Mreidrealestate.com Search Results

$579,900

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.

5090837 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.

197a Chester St, Chester

$1,450,000

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.

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

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.

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

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.

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

$138,000

Welcome to a place where the sound of the river becomes part of your daily rhythm. This 4.7-acre parcel with an end-of-road location offers an extraordinary 1,400 feet of frontage on the Williams River, creating a private and tranquil retreat just five minutes from the quintessential Vermont charm of Chester Village. The land unfolds beautifully: wide, flat, sun-filled fields stretch toward the river, softened by a scattering of mature trees that add shade, character, and seasonal color. Set along gentle bends in the river, the property feels open yet intimate, an ideal setting for gardens, gatherings, or simply relaxing under the sky. Wildlife is abundant here: deer grazing at dusk, fox weaving through the meadow, and birdsong drifting from the forest edge. A 33-foot camper is already positioned on the designated house site outside the floodplain, allowing you to enjoy the property from day one. Powered by a solar-supported electric generator and a gas generator, sleeps multiple people with a queen bed in the bedroom, 3 bunks in the bunkroom, and a couch and dining booth that convert to beds as well, and there is an inside and an OUTSIDE kitchen! It serves as the perfect basecamp while you plan your future build, or as a ready-made retreat just as it is. An 8' x 8' storage unit provides convenient space for kayaks, fishing gear, a mower, or all the toys that come with Vermont living. The house site, where the camper is located, sits entirely outside the floodplain and comes with an approved 4-bedroom wastewater permit and power at the road. While a portion of the land does lie within the floodplain, the property as a whole saw very little impact during the 2023 flood. This land offers a peacefulness that’s hard to find and impossible to replicate.

5090458 MLS

Welcome to a place where the sound of the river becomes part of your daily rhythm. This 4.7-acre parcel with an end-of-road location offers an extraordinary 1,400 feet of frontage on the Williams River, creating a private and tranquil retreat just five minutes from the quintessential Vermont charm of Chester Village. The land unfolds beautifully: wide, flat, sun-filled fields stretch toward the river, softened by a scattering of mature trees that add shade, character, and seasonal color. Set along gentle bends in the river, the property feels open yet intimate, an ideal setting for gardens, gatherings, or simply relaxing under the sky. Wildlife is abundant here: deer grazing at dusk, fox weaving through the meadow, and birdsong drifting from the forest edge. A 33-foot camper is already positioned on the designated house site outside the floodplain, allowing you to enjoy the property from day one. Powered by a solar-supported electric generator and a gas generator, sleeps multiple people with a queen bed in the bedroom, 3 bunks in the bunkroom, and a couch and dining booth that convert to beds as well, and there is an inside and an OUTSIDE kitchen! It serves as the perfect basecamp while you plan your future build, or as a ready-made retreat just as it is. An 8' x 8' storage unit provides convenient space for kayaks, fishing gear, a mower, or all the toys that come with Vermont living. The house site, where the camper is located, sits entirely outside the floodplain and comes with an approved 4-bedroom wastewater permit and power at the road. While a portion of the land does lie within the floodplain, the property as a whole saw very little impact during the 2023 flood. This land offers a peacefulness that’s hard to find and impossible to replicate.

250 Fenton Rd, Chester

$1,200,000

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.

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

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.

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

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.

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

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!

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

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.

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

$549,000

Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at day’s end. Step outside to a sunny, open lot with a peaceful pond, expansive deck ideal for entertaining, and a handsome shed for storage or hobbies. A recent fresh coat of interior paint and a newer high-efficiency boiler add modern reliability and make this home move-in ready. The large unfinished basement offers excellent potential for additional living space, a home gym, or a workshop. Ideally located near Okemo, Magic, and Stratton Mountains, with easy access to local dining, shops, and year-round recreation. This in a truly special location that is both private and practical.

4 Beds ⋅ 3 Baths ⋅ 5086105 MLS

Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at day’s end. Step outside to a sunny, open lot with a peaceful pond, expansive deck ideal for entertaining, and a handsome shed for storage or hobbies. A recent fresh coat of interior paint and a newer high-efficiency boiler add modern reliability and make this home move-in ready. The large unfinished basement offers excellent potential for additional living space, a home gym, or a workshop. Ideally located near Okemo, Magic, and Stratton Mountains, with easy access to local dining, shops, and year-round recreation. This in a truly special location that is both private and practical.

3341 Trebo Rd, Chester

$899,900

WOW No Cookie Cutter Here! Check Out this Stunning Contemporary Farmhouse in the Quintessential New England small town Of Chester, NH located in a fantastic Small Development with only 9 Detached Condo's. The home Features 3 beds,2 1/2 baths with an Open concept layout. The GORGEOUS Kitchen has all the bells and whistles, granite counter tops, a Huge island, stainless steel gas stove with vent hood that connects to a large living room with Gleaming Hardwoods floors. You are sure to Enjoy the Elegant Dining room adjacent to the kitchen along with a home office with French Doors. The 1st Floor Primary Suite has Hardwood floors and a STUNNING Tiled Shower, double Vanity, and a walk-in closet that also connects to the Laundry Room. The mud area and powder room complete the first level. Upstairs you will find a MASSIVE Bonus room that is sure to be an amazing place to entertain or just hang out with the family. The 2nd bedroom is Gigantic and can be another primary suite, it has a large walk-in closet and connects to a large full bathroom with double vanity. The 3rd bedroom is also Huge and connects to the full bathroom as well. Outside you have a huge deck and plenty of room for the kids or pets to run around. The massive basement provides tons of storage and space that is ready to finish. Quick Closing Possible. Some photos are Virtually Staged. This is a MUST SEE HOME !

3 Beds ⋅ 3 Baths ⋅ 5084563 MLS

WOW No Cookie Cutter Here! Check Out this Stunning Contemporary Farmhouse in the Quintessential New England small town Of Chester, NH located in a fantastic Small Development with only 9 Detached Condo's. The home Features 3 beds,2 1/2 baths with an Open concept layout. The GORGEOUS Kitchen has all the bells and whistles, granite counter tops, a Huge island, stainless steel gas stove with vent hood that connects to a large living room with Gleaming Hardwoods floors. You are sure to Enjoy the Elegant Dining room adjacent to the kitchen along with a home office with French Doors. The 1st Floor Primary Suite has Hardwood floors and a STUNNING Tiled Shower, double Vanity, and a walk-in closet that also connects to the Laundry Room. The mud area and powder room complete the first level. Upstairs you will find a MASSIVE Bonus room that is sure to be an amazing place to entertain or just hang out with the family. The 2nd bedroom is Gigantic and can be another primary suite, it has a large walk-in closet and connects to a large full bathroom with double vanity. The 3rd bedroom is also Huge and connects to the full bathroom as well. Outside you have a huge deck and plenty of room for the kids or pets to run around. The massive basement provides tons of storage and space that is ready to finish. Quick Closing Possible. Some photos are Virtually Staged. This is a MUST SEE HOME !

14 Stacey Ln Unit 2, Chester

$899,900

WOW Price Reduced ! No Cookie Cutter Here! Check Out this Stunning Contemporary Farmhouse in the Quintessential New England small town Of Chester, NH located in a fantastic Small Development with only 9 Detached Condo's. The home Features 3 beds,2 1/2 baths with an Open concept layout. The GORGEOUS Kitchen has all the bells and whistles, granite counter tops, a Huge island, stainless steel gas stove with vent hood that connects to a large living room with Gleaming Hardwoods floors. You are sure to Enjoy the Elegant Dining room adjacent to the kitchen along with a home office with French Doors. The 1st Floor Primary Suite has Hardwood floors and a STUNNING Tiled Shower, double Vanity, and a walk-in closet that also connects to the Laundry Room. The mud area and powder room complete the first level. Upstairs you will find a MASSIVE Bonus room that is sure to be an amazing place to entertain or just hang out with the family. The 2nd bedroom is Gigantic and can be another primary suite, it has a large walk-in closet and connects to a large full bathroom with double vanity. The 3rd bedroom is also Huge and connects to the full bathroom as well. Outside you have a huge deck and plenty of room for the kids or pets to run around. The massive basement provides tons of storage and space that is ready to finish. Quick Closing Possible. Some photos are Virtually Staged. This is a MUST SEE HOME !

3 Beds ⋅ 3 Baths ⋅ 5084557 MLS

WOW Price Reduced ! No Cookie Cutter Here! Check Out this Stunning Contemporary Farmhouse in the Quintessential New England small town Of Chester, NH located in a fantastic Small Development with only 9 Detached Condo's. The home Features 3 beds,2 1/2 baths with an Open concept layout. The GORGEOUS Kitchen has all the bells and whistles, granite counter tops, a Huge island, stainless steel gas stove with vent hood that connects to a large living room with Gleaming Hardwoods floors. You are sure to Enjoy the Elegant Dining room adjacent to the kitchen along with a home office with French Doors. The 1st Floor Primary Suite has Hardwood floors and a STUNNING Tiled Shower, double Vanity, and a walk-in closet that also connects to the Laundry Room. The mud area and powder room complete the first level. Upstairs you will find a MASSIVE Bonus room that is sure to be an amazing place to entertain or just hang out with the family. The 2nd bedroom is Gigantic and can be another primary suite, it has a large walk-in closet and connects to a large full bathroom with double vanity. The 3rd bedroom is also Huge and connects to the full bathroom as well. Outside you have a huge deck and plenty of room for the kids or pets to run around. The massive basement provides tons of storage and space that is ready to finish. Quick Closing Possible. Some photos are Virtually Staged. This is a MUST SEE HOME !

14 Stacey Ln Unit 2, Chester

$99,999

This property offers so many possibilities! Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn, ideal for storage, hobbies, or future expansion. As you move toward the back of the property, the land gently slopes up to a wooded hillside that levels out beautifully, creating a prime site to build your dream home. State wastewater permit WW-2-4040-1 approved for a 5-bedroom home.

5082636 MLS

This property offers so many possibilities! Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn, ideal for storage, hobbies, or future expansion. As you move toward the back of the property, the land gently slopes up to a wooded hillside that levels out beautifully, creating a prime site to build your dream home. State wastewater permit WW-2-4040-1 approved for a 5-bedroom home.

508 Mattson Rd, Chester

$119,000

Nestled in the picturesque hills of Chester, this inviting 7.95+/- acre property offers the perfect blend of privacy, beauty, and potential. Wander through a peaceful forest where moss covered stones, classic Vermont stone walls, and soft woodland light create a truly serene setting. With some thoughtful clearing, this parcel could open up to stunning views overlooking the charming fields and village below an ideal backdrop for your dream home or getaway retreat. Whether you’re looking to build, relax, or invest this property is sure to impress. Quiet, scenic, and full of Vermont character, this is a special piece of land where you can truly slow down and enjoy the surroundings—yet still be just a short drive from the heart of Chester.

5081034 MLS

Nestled in the picturesque hills of Chester, this inviting 7.95+/- acre property offers the perfect blend of privacy, beauty, and potential. Wander through a peaceful forest where moss covered stones, classic Vermont stone walls, and soft woodland light create a truly serene setting. With some thoughtful clearing, this parcel could open up to stunning views overlooking the charming fields and village below an ideal backdrop for your dream home or getaway retreat. Whether you’re looking to build, relax, or invest this property is sure to impress. Quiet, scenic, and full of Vermont character, this is a special piece of land where you can truly slow down and enjoy the surroundings—yet still be just a short drive from the heart of Chester.

Green Mountain Tpke, Chester

$175,000

Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and Vermont tranquility. The property features beautiful long-range views and a small pond with potential for expansion, creating a picturesque setting for your future home. Located in an area identified for development, it offers both a wonderful building site and long-term investment potential. The septic design is complete, and a 50-foot right-of-way is shown on the survey and is ready to be roughed-in. Bring in electricity, water, and septic, then start building your Vermont dream. Properties like this are increasingly hard to find: private, scenic and close to the heart of the village.

5079082 MLS

Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and Vermont tranquility. The property features beautiful long-range views and a small pond with potential for expansion, creating a picturesque setting for your future home. Located in an area identified for development, it offers both a wonderful building site and long-term investment potential. The septic design is complete, and a 50-foot right-of-way is shown on the survey and is ready to be roughed-in. Bring in electricity, water, and septic, then start building your Vermont dream. Properties like this are increasingly hard to find: private, scenic and close to the heart of the village.

377 Coach Rd, Chester

$799,900

2026 means a brand-new home! Welcome to the Condor Farmhouse at Pipit Estates. This popular house style offers a wonderfully welcoming and functional floor plan with room for everyone. The Eat-in Kitchen is perfect with granite counters, stainless steel appliances, and a large pantry. An extra "Flex Room" can be utilized as a formal Dining Room, Playroom, or perhaps an Office. The Mudroom with an entrance from the garage will be a handy space for all. 3 spacious Bedrooms, a Primary Bedroom with attached Bathroom, and a large Laundry Room complete the second floor. The full basement is a walk-out with slider and daylight windows, perfect to finish in the future for additional living space. Pet friendly community and no age restrictions. Beautiful country setting with over 16 acres of open space. Take advantage of all the charming town of Chester has to offer including a top-rated school system! There are additional floor plans to choose from including Ranch homes for single floor living.

4 Beds ⋅ 3 Baths ⋅ 5075427 MLS

2026 means a brand-new home! Welcome to the Condor Farmhouse at Pipit Estates. This popular house style offers a wonderfully welcoming and functional floor plan with room for everyone. The Eat-in Kitchen is perfect with granite counters, stainless steel appliances, and a large pantry. An extra "Flex Room" can be utilized as a formal Dining Room, Playroom, or perhaps an Office. The Mudroom with an entrance from the garage will be a handy space for all. 3 spacious Bedrooms, a Primary Bedroom with attached Bathroom, and a large Laundry Room complete the second floor. The full basement is a walk-out with slider and daylight windows, perfect to finish in the future for additional living space. Pet friendly community and no age restrictions. Beautiful country setting with over 16 acres of open space. Take advantage of all the charming town of Chester has to offer including a top-rated school system! There are additional floor plans to choose from including Ranch homes for single floor living.

12 Robin Way Unit 5, Chester

$74,500

Looking for a piece of Vermont to build a camp, cabin, ski home, full time residence, or create your own homestead? This piece is a clean slate that could be any of that! It has gentle slopes and flats for a potential building spots. Wooded and private, while being a short drive into lovely Chester, VT. This beautiful lot has so much potential, come take a look!

5074848 MLS

Looking for a piece of Vermont to build a camp, cabin, ski home, full time residence, or create your own homestead? This piece is a clean slate that could be any of that! It has gentle slopes and flats for a potential building spots. Wooded and private, while being a short drive into lovely Chester, VT. This beautiful lot has so much potential, come take a look!

Tbd Farrar Rd, Chester

$649,000

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.

3 Beds ⋅ 2 Baths ⋅ 5074094 MLS

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.

688 Hidden Heights Rd, Chester

$349,000

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.

3 Beds ⋅ 2 Baths ⋅ 5073930 MLS

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.

1397 Popple Dungeon Rd, Chester

$399,000

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.

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

$159,000

There are many ways to love Vermont and many ways to live here. This 5 acre parcel has a great open meadow perfect for a homestead farm, little get away cottage or a lovely lodge! Just build the lifestyle you want and forget the rest! A few minutes to Main Street Chester and the Common, A few more to the interstate, and nestled close to skiing, hiking and boating. The WWW permit is issued, town maintained road is easy access and power near by. It is the perfect time to escape, start a new beginning, or just take a weekend to breathe. Please call GMP and communications for availability and cost.

5069927 MLS

There are many ways to love Vermont and many ways to live here. This 5 acre parcel has a great open meadow perfect for a homestead farm, little get away cottage or a lovely lodge! Just build the lifestyle you want and forget the rest! A few minutes to Main Street Chester and the Common, A few more to the interstate, and nestled close to skiing, hiking and boating. The WWW permit is issued, town maintained road is easy access and power near by. It is the perfect time to escape, start a new beginning, or just take a weekend to breathe. Please call GMP and communications for availability and cost.

00 Contro Rd, Chester

$169,000

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.

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

$1,500,000

Builders take notice! This is a rare opportunity you don’t want to miss out on with over 200 acres of undeveloped land in beautiful Chester. Sold together - there are 7 parcels; Tax Map 2 Lots 29, 30, 31, 31-1, 33, 38-1 and lot 39. Road frontage along Pomp Road and all land is in current use. Buyer to pay any fees when taking it out of current use status. Buyer to do their due diligence. Aerial photos coming soon. Also for sale is additional 483 acres in Derry, NH -see MLS 4890183 for more information.

4890134 MLS

Builders take notice! This is a rare opportunity you don’t want to miss out on with over 200 acres of undeveloped land in beautiful Chester. Sold together - there are 7 parcels; Tax Map 2 Lots 29, 30, 31, 31-1, 33, 38-1 and lot 39. Road frontage along Pomp Road and all land is in current use. Buyer to pay any fees when taking it out of current use status. Buyer to do their due diligence. Aerial photos coming soon. Also for sale is additional 483 acres in Derry, NH -see MLS 4890183 for more information.

Jack Rd, Chester

$74,000

Bring your ideas for building your own home on this 15.5 acre parcel of land in the quintessential town of Chester. Located minutes to the 91 FWY. Vermont Academy nearby along with several hiking and snowmobile trails. Seller has included the cost for clearing the building site and a driveway to house site. Come look at this property and enjoy all it has to offer.

5061671 MLS

Bring your ideas for building your own home on this 15.5 acre parcel of land in the quintessential town of Chester. Located minutes to the 91 FWY. Vermont Academy nearby along with several hiking and snowmobile trails. Seller has included the cost for clearing the building site and a driveway to house site. Come look at this property and enjoy all it has to offer.

00 Remington Rd, Chester

$650,000

Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously designed, incorporating reclaimed materials that add warmth and charm to the contemporary aesthetic. In addition to the inviting residential spaces, this property includes a versatile two-story commercial area currently occupied by a successful, established business making it ideal for investors or entrepreneurs. With prominent visibility and high traffic flow, the commercial space is well-suited for a variety of ventures, from retail to office use. Situated just a short drive from Okemo Mountain, this property offers year-round appeal for outdoor enthusiasts and tourists alike. Plus, it is conveniently located near the vibrant shops, dining options, and recreational activities of Chester and Ludlow. This versatile property allows for multiple avenues of income - whether you choose to occupy one of the residential units, rent both out, or utilize the commercial space, the possibilities are endless. Don't miss your chance to own a piece of this thriving community.

5044879 MLS

Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously designed, incorporating reclaimed materials that add warmth and charm to the contemporary aesthetic. In addition to the inviting residential spaces, this property includes a versatile two-story commercial area currently occupied by a successful, established business making it ideal for investors or entrepreneurs. With prominent visibility and high traffic flow, the commercial space is well-suited for a variety of ventures, from retail to office use. Situated just a short drive from Okemo Mountain, this property offers year-round appeal for outdoor enthusiasts and tourists alike. Plus, it is conveniently located near the vibrant shops, dining options, and recreational activities of Chester and Ludlow. This versatile property allows for multiple avenues of income - whether you choose to occupy one of the residential units, rent both out, or utilize the commercial space, the possibilities are endless. Don't miss your chance to own a piece of this thriving community.

3630 Vt Route 103 N, Chester

$290,000

Discover the true meaning of "getting away from it all" at 1175 Quarry Road. This expansive 75 acre parcel is tucked away a full mile up a quiet, dead end dirt road in the desirable town of Chester. Mostly wooded with rising topography. It’s an ideal canvas for a private homestead, a hunting camp, or a seasonal getaway. You get the peace of a dead end road with the convenience of being near four local ski mountains. Land of this scale and privacy is increasingly rare. Come explore and see the potential for yourself. Conveniently located 15 minutes to I-91, Under 30 minutes to Okemo, Bromley and Magic Mountain and under an hour to Stratton and Killington.

5058824 MLS

Discover the true meaning of "getting away from it all" at 1175 Quarry Road. This expansive 75 acre parcel is tucked away a full mile up a quiet, dead end dirt road in the desirable town of Chester. Mostly wooded with rising topography. It’s an ideal canvas for a private homestead, a hunting camp, or a seasonal getaway. You get the peace of a dead end road with the convenience of being near four local ski mountains. Land of this scale and privacy is increasingly rare. Come explore and see the potential for yourself. Conveniently located 15 minutes to I-91, Under 30 minutes to Okemo, Bromley and Magic Mountain and under an hour to Stratton and Killington.

1175 Quarry Rd, Chester

$249,000

84+/- Acres with Stunning Mountain Views in Chester, Vermont Discover a breathtaking property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this property embodies the best of quintessential Vermont countryside living. A perfect horse property with an outdoor arena and lots of dirt roads for trail riding. The land includes several open meadows, perfect for future development, homesteading, or recreation. Enrolled in Vermont’s Current Use Program, the property is both environmentally and financially sustainable. A section of the land was selectively logged, creating a network of trails and plateaus, ideal for hiking, wildlife exploration, or building opportunities. This property offers unparalleled potential for dream homes, private retreats, or as an investment in Vermont real estate. Don’t miss the chance to own this unique Vermont land with its stunning mountain views and incredible development possibilities.

5023272 MLS

84+/- Acres with Stunning Mountain Views in Chester, Vermont Discover a breathtaking property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this property embodies the best of quintessential Vermont countryside living. A perfect horse property with an outdoor arena and lots of dirt roads for trail riding. The land includes several open meadows, perfect for future development, homesteading, or recreation. Enrolled in Vermont’s Current Use Program, the property is both environmentally and financially sustainable. A section of the land was selectively logged, creating a network of trails and plateaus, ideal for hiking, wildlife exploration, or building opportunities. This property offers unparalleled potential for dream homes, private retreats, or as an investment in Vermont real estate. Don’t miss the chance to own this unique Vermont land with its stunning mountain views and incredible development possibilities.

000 Green Mountain Tpke, Chester