165 properties for sale in Lenox Dale

Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket doors that provide charm and flexibility. Every detail has been curated to embody warmth and sophistication, creating an inviting ambiance that is both refined and welcoming. Ideally located just moments from downtown Lenox, Tanglewood, a local municipal airport and a charming farm, HomeFarm, directly across the street. Highwick offers an unparalleled sanctuary in the heart of the Berkshires!

Some homes are purchased. Others become part of a family's legacy. Welcome to 109 Under Mountain Road. There is something unmistakably special about a Berkshire summer- evening stroll to Tanglewood, morning coffee overlooking protected meadows, or relaxing on the patio as the music of the Boston Symphony Orchestra drifts softly through the evening air. Bathed in extraordinary natural light, this architect-designed home embraces its breathtaking setting with soaring walls of glass, vaulted ceilings, exposed beams, skylights, and exquisite gardens. Thoughtfully designed for gracious entertaining and comfortable everyday living, the spacious first-floor primary suite allows you to enjoy the home with ease for years to come, while family and friends gather in beautifully appointed guest rooms

Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket doors that provide charm and flexibility. Every detail has been curated to embody warmth and sophistication, creating an inviting ambiance that is both refined and welcoming. Ideally located just moments from downtown Lenox, Tanglewood, a local municipal airport and a charming farm, HomeFarm, directly across the street. Highwick offers an unparalleled sanctuary in the heart of the Berkshires!

This property has an immaculate fenced in back yard for all your summer activities. Inside boasts beautiful hardwood floors, Full bath on the 1st and 2nd Level. Large mudroom from the main entrance for all you winter and mud season needs. A paved driveway with plenty of private parking. A walkout from the lower level to the parking area with a tuck under car port. Recently painted exterior and a screened in porch in the back. 3 large bedrooms and a perfect den for office space or media room. Centrally located in the Berkshires within close proximity to Shopping, Groceries Stores and Tanglewood!

Stockbridge Contemporary surrounded by 5+ acres of privacy and deeded rights to the Beachwood Association private beach is just waiting for you to rebrand this mid century jewel. Open common spaces to gather and take in the nature surrounding the house, four bedrooms and three baths; main floor primary is en suite. The location of this property is perfect in all directions, conveniently located minutes from Tanglewood and Lenox and Stockbridge in the other. a must see!

This property has an immaculate fenced in back yard for all your summer activities. Inside boasts beautiful hardwood floors, Full bath on the 1st and 2nd Level. Large mudroom from the main entrance for all you winter and mud season needs. A paved driveway with plenty of private parking. A walkout from the lower level to the parking area with a tuck under car port. Recently painted exterior and a screened in porch in the back. 3 large bedrooms and a perfect den for office space or media room. Centrally located in the Berkshires within close proximity to Shopping, Groceries Stores and Tanglewood!

Opportunity to complete this renovation. Extensive site work has already been completed. $25,000 of Tree removal in 2022, kerosene tank removal in 2022, New Septic system designed and installed in 2023, Asbestos Remediation in 2025, New roof with new 3/4 plywood board in 2025, Installed 3 new remote controlled skylights in 2025, 3 more trees removed in 2025, U-driveway installed in 2025. Deeded Lake Rights and private beach for Owners Only. House is directly across from the path to the beach. Goose Pond is noted to be one of the cleanest lakes in Massachusetts. Finish this renovation or add a foundation of build your dream home in this highly sought after Lake Community

Compare for value in the Lenox market! Sweet, petite, move-in ready ranch. Living room and bedrooms with hardwood floors; two nicely updated bathrooms; eat-in kitchen opens to spacious, private rear deck. Bonus features include the oversized two car garage, Buderus boiler for natural gas heat, and over a 1/2 acre of open sunny lawn. Easy access to shopping, dining and all of the Berkshires' cultural attractions

Tucked into a peaceful wooded setting in Lenox, this architecturally distinctive contemporary home offers 2,189 square feet of living space on a private half acre lot. Designed with an asymmetrical exterior and a split level floor plan spanning three levels, this home offers unique character. Large windows fill the interior with natural light, while the open living areas create an inviting space. With its distinctive contemporary design and solid architecture, this property presents an exciting opportunity for thoughtful updates that can enhance both style and value. A rare chance to create something truly special in one of Lenox's most desirable settings. View in person and experience the warmth, character, and connection to nature that make this home so unique

Tucked into a peaceful wooded setting in Lenox, this architecturally distinctive contemporary home offers 2,189 square feet of living space on a private half acre lot. Designed with an asymmetrical exterior and a split level floor plan spanning three levels, this home offers unique character. Large windows fill the interior with natural light, while the open living areas create an inviting space. With its distinctive contemporary design and solid architecture, this property presents an exciting opportunity for thoughtful updates that can enhance both style and value. A rare chance to create something truly special in one of Lenox's most desirable settings. View in person and experience the warmth, character, and connection to nature that make this home so unique

Walk-to town Lenox condo! Just in time for summer in the Berkshires! Move-in ready two-bedroom condo at Morgan Manor. Freshly painted interior, custom blinds, updated lighting. This is one of a handful of units that has an attached garage. Laundry (stack unit) has also been brought into this unit saving steps into the basement shared washer/dryers. Condo fees include natural gas heat, hot water, water/sewer, basic cable/internet. A great investment or owner-occupied dwelling. Private storage space in the basement. Minutes to shopping, library, dining and Tanglewood!

Experience refined Berkshire living at Devon Meadows, one of the area's most desirable luxury condominium communities. This beautifully appointed residence offers the ease of a first-floor primary suite combined with sophisticated design and exceptional comfort throughout. The open-concept floor plan features soaring ceilings, abundant natural light, and elegant modern finishes. The chef's kitchen is thoughtfully designed with quartz countertops, custom cabinetry, and seamless flow into the dining and living spaces-perfect for both everyday living and entertaining. Custom built-ins add character and functionality, while an inviting den or home office on the main level provides flexible space for work or relaxation. Guests will appreciate the privacy of well-appointed en-suite bedrooms

A house that stops people mid-sentence! At the Lenox/Stockbridge line on the western shore of Lily Pond, discover this one-of-a-kind home. A rare architectural sanctuary where nature, privacy, and imagination quietly redefine Berkshire living. Embraced by woods and water, this 4br, 4ba contemporary is bathed in extraordinary light. Enter and you'll find over 5000 sf. living space. Bedrooms are spaced apart for maximum privacy; the open living area takes center stage for entertaining. Post-and-beam great-room/atrium w stone floor. Open kitchen w custom cherry cabinetry. First floor primary suite. Outside, enjoy over 4 acres of privacy: lawn, gardens and your own nature trails! Deeded rights to the White Pines beach on Stockbridge Bowl. Walking distance to Tanglewood! Must see!

Perfect vacation or full-time Condo in a great spot at The Pines at Bousquet. Tons of year round activities at your finger tips in the Berkshires. This fabulous End unit has 3 stories of finished space including 5 Bedrooms, 4.5 baths, eat-in kitchen, large living room with gas fireplace and large den in lower level. An abundance of natural light throughout with tons of windows, a great feature for this end unit. A First floor Primary bedroom with en-suite full bath is a bonus. Other features include a screened in porch with an awesome view, lower patio perfect for your grill and entertaining and plenty of windows. Enjoy the 2021 renovations at Bousquet Mountain Complex, plenty of shopping close by and many cultural activities. This condo currently has tenants with a lease in place to Feb. 2028. See Realtor remarks for more details. Don't wait to see this Great Condo with monthly income in place

Experience refined Berkshire living at Devon Meadows, one of the area's most desirable luxury condominium communities. This beautifully appointed residence offers the ease of a first-floor primary suite combined with sophisticated design and exceptional comfort throughout. The open-concept floor plan features soaring ceilings, abundant natural light, and elegant modern finishes. The chef's kitchen is thoughtfully designed with quartz countertops, custom cabinetry, and seamless flow into the dining and living spaces-perfect for both everyday living and entertaining. Custom built-ins add character and functionality, while an inviting den or home office on the main level provides flexible space for work or relaxation. Guests will appreciate the privacy of well-appointed en-suite bedrooms

A house that stops people mid-sentence! At the Lenox/Stockbridge line on the western shore of Lily Pond, discover this one-of-a-kind home. A rare architectural sanctuary where nature, privacy, and imagination quietly redefine Berkshire living. Embraced by woods and water, this 4br, 4ba contemporary is bathed in extraordinary light. Enter and you'll find over 5000 sf. living space. Bedrooms are spaced apart for maximum privacy; the open living area takes center stage for entertaining. Post-and-beam great-room/atrium w stone floor. Open kitchen w custom cherry cabinetry. First floor primary suite. Outside, enjoy over 4 acres of privacy: lawn, gardens and your own nature trails! Deeded rights to the White Pines beach on Stockbridge Bowl. Walking distance to Tanglewood! Must see!

Just two miles from the center of Stockbridge, this beautiful four bedroom, three and a half bathroom home offers privacy, space and exceptional indoor outdoor living. The spacious primary suite features a large ensuite bath and separate his and her closets, and an additional closet with direct access to a full length deck shared access with the living room. The open floor plan connects the living room, dining area and kitchen, highlighted by soaring beamed ceilings abundant natural light, and a gas fireplace. A bright sunroom to choose a book from its floor to ceiling bookcases. The deck overlooks the mature landscaping, pool, and pool house. The walkout lower level includes a second kitchen, providing space for guests. A Berkshire retreat just minutes from the cultural attractions!

Just two miles from the center of Stockbridge, this beautiful four bedroom, three and a half bathroom home offers privacy, space and exceptional indoor outdoor living. The spacious primary suite features a large ensuite bath and separate his and her closets, and an additional closet with direct access to a full length deck shared access with the living room. The open floor plan connects the living room, dining area and kitchen, highlighted by soaring beamed ceilings abundant natural light, and a gas fireplace. A bright sunroom to choose a book from its floor to ceiling bookcases. The deck overlooks the mature landscaping, pool, and pool house. The walkout lower level includes a second kitchen, providing space for guests. A Berkshire retreat just minutes from the cultural attractions!

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

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

Quitessential 1830's side hall Colonial. charming home located in the village of Interlaken in the town of Stockbridge, MA. just minutes to Lenox, Stockbridge center and the Berkshire Botanical Center. Listen to the babbeling water from the Larrywaug Brook and walk just steps to the small town park. sit on the deck or around the firepit to soak in the atmosphere of privacy and peacefullness. This 3 bedroom, 1.5 bath house has been miticulously updated including: roof, windows, deck, painting, kitchen, baths, cement clapboard, wood flooring, laundry on main level. Full walkout basement, oil heat, central air, town water, town sewer. garage is partitioned for a workshop but can easily be converted to a one car garage again

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

Welcome to this beautifully maintained Cape Cod-style home, built in 2001 and set on 1.13 acres. Offering 3 bedrooms and 2.5 baths, this inviting home combines charm with a thoughtfully designed floor plan that's perfect for everyday living and entertaining. The main level features a private office with elegant French doors, ideal for working from home or creating a quiet retreat. The spacious living room is warmed by a cozy gas fireplace and opens to an expansive 12' x 30' partially screened deck, creating the perfect setting for outdoor dining, entertaining, or simply relaxing while enjoying the peaceful backyard. Upstairs, you'll find a primary suite complete with its own private bath and patio. Two additional bedrooms provide plenty of room for family and guests. The walkout basement offers extra space for a playroom, game room or potential in-law apartment. It has plumbing for another bathroom. The private backyard offers beautiful views and a great above ground pool. Please allow

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 serenity. Second level has ample space with three guest bedrooms, two full baths and loft/office space open to the great room. The lower level walkout family room is gracious in size and has direct access to your private stone patio. Additionally, you have the fifth bedroom, full bath, laundry room and bonus storage room. Enjoy the association pool, Bousquet Mountain next door and all of the

Set across 30+ pristine Berkshire acres, this property offers sweeping westerly mountain views, gently rolling fields, and Cone Brook running the length of the land to Shaker Mill Pond. With approximately 2,000 feet of frontage on Swamp Road, the possibilities are wide open: farming, equestrian use, a private estate, or potential subdivision into 6+ buildable lots. Two substantial barns, both equipped with electric and water, are already in place, offering immediate utility and flexibility. The setting is both scenic and convenient and just minutes to the village of West Stockbridge. A short drive to Tanglewood and Lenox, and within easy reach of ski areas. Additionally, a 1950s four-bedroom, two-bath home with a heated basement sits along the road frontage, ready for renovation or a fresh start. Come for the land-and shape it into something exceptional