Turnkey Berkshire Retreat Near Stockbridge Bowl & Tanglewood - Embrace effortless seasonal living in this beautifully maintained, vintage three-season cottage. Nestled on a quiet, unpaved lane in the desirable Mahkeenac Heights community, this two-bedroom home offers the quintessential Berkshires getaway. Recent thoughtful updates include fresh flooring and an opened-up floor plan that maximizes natural light and flow. Step outside onto expansive decking designed for alfresco dining. Whether you are spending your mornings at the local lake beach or your evenings taking in world-class music at nearby Tanglewood, this private haven offers prime proximity to the best of Lenox and Stockbridge.

Welcome to your own private slice of the Berkshires! Nestled on 3.09 picturesque acres in the town of Cheshire, MA, this beautifully maintained 3- bedroom, 2 bath home offers the perfect blend of comfort, privacy and natural beauty. From the moment you arrive, you'll appreciate the pride of ownership this well kept property. The inviting home features spacious living areas, comfortable bedrooms with the primary having a balcony to relax on. Step outside and discover what truly makes this property special. The expansive yard is beautifully landscaped, providing plenty of space for gardening and recreation, or simply relaxing while enjoying the peaceful surroundings. A tranquil pond adds to the property's charm.

NEW TO MARKET. Immaculate mid-century home on coveted Payn Avenue in Chatham Village NY. Rarely do homes in this neighborhood come available. Established, quiet, and family-friendly. Memorial Fields recreational area, shopping, schools within a half-mile. Central A/C and hardwood floors throughout incl parquet kitchen. 3BR/2BA (3rd BR currently laundry rm), LR w/FIREPLACE, large dining area off user-friendly modern kitchen. Primary BR w/primary bath. Glass sunroom overlooks the fully fenced, large backyard ideal for large gatherings. Solid covered canopy great for BBQing or reading in the warm breeze. Add'l lot included for a total .67 acre. Attached 2-car garage, full basement and paved driveway among amenities. 1 mile to Taconic Parkway. Owners relocating; home I

Nice 3 bedroom contemporary home set on over nine acres with Center Pond Brook flowing past the garden areas & through the back yard. The front porch opens onto the main kitchen & living areas with hardwood floors & cathedral ceilings. French doors lead to the sunroom overlooking the garden areas. The first floor primary bedroom features two walk in closets, built in dressers & desk. More built ins are found in the recently updated first floor bath. The upper level loft overlooks the living area & includes a full bath with tub/shower combination. A deck in the upstairs bedroom has views of the garden areas & brook. A large recreation room on the lower level features a slider to the gardens. The detached 2 car garage with large loft has many potential uses, studio, ADU, storage, etc.

Welcome to 1350 Massachusetts Ave -- a distinctive North Adams property offering space, character, and a rare combination of indoor and outdoor amenities. With 4 bedrooms, 1.5 bathrooms, and an expansive lot, this home offers room to live, entertain, relax, and make it your own. A true highlight of the property is the two-level wrap around deck, creating an exceptional outdoor living space that connects the home's porch and garage. Whether you're hosting summer gatherings, enjoying a quiet morning coffee, or spending evenings outdoors, this unique setup provides an abundance of usable space and multiple areas to enjoy.

This beautifully maintained 1,900 sq. ft. ranch offers comfortable single-level living with a bright, open floor plan and plenty of natural light. 3.21 Acres - Two Garages plus a Full Walkout Basement! The inviting kitchen features marble countertops, while beautiful hardwood floors and a custom fireplace add warmth and character throughout. The spacious walkout basement includes a Smith furnace and Fire Chief wood stove, providing flexible heating options. Set back from the road and abutting Crystal Pond, this peaceful private setting is the perfect place to enjoy the beautiful fall season. Property features two garages, two driveways, a barn, ample parking, and hookups for a future hot tub. Conveniently located just 34 minutes to Westfield, 19 minutes to Lee, and 26 minutes to Pittsfiel

Privacy, space, and the beauty of the Berkshires come together at 125 Town Hill Road. Set on nearly 3 wooded acres in the peaceful town of Sandisfield, this 4-bedroom, 3-bath contemporary offers a private retreat surrounded by nature. The home features comfortable living spaces, a screened porch, spacious deck, finished walk-out lower level, and a private tennis court. Enjoy the serenity of country living while being conveniently located near lakes, hiking, skiing, restaurants, galleries, and the charming towns of the southern Berkshires. A special setting for a year-round home or Berkshire getaway.

Set within one of Southeast Pittsfield's most desirable neighborhood settings, 53 Greenings offers an exceptional blend of privacy, space, and effortless everyday living. Set on a beautifully landscaped 1.07-acre double lot, this spacious ranch style residence feels wonderfully secluded while remaining connected to the conveniences and amenities of the surrounding community. Mature landscaping, established flower beds, and expansive lawn create a truly park-like setting, an inviting backdrop for morning coffee, summer gatherings, or simply enjoying the quiet of home.

Beautiful escape beside Little Robin Lake. This beautifully remodeled home features three inviting bedrooms and two elegant bathrooms, perfect for unwinding after a day of adventure. The sunroom, surrounds you in natural light, inviting you to relax with a good book or enjoy peaceful views. Soak in the sun on the large deck looking over the stunning lake scenery. Indulge in the luxury of the jet tub after exploring the outdoors. This private getaway, thriving as an Airbnb and is cherished as a second home. If you're seeking adventure or a peaceful retreat, this lakeside haven promises an unforgettable escape. Welcome to your home away from home, where every moment celebrates life by the lake.

Beautifully refurbished home in the Berkshires with deeded rights to the White Lily Pond Association, offering access to a private beach, tennis and pickleball courts. White Lily Pond is a quiet lake ideal for canoeing, kayaking, paddleboarding, and trolling motors only. Renovated with quality craftsmanship throughout, the home features upgraded insulation, efficient propane heat, and inviting living spaces. The custom kitchen includes granite countertops, a large island, gas range, and custom cabinetry. The living area is highlighted by a fireplace with handcrafted custom sconces. Otis Ridge Ski , Jacobs Pillow, Tanglewood are within minutes of home. A perfect year-round home or Berkshire getaway in desirable Otis.

If privacy, breathtaking mountain views, and a beautifully updated home are on your wish list, this property delivers! Tucked away on a private dead-end street yet only 5-10 minutes from downtown amenities, this home offers the perfect balance of peaceful living and convenience. Enjoy stunning views of Mt. Greylock and the surrounding mountain ranges from this spacious, well-maintained property. Pull into the paved driveway and right into the attached two-car garage. Major updates provide peace of mind, including a new asphalt shingle roof (2025), vinyl siding, hot water heater (2024), furnace (2026), vinyl windows throughout, and new gutters (2026).

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.

Tucked away at the end of a quiet dead-end street with zero through-traffic, this newer, expansive Colonial offers grand scale, total privacy, and an unbeatable location just 20 minutes from the New York border. It truly feels like your own hidden retreat, yet you are just minutes from the lake, a local dog park, shopping, and dining.The exterior boasts incredible curb appeal with its premium, freshly stained redwood-toned cedar siding and a brand-new roof. Step out into your backyard paradise, featuring a newly stained dark green entertaining deck, a sparkling aboveground pool with its own custom surrounding deck, and a spacious matching shed for all your outdoor storage needs. Quality finishes throughout the Interior!

Welcome to 16 Maple Street, Adams, MA--a breathtaking, recently renovated luxury Victorian estate that perfectly pairs timeless Victorian charm and grand architectural heritage with high-end, modern income functionality.From the moment you arrive, the home's striking historical presence captivates you. The exterior showcases beautiful, classic awnings and crisp white trim that beautifully accentuates its authentic Victorian silhouette. This beautiful, fully furnished luxury property is an absolute masterpiece, thoughtfully curated to preserve its original character and elegant craftsmanship--while offering premium upgrades for modern living.Boasting a versatile layout with 3 full bathrooms, the home is meticulously configured to generate exceptional income on both sides as an active Airbnb

Welcome to Peggy's Cottage. The owner, a cellist, originally chose this Queechy Lake home for its proximity to Tanglewood and the cathedral ceilings in the family room, which served as her music room. She quickly grew to love the lake community's friendly neighbors, walking trails, and private beach. This cozy log cabin sits on a level .36 acre lot, offering rare privacy with lovely gardens, a latticed entertainment deck, and two sheds. Relax in the living room in front of the stone fireplace, perfect for a quiet conversation or reading. Step into the spacious family/music room and enjoy movie night and the view of the gardens. The open kitchen and dining area connect to a first-floor bedroom with laundry and a full bath. Upstairs, you will find two large bedrooms with skylights and...

Completely renovated contemporary home on almost 10 acres of marvelous land. The home sits back from the road, offering tranquility and privacy. The first floor features two bedrooms and an additional room with a wood-burning fireplace which can be used as a recreation room or a third bedroom. Downstairs you will also find a large laundry room with epoxy flooring, and a brand new full bathroom. The second floor offers an open concept and features a brand new kitchen with quartz countertops, a great room with a wood stove, a cozy dining area and a new full bathroom with a jetted tub. You will feel like you are at a spa! Relax and enjoy nature from your tub or step outside to the new deck that wraps around the home.

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 newer 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!

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.

Beautiful early 1900's colonial farm house with deeded agricultural and horticultural rights offering 2,104 sq ft of classic charm on a picturesque 2.3-acre lot. Spacious 4-bedroom, 2-full-bath home is close to the state forest with access to mountain biking and hiking trails. Main level includes a bright living room, formal dining room, and a generous kitchen with great storage. High ceilings, original details, and large windows bring warmth and character throughout. Upstairs are four well-sized bedrooms and a second full bath, plus bonus unfinished space in the attic ideal for an office, studio, or playroom. Enjoy the expansive private yard with pastoral views and a pond. The back deck is perfect for outdoor dining or relaxing. Very private but also close to downtown. Motivated sellers

Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra storage. Inside, enjoy abundant natural light in the glassed-in sunroom or relax on the multiple porches and decks. A key feature is the large, private in-law apartment, perfect for multi-generational living or rental income. Ideally located in the heart of Sheffield village, you'll enjoy the comforts of downtown just steps from your doorstep.