Pittsfield Homes for Sale

Welcome to Pittsfield, Massachusetts—a charming city nestled in the heart of the Berkshires, where rich history meets vibrant community living. Known for its stunning natural landscapes and cultural attractions, Pittsfield offers a unique blend of outdoor adventures and urban amenities. With the picturesque Berkshire Mountains as a backdrop, residents enjoy an array of recreational activities, from hiking and skiing to boating on the serene lakes that dot the region. The city boasts a thriving arts scene, highlighted by the renowned Barrington Stage Company and the Berkshire Museum, making it a cultural hub for residents and visitors alike.

For those considering a move to this delightful city, Pittsfield presents an exciting array of homes for sale. Whether you’re searching for a cozy single-family home with a charming yard or a modern condo with breathtaking views of the mountains, the real estate market here has something for everyone. Many properties feature classic New England architecture, offering a glimpse into the city’s storied past, while newer developments provide contemporary living spaces equipped with the latest amenities.

Living in Pittsfield means being part of a welcoming community that values connection and quality of life. With excellent schools, local parks, and a variety of dining options, it’s a perfect place for families, professionals, and retirees alike. Explore the homes for sale in Pittsfield today, and discover the perfect residence where you can create lasting memories in this beautiful city!

Newest Pittsfield Homes for Sale

$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

$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

$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

$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

Start Your Search

board logo Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .