Pittsfield Real Estate

Welcome to Pittsfield, Massachusetts—a charming city nestled in the heart of the Berkshires, where natural beauty meets rich cultural heritage. Known as the "Heart of the Berkshires," Pittsfield is surrounded by rolling hills, lush forests, and pristine lakes, making it an outdoor enthusiast’s paradise. Whether you enjoy hiking, biking, or simply soaking in the stunning vistas, this city offers ample opportunities to connect with nature.

Pittsfield boasts a vibrant downtown area filled with eclectic shops, delightful eateries, and cultural attractions. The historic Colonial Theatre hosts a variety of performances, from Broadway shows to local productions, ensuring that there’s always something exciting happening. Art lovers will appreciate the Berkshire Museum and the numerous galleries showcasing local talent.

The city is also home to several parks and recreational areas, including the beautiful Burbank Park and the serene Onota Lake, perfect for picnics, fishing, and family outings. For those who enjoy winter sports, nearby ski resorts offer thrilling slopes and cozy lodges.

Pittsfield is not just about natural beauty and culture; it’s also a community that values education and growth. The city is served by quality schools and institutions, making it an ideal place for families. With a strong sense of community and a welcoming atmosphere, Pittsfield is a place where neighbors become friends.

Whether you’re looking to buy a home, invest in property, or simply explore, Pittsfield offers an irresistible blend of charm, opportunity, and a lifestyle that many dream of. Discover the heart of the Berkshires and see why Pittsfield is the perfect place to call home!

Newest Listings in Pittsfield

$474,900

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. Showings begin immediately so don't wait and a quick close is possible!

12 Norris Rd, Pittsfield

$295,900

2 Beds ⋅ 1 Baths ⋅ 5100391 MLS

This charming, remodeled New Englander offers a spacious 1,450+-square-foot layout featuring two upstairs bedrooms, a family room, an oversized first-floor bathroom, and a large kitchen with stainless steel appliances. Located in the heart of historic Pittsfield, New Hampshire, the property blends small-town community charm with excellent access to nearby rivers, local recreation ponds and a waterfall offering peaceful daily walking routes. Jenness Pond & Wild Goose Pond: Local freshwater bodies ideal for quick swimming, kayaking, and fishing trips. Bear Brook State Park: A massive nearby reservation providing extensive hiking, biking, camping, and swimming options. True New England living at it's best.

23 Watson St, Pittsfield

$159,900

5099813 MLS

Escape to your own piece of New Hampshire! Nestled on 35.17± private acres, this wooded lot offers the privacy you've been searching for while keeping you close to everyday conveniences and commuter routes. It's has great potential for a very private setting to build your dream home, explore the outdoors, and enjoy the peace and beauty of nature. If you've been dreaming of a place to truly relax, this property deserves a closer look. Located on a shared cost between land owners to the privately maintained road.

Lot 11 True, Pittsfield

$575,000

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

$589,900

3 Beds ⋅ 1 Baths ⋅ 5098986 MLS

Seasonal waterfront cottage on one of NH's best-kept secrets! Tucked along the shores of exclusive Wild Goose Pond (spanning Strafford & Pittsfield) this one-of-a-kind contemporary cottage is the quintessential NH lakefront retreat. Coffee on the deck leads to long summer days on the water- with 208' of water frontage, this property was made for making memories! Unlike anything else on the pond, this distinctive cottage embraces the spirit of camp life with open-concept living, warm pine plank walls, tavern-style lighting, and slate wood stove that warms the living room, perfect for cool evenings after a day on the water. Sun-filled 1st-floor primary bedroom features pine walls & ceiling, transom windows, the added convenience of an attached laundry area, and a slider to the lovely water view deck. Automatic awning provides welcomed deck shade while you relax & soak in the peaceful setting. The kitchen offers a generous walk-in pantry, and the adjoining sunroom is the perfect place to unwind by the cozy propane fireplace & enjoy a puzzle, watching nature unfold outside. Ladders lead to the 2nd & 3rd floor sleeping lofts, where you'll feel like you're tucked in a treehouse! Drift off to the calls of loons, and wake to astonishing views. Outside, a beautifully crafted outdoor kitchen with brick masonry built-in grill overlooks the beach & sparkling waterfront, the perfect space for summer cookouts. Incredible outdoor shower offers a private place to rinse off- a luxury that perfectly captures the lake lifestyle. Spend your days boating, swimming, kayaking, paddling, or fishing from the newly installed aluminum dock with swim ladder. Wild Goose Pond allows motorized boats while maintaining a peaceful atmosphere that has made it one of NH's hidden gems. Property in Strafford & Pittsfield, MLS#5098986+5098984). If your dream is a seasonal waterfront escape where every weekend feels like vacation, this unforgettable Wild Goose Pond cottage is for you! Sold Furnished!

149 Merrill Rd, Pittsfield

$175,000

1 Beds ⋅ 1 Baths ⋅ 5097271 MLS

Enjoy Vermont living and four-season recreation from this spacious first-floor, one-bedroom condo in the Wintergreen complex. Whether you're looking for a weekend retreat, investment opportunity, or affordable home base near the mountains, this unit offers comfort, convenience, and flexibility. The open-concept floor plan creates a bright and inviting living space, with the kitchen, dining, and living areas all connected for easy everyday living. A cozy woodstove serves as the focal point of the living room, providing warmth after a day of outdoor adventure. Offered fully furnished, this condo is ready to enjoy from day one. Step outside and you'll appreciate the dedicated storage closet for skis, snowboards, and seasonal gear, along with covered firewood storage to keep you stocked for Vermont's cooler months. Residents also enjoy access to on-site laundry facilities for added convenience. Located just minutes from Killington and within easy reach of Pico, this property offers outstanding access to year-round recreation. Spend your days skiing, snowmobiling, hiking, biking, or kayaking, then head to nearby restaurants, shops, and local gathering spots. With no rental restrictions, this property offers excellent flexibility for personal use, short-term rentals, long-term rentals, or a combination of both. Its location, practical amenities, and proximity to some of Vermont's best outdoor recreation make it an excellent option for a mountain getaway, full-time residence, or investment property.

2358 Rte 100, Unit 102, 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

$849,900

4 Beds ⋅ 4 Baths ⋅ 5095957 MLS

We will continue to show for back-up offers! Welcome to this beautiful home where privacy, space, and versatility come together on over 13 beautiful acres with two Lots of Record. Surrounded by open fields and peaceful country views, this property offers the perfect blend of modern updates and rural charm. Over the past two years, extensive improvements have transformed the home, including a stunning new kitchen, drilled well, siding, windows, doors, and an expansive Trex deck. The heart of the main home is the beautifully designed kitchen featuring leathered granite countertops, an abundance of stylish cabinetry, a center island, dining area with additional built-ins, and warm birch flooring. The oversized living room provides plenty of space for gathering, highlighted by a brick hearth for a woodstove, beech flooring, and two new sliding doors that open to the side and rear decks—ideal for entertaining or simply enjoying the serenity and privacy of the surrounding landscape. Relax on the classic covered front porch overlooking the beautifully landscaped yard. Upstairs, you'll find three bedrooms with hardwood floors, including a spacious primary suite with a walk-in closet and private full bath, along with a second full bathroom. The walk-out lower level offers additional flexibility with a finished room (currently unheated) and ample space for a home gym, workshop, or storage. Need room for extended family or guests? The attached accessory dwelling unit (ADU) provides exceptional multi-generational living opportunities, complete with a full eat-in kitchen, living room, ¾ bath, and a second-floor bedroom with a walk-in closet. A detached three-car garage, paved driveway, and whole-house generator complete this exceptional property. If you've been searching for acreage, privacy, and flexible living space with numerous recent updates, 592 Tilton Hill Road is ready to welcome you home. Showings by appt. Listing Agent is related to Sellers.

592 Tilton Hill Rd, Pittsfield

$449,000

6 Beds ⋅ 4 Baths ⋅ 5095878 MLS

Hidden away on a quiet dirt road in the heart of Pittsfield, this charming 6-bedroom chalet offers privacy, character, and endless potential. Surrounded by Vermont's natural beauty, you'll enjoy easy access to nearby hiking, biking, and snowmobile trails, while being just 20 minutes from Killington Resort. The home features three levels of living space, two cozy fireplaces/woodstoves, and an expansive deck accessed through two sets of sliding glass doors perfect for enjoying summer evenings in the mountains. With a classic 1965 chalet design and a fun 1970s-inspired aesthetic already in place, this property is ready for its next owner to embrace its vintage charm or bring it to the next level with light to moderate updates. Flat driveway that can fit 6 cars comfortably. Whether you're searching for a spacious country retreat, a vacation getaway, or an investment property with strong ski-rental potential, this secluded mountain home offers a rare opportunity to create something special. Enjoy the peace and privacy of a setting where neighbors are out of sight and nature takes center stage.

153 Eagle Rock 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

$550,000

4 Beds ⋅ 3 Baths ⋅ 5093979 MLS

Experience the perfect blend of privacy, modern updates, and country living at this beautifully maintained 4-bedroom home set on a scenic lot with stunning mountain views. Thoughtfully updated throughout, the home features a completely renovated kitchen completed in 2023 with white cabinetry, quartz countertops, a striking 12-foot center island, stainless steel appliances, and a stylish subway tile backsplash—creating the perfect space for everyday living and entertaining. The spacious first floor offers 9-foot ceilings, a large living room with soaring 14-15 foot vaulted ceilings, a cozy propane fireplace, a dedicated office that could easily serve as a first-floor bedroom, a renovated bathroom, and convenient first-floor laundry. Luxury plank vinyl flooring flows throughout much of the home, adding both style and durability. Upstairs, you'll find all four bedrooms, including a spacious primary suite featuring lofted ceilings, a walk-in closet, and a private en-suite bath. Modern comforts include central air conditioning, forced hot air heating, a new propane furnace installed in 2025, and a generator hookup capable of powering the home when needed. Step outside and enjoy the best of New Hampshire living with a brand-new deck built in 2024, a level backyard, private drilled well, and septic system replaced in 2020. Outdoor enthusiasts will appreciate direct access to dirt bike and ATV trails right on the property, offering endless opportunities for recreation without ever leaving home. Additional features include a two-car garage, beautiful mountain views, and a tractor that is negotiable with the sale. This move-in-ready property combines updated amenities, outdoor adventure, and peaceful surroundings in one exceptional package. Open house Sunday 6/14 10-12!

165 Governors Rd, Pittsfield

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