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$749,000
4 Beds ⋅ 2 Baths ⋅ 5101760 MLS
Discover the perfect blend of rustic elegance and modern versatility at 34 Edwards Mill Road. Set on 3.89 expansive acres in the scenic countryside of Chester, NH, this stunning log home offers a serene lifestyle for any stage of life. Are you looking for a natural playground where you can explore the woods and the soothing waters of Towle Brook, or wanting a peaceful New Hampshire retreat with single-level living potential, this property delivers. The spacious interior has been thoughtfully maintained with fresh paint, featuring 9 spacious rooms including 4 bedrooms and 2 full bathrooms. The home’s flexible layout includes a first floor primary bedroom suite that opens directly into a gorgeous huge sunroom. For those prioritizing convenience, the first-floor separate laundry room facilitates true single-level living options. Recent updates ensure peace of mind, including log maintenance, new gutters, and freshly seal-coated driveway. Outdoor enthusiasts and hobbyists will fall in love with the substantial detached 3-car garage which features a brand-new roof, a convenient drive-through bay with heat and water access. Above, an enormous unfinished space presents incredible potential for a studio, storage, or an accessory dwelling unit (ADU), subject to approvals. Outside, the enormous 50 ft. deck provides the ultimate spot for hosting gatherings or simply relaxing to the sounds of the brook winding through your private acreage. Experience total privacy without sacrificing accessibility; this retreat is located just 25 minutes from the Massachusetts border and approximately one hour from the heart of Boston. This home has been lovingly cared for and is ready for its next chapter. Schedule your private tour today to experience the charm & serenity of this stunning Chester retreat. You won't want to leave.

34 Edwards Mill Rd, Chester
$925,000
5 Beds ⋅ 3 Baths ⋅ 5099745 MLS
Escape to the charm of Vermont in this spacious 5-bedroom, 3-bath country home, perfectly set amidst open meadows with a picturesque swim pond and peaceful surroundings. Designed for both everyday living and entertaining, this inviting property offers the perfect balance of rustic character and modern comfort. Step inside through the practical mudroom, where you'll be welcomed by a dramatic family room featuring soaring vaulted ceilings, a cozy wood-burning stove, and a loft overlooking the space. The heart of the original 1860's home is the open-concept living area, complete with a well-appointed kitchen, dining area, and a warm, inviting living room centered around a classic wood-burning fireplace. The main level also features a convenient half bath and a private primary suite with a ¾ bath. From the primary bath, step directly onto the back deck and unwind in the sunken hot tub while taking in the tranquil country setting. Second level, you'll find four additional bedrooms, a full bath, and a comfortable den/loft overlooking the family room, offering flexible space for guests, a home office, or recreation. Outside, enjoy Vermont's beauty from the private covered porch, gather around the expansive yard, or relax by the stone firepit or scenic pond surrounded by open meadows. An attached garage provides ample storage, while the finished game room above creates the perfect space for entertaining, hobbies, or additional guest accommodations. The flat meadows were the perfect setting for the family's recent wedding... What event will you host in this incredible backyard? Ideally located just minutes from the charming village of Chester and within easy reach of Okemo Mountain Resort, this exceptional property offers year-round enjoyment, whether you're seeking a full-time residence, a vacation getaway, or an investment opportunity. Visit the Okemo real estate community today. Taxes are based on town assessment.

1470 Popple Dungeon Rd, Chester
$199,000
2 Beds ⋅ 1 Baths ⋅ 5098053 MLS
Set on 18 forested acres along quiet, dead-end Potash Brook Road in Chester, this peaceful cabin offers a simple and inviting Vermont retreat with no through traffic and a true sense of calm. Well suited for a hunting camp, recreational getaway, or quiet place to unwind, the property provides privacy, natural surroundings, and easy access to the outdoor lifestyle Southern Vermont is known for. The cabin includes propane heat, a spring well, septic, and an inviting and cozy living space for weekends, seasonal use, or time away from the noise of everyday life. The structure will require new footings and is being sold as is, offering an opportunity for the next owner to make needed improvements while enjoying the land, setting, and existing cabin. The property is wooded and rustic in feel, with room to explore, observe wildlife, and enjoy the changing seasons. A brook runs through the land, adding natural character to the setting. Whether used as a base for hunting, hiking, snowmobiling, skiing, or simply relaxing in the woods, this property offers a practical and appealing Vermont escape. Ski areas, trail networks, fishing, and year-round recreation are all within reach, while the setting itself remains quiet, private, and refreshingly simple. If you are looking for land, privacy, and a modest cabin with key systems already in place, this Chester retreat is well worth a look.

1372 Potash Brook Rd, Chester
$850,000
4 Beds ⋅ 3 Baths ⋅ 5097911 MLS
Looking for a 4-bed colonial in Chester with space, privacy, and an ideal layout for entertaining? Welcome to 43 Emerson Road Where timeless Colonial charm meets comfortable everyday living. This well-maintained home set on two private acres is in a desirable cul-de-sac neighborhood. Enjoy spacious living areas, inviting outdoor spaces. Nestled on 2 private acres in a peaceful cul-de-sac neighborhood, this 4-bedroom, 3-bathroom Colonial offers the perfect balance of privacy, community, and convenience. The open and inviting first floor is designed for both daily living and entertaining, featuring a spacious kitchen, formal dining room, and an expansive family room with a soaring vaulted ceiling and cozy gas fireplace. New carpeting adds a fresh touch, making this home move-in ready. Step outside to your own backyard retreat featuring a multi-tiered deck, sparkling pool, and a private outdoor oasis designed for summer gatherings, barbecues, and relaxing evenings with family and friends. The generous two-acre lot provides room to play, garden, or simply enjoy the peaceful natural surroundings. Not far from shopping, dining, recreation, and major commuter routes while still offering the charm and tranquility that make Chester one of southern New Hampshire's desirable communities. Served by the highly regarded Pinkerton Academy school district. Whether you're hosting memorable celebrations or enjoying quiet evenings at home, this property delivers the lifestyle you've been searching for. Come experience everything 43 Emerson Road has to offer and discover why so many are proud to call Chester home. Schedule your private showing today. Showings begin Monday July 6, 2026

43 Emerson Rd, Chester
$649,000
3 Beds ⋅ 2 Baths ⋅ 5097737 MLS
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!

168 Chandler Rd, Chester
$750,000
3 Beds ⋅ 2 Baths ⋅ 5097722 MLS
Tucked away on a quiet country road in one of Chester’s most coveted areas, this striking contemporary home offers the ultimate Vermont lifestyle, just miles from the Okemo Mountain base lodge. Embraced by nature and thoughtful landscape, the property seamlessly connects refined indoor living with the natural beauty of its private riverfront, complete with your own summer swimming hole. Inside, the main level centers around a commanding, floor-to-ceiling fieldstone wood-burning fireplace, beautifully complemented by rich hardwood floors and a bespoke custom kitchen. Designed for privacy, the primary suite features a spa-like ensuite bath, while two additional guest bedrooms and a 3/4 bath provide plenty of space for family or weekend visitors. Intelligently designed for flexible living, the upper-level loft serves as an inspiring home office or studio, while the bright, walk-out lower level offers incredible potential for a game room, home gym, or ski lounge. Transition effortlessly outdoors to the oversized front deck for morning coffee, or unwind in the expansive screened porch out back listening to the sound of the river. The detached, insulated, oversized, 2-bay, 2-level barn has full electrical service, electric garage doors, and a workshop with extra storage space. There is a greenhouse perfect for gardening. With direct access to nearby VAST trails for winter recreation, this is a true four-season retreat. Visit the Okemo real estate today. Taxes are based on the current town assessment.

955 Smokeshire Rd, Chester
$875,000
4 Beds ⋅ 3 Baths ⋅ 5097711 MLS
50K PRICE CUT! OPEN HOUSE | 11AM to 1PM | Sunday, July 26th, 2026 Welcome to 88 Crawford Road, a breathtaking residential haven nestled in the heart of Chester, New Hampshire. The Property This exquisite colonial estate seamlessly blends sophisticated architectural design with the tranquil beauty of its lush, private surroundings. Offering an expansive 3,675 square feet of meticulously crafted living space, the residence features 4 generously appointed bedrooms and 2.5 elegant bathrooms. From the grand, winding driveway to the majestic facade framed by mature trees, every detail of this home exudes luxury. The interior promises unparalleled comfort with expansive room layouts, high-end finishes, and an abundance of natural light pouring through magnificent feature windows. Location & Drivability Perfectly situated for those who demand both privacy and convenience, 88 Crawford Road offers an idyllic retreat without sacrificing accessibility. Located in the charming, historic town of Chester, you are mere minutes from top-rated local schools, pristine parks, and boutique community dining. For commuters, the property provides seamless access to major regional routes, putting the bustling commercial hubs of Manchester and Salem within easy driving distance, while offering a straightforward, scenic commute to downtown Boston and the gorgeous New Hampshire seacoast.

88 Crawford Rd, Chester
$249,500
4 Beds ⋅ 3 Baths ⋅ 5097620 MLS
Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits. The home is currently configured as two charming apartments, each showcasing timeless character with features such as stained-glass windows, soaring ceilings, and abundant natural light. The first-floor apartment boasts a beautiful brick fireplace with a classic hearth in the kitchen and opens directly onto a private patio, creating a warm and inviting living space. The impressive barn includes a heated workshop area, making it ideal for artisans, contractors, mechanics, or anyone needing year-round workspace. Whether you're looking to establish a small business, expand your existing operation, or simply enjoy the flexibility of extensive storage and workspace, this property offers endless possibilities. Conveniently located on Route 103 between Chester, Springfield, and Ludlow, the property provides excellent visibility, easy access, and ample parking for customers, clients, and guests.

3668 Vt Route 103 N, Chester
$789,000
5 Beds ⋅ 3 Baths ⋅ 5097600 MLS
Exceptional design, enduring craftsmanship, and an unrivaled Vermont setting define this remarkable custom residence on 11± beautifully landscaped acres just a short stroll from the village of Chester. Offering more than 3,600 square feet of thoughtfully designed living space, the home was built to an exacting standard where quality materials, timeless architecture, and exceptional attention to detail create a residence as enduring as it is beautiful. A flexible floor plan offers five bedrooms and three baths, including an elegant first-floor primary suite with ensuite bath, complemented by additional main-level bedroom options ideal for guests, multi-generational living, or a dedicated home office. Upstairs, two spacious bedrooms each feature adjoining bonus rooms perfectly suited as executive offices, dressing rooms, studios, or generous walk-in closets, while additional unfinished space presents exciting opportunities for future expansion. Designed for effortless entertaining and comfortable everyday living, the heart of the home is an open-concept kitchen, dining, and living area filled with natural light. A handsome library offers a quiet retreat, while integrated whole-home audio enhances the experience throughout. An oversized laundry and mudroom connects seamlessly to the attached two-car garage, delivering exceptional convenience without compromising design. Outside, mature gardens, specimen trees, and thoughtfully curated outdoor living spaces create a setting of remarkable beauty and privacy. Relax beneath the covered porch, entertain with family and friends, or simply enjoy the peaceful surroundings. Ideally located just minutes from Okemo, Stratton, Magic, and endless four-season recreation, yet within walking distance of Chester's vibrant village, this exceptional property offers a rare combination of privacy, convenience, and refined Vermont living. A home of lasting quality, exceptional versatility, and unmistakable character!

223 Coach Rd, Chester
$599,000
4 Beds ⋅ 2 Baths ⋅ 5096954 MLS
DON'T MISS THIS RARE OPPORTUNITY! One level living / Multigenerational opportunity. Discover this hard-to-find Ranch-style home set on two beautiful, level acres with exceptional backyard privacy in the heart of Chester's highly sought-after equestrian community. Properties like this don't come along often! This spacious 4-bedroom, 2-bath home offers desirable southern exposure across the backyard, creating the perfect setting to relax on the deck or porch while enjoying stunning sunsets. Inside, you'll find a large living room featuring a classic brick-hearth wood-burning fireplace and expansive hardwood floors that add warmth and timeless appeal. The main level includes three generously sized bedrooms with hardwood flooring, a full bath, and the convenience of first-floor laundry. The kitchen is well-appointed with stainless steel appliances, granite countertops, two pantry cabinets, and stylish recessed and pendant lighting. A bonus family room leads to the attached two-car garage, while the private primary suite above the garage features a sitting area, creating the perfect retreat at the end of the day. The full basement offers excellent potential for additional finished living space, giving you room to grow. Outside, the expansive level lot provides endless possibilities for entertaining, gardening, or enjoying the peaceful surroundings. The pool will require a new liner and possibly a new filter. ENTS & BUYERS to do their own Due Diligence to verify all listing information. Room sizes are for reference only; not guaranteed.

224 Haverhill Rd, Chester
$510,000
3 Beds ⋅ 2 Baths ⋅ 5096706 MLS
STAY-CATION LIVING IS CALLING. Nestled on a gorgeous, private, flat acre in Chester, this home delivers the outdoor lifestyle you've been dreaming of. Pull into the paved driveway and you'll already see it - the lush landscaping, the natural shade, and a backyard that's pure paradise. Three sheds plus a detached garage with partially finished bonus space give you room for all your gear and then some. Step inside through the foyer and you're greeted by warm wood floors and natural light throughout. The open concept kitchen features an island, updated cabinets, and a gas range - ideal for cooking after a long day outside. It opens to a cozy family room with a wood fireplace, one of TWO fireplaces in the home. Heat with propane, wood or electric baseboard. The half bath and laundry are conveniently tucked on the main level. Upstairs, the living room and dining area offer flexible everyday space, and the top floor holds the primary suite with a walk-in closet, a second bedroom with its own large closet, and a completely renovated full bath for both bedrooms to share. The middle floor is designed for a three-bedroom configuration — easy to convert back. Now for the MAIN EVENT: the backyard. Above-ground pool. Hot tub. Garden space. Deck. This is where summers happen. NEW SEPTIC & LEACH FIELD and 2-year-old heating system mean the big-ticket items are already done. Pinkerton Academy district. Book your tour today!

111 Shepard Home Rd, Chester
$825,000
3 Beds ⋅ 3 Baths ⋅ 5096334 MLS
The Eagle Farmhouse blends a classic colonial layout with a fresh, modern exterior. Step inside and you'll love the spacious open-concept design, perfect for both everyday living and entertaining. The kitchen features beautiful quartz countertops, ample cabinetry, and a seamless flow into the main living areas. Conveniently located off the garage, the mudroom provides the perfect drop zone for coats, shoes, and everyday essentials. A versatile den offers an ideal space for a home office, playroom, or guest area, while the inviting family room provides plenty of room to relax and gather with family and friends. Thoughtfully designed with comfort and functionality in mind. The second floor offers two spacious bedrooms with walk-in closets, a dedicated laundry room, a full bath, and a spacious primary with en suite with a lovely tiled walk-in shower designed to satisfy even the most discerning homeowner. The full basement could be finished later for future additional living space if desired. Pet friendly and no age restrictions. Come and see what this charming community of 8 detached condos in desirable Chester, NH has to offer. Last lot left - do not miss out! Home should be ready late Summer/early Fall.

Lot 2 Lot 2 Robin Way Unit 2, Chester
$450,000
5 Beds ⋅ 4 Baths ⋅ 5095551 MLS
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.

81 Main St, Chester
$489,000
3 Beds ⋅ 2 Baths ⋅ 5095486 MLS
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 marble 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.

3208 Green Mountain Tpke, Chester
$495,000
3 Beds ⋅ 2 Baths ⋅ 5095371 MLS
This well-maintained property in Chester is in close proximity to many of Vermont's best ski mountains. It is not likely that you would drive by this property without it catching your eye. From the meticulous grounds with beautiful trees to the Vermont native stone wall lining the road, to the established perennial beds to the paved driveway leading back to this pleasing home with an attached garage. This light-filled home with two floors of living (plus a multi-room lower-level walkout ready to finish) has great open space on the main level. The kitchen with updated granite counters is open to the dining area which has a sliding door to the large back deck. This is the perfect space to have dinner overlooking the landscaped back yard. Try your green thumb in the vegetable garden that is ready for planting. The living room is also connected to the dining area making this space perfect for friends and family to gather. A convenient bedroom and bathroom complete this level. Upstairs are two generous bedrooms, a bonus room for a home office or more plus space above the garage that is currently being used as an amazing walk-in closet. Come and take a look at this low-maintenance home in a park-like setting with berry bushes, fruit trees, a gazebo, and a combination garden and wood shed. The stone firepit could be a favorite spot for relaxing by the fire after a day on the slopes. There is a third bay workshop next to the attached garage and an additional detached garage that has a vent pipe for a wood stove and can be of multiple uses. This property will check boxes that you didn't even know you had!

3078 Vt Route 10, Chester
$875,000
3 Beds ⋅ 3 Baths ⋅ 5095331 MLS
Collectors, auto or motorcycle enthusiasts or those needing an ADU take notice! Classic Country Colonial with Farmers Porch on lovely almost 6 acre lot; Sunroom with gas fireplace, cathedral ceiling and fan; Combination Dining/Kitchen with induction cooking stove and plenty of cabinets, fan and hardwood flooring; 1st floor Half bath with laundry; Formal Dining Room with wainscoting and hardwood floors; Spacious Living Room with hardwood floors; Primary bedroom with 3/4 bath, carpet, fan and 2 closets; 2nd Bedroom with fan and carpet; 3rd Bedroom with fan and carpet; Full Bath off hall; Heated 2 Car Attached Garage with storage above; Detached 3+ Car 2 story Garage with large bay doors, rear garage door and unfinished 2nd level for ADU potential! The detached garage footings will support a lift if desired! This one owner home has central air conditioning and extra space for expansion or storage.

15 Town Farm Rd, Chester
$635,999
4 Beds ⋅ 2 Baths ⋅ 5094684 MLS
Your Dream Backyard is here! Welcome to this beautifully renovated 4-bedroom, 2-bath home situated on a private 1-acre lot in desirable Chester, New Hampshire. Combining modern updates, exceptional outdoor living, and pride of ownership throughout, this move-in-ready property is one you won’t want to miss. Inside, you’ll find a stunning new kitchen, updated bathrooms, new flooring, fresh paint, and a finished lower level offering flexible living space for today’s lifestyle. Every improvement has been thoughtfully completed, creating a home that is both stylish and functional. Step outside to enjoy your own backyard retreat featuring a beautiful in-ground pool with a brand-new pool liner, a spacious new deck of Primary Bedroom, and plenty of room for entertaining family and friends. The home also features new siding, updated windows, and a detached oversized 3-car garage. Lovingly maintained and meticulously cared for, this home offers peace of mind and true turnkey living. 4 Bedrooms 2 Full Bathrooms Fully Renovated Interior Finished Lower Level New Kitchen & Bathrooms New Flooring Throughout Fresh Paint New Siding Updated Windows Newer Roof Brand-New Deck In-Ground Pool with New Pool Liner Detached 2-Car Garage Private 1-Acre Lot Exceptionally Well Maintained Move-In Ready Whether you’re relaxing poolside, hosting gatherings , or enjoying the privacy of your acre lot, this property offers the perfect place to call home. Chester, NH

632 Raymond Rd, Chester
$75,000
2 Beds ⋅ 1 Baths ⋅ 5093286 MLS
Nice country spot with older mobile home on it. Property is located in a flood zone so if removed could not be replaced with a permanent structure. Power, septic and electric on sight along with a 1 car garage. Home could be repaired, would also make a great spot for a snowbird wanting a spot in Vermont or anyone looking to park an RV. Property is sold AS IS CASH ONLY

1144 Potash Brook Rd, Chester
$2,000,000
4 Beds ⋅ 4 Baths ⋅ 73531137 MLS
Discover exceptional luxury living at 32 Colby Farm Road, a custom-designed 5,110-square-foot farmhouse set on a picturesque one-acre homesite in Chester, New Hampshire. Thoughtfully crafted with high-end finishes and timeless design, this stunning home features dual primary suites, including a first-floor retreat with heated bathroom floors, two walk-in closets, and private deck access. The chef’s kitchen is equipped with premium Thermador appliances, an oversized island, quartz surfaces, and a fully appointed butler’s pantry. Additional highlights include two laundry rooms, a private office, media room, expansive great room, walkout lower level with future expansion potential, and a three-car garage with 12-foot ceilings. This home offers the perfect balance of privacy and convenience. Located minutes from Route 93, Manchester-Boston Regional Airport, and major commuter routes, Boston is approximately 50 minutes away and Manchester-Boston Regional Airport, and major commuter routes.

32 Colby Farm Rd, Chester
$425,000
4 Beds ⋅ 2 Baths ⋅ 5092775 MLS
Bank on Market due to buyer financing, this will go quickly! Investors, flippers and DIY enthusiasts, here is your opportunity to bring this magnificent Federal Colonial back to life! Located in picturesque Chester and built in 1795, this home offers over 3500 square feet of historic charm. Fireplaces adorn many of the rooms, and you’ll find unique features such as built-in cabinets and more. The first floor offers many layout possibilities, including multiple rooms that could serve as a dining room, living room, office, or bedroom. Upstairs are spacious bedrooms. Much of the home has wide pine flooring, and other attractive historic features. The wood siding is in good shape and most windows are newer as well. Situated on over 4 acres, the property features a large, level yard with garden areas. This home needs a full renovation, and the buyer is responsible for performing their own due diligence on all repairs. Property is being sold as-is, cash only.

55 Chester St, Chester
$600,000
3 Beds ⋅ 2 Baths ⋅ 5092425 MLS
If you're looking for a tranquil, move-in-ready 3-bedroom home nestled on 3.77 wooded acres, your search is over! Enjoy the peaceful surroundings from the brand-new 12' x 16' deck—the perfect spot to relax with a book and take in nature. This beautifully remodeled home offers worry-free living with a new roof, new windows, a stunning new kitchen featuring leathered granite countertops, soft-close cabinetry, and stainless steel appliances, plus two completely renovated bathrooms. Thoughtfully updated throughout, this property combines modern comforts with the privacy and serenity of a wooded setting. Don't miss the opportunity to own this turnkey retreat that feels miles away from it all while still providing the conveniences of home. Agent Interest

51 Halls Village Rd, Chester
$1,450,000
3 Beds ⋅ 4 Baths ⋅ 5090829 MLS
Most ranch homes play it safe. This one doesn't. Tucked at the end of a cul-de-sac with conservation land bordering the back and one side, 51 Colby Farm Road was built for people who actually thought about how they wanted to live — and then built it that way. The double-sided gas fireplace is the first thing that stops you. Open to both the living room and dining room, it's the kind of feature that makes you rethink every home you've ever been in. The kitchen keeps the momentum going: gas cooktop, microwave/oven combo, glass-front cabinets, and an island big enough to mean it. Integrated surround sound and a full smart home system mean the music follows you room to room and everything else just works — lights, climate, security, all of it from the palm of your hand. The primary suite is its own world — his and hers walk-in closets, with her closet featuring its own island with drawers, a private screened-in porch just off the bedroom perfect for morning coffee or an evening glass of wine while the sun sets over the conservation land, and a bathroom with dual sinks, a makeup area, an oversized shower, and a private water closet. Two additional bedrooms share a full bath, a half bath is right where you need it, and the laundry closet has an actual folding area because someone here was thinking clearly. Then there's the garage. Three bays, 10-foot ceilings, custom shelving and storage throughout — the kind of space that makes grown adults emotional. Above it, a full bonus room with its own bathroom that can become whatever you need it to be. And when it comes to storage, the easily accessible attic delivers — a quiet, surprisingly beautiful space that makes staying organized feel effortless. Outside, a farmer's porch out front and a large deck out back with piped gas to both the grill and the fire pit — an entertainer's dream from the inside out. Conservation land behind you and along one side. Quiet. Private. Real. This is the one you come back to.

51 Colby Farm Rd, Chester
$579,900
2 Beds ⋅ 2 Baths ⋅ 5090733 MLS
This property presents a rare opportunity to own a large lot on desirable Chester St. Many options here: Update the house and create a huge farm property, build a new house and use the existing house as an ADU/cottage or other, subdivide into two lots with town approvals ** A beautiful country setting for this 16.4+/- acre farm with wooded areas to explore. ** This classic farmhouse offers 2 bedrooms, 2 baths, large eat-in kitchen, laminate, tile and soft wood floors. NEWER forced hot water boiler. Many farm features: Chicken coop, fenced in areas, 20x24 2-stall horse pole barn, a large barn that was moved to the property from another site in Chester. Peaceful, yet conveniently located, about 8.5 miles to Exit 4 I-93 and about 6.9 miles to Exit 2 Route 101. About Chester ** WASON POND is where residents can go to enjoy a quiet, natural place to walk, hike, cross-country ski, walk dogs, kayak, picnic, and swim. SCHOOLS: Consists of elementary & middle school, Chester Academy and the High School is Pinkerton Academy, in Derry. SCARECROWS: The town has been going scarecrow crazy for many years. Every October there are over 400 scarecrows placed all over town with a map showing the locations. The scarecrows will be on display through Oct. 31. HALLOWEEN NIGHT: Brings many visitors to Chester Street, where over the years Trick or Treat has become a must-see event. AGENTS & BUYERS to do their own Due Diligence to verify all listing information and verify options with town and necessary approvals to do so. Room sizes are for reference only; not guaranteed. *** House being sold in current condition and all items on the property to remain after month-to-month tenant leaves. House is tenant occupied and works from the house.

197 Chester St, Chester
$1,900,000
4 Beds ⋅ 4 Baths ⋅ 5090572 MLS
Some homes check boxes. This one rewrites the list entirely. 32 Colby Farm Road is a 5,100 sq ft modern farmhouse on a pristine acre in one of Chester's most exclusive new subdivisions. From the sweeping farmers porch to the last carefully chosen finish, every detail tells you this one is different. Inside, 9-ft ceilings, hardwood floors, a custom coffered 10-ft ceiling in the family room, and a vaulted wood ceiling in the sunroom create a main level that's as warm as it is impressive. The kitchen is a chef's dream: Thermador 48" gas range, dual fuel oven, oversized hood, and 42" built-in refrigerator, backed by a fully equipped scullery with its own oven, sink, and dishwasher. Entertaining here isn't just easy,it's genuinely fun. The main-floor primary suite is pure retreat, with a private deck and a spa bath featuring radiant heated floors, a frameless glass shower with dual rain heads, marble bench and surround, brushed gold fixtures, and a freestanding soaking tub. Yes, all of that. Upstairs delivers just as much — a second primary suite, two additional bedrooms, movie room, second laundry, a common bath with dual vanities and a separate toilet and shower room, and an oversized bonus room with in-law or au pair suite potential. And then there's the walkout basement — bright, open, and full of possibility. French doors and oversized windows flood the space with natural light, making it feel anything but like a basement. Already pre-plumbed for both a full bathroom and a kitchen, the groundwork is laid for whatever you envision — a guest suite, home gym, recreation room, or a fully independent living space. Few homes at this level offer this kind of potential right out of the gate. The 3-car garage has 11-ft ceilings, and a large rear deck is ready for every gathering you've been meaning to host. This is the home people drive by and wonder about. Now's your chance to stop wondering.

32 Colby Farm Rd, Chester
$210,000
4 Beds ⋅ 2 Baths ⋅ 73520586 MLS
Colonial style home featuring 8 rooms, 4 bedrooms and 2 bathrooms located on 6+ acre lot.

1 Crane Rd, Chester
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 5088175 MLS
Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation. Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting gathering spaces designed for relaxed country living. The heart of the home is the warm and welcoming country kitchen featuring soapstone counters, a center island, and ample room for entertaining. A large living room with a pellet stove creates a cozy retreat after a day on the slopes or trails, while the den offers an ideal space for a home office or quiet study. The screened front porch captures the essence of Vermont living perfect for morning coffee, evening conversations, and taking in the peaceful surroundings. Outdoors, enjoy evenings around the fire pit beneath star filled skies, surrounded by the natural beauty and privacy of the property. A standout feature is the remarkable multi-level 55’ x 40’ barn, full of rustic character and endless potential. Having hosted countless gatherings and celebrations, it offers incredible space for entertaining, hobbies, storage, or future creative use. Tucked away just two miles from town, this serene retreat offers both privacy and convenience, with easy access to skiing, snowmobiling, hiking, and all the outdoor adventure and small town charm that make Vermont so special.

76 Goldthwaite Rd, Chester
$325,000
4 Beds ⋅ 3 Baths ⋅ 5087965 MLS
Some properties just radiate a certain warmth, charm and magic and this home is definitely one of them. Imagine sitting on the front porch and listening the soft rustle of the willow tree leaves and the babbling brook trickling by, then you step inside and feel that you have walked into a home that was truly loved. The large kitchen offers nice upgrades including tile floor, granite countertops and appliances. The main level offers a bedroom, dining room, office space and living room. All of the windows have been replaced (except in the attic), updated electric panel, insulation done by Efficiency VT, new stoves in the barn room and living room (see MLS docs for the complete list). This property is perfect for anyone looking for a TRUE Vermont home with loads of potential. Great natural light, large bedrooms, hardwood floors and attached garage. One of the features I personally love is the screened stone patio (barn room) off the back of the house. The rustic beams and barn boards with wood stove is a wonderful space to relax and entertain. Above is unfinished space ready for your ideas, work out space? yoga studio? game room? There are pretty perennials and gardens surrounding the home. The back yard is private with attached shed space and back deck. Chester is a wonderful community and this home is perfectly situated for easy access to I91, Grafton, ski resorts, shopping and walking to the village green. The sellers have loved owning this home and have created many many memories here. Don't miss your chance to be the next stewards of this truly special property.

397 River St, Chester
$1,490,000
5 Beds ⋅ 5 Baths ⋅ 5087874 MLS
Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design. Inside, the home is defined by warm, handcrafted details wide plank wood floors, paneled walls, layered moldings, and reclaimed beams create a sense of comfort and authenticity throughout. The scale and layout offer a balance of inviting gathering spaces and quieter rooms, well suited for both everyday living and hosting. Originally operated as a bed and breakfast, the home was thoughtfully designed to welcome guests while maintaining a natural flow and sense of privacy. The surrounding land provides a peaceful and private setting, with stone walls, established gardens, wildflowers, fruit trees, and a blueberry patch woven into the natural landscape. Open areas and wooded sections create a property that feels both curated and comfortably natural, offering space to explore, relax, and enjoy Vermont’s changing seasons. A guest house and dedicated woodworking barn add to the property’s appeal, offering flexibility for hosting, hobbies, or creative pursuits. Ideally located near the charming village of Chester, the property offers convenient access to year-round outdoor recreation, including skiing, hiking, biking, fishing, and scenic trails. Throughout the home, the builder’s attention to detail is unmistakable, with thoughtfully crafted custom woodwork and timeless finishes that reflect a genuine commitment to quality and design. Quiet, private, and rooted in tradition, this is a property well suited for those seeking a classic Vermont retreat and lifestyle.

1302 Popple Dungeon Rd, Chester
$469,000
3 Beds ⋅ 3 Baths ⋅ 5087175 MLS
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!

64 Maple St, Chester
$390,000
3 Beds ⋅ 2 Baths ⋅ 5086202 MLS
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.

663 Depot St, Chester

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