Chester, VT Homes for Sale with Garage

Beautifully maintained 2005 Contemporary Cape nestled on 6.7 private acres with sweeping long-range Vermont views. Owned and cherished by just one family, this move-in-ready home offers the best of country living with modern updates. The completely renovated kitchen boasts a Wolf range, Sub-Zero refrigerator, Bosch dishwasher, and quartz countertops, seamlessly flowing into the dining

Gary Coger Four Seasons Sotheby's Int'l Realty

Welcome to your own private retreat—98 acres of serene Vermont beauty featuring meadows, woods, two ponds, and eight versatile outbuildings. Thoughtfully maintained and tastefully appointed, this charming home is nestled in a park-like setting complete with long, historic rock walls, mature trees, and flourishing perennial gardens. Nature lovers will revel in the abundance of wildlife, from

Jessica Landers Barrett and Valley Associates Inc.

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

Joseph Karl William Raveis Real Estate Vermont Properties

Charming Renovated Farmhouse in the Heart of ChesterThis beautifully renovated farmhouse sits on a level half-acre lot just steps from Chester’s Village Green, shops, and local amenities. Offering the perfect blend of historic charm and modern updates, this 4-bedroom, 3-bath home is ideal for year-round living or a Vermont getaway.Inside, enjoy a spacious kitchen with custom

McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

Step back in time and experience the timeless charm of this beautifully preserved historic farm, originally known as Thompson Farm and later operated as Jersey Girl Farm. Dating back to 1830, this remarkable property blends 19th-century character with modern sustainability and comfort. The main house retains its original doors and slate roof, while recent upgrades include a new heating system,

Joe Castaluccio Winhall Real Estate

With only 50 stone homes in all of Vermont, this one stands out as possibly the most beautiful; uniquely situated on 20 acres of gorgeous greenlawn, fields, forest, rolling hills, extensive stone walls. A mere 2 miles to Chester. Since 2020 the house has been transformed & restored w/improvements such as interior & exterior paint, new windows & French Doors, stone steps & walkways, 50 panel

Gary Coger Four Seasons Sotheby's Int'l Realty

Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living space—perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside,

Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

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,

Erin Kendall EXP Realty

Welcome to your dream home – This meticulously maintained New England-style gem is bursting with charm and modern convenience. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by the beautiful hardwood floors that add warmth and character to every room.Bask in the great natural light that fills

Lisa Kelley Cummings & Co

Open House Saturday 10/4 and Sunday 10/5 12 to 2 - Welcome to your Vermont retreat, an inviting one bedroom, one bath home sat on 2.5 acres at the end of a dead end road in Chester. This 528 square-foot cottage has been thoughtfully updated for four season, comfort, featuring full insulation, a woodstove for cozy evenings, and efficient mini-splits providing both heating and air-conditioning.

Sandy Reavill Real Broker LLC

If you know where Baltimore, VT is, you know it is a hidden gem and one of the smallest towns in VT with a population of about 250 people yet less than 10 minutes from all conveniences including shopping and dining. Love the outdoors and wildlife; this is the spot for you given Baltimore backs up to Hawks Mountain Wildlife Reserve with over 2000 acres teaming with deer and other furry and

Leila Tarantelli KW Coastal and Lakes & Mountains Realty/Hanover

Everything you’ve been looking for in a Vermont home—completely renovated with care and character. Nearly every aspect of this Chester property is new: electrical, plumbing, heating, insulation, drywall, windows, and more—offering the low-maintenance peace of mind homeowners crave. The kitchen features a stylish farmhouse sink and stone countertops, while the upstairs bathroom includes a

Betsy Adamovich Real Broker LLC

Skygate Farm is a historic Vermont farmstead first settled in the 1800s, which today spans over 300 acres of meadows, forests, trails, and weathered stone walls. The setting speaks of an early farmer’s wisdom — sited along a gentle hill to shield against the northwest winds, while opening to the first light of day and the vast mountain views to the east. Found at the end of a winding gravel road,

Dia Jenks LandVest, Inc/Woodstock

Price Reduction! Come see this private 2-acre lot, off a side street close to the picturesque Chester village. This well maintained 1968 mobile home has a bright open concept addition. Close to ski mountains and other snowmobile trails. Make this a Vermont getaway or a permanent home joining a wonderful community.

Amy Carson Lowe's Real Estate, LLC

Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

Joshua Lemieux Remax Summit

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

Glenn Olney Barrett and Valley Associates Inc.

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

Daire Gibney Barrett and Valley Associates Inc.

Welcome to your brand-new, 2,400 sq ft dream home! This modern, open-concept residence shines with high ceilings and abundant natural light. The gourmet kitchen is a showstopper, boasting custom cabinetry, stone countertops, a large island, and state-of-the-art appliances.The luxurious primary suite features a double vanity, custom shower, and walk-in closet. Upstairs, find three spacious

Robin Apps Four Seasons Sotheby's Int'l Realty