$445,000 $115 per sq.ft. Chester VT Home »

Price Change! Reduced by $30,000 down 7% on August 23rd 2026
5 Beds | 4 Baths |   Total Sq. Ft. 3865  |  Acres: 0.44
Thursday Jun 18, 2026
Description: Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning fireplace and a large entertainment room complete with a wet bar, creating an ideal setting for gatherings, celebrations, or relaxing at home. The thoughtfully designed primary suite features a beautiful en-suite bathroom, while first-floor laundry adds everyday convenience. The flexible floor plan provides abundant space for family, guests, remote work, hobbies, or multi-generational living. Outside, a paved driveway leads to a detached one-car garage, and the level backyard offers plenty of room for recreation, gardening, pets, or outdoor entertaining. Mature trees and established landscaping create a natural buffer from the road, providing a sense of privacy while remaining just moments from Chester's village amenities, shops, restaurants, and community events. Combining historic character, generous living space, and a highly desirable location, this is a rare opportunity to own one of Chester's classic homes. Conveniently located just minutes from I-91 and within easy reach of Okemo Mountain Resort, Magic Mountain, Bromley Mountain, Stratton Mountain, and other Southern Vermont outdoor destinations, this property offers year-round access to skiing, hiking, recreation, and travel throughout the region. See MLS Property & Listing Details & 58 images. Includes a Virtual Tour

$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

$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.

$485,000 $255 per sq.ft. Chesterfield NH Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1905  |  Acres: 1.5
Tuesday Aug 11, 2026
Description: Storybook Craftsman on 1.5 Parklike Grounds. This former residence of the childrens' author Charles Tazewell was completely renovated in 2017. Elegant one floor living with beautiful finishes. Granite countertops and stainless steel appliances with pantry cupboards in the kitchen. All systems have been updated. A gazebo with ceiling fan and light compliments the stunning landscaping. Two car garage and central AC round out the property amenities. Convenient to both Keene and Brattleboro. See MLS Property & Listing Details & 29 images.

$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.

$449,000 $340 per sq.ft. Chittenden VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1320  |  Acres: 2.8
Sunday Aug 23, 2026
Description: YOUR VERMONT ADVENTURE BEGINS AT YOUR DOORSTEP! Since 2002, this charming custom-built furnished home has been the setting for countless memories, and now it is ready for its next chapter. Tucked away in a private Chittenden setting with direct access to the VAST Trail, this delightful three-bedroom, two-bath, one-level home is the perfect size for a year-round residence or Vermont getaway. Snowmobile for miles along groomed trails, explore wonderful walking and hiking paths, or spend your days kayaking and swimming at the nearby Chittenden Reservoir. After a day of adventure, relax on the deck overlooking the fire pit and Green Mountains, or unwind on the welcoming front porch. Situated on 2.88 acres among other attractive private homes, this well-maintained property offers comfort, convenience, and easy access to everything outdoor enthusiasts love about Vermont. The renowned Mountain Top Inn and Resort is just minutes away, offering fine dining on the patio overlooking the reservoir, horseback riding, and cross-country skiing. Chittenden is also home to Barstow Memorial School and offers high school choice, an attractive benefit for many families. Killington Resort, known as the Beast of the East, is within easy reach, while nearby Rutland provides farmers' markets, restaurants, shopping, and everyday conveniences. Custom-built and lovingly enjoyed by the current owners, this special home is ready for someone new to create lasting memories. Simply arrive, settle in, and start enjoying the Vermont lifestyle. See MLS Property & Listing Details & 32 images.

$485,000 $309 per sq.ft. Chittenden VT Home »

Price Change! Reduced by $10,000 down 2% on August 14th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 2100  |  Acres: 3
Friday Jul 24, 2026
Description: Welcome to your ideal Vermont retreat at 224 Holden Road! Nestled on 3 private, mostly flat wooded acres in popular Chittenden, this beautifully maintained classic Cape offers the perfect blend of peaceful seclusion and convenient accessibility. Step inside to find an inviting open floor plan designed for effortless entertaining and quality time. The main level delivers the convenience of true first-floor living, featuring a bedroom, full bathroom, and laundry. Upstairs, two additional generously sized bedrooms and a second full bath provide plenty of space for everyone. The basement offers versatile bonus rooms, perfect for a home office, gym, or game room. Relax on the expansive western view back deck and take in breathtaking sunset views over a neighboring horse pasture, serene ponds, and the majestic mountains. The open yard is ideal for recreation and comes complete with its own unique, fully powered custom treehouse! A detached two-car garage provides excellent shelter and extra storage for outdoor gear. Located in a community that is served by Barstow Elementary and Middle schools, and offers coveted high school choice, this location is an outdoor enthusiast's paradise. You are just 10 minutes from the Chittenden Reservoir, 20 minutes from the Paramount Theatre in Rutland, and under 30 minutes from world-class skiing at Killington Resort. Perfect as a full-time residence or a quintessential Vermont getaway! See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$270,000 $177 per sq.ft. Claremont NH Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1528  |  Acres: 0.22
Monday Jul 13, 2026
Description: Same owner for 43 years! This charming 3-bedroom, 2¼-bath bungalow offers the perfect opportunity to make a well-loved home your own. Situated on .22 acres in a convenient in-town location, the property features beautiful perennial flower gardens, a paved driveway, and an attached two-car garage. Inside, you'll find a functional kitchen with room for a small island, a formal dining room that could serve as a dining room, office, or additional living area. A spacious living room perfect for relaxing or entertaining, and an enclosed porch, the perfect spot to enjoy your morning coffee or tea. An additional ¼ bath (toilet only) for added convenience. Upstairs offers three bedrooms with large closets and a full bathroom. The primary bedroom offers the potential for a private bathroom, with existing plumbing in place. Buyer to verify condition and suitability with a licensed plumber. The roof is only one year old, providing peace of mind for years to come. Come see the possibilities and make this long-time family home your own! See MLS Property & Listing Details & 33 images.

$275,000 $162 per sq.ft. Claremont NH Home »

4 Beds | 1 Baths |   Total Sq. Ft. 1701  |  Acres: 0.19
Thursday Jul 30, 2026
Description: Spacious and well-maintained 4-bedroom, 1-bath home with a 1-car garage in the heart of Claremont. This charming home features an updated kitchen and full bath, beautiful hardwood floors, and two main-level bedrooms for added convenience. Upstairs, both bedrooms offer large walk-in closets. Recent updates include wood stove, updated appliances, countertops, renovated bathroom, water heater, and a Roth oil tank. Conveniently located near shopping, restaurants, local amenities, and riding trails, this move-in-ready home offers comfort, character, and convenience. Open House 8/7/2026 at 5-7pm See MLS Property & Listing Details & 28 images.

$284,900 $150 per sq.ft. Claremont NH Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1900  |  Acres: 0.5
Wednesday Aug 26, 2026
Description: There is a lot to like about 108 Old Church Road. Set along a country road on the outskirts of Claremont, this solid New England home offers a great combination of character, usable outdoor space and room to grow. The home feels updated without losing the character of the original home. Upstairs, additional unfinished attic space offers future expansion possibilities for someone looking for more room down the road. Outside, the level yard is framed by mature trees and offers plenty of space to garden, entertain or simply enjoy the setting. A small detached outbuilding adds another fun and useful element - think workshop, hobby room, tree house, creative space or a quiet place to work away from the main house. With good solid bones, a metal roof, flexible extra space and easy access to Claremont, I-91 and the Upper Valley, this is the kind of property that gives the next owner plenty to work with while still being comfortable and enjoyable from day one. One of the owners is a licensed realtor. See MLS Property & Listing Details & 18 images.