Pittsfield Homes with Separate Dining Room Interior Features

Welcome to Pittsfield, a charming city nestled in the heart of the Berkshires in Massachusetts. Known for its rich history, vibrant arts scene, and stunning natural beauty, Pittsfield offers a unique blend of urban convenience and rural tranquility. The city is surrounded by picturesque mountains, pristine lakes, and scenic parks, making it an ideal destination for outdoor enthusiasts and culture lovers alike. With a thriving downtown area filled with eclectic shops, delightful eateries, and cultural venues like the Berkshire Museum and the Colonial Theatre, Pittsfield is a place where community and creativity flourish.

When it comes to finding your dream home in Pittsfield, look no further than the delightful residences featuring separate dining rooms. These homes are designed with an emphasis on both functionality and elegance, providing the perfect setting for family gatherings, dinner parties, or intimate meals. The separate dining room interior feature allows for a designated space that enhances the dining experience, making every meal feel special. Imagine hosting holiday feasts or casual get-togethers in a beautifully appointed dining room, complete with ample natural light and charming architectural details.

The homes in Pittsfield with separate dining rooms not only offer a place to enjoy meals but also serve as a versatile space for entertaining or relaxing with loved ones. Whether you prefer a classic, traditional design or a more contemporary aesthetic, Pittsfield's real estate market has a variety of options to suit your taste. Explore the inviting neighborhoods and discover the perfect home that embodies the warmth and character of this incredible city. Welcome to Pittsfield, where your dream home awaits!

Newest Pittsfield Homes with Separate Dining Room Interior Features

$479,000

3 Beds ⋅ 3 Baths ⋅ 5105259 MLS

Nestled among the woods of Pittsfield's coveted Townsend Brook area, this beautifully maintained and thoughtfully updated chalet captures the essence of the quintessential Vermont mountain getaway. Designed in the tradition of a European alpine chalet, the main living level occupies the second floor, maximizing natural light and creating a warm, inviting space for après-ski gatherings or quiet evenings by the fire. Recent improvements include an upper-level bump-out with a charming reading nook and convenient powder room, beautiful maple hardwood floors, modern lighting and ceiling fans, and beautifully remodeled bathrooms. An enclosed former storage shed has been transformed into a generous mudroom and first-floor laundry, complete with a wall of built-in cabinetry for skis, bikes, boots, and outdoor gear. A spacious wraparound deck extends the living space outdoors, offering both sunny and shaded spots for morning coffee, al fresco dining, or gathering with friends. Surrounded by the Green Mountains, miles of mountain biking and snowmobile trails are practically at your doorstep, while world-class skiing at Killington and Pico is just minutes away. With easy access from Montreal, Boston, and New York City, this turnkey retreat offers an appealing combination of comfort, recreation, and value - equally suited to weekend escapes, investment income, or year-round living.

253 Lookout Rd, Pittsfield

$1,300,000

3 Beds ⋅ 4 Baths ⋅ 5099336 MLS

Escape to your own slice of New Hampshire paradise with this beautifully maintained Cape Cod home, nestled on 7.36 scenic acres of rolling fields, mature woods, and abundant wildlife. Offering the perfect balance of privacy, functionality, and timeless charm, this exceptional property is ideal for those seeking peaceful country living without sacrificing modern conveniences. Built in 2003 and on the market for the first time, this thoughtfully designed home welcomes you with a bright foyer, warm natural woodwork, and sun-filled living spaces. The spacious living room features a cozy wood stove, creating the perfect gathering place during New England winters, while the formal dining room offers an inviting space for entertaining family and friends. The heart of the home is the well-appointed kitchen, complete with an oversized center island, breakfast nook, built-in oven, electric glass range, and ample workspace for everyday living or holiday gatherings. The warm, custom hickory cabinetry offers both beauty and functionality, featuring deep pot-and-pan drawers, convenient pull-out spice racks, and a full-height pantry with easy-access sliding shelves. The home features three generously sized bedrooms and four bathrooms, including a private primary suite with an en-suite bath and walk-in closet. An additional guest or in-law suite provides outstanding flexibility for multi-generational living, extended family, visitors or additional income. The walk-out basement offers abundant storage and future expansion potential, while the in-law apartment offers accessibility features including a vertical elevator lift, hard-surface flooring, grab bars, and an accessible washer and drye enhance convenience and comfort. Car enthusiasts, hobbyists, or business owners will appreciate the impressive heated five-car attached garage with direct access and automatic garage door openers, providing exceptional storage and workspace year round.

50 Range Rd, Pittsfield

$499,900

3 Beds ⋅ 1 Baths ⋅ 5098986 MLS

*MOTIVATED SELLERS* Open House: Saturday, Aug. 22: 10am-12pm! Unique, seasonal waterfront cottage on one of NH's best-kept secrets! Tucked along the shores of exclusive Wild Goose Pond (spanning Strafford & Pittsfield) this one-of-a-kind cottage is the quintessential NH lakefront retreat. Coffee on the deck leads to long summer days on the water! 208' of water frontage, this property was made for making memories! Unlike anything else on the pond, this distinctive cottage embraces camp life with open-concept living, warm pine plank walls, tavern-style lighting & slate wood stove that warms the living room, perfect for cool evenings after a day on the water. Sun-filled 1st-floor primary bedroom features pine walls & ceiling, transom windows, the added convenience of an attached laundry area, and a slider to the lovely water view deck. Automatic awning provides welcomed deck shade while you relax & soak in the peaceful setting. Kitchen offers a generous walk-in pantry, and the adjoining sunroom is the perfect place to unwind by the cozy propane fireplace & enjoy a puzzle, watching nature unfold outside. 2nd & 3rd floor sleeping lofts feel like you're tucked in a treehouse! Drift off to the calls of loons, and wake to astonishing views. Outside, a beautifully crafted outdoor kitchen with brick masonry built-in grill overlooks the beach & sparkling waterfront, the perfect space for summer cookouts. Incredible outdoor shower offers a private place to rinse off- a luxury that perfectly captures the lake lifestyle. Spend your days boating, swimming, kayaking, paddling, or fishing from the newly installed aluminum dock with swim ladder. Wild Goose Pond allows motorized boats while maintaining a peaceful atmosphere that has made it one of NH's hidden gems. Property in Strafford & Pittsfield, MLS#5098986+5098984). If your dream is a seasonal waterfront escape where every weekend feels like vacation, this unforgettable Wild Goose Pond cottage is for you! Sold Furnished!

149 Merrill Rd, Pittsfield

$745,000

3 Beds ⋅ 2 Baths ⋅ 5097001 MLS

Tucked away at the end of Upper Michigan Road on 54.4 private acres bordering the Green Mountain National Forest, this remarkable 1825 Vermont farmhouse offers breathtaking long-range mountain views in an unforgettable setting. Rich in authentic character, the home showcases rustic knotty pine walls, exposed hand-hewn beams, wide plank floors, and a fieldstone fireplace hearth. The home's low ceilings and gently uneven floors are not imperfections — they are reminders of a time when homes were built by hand and meant to last. A thoughtfully designed addition in 1996 blends seamlessly with the original home, providing modern comfort with a spacious primary bedroom featuring 10-foot ceilings and custom built-ins, a guest bedroom, and a beautifully updated full bath. The expansive living area offers inviting spaces to gather around the woodstove, enjoy movie nights, or relax with family and friends. The vintage-inspired kitchen and dining area, with vaulted ceilings, warm pine finishes, and a picnic-style dining table, is ideal for casual entertaining. Upstairs, two additional guest bedrooms and a powder room provide comfortable accommodations. Outside, more than 30 acres of managed woodland extend along both sides of the town road, complemented by open lawns, mature perennial gardens, and endless opportunities to enjoy the spectacular southern views. A detached two-car garage with overhead storage provides ample space for vehicles and outdoor gear. Snowmobiling, ATV riding, hiking, mountain biking, and snowshoeing are all accessible directly from the property. A state wastewater permit for an additional three-bedroom home offers exceptional flexibility for future expansion or a family compound. This is a rare opportunity to own a legacy Vermont property where history, privacy, recreation, and extraordinary natural beauty come together.

2238 Upper Michigan, Pittsfield

$950,000

3 Beds ⋅ 4 Baths ⋅ 5092220 MLS

Located just 7 miles to the Killington Access Road, 91 Bombadil Path offers the perfect blend of convenience, quality, square footage and comfort. This one owner, well maintained home offers easy access to the VAST trail. Situated on 3.84 acres this Cape presents peaceful gardens with mature perennial plants and a patio great for entertaining around the firepit. Park your vehicles in the attached, oversized garage which also includes overhead storage. Enter the home into a dedicated mudroom. If cooking is your thing you will love the natural light in the open concept kitchen featuring stainless steel appliances. Enjoy morning coffee in the 3 season sun porch. Relax in the spacious living room by the gas fireplace offering calming ambience. The generously sized primary suite complete with walk in closet, a 2 sink countertop, soaking tub and seperate shower is the perfect place to retreat to at the end of an adventurous day. The laundry room consists of a full sized washer and dryer, built in wall ironing board and wash sink, making laundry a breeze. Upstairs you will find 2 large bedrooms and a full bathroom. Both bedrooms offer plenty of space to work or study from home. Downstairs you will find a finished area offering an additional living room, bathroom, bar and bonus room. This space has its own entrance making it a perfect in-law suite or rental apartment. Downstairs you will also find a craft room, tool/ski tuning room, and plenty of storage space. Located just minutes to Killington, Pittsfield offers their students school choice, making this home even more desirable. Store your equipment, whether it is for gardening, snowmobiling or skiing in one of the 2 sheds. With plenty of parking, this home is perfect for a primary residence, a vacation home or an investment opportunity. Located on a cul-de-sac, this home offers beautiful winter mountain views. Near skiing, snowmobiling and hiking. Paradise awaits. Schedule your showing today.

91 Bombadil Path, Pittsfield

$799,000

4 Beds ⋅ 3 Baths ⋅ 5091752 MLS

Have you been dreaming about Building a home but didn't want to wait so long while it was under construction? Do not miss your opportunity to make this home your own as the Builder is estimating around 90 days from Buyer Selections for completion. Right now, there is still time to choose finishes including siding, decking color, flooring, cabinets, countertops, paint etc. Located on a quiet country road and nestled into a private setting in the woods. Features & Specs also include allowances which allow for hardwood and tile throughout and Granite countertops. Open first floor layout with formal dining and fireplace in the living room. Upstairs there are 3 secondary bedrooms, full bath, laundry and a Fabulous Master Primary suite with its own private bath and Walkin closet. Home also offers a covered front porch and back deck with composite decking and vinyl rails. Central AC also included in current pricing. Attached 2 car garage with direct entry into the home and single door to access outside. Please do not go onsite unattended, you need to schedule a showing before going onto the property.

7 Shaw Rd, Pittsfield

$799,000

4 Beds ⋅ 4 Baths ⋅ 5081561 MLS

Oh the Views! Perfectly sited, this Quintessential 1780 Colonial Farmhouse is framed by lovely landscaping & timeless New England charm. This exceptional homestead includes two separate parcels: 4.5 country acres surrounding the home plus an additional 3.06 acres w/ vintage barn just across the street. Brimming with charm & character, this expansive home has been thoughtfully updated & improved throughout. The 4 season porch serves as an ideal mudroom & a welcoming place to unwind. A recently renovated kitchen features new appliances, cabinetry & quartz countertops, and open seamlessly to a sun-filled family room with informal dining and scenic backyard views. The main level also offers a classic dining room, living room, private office (or potential bedroom), fully bath, second mudroom, and a pantry/canning area leading to the carriage house & bonus room. Upstairs, you'll find a spacious primary suite, a 2nd ensuite bedroom, a 3rd bedroom & bath, and a sunlit office or 4th bedroom. Additional highlights include abundant closet space, a convenient laundry area & charming front & back staircases. Beautiful details shine throughout - moldings, wide pine floors and a blend of informal living spaces across 4,156 sq ft. The carriage house/garage offers ample space for vehicles, a workshop & future expansion. This property has been meticulously maintained w/updated systems. Step outside from the family room onto a charming stone patio overlooking "froggy pond", gardens, red maples, fruit trees & more. The vintage barn, sold "as is" offers incredible potential is sited on the separate parcel. With endless possibilities, farm equestrian property, multigenerational home, ADU, Bed & Breakfast, event venue - this peaceful and picturesque homestead is ideal for living, working and playing.

1310 & 1311 Upper City, Pittsfield

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