Pittsfield Homes with Covered Porch Exterior Features

Welcome to Pittsfield, Massachusetts—a charming city nestled in the heart of the Berkshires, known for its rich history, vibrant arts scene, and stunning natural beauty. With its picturesque landscapes and friendly community, Pittsfield offers a unique blend of small-town charm and urban conveniences. Residents enjoy a variety of cultural experiences, from the renowned Barrington Stage Company to the serene beauty of the nearby Berkshire Mountains. Outdoor enthusiasts will find a plethora of recreational activities, including hiking, biking, and fishing in the area's pristine parks and lakes.

One of the standout features of homes in Pittsfield is the beloved covered porch. These inviting exterior spaces offer the perfect spot to unwind with a book, sip your morning coffee, or enjoy warm summer evenings with friends and family. A covered porch not only enhances the aesthetic appeal of a home but also provides a functional outdoor living area that can be enjoyed year-round, sheltered from the elements.

Imagine stepping out onto your covered porch, where you can take in the sights and sounds of this vibrant community. Whether you’re hosting a summer barbecue or simply enjoying a quiet moment with nature, these porches create a seamless transition between indoor and outdoor living. In Pittsfield, homes with covered porch features are more than just a design element; they are an invitation to embrace the lifestyle of this beautiful city.

Explore the diverse real estate options in Pittsfield and discover your dream home with a welcoming covered porch, where cherished memories are waiting to be made.

Newest Pittsfield Homes with Covered Porch Exterior Features

$319,900

2 Beds ⋅ 2 Baths ⋅ 5106327 MLS

BRAND NEW AND AFFORDABLE HOME! Keep your costs low and comfort level high! Two bedroom, two bath, single family residence on its own land, just finished. Super efficient Bosch heat pump with LP Gas assist and whole house AC. Fully applianced eat-in kitchen has fridge, electric range, microwave, and dishwasher. Upstairs full bath has stacked LG washer/dryer. Fully foam insulated for heat/cooling savings and noise cancellation. Situated on a small in-town lot within walking distance of all village amenities has municipal water and sewer. Parking for up to 5 cars.

4 Marshall Ct, Pittsfield

$619,900

3 Beds ⋅ 1 Baths ⋅ 5094594 MLS

OPEN HOUSE! AUGUST 22 from 11am-2pm! Your Vermont retreat begins where the ski day ends.** Enjoy everything Killington and Pico have to offer while coming home to the privacy and peace of 1.3 wooded acres in the welcoming town of Pittsfield. Beautifully maintained and thoughtfully expanded, this inviting Vermont log home offers the perfect balance of year round recreation and everyday living. With easy access to hiking, mountain biking, golf, and endless outdoor adventure, it's easy to see why the home was previously enjoyed as a successful ski-season retreat. 3 bedrooms. 1 full bath. Heated oversized two-car garage. Warm wood interiors. Dramatic cathedral ceilings. Open concept living. Wood stove. Standing seam roof. EC Fiber high speed internet. Central vacuum. Generator hookup. Efficiency Vermont insulation improvements. Covered porch mornings. Gatherings on the expansive rear deck beneath the retractable awning. Wildlife at your doorstep. Mature trees. Seasonal mountain views. The full walkout basement spans both sections of the home, offering workshop space, abundant storage, laundry, rough plumbing for a future bath, and two walkout entrances. deal for storing skis, bikes, outdoor gear, hobbies, or future expansion. 15 minutes to Killington. 20 minutes to Pico. 10 minutes to Pittsfield Village. 30 minutes to Woodstock. 35 minutes to Rutland. Whether you're looking for a primary residence, a four-season retreat, or a peaceful Vermont getaway, this home is ready to be enjoyed in every season. To help buyers envision the home through their own personal style, select interior photographs are shown both as currently furnished and virtually staged.

221 Fiddlehead Ln, 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

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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