled sunroom is a standout, with a cathedral ceiling, exposed beams and windows on three sides overlooking the surrounding greenery. The inviting front porch and rear deck create additional places to sit, dine and enjoy the changing seasons.Upstairs, a broad landing anchors the second floor. The primary bedroom includes

Contemporary home built in 2012 on over 11 acres walking distance to Stockbridge center. Original house was taken down and this sun-drenched home was built on the saved footprint. Main floor has a small living area off the entry open to large kitchen and dining with sliders to the deck, primary suite with walk-in closet and deck access, 1/2 bath and access to the oversized garage. Second floor has vaulted ceilings, a large landing, second living area, 2 guest rooms with a hall bath and another primary suite. There are two porches off the second floor, one small off the primary and the other flanking the East side - covered for protected enjoyment. The Konakpot Brook winds through the back of the 11+ acres giving access to fishing and just relaxing by the water

Experience elevated wellness living in this exceptional Canyon Ranch penthouse in Lenox. This 3,300+ sq. ft. residence offers three spacious ensuite bedrooms, a powder room, an expansive great room, a chef's kitchen and three fireplaces that create a warm, inviting atmosphere. A private patio provides the perfect retreat to relax and enjoy the natural beauty of the Berkshires. Ownership includes a requisite annual resort membership with full access to Canyon Ranch's world-renowned wellness amenities. Just minutes from the Berkshires' acclaimed cultural attractions, fine dining and outdoor recreation, this is a rare opportunity to enjoy luxury, wellness and timeless design in one extraordinary home

Steeped in the timeless elegance of historic Stockbridge, this exceptional Colonial captures the enduring charm of a bygone era, evoking the quintessential New England scenes made famous by Norman Rockwell. Beautifully sited just moments from the heart of town, this distinguished four-bedroom residence blends classic architectural details with gracious, comfortable living. Inside, three fireplaces anchor inviting gathering spaces filled with warmth and character, while three spacious ensuite bedrooms offer exceptional comfort and privacy. Rich period details, handsome proportions, and abundant natural light create a home that is both sophisticated and welcoming. Beyond the main residence, a separate guest cottage provides the perfect retreat for visitors, extended family, a home office, or creative studio. The expansive, level lawn presents a rare opportunity to create a private estate setting with ample room for a pool, tennis court, or beautifully landscaped gardens. Completing the p

A UNIQUE NEW HOME UNDER CONSTRUCTION IN THE HEART OF STOCKBRIDGE, MASSACHUSETTS Historic Living: In an era of increasingly homogenized architecture, this extraordinary timber frame Dutch house replica offers something rare: a true sense of place. Rooted in the early traditions of the surrounding Housatonic Valley, the home is a thoughtful homage to the region's European heritage-crafted with authenticity, integrity, and many locally sourced materials designed to age gracefully. Inspired by early 18th-century Dutch design, the residence features massive anchor beam construction, a steeply pitched roof, thick plank floors and richly textured materials that develop warmth and patina over time. Traditional casement windows with deep sills, exposed timber framing, and masonry fireplaces evoke a timeless aesthetic while integrating seamlessly with the surrounding Berkshire landscape. Behind its historic character lie modern mechanical systems-where exceptional craftsmanship meets innovative

A significant price reduction has just been made on this terrific revenue opportunity property in Stockbridge. The historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. THIS PROPERTY HAS AN EXCELLENT HISTORY OF RENTAL INCOME. The 'Ice House' features its own kitchen and bath, for family gatherings or as Artist Studio. A sparkling in-ground pool for your summer pleasure. All this and more exists close to Main Street Stockbridge, Norman Rockwell Museum, Tanglewood, and all the most important cultural amenities. Rental income' This property has a very nice history of rental income! Who could ask for anything more' Call for a showing today

Beach days, porch evenings and Tanglewood concerts make this the perfect three-season Berkshire cottage. Vaulted ceilings and a fieldstone fireplace anchor the living room, while two bedrooms and a versatile loft provide comfortable space for family and friends. The screened in-porch extends the living space for long summer afternoons and evenings, while the dining room is filled with windows that bring nature inside. Set in the welcoming community of Mahkeenac Heights, this cottage is just a short walk to the town beach at Stockbridge Bowl and close to the Berkshires' many cultural attractions. A wonderful retreat for enjoying all the Berkshires have to offer!

Location, location, location! Ideally situated within easy walking distance of the village, elementary school, and Tanglewood, this charming ranch offers comfortable single-level living in a quiet, desirable neighborhood. The large, level and semi-private backyard provides plenty of room to relax, entertain, garden, or enjoy the above-ground pool. Inside, the home features a spacious open living area currently used as a dining and family room, separate living room, eat-in kitchen, three bedrooms, and a full bath with tub. Step directly from the kitchen onto the deck overlooking the pool and expansive backyard. Additional highlights include an attached two-car garage, full basement with four versatile rooms, and a designated laundry space complete with a laundry chute!

Location, location, location! Ideally situated within easy walking distance of the village, elementary school, and Tanglewood, this charming ranch offers comfortable single-level living in a quiet, desirable neighborhood. The large, level and semi-private backyard provides plenty of room to relax, entertain, garden, or enjoy the above-ground pool. Inside, the home features a spacious open living area currently used as a dining and family room, separate living room, eat-in kitchen, three bedrooms, and a full bath with tub. Step directly from the kitchen onto the deck overlooking the pool and expansive backyard. Additional highlights include an attached two-car garage, full basement with four versatile rooms, and a designated laundry space complete with a laundry chute!

Nestled in the heart of West Stockbridge, this stunning 5-bedroom, 5.5-bath Federal/Greek Revival style home at 4 Stockbridge Road combines historic charm with modern luxury. Built in 1825, the residence has been beautifully renovated, maintaining its classic character while offering contemporary amenities. The spacious interior features generous living areas, perfect for family gatherings and entertaining. Outside, you'll find a large barn, a greenhouse and impeccable gardens ideal for gardening enthusiasts or creative projects. This property is not just a home; it's an opportunity to enjoy the tranquil beauty of West Stockbridge, with its vibrant community and picturesque surroundings. Located minutes from many local attractions including Tanglewood and minutes from the highway

With 22+ acres of residential/agricultural zoned land, open fields, wooded borders, and a lovely little pond, the simplistic, quiet, natural beauty of this Richmond property evokes feelings of peace and tranquility. The property features a 1950's ranch style home with 3 bedrooms, 1-1/2 baths, recently refinished hardwood floors, attached 2-car garage, full basement, additional oversized 2-car garage, plus a beautiful old garage/barn. Situated at a slightly higher elevation the views from this East facing home are quite picturesque overlooking our beautiful Berkshire mountains. This parcel is made up of 3 adjoining lots. A portion of the property to the north abuts Conservation Land. BY APPOINTMENT ONLY. PLEASE DO NOT ENTER THE DRIVEWAY. THANK YOU

This home is the perfect chance to live in a sweet neighborhood with a short stroll to the village. With solid bones, a welcoming front porch, and a detached garage ideal for work shop/studio/storage. Located in a convenient setting, it's ready for your vision, with opportunities for modern updates. A little work could mean a big reward. Housatonic Village a few steps away. Lovely back yard! Being sold as-is

At the Lenox/Stockbridge town line on the shore of Lily Pond, sits this architectural gem! Offering a rare combination of privacy artfully aligned with nature and a premier location. Set on six acres within the grounds of the original historic Wheatleigh estate, the property is within walking distance of Tanglewood, the Linde Center, Kripalu and Lenox village. Designed by Berkshire architect David Rothstein, the house is ideally positioned to engage its landscape. Large bay windows invite natural light and frame views of water, trees, and gardens. Custom cherry woodwork adds warmth and craftsmanship. The layout is both flexible and refined. First floor primary suite supports single level living, while 3 additional bedrooms and a library occupy the upper level. Lofts, towers and quiet alcoves create varied, unexpected spaces without sacrificing function. Post-and-beam great-room/atrium w stone floor takes center stage for entertaining. A former indoor pool has been transformed into a st

Set well back from a quiet road beneath mature trees, this one-owner West Stockbridge home offers an immediate sense of privacy, with gardens, lawn and woods gathered around it. Peaceful without feeling isolated, the house has the easy spirit of a modern farmhouse and a relaxed connection to its Berkshire setting.Inside, generous windows bring the landscape into nearly every room. Sunlight moves across bamboo floors, radiant heat adds warmth underfoot, and long sightlines connect the living, dining and kitchen spaces while allowing each to retain its own character. The kitchen sits naturally at the center of daily life with generous workspace and garden views.A light-filled sunroom is a standout, with a cathedral ceiling, exposed beams and windows on three sides overlooking the surrounding greenery. The inviting front porch and rear deck create additional places to sit, dine and enjoy the changing seasons.Upstairs, a broad landing anchors the second floor. The primary bedroom includes

At the Lenox/Stockbridge town line on the shore of Lily Pond, sits this architectural gem! Offering a rare combination of privacy artfully aligned with nature and a premier location. Set on six acres within the grounds of the original historic Wheatleigh estate, the property is within walking distance of Tanglewood, the Linde Center, Kripalu and Lenox village. Designed by Berkshire architect David Rothstein, the house is ideally positioned to engage its landscape. Large bay windows invite natural light and frame views of water, trees, and gardens. Custom cherry woodwork adds warmth and craftsmanship. The layout is both flexible and refined. First floor primary suite supports single level living, while 3 additional bedrooms and a library occupy the upper level. Lofts, towers and quiet alcoves create varied, unexpected spaces without sacrificing function. Post-and-beam great-room/atrium w stone floor takes center stage for entertaining. A former indoor pool has been transformed into a st

Newly updated Housatonic cottage set on the corner of Kirk and Fairview. Two bedrooms, two baths, lovely living space, and a sweet screened porch and patio. The lot has potential for expanded gardens or recreational space. Seasonal views to Flagg Mtn. A perfect location and setting

The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental. The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a strong performer for weddings, corporate retreats, and multi-generational stays. The grounds feature open lawns, established gardens, and west-facing views. Fully ADA compliant and walkable to Lenox's restaurants, shops, and cultural venues. A rare opportunity to own a large-scale, income-producing property in one of the Berkshires' most established locations