Pittsfield Homes with Garden Exterior 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 small-town charm. With its picturesque parks, scenic hiking trails, and cultural attractions, it’s no wonder that Pittsfield has become a sought-after destination for families, professionals, and retirees alike.

One of the standout features of homes in Pittsfield is their beautiful garden exteriors. Imagine coming home to a property that not only offers cozy interiors but also boasts lush gardens that bloom with vibrant colors throughout the seasons. Many homes in the area are designed with thoughtfully landscaped yards, providing the perfect backdrop for outdoor gatherings, family barbecues, or a quiet evening under the stars.

From quaint cottages with charming flower beds to spacious family homes with expansive gardens, Pittsfield’s real estate market has something for everyone. Whether you’re a gardening enthusiast eager to cultivate your own vegetable patch or someone who simply enjoys the tranquility of a well-maintained yard, these homes with garden exterior features are truly a dream come true.

In addition to their aesthetic appeal, these gardens often enhance the overall quality of life, offering a serene escape from the hustle and bustle of daily life. With Pittsfield’s rich community spirit and access to nature, you’ll find that a home with a garden here is not just a residence but a lifestyle choice that invites you to connect with nature and your neighbors. Come explore the possibilities that await you in beautiful Pittsfield!

Newest Pittsfield Homes with Garden Exterior Features

$499,000

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

$450,000

3 Beds ⋅ 2 Baths ⋅ 5101870 MLS

Rare opportunity! This well-maintained ranch has been owned by the same family for over 60 years and is located in Pittsfield's Light Industrial/Commercial District. The property offers exceptional flexibility for entrepreneurs, contractors or buyers seeking a live/work opportunity. Whether you are looking for a primary residence with business potential or a property with future commercial possibilities, this property offers you all of that! The first floor features beautiful hardwood floors, large front living room, dining room, 3 season room with root cellar, 3+ bedrooms, 2 baths and an egress to the oversized one stall garage. Great flex space in the lower level with playroom, laundry room, utility room, 3/4 bath and 3 guest rooms or offices. The most AMAZING yard with vegetable and perennial gardens, fruit trees, out building and is partially fenced in. Proudly owned and meticulously cared for, this home is ready for its next chapter. Quick close is possible!

12 Norris Rd, Pittsfield

$619,900

3 Beds ⋅ 1 Baths ⋅ 5094594 MLS

**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

$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

$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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