$300,000 $278 per sq.ft. Pittsfield NH Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1080  |  Acres: 0.47
Wednesday Aug 26, 2026
Description: Welcome to 28 South Main Street in Pittsfield, NH! This charming 3 bedroom, 2 bath Cape sits high on .47 acres and offers a wonderful opportunity for those looking to start out, settle down, or downsize. Filled with character and warmth, the home features hardwood floors in the living room and a woodstove to take the chill off on those cold New Hampshire nights. The first floor offers a comfortable bedroom, renovated bath, dining room, kitchen, and a convenient laundry room that doubles as a pantry. Enjoy the sunshine and fresh air from the inviting 3 season porch, with two exterior decks providing plenty of space for relaxing, entertaining, or simply enjoying the outdoors. Upstairs, you'll find two additional bedrooms and a 3/4 bath. The full walk-out basement adds valuable space and flexibility, whether you envision a workshop, home gym, hobby area, or additional storage. Outside, there's a handy shed for your gardening and outdoor tools, along with a patio area just off the deck. Recent updates include a new heating system, replacement windows on the first floor, renovated bathrooms, and a nicely paved driveway. Conveniently located close to the amenities of downtown Pittsfield while offering a comfortable setting to call home, this is one you'll want to see! Showings begin at the Open House on Saturday, August 29, and Sunday, August 30, from 10:00 AM-12:00 PM. See MLS Property & Listing Details & 34 images. Includes a Virtual Tour

$315,000 $226 per sq.ft. Pittsfield NH Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1393  |  Acres: 0.1
Tuesday Apr 7, 2026
Description: Back on market with no fault to the sellers! 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! See MLS Property & Listing Details & 31 images.

$319,900 $368 per sq.ft. Pittsfield NH Home »

2 Beds | 2 Baths |   Total Sq. Ft. 870  |  Acres: 0.09
Sunday Aug 23, 2026
Description: BRAND NEW AND AFFORDABLE HOME! Keep your costs low and comfort level high! Two bedroom, two bath, single family residence on its own land, just finished. Super efficient Bosch heat pump with LP Gas assist and whole house AC. Fully applianced eat-in kitchen has fridge, electric range, microwave, and dishwasher. Upstairs full bath has stacked LG washer/dryer. Fully foam insulated for heat/cooling savings and noise cancellation. Situated on a small in-town lot within walking distance of all village amenities has municipal water and sewer. Parking for up to 5 cars. See MLS Property & Listing Details & 12 images.

$348,500 $222 per sq.ft. Pittsfield NH Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1568  |  Acres: 3.01
Monday Aug 3, 2026
Description: Tucked back from the road on just over three private acres, this well-maintained one-story home offers easy, single-level living in a quiet rural setting, with room to roam, tinker, and settle in. Step inside to a light-filled, open layout where the kitchen, dining area, and family room flow together, making everyday living a breeze. The adjoining living room adds a second gathering space, while a dedicated laundry room and pantry keep things functional. A screened porch off the kitchen invites you to enjoy three-season mornings and evenings overlooking the wooded lot. The primary suite features a spacious bedroom, a walk-in closet, and a private en-suite bath. A second generously sized bedroom with its own nearby full bath offers flexibility for family, guests, or a home office. Downstairs, an attached one-car garage and a large unfinished basement provide abundant storage. Outside, the property really shines: 3.01 acres of space with several outbuildings, including multiple wood-frame sheds, great for extra storage, a workshop, or hobby farm use. The home features low-maintenance vinyl siding and a durable standing-seam metal roof (updated with new skylights). Looking for an affordable home on a private lot? Look no further! See MLS Property & Listing Details & 43 images.

$379,900 $117 per sq.ft. Pittsfield NH Home »

4 Beds | 2 Baths |   Total Sq. Ft. 3252  |  Acres: 0.87
Friday Aug 15, 2025
Description: Step back in time with this stately 2 ½ story Colonial home offering over 3,250 SF of living space, set on a generous .87-acre in-town lot. Brimming with historic charm, this 4-bedroom, 1.5-bath residence showcases classic architectural details, including gunstock corners, wide pine flooring, built-in cabinet, mantles, that whisper stories of a bygone era. The traditional layout features spacious rooms with high ceilings, abundant natural light, and timeless craftsmanship throughout. A large kitchen and adjoining formal dining room are perfect canvases for restoration, while the living room and large family room with stone fireplace, provide the ideal setting for gathering and entertaining. Outside, the property boasts an attached barn, offering ample storage, workshop potential, or future creative use. The level lot provides space for gardens, play areas, or outdoor entertaining, all within walking distance to Pittsfield's shops, schools, and parks, and minutes to major highways for easy commuting. While the home requires updates to bring it to its full potential, the solid bones and original character make this a rare opportunity for preservation-minded buyers, renovators, or anyone seeking to restore a piece of New England history. Home is in an Estate and is Sold as is as Seen. Seller makes no warranties/guarantees. Conventional, Cash or Rehab Loan needed. Google directions are incorrect (they will take you to South Main St.). Please use directions I have listed. Agents see non public remarks. See MLS Property & Listing Details & 59 images. Includes a Virtual Tour

$420,000 $374 per sq.ft. Pittsfield NH Home »

Price Change! Reduced by $54,900 down 13% on August 27th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 2008  |  Acres: 1.21
Monday Jul 27, 2026
Description: 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! See MLS Property & Listing Details & 40 images.

$424,900 $251 per sq.ft. Pittsfield NH Home »

2 Beds | 1 Baths |   Total Sq. Ft. 1696  |  Acres: 2
Thursday Aug 20, 2026
Description: Enjoy this almost brand new 1979 ranch home, completely rebuilt from the studs out, including new roof, windows, siding, electrical, and plumbing. Set on 2 private acres just 4 minutes off Route 28 and close to the Chichester line, this 2 bedroom ranch offers a flowing floorplan and a sunroom addition facing the rear of the property. The kitchen has been fully rebuilt with soft close shaker cabinetry, quartz style countertops, and stainless steel appliances including a smooth top range, overhead microwave, and dishwasher. Rich hardwood flooring runs throughout the main living areas, tying the open kitchen, living room, and sunroom into one bright, cohesive space. The sunroom brings in abundant natural light through oversized sliders and windows, framing peaceful, private wooded views and offering direct access to the rear deck, perfect for morning coffee or evening relaxation. A full basement adds valuable storage or future finished living space. The oversized attached garage is insulated and wired, ideal for a workshop, extra vehicles, or seasonal equipment storage, with direct entry into this beautifully updated home. Located at 172 Webster Mills Rd in Pittsfield, this move in ready ranch offers the rare combination of privacy, updated systems, and quality craftsmanship. See MLS Property & Listing Details & 10 images.

$449,000 $217 per sq.ft. Pittsfield VT Home »

Price Change! Reduced by $31,000 down 7% on July 10th 2026
6 Beds | 4 Baths |   Total Sq. Ft. 3108  |  Acres: 1.3
Saturday Jun 20, 2026
Description: 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. Recent septic inspection performed and available. See MLS Property & Listing Details & 47 images.

$479,000 $316 per sq.ft. Pittsfield VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1518  |  Acres: 1.8
Sunday Aug 16, 2026
Description: 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. See MLS Property & Listing Details & 39 images. Includes a Virtual Tour

$499,000 $267 per sq.ft. Pittsfield NH Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1872  |  Acres: 3.12
Wednesday Aug 12, 2026
Description: 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. See MLS Property & Listing Details & 45 images.

$499,900 $469 per sq.ft. Pittsfield NH Home »

Price Change! Reduced by $90,000 down 18% on August 17th 2026
208 Ft. of Waterfront on Pond Wild Goose Pond
3 Beds | 1 Baths |   Total Sq. Ft. 1067  |  Acres: 1.27
Thursday Jul 9, 2026
Description: *MOTIVATED SELLERS* Open House: Saturday, Aug. 22: 10am-12pm! Unique, 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 cottage is the quintessential NH lakefront retreat. Coffee on the deck leads to long summer days on the water! 208' of water frontage, this property was made for making memories! Unlike anything else on the pond, this distinctive cottage embraces camp life with open-concept living, warm pine plank walls, tavern-style lighting & 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. 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. 2nd & 3rd floor sleeping lofts 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! See MLS Property & Listing Details & 45 images.

$262,000 $173 per sq.ft. Pittsford VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1512  |  Acres: 1.2
Wednesday Jul 15, 2026
Description: Don't miss your chance to escape to the beauty of Vermont with this inviting home set on a picturesque country lot at 5190 Whipple Hollow Road. Offering the perfect blend of comfort and peaceful surroundings, this updated move-in-ready property features an open and airy floor plan designed for today's lifestyle. The spacious living areas are filled with natural light, while the updated kitchen flows seamlessly into the dining and living spaces, making entertaining effortless. Step outside to the expansive wrap-around deck overlooking the beautiful yard--ideal for morning coffee and gatherings with family and friends. Recent improvements include a new kitchen, light fixtures, brand-new appliances, updated exterior doors, a new oil tank, and a spacious primary bathroom plus a fully updated second full bath. Price is reflective of any potential maintenance needed, as sellers have never lived at the property full-time. Whether you're looking for your first home, a peaceful retreat, or a place to enjoy the outdoors, this property offers the charm of country living with the convenience of nearby Rutland, outdoor recreation, skiing, golf, lakes, and year-round Vermont adventures. Don't miss this opportunity to make this wonderful property your next home! See MLS Property & Listing Details & 55 images. Includes a Virtual Tour

$290,000 $164 per sq.ft. Pittsford VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1764  |  Acres: 0.73
Wednesday Jul 22, 2026
Description: This private and serene three bedroom, furnished country get-away is located in Pittsford but just minutes to the Chittenden Reservoir and Killington/Pico down hill skiing. The open living room with a dining area greets you at the front door. There is an efficient kitchen with ample counterspace and oak cabinets conveniently located just off the dining area. The first floor has a charming step-down sunroom that provides extra living space for family and friends with a sliding glass door for extra sun light and easy access to the garden. There is a full bathroom and laundry/mudroom area with a door leading to the large covered back porch. From here you can entertain in style or just relax while listening to the babbling brook that passes between the house and back garden paths. The stairway to the second level has a generous landing area with three bedrooms off of it. The primary bedroom has a full bathroom with a dressing room that is currently being used as an office. From here you have the luxury of sitting on the second story partially covered porch with an open balcony for sunbathing in the summer and warmer winter days! There is a yard with a patio and paths with bridges to cross the brook as you make your way to the separate parcel of .27 acres of land behind the house. A peaceful location just minutes to recreation, the Mountain Top Inn and Rutland shopping. See MLS Property & Listing Details & 47 images.

$350,000 $306 per sq.ft. Pittsford VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2288  |  Acres: 5.7
Tuesday Aug 4, 2026
Description: Set on 5.7 acres with mountain views, this well-maintained home sits nicely above the sprawling property, with a terrific front deck that's the perfect spot to sit back, take it all in, and enjoy the sunsets. Inside, you'll find hardwood floors, a comfortable living room with fireplace, and the convenience of an attached garage. A 16' x 32' shed with electricity makes a great workshop or provides plenty of additional storage. There's ample room for gardening, with established gardens in place, while the basement offers additional space for a rec room, storage, or casual hangout area. Two separate portions of the property offer frontage along Route 7, with potential for subdivision. Just up the road from Proctor-Pittsford Golf Course and Pico & Killington Ski Areas, with Rutland less than 15 minutes to the south and Brandon just minutes to the north! See MLS Property & Listing Details & 59 images.

$250,000 Plainfield VT Home »

3 Beds | 0 Baths |   Total Sq. Ft. 0  |  Acres: 1.5
Friday Jul 10, 2026
Description: Every one of us carries a dream of a place where imagination is free to grow. Sometimes it's the land, sometimes it's the building, and every once in a while, it's both. Tucked along East Hill in Plainfield, this little dream-come-true offers dark night skies scattered with stars, expansive views that stretch the soul, and a rare blend of yesterday's character with today's comforts. A little bit of the past, a little bit of the new, and a whole lot of possibility. The current owners began this dream with love and care, but life carried them in another direction before it could be fully realized. Stand on the hillside, take in the view, breath in the air and, and maybe, just maybe, you'll see it too; the wildflowers swaying in the meadow, the sun warm on your face, the quiet promise of a life built your way. The hard work has been done. What remains are open spaces waiting for your own aesthetic, your own story, your own dream. Come see where it takes you. Professionally rebuilt timber-frame barn using locally sourced lumber from Fontane's sawmill, designed to last 100 years with input from a Yestermorrow architect and local builders. Approx. 1100 sq. ft. living space with master loft, second bedroom/office, and high-ceiling kitchen/dining with Marvin windows, transoms, and panoramic south/west views. Attached 1000 sq. ft. insulated workshop/studio with original barn door entry and new vestibule for additional living space. High-efficiency build (R60 roof, R28 walls, natural materials), polished concrete radiant slab, Pacific Energy wood stove, new metal roof, hemlock sheathing, and 2023 shiplap siding. Original features preserved: pocket door, hand-hewn ladder, exposed framing, hay trolley. New well, electrical, plumbing, water filtration (2023); bathroom plumbed for curbless shower plus antique tub. Lumber and insulation on site ready for the new owner's finishing touches. See MLS Property & Listing Details & 38 images.