Pittsfield Homes with Deck Exterior Features

Welcome to Pittsfield, Massachusetts—a charming city nestled in the heart of the Berkshires. Known for its vibrant arts scene and rich history, Pittsfield offers a unique blend of urban living and natural beauty. With its picturesque parks, historic architecture, and an array of cultural activities, it’s no wonder that this city is a sought-after destination for homebuyers.

Pittsfield is surrounded by stunning landscapes, making it an ideal location for outdoor enthusiasts. The nearby Berkshire Mountains provide ample opportunities for hiking, skiing, and exploring nature. The city is also home to several beautiful parks, including the expansive Burbank Park and the scenic Pittsfield State Forest, ensuring that residents have plenty of green spaces to enjoy.

When it comes to real estate, Pittsfield boasts a variety of homes that cater to diverse tastes and lifestyles. One of the standout features of many properties in the area is the presence of homes with deck exterior features. Imagine sipping your morning coffee or hosting a summer barbecue on your own private deck, surrounded by the beauty of nature. These outdoor spaces not only enhance your living experience but also provide a perfect setting for entertaining friends and family.

Whether you’re looking for a cozy cottage or a spacious family home, Pittsfield’s real estate market offers a range of options with stunning deck features that invite you to embrace the outdoors. Discover the charm of Pittsfield and find your dream home that perfectly blends comfort, style, and the beauty of the Berkshires. Your new life awaits in this delightful city!

Newest Pittsfield Homes with Deck Exterior Features

$539,900

3 Beds ⋅ 2 Baths ⋅ 5107431 MLS

Welcome to 7 True Road in Pittsfield! This inviting 3-bedroom, 2-bath home offers 1,700+ square feet of living space and a comfortable, versatile layout designed for everyday living. The kitchen has plenty of counter and storage space for cooking and entertaining. There is a dedicated laundry room, as well as a flexible office or mudroom space. The home is filled with windows, allowing natural light and the beautiful setting to shine throughout. The main floor features a spacious bedroom and full bathroom, offering convenient one-level living and the flexibility to make this your forever home. Upstairs, two additional generously sized bedrooms provide plenty of space, plus an additional full bath. There is also ample closet and storage space throughout the home, including the large walk-out basement with a garage, workshop, and bonus room space. Outside, you can enjoy the 3.62 acres from the beautiful wraparound porch. There is also a shed and two carports to store all your outdoor toys and equipment. The home is set toward the back of the property, offering wonderful privacy, with a nice mix of wooded areas and open space. Join us for the open houses: Friday, 9/4 | 6–8 PM Saturday, 9/5 | 10 AM–12 PM

7 True Rd, Pittsfield

$300,000

3 Beds ⋅ 2 Baths ⋅ 5106738 MLS

Under contract but will continue to show. Welcome to 28 South Main Street in Pittsfield, NH! This charming 3 bedroom, 2 bath Cape sits high on .47 acres and offers a wonderful opportunity for those looking to start out, settle down, or downsize. Filled with character and warmth, the home features hardwood floors in the living room and a woodstove to take the chill off on those cold New Hampshire nights. The first floor offers a comfortable bedroom, renovated bath, dining room, kitchen, and a convenient laundry room that doubles as a pantry. Enjoy the sunshine and fresh air from the inviting 3 season porch, with two exterior decks providing plenty of space for relaxing, entertaining, or simply enjoying the outdoors. Upstairs, you'll find two additional bedrooms and a 3/4 bath. The full walk-out basement adds valuable space and flexibility, whether you envision a workshop, home gym, hobby area, or additional storage. Outside, there's a handy shed for your gardening and outdoor tools, along with a patio area just off the deck. Recent updates include a new heating system, replacement windows on the first floor, renovated bathrooms, and a nicely paved driveway. Conveniently located close to the amenities of downtown Pittsfield while offering a comfortable setting to call home, this is one you'll want to see!

28 S Main St, Pittsfield

$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

$559,000

5 Beds ⋅ 3 Baths ⋅ 5099518 MLS

Located in the heart of central Vermont, this fully furnished and equipped five-bedroom home provides convenient access to Killington Resort and nearby snowmobile trails, making it an ideal choice for skiers, mountain bikers, hikers, golfers, and outdoor enthusiasts alike. With an established rental history, it also presents an excellent opportunity as a vacation home with income potential. Inside, the home has a warm and welcoming atmosphere, with a cozy propane fireplace serving as the centerpiece for relaxing after a day outdoors. The comfortable kitchen and living area create an inviting space to gather with family and friends, while the five-bedroom layout offers plenty of room for guests, multiple families, or a dedicated home office. After a day on the slopes or the trails, unwind in the hot tub or head into the charming town of Woodstock to enjoy local restaurants, shopping, and classic Vermont character. Whether you're looking for outdoor adventure, a peaceful weekend getaway, or an investment property, this home provides easy access to many of the region's most popular attractions. With its flexible layout, proven rental appeal, and prime location in the Green Mountains, 89 Townsend Brook Road is ready for its next chapter. Call today for more details or to schedule a private showing.

89 Townsend Brook 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

$599,900

3 Beds ⋅ 1 Baths ⋅ 5094594 MLS

NOW $599,900 A NEW PRICE POINT. YOUR VERMONT RETREAT MAY HAVE JUST COME INTO VIEW. It 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

$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 ⋅ 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

$689,900

3 Beds ⋅ 3 Baths ⋅ 5087082 MLS

Check out this new Colonial home, presently under construction, sitting on 2.81 level acres with open fields and a wooded backyard in a quiet area of Pittsfield. This bright and cheery home features an attached 2-car garage with auto openers that leads into a half bath with laundry. The open kitchen and dining area comes fully applianced with white cabinets, under-counter lighting, granite counters, and a breakfast bar that opens to a dining nook and a back deck overlooking the field. The front of the home offers a large living room and family room with a partially open stairway featuring wood treads. The second floor includes a primary bedroom with an en-suite bath featuring double sinks and a large walk-in closet, along with two additional bedrooms and a full bath. Additionally, there is a full basement offering great potential for future expansion. Some facsimile photos used to show finished project

85 Fairview Dr, Pittsfield

$1,890,000

3 Beds ⋅ 2 Baths ⋅ 5086512 MLS

Looking for the family compound? Here is your chance, 2 post and beam buildings, the main house and the other completed but would need to be hooked into well and septic. Set in the country, with open fields and woodlands with miles of trails meandering through untouched hardwood forest, down to historic spring fed Wild Goose Pond. Over 300 feet of owned waterfront on this quiet, peaceful, private lake, where loons gather and the fishing is incredible. Take the kayak out for a paddle to watch the sunset and you may encounter a curious loon, kingfishers, eagles, and hawks. Included with this remarkable property you will discover two stunning post and beam buildings, each with attached 2 car garage. Moving along down the paved driveway towards the back of the main house you will find a 3-room barn with one stall and storage area for hay and equipment and an additional 10 x 20-foot run-in shelter in the field behind the barn. A separate greenhouse, a waterfall garden and Koi Pond, a separate irrigation well and sprinkler system, and extensive rock wall landscaping. (see attachments re: each homes features) Centrally located in the lakes region, 30 minutes from Concord, 45 minutes from Portsmouth and just 1.5 hours from Boston. Presently a business running from 2nd post and beam, but offers so much more for the outdoor enthusiast, tell us your story.

490 Clough Rd, Pittsfield

$315,000

3 Beds ⋅ 1 Baths ⋅ 5082428 MLS

Back on market with no fault to the sellers! Welcome to this charming and affordable 3-bedroom, 1-bath single-family home in the heart of Pittsfield! Priced attractively at $315,000, this home offers a wonderful opportunity to own a property full of character while still leaving room to make it your own. Inside, you’ll find a warm and inviting layout with plenty of space to spread out, along with thoughtful updates completed over the years that add comfort and functionality. The home’s classic charm shines through, offering a cozy and welcoming atmosphere. Step outside to enjoy the fenced-in backyard—perfect for outdoor gatherings, pets, or simply relaxing in your own private space. Location is key, and this home delivers. Conveniently situated 15 minutes to downtown Concord, and within walking distance to downtown Pittsfield, you’ll have easy access to local shops, the grocery store, and several restaurants, making everyday living both simple and enjoyable. Whether you’re looking for your first home, downsizing, or seeking a property with great value and potential, this Pittsfield gem is one you won’t want to miss!

23 Concord Hill 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

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