209 properties for sale in Larrywaug

Extraordinary, Inside and Out. This stylish log home on 3+ acres is the complete Berkshire retreat. Recently updated and improved, the home pairs modern lodge character with resort-like amenities. A heated saltwater gunite pool and integrated hot tub anchor the beautifully landscaped grounds. A locust fence encloses the pool area, with bluestone patio, lush lawn, and a stunning renovated pool house designed for entertaining, dining, or remote work. Inside, the home is warm, open, and full of character, with the added benefit of true one-level living. The great room is the centerpiece, with soaring ceilings, exposed log beams, and a substantial stone fireplace. The adjoining kitchen and dining areas are designed for gathering, with cherry floors, custom pine cabinetry, a large island, and stainless appliances. A large screened porch and wraparound deck extend the living space outdoors and take in the wooded setting and ridge views. The luxurious first-floor primary suite offers private

This move-in ready, sunny Cape next to the Botanical Garden offers significant upgrades, a four-season sunroom, private fenced backyard, attached garage, patio, first-floor bedroom and full bath, and low Stockbridge taxes. Hardwood floors, updated kitchen with pantry, mini-splits for heat and AC, new roof, gutters, windows, insulation, primary bath, and electric hot water heater make this truly turnkey. Minutes to Norman Rockwell (3), Tanglewood (9), The Mount (13), Shakespeare and Co (13), Ski Butternut (17), downtown Stockbridge (5), Lenox (12), Great Barrington (16) and I-90 (13). Cozy, year-round retreat on a quiet street - won't last long!

Extraordinary, Inside and Out. This stylish log home on 3+ acres is the complete Berkshire retreat. Recently updated and improved, the home pairs modern lodge character with resort-like amenities. A heated saltwater gunite pool and integrated hot tub anchor the beautifully landscaped grounds. A locust fence encloses the pool area, with bluestone patio, lush lawn, and a stunning renovated pool house designed for entertaining, dining, or remote work. Inside, the home is warm, open, and full of character, with the added benefit of true one-level living. The great room is the centerpiece, with soaring ceilings, exposed log beams, and a substantial stone fireplace. The adjoining kitchen and dining areas are designed for gathering, with cherry floors, custom pine cabinetry, a large island, and stainless appliances. A large screened porch and wraparound deck extend the living space outdoors and take in the wooded setting and ridge views. The luxurious first-floor primary suite offers private

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. A generous seller credit opportunity toward buyer's preferred improvements upon acceptable offer. Online psf is in error. Actual is $469 psf

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. A generous seller credit opportunity toward buyer's preferred improvements upon acceptable offer. Online psf is in error. Actual is $469 psf

This move-in ready, sunny Cape next to the Botanical Garden offers significant upgrades, a four-season sunroom, private fenced backyard, attached garage, patio, first-floor bedroom and full bath, and low Stockbridge taxes. Hardwood floors, updated kitchen with pantry, mini-splits for heat and AC, new roof, gutters, windows, insulation, primary bath, and electric hot water heater make this truly turnkey. Minutes to Norman Rockwell (3), Tanglewood (9), The Mount (13), Shakespeare and Co (13), Ski Butternut (17), downtown Stockbridge (5), Lenox (12), Great Barrington (16) and I-90 (13). Cozy, year-round retreat on a quiet street - won't last long!

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

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

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

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

Four-bedroom homes are a rarity at Coldbrooke, where most residences offer three. This one combines that hard-to-find layout and one of the community's more generous floor plans with a location beside the Miraval Berkshires resort and the historic Wyndhurst estate, putting world-class spa, dining, and golf just steps from the door. Inside, vaulted ceilings and an open layout fill the home with light. A thoughtfully updated kitchen anchors the main level, opening to a spacious great room with adjoining dining and living areas built for gathering. Out back, a screened porch and deck overlook the golf course, an easy setting for summer cookouts or a drink after a round. The first floor holds two generous bedrooms, each with its own en suite. The primary is a true retreat, anchored by a spa-like bath with an oversized walk-in shower, double vanity, and radiant heated floors, plus a large walk-in closet and a reading nook. Upstairs, a catwalk leads to two more spacious bedrooms sharing a fu

Beautifully reimagined New England farmhouse in Lee thoughtfully updated to blend modern comfort with its original charm. This inviting property is well suited as a Berkshire getaway, investment opportunity, or year-round primary residence. Since 2023, the home has undergone numerous improvements, including fresh interior and exterior paint, a new roof, owned solar panels, and the addition of a full first-floor bathroom, family room, and dining area. A rear deck provides an ideal setting for outdoor dining, entertaining, or peaceful relaxation. The expansive, sun-filled backyard offers ample room for gardening, recreation, and the potential for a future in-ground pool. Furniture package available

Welcome to this recently listed home in a sought after neighborhood in Lee MA. A truly lovely home in an exceptional setting! Minutes to many Berkshire cultural sites including Tanglewood, Jacobs Pillow and Shakespeare and Company. Enjoy swimming at Laurel Lake, hiking at Bear Town State forest, or shopping at the outlets nearby. This 3 bedroom, 2.5 bath home also includes a den/office, dining room, living room and large eat in kitchen. Enjoy the views and privacy from the oversized deck. Amenities include: finished lower level, vinyl siding, gas heat, public sewer and water, cable, wood floors, invisible dog fence, and two car attached garage. A great opportunity!

Tucked away in a peaceful, private setting, this charming mid-century ranch offers easy one -level living, warm and inviting. Featuring 3 bedrooms and 2 full baths, the home combines classic character with fresh updates. New oak floors throughout, fresh interior and exterior paint create a clean, move-in ready feel. Relax by the fire or enjoy time on the screened porch or deck. Minutes to town, Taft Farm, Guido's, Skiing and other notable Berkshire attractions

Set on a sunny half-acre lot, this classic 1900 ranch is ready for its next chapter and top/bottom reinvention.The home is now strictly an 'as-is' handyman special or contractor's dream. Features a cozy compact ( yes small ) kitchen, vintage vibes (meaning every room needs a facelift ),and dirt basement. Roof is holding strong for now, but you'll want to budget for a replacement soon (real sooner) The real star here? The land and location, half-acre of fantastic, usable Berkshires property, you have ample room to expand, build new, or execute a total dream renovation. Title V not complete, seller will not repair fails, will be the responsibility of the Buyer. Showings must be scheduled; the home is occupied. Won't qualify for most lending products

El Refugio, 'The Refuge', a hidden gem minutes from downtown Great Barrington. A 2-bedroom, 2-bath, wood burning fireplace home - with a 46' heated pool and 2-car detached garage. Set back from the road on 7+ private acres with extensive shoreline on the Williams River

Welcome to 12 Mountain St, a quintessential colonial masterpiece that blends classic elegance with modern functionality. Spanning over three expansive, light-filled floors, this stunning home offers five spacious bedrooms and 3.5 bathrooms, providing the ideal layout for those who love to entertain. The chef's kitchen is designed to inspire with high-end finishes, including a vast center island, a professional-grade Six-burner gas stove w/pot filler, chic quartz countertops. With an abundance of cabinetry and a dedicated, organized pantry featuring custom built-ins, this kitchen is as practical as it is beautiful. Gleaming hardwood floors flow throughout the main level, creating a seamless, inviting atmosphere. Ascend to the second floor, where you will find a tranquil primary en suite wit spa shower alongside two additional bedrooms connected by a well-appointed Jack-and-Jill bath. The third floor offers incredible flexibility with two more large, sun-drenched bedrooms and a dedicated

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

Immaculate Center Hall Colonial in one of Lee's most desirable neighborhoods. Beautifully maintained and move-in ready, this inviting home offers 3 bedrooms, 2.5 baths, plus a spacious game/bonus room. The first floor features a wonderful eat-in kitchen with granite counters and abundant cabinetry for the home chef, a large living room with fireplace, formal dining room, and gleaming hardwood floors. Upstairs, the en-suite primary provides a comfortable private retreat with two additional bedrooms. An attached two-car garage adds everyday convenience. Set on a beautiful residential street with a deck-perfect for grilling, morning coffee, or a glass of wine at the end of the day. Exceptionally well cared for plus, need more space, there is a walk out lower level waiting to be finished

Looking for a Berkshire getaway that can help pay for itself? This unique 6-unit property in Lee offers the rare opportunity to enjoy a spacious 4BR/2BA home of your own while generating income from 5 additional apartments. Full of character, the property retains many of its beautiful original features with significant updates, including renovations to 5 of the 6 units, a newer roof, updated electrical and newer heating systems. Set on a spacious property with ample parking, public water and sewer, and separate utilities, it offers tremendous flexibility for seasonal, short-term or year-round rentals. Centrally located near the Mass Pike, downtown Lee, Outlets, Tanglewood and all that the Berkshires have to offer. An ideal combination of Berkshire lifestyle, character and income potential!

IMMACULATE 3 BEDROOM APARTMENT WITH DECK and ONE BEDROOM APARTMENT in SOUTH LEE on a quiet cul de sac. Zoned 2 family, partially fenced back yard, attached garage, CENTRAL AIR CONDITIONING - BRAND NEW VINYL SIDING DECEMBER 2025

Immaculate 3-bedroom ranch with additional 750 square feet of finished living space in lower level. Move in condition, cathedral ceiling in living room and 2 full baths, Prmary with ensuite. Set way back off Park Street North on 0.62 level acres. 8+ acres owned by Land Conservation in your back yard adds peace and privacy

Tucked away on just under an acre of absolute privacy in beautiful Lee MA This modified Cape-style home is a masterclass in character. Ready for you to bring this home to its modern beauty! 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

For Sale: 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. T

Experience refined Berkshire living at Coldbrooke East, where timeless elegance meets exceptional privacy. Perfectly sited at the end of a quiet cul-de-sac and abutting the golf course, this extraordinary six-bedroom, 5.5-bath residence offers luxurious single-level living with a thoughtfully designed 1,000-square-foot addition. Custom designer finishes, exceptional craftsmanship, and substantial built-ins create a sophisticated yet comfortable totally renovated interior. Outside, magnificent perennial gardens, privacy, outdoor showers, and courtyard provides a serene retreat. Enjoy access to the nearby Wyndhurst Club and Manor pool, tennis courts, reduced-rate fitness membership, and more. A rare offering combining luxury, lifestyle, and one of Lenox's most coveted settings

Set on a sunny half-acre lot, this classic 1900 ranch is ready for its next chapter and top/bottom reinvention.The home is now strictly an 'as-is' handyman special or contractor's dream. Features a cozy compact ( yes small ) kitchen, vintage vibes (meaning every room needs a facelift ),and dirt basement. Roof is holding strong for now, but you'll want to budget for a replacement soon (real sooner) The real star here' The land and location, half-acre of fantastic, usable Berkshires property, you have ample room to expand, build new, or execute a total dream renovation. Title V not complete, seller will not repair fails, will be the responsibility of the Buyer. Showings must be scheduled; the home is occupied. Won't qualify for most lending products

Immaculate 3-bedroom ranch with additional 750 square feet of finished living space in lower level. Move in condition, cathedral ceiling in living room and 2 full baths, Prmary with ensuite. Set way back off Park Street North on 0.62 level acres. 8+ acres owned by Land Conservation in your back yard adds peace and privacy

Now offered at a new compelling price! Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living experience unlike anything else on the market. The first floor features an impressive great room with soaring timber beams, an elevated Malm fireplace, and floor-to-ceiling glass that captures the surrounding vistas. A gourmet kitchen imported in its entirety from Germany anchors the main living space with exceptional craftsmanship and modern sophistication. Radiant floor heat delivers year around comfort. The first-floor primary suite offers a private retreat with a spacious spa-like bath, featuring a large shower, soaking tub, and generous walk-in close

Welcome to 12 Mountain St, a quintessential colonial masterpiece that blends classic elegance with modern functionality. Spanning over three expansive, light-filled floors, this stunning home offers five spacious bedrooms and 3.5 bathrooms, providing the ideal layout for those who love to entertain. The chef's kitchen is designed to inspire with high-end finishes, including a vast center island, a professional-grade Six-burner gas stove w/pot filler, chic quartz countertops. With an abundance of cabinetry and a dedicated, organized pantry featuring custom built-ins, this kitchen is as practical as it is beautiful. Gleaming hardwood floors flow throughout the main level, creating a seamless, inviting atmosphere. Ascend to the second floor, where you will find a tranquil primary en suite wit spa shower alongside two additional bedrooms connected by a well-appointed Jack-and-Jill bath. The third floor offers incredible flexibility with two more large, sun-drenched bedrooms and a dedicated

Experience refined Berkshire living at Coldbrooke East, where timeless elegance meets exceptional privacy. Perfectly sited at the end of a quiet cul-de-sac and abutting the golf course, this extraordinary six-bedroom, 5.5-bath residence offers luxurious single-level living with a thoughtfully designed 1,000-square-foot addition. Custom designer finishes, exceptional craftsmanship, and substantial built-ins create a sophisticated yet comfortable totally renovated interior. Outside, magnificent perennial gardens, privacy, outdoor showers, and courtyard provides a serene retreat. Enjoy access to the nearby Wyndhurst Club and Manor pool, tennis courts, reduced-rate fitness membership, and more. A rare offering combining luxury, lifestyle, and one of Lenox's most coveted settings