42 properties for sale in Baileys Mills, Chester town Windsor County Vermont

Perfect location, nice neighborhood, near the hospital, downtown and minutes to the interstate! Featuring a first floor bed and 3/4 bath, it is perfect for aging in place. Eat in kitchen/dining convenient for those who love to cook. And, the living room is huge. Sporting a front porch, a bit of a yard and extra parking in the back, there is plenty of room for gatherings. This home still has some items to finish, so bring the tool belt. Sellers are actively searching for housing and must find suitable housing before closing

MOTIVATED SELLERS just adjusted the price significantly! Sweet property with 7.5 acres, great pond, quiet setting and private. This could be your escape to your own peaceful, homestead. Set on 7.5 acres of wooded and open land this property is truly a respite from the stresses of the world. This multi-level 3-bedroom, 3 bath home offers convenience and options. The spacious living room with hardwood floors leads to a large eat-in kitchen with ample storage and room for an island if desired. Step into the Family room or a large dining room with access to one of the decks overlooking the pond. The primary bedroom on the third level has a convenient 3/4 bathroom as well as a deck to again enjoy the views of wildlife and the pond. An additional second floor bedroom also enjoys a deck to enjoy the view and wildlife. A full bathroom is convenient on level 3. On the lower level a large family/game room awaits with a wood stove to keep you warm on those chilly nights and offers full access to

First time offered in over 60 years, this well cared for 3 bedroom, 2 bath home is a rare opportunity to own a property that has been truly loved and maintained. Set on a spacious, level lot in an area of well kept homes, the property immediately stands out with its large lawn, ideal for outdoor enjoyment, gardening, or simply relaxing. Inside, you'll find over 1,500 square feet of comfortable living space with a layout that feels practical and inviting. Every corner reflects years of thoughtful upkeep and pride of ownership. The enclosed porch offers a perfect sitting area to enjoy your morning coffee or unwind at the end of the day, adding a cozy extension to the home's living space. A two car garage provides plenty of room for vehicles, storage, or hobbies, while a utility shed at the back of the property offers even more flexibility for tools and equipment. Located just minutes from local skiing, snowmobile trails, and hiking, this home is well positioned for those who enjoy Vermon

Perched on a hill in one of Springfield's most desirable neighborhoods, this well-maintained home offers a peaceful setting just minutes from downtown amenities. Tucked away from the hustle and bustle, 6 Juniper Hill Road has been lovingly cared for over the years and is ready for its next chapter. The flexible layout offers four bedrooms and two bathrooms, making it ideal for a variety of living arrangements. The lower level features a bedroom, a 3/4 bath, laundry area, and direct access to the attached two-bay garage, creating an excellent setup for guests, extended family, or anyone seeking first-floor living options. Upstairs, you'll find three additional bedrooms, a full bath, along with comfortable living, dining, and kitchen spaces that flow nicely together. The recently renovated kitchen is a standout, featuring beautiful stone countertops and a fresh, updated feel that's ready for everything from busy weekday meals to holiday gatherings. The upstairs bathroom renovation has al

MOTIVATED SELLER! Nestled in the rolling countryside of Springfield, this 1810 Federal-style brick farmhouse stands proudly on 44 breathtaking acres-an offering rich in history, character, and Vermont lifestyle. Open fields stretch out from the home, ideal for gardens, small-scale farming, or simply soaking in the pastoral beauty. Wooded acreage invites exploration, wildlife watching, and the opportunity to tap your own maple trees. Seavers Brook meanders gently through the property, creating a peaceful water feature. A picturesque spring fed pond with a dock adds yet another layer of tranquility. An old town highway crosses the land and is now used as a snowmobile trail, providing direct access to Vermont's renowned VAST trail system-an exceptional recreational amenity right from your doorstep. The main residence is soaked in historic charm. High ceilings, beautifully maintained wood floors, and exposed barn beams speak to its early 19th-century heritage. Deep-set windowsills and orig

Nestled on a beautiful corner lot on a dead-end road surrounded by mature trees, this well-maintained 3-bedroom, 2-bath home offers comfort, space, and privacy on a generous 0.25-acre lot. Step inside to a bright and inviting living area filled with natural light, creating the perfect space to relax or entertain. Attractive tile flooring flows throughout the main level, complementing the home's warm and welcoming feel. The modern kitchen opens seamlessly to the dining area and living room, providing an ideal layout for everyday living and gatherings. All three bedrooms are conveniently located on the main level, including a spacious primary suite featuring a private bath with dual sinks, a soaking tub, and a separate shower. The finished lower level expands your living space with beautiful laminate floors, a cozy pellet stove, and endless possibilities for a family room, recreation area, home office, or gym. Outside, enjoy your own private retreat with a huge deck overlooking the backy

Unique opportunity to own a spacious three-bedroom townhouse at The Castle, one of the area's most sought-after luxury resort communities. Offering exceptional quality and amenities unlike any other in the region, residents enjoy year-round access to an Aveda spa, heated outdoor saltwater pool, tennis courts, a fully equipped fitness center with sauna and locker rooms, and an outdoor hot tub. Designed with timeless architecture and thoughtfully planned floor plans, this beautifully maintained townhouse offers both comfort and privacy. The residence features three bedrooms, including an oversized primary suite, a generous loft, a versatile den, and 3 1/2 bathrooms, providing ample space for family and guests. This desirable ground-level end residence offers two levels of living with no neighbors above or below, ensuring exceptional privacy and quiet enjoyment. The easy, step-free entry provides convenient access for owners and visitors alike. Ideally located just four miles from Okemo M

Historic Vermont Hill Farm on 112 Acres Discover the timeless beauty of Vermont country living on this historic hill farm, offering 112 acres of rolling landscapes, open pasture, and wooded privacy. Set among the peaceful hills, this classic property combines the character of a traditional Vermont homestead with the space, versatility, and natural beauty that make rural living so special. The charming 1793 post and beam Cape-style home features 3 bedrooms and 3 baths, blending historic appeal with comfortable everyday living. Warm, inviting spaces provide room to gather, relax, and enjoy the views of the surrounding countryside. Exposed beams and farmhouse character create a welcoming atmosphere while offering the conveniences of modern living. The property includes approximately 20 acres of open rolling pasture, ideal for animals, farming, recreation, or simply enjoying sweeping views across the Vermont landscape. The remaining acreage is a mix of forest and natural woodland, offering

If you're looking for the ultime village ski house look no more! This four bedroom three and a half bath TURN KEY home is nestled in the village of Proctorsville. Home to Singletons Store, Outer Limits Brewery, Murdoch's On The Green and much more walking distance away. Step into this lovely well appointed home and you'll feel right at home. The kitchen boasts granite counters with a large breakfast bar. Oak cabinetry, mostly stainless steel appliances, tile backsplash and under counter lighting. You'll love the open concept of the kitchen and dining room, with a granite two sided fireplace. Mozie on into the large living room with space for the whole crew and cozy up to the other side of the fireplace. The first floor is completed with an en-suite bedroom with a beautiful view of Hawks Mountain, the bathroom is finished with a tiled shower and a natural wood vanity. Rounding off the main floor with a half bath laundry room combo and a convenient corner nook for gear storage. Upstairs

This property must be seen in person to be appreciated. Very clean and move-in ready Vermont 3-bedroom, 2-bath home just minutes from Okemo Mountain Resort in Proctorsville Village. Ideal as a low-maintenance vacation retreat or full-time residence, this well-kept home on.26+/- acres features a new roof and combines comfort and convenience in one of the most desirable areas of the Okemo Valley. Enjoy a spacious living room and bright eat-in kitchen with breakfast nook, and a wonderful enclosed breezeway, which is the perfect spot to relax or entertain in 3 seasons. The living room offers generous space with picture windows creating plenty of light. The second floor spacious, primary bedroom is equipped with many outlets for charging devices. Two additional bedrooms and a 3/4 bath complete the second floor. House re-built in 70's. The two-car attached garage provides workshop and storage space off the paved driveway. A very neat, clean and dry basement with up newer oil tank, Thermoprid

Welcome to your new home and business headquarters in Cavendish, Vermont. This expansive property near Okemo Mountain Resort blends residential comfort and commercial opportunity. Imagine a chef's dream kitchen with double ovens, refrigerators, and cooktops, perfect for culinary creativity. The home features three large bedrooms, spacious living areas, and a large deck for relaxation and entertaining. It's also the base of a thriving business, offering a turnkey opportunity for entrepreneurs. With 2,000 square feet of unfinished space, your imagination can run wild, perfect for business expansion, a restaurant, ski club, or additional living space. Recent renovations ensure the property is in pristine condition, ready for you to move in. Conveniently located just minutes from Okemo Mountain, this property attracts both local and tourist traffic. Town water and sewer services add to the convenience, making it ideal for residential and commercial use. Whether expanding your home or start

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

This well built log home packs quite the punch. The open concept first floor spills out onto the generous front deck, essentially doubling the first floor area to roam. Two nearly identical craftsman quality wooden clad bedrooms make up the second floor. The home has a new roof, new on-demand hot water system, fresh stain on the log exterior, updated electrical, and brand new LVL carrying beam and floor joists in the basement. Many other practical upgrades and extensive landscaping has been made and this home is in mint condition. The sellers recently did a drinking water test, had the septic pumped, and did a home inspection, leaving no stone unturned. The 11 acre parcel transitions from a large sunny open yard to old stone walls and hardwood forest and rises nearly to the humble summit of Davidson Hill (1053' elevation). The owners let a neighboring property tap most of the maple trees in exchange for maple syrup. The house is located just feet from Trail #5 of the Hawks Mountain Rid

This well-maintained property in Chester is in close proximity to many of Vermont's best ski mountains. It is not likely that you would drive by this property without it catching your eye. From the meticulous grounds with beautiful trees to the Vermont native stone wall lining the road, to the established perennial beds to the paved driveway leading back to this pleasing home with an attached garage. This light-filled home with two floors of living (plus a multi-room lower-level walkout ready to finish) has great open space on the main level. The kitchen with updated granite counters is open to the dining area which has a sliding door to the large back deck. This is the perfect space to have dinner overlooking the landscaped back yard. Try your green thumb in the vegetable garden that is ready for planting. The living room is also connected to the dining area making this space perfect for friends and family to gather. A convenient bedroom and bathroom complete this level. Upstairs are

Tucked away on a quiet country road in one of Chester's most coveted areas, this striking contemporary home offers the ultimate Vermont lifestyle, just miles from the Okemo Mountain base lodge. Embraced by nature and thoughtful landscape, the property seamlessly connects refined indoor living with the natural beauty of its private riverfront, complete with your own summer swimming hole. Inside, the main level centers around a commanding, floor-to-ceiling fieldstone wood-burning fireplace, beautifully complemented by rich hardwood floors and a bespoke custom kitchen. Designed for privacy, the primary suite features a spa-like ensuite bath, while two additional guest bedrooms and a 3/4 bath provide plenty of space for family or weekend visitors. Intelligently designed for flexible living, the upper-level loft serves as an inspiring home office or studio, while the bright, walk-out lower level offers incredible potential for a game room, home gym, or ski lounge. Transition effortlessly ou

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

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 o

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 p

An in-town home with 7 acres! Imagine the fun you could have with all of this open land. Three-bedroom two bath ranch home with outdoor space to garden, farm, explore and more. Home has fresh interior paint, new carpets, extra tall basement with a deep bay for campers, boats, toys or workshop. The kitchen island is a cook's dream with plenty of space to cook and easy layout for lots of people in the kitchen. Open concept kitchen-dining-living room and sunroom make this home great for entertaining or just relaxed living. Primary bedroom is generous in size and has attached 3/4 bath. Property has an older outbuilding that needs work but sturdy. Seller will remove at buyer's request

COUNTRY LIVING ON 4.97 ACRES, JUST 6 MILES TO SPRINGFIELD SHOPPING PLAZA. 9 ROOM HOME OFFERS GROUND FLOOR WITH APPLIANCED KITCHEN W/ DINING AREA, LIVING ROOM, SUNROOM, FULL BATH, FRONT BEDROOM, and ANOTHER BEDROOM W/ FULL BATH. THE SECOND FLOOR HAS 2 BEDROOMS PLUS ANOTHER BEDROOM W/ 3/4 BATH AND WALK-IN CLOSET. SEVCA RECENTLY INSULATED ENTIRE HOUSE AND ADDED A NEW FHA OIL FURNACE IN THE SUMMER OF 2025. RETIRED OWNER WANTS TO DOWNSIZE. NEED 24-HOUR NOTICE TO SHOW

Welcome to 147 Park Street! Situated on a 0.31-acre lot with a fully fenced yard, perennial flower gardens, and attractive landscaping, this home offers plenty of space both inside and out. Full of character and style, this spacious home features a thoughtful floor plan designed for everyday living. The large kitchen includes updated appliances, a generous dining area, and plenty of room for meal preparation and gathering. Just off the kitchen, you'll find a walk-in pantry, office, closet, access to the attached barn and basement, and a bonus room currently being used as a bedroom. The unfinished basement provides excellent space for a workshop, hobbies, storage, or future projects. The main level also includes a half bath, formal dining room, and an expansive living room with plenty of space for entertaining family and friends. Upstairs, the primary suite offers a private retreat with its own bathroom. This level also includes a full bath, convenient laundry area, and two additional b

Lovely raised ranch located in a sought-after neighborhood, offering 3 bedrooms and 2 baths with an open-concept living area perfect for everyday living and entertaining. Enjoy the warmth and charm of two fireplaces one on the main level and another in the lower-level family room, providing cozy spaces year-round. This home offers great potential and will benefit from some TLC, making it an excellent opportunity to build equity. Whether you're searching for a second home close to skiing or a comfortable full-time residence, this property checks all the boxes. Best suited for cash or rehab loan

Perched on South Hill with sweeping views of the surrounding Vermont landscape, this authentic timber frame home offers the quintessential Green Mountain lifestyle on 10+/- private acres. Soaring exposed post-and-beam construction, tongue-and-groove cathedral ceilings, and rich hardwood floors flow throughout, giving the home a warmth and character that simply can't be replicated. The open main level is anchored by a stone hearth and wood stove - the heart of the home on a crisp Vermont evening. The living and dining areas open seamlessly beneath an impressive timber truss system, while the kitchen features stainless steel appliances and dark stone countertops. A first-floor bath adds convenience. Upstairs, the timber frame continues to impress with vaulted bedroom spaces, loft potential, and views that remind you why you came to Vermont in the first place. The unfinished basement offers a blank canvas - workshop, additional living space, or storage. Outside, a classic red barn with tw

A true farm ready for its next chapter! These grounds have been lovingly tilled, gardened, sown, and harvested; the soil meticulously fed, and the pastures grazed by generations of animals. Hundreds of pounds of produce have been grown in and out of the greenhouse high tunnel. A massive, fixed-rack solar array covers the primary costs of electricity and feeds back into the grid. What is most important on a farm? A beautiful kitchen to serve as the heart of the home. This space features a nearly 10-foot-long granite island with counter-height seating, TWO full-size sinks, a 6-burner-plus-griddle propane stove with a professional hood vent, a French-door refrigerator, and a walk-in pantry. It's the perfect setup for canning, preserving, or simply gathering to enjoy fresh peaches harvested right from your land. The main floor also offers a laundry room, a beautifully renovated 3/4 bath, and a flexible office/bedroom space. Upstairs, you'll find three additional bedrooms, another nicely re

A classic Vermont farmhouse with space, flexibility, and possibilities for the future. Currently enjoyed as a spacious single-family home, the layout offers clear potential to adapt for multi-generational living or a two-family configuration with modification. For those with a bigger vision, the substantial rear barn and workshop areas may offer further possibilities, subject to permitting and approvals. Inside, generous rooms and abundant natural light create a warm, comfortable feel throughout. The main level features inviting living and dining spaces and an updated eat-in kitchen. The home has benefited from numerous improvements, including a new roof, new wood and pellet stoves within the past two years, a whole-house dehumidifier, and a long list of cosmetic updates that have refreshed the property while preserving its traditional farmhouse character. Upstairs, additional living space provides flexibility for bedrooms, office space, guest quarters, or a more independent living arr