779 houses for sale in Lenox, Lenox town Berkshire County Massachusetts

Have you been searching for an affordable retreat in the Berkshires' OPTION # 2 = Cabin w/out the extra lots. Attention nature lovers, hikers and outdoor enthusiasts, this one is tucked within the Ashmere Lake community and may be just what you've been waiting for. Nestled among the trees on a private road, this 1-bedroom cottage offers a peaceful escape where mornings begin with birdsong and evenings end around the fire under the stars. The spacious living room features large windows that bring the outdoors in, while the oversized bedroom provides plenty of sleeping space for family and guests. Garage and Shed for extra storage. Bring your vision, your tools, and your love of the outdoors to restore this cabin into the getaway it was meant to be. EASY to show. Agents use ShowingTime

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

Downtown Creative District Investment Opportunity Positioned in the heart of Pittsfield's vibrant Downtown Creative District, this fully occupied and professionally managed four-family property offers investors a rare blend of stable income and exceptional location. Just steps from the renowned Barrington Stage Company, residents enjoy easy access to some of the city's best entertainment, dining, shopping, and cultural attractions. Each spacious unit features one to two bedrooms, providing comfortable living spaces that appeal to a broad tenant base. The property's prime downtown setting, strong occupancy history, and professional management make it a turnkey investment with immediate cash flow potential. Whether you're looking to expand your portfolio or secure a well-located multifamily asset in one of the Berkshires' most desirable urban neighborhoods, this attractive income-producing property is an opportunity not to be missed

To Be Built Home - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 8.94-acre lot (MLS #248342), featuring a private well, installed septic system, underground electric, and a 1,000-gallon underground propane tank. A proposed septic easement accommodates an abutting lot. Lots may be purchased separately. HOA maintains driveway and common land. Covenants require a minimum 2,000 sq. ft. home with two-car garage. Taxes shown are for land only

Adorable and accessible ranch in a secluded West Pittsfield neighborhood offers easy one-level living. Customized for a wheelchair user, this meticulously maintained home features wide doorways, a large bedroom with a reading/office nook and double closets, an open living room and kitchen layout, a bright, spacious bathroom, and a laundry/mudroom area with plenty of storage. Decking connects the inviting front porch to a private bistro-like patio bordered by raised garden beds in the fenced and landscaped backyard. Whether you have mobility issues now or would appreciate a small home with no stairs in which you can age in place, this could be your sweet Berkshire retreat

Custom built home situated on a private lot just minutes to GUIDOS! Impeccable home with open floor plan. kitchen, eating area, living room with fireplace. wood floors, tiled baths, gas heat, central air, established gardens including your very own blueberry patch!. A stunning house on a very special piece of take a look.

Come enjoy the peace and quiet in this beautifully redone two-family property! This home has been completely updated from top to bottom, including New Roof and Siding, new walls, floors, and kitchen. Brand new fence for added privacy, a fully renovated basement with fresh concrete flooring, new water heaters, washer and dryer hookups on both floors, in addition, an upgraded electrical system. Whether you're looking for a comfortable home or a great investment opportunity, this property is move-in ready and built to last

Offering an affordable path to homeownership, this property is ideal for buyers ready to trade renting for a place of their own or investors looking to expand their rental portfolio. The first floor includes an eat-in kitchen, first-floor laundry, and a flexible room for additional living space. Bring your ideas and make it your own over time. A covered back patio extends your living space outdoors, while the fenced backyard offers room for pets. Conveniently located in the heart of Pittsfield with easy access to downtown, shopping, restaurants, schools, public transportation, and major commuter routes

Excellent investment or owner-occupied opportunity! This two-family flat offers two 2-bedroom, 1-bath apartments in a convenient Pittsfield location. Features include hardwood floors, a walk-up attic, public water and sewer, natural gas heat and hot water, two electric meters, one boiler, two hot water heaters, a spacious backyard, and ample off-street parking. The first-floor unit is owner-occupied, while the second-floor unit is vacant and in need of repairs, offering excellent value-add potential. Conveniently located near Berkshire Medical Center, downtown, schools, parks, shopping, restaurants, and cultural attractions. Property is being sold AS IS

Spacious and inviting 4-bedroom, 3-bath home offering comfort, efficiency, and great indoor-outdoor living. Beautiful wood floors run throughout the main living areas, adding warmth and character. The private primary suite features its own bath and sliding doors leading to a deck that overlooks a fully fenced backyard-perfect for relaxing or entertaining. Enjoy the added bonus of a covered patio and a handy storage shed for all your outdoor needs. The partially finished lower level provides flexible space for a home office, gym, or recreation area. Energy-saving solar panels help keep electric costs down,and the convenient close proximity to the lake makes this home as practical as it is appealing

Move right into this beautifully updated Colonial on a quiet, tree-lined street! Thoughtfully renovated and lovingly maintained, this charming home is truly turnkey. Enjoy peace of mind with a new roof and new sewer line, along with a stunning new kitchen featuring stone countertops, upgraded stainless steel appliances, soft-close cabinets and drawers, and abundant workspace. The inviting floor plan is perfect for both everyday living and entertaining. Upstairs, the spacious primary bedroom offers two walk-in closets, providing exceptional storage. Outside, you'll find a fully fenced backyard-ideal for pets, play, or relaxing evenings-as well as a one-car garage. Need extra space' The basement includes a fantastic workshop area, perfect for hobbies, projects, or additional storage. Located in a desirable neighborhood with excellent schools, this lovely Colonial combines timeless character with modern updates, making it a home you'll be proud to own

Come enjoy the peace and quiet in this beautifully redone two-family property! This home has been completely updated from top to bottom, including New Roof and Siding, new walls, floors, and kitchen. Brand new fence for added privacy, a fully renovated basement with fresh concrete flooring, new water heaters, washer and dryer hookups on both floors, in addition, an upgraded electrical system. Whether you're looking for a comfortable home or a great investment opportunity, this property is move-in ready and built to last

Welcome home to this sweet split-level in desirable Southeast Pittsfield neighborhood. Offering 3 bedrooms and 1.5 baths, this well-maintained home features a spacious, well-appointed kitchen with granite countertops, abundant cabinetry, and great functionality for everyday living. Cozy up by the wood-burning fireplace or unwind in the inviting four-season room overlooking the deck and backyard. A walk out lower level is perfect as a home office, mudroom, or home gym, and there is and abundance of storage in the basement. Generously sized yard offers space to garden, play, or entertain. Just a short distance to nature tralis at both Brattlebrook Park, Kirvin Park and Canoe Meadows, this is a wonderful opportunity to enjoy comfortable living in a location you'll love

'A Perfect Place Farm' - a Berkshires Masterpiece on 17+ Acres The one you've been waiting for. a preeminent build in a premier location. 37 Main Rd checks off the wish list: sweeping views, modern comforts, privacy, location, and colonial era character, but in an immaculately kept turnkey 2002 home. Located in Tyringham valley, one of the Berkshires' most majestic locations, 37 Main Rd is idyllically sited on the northern slope of Tyringham valley, and faces to the southwest. The expansive front porch, sunroom, and living and sleeping quarters all are positioned to track the sun's daily arc across this picturesque east-west valley

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!

Positioned within walking distance to the vibrant downtown of Great Barrington, this property offers a unique opportunity for Homeowners, investors, non-profits, or developers seeking flexibility and future upside. Previously utilized as professional offices for mental health services, with vision, this could be converted into a 1 or 2 family home. Significant capital improvements have already been completed, including a newer boiler, newer hot water heater, a fully monitored smoke and CO detection system, and all windows replaced, ensuring efficiency and peace of mind for future ownership. The property sits on over one acre of land and features a large on-site parking lot and adjacent to a beautiful river. clients, or residents. Zoned residential, this property presents compelling redevelopment potential. Whether you envision a conversion to a single-family residence, multi-family housing, or a mixed-use concept (subject to approvals), the location and infrastructure support a wide ra

Renovated 4-family home, located on a corner lot in a great location in Pittsfield. There are two units on the first floor and two units on the second floor. The upstairs units also feature additional bonus space in the finished attics. Major updates were done in 2023-2024, with improvements that include new roof, new windows, new exterior doors, new second egresses for both upstairs unit, and new custom made fence. This is a solid building with 3,280 Sq ft and lots of character, and one of the most beautiful ones in the city! *Since the property sits on a corner, it is also known as 4 Courtland Pl. Pittsfield, MA 01201

Well-located home nestled in a desirable neighborhood with convenient access to local amenities, schools, and outdoor recreation. This inviting property offers a comfortable layout designed for everyday living and entertaining, featuring bright, sun-filled spaces and a warm, welcoming atmosphere throughout. The home provides a functional flow with generously sized living areas, a thoughtfully designed kitchen, and ample room to accommodate a variety of lifestyles. Bedrooms offer comfortable retreats, while additional space allows for a home office, guest area, or flex use to suit your needs. Enjoy the benefits of a private yard and deck, ideal for relaxing, gardening, or hosting gatherings. Whether you are a first-time buyer, downsizing, or looking for a Ber

Welcome to 22 Wealthy Ave located in the desirable Yankee Orchards neighborhood. Fresh, bright, and move in ready, this thoughtfully renovated home features beautifully refinished hardwood floors, a main level bedroom and full bath, plus two additional bedrooms upstairs with cedar lined closets, built in dresser drawers, and a newly renovated full bath. The updated kitchen includes a farmhouse sink, dishwasher, refrigerator, and oven/range. An attached garage with a new epoxy floor offers direct access to both the home and basement, where laundry hookups are conveniently located. Close to shopping, parks, schools, and downtown Pittsfield

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

Beautifully maintained inside and out, this move-in ready 3-bedroom Ranch offers the perfect blend of comfort, updates, and outdoor living. Gleaming hardwood floors, abundant natural light, and a stunning floor-to-ceiling stone fireplace create a warm, inviting living space. The finished lower level with custom bar adds exceptional bonus space for entertaining, hobbies, or relaxing. Outside, enjoy an expansive composite deck overlooking a beautifully landscaped, fully fenced backyard with fire pit and storage shed. Recent improvements include a new transferable 50-year roof (2025), fence (2025), remodeled bath, finished basement, deck, updated flooring, and more. Every room reflects the pride of ownership this home has received. Simply unpack, settle in, and enjoy

Located on the edge of Pittsfield's Downtown Creative District, this versatile colonial has served as professional office space for 20+ years and offers endless possibilities. Features include 6 private offices, a reception/waiting area, half bath, bonus room, handicap-accessible ramp, off-street parking, and a detached 4-bay garage with income potential. Ideal for medical, professional, nonprofit, wellness, counseling, mental health or substance abuse programs with residential living (subject to approvals), artist studios, or rental income. Restore it to a charming residence or continue its commercial use. Convenient to downtown and major routes in and out of the Berkshires. Bring your vision to where opportunity, location and flexibility come together. Talk to Tony

Welcome to this charming and low-maintenance ranch offering 1,131 square feet of comfortable single-level living. Situated on a quiet street in a desirable Pittsfield neighborhood, this two-bedroom, one-bath home is just minutes from Onota Lake and Pontoosuc Lake, providing easy access to boating, fishing, swimming, and year-round outdoor recreation. Inside, you'll find a functional floor plan designed for easy living, with bright, welcoming spaces that make everyday living and entertaining effortless. Step outside and enjoy your morning coffee on the inviting front deck or relax on the side patio surrounded by beautiful perennial gardens and colorful landscaping. The backyard offers additional outdoor space complete with a storage shed for gardening tools and seasonal equipment

Welcome to easy single floor living in a highly desirable Southeast Pittsfield neighborhood! Built in 2003, this exceptionally well-maintained contemporary home features 3 spacious bedrooms, 2 full baths, soaring vaulted ceilings, and beautiful hardwood floors. The light-filled primary suite includes a private ensuite bath, while the enclosed 3-season room and front porch offer ideal spots to relax overlooking a low-maintenance yard. Complete with a brand-new roof, central air, a massive unfinished basement with endless potential, and city-maintained street access, this move-in-ready property is a standout Berkshire home!

Well-located home nestled in a desirable neighborhood with convenient access to local amenities, schools, and outdoor recreation. This inviting property offers a comfortable layout designed for everyday living and entertaining, featuring bright, sun-filled spaces and a warm, welcoming atmosphere throughout. The home provides a functional flow with generously sized living areas, a thoughtfully designed kitchen, and ample room to accommodate a variety of lifestyles. Bedrooms offer comfortable retreats, while additional space allows for a home office, guest area, or flex use to suit your needs. Enjoy the benefits of a private yard and deck, ideal for relaxing, gardening, or hosting gatherings. Whether you are a first-time buyer, downsizing, or looking for a Ber