$250,000 $219 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1140  |  Acres: 0.25
Wednesday May 13, 2026
Description: There's something quietly reassuring about a home that's stood the test of time--and this classic dormered Cape in Chester delivers just that, with a clean, updated feel that suits today's lifestyle. Built circa 1945, the home offers three comfortable bedrooms--including a convenient ground-floor bedroom--and 1.5 baths, giving you flexibility for guests or single-level living. The layout is practical and easy to live in, and the enclosed rear entry porch adds everyday function--perfect for muddy boots, groceries, or easing into the house after a long Vermont day. Out back, the porch doubles as a relaxed hangout space, or step out onto the sun-filled deck for a bit more light and fresh air. It's an easy, inviting setup for morning coffee or winding down at the end of the day. Downstairs, a full basement provides solid storage or workspace potential, while the detached two-car garage--with workshop space and automatic openers--offers flexibility for projects, hobbies, or extra gear. The paved driveway, standing seam metal roof, and straightforward systems like the oil-fired hot water setup all point toward low-maintenance ownership--something buyers appreciate more and more. The home is being offered with key appliances already in place, including an electric range, refrigerator, microwave, washer, dryer, and dehumidifier, making for an easy transition whether you're just starting out or simplifying your next chapter. Set in one of Southern Vermont's most loved villages, this is the kind of property that works just as well as a first home as it does for downsizing. Simple, solid, and well-located--if Chester's been on your radar, this one's worth a closer look before it slips by. See MLS Property & Listing Details & 20 images.

$299,000 $201 per sq.ft. Chester VT Home »

Price Change! Reduced by $100,000 down 33% on June 2nd 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1488  |  Acres: 0.25
Saturday Sep 13, 2025
Description: Welcome to your dream home - This meticulously maintained and efficient New England-style gem is bursting with charm and modern convenience. Extra insulation, new windows and new hot water heater make this home as energy-efficient as it is beautiful. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by the gorgeous hardwood floors that add warmth and character to every room. Bask in the great natural light that fills every corner of this lovely abode, making every day feel bright and inviting. This home includes a main level bedroom, dining room and family room. In addition there is an attached garage and a barn for all your hobbies. This home is perfect for families and outdoor enthusiasts alike. Imagine being just a short stroll away from the village store for all your essentials and enjoying nearby skiing adventures in winter, along with shopping and restaurants year-round! Don't miss out on this incredible opportunity to own a piece of paradise in the heart of it all! Schedule your visit today and get ready to fall in love - your perfect home awaits! See MLS Property & Listing Details & 30 images.

$349,000 $195 per sq.ft. Chester VT Home »

Price Change! Reduced by $100,000 down 29% on May 7th 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.

$474,900 $360 per sq.ft. Chester VT Home »

Price Change! Reduced by $24,100 down 5% on May 19th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1320  |  Acres: 10.86
Thursday Apr 23, 2026
Description: MOTIVATED SELLERS welcome you to this meticulously maintained chalet in gorgeous Chester, Vermont! Private and secluded, direct access to VAST, located less than an hour from six renowned ski resorts and amenities. So many updates in the past two years; fully remodeled kitchen and bathrooms, fresh paint, new flooring along with numerous updates (list attached in associate documents); modern and cozy with so much charm! Nestled on over 10 acres, you will find walking trails, a fire pit and outbuildings on premises. Vaulted ceilings, open floor plan, lots of natural light and natural woodwork, this is a true move in ready beauty. The rooms are nicely sized and in close proximity to bathrooms. The wood burning fireplace brings a feeling of serenity on those chilly days. Fiber internet on site for those that work remotely. Town records state two bedrooms, however, the loft area has an en suite with a full bathroom and lots of closet space! Plenty of storage, full walkout basement gives ample space. This is one of those properties you won't want to miss on your home buying adventure! Truly a stunning property with so much to offer! See MLS Property & Listing Details & 60 images.

$479,000 $197 per sq.ft. Chester VT Home »

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

$569,000 $227 per sq.ft. Chester VT Home »

Price Change! Reduced by $26,000 down 5% on May 12th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 2966  |  Acres: 3.08
Monday Apr 20, 2026
Description: Tucked away at the end of a quiet cul-de-sac just one minute from the heart of town, this 4-bedroom retreat offers a rare blend of privacy, possibility, and connection to nature. Set on 3 mostly open acres with glimpses of the mountains and the soothing soundtrack of the nearby river, this is the kind of home that changes pace the moment you arrive. The heartbeat of the home comes from a bright and inviting great room that opens through sliding doors to an expansive deck where mornings begin with coffee and birdsong, and evenings end with the sound of rushing water under the stars. The flowing layout offers spaces that adapt beautifully to modern living -- a dedicated office for remote work, room for a home gym, studio, creative retreat, media lounge, or whatever your lifestyle calls for next. The dining room is ready for gatherings both large and small, while the attached 2-bay garage and generous outdoor space make everyday living feel effortless. Whether you're hosting friends, growing a garden, creating art, working from home, or simply looking for a peaceful place to recharge, this property offers the flexibility to make it your own. Private yet convenient, peaceful yet connected -- this home delivers a lifestyle that's increasingly hard to find. See MLS Property & Listing Details & 53 images.

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

3 Beds | 2 Baths |   Total Sq. Ft. 2205  |  Acres: 1.71
Thursday Jan 15, 2026
Description: Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views and sunsets. Indoors you'll find a tidy mudroom entry with space for all your year round gear. Tiled heated floors lead you to the kitchen featuring newer stainless steel appliances. Vaulted ceilings draw you towards the open dining/living room where you'll be bathed in end of the day sunlight. A bedroom and 3/4 bath round out the main floor. Upstairs you'll find two large bedrooms and a full bath. All good homes should have a family room and this doesn't disappoint. The lower walk out had a cozy spot with a large sectional to watch movies and is perfect for "hanging out" with friends. There is a work out area and a bonus room located on the lower level. This is definitely more than a ski home as there is plenty of outside living space. There is a shady front porch with begs for a rocking chair and a good book. Sun seekers will enjoy the rear deck which faces west and gets plenty of sunshine. Perennial gardens abound and offer color and character all summer long. There is a garage barn that can be used in a myriad of ways... park a car, use the workshop, store your toys... There is also an upstairs mostly finished room that can be your blank canvas. Visit the Okemo real estate community today. Taxes are based on current town assessment. See MLS Property & Listing Details & 60 images.

$209,900 $177 per sq.ft. Chesterfield NH Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1188  |  Acres: 5.1
Tuesday May 19, 2026
Description: This home has charming vintage character with endless potential to truly shine. Classic wood floors, detailed window and baseboard trim, and a cozy living room with a fireplace create a warm, inviting atmosphere. The layout includes two full baths for added convenience. Set on over 5 acres, the property offers a blend of open space and woods - for a myriad of uses. Please do not enter the barn. It is unsafe. See MLS Property & Listing Details & 21 images.

$335,000 $396 per sq.ft. Chesterfield NH Home »

Price Change! Reduced by $24,500 down 7% on May 11th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1378  |  Acres: 1.66
Thursday Apr 23, 2026
Description: Major Price Drop! This delightful, cozy and turn key country home offers practical and attractive interior space including such exciting features as updated kitchen and bathrooms, hardwood flooring, mini-split air conditioning and a lovely lower level renovated to include a third bedroom, office, large bath and laundry. The property is conveniently located on a rise of land above Rt. 9 and accessed by a shared driveway, within a short drive to crystal clear Spofford Lake and an easy commute to Keene, NH or Bratteboro, VT. A most desirable personal home...available at a great value price! See MLS Property & Listing Details & 23 images.

$385,000 $199 per sq.ft. Chesterfield NH Home »

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.

$430,000 $175 per sq.ft. Village of Spofford in Town of Chesterfield NH Home »

Price Change! Reduced by $20,000 down 5% on June 5th 2026
3 Beds | 3 Baths |   Total Sq. Ft. 2458  |  Acres: 2.41
Friday Apr 24, 2026
Description: Welcome to 65 Glebe Road in sought-after Spofford, NH--a contemporary home with a large 3-car garage. This gorgeous home is designed for comfort, functionality, and filled with natural light. Offering 3-4 bedrooms and 2.5 bathrooms, this home features a bright and inviting layout anchored by a stunning atrium in the living room, allowing sunlight to pour in and create a warm, open atmosphere you'll feel the moment you walk in. The main living space flows effortlessly, while the addition of mini-split systems provides efficient, year-round climate control for personalized comfort. Downstairs, you'll find two fully finished bonus rooms--each equipped with their own mini-split units. Whether you need a home office, gym, guest space, or creative studio, these flexible areas offer incredible versatility. The basement is further enhanced with spray foam insulation, and a new propane boiler system and tankless hot water heater (2022), adding to the home's overall energy efficiency and comfort. This property blends natural light, smart upgrades, and adaptable living space--65 Glebe Road is ready to meet you where you are and grow with you. See MLS Property & Listing Details & 46 images.

$529,000 $377 per sq.ft. Chesterfield NH Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1403  |  Acres: 3.37
Friday Jan 23, 2026
Description: To be built, new construction where you have the time to pick your colors, cabinets and granite counters. Three bedroom, two baths, open concept living with split bedroom plan in this one floor living home. The open living area has a cathedral ceiling and leads you out to the back covered farmers porch for great extended living. The primary has great storage and full bath. The builder has other options for home plans and the ability to make some changes to this one with alternative pricing for upgrades. This is an opportunity to have a new home where some of the decisions made come from years of professional experience and some where you can add items on your wish list to fit your needs and taste. The lot is entered off a shared driveway and tucked into the land with private well and septic. The house is built with to energy star standards. You are minutes to Brattleboro and close to Keene in an established neighborhood area. The photos are from a home currently being built in Swanzey NH with the same floor plan. Construction will start once the home is under contract. See MLS Property & Listing Details & 30 images.

$559,900 $252 per sq.ft. Chesterfield NH Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2224  |  Acres: 0.94
Thursday May 7, 2026
Description: Welcome to this immaculate Contemporary home, perfectly situated in one of Chesterfield's most sought-after neighborhoods. Conveniently located just a short drive to Keene, Vermont, and I-91, while also being moments from beautiful Spofford Lake, shopping, dining, and everyday conveniences. This beautifully maintained 3-bedroom, 3-bath home offers the perfect blend of comfort, style, and functionality. Step inside to gleaming hardwood floors throughout and a stunning brand-new kitchen completed in 2025, featuring stainless steel appliances, a farmhouse sink, and modern finishes designed to impress. The spacious front-to-back living room is warm and inviting, highlighted by a cozy gas fireplace -- the perfect place to unwind on cool New England evenings. A standout feature of the home is the oversized mudroom, office, or sitting area directly connected to the attached 2-car garage, creating flexible space for today's lifestyle needs. The first floor also offers convenient laundry, a powder room, and a generously sized dining room ideal for entertaining. Upstairs, the expansive primary suite includes a private bath and walk-in closet, while two additional bedrooms are serviced by a full bath. The heated basement offers endless possibilities for a home gym, playroom, hobby space, or additional storage. Outside, enjoy the covered back deck overlooking the fenced backyard -- an ideal setting for pets, children, gatherings, or simply relaxing in privacy. Additional features include a whole-house generator installed in 2025, ample parking, and a beautifully tucked-back setting that offers both peace and seclusion. This is truly a special home in an exceptional location -- offering the lifestyle you've been waiting for. 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.