Properties Near 284 Flamstead Road Chester, VT

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!

Open House Thursday, September 11, 4:00 - 6:00 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. Recent upgrades include a brand new three bedroom septic system, making expansion a future option and a detached two car garage that offers excellent storage for vehicles, ski gear, or workshop space, along with an electric car charging station hookup. The property is dotted with mature sugar maples, already tapped, bringing an authentic Vermont sugaring tradition right to your doorstep. Just minutes from Chester‘s, charming Village center, and Springfield amenities, and a short drive to Okemo Mountain resort, this location is ideal for year-round, living, a ski getaway, or a weekend retreat. Whether you’re seeking a low maintenance primary residence or a charming, second home, this property blends, rustic appeal with modern convenience in quintessential Vermont setting.

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.

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.

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, which is a great space to store the skis, poles and helmets from a great day of skiing. The main level features a generous living room anchored by a classic wood-burning fireplace ideal for cozy winter evenings. The sunny eat-in kitchen provides ample space for meals and gatherings, while the full bath with laundry adds everyday practicality. All windows were replaced in 2019, offering energy efficiency and bright natural light throughout. Upstairs, you'll find three spacious bedrooms, including a stunning turret space that creates a bright and airy nook perfect for reading or relaxing under the sun-drenched windows. The original woodwork and architectural details throughout highlight the craftsmanship of a bygone era. Outside, the covered wrap-around porch invites you to unwind and enjoy the peaceful sounds of the nearby babbling brook. Take a short stroll to the local market or explore the picturesque village with its shops, restaurants, and small-town charm. This home is more than just a place to stay it’s a place to create lasting memories. All only 15 miles from Okemo Mountain!

Tucked back from the paved road and surrounded by woods, this charming 3-bedroom, 1.5-bath home offers both privacy and convenience. With a little updating and personal touch, it has all the makings of a wonderful starter home or the perfect Vermont getaway. Ideally located near several major ski areas and the lakes region, you’ll enjoy year-round recreation — from winter skiing to summer days on the water. A true four-season retreat waiting for its next chapter! Best suited as cash or conventional purchase.

Looking to live near the Chester Green? This may be the home for you! Currently used as a four-unit apartment building I believe that the highest and best use would be to return it to a single-family home with one accessory apartment in the back. The house is in need of renovation however, the style and location would lend well to that investment, or renovate the four units as your next venture, either way you will have a fine home near the center of all that Chester has to offer!

Cozy and Full of Potential! Tucked away in a quiet neighborhood yet close to all local amenities, this inviting home offers the ease of one-level living. With just a little finishing work, it can become the perfect retreat after a long day. Enjoy a spacious yard, a sunny setting, and the convenience of a one-car under garage. The home has already seen several updates, including a new kitchen, fully insulated walls, and some new windows. The property is being sold as-is and will require a few finishing touches—such as exterior painting and interior trim work. Please note: due to chipping and peeling exterior paint and some interior trim and drywall work needed, the home will not qualify for government financing. Cash, rehab loan, or conventional mortgage depending on the lender, is the best option. This home is a fantastic opportunity to add your personal touch and build equity. Don’t miss out—schedule your showing today!