Pittsfield Homes with Natural Shade Exterior Features

Pittsfield Homes with Natural Shade Exterior Features

Welcome to Pittsfield, a charming city nestled in the heart of the Berkshires in western Massachusetts. Known for its vibrant arts scene, rich history, and stunning natural landscapes, Pittsfield offers a delightful blend of urban amenities and small-town charm. With a population of around 43,000, this city is a welcoming community that boasts beautiful parks, local shops, and a variety of cultural events throughout the year. Enjoy the serene beauty of nearby lakes and mountains, perfect for outdoor enthusiasts and those seeking a peaceful retreat.

One of the standout features of homes in Pittsfield is their natural shade exterior. Many properties are adorned with lush trees and vibrant landscaping that not only enhance curb appeal but also provide a cool, inviting atmosphere. These homes often boast expansive yards, perfect for family gatherings or quiet evenings under the stars. The natural shade not only offers a respite from the summer sun but also serves as a beautiful backdrop for outdoor activities and gardening.

Imagine sipping your morning coffee on a sun-dappled porch or hosting a barbecue in a serene, shaded yard, surrounded by the sounds of nature. Homes with natural shade exterior features are not just about aesthetics; they promote a lifestyle of comfort and tranquility. In Pittsfield, you can enjoy the perfect balance of nature and community, making it an ideal place to call home. Whether you’re looking for a cozy cottage or a spacious family home, Pittsfield’s real estate market has something for everyone. Come explore the possibilities and discover your dream home in this picturesque city!

Newest Pittsfield Homes with Natural Shade Exterior Features

$485,000
4 Beds ⋅ 2 Baths ⋅ 5104770 MLS
Welcome to 23 Targhee Drive. Tucked away on 3.12 private, quiet acres this home offers the privacy you want and the convenience and access you need with three floors of efficient, usable living space. Just five minutes from downtown Pittsfield with stores, restaurants, parks, and a theatre. This house is also close to Concord which offers the amenities of a bigger city and is just 15 minutes away. Manchester is also convenient and is only 30 minutes away. This home offers 4 spacious bedrooms. There are 2 full baths, including a bedroom upstairs with its own bathroom. There is a spacious living room and dining area on the first floor which is right off the large kitchen, making entertaining convenient. The yard offers mature landscaping and a picturesque setting to enjoy all 4 seasons. There are plenty of large trees offering shade on those hot summer days. The yard is large enough to enjoy playing games outside with guests and outside entertaining and cookouts. There is a work bench in the basement to work on any projects you may have. The basement has a wood stove which will also help heat the house to keep those winter heat bills low. The heating system is forced hot water fueled by propane as well as on-demand hot water, which is also propane powered. Book your showing today.

23 Targhee Dr, 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
$899,900
3 Beds ⋅ 4 Baths ⋅ 5092220 MLS
Located just minutes from 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 easy to maintain 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 coffee or apres 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 (one with a huge walk-in closet) and a full bathroom. Both bedrooms offer plenty of space to work or study from home. Downstairs you will find a finished oasis offering a living room, bathroom, bar and an additional sleeping space. This area 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.

91 Bombadil Path, 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
$799,000
6 Beds ⋅ 4 Baths ⋅ 5079354 MLS
Price Adjustment! Endless possibilities await at 79 High Street in Pittsfield, NH, a truly unique legacy property offering exceptional flexibility and opportunity. Ideally situated in the Light Industrial/Commercial District, this remarkable property is currently configured as a three-unit building, accommodating owner-occupied living, a rental apartment, and a professional real estate office. The zoning also permits single-family residential use, making it an ideal investment for a variety of buyers. (Please refer to the attached zoning table for the complete list of permitted uses.) The impressive historic barn is a standout feature and was previously home to a successful antique business, offering incredible potential for storage, workshops, retail, studio space, or countless other ventures. The home underwent an extensive renovation in 2002–2003 and has been meticulously maintained with numerous additional improvements over the past two decades. A detailed list of updates is available in the attached documents. The expansive lot is absolutely beautiful and offers the potential for subdivision, creating even more future value. Whether you’re searching for a multi-generational property, an income-producing investment, a live/work opportunity with outstanding visibility, or a one-of-a-kind single-family home with room to grow, 79 High Street delivers unmatched versatility and endless potential.

79 High St, Pittsfield
$799,000
5077345 MLS
Price Adjustment! Exceptional opportunity to own this highly visible 4-acre property at the intersection of Route 28 and River Road in Pittsfield. Level, high and dry, this open parcel offers outstanding exposure and endless potential with Light Industrial/Commercial zoning and grandfathered three-unit mixed-use status. Currently configured as a spacious 4+ bedroom home with two attached rental units, one apartment and one professional office, it offers flexibility for owner-occupancy, rental income, or business use. The impressive barn features over 3,000 square feet on two full floors, plus a loft and full basement, providing incredible space for storage, retail, workshop, or light industrial uses. Meticulously maintained and updated over the past 25 years, the property is ready for its next owner. The land was previously subdivided into three lots, and the current owners have also explored a two-lot subdivision, with both survey plans available. Whether you’re looking to operate a business, generate rental income, develop the property, or create the ultimate live/work setting, this unique offering presents endless possibilities. Properties with this combination of location, zoning, and versatility rarely come to market.

79 High St, Pittsfield
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