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

$449,000

5107423 MLS

Great investment opportunity in the heart of Pittsfield! This historic multi-family property, originally built in 1850, offers character, flexibility, and excellent potential for an investor or owner-occupant. Each unit features its own kitchen and living area, along with two bedrooms and a full and a 1/2 bath, plus air conditioning, providing comfortable and functional layouts for tenants or extended family. Recent updates include mini-split systems, offering added peace of mind and energy-efficient heating and cooling. With its historic character, versatile floor plan, and two-bedroom units, this property presents an excellent opportunity to build equity and generate rental income. Zoned Commercial/Light Industrial, you could also use the property for another use with high visibility. Whether you’re expanding your investment portfolio or looking for a property with income potential, this Pittsfield multi-family is worth a look!

15 Leavitt Rd, Pittsfield

$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

$420,000

3 Beds ⋅ 2 Baths ⋅ 5101870 MLS

This well-maintained ranch has been owned by the same family for over 60 years! Great location in a neighborhood close to town and major routes. 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

$599,900

3 Beds ⋅ 1 Baths ⋅ 5094594 MLS

A distinctive Vermont log home with space, privacy, and year-round versatility just 15 minutes from Killington. Set on 1.3 wooded acres in Pittsfield, this 3 bedroom, 1-bath home centers around a dramatic great room with cathedral ceilings, exposed beams, warm wood interiors, and a wood stove. A natural gathering space after a day on the mountain or simply at the end of the day. Thoughtfully expanded with a 1998 addition and well maintained over the years, the home offers an oversized heated two-car garage, standing-seam roof, EC Fiber high-speed internet, generator hookup, central vacuum, and Efficiency Vermont insulation improvements. These are the practical features that make Vermont living easier in every season. Step outside to a covered porch or the expansive rear deck with retractable awning, with room for summer dinners, a quiet morning outdoors, or an evening surrounded by mature trees and seasonal mountain views. Established landscaping and lawn complement the privacy of the wooded 1.3 acre setting. The full walkout basement spans both sections of the home, adding substantial workshop, storage, and laundry space, rough plumbing for a future bath, and two walkout entrances. Skis, bikes, outdoor gear, projects and hobbies all have a place here. Four-season recreation is close at hand: approximately 15 minutes to Killington, 20 minutes to Pico, 10 minutes to Pittsfield Village, 30 minutes to Woodstock, and 35 minutes to Rutland. Whether home is where you spend every day or where you come to get away, this is a place with room to gather, work, unwind, and enjoy Vermont in every season.

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

$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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