$299,000 $167 per sq.ft. Chester VT Home »

Price Change! Reduced by $150,000 down 50% on July 29th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1788  |  Acres: 3.3
Wednesday Jan 14, 2026
Description: Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved road leads you home, winding past back woods and pastoral farmland before arriving at the property. The elevated deck becomes your front-row seat to the landscape below, perfect for morning coffee, summer dinners, or simply listening to the brook roll past. Inside, the home feels warm, functional, and comfortable. A large living room is anchored by a substantial woodstove that brings real Vermont heat and atmosphere through the colder months. The sunroom is a standout space, wrapped in windows and overlooking the brook, creating a peaceful place to read, work, or relax. From here, step directly onto the deck and into the outdoors. The layout offers three bedrooms and two bathrooms, including a ground-floor bedroom for easy everyday living. Storage is abundant throughout, making room for outdoor gear, tools, and seasonal equipment. The land itself adds real value. With acreage on both sides of the brook, there's room to garden, explore, build trails, or simply enjoy your own stretch of water and woods. The surrounding countryside delivers classic Vermont scenery--rolling fields, forested hills, and quiet country roads. Located just minutes from the village of Chester and close to Okemo, Stratton, and Magic Mountain, this is a true four-season basecamp for skiing, hiking, biking, fishing, and exploring Vermont's natural beauty. A property that offers privacy, water frontage, land, and mountain access--without giving up convenience. See MLS Property & Listing Details & 31 images.

$390,000 $299 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1304  |  Acres: 1
Thursday Apr 30, 2026
Description: Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that's hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates. Refinished wide plank floors bring warmth throughout, while the kitchen features granite countertops and a farmhouse sink. Upstairs, a vintage Martini pedestal sink adds a distinctive, curated touch to the bathroom. Outside, the level lawn provides usable space for everything from gardening to entertaining, and the substantial post-and-beam barn opens the door to a wide range of future uses, storage, workshop space, or potential expansion. Located just minutes from Chester's Stone Village, the Grist Mill, and Smitty's Market, and within easy reach of Okemo, Bromley, Killington, Stratton, and Mount Snow, this is a strong option for both full-time living and recreational use. Currently used as a long-term rental and previously operated as a successful Airbnb and personal vacation home, the property offers flexibility for a variety of ownership goals. See MLS Property & Listing Details & 51 images.

$469,000 $193 per sq.ft. Chester VT Home »

Price Change! Reduced by $10,000 down 2% on July 6th 2026
3 Beds | 3 Baths |   Total Sq. Ft. 2676  |  Acres: 2
Tuesday May 5, 2026
Description: Located in the village of Chester, this 3-bedroom, 3-bath property offers a rare amount of space and flexibility for an in-town setting. You'll enter through the heated attached two-car garage into a layout that's both functional and easy to live in, with room to spread out when you need it and gather when you want to. The kitchen features warm wood cabinetry, a breakfast bar, and a flexible area that works just as well for casual dining as it does for a home office setup. The dining space flows easily into a sunken living room, where the pellet stove becomes a natural gathering spot. Two bedrooms on the main level, each with their own bath, make this a great fit for a variety of living situations. Upstairs, you'll find a spacious bedroom, a separate flex room currently used as a movie room, and an unfinished bonus area ready for whatever you have in mind. Storage is not an issue here, between the closets and full basement, there's plenty of space to keep things organized. The home is equipped with a new furnace and four heating zones, offering efficiency and control throughout. Outside, a wide back patio gives you a great place to relax, while the barn and oversized three-bay garage offer serious utility for storage, equipment, or hobbies. The detached garage is currently rented for $500 per month, and the tenant would be open to continuing that arrangement with the next owner. The property borders Lovers Lane Brook, adding to the natural setting and privacy, all just minutes to Chester's shops, dining, and village amenities. If you've been looking for an in-town property with more space and versatility than most, this one is worth a look. Furnishings are negotiable for anyone looking for a truly turn-key property! See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$479,000 $295 per sq.ft. Chester VT Home »

Price Change! Reduced by $10,000 down 2% on August 14th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1626  |  Acres: 0.33
Thursday Jun 18, 2026
Description: Located in the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines modern minimalist style with artisan craftsmanship. Set on .33± acres, this light-filled property features wide-pine floors, exposed beams, and a Vermont Castings woodstove anchoring an inviting open-concept living space. The kitchen/dining area showcases country cabinets with butcher block counters, attractive center island with Vermont slate/stone counter, stainless steel sink and dishwasher framed by a wall of windows with a picturesque valley view. A spacious first-floor bedroom, full bath and convenient laundry area provide easy one-level living. Upstairs, two additional bedrooms with generous closets share a stylish full bath finished with classic subway tile. Recent upgrades include energy efficient systems and a new four-bedroom leach field, offering peace of mind for full-time residents, second-home owners, or investors. Offered fully furnished, this turnkey Vermont property has a proven history as a successful seasonal rental. Experience the vibrant community of Chester, with its charming village shops and restaurants, town pool, recreation area, premier disc golf course, pickleball and tennis courts, snowmobile club, and thriving artisan culture. Ideally located near Okemo Mountain Resort and Magic Mountain ski areas. This quintessential Vermont home is equally suited as a primary residence, ski getaway, vacation home, or income-producing investment property. See MLS Property & Listing Details & 33 images. Includes a Virtual Tour

$649,000 $294 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2204  |  Acres: 1
Wednesday Jul 1, 2026
Description: Welcome to your private gated mini-estate...an enchanting sanctuary where every detail delights the eye. Nestled adjacent to meticulously manicured woods, this one-of-a-kind residence blends storybook charm with thoughtful, high-end finishes. A sweeping entry leads past intimate outdoor living spaces centered around a dramatic floor-to-ceiling exterior fireplace, perfect for cool evenings and quiet reflection. Step inside to discover warm, curated interiors where a matching floor-to-ceiling indoor fireplace anchors a cozy great room...an ideal focal point for gatherings and quiet nights in. The custom kitchen is a chef's and designer's showcase making meal prep effortless and stylish. Cute, artful decor and exceptional millwork accentuate every room..every little detail has been considered and executed with eye-popping precision. Natural light pours through thoughtfully placed windows, highlighting textures, finishes, and curated vignettes around nearly every corner. In addition to the four private bedrooms, the special loft above the second-floor den offers a "fun" sleeping area and great retreat for the "kids". Unique sightlines and charming nooks reveal something special at every turn.unexpected architectural details, refined accents, and cozy gathering spots create a home rich in personality and comfort. The floorplan flows intuitively while offering distinct spaces for entertaining and everyday living. Practicality meets luxury with a spacious second garage providing room for toys, workshop space, or secure storage perfect for multi-vehicle households or hobbyists. The gated setting ensures peace of mind and exclusivity, while the manicured wooded grounds offer a serene backdrop and a strong connection to nature. Come see how every corner captures your attention and inspires a sense of wonder at home. This mini-estate is only 10 miles from world-class skiing at Okemo and golf at Fox Run...then enjoy the 5 lakes of Okemo Valley and the nearby VAST trails! See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$325,000 $185 per sq.ft. Chesterfield NH Home »

Price Change! Reduced by $25,000 down 8% on July 24th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1855  |  Acres: 1.13
Thursday Jun 18, 2026
Description: Welcome to 205 Route 9 in Chesterfield, NH, a home designed for easy living. This inviting ranch combines the convenience of a single-level floor plan with valuable updates, including a newer metal roof (2020), Harmon pellet stove, and updated appliances. Downstairs, the finished bonus room provides flexibility that's hard to find. Use it as a playroom, home office, workout space, game room, or whatever best fits your lifestyle. It's a great extension of the home's living area without sacrificing storage space. Outside, the large yard offers plenty of room to spread out and enjoy. Whether you're gardening, entertaining, setting up a fire pit, or just soaking up some sunshine, there's plenty of space to make it your own. Conveniently located just minutes from Keene and a short drive to Brattleboro, this home offers the best of both worlds: easy access to shopping, dining, and commuting routes while still enjoying all that Chesterfield has to offer. With thoughtful updates already completed and room to make it your own, this home is ready for its next chapter. See MLS Property & Listing Details & 42 images.

$360,000 $186 per sq.ft. Chesterfield NH Home »

Price Change! Reduced by $25,000 down 7% on August 3rd 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1938  |  Acres: 2.8
Thursday Jun 4, 2026
Description: Welcome to 174 Pond Brook Road, a Contemporary Mountain Chalet nestled on a private, wooded 2.8-acre lot in West Chesterfield. Built in 1977, this unique home offers impressive architectural character, beginning with a wide entry foyer that opens up to a dramatic, three-story barrel stairway. The main living space features soaring vaulted ceilings, a cozy wood fireplace, and massive windows that bring the beauty of the surrounding nature indoors. Seamlessly connected is the galley-style kitchen and a dining bump-out offering panoramic woodland views on three sides. The main level also includes a convenient half-bath and a versatile bonus room, ideal for a home office, den, or main-floor guest space. Upstairs, the open landing and second-floor foyer look down over the living room below, leading to three distinct bedrooms and a large full bathroom. The walk-out lower level is built for functional New England living, featuring a practical mudroom with a separate entrance, a dedicated laundry room, and direct access to the integrated one-car garage. Exterior highlights include a durable metal roof and a spacious wrap-around front deck, perfect for relaxing and watching the local wildlife. Situated with 371 feet of public road frontage in a quiet rural residential area, this property offers a peaceful, private retreat ready for your personal touch. Join us for an open house on Saturday 6/6/26 from 11am-1pm, or schedule your private tour today! See MLS Property & Listing Details & 46 images.

$389,900 $189 per sq.ft. Chesterfield NH Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2059  |  Acres: 3
Thursday Aug 27, 2026
Description: Welcome to 1750 Route 9 Chesterfield NH. Filled with lots of natural light and plenty of space, this 3 bedroom, 2 bath home is ready for new owners to bring their vision and make it their own. The home features a large pantry, hardwood floors, convenient second floor laundry and 2- car garage. (complete with an EV Charging station) The property previously featured an apartment on the 2nd floor, providing potential for additional living space for extended family, guests or rental income. This classic farmhouse is set on 3 acres in a country setting with plenty of land to enjoy outdoor activities and privacy. Just a short drive away is scenic Spofford Lake, known for its great fishing, water quality and water sports. Chesterfield Gorge is an even shorter drive away and is an excellent for short hikes and / or picnics. Nicely situated between both Brattleboro VT and Keene ( about 10 minutes either way ) OPEN HOUSE 8/28 4:30 to 6:30 and 8/30 1-3 pm See MLS Property & Listing Details & 39 images.

$420,000 $203 per sq.ft. Chesterfield NH Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2067  |  Acres: 1.4
Monday Jul 27, 2026
Description: Nestled along a quiet country road in desirable Chesterfield, this classic Cape-style home offers the perfect blend of timeless charm and thoughtful updates. Set on 1.4 beautifully landscaped acres, the property overlooks a picturesque pond and open meadow, creating a peaceful setting you'll enjoy year-round. Inside, natural sunlight fills the spacious living areas, highlighting the hardwood floors and warm, inviting character throughout. The flexible floor plan offers 3 bedrooms, a formal dining room, a comfortable living room with a cozy hearth and gas stove, plus a convenient first-floor laundry room and half bath. Classic details preserve the home's original charm while newer windows, vinyl siding, and an architectural shingle roof provide peace of mind. Step outside to enjoy the tranquil surroundings from the deck overlooking the backyard, where mature landscaping, open green space, and scenic views create the perfect backdrop for relaxing or entertaining. An attached one-car garage, drilled well, private septic, and easy access to Keene, Brattleboro, and nearby Spofford Lake make this property as practical as it is beautiful. See MLS Property & Listing Details & 36 images.

$449,900 $230 per sq.ft. Village of Spofford in Town of Chesterfield NH Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1958  |  Acres: 0.31
Thursday Aug 20, 2026
Description: Storybook charm in the sweet village of Spofford! Tucked behind a welcoming picket fence and an enchanting English-style garden, this delightful 3-bedroom, 2-bath Antique Cape is filled with warmth, character and unexpected surprises. Step inside to beautiful wide pine floors and an adorable eat-in kitchen featuring granite counters, recessed lighting and even a secret pantry! Just off the kitchen is a ¾ bath with a custom tiled shower. The inviting front living room, complete with a cozy pellet stove, is the perfect place to settle in on a chilly New England evening. The spacious family room addition, added in 1992, may quickly become your favorite room in the house! With plenty of space for a large dining table and comfortable sitting area & wood stove, it was made for gathering with family and friends. Sliders open to the deck overlooking the cozy side yard--perfect for summer dinners, morning coffee and entertaining. Upstairs, the primary bedroom is simply enchanting, with a wonderful cottage-style feel that you are sure to fall in love with. You'll also find an office area, full bath with tiled floor, and an additional bedroom with charming built-ins. And then there are the extras that make this property truly special! A whimsical cottage shed with a loft and sleeping quarters creates the sweetest little escape--grab a good book, sneak away for an afternoon nap or simply enjoy your own private hideaway. Nearby, a cozy fire pit area is ready for summer nights under the stars. The large garage offers yet another bonus: a studio apartment, (currently rented), providing an opportunity for additional income or flexible space for extended guests. All of this is just minutes from beautiful Spofford Lake, the Spofford Post Office and a short drive to Keene. This isn't just a house, it's a chance to slow down, settle in and enjoy the charm of village life. Come experience a simpler way of living...the way it was meant to be. See MLS Property & Listing Details & 46 images.

$595,000 $216 per sq.ft. Chesterfield NH Home »

Waterfront on Lake Spofford
3 Beds | 2 Baths |   Total Sq. Ft. 2750  |  Acres: 1.1
Thursday May 14, 2026
Description: Tucked away at the end of the road, this one-of-a-kind contemporary hexagon home offers peace, privacy, and inspiring views of Spofford Lake. Set on 1.1 acres with flowering gardens and a thriving vegetable garden, the property feels like a private sanctuary. Inside, warm pine floors lead through inviting living spaces including a sun-drenched glass sunroom, cozy den, artist studio, and living room with fireplace and wood stove. With 3 bedrooms, 2 baths, a large laundry room, and attached 2-car garage, this special home blends comfort, creativity, and nature beautifully. See MLS Property & Listing Details & 41 images.

$849,900 $265 per sq.ft. Chesterfield NH Home »

3 Beds | 3 Baths |   Total Sq. Ft. 3210  |  Acres: 12.19
Friday Aug 7, 2026
Description: Charming Colonial Retreat on 12+ Private Acres Welcome to your ultimate private sanctuary! This beautiful 3-bedroom, 3-bathroom Colonial offers the perfect blend of modern convenience, space, and tranquil living. Nestled on a sprawling 12.1-acre lot, this home provides exceptional privacy while remaining ideally situated near the Vermont and New Hampshire borders for easy commuting, dining, and outdoor recreation. Inside, you'll find a bright and airy open-concept layout designed for seamless everyday living and effortless entertaining. Showings will begin on August 17th 2026. See MLS Property & Listing Details & 38 images.

$1,125,000 $326 per sq.ft. Chesterfield NH Home »

3 Beds | 3 Baths |   Total Sq. Ft. 4048  |  Acres: 6.61
Thursday Aug 6, 2026
Description: A home 250+ years in the making, has just been offered for the first time! A perfect representation where classic New England style meets brand new modern convenience and elegance. This 3-bedroom, 2.5-bath home features high end finishes, historic displays of craftsmanship, and an incredible vision that makes this house a home. The outside features field stone siding and harmonious landscaping all on a sprawling private parcel of 6.6 acres. Yes, you also have your very own, perfectly manicured, apple orchard, an oversized 3 car garage with ample additional storage, a gazabo, trellis, and much more. Inside you'll find a vaulted ceiling in the chef inspired kitchen featuring high end appliances, custom wood cabinets, center island, and farmhouse style sink. Just off the kitchen you'll start the day enjoying your morning coffee, reading the paper, or watching the news in the wrap-around breakfast nook. The main living space is primarily on one floor with a large ensuite bedroom boasting hand hewed beams, wide plank flooring, large windows, vaulted ceiling, ceiling fan, and 2 large walk-in closets; all finished with a perfect touch in the spa style bathroom. The warm living room offers a stone fireplace, built-in bookshelves and ample sunlight. The dedicated dining room has a secret pass-through to the kitchen sure to impress any dinner guests. Upstairs you'll be amazed with the guest bedroom and incredible lines of the adjoining bathroom. This private space offers guests a soaking tub, walk-in shower and plenty of impressive design features. The finished basement offers even more space to relax and unwind, this space could be a private office, media room, workout room, or just an extra TV room. Located perfectly between two large towns, your shopping and restaurant needs are just minutes away. Close to beautiful Spofford Lake, ski areas, hiking/walking/snowmobile trails, and easy access to highways. THIS HOME IS AN ABSOLUTE MUST SEE! See MLS Property & Listing Details & 50 images.

$1,600,000 $656 per sq.ft. Village of Spofford in Town of Chesterfield NH Home »

Price Change! Reduced by $300,000 down 19% on July 23rd 2026
Waterfront on Pond
3 Beds | 2 Baths |   Total Sq. Ft. 2440  |  Acres: 57.76
Saturday Nov 15, 2025
Description: SHOOTING STAR FARM is a private, fully equipped horse facility on 57± acres of open turnout and protective woodland. Purpose-built for breeding and training, it offers turnkey infrastructure and serenity for serious equestrian pursuits--without sacrificing the creature comforts of home. The 1984 chalet-style house is sited for pasture and pond views, with a sunlit chef's kitchen overlooking the red barn's activity. The main floor also includes an open, spacious living area w/access to a 3-season porch and deck, for warm-weather relaxation; 2 Bedrooms, and a full bath complete this level. Upstairs, find a restful primary BR with a luxurious custom bath. The walk-out lower level features 4 rooms, laundry, a wood stove, and a 2-car garage. The home's interior is being repainted now. For the horses, the c.2000 breeding barn has 12 stalls, wash stall, and a heated feed/lab/tack room, and a separate well. The centerpiece of the farm is a like-new facility with 14 stalls, indoor arena, a lovely galley kitchen, a ¾ bath with laundry, and a big office/meeting upstairs, both levels with mini splits for heat & AC. Additional amenities include a stunning granite patio w/firepit, large outdoor arena, multiple paddocks, hay storage, equipment lean-tos, and ample trailer/staff/guest parking. Off-farm riding includes miles of dirt roads and access to nearby 13,000-acre Pisgah State Park w/62 miles of trails. Shooting Star is more than a farm, t's a lifestyle investment for those who value privacy, purpose, and the quiet satisfaction of working with horses in a setting that inspires. Just 15 mins. from Keene, NH for shopping, dining, and all services. Close to I-91, too. See MLS Property & Listing Details & 59 images. Includes a Virtual Tour

$489,900 $454 per sq.ft. Chichester NH Home »

Price Change! Reduced by $10,000 down 2% on August 19th 2026
3 Beds | 1 Baths |   Total Sq. Ft. 1780  |  Acres: 1.03
Friday Jul 24, 2026
Description: Welcome home to this charming and inviting 3-bedroom, 1-bath ranch on an Acre of land, nestled in the small town of Chichester. Offering comfort, convenience, and plenty of space to make your own, this home is perfect for those seeking a peaceful setting with easy, one-level living. Step inside to discover a warm and welcoming layout designed for everyday living. The beautifully remodeled kitchen is a true highlight, featuring brand new appliances, stunning granite countertops, and new shaker-style cabinets, perfectly blending style and functionality. New flooring adds a fresh, modern touch, while the finished lower level provides additional living space ideal for a family room, home office, or recreation area, along with plenty of storage. A delightful breezeway connects the home to the spacious two-car attached garage, which is ideal for staying out of the elements while also providing a versatile space for storage, a mudroom, or a cozy sitting area. Outside, the property truly shines. A large barn offers endless possibilities for hobbyists, workshop enthusiasts, or those looking to raise animals. Whether you're dreaming of a creative studio, tinkering space, or a small homestead setup, this versatile outbuilding is ready to bring your vision to life. Enjoy the charm of small-town living while being just a short drive to the State Capital of Concord, offering convenient access to shopping, dining, and services. With room to spread out both inside and out, this property combines warmth, practicality, and opportunity in one inviting package. Come see all that this Chichester home has to offer and imagine making it your own. See MLS Property & Listing Details & 37 images.