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324 Fellows Rd, Pittsfield
$2,450,000
4 Beds ⋅ 4 Baths ⋅ 5110057 MLS
Set within 210 acres of unspoiled forestland spanning Killington and Pittsfield, Vermont, The Tweed River Estate is a truly one-of-a-kind property, a private sanctuary where nature and craftsmanship meet. Designed by a renowned architect, the bespoke home is a masterwork in its own right, with exposed beams, high-end custom woodwork, and windows throughout that fill every room with light. Every detail, from the stonework to the finest materials, reflects the artistry of master stonemasons and skilled craftsmen. The house is perched above the Jimmy Dean Brook and the Tweed River, where the sound of running water settles peacefully over the property. Enveloped by forest on all sides, the stone, concrete, and timber structure sits on its mountain top setting so naturally that it feels less built than grown from the land itself, as if it had always been there. Large windows, stone patios and a second-floor porch frame views down the valley to the northeast and out across the surrounding woodland. On mornings when fog fills the valley below, the houses, elevated location gives the sensation of floating above the world on a cloud, a true private retreat. The property spans 210 acres across two contiguous parcels, the majority of which is untouched private forest in Pittsfield, with development potential on the 89-acre Killington parcel. Combining privacy, character, and genuine architectural originality, the estate remains just minutes from an impressive range of amenities, ski resorts, shops, and dining, making this a rare chance to own a home and landscape unlike any other in Vermont.

324 Fellows Rd, Pittsfield

490 Clough Rd, 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

50 Range 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

7 Crescent St, Pittsfield
$1,125,000
5106833 MLS
Excellent opportunity to add a 9-unit residential property to your investment portfolio! Tucked away on a quiet side street just minutes from downtown Pittsfield, this property offers a desirable combination of location, unit mix and off-street parking. The building consists of 5 studio apartments, 3 one-bedroom units and 1 two-bedroom unit, providing a diversified rental mix with broad tenant appeal. A major benefit for investors is that tenants pay their own heat, helping to reduce owner-paid operating expenses. Additional highlights include town water and sewer, newer heating systems and a newer roof, offering added value and peace of mind for the next owner. The property also offers plenty of off-street parking, a valuable amenity, as well as a large private backyard for tenants to enjoy. Conveniently located near downtown amenities and shopping while still enjoying the quieter setting of a side street. Whether you're looking to expand an existing portfolio or add a substantial multifamily asset, this property offers an attractive opportunity with 9 income-producing units under one roof. ***Also available as part of a larger off-market investment portfolio. Additional properties and portfolio information available upon request.***

7 Crescent St, Pittsfield

91 Bombadil Path, 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

1310 & 1311 Upper City, Pittsfield
$799,000
4 Beds ⋅ 4 Baths ⋅ 5081561 MLS
Oh the Views! Perfectly sited, this Quintessential 1780 Colonial Farmhouse is framed by lovely landscaping & timeless New England charm. This exceptional homestead includes two separate parcels: 4.5 country acres surrounding the home plus an additional 3.06 acres w/ vintage barn just across the street. Brimming with charm & character, this expansive home has been thoughtfully updated & improved throughout. The 4 season porch serves as an ideal mudroom & a welcoming place to unwind. A recently renovated kitchen features new appliances, cabinetry & quartz countertops, and open seamlessly to a sun-filled family room with informal dining and scenic backyard views. The main level also offers a classic dining room, living room, private office (or potential bedroom), fully bath, second mudroom, and a pantry/canning area leading to the carriage house & bonus room. Upstairs, you'll find a spacious primary suite, a 2nd ensuite bedroom, a 3rd bedroom & bath, and a sunlit office or 4th bedroom. Additional highlights include abundant closet space, a convenient laundry area & charming front & back staircases. Beautiful details shine throughout - moldings, wide pine floors and a blend of informal living spaces across 4,156 sq ft. The carriage house/garage offers ample space for vehicles, a workshop & future expansion. This property has been meticulously maintained w/updated systems. Step outside from the family room onto a charming stone patio overlooking "froggy pond", gardens, red maples, fruit trees & more. The vintage barn, sold "as is" offers incredible potential is sited on the separate parcel. With endless possibilities, farm equestrian property, multigenerational home, ADU, Bed & Breakfast, event venue - this peaceful and picturesque homestead is ideal for living, working and playing.

1310 & 1311 Upper City, Pittsfield

79 High St, 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

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

7 Shaw Rd, Pittsfield
$774,000
4 Beds ⋅ 3 Baths ⋅ 5091752 MLS
PRICE JUST REDUCED! NEW CONSTRUCTION with the opportunity to make it uniquely yours! Set privately among the trees on a quiet country road, this thoughtfully designed home offers the best of new construction without the long wait. The builder estimates approximately 90 days from buyer selections to completion, with time still available to personalize flooring, cabinets, countertops, paint, and more. The open first floor features a stunning fireplace, formal dining area, and inviting living space. Upstairs, discover 3 bedrooms, a full bath, laundry, and a spacious primary suite with private bath and walk-in closet. Enjoy hardwood throughout the first level, granite countertops, central AC, a covered front porch, 12x12 back deck, and attached 2-car garage. Private setting, modern design, and personalized finishes, this is the opportunity you've been waiting for! Showings are by appointment only. Make your selections now and you could be settled into your new home by the end of the year!

7 Shaw Rd, Pittsfield

2 Depot & 27 Carroll Street, Pittsfield
$729,900
5088472 MLS
4 separate lots packaged, and approximately 20,000 SF between two large buildings with potential for 27+ units. The vacant parcel can accommodate approximately 30 parking spaces, or future development opportunities. The package includes a well-maintained 5-unit building featuring 6,769 SF of finished space, a cap rate exceeding 13.5%, and strong long-term tenants already in place. Additional upside exists through potential subdivision and conversion of the commercial and unfinished areas, creating the possibility for 15+ total units. Recent updates include renovated kitchens and baths in select units, newer flooring, a young roof, and a highly efficient Buderus boiler. Also included is a massive 8,300+ SF mixed-use building that formerly operated as a popular pizza restaurant, with substantial restaurant equipment still in place including pizza ovens, fridges, and burners. The upper floors require renovation but offer substantial square footage with the potential for 9+ additional apartments, contributing to the combined 27+ unit potential. Located in the heart of downtown Pittsfield, tenants enjoy walkable access to shops, restaurants, and everyday conveniences, while nearby Drake Field and the Suncook River provide outdoor recreation. Concord is under 30 minutes away, with Boston and Portsmouth also within reach. Buyers to perform their own due diligence regarding approvals, permitted uses, parking requirements, and development potential. PRIVATE SHOWINGS Friday 4–6PM & Saturday 1–3PM.

2 Depot & 27 Carroll Street, Pittsfield

221 Fiddlehead Ln, 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

22 Mullen Dr, Pittsfield
$589,000
3 Beds ⋅ 2 Baths ⋅ 5114541 MLS
Quality New Construction on 2.24 Acres in Pittsfield, NH! From the moment you pull into the driveway and step inside, the quality of construction and attention to detail are evident. Located on a picturesque dead-end road, this newly constructed three-bedroom home offers a peaceful country setting with room to enjoy the outdoors. The open-concept kitchen, dining, and living area creates a comfortable, inviting space for everyday living and gathering with family and friends. The thoughtfully designed floor plan offers an easy flow, while the quality workmanship is evident throughout. Features include central air conditioning, Matthew Brothers Walcott windows, LP SmartSide exterior siding with a 50-year warranty, a hybrid water heater, drilled well producing 15 gallons a minute with a constant pressure pump, and a high-efficiency LP gas forced-air furnace, to name just a few. Enjoy all the benefits of a brand-new home without the time and stress of building yourself. Take in the quiet surroundings and enjoy the charm of Pittsfield, with a scenic drive along Catamount Road and nearby access to Drake Field, White’s Pond, and the Suncook River. From apple picking and the charming downtown waterfall to the popular annual Hot Air Balloon Rally, there’s plenty to enjoy throughout the seasons. If you’ve been looking for quality new construction, a welcoming layout, and the appeal of country living, 22 Mullen Drive is ready for you to make it your own! The interior photos coming soon, stay tuned!

22 Mullen Dr, Pittsfield

89 Townsend Brook 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

90 Deer Meadow Rd, Pittsfield
$525,000
3 Beds ⋅ 3 Baths ⋅ 5103414 MLS
Welcome to the home you've been waiting for! This beautifully maintained Colonial offers the perfect blend of space, comfort, and convenience, nestled on a picturesque 1.51-acre lot with a peaceful country feel. Inside, you'll find open concept living with ample space in the the gourmet kitchen/dining area, office space, and living room with fireplace. Additionally there are three spacious bedrooms, two full bathrooms, and a convenient half bath. The bright and inviting floor plan is ideal for both everyday living and entertaining. A standout feature is the enormous bonus room above the attached garage offers endless possibilities as a fourth bedroom, family room, game room, home office, or fitness space. Enjoy the privacy and tranquility of the expansive yard while remaining just a short commute to Concord, Manchester, and the Lakes Region. Whether you're looking for room to grow, space to entertain, or simply a place to relax and enjoy country living, this exceptional home has it all. Don't miss your opportunity to make this stunning Colonial your next home!

90 Deer Meadow Rd, Pittsfield

7 True Rd, Pittsfield
$524,900
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.

7 True Rd, Pittsfield

Lot 4 Mullen, Pittsfield
$499,900
5088324 MLS
Welcome to Mt. View Village in beautiful Pittsfield, New Hampshire! An extraordinary offering of approximately 165 acres set high above Mullen Drive with sweeping scenery and exceptional potential. This remarkable property may be one of the most impressive large acreage opportunities currently available, offering the perfect setting for a private estate, family compound, equestrian property, or possible subdivision potential with proper approvals. The land features a beautiful natural landscape with rolling terrain, wooded surroundings, and elevated settings that create privacy and picturesque views. Whether your vision is building a dream home tucked away in nature or exploring future development possibilities, this property offers a rare combination of size, settings, and opportunity. Located in historic Pittsfield, this property allows you to enjoy the charm of a New Hampshire town known for its scenic country roads, local farms, apple orchards, the Suncook River, White’s Pond, Drake Field, and the beloved annual Hot Air Balloon Rally. Residents appreciate the area’s small-town pride, natural beauty, and convenient access to Concord, Alton, the Lakes Region, and major commuting routes.

Lot 4 Mullen, Pittsfield

2 Depot St, Pittsfield
$479,900
5088125 MLS
Investors, look no further for a deal of a lifetime. This large 5-unit property offers 6,769 SF of finished space with a cap rate exceeding 13.5%, along with potential for additional units through subdivision of the commercial spaces or expansion of the existing layouts. A current storage area also presents the opportunity for conversion into an additional unit. The interior residential units are well maintained with solid long term tenants. In the past 3 years, the largest unit has been updated throughout, featuring a renovated kitchen with beautiful granite countertops, stainless steel appliances, and newer flooring. The bathrooms have also been remodeled with updated tubs and vanities. The smaller one-bedroom unit offers a cozy layout and has seen updates as well, including new carpeting, along with improvements to the kitchen and bathroom. The property’s large footprint offers the potential for 6+ additional residential units through conversion of the commercial spaces, along with the possibility of 5+ more units in the unfinished attic — creating the opportunity for an intriguing combined 15+ unit building. Parking would be needed as required by the town for the increased units but that can be fulfilled with the sale of the property across the street that can be purchased as a package (MLS # 5088311). Other updates include a young roof and a young highly efficient Buderus boiler. Located in the heart of downtown Pittsfield, tenants enjoy walkable access to shops, restaurants, and everyday conveniences in a true small-town setting. Nearby Drake Field offers outdoor recreation along the Suncook River with trails, fields, and courts. Commuting is also convenient, with Concord under 30 minutes away and Boston & Portsmouth less than an hour. PRIVATE SHOWINGS Friday 4-6PM and Saturday 1-3PM.

2 Depot St, Pittsfield

253 Lookout Rd, 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

15 Leavitt Rd, Pittsfield
$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

23 Concord Hill Rd, Pittsfield
$299,000
3 Beds ⋅ 1 Baths ⋅ 5082428 MLS
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

75 Concord Hill Rd, Pittsfield
$267,000
2 Beds ⋅ 1 Baths ⋅ 5114032 MLS
A single family home on almost one and a half acres under $275,000...say what?! This 2 bedroom manufactured home is situated on a fantastic piece of land that with a little bit of landscaping, will be absolutely beautiful. The paved driveway offers a ton of parking, the sprawling yard boasts an expansive place to play, entertain, garden or just grill and chill after a long day of work. The open concept living room and kitchen flow nicely into each other and there is an abundance of counterspace to host your kitchen gadgets. Travel down the hallway where you will find the first of 2 bedrooms, a large full bathroom, laundry area and the primary bedroom. Located only 20 minutes to Concord, 35 minutes to Manchester, 30 minutes to the Lakes Region and 55 minutes to Portsmouth, it doesn't get much more of a central location than this for work and fun. Welcome Home! *Offer deadline set for Saturday (10/17) at noon*

75 Concord Hill Rd, Pittsfield

27 Carroll St, Pittsfield
$250,000
5088311 MLS
DEALS! 3 parcel package for just under 250,000. The 3 parcels includes a massive 8300+ sf building and a separately deeded buildable .28 acre parcel(combined lot 5&6). The building once functioned as a popular pizza restaurant, which still has all the expensive restaurant equipment still in place including multiple fridges, pizza ovens, burners, etc. The first floor includes a residential owners unit in the back, and also a separate commercial unit, perfect for another retail/restaurant or office use. The 2nd & third floor is in need of work but offers ~5000 square feet of space, perfect for ~9+/- apartments, bringing the total potential unit count over 12.Parking is required for the potential unit conversions, where the adjacent lot offers approximately 30 parking spaces. Alternatively, the second lot is buildable and meets the required lot size and setback requirements set by the town. This property requires a lot of work, and buyers are responsible for conducting their own due diligence regarding all building requirements, permitted uses, restaurant equipment and potential expansion opportunities. This property and parcels can be purchased as a package with MLS#5088125. PRIVATE SHOWINGS friday 4-6PM & Saturday 1-3PM.

27 Carroll St, Pittsfield

18-22 Main St, Pittsfield
$249,900
5093110 MLS
**BACK ON MARKET – Due to no fault of the seller.** Union Block – Historic Commercial Opportunity! Step into history with the iconic Union Block, a landmark commercial building built in 1895 and filled with potential. Situated in a prominent Main Street location, this versatile property presents an exceptional opportunity for investors, entrepreneurs, and business owners. The former Main Street Variety storefront has been updated and is ready for its next chapter. Currently set up for another convenience store, the space also offers excellent potential for a coffee shop, bakery, café, boutique retail shop, or other commercial venture. Recent improvements include updated finishes and efficient mini-split heating and cooling systems, making the storefront ready for immediate use. With its historic character, strong street presence, and flexible layout, Union Block could accommodate a variety of commercial, retail, office, mixed-use, or redevelopment concepts, subject to town approvals. While portions of the building will require rehabilitation and updating, the property offers a unique opportunity for value-add improvements while preserving a piece of local history. Whether you're looking to continue its retail legacy, pursue a redevelopment project, or create something entirely new, Union Block provides the foundation to bring your vision to life. Bring your ideas and unlock the potential of this historic Main Street property.

18-22 Main St, Pittsfield

100 Hawk Trl, Pittsfield
$70,000
5108212 MLS
Rare opportunity to build in the desirable Hawk Mountain community on an unusually accessible, gently sloping parcel. Located between Hawk Mountain Road and Hawk Trail, this lot is one of only a handful in the community that avoids the steep, challenging terrain typical of mountain properties. The favorable topography can simplify site work, driveway construction and the eventual building process - an important advantage for anyone planning a Vermont getaway. Even better, a State-issued WW permit is already in place for a three-bedroom residence, providing a valuable head start toward development. Architectural review and protective covenants help preserve the distinctive character and quality of life that make this small mountain community so appealing. Outdoor recreation is right at your doorstep, with the Green Mountain National Forest just one mile away for hiking, mountain biking, snowshoeing and access to the VAST snowmobile trail network. Killington and Pico ski resorts are also just a short drive away, offering some of Vermont's best skiing and riding. With its combination of gentle terrain, permitted three-bedroom wastewater system and exceptional location, this is a rare chance to build your own Vermont mountain retreat on one of the community's most accessible building sites. Bring your plans and make it your own!

100 Hawk Trl, Pittsfield

360 Liberty Hill Rd, Pittsfield
$60,000
5055283 MLS
Positioned at the scenic corner of Liberty Hill Road and Eagle Rock Road, this 2.02-acre offering, comprised of two separate lots, presents an exceptional opportunity to build in the heart of the beloved Green Mountains of Vermont. Whether dreaming of a cozy mountain getaway, a modern rustic retreat, or an investment with high recreational appeal, this property provides the canvas and the location. Nestled just minutes from the charming village of Pittsfield, you will enjoy both quiet seclusion and convenient access to local essentials. The land is ideally situated a short drive from the Killington Ski Area and its year-round amenities, making it a fantastic base for skiing, snowboarding, biking, and apres-ski fun. For those who crave adventure and natural beauty, the property sits near local hiking and snowmobile trails, meandering rivers and streams, and the iconic Clear River Tavern, an area favorite. This corridor also leads directly through the picturesque town of Rochester and up to the Waitsfield Valley, home to the renowned Sugarbush Resort. Build your vision in a setting where outdoor recreation, small-town charm, and Green Mountain serenity all converge. This parcel is more than just land, it is your gateway to Vermont living.

360 Liberty Hill Rd, Pittsfield

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