Chester VT
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Under Contract
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$349,000 | $157 per sq.ft.
489 Main Street
4 Beds | 2 Baths | Total Sq. Ft. 2220 | Acres: 0.2
This beautifully renovated farmhouse offers a perfect mix of classic charm and modern updates, located just a short distance from the historic town green, shopping, and dining. The home features a spacious living room and cozy family room, providing plenty of space for both relaxation and entertainment. A dining area off the modern kitchen is perfect for family meals or hosting guests. The wood stove in the kitchen provides warmth and ambience The main floor also includes a convenient first-floor bedroom, while the second level features three additional bedrooms, one of which is an excellent option for a home office. You'll also find a large laundry room and a second floor back porch providing access down. Recent updates include new hardwood floors, fresh interior paint, and updated bathrooms. Mini-split systems on both floors provide efficient air conditioning and additional heating for year-round comfort. Enjoy outdoor living with a private fenced in back courtyard, a back porch entry, and a fenced-in backyard. A 1-car garage barn adds extra storage. This home is a dream for outdoor enthusiasts, with major ski resorts including Okemo, Magic, Bromley, and Stratton just a short drive away. The town Recreation Center, pool, and VAST snowmobile trails offer year-round fun, with plenty of biking and hiking trails only a half mile away. Vermont living at its finest--right in town! See
MLS Property & Listing Details & 34 images. Includes a Virtual Tour
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$425,000 | $144 per sq.ft.
196 North Street
3 Beds | 3 Baths | Total Sq. Ft. 2960 | Acres: 0.7
The Simeon Sherwin House, built in 1844, is one of three look-alike houses known as "Three Sisters". The house was owned by Olivia Goldsmith in the 1990's who wrote The First Wives Club. Her worldly, vibrant imprint is still evident in many of the home's unique features. Architecturally, the stone exterior is unique with large blocks (quoins) of schist and mica at the corners. Inside, there is a delightful three season sunroom and formal dining room with woodstove insert, chandelier and an array of full light doors which open to the large, bright kitchen and first floor full bath. A sitting room with a double-sided fireplace connects to the spacious living room. The inviting foyer leads to the second floor which features 3 bedrooms, 2 baths and a sitting room. An addition added by the author and named the Queen's Room during the current owners bnb tenure features built-ins, a partition wall with transom window and a wood stove insert flanked by cozy built-in seats. The primary bath features gold-plated fixtures, a skylight and soaking tub. The first floor also has a heated, retail space for a home business with a separate entrance and office above that has served as an antique shop. The two-car attached, garage has unfinished, overhead space. The exterior needs some sprucing up and a new owner will want to add cosmetic upgrades. The property on .70 acres has a lovely yard with a hydrangea bush, charming bridge, small pond and stone bench overlooking the picturesque village. See
MLS Property & Listing Details & 57 images.
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$469,000 | $121 per sq.ft.
96 S. Main Street
4 Beds | 5 Baths | Total Sq. Ft. 3888 | Acres: 0.53
This spacious 1800's home is filled with Vermont charm and located in the heart of Chester. Filled with natural light from newly installed windows, the home boasts beautiful wood floors throughout and antique door handles that capture the essence of the era. Spacious bedrooms provide ample comfort, while smart thermostats ensure modern convenience. A newly built, covered front porch welcomes you into the home, and a deck off the kitchen leads to an open, level backyard--perfect for gardening or outdoor activities. One of the standout features of this property is the versatile studio space. Accessible via its own entrance from Main Street, this expansive area features vaulted ceilings and two half baths, offering endless possibilities. Whether you're looking to create a storefront, set up an at-home business, or convert the space into a private apartment, the potential is limitless. This property offers a unique opportunity to live in a quintessential Vermont town while having the flexibility to tailor the space to your needs. It's a must-see for anyone seeking a charming, functional home with potential for growth! See
MLS Property & Listing Details & 53 images.
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$509,000 | $390 per sq.ft.
Price Change! reduced by $10,000 down 2% on January 1st 2025
663 Depot Street
3 Beds | 2 Baths | Total Sq. Ft. 1304 | Acres: 1
Step into the charm of yesteryear with all the comforts of today at 663 Depot Street. This completely renovated 3-bedroom, 2-bathroom home combines historic character with modern convenience. Since 2022, everything from the insulation, drywall, electrical, plumbing, & HVAC has been updated, including a new furnace, water heater, fixtures, countertops, cabinets & appliances. The only original feature left untouched is the flooring- beautifully refinished original wood. The owners thoughtfully chose period-appropriate paint colors & preserved unique touches like exposed beams & original woodwork. You'll love the Victorian martini pedestal sink in the upper bathroom! There is also a 2-story attached post-and-beam barn--larger than the house itself--with a powered overhead door. Keep it as a garage or workshop, or explore the incredible potential to double your livable space by finishing it. Sited on 1 acre, the property has a sprawling lawn, fire pit for evenings under the stars & an unbeatable location near Chester's Stone Village, Grist Mill, Smitty's Market, & other local amenities. Just 15 min to Okemo Mtn & the lakes, 30 min to Bromley, & under an hr to Killington, Stratton, & Mt Snow--a prime spot for skiing, hiking, & year-round fun. Currently used as both a family getaway & a successful Airbnb, this property has serious income potential for those looking to maximize its use. Whether you're searching for a primary home or an investment, this timeless home is not one to miss. See
MLS Property & Listing Details & 44 images. Includes a Virtual Tour
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Under Contract
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$1,200,000 | $408 per sq.ft.
Price Change! reduced by $100,000 down 8% on January 4th 2025
354 Miner Road
3 Beds | 4 Baths | Total Sq. Ft. 2941 | Acres: 53.16
Chase Brook Farm is at the end of a quiet country road, offering complete privacy on 53 acres and yet just 10 miles from Okemo Ski Resort, fine dining, and shopping. The views are punctuated by bucolic vistas of the Green Mtns including Steadman Hill, the highest peak in Chester. At the center of this property is a 2,941 s.f. farmhouse, built in 2008 and inspired by countless visits to Sturbridge Village. Thoughtfully designed to evoke the charm of a historic home, it features hand-planed boards, painted wide pine floors, wrought iron latches, and soapstone countertops while providing the comfort of modern amenities, including new mechanicals, updated wiring, and a large, dry basement. This property invites year-round enjoyment. In winter, sled down hills out back, or clear the pond for skating parties. Snowmobilers, skiers, and snowshoers will appreciate the room to roam and easy access to the VAST trail. After a day in the snow, warm up by one of the two cozy fireplaces or take a soak in the hot tub. In summer, enjoy a swim or cast a line in the stocked pond, or gather berries from the 80+ blueberry bushes and raspberry patch. The fall season brings apple picking and the land is suitable for livestock, offering versatility for a variety of uses. Chase Brook weaves in and out along the border to the East. Additional features include an attached 1-bay garage, a 3-bedroom caretaker's house with a 3-bay garage, and fiber optic internet. Showings begin October 11. See
MLS Property & Listing Details & 37 images. Includes a Virtual Tour
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Under Contract
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$1,995,000 | $528 per sq.ft.
Price Change! reduced by $350,000 down 18% on September 27th 2024
1328 Chandler Road
4 Beds | 4 Baths | Total Sq. Ft. 3779 | Acres: 193
Design inspired by Frank Lloyd Wright this mid-century modern home is a beacon of tranquility for those looking for privacy. Surrounded by 193 acres including 13 acres of open pasture traced with ancient stone walls. Enjoy more than 2 miles of trails crossing brooks and fields. This magnificent haven for lots of wildlife has apple trees, raspberry bushes and more than 50 blueberry bushes. Inside a wide-open main living area and great room overlooks the 10 foot deep swimming pond, and the nearby stream can be heard from the deck or kitchen with the windows open. Step into the luxurious primary suite, a sanctuary with large windows and a spa inspired bath with a free-standing tub that boasts one of the best views from the house. Enjoy the newly renovated lower level with additional bedrooms and expansive family room. This area is ready for your touch and enjoys walkout access to the yard and pond. The 2nd level of the barn is currently a wood shop with wood-stove and a 2nd access from the road allows for storing large pieces or equipment on this upper level. The ground level of the barn has traditional sliding barn doors and extensive parking in front. Underground power and water lines travel from the house to a nearby site where another barn or horse arena could be built. A unique home treasure and like its organic architectural design the land has its own special quality of character and beauty. 191 acres are in the VT Land Use program. There is a 6 bedroom septic. See
MLS Property & Listing Details & 52 images. Includes a Virtual Tour
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