86 properties for sale in Vacation Village, Hancock town Berkshire County Massachusetts

Renovated Gothic Barn in an Unbeatable Berkshire Location. Location, Location, Location! This beautifully renovated Gothic Barn offers timeless architectural character paired with modern comfort and convenience. Move-in ready, this exceptional property features 3 bedrooms, 3 full bathrooms, and an impressive list of high-end upgrades throughout. Enjoy peaceful mornings and scenic sunsets from two brand-new decks overlooking picturesque views. Inside, the home has been thoughtfully updated with Andersen windows, doors, and sliding glass doors, durable Hardie Board siding, fresh interior and exterior paint, refinished hardwood floors, and central air conditioning. The stunning chef's kitchen is equipped with Cafe appliances, granite countertops, and premium finishes, while all three bathrooms have been completely gutted and renovated with contemporary fixtures and design. Additional upgrades include updated electrical and plumbing systems, a new heating system and furnace, floating stair

Discover the perfect mountain retreat in this beautifully maintained 2-bedroom, 2 full bath condo offering 1,030 square feet of comfortable living space. Ideally located just moments from the ski slopes, this home is a dream for outdoor enthusiasts and year-round adventurers. Enjoy easy access to a wide range of community amenities, including a heated pool, tennis courts, and beautifully maintained grounds. Whether you're hitting the slopes in winter, enjoying summer recreation, or simply unwinding in a peaceful setting, this condo offers the ideal blend of convenience and lifestyle. Perfect as a primary residence, vacation getaway, or investment property, this is your opportunity to own a slice of mountain living at its best

Slope-side living at Jiminy Peak with proven income potential! Located just steps from the ski slopes and very close to the year-round heated pool, this beautifully positioned one-bedroom suite offers the perfect Berkshire getaway and an exceptional short-term rental opportunity. Currently operated as a successful Airbnb/short-term rental, the unit generated approximately $17,162 in net income after expenses in 2025 and over $20,000 in 2024, making this an attractive option for both lifestyle buyers and investors seeking a turnkey four-season property. Unit 521 combines the charm of a cozy mountain retreat with the convenience of full resort amenities, including an outdoor heated pool, fitness center, sauna/steam room, on-site dining, front desk services, and tennis courts Exceptional opportunity to own a proven income-producing resort condominium at the base of Jiminy Peak Mountain Resort in the heart of the Berkshires. Located just steps from the ski slopes and very close to the year

Location. location. location. Enjoy the ultimate convenience of living at a ski resort, with easy access to slopes, hiking trails, mountain biking, dining, and other resort amenities right at your doorstep. Wood burning fireplace will keep you warm on those cold winter nights. Embrace the year-round mountain lifestyle in this exceptional 3-bedroom, 2-full-bath home, ideally situated for both adventure and relaxation. Nestled on a street within a premier ski resort community, this property offers a peaceful sanctuary steps from the summer pool

At the base of Jiminy Peak, skiing is just steps from your door in one of these one bedroom all suites' condominiums with kitchens that offer the charm of a countryside inn and the conveniences of a slope side hotel. Whirlpools, year-round outdoor swimming pool, exercise room, in house restaurant and on-site front desk services makes this and easy decision to own. Excellent rental history and no hassle management allows for time to enjoy all Jiminy Peak offers on a year round basis

Berkshires Luxury and New Lakeside Living. Enjoy distant lake and mountain views from each first floor room. This elevated ranch style home creates one level living with grand open sunfilled spaces. This floorplan features open floor plan capturing lakeviews from each room on the main living level. This beauty is what you have been waiting for - a brand new never lived in newly constructed home is ready for you to live and enjoy the Berkshires at it's best now. Expansive gourmet kitchen topped with quartz quality counters, stainless appliances, breakfast bar and oversized walk-in pantry. Dining room flows to living room with sliders leading to a glorious continuous wrap-around upper level deck. Custom wire railings enhance views and is oversized for outside dining and chaise lounging. Primary first floor suite gives you vacation views from your kingsize bedroom, enjoy luxury double sink vanity, kohler fixtures, and luxury tiles walk in shower. A dream walk in closet is outfitted with s

Build to suit. This new construction modular home offers an open concept kitchen, dining and living room space, The home features grand, open, sun-filled spaces with an open floor plan that is designed to capture Pontoosuc lake and mountain views from every room on the main living level. 4 bedrooms 3 baths. Purchase as specked or chose upgrades to finish home to your desires. Lake access available within walking distance. Building plans available at request

This solidly built home boasts a strong foundation and timeless charm. Step inside to beautifully maintained original oak and pine hardwood floors. The heart of the home features a sleek kitchen updated three years ago, complete with quartz countertops and stainless steel appliances. The layout offers extra versatility with a finished basement room, while the finished attic serves primarily as a spacious primary bedroom suite. Enjoy peace of mind with a roof updated in phases (2016 and 2020). Bring your custom design ideas to personalize the bathroom!

Set on an expansive 21.6-acre private landscape, This 3bed, 2.5-bath home blends comfort, space and versatility. The main level offers a warm, open layout with a bright living area, a functional kitchen, and easy flow to the outdoor spaces, perfect for everyday living or entertaining. The 3 bedrooms, including a comfortable primary suite, provide plenty of room to unwind. A standout feature of this property is the walk-out basement, offering exceptional flexibility. Downstairs you'll find 3 bonus rooms ideal for home office, guest space, or hobby rooms, along with a full bath, creating a great setup for multi-generational living or expanded recreational use. Outside, the acreage delivers privacy, wooded surroundings, whether you envision trails, gardens, or simply enjoying peaceful setting!

Enjoy Pontoosuc Lake views year round in this peaceful Lanesborough home with walkable lake access! Thoughtfully updated throughout, this move-in-ready 3 BR, 2 Full Bath home offers additional flex space with a first floor bath to suit your needs. The large lot with patio and firepit are excellent for entertaining, while leaving plenty of yard space for gardening and other hobbies. Ideally located, you'll also be just minutes from some of the Berkshires' most popular ski areas, easy access to hiking, golf, pickle ball, shopping, dining, and the world-class arts and cultural attractions that make the Berkshires such a special place to call home

Just minutes from Pontoosuc Lake, this charming two-bedroom, two-bath home offers the perfect combination of comfort, style, and convenience in a sought-after lake neighborhood. Filled with natural light throughout, the home features partial lake views and lake access right at the end of the street. Inside, you'll find a bright and inviting layout with tasteful updates throughout. The kitchen offers stainless steel appliances and ample cabinet space. The cozy pellet stove creates a warm welcoming home, while modern mini-splits provide efficient heating and cooling. The home also features updated bathrooms and generously sized bedrooms. Additional finished space in the basement offers flexibility for a family room, home office, or guests. Whether you're looking for a year-round residence or the perfect Berkshire retreat, this adorable home is a must see!

Build to suit. This new ranch construction modular home offers an open concept kitchen, dining and living room space, The home features open, sun-filled spaces with an open floor plan that is designed to capture Pontoosuc lake and mountain views from every room on the main living level. 3 bedrooms 2 baths. Walkout lower level ready for additional finished space. Purchase as specked or chose upgrades to finish home to your desires. Lake access available within walking distance. Building plans available at request

A GREAT OPPORTUNITY WAITS FOR YOU. A FOUR BEDROOM, TWO BATH HOME 75 FEET FROM THE BEACH WITH VIEWS OF PONTOOSUC LAKE, AT A VERY REASONABLE PRICE. THIS QUAINT HOME WITH A LOVELY FRONT PORCH, BEAUTIFUL, MATURE GARDENS, SIDE DECK AND HARDWOOD FLOORS HAS BEEN IN THIS FAMILY FOR OVER 75 YEARS OF ENJOYABLE MEMORIES. COME SEE IT WHILE IT IS STILL AVAILABLE

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

Set on Aspen Way in Pittsfield, this well-maintained condo offers a practical layout and easy, low-maintenance living in a desirable community. The main level welcomes you with an open living area featuring a gas fireplace, flowing into a spacious dining area. The kitchen is positioned at the back of the home and is finished with stainless steel appliances and granite countertops, with a slider that opens directly to the deck-an easy extension for outdoor dining or relaxing. The primary suite offers a spacious retreat with a large en-suite bathroom and walk-in closet, while two additional bedrooms share a full bath. Designed for one-level living, the first floor also includes laundry for added convenience. Additional features include a two-car attached garage and a full unfinishe basement, offering ample storage and the potential to create additional living space such as a family room, game room, or home gym. A clean, functional condo with a strong balance of space, convenience, and fu

Step into this beautifully updated 3-bedroom, 3-bathroom with a lretreat nestled in one of Jiminy's most family-friendly neighborhoods. 2 bedrooms and 2 Full baths on the 1st floor. The open-concept living area features floor-to-ceiling windows that flood the space with natural light, highlighting the elegant hardwood flooring and cozy fireplace. The gourmet kitchen boasts quartz countertops and top-of-the-line stainless steel appliances, perfect for entertaining. The primary suite offers a spa-inspired bathroom with a walk-in shower. Outside, the meticulously landscaped, fenced-in patio provides a private sanctuary, complete with plenty of room for al fresco dining. Enjoy the convenience of being just a short walk from the slopes and local shops. Upstairs boosts a spacious loft

At the base of Jiminy Peak, skiing is just steps from your door in one of these one bedroom all suites' condominiums with kitchens that offer the charm of a countryside inn and the conveniences of a slope side hotel. Whirlpools, year-round outdoor swimming pool, exercise room, in house restaurant and on-site front desk services makes this and easy decision to own. Excellent rental history and no hassle management allows for time to enjoy all Jiminy Peak offers on a year round basis

At the base of Jiminy Peak, skiing is just steps from your door in one of these one bedroom all suites' condominiums with kitchens that offer the charm of a countryside inn and the conveniences of a slope side hotel. Whirlpools, year-round outdoor swimming pool, exercise room, in house restaurant and on-site front desk services makes this and easy decision to own. Excellent rental history and no hassle management allows for time to enjoy all Jiminy Peak offers on a year round basis

Location. Location. Location. Enjoy the ultimate convenience of living at a ski resort, with easy access to slopes, hiking trails, mountain biking, dining, and other resort amenities right at your doorstep. Wood burning fireplace will keep you warm on those cold winter nights. Embrace the year-round mountain lifestyle in this exceptional 3-bedroom, 2-full-bath home, ideally situated for both adventure and relaxation. Nestled on a street within a premier ski resort community, this property offers a peaceful sanctuary steps from the summer pool

At the base of Jiminy Peak, skiing is just steps from your door in one of these one bedroom all suites' condominiums with kitchens that offer the charm of a countryside inn and the conveniences of a slope side hotel. Whirlpools, year-round outdoor swimming pool, exercise room, in house restaurant and on-site front desk services makes this and easy decision to own. Excellent rental history and no hassle management allows for time to enjoy all Jiminy Peak offers on a year round basis

Charming 1930s Cape with 11 Acres of serene bliss. Welcome to your own private haven, a picturesque home nestled on an expansive 11-acre landscape where nature and comfort harmoniously blend. This property is perfect for buyers looking for a peaceful escape or an investment opportunity, complete with two inviting one-bedroom apartments perfect for Airbnb's to generate steady income. A wonderful family compound as well with separate areas for guests or family but easily accessible to the main house. The main living area is adorned with original woodwork and built-ins that exude timeless charm. And hardwood floors throughout. Relax and rejuvenate in the sun-drenched Florida room, a perfect spot for morning coffee or afternoon reading while basking in the natural light. The sprawling grounds feature lush meadows and a serene stream, creating an idyllic setting for outdoor activities, gardening, or simply soaking in the tranquility of nature. Located just minutes away from Jiminy Peak ski

Build to suit. This new ranch construction modular home offers an open concept kitchen, dining & living room space, The home features open, sun-filled spaces with an open floor plan that is designed to capture Pontoosuc lake and mountain views from every room on the main living level. 3 bedrooms 2 baths. Walkout lower level ready for additional finished space. Purchase as specked or chose upgrades to finish home to your desires. Lake access available within walking distance. Building plans available at request

Build to suit. This new ranch construction modular home offers an open concept on a double lot. The home features sun-filled spaces with an open floor plan that is designed to capture Pontoosuc lake and mountain views from the dinning, living & primary bedroom. 4 bedrooms 2.5 baths. Lower level ready for additional finished space. Purchase as specked or chose upgrades to finish home to your desires. Lake access available within walking distance. Building plans available at request

Build to suit. This new construction modular home offers an open concept kitchen, dining & living room space, The home features grand, open, sun-filled spaces with an open floor plan that is designed to capture Pontoosuc lake and mountain views from every room on the main living level. 4 bedrooms 3 baths. Purchase as specked or chose upgrades to finish home to your desires. Lake access available within walking distance. Building plans available at request

Charming 1930s Cape with 11 Acres of serene bliss. Welcome to your own private haven, a picturesque home nestled on an expansive 11-acre landscape where nature and comfort harmoniously blend. This property is perfect for buyers looking for a peaceful escape or an investment opportunity, complete with two inviting one-bedroom apartments perfect for Airbnb's to generate steady income. A wonderful family compound as well with separate areas for guests or family but easily accessible to the main house. The main living area is adorned with original woodwork and built-ins that exude timeless charm. And hardwood floors throughout. Relax and rejuvenate in the sun-drenched Florida room, a perfect spot for morning coffee or afternoon reading while basking in the natural light. The sprawling grounds feature lush meadows and a serene stream, creating an idyllic setting for outdoor activities, gardening, or simply soaking in the tranquility of nature. Located just minutes away from Jiminy Peak ski