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547 Andover Rd, Chester
$229,000
2 Beds ⋅ 1 Baths ⋅ 5112828 MLS
Sometimes, just the right amount of space is exactly what you need. Set on two pleasant acres in Chester, this tidy 2-bedroom, ¾-bath home offers comfortable, efficient one-level living with a practical layout that makes everyday life easy. Inside, the home is bright and well cared for, with a modern kitchen, comfortable living space, two nicely sized bedrooms, laundry, and the convenience of everything on one floor. Propane heat keeps things simple and efficient, while the manageable footprint means less house to maintain and more time to enjoy Vermont. Outside, the level lawn provides plenty of usable space for gardening, pets, a fire pit, or simply relaxing outdoors without taking on an overwhelming property. A detached two-car garage offers excellent parking, storage, and room for the tools and gear that come with Vermont living. Whether you're looking for a first home, ready to simplify, or searching for a comfortable retirement property with minimal stairs and manageable upkeep, this Chester home checks a lot of boxes. Simple, practical, and easy to maintain, it is a home that makes perfect sense.

547 Andover Rd, Chester
25 Villager Rd, Chester
$433,900
2 Beds ⋅ 2 Baths ⋅ 5112444 MLS
At The Villages at Chester, a private townhouse community, you come home to quiet private roads and a wooded recreation area, and the Association takes care of it all right down to the home’s exterior and even plowing your driveway and shoveling your walkway. Walk the wooded trails, spend summer at the pool, and book the clubhouse for your party. This end-unit townhouse has three finished levels, with hardwood throughout the first and second floors. The living room centers on a gas fireplace with a stacked-stone surround, prewired for a TV above. The dining room has a built-in corner cabinet and a slider out to a deck that runs the full width of the house, and nearly every window has a wooded view. The kitchen has knotty wood cabinets with a built-in wine rack, granite, stainless appliances, a five-burner gas stove and a peninsula with seating. The attached garage opens into a mudroom with a half bath and first-floor laundry. Upstairs, the large primary bedroom runs nearly the full depth of the house, with a vaulted ceiling, a skylight and a walk-in closet fitted out by California Closets with floor-to-ceiling shelving and drawers. The second bedroom is generous with two large windows, a ceiling fan and a double closet. A full bath with a double vanity connects the two, and a window seat in the hall looks out over your garden. Downstairs is the surprise. The finished lower level is carpeted and bigger than you'd expect, with a bonus room that stretches nearly the width of the house, full-size windows and a slider out to a patio and backyard. A separate room makes space for guests, or a workout area and another space ideal for an office or hobby room, and there’s the utility room and many closets for storage. Newer Andersen windows and a tankless water heater are already done. The HOA fee also covers trash, water and sewer. Pet-friendly community, and Chester keeps its small-town feel with horses and orchards nearby, and Pinkerton Academy for high school.

25 Villager Rd, Chester
3537 Popple Dungeon Rd, Chester
$249,900
2 Beds ⋅ 1 Baths ⋅ 5110600 MLS
Enjoy the beauty and charm of Vermont with this mobile home set on approximately 1 acre in Chester. Located across the road from a peaceful river, this property offers a wonderful setting for enjoying the outdoors and the natural beauty of the area. The property features an oversized 2 car garage with plenty of room for vehicles, recreational equipment, tools, and hobbies. Above the garage is finished bonus space, offering flexibility for a home office, studio, recreation room, guest area, or additional storage. This lot provides room to enjoy the outdoors, garden, entertain, or simply relax and take in the surrounding Vermont scenery. With the river just across the road, the property offers a special location for those looking to enjoy the tranquility and character of Chester. Come see what makes this Chester property special!

3537 Popple Dungeon Rd, Chester
56 Shepard Home Rd, Chester
$479,000
3 Beds ⋅ 1 Baths ⋅ 5107622 MLS
NEW PRICE! Enjoy peaceful riverfront living in this charming, light-filled Ranch with direct access to the Exeter River! Privately situated on a beautiful lot in Chester with no neighboring homes visible on either side, this property offers a wonderful blend of comfort and natural surroundings. Inside, you’ll find easy one-level living with 2–3 bedrooms, an updated kitchen, full bathroom, and a cozy wood stove for those chilly New Hampshire nights. The spacious deck overlooks the river, providing the perfect spot to relax, entertain, or enjoy the abundant wildlife. Fish from your backyard or launch a canoe when water levels allow! Additional features include a basement for storage& two sheds. Located outside the designated flood zone, this unique property is ideal for those seeking privacy, nature, and a relaxed lifestyle. Quick close possible!

56 Shepard Home Rd, Chester
159 Lower Bartonsville Rd, Chester
$255,000
3 Beds ⋅ 2 Baths ⋅ 5106226 MLS
Welcome to 159 Lower Bartonsville Road, a charming carriage house nestled along a scenic country farm road in Rockingham, Vermont, just moments from the picturesque restored Bartonsville covered bridge. This 3 bed, 1.5 bath property features authentic 1830s architecture and timeless rustic character, offering a solid structural foundation with much of its original detail preserved. Seamlessly blending old-world appeal with boundless equity-building potential, this quintessential New England abode serves as the perfect canvas for your personal touch. It is entirely ready for cosmetic enhancements, custom modern finishes, and tailored design choices that will allow you to completely personalize the space to match your unique vision. Just 15 minutes from I-91 and Springfield VT, 35 minutes to Keene, NH and 40 minutes to Lebanon NH. Stop on by and see it for yourself!

159 Lower Bartonsville Rd, Chester
3713 Trebo Rd, Chester
$289,900
3 Beds ⋅ 3 Baths ⋅ 5106191 MLS
Extremely well maintained and thoughtfully updated, this spacious three bedroom, two and a half bath home is privately nestled on 2.6 acres on a quiet dead end. Offering the convenience of single level living, the property has been meticulously cared for over the years, with numerous improvements that make it comfortable, efficient, and move in ready. Inside you’ll find generously sized rooms throughout, offering plenty of space for everyday living and entertaining. The home features a primary suite with its own private full bathroom with a soaking tub, two additional good sized bedrooms, another full bath, and a convenient half bath. The functional single level layout makes the home easy to enjoy, while the main living areas offer plenty of natural light and comfortable gathering space. The home has seen an impressive list of recent updates, including new kitchen flooring in 2021, a new roof and skylights in 2022, newer kitchen appliances, and a mini-split system installed in 2023. Additionally, a new hot water heater in 2025. Set on 2.6 acres, the property offers a peaceful and private setting while still providing convenient access to Chester and the surrounding area. With its spacious rooms, primary suite, 2.5 baths, single level living, extensive recent improvements, and exceptionally well-maintained condition, this is a home that has been cared for with attention to detail and is ready for its next owners to enjoy.

3713 Trebo Rd, Chester
3781 Flamstead Rd, Chester
$225,000
3 Beds ⋅ 2 Baths ⋅ 5102142 MLS
Nestled on 10 private acres between the towns of Chester and Springfield Vermont, this property offers an exceptional opportunity to build your dream home in a peaceful country setting. A driveway has already been installed, providing easy access to the center of the property where several potential homesites offer the possibility of beautiful mountain and valley views with selective clearing. An existing trailer on the property provides a convenient place to live or use as a base while planning and constructing your new home. With a blend of privacy, natural beauty, and existing improvements, this property is ready for you to bring your vision to life while remaining just minutes from shopping, dining, and year-round outdoor recreation. Selling as-is and needing at least 60 days to close. Also listed under MLS #5102143.

3781 Flamstead Rd, Chester
3668 Vt Route 103 N, Chester
$209,500
5097621 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
3668 Vt Route 103 N, Chester
$209,500
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
81 Main St, Chester
$445,000
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
3208 Green Mountain Tpke, Chester
$449,000
3 Beds ⋅ 2 Baths ⋅ 5095486 MLS
Located on the edge of the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines modern style with artisan craftsmanship. Set on .33± acres, this light-filled property features wide-pine floors, exposed beams, and a Vermont Castings woodstove enhancing an inviting open-concept living space. The kitchen/dining has butcher block counters, attractive center island with Vermont slate/stone counter, framed by a wall of windows with a picturesque valley view. A spacious first-floor bedroom and full bath with laundry 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. Walk to the market and charming village shops, antique stores and restaurants. Enjoy the recreation area, with its disc golf course, pickleball/tennis courts and sledding hill. Ideally located within 20 min. of Okemo Mountain Resort and Magic Mountain and within 40 min to Stratton or Bromley. This easy maintenance Vermont home is equally suited as a primary residence or second home.

3208 Green Mountain Tpke, Chester
1144 Potash Brook 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
64 Maple St, 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
663 Depot 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
40 Fenton Rd, Chester
$399,000
4 Beds ⋅ 3 Baths ⋅ 5073147 MLS
This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of living space 4 bedrooms, 2.5 bathrooms. It sits on the banks of the Williams River on a dead end street and treed backyard area. First floor consists of a large kitchen and livng room and a half bath. The second floor has a beautiful sized primary bedroom with ensuite bathroom. There are also 3 bedrooms and a 3/4 hallway bathroom.

40 Fenton Rd, Chester
3019 Popple Dungeon Rd, Chester
$169,000
1 Beds ⋅ 1 Baths ⋅ 5067929 MLS
Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny house while working on the original home. Consider the possibility of removing the older structure to make way for something new, or simply use the tiny house as your Vermont getaway. A stone walkway leads gracefully down to the river, providing a tranquil connection to nature. Both structures are believed to be elevated above the flood zone, ensuring peace of mind in all seasons. This lovely property is a nature lover's dream and a rare opportunity to embrace the essence of Vermont's natural beauty.

3019 Popple Dungeon Rd, Chester

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