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11 Derry Rd, Chester

You pull up to a quiet cul-de-sac, the noise of the world already fading behind you. A COVERED PORCH waits at the front door, the kind you actually use. Step inside and you'll know: this is the one. Nestled in Chester's Shaker Heights Estates, this meticulous MOVE-IN READY townhouse checks every box and then some. Pride of ownership shines through every room. The open main level welcomes you with gleaming hardwood floors and NATURAL LIGHT pouring in from every angle. The eat-in kitchen, a generous 17x15, features stainless steel appliances and flows right into the dining area, making everyday meals and weekend entertaining equally effortless. The living room is HUGE at 24x16 with a private DECK. Step outside, breathe in the wooded views, and make it your morning coffee spot or evening wind-down zone. A half bath and FIRST-FLOOR LAUNDRY round out the main level. Upstairs, two OVERSIZED bedrooms impress. The primary suite spans 24x16 with a private bath and walk-in closet, and the second bedroom at 20x18 has its own walk-in closet too. Everyone gets their own space here. Head downstairs to a FINISHED REC ROOM with daylight windows and walkout access - perfect for hobbies, a home gym, movie nights, or extra storage. The garage is OVERSIZED. Big enough to fit a truck and all the toys and tools you need. Out back, enjoy a patio in a wooded, country setting. HOA covers landscaping, water, sewer, plowing, and trash - truly low-maintenance living. Won't last!

2 Beds ⋅ 3 Baths ⋅ 5092343 MLS

You pull up to a quiet cul-de-sac, the noise of the world already fading behind you. A COVERED PORCH waits at the front door, the kind you actually use. Step inside and you'll know: this is the one. Nestled in Chester's Shaker Heights Estates, this meticulous MOVE-IN READY townhouse checks every box and then some. Pride of ownership shines through every room. The open main level welcomes you with gleaming hardwood floors and NATURAL LIGHT pouring in from every angle. The eat-in kitchen, a generous 17x15, features stainless steel appliances and flows right into the dining area, making everyday meals and weekend entertaining equally effortless. The living room is HUGE at 24x16 with a private DECK. Step outside, breathe in the wooded views, and make it your morning coffee spot or evening wind-down zone. A half bath and FIRST-FLOOR LAUNDRY round out the main level. Upstairs, two OVERSIZED bedrooms impress. The primary suite spans 24x16 with a private bath and walk-in closet, and the second bedroom at 20x18 has its own walk-in closet too. Everyone gets their own space here. Head downstairs to a FINISHED REC ROOM with daylight windows and walkout access - perfect for hobbies, a home gym, movie nights, or extra storage. The garage is OVERSIZED. Big enough to fit a truck and all the toys and tools you need. Out back, enjoy a patio in a wooded, country setting. HOA covers landscaping, water, sewer, plowing, and trash - truly low-maintenance living. Won't last!

15 Shaker Heights Ln, Chester

54 Fremont Rd Unit Unit A and Unit B, Chester

$429,000

Investment opportunity! For the cash Buyer only. This 2 unit duplex boasts 7.22 acres, long secluded driveway. Renters intact. Each unit has 2 spacious bedrooms, kitchen and dining combo, spacious living room . All bedrooms and full bathroom are upstairs and 1/2 bath off kitchen. Kitchen has fridge, dishwasher and stove. Laundry hookups are in the walk out basement. All electric heat and hotwater heater. Newer roof, new siding, new decks, new asphalt driveway. Renters are responsible for cable, and electric.

5070453 MLS

Investment opportunity! For the cash Buyer only. This 2 unit duplex boasts 7.22 acres, long secluded driveway. Renters intact. Each unit has 2 spacious bedrooms, kitchen and dining combo, spacious living room . All bedrooms and full bathroom are upstairs and 1/2 bath off kitchen. Kitchen has fridge, dishwasher and stove. Laundry hookups are in the walk out basement. All electric heat and hotwater heater. Newer roof, new siding, new decks, new asphalt driveway. Renters are responsible for cable, and electric.

54 Fremont Rd Unit Unit A and Unit B, Chester

$425,000

Absolutely stunning architecture located just steps from the village green and across the road from the historic Congregational Church. This property has five apartments. The kitchen appliances are included in each and there is a shared washer and dryer available for tenant use. Each of the five units has its own 100-amp electric panel box. The heat is a central, oil fired boiler providing baseboard heat with separate thermostats in each unit. Hot water is a central water heater. The building is handsome with its wrap around porch and columns. There once was a commercial unit in the bottom right side of the house and the individual door and unique windows are still in place. Many historic features are still intact such as hand split lathe, woodwork, flooring, cupboards, hardware and more, but there are some new windows and other updates. There is a very large barn that perhaps has the potential for four additional apartments or storage. Large yard for play or gardens. Ample parking. Easy walk to school, shops, restaurants, and the town recreation area. Bring your ideas....investment rentals, create condos, develop the barn, or what? Easy to show. 24-hour notice needed for one apartment; the others are ready to show.

5034061 MLS

Absolutely stunning architecture located just steps from the village green and across the road from the historic Congregational Church. This property has five apartments. The kitchen appliances are included in each and there is a shared washer and dryer available for tenant use. Each of the five units has its own 100-amp electric panel box. The heat is a central, oil fired boiler providing baseboard heat with separate thermostats in each unit. Hot water is a central water heater. The building is handsome with its wrap around porch and columns. There once was a commercial unit in the bottom right side of the house and the individual door and unique windows are still in place. Many historic features are still intact such as hand split lathe, woodwork, flooring, cupboards, hardware and more, but there are some new windows and other updates. There is a very large barn that perhaps has the potential for four additional apartments or storage. Large yard for play or gardens. Ample parking. Easy walk to school, shops, restaurants, and the town recreation area. Bring your ideas....investment rentals, create condos, develop the barn, or what? Easy to show. 24-hour notice needed for one apartment; the others are ready to show.

423 Main St, Chester

$424,900

Spacious open concept ranch on 1.89 acres zoned C1 Commercial with road frontage on Route 102 and Towle Road. Welcoming front to back living room with an office area and egress leading to the back yard. Step up into the dining room and updated kitchen with quartz countertops, cherry cabinets and stainless steel appliances. Front bedroom is private and the back bedroom has its own full bath. There is a large laundry room with cabinets, full bath and a utility room. Private back yard with raised garden beds and shed. Home has several updates including roof, siding, windows, kitchen, water treatment system, driveway and so much more. Quick close is possible for this great property in an amazing location. You will be pleasantly surprised at the open floor plan once you enter and with a little TLC, you can make it your own! Showings begin on Wednesday 11/5/25.

2 Beds ⋅ 2 Baths ⋅ 5068488 MLS

Spacious open concept ranch on 1.89 acres zoned C1 Commercial with road frontage on Route 102 and Towle Road. Welcoming front to back living room with an office area and egress leading to the back yard. Step up into the dining room and updated kitchen with quartz countertops, cherry cabinets and stainless steel appliances. Front bedroom is private and the back bedroom has its own full bath. There is a large laundry room with cabinets, full bath and a utility room. Private back yard with raised garden beds and shed. Home has several updates including roof, siding, windows, kitchen, water treatment system, driveway and so much more. Quick close is possible for this great property in an amazing location. You will be pleasantly surprised at the open floor plan once you enter and with a little TLC, you can make it your own! Showings begin on Wednesday 11/5/25.

11 Towle Rd, Chester

$420,000

Welcome to this beautifully updated raised ranch, thoughtfully designed for both relaxed day-to-day living and effortless entertaining. Step inside to an open-concept main level bathed in natural light, anchored by rich hickory hardwood floors that flow throughout. At the heart of the home, the renovated kitchen shines with modern finishes, a classic apron-front farmhouse sink, and stainless steel appliances. Relax by the gas fireplace in the inviting living room, highlighted by soaring vaulted ceilings and rustic exposed wood beams. Accommodating family and guests with ease, the layout features 5 generous bedrooms and 2 updated baths. The primary suite acts as your own private sanctuary, complete with an ensuite bath featuring a double vanity, and a private balcony. The flexible lower-level bonus space easily adapts to your lifestyle - ideal for a home gym, media room, or private office. Outdoor living is a breeze while you're relaxing bug-free on the screened porch! Tucked away on a quiet dead-end street, this turn-key residence pairs privacy with convenience with an easy walk to the vibrant Chester Green. Additional highlights include the boiler replaced in 2021, the freshly painted interior in 2022, new windows installed throughout the house in 2021 and 2025, a new sump pump installed in 2023, and a newly paved driveway in 2024. Electrical updates and a full foundation restoration have been completed in 2026 for long-term structural integrity (inquire for more information or see under Attached Documents), providing peace of mind for years to come. Don't miss your chance to own this move-in ready gem in a prime Chester location!

5 Beds ⋅ 2 Baths ⋅ 5082995 MLS

Welcome to this beautifully updated raised ranch, thoughtfully designed for both relaxed day-to-day living and effortless entertaining. Step inside to an open-concept main level bathed in natural light, anchored by rich hickory hardwood floors that flow throughout. At the heart of the home, the renovated kitchen shines with modern finishes, a classic apron-front farmhouse sink, and stainless steel appliances. Relax by the gas fireplace in the inviting living room, highlighted by soaring vaulted ceilings and rustic exposed wood beams. Accommodating family and guests with ease, the layout features 5 generous bedrooms and 2 updated baths. The primary suite acts as your own private sanctuary, complete with an ensuite bath featuring a double vanity, and a private balcony. The flexible lower-level bonus space easily adapts to your lifestyle - ideal for a home gym, media room, or private office. Outdoor living is a breeze while you're relaxing bug-free on the screened porch! Tucked away on a quiet dead-end street, this turn-key residence pairs privacy with convenience with an easy walk to the vibrant Chester Green. Additional highlights include the boiler replaced in 2021, the freshly painted interior in 2022, new windows installed throughout the house in 2021 and 2025, a new sump pump installed in 2023, and a newly paved driveway in 2024. Electrical updates and a full foundation restoration have been completed in 2026 for long-term structural integrity (inquire for more information or see under Attached Documents), providing peace of mind for years to come. Don't miss your chance to own this move-in ready gem in a prime Chester location!

176 Meadow Rd, Chester

$402,239

Looking for your dream Vermont escape? Look no further than this unique and spacious home conveniently located between the towns of Chester and Ludlow. The main floor has a master bedroom, bathroom, dining room, kitchen, and two large living rooms complete with wood burning fireplace. Upstairs are 3 more bedrooms, a bathroom, 2 large bonus rooms, 2 lofts for office, storage, or playroom space, and a book nook with a couch overlooking the main floor living room. Outside you will find a recently added stone patio with wood and propane fireplace, deck, hot tub under cover, a 20kw standby propane generator. Other great updates include a brand new roof, egress windows, newer mini splits for a/c and heat in each bedroom, paved driveway. Lots of furnishings will stay with the house, so just bring your suitcase and skis/snowboards and you are ready for the season! Magic, Okemo, Bromley, and Stratton are not far away! Don't wait, schedule your appointment today to see this beauty!

4 Beds ⋅ 2 Baths ⋅ 5064343 MLS

Looking for your dream Vermont escape? Look no further than this unique and spacious home conveniently located between the towns of Chester and Ludlow. The main floor has a master bedroom, bathroom, dining room, kitchen, and two large living rooms complete with wood burning fireplace. Upstairs are 3 more bedrooms, a bathroom, 2 large bonus rooms, 2 lofts for office, storage, or playroom space, and a book nook with a couch overlooking the main floor living room. Outside you will find a recently added stone patio with wood and propane fireplace, deck, hot tub under cover, a 20kw standby propane generator. Other great updates include a brand new roof, egress windows, newer mini splits for a/c and heat in each bedroom, paved driveway. Lots of furnishings will stay with the house, so just bring your suitcase and skis/snowboards and you are ready for the season! Magic, Okemo, Bromley, and Stratton are not far away! Don't wait, schedule your appointment today to see this beauty!

4877 Vt Route 103, Chester

$400,000

3 Beds ⋅ 2 Baths ⋅ 5082867 MLS

51 Halls Village Rd, Chester

$400,000

Historically known as the Frank Harris House, this distinguished circa 1880 Queen Anne style Victorian commercial building on .75+/- acres has long been a landmark presence in the village of Chester. With its welcoming veranda and timeless charm, the property has served as a thriving office for many years and has many period architectural details throughout such as, a unique, colored transom window in the first floor meeting room, a white brick decorative fireplace with accent mirror in the large office/reception area, graceful bay windows, a mix of hardwood and softwood floors and a slate roof with diamond patterned bands. The heating system has recently been upgraded with a new propane direct vent boiler and efficient hydronic wall units to ensure comfort throughout the seasons. Additional features include a spacious kitchen area, 1.5 baths, a handicap access ramp and public water and sewer. The attached rustic two-story barn offers additional storage space and there is a large, second story three-season porch! Whether your vision involves refreshing the property for use as office space, transforming it to a multi-unit investment property or restoring it to a grand, single family home, the Harris House presents a rare opportunity—centrally located in the heart of Chester and within walking distance to the town green, shops, elementary school and recreation area.

5058558 MLS

Historically known as the Frank Harris House, this distinguished circa 1880 Queen Anne style Victorian commercial building on .75+/- acres has long been a landmark presence in the village of Chester. With its welcoming veranda and timeless charm, the property has served as a thriving office for many years and has many period architectural details throughout such as, a unique, colored transom window in the first floor meeting room, a white brick decorative fireplace with accent mirror in the large office/reception area, graceful bay windows, a mix of hardwood and softwood floors and a slate roof with diamond patterned bands. The heating system has recently been upgraded with a new propane direct vent boiler and efficient hydronic wall units to ensure comfort throughout the seasons. Additional features include a spacious kitchen area, 1.5 baths, a handicap access ramp and public water and sewer. The attached rustic two-story barn offers additional storage space and there is a large, second story three-season porch! Whether your vision involves refreshing the property for use as office space, transforming it to a multi-unit investment property or restoring it to a grand, single family home, the Harris House presents a rare opportunity—centrally located in the heart of Chester and within walking distance to the town green, shops, elementary school and recreation area.

26 Main St, Chester

$379,000

Set on .76 acres in the peaceful Chester VT countryside, this former schoolhouse offers timeless farmhouse charm, rich history, and a setting that feels both private and inviting. Framed by classic stone walls, a pond site, and a gently wooded backdrop, the home sits just off a main road, providing easy access to town while maintaining a quiet, pastoral atmosphere. Originally serving the community as a schoolhouse until the early 1960s, the property was thoughtfully converted into a residence that honors its roots while offering comfortable modern living. The original schoolroom now anchors the home as a warm, open living space filled with natural light, where hardwood floors and tall windows create an airy yet cozy environment ideal for everyday living and gathering. The farmhouse-style kitchen flows seamlessly into the living area and features butcher block countertops, a professional-grade gas convection range with double ovens, and a breakfast bar with a charming pass-through window, perfect for casual meals and entertaining. A spiral staircase adds rustic character and leads to the upper level, offering a spacious bedroom or studio and flexible use for guests, creative space, or a private retreat. The primary suite serves as a peaceful sanctuary with vaulted ceilings, custom built-in shelving, a private full bath, and a cozy wood stove. Doors open to a rear deck overlooking the private yard and surrounding countryside. Additional features include a generous first-floor laundry area, enclosed sun porch, outdoor patio, a private hot tub with a heated walkway for truly maintenance-free winter access (no shoveling, ever!) and an attached two-car garage currently used as a game room, easily adapted back to garage space or reimagined as a workshop, studio, or home office. With commercial zoning, just 10 minutes from Okemo Mountain Resort, and a history as a successful Airbnb, this rare property offers character, flexibility, income potential, and true country charm.

2 Beds ⋅ 2 Baths ⋅ 5074728 MLS

Set on .76 acres in the peaceful Chester VT countryside, this former schoolhouse offers timeless farmhouse charm, rich history, and a setting that feels both private and inviting. Framed by classic stone walls, a pond site, and a gently wooded backdrop, the home sits just off a main road, providing easy access to town while maintaining a quiet, pastoral atmosphere. Originally serving the community as a schoolhouse until the early 1960s, the property was thoughtfully converted into a residence that honors its roots while offering comfortable modern living. The original schoolroom now anchors the home as a warm, open living space filled with natural light, where hardwood floors and tall windows create an airy yet cozy environment ideal for everyday living and gathering. The farmhouse-style kitchen flows seamlessly into the living area and features butcher block countertops, a professional-grade gas convection range with double ovens, and a breakfast bar with a charming pass-through window, perfect for casual meals and entertaining. A spiral staircase adds rustic character and leads to the upper level, offering a spacious bedroom or studio and flexible use for guests, creative space, or a private retreat. The primary suite serves as a peaceful sanctuary with vaulted ceilings, custom built-in shelving, a private full bath, and a cozy wood stove. Doors open to a rear deck overlooking the private yard and surrounding countryside. Additional features include a generous first-floor laundry area, enclosed sun porch, outdoor patio, a private hot tub with a heated walkway for truly maintenance-free winter access (no shoveling, ever!) and an attached two-car garage currently used as a game room, easily adapted back to garage space or reimagined as a workshop, studio, or home office. With commercial zoning, just 10 minutes from Okemo Mountain Resort, and a history as a successful Airbnb, this rare property offers character, flexibility, income potential, and true country charm.

3466 Vt Route 103 N, Chester

$360,000

This wonderful home has so much to offer! This property has many great features including a brand new roof just put on this summer, great large windows allowing nature light into the living space, a very large oversized Two car garage which also has a magnificent workshop with 220 electric already hooked up, wonderful garden areas with flowers and bushes and so much more! The property also features a newly built timber frame sugar style shack perfect for many different uses. There is the possibility for single level living with the downstairs bedroom being right across from the full bathroom as well as the laundry hook up's being on the first floor. In a great location just a few minutes from the quaint town of Chester 13 minutes from Magic Mountain and just 25 minutes from Okemo Mountain where there are shops, restaurants, Skiing and so much more!

3 Beds ⋅ 2 Baths ⋅ 5056140 MLS

This wonderful home has so much to offer! This property has many great features including a brand new roof just put on this summer, great large windows allowing nature light into the living space, a very large oversized Two car garage which also has a magnificent workshop with 220 electric already hooked up, wonderful garden areas with flowers and bushes and so much more! The property also features a newly built timber frame sugar style shack perfect for many different uses. There is the possibility for single level living with the downstairs bedroom being right across from the full bathroom as well as the laundry hook up's being on the first floor. In a great location just a few minutes from the quaint town of Chester 13 minutes from Magic Mountain and just 25 minutes from Okemo Mountain where there are shops, restaurants, Skiing and so much more!

231 Richardson Rd, Chester

$359,000

Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area — a practical entryway for Vermont living. The open kitchen and dining area provide plenty of room for gatherings, while the cozy living room invites relaxation after a long day. A full bathroom completes the main level for easy accessibility. Upstairs, you’ll find three comfortable bedrooms filled with natural light. The attached back barn offers exciting potential for additional living space, a workshop, or studio. Outside, enjoy your private fenced backyard with garden space, a fire pit, and even a bar area — perfect for entertaining family and friends. This inviting village home combines charm, functionality, and opportunity — come experience all that Chester has to offer! Visit the Okemo real estate community today. Taxes are based on current town assessment.

3 Beds ⋅ 1 Baths ⋅ 5070720 MLS

Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area — a practical entryway for Vermont living. The open kitchen and dining area provide plenty of room for gatherings, while the cozy living room invites relaxation after a long day. A full bathroom completes the main level for easy accessibility. Upstairs, you’ll find three comfortable bedrooms filled with natural light. The attached back barn offers exciting potential for additional living space, a workshop, or studio. Outside, enjoy your private fenced backyard with garden space, a fire pit, and even a bar area — perfect for entertaining family and friends. This inviting village home combines charm, functionality, and opportunity — come experience all that Chester has to offer! Visit the Okemo real estate community today. Taxes are based on current town assessment.

531 Main St, Chester

$359,000

Beautifully set in total privacy, this cozy cabin is the perfect retreat! Nestled on a secluded, level lot, this charming home offers a peaceful escape surrounded by nature. Inside, you’ll find wide pine floors, granite countertops, and a freshly painted interior and exterior that give the space an updated feel. The spacious layout includes large rooms and a versatile loft ideal for guests, a small home office, or extra storage. Unwind in the large Jacuzzi jet tub after a long day, or step outside to enjoy the beautifully landscaped grounds. A serene, oversized pond adds to the tranquil setting, while a fenced-in garden area is perfect for growing your own vegetables or flowers. Relax or entertain under the covered stone patio, and enjoy the many thoughtful touches throughout the property that make it truly special. Whether you're looking for a weekend getaway or a full-time home, this private cabin has everything you need and more!

2 Beds ⋅ 1 Baths ⋅ 5061244 MLS

Beautifully set in total privacy, this cozy cabin is the perfect retreat! Nestled on a secluded, level lot, this charming home offers a peaceful escape surrounded by nature. Inside, you’ll find wide pine floors, granite countertops, and a freshly painted interior and exterior that give the space an updated feel. The spacious layout includes large rooms and a versatile loft ideal for guests, a small home office, or extra storage. Unwind in the large Jacuzzi jet tub after a long day, or step outside to enjoy the beautifully landscaped grounds. A serene, oversized pond adds to the tranquil setting, while a fenced-in garden area is perfect for growing your own vegetables or flowers. Relax or entertain under the covered stone patio, and enjoy the many thoughtful touches throughout the property that make it truly special. Whether you're looking for a weekend getaway or a full-time home, this private cabin has everything you need and more!

1470 Flamstead Rd, Chester

$350,000

Tucked away on a quiet dirt road, this spacious sunny south-facing home offers a peaceful retreat with sweeping views of the surrounding countryside. Step onto the expansive front deck and take in the stunning long-range scenery, including a picturesque pond just beyond the property—yours to enjoy without the upkeep. Inside, the home is open and inviting, with plenty of room to relax or entertain. The large finished basement provides valuable living space, ideal for a game room, media area, or accommodating guests. Recent improvements include a brand-new roof and a high-efficiency propane furnace, both installed just last year, offering modern comfort and peace of mind. Ideally located close to Okemo, plus Stratton, and Magic Mountain are just a short hop away; this property offers the perfect balance of privacy and accessibility. With Vast trails, dirt roads to roam on this is a heavenly location. Whether you're seeking a full-time residence or a weekend escape, this home welcomes you to experience the best of Vermont living.

4 Beds ⋅ 4 Baths ⋅ 5044528 MLS

Tucked away on a quiet dirt road, this spacious sunny south-facing home offers a peaceful retreat with sweeping views of the surrounding countryside. Step onto the expansive front deck and take in the stunning long-range scenery, including a picturesque pond just beyond the property—yours to enjoy without the upkeep. Inside, the home is open and inviting, with plenty of room to relax or entertain. The large finished basement provides valuable living space, ideal for a game room, media area, or accommodating guests. Recent improvements include a brand-new roof and a high-efficiency propane furnace, both installed just last year, offering modern comfort and peace of mind. Ideally located close to Okemo, plus Stratton, and Magic Mountain are just a short hop away; this property offers the perfect balance of privacy and accessibility. With Vast trails, dirt roads to roam on this is a heavenly location. Whether you're seeking a full-time residence or a weekend escape, this home welcomes you to experience the best of Vermont living.

491 Farrar Rd, Chester

$340,000

***Open House Wednesday August 12th, from 4pm-5:30pm*** Attention Contractors, flippers, and Investors! Great opportunity to build some sweat equity. Single Family with 4 beds 2 baths and 3,734 sqft. This is a property with a TON of potential. SOLD AS IS! Cash or Hard Money ONLY. Sale is contingent upon the seller completing their purchase; seller currently has the property under contract. Seller and seller’s reps. hold a real estate broker or agent license. Some personal items to remain and become the buyer's responsibility.

4 Beds ⋅ 2 Baths ⋅ 5104013 MLS

***Open House Wednesday August 12th, from 4pm-5:30pm*** Attention Contractors, flippers, and Investors! Great opportunity to build some sweat equity. Single Family with 4 beds 2 baths and 3,734 sqft. This is a property with a TON of potential. SOLD AS IS! Cash or Hard Money ONLY. Sale is contingent upon the seller completing their purchase; seller currently has the property under contract. Seller and seller’s reps. hold a real estate broker or agent license. Some personal items to remain and become the buyer's responsibility.

55 Chester St, Chester

$330,000

This Cozy cabin tucked away along the outskirts of Chester is sure to impress. With a brand new roof, heating system and more this is the perfect turn key retreat. The property features both open lawn and forest to explore, just up the road from snowmobiling and hiking trails this property has the ability to be your home base for all your favorite activities year around. Including close proximity to Okemo for downhill skiing and snowboarding in the winter as well as the Chester village and downtown Springfield being only about a 10 minute drive to the local shops, restaurants and more. In a quiet and serene setting this cozy cabin is well maintained, private and has so much to offer!

2 Beds ⋅ 1 Baths ⋅ 5051283 MLS

This Cozy cabin tucked away along the outskirts of Chester is sure to impress. With a brand new roof, heating system and more this is the perfect turn key retreat. The property features both open lawn and forest to explore, just up the road from snowmobiling and hiking trails this property has the ability to be your home base for all your favorite activities year around. Including close proximity to Okemo for downhill skiing and snowboarding in the winter as well as the Chester village and downtown Springfield being only about a 10 minute drive to the local shops, restaurants and more. In a quiet and serene setting this cozy cabin is well maintained, private and has so much to offer!

302 Davidson Hill Rd, Chester

$320,000

They say location is key for a property, if that is true this home knocks it out of the park. Located on a quiet country road less than 3 miles to Chester and 6 miles to Springfield sits this well-maintained ranch home on 2.6 mostly open acres. The open and slightly sloping yard has of established landscaping offering lots of opportunity for gardening, recreation and just good old-fashioned relaxing. Roomy screened porch allows you to enjoy outside all summer without worrying about bugs or rain. Oversized 2 car garage, while not attached does have a covered walkway to the house providing coverage from the elements. The roomy eat-in kitchen has stainless appliances and updated countertops. The light filled living room has views of neighboring pasture as well as open yard. 3 bedrooms and full bath round out the main living area. Hardwood floors give a warm and cozy vibe. Walk out basement has a nicely finished family room with wood stove overlooking the back yard. Laundry room, 1/2 bath and a bonus room finish off this very clean and dry basement. Outbuildings include a pool house for storing all the pool supplies for the above ground pool and you might be able to find a place for a hen or two. Well-maintained, manageable in size make this the perfect home for most anyone. Please call for a showing today!

3 Beds ⋅ 2 Baths ⋅ 5063236 MLS

They say location is key for a property, if that is true this home knocks it out of the park. Located on a quiet country road less than 3 miles to Chester and 6 miles to Springfield sits this well-maintained ranch home on 2.6 mostly open acres. The open and slightly sloping yard has of established landscaping offering lots of opportunity for gardening, recreation and just good old-fashioned relaxing. Roomy screened porch allows you to enjoy outside all summer without worrying about bugs or rain. Oversized 2 car garage, while not attached does have a covered walkway to the house providing coverage from the elements. The roomy eat-in kitchen has stainless appliances and updated countertops. The light filled living room has views of neighboring pasture as well as open yard. 3 bedrooms and full bath round out the main living area. Hardwood floors give a warm and cozy vibe. Walk out basement has a nicely finished family room with wood stove overlooking the back yard. Laundry room, 1/2 bath and a bonus room finish off this very clean and dry basement. Outbuildings include a pool house for storing all the pool supplies for the above ground pool and you might be able to find a place for a hen or two. Well-maintained, manageable in size make this the perfect home for most anyone. Please call for a showing today!

870 Cummings Rd, Chester

$315,000

A big price improvement! The possibilities are endless with this beautiful property that has been in the same family since 1964! You will not find a nicer piece of Vermont land than this, with approx. 34 acres of open pastureland bordered by hundreds of feet of the Williams River. This stream offers some great summertime activities such as swimming and fishing! The house and attached barns can be a showplace with some love, and this property is looking for that person who can bring it back to its former glory days. As they say, the buildings have good bones, so consider this a blank canvas to do whatever you please for renovations. Since it's very original, you can update without having to tear out former "improvements" that might have taken away the antique charm. Since it was a working farm at one time, it still has the old silo. Years ago, this was made into a 4-level living unit. You can bring this back to life and use it as a very unique vacation rental or keep it as a very cool place for your kids and grandkids - much cooler than a treehouse! The attached barns are huge and for years they were used as an antique store. You could do that again, or you could use it for animals. With the open land which supplies a big supply of hay each year, this property would be great for horses, cows, and other large animals. There is also a sugar house, plus a separate building out front that was also used for the antique business. Several apple trees, a huge rhubarb patch, and more!

6 Beds ⋅ 1 Baths ⋅ 5047187 MLS

A big price improvement! The possibilities are endless with this beautiful property that has been in the same family since 1964! You will not find a nicer piece of Vermont land than this, with approx. 34 acres of open pastureland bordered by hundreds of feet of the Williams River. This stream offers some great summertime activities such as swimming and fishing! The house and attached barns can be a showplace with some love, and this property is looking for that person who can bring it back to its former glory days. As they say, the buildings have good bones, so consider this a blank canvas to do whatever you please for renovations. Since it's very original, you can update without having to tear out former "improvements" that might have taken away the antique charm. Since it was a working farm at one time, it still has the old silo. Years ago, this was made into a 4-level living unit. You can bring this back to life and use it as a very unique vacation rental or keep it as a very cool place for your kids and grandkids - much cooler than a treehouse! The attached barns are huge and for years they were used as an antique store. You could do that again, or you could use it for animals. With the open land which supplies a big supply of hay each year, this property would be great for horses, cows, and other large animals. There is also a sugar house, plus a separate building out front that was also used for the antique business. Several apple trees, a huge rhubarb patch, and more!

525 Rte 103 N, Chester

$310,000

Attention investors, contractors, and buyers seeking a renovation project with upside. Located in the desirable town of Chester, this property presents a rare opportunity to create value through a full rehabilitation. Set on a well-situated lot with convenient access to Route 102 and nearby commuter routes, the home offers a solid footprint and endless potential for the right buyer with vision and ambition. The existing structure is in need of significant repairs and updates and is being sold strictly as-is. This is an ideal canvas for those looking to redesign, rebuild, or modernize to today’s standards. Whether your goal is a resale, rental, or custom home, the property provides a chance to transform an underutilized asset into something special. In addition to the main residence, the property includes a barn and a greenhouse, adding to its versatility and potential. These additional structures offer opportunities for storage, workshop space, hobby farming, or future restoration, subject to condition and buyer due diligence. Chester is known for its rural charm and easy access to Derry, Manchester, and the Seacoast, making this location attractive for future homeowners or tenants alike. Bring your contractor, tools, and imagination. Cash or rehab financing likely required. Buyer to perform all due diligence. A great opportunity for those ready to take on a project and unlock the full potential of this Chester property.

2 Beds ⋅ 1 Baths ⋅ 5073880 MLS

Attention investors, contractors, and buyers seeking a renovation project with upside. Located in the desirable town of Chester, this property presents a rare opportunity to create value through a full rehabilitation. Set on a well-situated lot with convenient access to Route 102 and nearby commuter routes, the home offers a solid footprint and endless potential for the right buyer with vision and ambition. The existing structure is in need of significant repairs and updates and is being sold strictly as-is. This is an ideal canvas for those looking to redesign, rebuild, or modernize to today’s standards. Whether your goal is a resale, rental, or custom home, the property provides a chance to transform an underutilized asset into something special. In addition to the main residence, the property includes a barn and a greenhouse, adding to its versatility and potential. These additional structures offer opportunities for storage, workshop space, hobby farming, or future restoration, subject to condition and buyer due diligence. Chester is known for its rural charm and easy access to Derry, Manchester, and the Seacoast, making this location attractive for future homeowners or tenants alike. Bring your contractor, tools, and imagination. Cash or rehab financing likely required. Buyer to perform all due diligence. A great opportunity for those ready to take on a project and unlock the full potential of this Chester property.

211 Sandown Rd, Chester

$289,000

Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided from the parcel across the street and they may be purchased together. See MLS #5069927 This is a nice level to rolling lot with some open and some woods, has a 2 car garage, 2 enclosed porches and is well put together inside. The outside needs some finish work, so not likely to go a federal program. With some TLC this will be a fab get away. The town maintains the road to the house...such a benefit! This is a must see for location

2 Beds ⋅ 3 Baths ⋅ 5069928 MLS

Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided from the parcel across the street and they may be purchased together. See MLS #5069927 This is a nice level to rolling lot with some open and some woods, has a 2 car garage, 2 enclosed porches and is well put together inside. The outside needs some finish work, so not likely to go a federal program. With some TLC this will be a fab get away. The town maintains the road to the house...such a benefit! This is a must see for location

106 Contro Rd, Chester

$275,000

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

$269,000

This cozy gambrel style home tucked away on a nice level 1/2-acre lot just on the outskirts of Chester village offers lots of yard space, lots of storage space and is an easy keeper. This cute home offers hardwood floors on the first floor, has lots of natural light, an enclosed porch that could work as a home office, dining area, mud room or just a place to hang out. 2nd floor features three bedrooms with the primary leading out to a deck overlooking the yard. Nice high ceilings on the second floor make the rooms very open and bright. There's an attached storage room allowing room for freezers, storage or a second mud/entry room. Large 2 bay garage with second floor storage, a side shed that would be perfect for a garden shed and a separate space for lawn and snow blowers. The owners have done lots of upgrades, including a full house generator. So, if you are looking, be sure to add this home to your list.

3 Beds ⋅ 1 Baths ⋅ 5082324 MLS

This cozy gambrel style home tucked away on a nice level 1/2-acre lot just on the outskirts of Chester village offers lots of yard space, lots of storage space and is an easy keeper. This cute home offers hardwood floors on the first floor, has lots of natural light, an enclosed porch that could work as a home office, dining area, mud room or just a place to hang out. 2nd floor features three bedrooms with the primary leading out to a deck overlooking the yard. Nice high ceilings on the second floor make the rooms very open and bright. There's an attached storage room allowing room for freezers, storage or a second mud/entry room. Large 2 bay garage with second floor storage, a side shed that would be perfect for a garden shed and a separate space for lawn and snow blowers. The owners have done lots of upgrades, including a full house generator. So, if you are looking, be sure to add this home to your list.

45 Dalrymple St, Chester

$261,500

Located on the Chester, N. Springfield town line, this cute house sited on just under 3 acres is move in ready. It offers It offers 3 bedrooms two full baths and a designated laundry room. The renovated kitchen featuring stone countertops and nicely styled cabinets. In addition, there is beautiful post and beam back porch that is perfect for morning coffee and late afternoon quiet. With a small amount of work the porch can easily be converted to be comfortably used 3 seasons. Sited away from the road, is a lovely, secluded pond perfect for a quick swim or if interested stocking with native trout. The side lawn features an established orchard with peach, plum pear and apple trees. There is also a garden area that needs some love and attention has established berry bushes. This is a perfect starter home, or the perfect single level living situation. This lovely home is located a 30-minute drive to Okemo Mt and close proximity to other local ski areas as well as the lake region of Southern Vermont. In addition, it is convenient to the Upper Valley for shopping and a state-of-the-art medical facility. THIS IS AN "AS IS" LISTING.

3 Beds ⋅ 2 Baths ⋅ 5073287 MLS

Located on the Chester, N. Springfield town line, this cute house sited on just under 3 acres is move in ready. It offers It offers 3 bedrooms two full baths and a designated laundry room. The renovated kitchen featuring stone countertops and nicely styled cabinets. In addition, there is beautiful post and beam back porch that is perfect for morning coffee and late afternoon quiet. With a small amount of work the porch can easily be converted to be comfortably used 3 seasons. Sited away from the road, is a lovely, secluded pond perfect for a quick swim or if interested stocking with native trout. The side lawn features an established orchard with peach, plum pear and apple trees. There is also a garden area that needs some love and attention has established berry bushes. This is a perfect starter home, or the perfect single level living situation. This lovely home is located a 30-minute drive to Okemo Mt and close proximity to other local ski areas as well as the lake region of Southern Vermont. In addition, it is convenient to the Upper Valley for shopping and a state-of-the-art medical facility. THIS IS AN "AS IS" LISTING.

818 Davidson Hill Rd, Chester

$260,000

Antique charm at its best! This vintage beauty dates back to the horse and buggy days, but you'd hardly know it once you step inside. Beautifully done hardware floors, newer windows, custom built hardwood cabinets in the kitchen with loads of storage, modern appliances, and lots of natural light gives you that warm and relaxing feeling. Large first floor living room, dining room and bedroom add to the convenience. The second floor has two more generously sized bedrooms. Additionally, there is an incredible amount of storage in the barn. All this, within walking distance to shopping, restaurants, town hall, and all of the basics you might need in the quintessential town of Chester, Vermont! This house is anxiously awaiting it's next lucky owner.

3 Beds ⋅ 2 Baths ⋅ 5104543 MLS

Antique charm at its best! This vintage beauty dates back to the horse and buggy days, but you'd hardly know it once you step inside. Beautifully done hardware floors, newer windows, custom built hardwood cabinets in the kitchen with loads of storage, modern appliances, and lots of natural light gives you that warm and relaxing feeling. Large first floor living room, dining room and bedroom add to the convenience. The second floor has two more generously sized bedrooms. Additionally, there is an incredible amount of storage in the barn. All this, within walking distance to shopping, restaurants, town hall, and all of the basics you might need in the quintessential town of Chester, Vermont! This house is anxiously awaiting it's next lucky owner.

447 Elm St, Chester

$250,000

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

3 Beds ⋅ 2 Baths ⋅ 5088678 MLS

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

202 Mountain Vw, Chester

$240,000

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

$239,000

Not your cookie cutter home, this charming 2 BR home is located on the outskirts of Chester. One floor living for those wanting an easy keeper and carefree living. Hardwood floors throughout, large living room, formal dining room, galley kitchen and 2 roomy bedrooms. And let's not forget the spacious breezeway/entry. This area is perfect for hosting a gathering of friends and neighbors under shade or away from summer rains. Current owners have spent three years developing extensive perennial beds ensuring that there is always a flower in bloom. Along with perennials, owners have added lots of specialty trees-hardwood and fruit trees and bushes along with raised and in-ground beds and a new garden shed to store your tools. All this and there is still lawn to play on.

2 Beds ⋅ 1 Baths ⋅ 5086079 MLS

Not your cookie cutter home, this charming 2 BR home is located on the outskirts of Chester. One floor living for those wanting an easy keeper and carefree living. Hardwood floors throughout, large living room, formal dining room, galley kitchen and 2 roomy bedrooms. And let's not forget the spacious breezeway/entry. This area is perfect for hosting a gathering of friends and neighbors under shade or away from summer rains. Current owners have spent three years developing extensive perennial beds ensuring that there is always a flower in bloom. Along with perennials, owners have added lots of specialty trees-hardwood and fruit trees and bushes along with raised and in-ground beds and a new garden shed to store your tools. All this and there is still lawn to play on.

15 Breezy Ln, Chester

$230,000

The view from the road does not give you the fact that behind the house is a beautiful and private backyard! This property has great possibilities for you to create your own vision of what it can become. You could either do some improvements to the existing gambrel structure which has been a comfortable residence for many years, or you could use it as some kind of allowed business or rental and turn the really nice barn into your new house. The barn sits in a really nice spot overlooking the open landscaped property, with a nice private woodsy area behind. Offered for sale for the first time in almost 40 years!

1 Beds ⋅ 1 Baths ⋅ 5058302 MLS

The view from the road does not give you the fact that behind the house is a beautiful and private backyard! This property has great possibilities for you to create your own vision of what it can become. You could either do some improvements to the existing gambrel structure which has been a comfortable residence for many years, or you could use it as some kind of allowed business or rental and turn the really nice barn into your new house. The barn sits in a really nice spot overlooking the open landscaped property, with a nice private woodsy area behind. Offered for sale for the first time in almost 40 years!

2739 Rte 11, Chester

$227,000

Much more here than meets the eye. This home had heating efficiency completed with SEVCA, new siding, new hot water heater, chimney and furnace inspected and some new exterior paint. Nice level yard, attached two car garage PLUS detached barn! Close to downtown Chester and 15 minutes to Ludlow and Okemo/Vail resort. There is a large 3-season porch, two spacious bedrooms and large country kitchen. This little gem is just waiting for a little polish and it will make a wonderful home. Easy to view, improvements are listed in documents.

2 Beds ⋅ 1 Baths ⋅ 5070689 MLS

Much more here than meets the eye. This home had heating efficiency completed with SEVCA, new siding, new hot water heater, chimney and furnace inspected and some new exterior paint. Nice level yard, attached two car garage PLUS detached barn! Close to downtown Chester and 15 minutes to Ludlow and Okemo/Vail resort. There is a large 3-season porch, two spacious bedrooms and large country kitchen. This little gem is just waiting for a little polish and it will make a wonderful home. Easy to view, improvements are listed in documents.

1374 Vt Route 103 N, Chester

$220,000

Adorable Village Home in the Heart of Chester, Vermont This charming 3-bedroom, 1-bath home is packed with personality and Vermont village charm! Set on a sunny quarter-acre lot, this sweet property features an oversized deck perfect for summer barbecues, a great yard for play or gardening, and a convenient attached garage. Inside, you’ll love the warm, inviting living space with wood accents, an open-concept kitchen and dining area, and cozy bedrooms filled with natural light. The updated bath has a fresh, modern feel, and the flexible layout offers space for guests, work-from-home, or hobbies. This is more than a house — it’s a home with heart, waiting for its next chapter. Located just minutes from Chester’s historic village green — shops, dining, and year-round recreation are all close by. Whether you’re looking for a starter home, Vermont getaway, or a low-maintenance lifestyle, this adorable home checks all the boxes.

3 Beds ⋅ 1 Baths ⋅ 5052054 MLS

Adorable Village Home in the Heart of Chester, Vermont This charming 3-bedroom, 1-bath home is packed with personality and Vermont village charm! Set on a sunny quarter-acre lot, this sweet property features an oversized deck perfect for summer barbecues, a great yard for play or gardening, and a convenient attached garage. Inside, you’ll love the warm, inviting living space with wood accents, an open-concept kitchen and dining area, and cozy bedrooms filled with natural light. The updated bath has a fresh, modern feel, and the flexible layout offers space for guests, work-from-home, or hobbies. This is more than a house — it’s a home with heart, waiting for its next chapter. Located just minutes from Chester’s historic village green — shops, dining, and year-round recreation are all close by. Whether you’re looking for a starter home, Vermont getaway, or a low-maintenance lifestyle, this adorable home checks all the boxes.

442 103 S, Chester