Chester Real Estate

Welcome to Chester, a city steeped in history and charm, located in the heart of Cheshire, England. Known for its stunning architecture and rich heritage, Chester is a delightful blend of ancient and modern, offering something for everyone. With its iconic Roman walls, medieval timber-framed buildings, and the picturesque River Dee, the city paints a captivating picture that enchants both residents and visitors alike.

Chester boasts an array of amenities, including boutique shops, vibrant cafes, and award-winning restaurants that cater to diverse tastes. The bustling city center is a hub of activity, where you can explore the unique Rows—two-tiered shopping galleries that provide a shopping experience like no other. For those who appreciate nature, the beautiful Grosvenor Park and the serene River Dee offer tranquil spots for leisurely walks or picnics.

Education is a priority in Chester, with several well-regarded schools and the University of Chester, which attracts students from around the globe. This commitment to education enhances the community's vibrant atmosphere, making it an ideal place for families and young professionals alike.

Chester is also conveniently located, with excellent transport links to major cities such as Manchester and Liverpool, making it an ideal base for commuters. The blend of historical charm, modern conveniences, and strong community spirit makes Chester not just a place to live, but a place to thrive.

Whether you’re looking to buy your first home, invest in property, or simply explore the area, Chester beckons with its unique allure and warm hospitality. Come and discover the magic of Chester—where history meets modern living!

Newest Listings in Chester

$269,000

4 Beds ⋅ 1 Baths ⋅ 5115637 MLS

Welcome to this comfortable Cape-style home in Chester, Vermont, offering a wonderful combination of classic charm, practical features, and flexible living space. Whether you’re looking for a place to call home or a property with room to make your own, this home has plenty to offer! The property features a durable standing seam metal roof, double-pane vinyl windows, and beautiful hardwood floors throughout most of the main level. The inviting layout provides comfortable everyday living, while the level lot offers usable outdoor space for gardening, relaxing, entertaining, or enjoying the seasons in Vermont. An oversized one car garage provides convenient parking along with additional room for storage, tools, or recreational equipment. Downstairs, you’ll find a finished office or bonus room with its own exterior access, creating a versatile space for working from home, pursuing hobbies, setting up a home gym, or accommodating your changing needs. Located in the charming town of Chester, this property offers an opportunity to enjoy small town Vermont living while making the most of a home with appealing features and flexible spaces. With its practical updates, hardwood flooring, usable yard, and bonus room potential, this Cape-style home is ready for its next owner to make it their own. Come see all that this property has to offer!

426 Vermont Route 103, Chester

$229,900

2 Beds ⋅ 2 Baths ⋅ 73594709 MLS

Welcome to this historic Colonial home nestled in the center of Chester, offering charm and modern potential. Featuring 6 spacious rooms, including 3 generous bedrooms and 1.5 bathrooms, this home is ideal for Living, investors, or those seeking an Airbnb rental opportunity. Inside, enjoy the warmth of beautiful wood floors throughout most of the home, a large kitchen with ample counter and cabinet space, and closets galore for all your storage needs. Additional features include a spacious three-season front porch that’s surrounded by natural light accented by a beautiful wood ceiling, vinyl windows, an attached 1-car garage, and a storage shed — all situated on a 0.36-acre lot. Located along the scenic Westfield River, this property is a haven for outdoor lovers, with nearby hiking and riding trails, and is just a short drive to Jacobs Pillow, Tanglewood, Lee Outlets, and only 30 minutes to Westfield or the Berkshires.

254 Route 20, Chester

$495,000

3 Beds ⋅ 2 Baths ⋅ 73594566 MLS

Custom-built Contemporary is ready for its second owner. Perfect blend of comfort, privacy and natural beauty on 9.7 acres. Meander on the 9.7 acres with a babbling brook that can be heard from the front porch. There are distant mountain views, not visible from the house. The main floor features a kitchen with cabinets galore and a wine frig, cathedral ceiling in the dining room with a fireplace, generous size living room with views to the outside, two bedrooms and a bathroom. The second floor features a generous size bedroom with a private bathroom and an open sitting area that could function as a study. Partially finished basement with a room that functioned as a prior wine cellar. The kitchen and bathroom were updated 14 years ago, approximately. The roof was replaced in 2010 and the heating system in 2012. There is enough frontage for the potential for another lot or lots, buyer to verify, the property is being sold as one lot. The seller is installing a new septic system.

47 Lyon Hill Rd, Chester

$1,100,000

4 Beds ⋅ 4 Baths ⋅ 5115257 MLS

A Home for the Holidays is calling. Tranquility awaits at this remarkably private, hilltop sanctuary set on 22.49 acres. A winding 700-foot driveway guides you past a serene pond, expansive stone walls, and mature landscaping. Custom-built this elegant 12+ room Cape seamlessly blends timeless character with modern luxury. Featuring 1,700 feet of road frontage, the property offers exceptional privacy, potential in-law accommodations, and room for entertaining. Inside, 9-foot ceilings, crown molding, and hardwood flooring run throughout the first floor. The main level opens to a soaring cathedral foyer with a balcony overlook, leading into a light-filled living room anchored by gorgeous stone fireplace. The gourmet kitchen boasts cherry cabinetry, granite countertops, a porcelain tile floor, a wine cooler, and a professional-grade 6-burner stove. An adjacent breakfast nook opens directly onto the rear deck for effortless indoor-outdoor living. A large coffered ceiling family room and dining room complete the first-floor entertaining spaces. The primary bedroom is a retreat featuring a large walk-in closet and a spa-like bath with double console sinks, a walk-in dual shower, and a 6-foot slipper clawfoot tub. A dedicated main-floor library/office with pocket doors and a mahogany-floored three-season porch with wood-paneled walls complete the level. Upstairs, find three spacious bedrooms, a full bath, a large flexible bonus room to suit your needs and a walk-in attic. The walk-out basement is built for multi-generational living, offering a recreation room, with a back-lit coffered ceiling, a stone fireplace, an additional bedroom, a 3/4 bath, an outdoor shower, and a custom wet bar with maple cabinets. Other amenities include a finished two-car garage with architectural doors, EV Charger, workshop area, shed, generator ready, top-tier mechanical systems and wired for an outdoor hottub. With over 270 acres of conservation land abutting the lot, this one is special!

545 Lane Rd, Chester

$549,000

4 Beds ⋅ 2 Baths ⋅ 5115206 MLS

Beautifully built country home with lots of extras. Large kitchen features a brick hearth perfect for a wood stove, a large eating area, formal dining room with fireplace.

204 Fletcher Rd, Chester

$949,900

3 Beds ⋅ 2 Baths ⋅ 5114966 MLS

Discover the perfect blend of country living and equestrian functionality, all within walking distance to the charming center of Chester. Set on 9.6 picturesque acres, this well-maintained horse property offers approximately 5 acres of lush, verdant pasture, complemented by wooded areas that provide beauty, privacy, and endless riding enjoyment. The equestrian facilities include two barns with a total of four horse stalls and one pony stall. The barn setup is equipped with hot and cold running water, and an insulated tack room that provides comfortable year-round storage and workspace. The inviting home offers just under 2,300 square feet of living space with a warm, functional layout. Featuring three bedrooms and two full baths, the home showcases beautiful hardwood floors, a bright and spacious kitchen, and a bonus room ideally suited for a home office, hobby space, or den. First-floor laundry adds to everyday convenience. Just off the kitchen, a charming, screened porch provides the perfect place to relax and take in the natural beauty that surrounds you. Enjoy peaceful mornings with a cup of coffee, listen to the sounds of nature, and watch the changing seasons unfold from this tranquil retreat. Outside, the backyard also features a dedicated fenced-in area, offering a safe and versatile space for pets, play, or gardening. Lovingly cared for and thoughtfully updated, the home boasts improvements including vinyl siding, an updated heating system, a whole-house water filtration system, and much more. Whether you're an avid equestrian, hobby farmer, or simply seeking a peaceful country lifestyle with modern comforts, this rare Che

47 Wells Village Rd, Chester

$129,900

2 Beds ⋅ 1 Baths ⋅ 5114929 MLS

This cozy home presents so many opportunities-Live here, vacation here, rental property, renovate as you want and flip, ski home! Offering 2 bedrooms, 1 full bathroom, eat in kitchen/dining room, and living room. Outside is a great 1 car garage with plenty of space for all your tools, lawnmower, etc. Set right in the town of Chester in short walking distance to stores or the town green with wonderful coffee shops and other great shops! Close to ski areas, hospital, schools, and much more, whatever you are looking for this single floor home could check all your boxes! Or would make a great investment property with a little work! Call for your appointment today.

473 Elm St, Chester

$105,000

5114886 MLS

As a neighbor, I can vouch for this location... Discover the perfect setting for your Vermont dream home on this beautiful 3+ acre parcel located along Route 103 in Chester. For 23 years I have driven by this lot on my way to Okemo... No traffic just a zen like 15 minute drive along the Williams River. A super convenient location with easy access to town amenities, shopping, dining, and nearby ski resorts, this property combines the charm of a country setting with year-round convenience. The gently sloping, partially wooded landscape features beautiful mature trees and classic New England stone walls, adding character and natural beauty to the property. Whether you envision a cozy country retreat or a full-time residence, this parcel offers an opportunity to create your own Vermont getaway in a desirable location close to outdoor recreation and all that the Okemo Valley has to offer. Visit the Okemo real estate community today. (survey and ww permit for a 3br septic available also abutting lot is also available for sale)

Lot 4 Vt Route 103, Chester

$105,000

5114885 MLS

Lot 3 Vt Route 103, Chester

$114,900

3 Beds ⋅ 2 Baths ⋅ 5114547 MLS

Bring Your Vision to Life in Beautiful Chester, Vermont! Discover the potential of this partially constructed A-frame home nestled on approximately 2 acres along VT Route 11 in scenic Chester, Vermont. Offering approximately 980 square feet of planned living space, this 3-bedroom, 2-bathroom property presents an exciting opportunity for investors, builders, contractors, or buyers looking to create a personalized Vermont retreat. The renovation is awaiting a complete build-out, including windows, doors, and all interior and exterior finish materials, allowing the next owner to take the project from its current stage to a finished home tailored to their vision. With its distinctive A-frame design and nearly 2 acres of land, the property offers a blank canvas for a weekend getaway, year-round residence, or investment opportunity. Enjoy the possibilities of owning a property in the charming town of Chester, surrounded by Vermont's natural beauty and four-season appeal. Bring your plans, creativity, and finishing expertise to transform this unfinished project into something special. Property is being sold in its current, unfinished condition. Buyers should perform their own due diligence regarding construction requirements, permits, utilities, and completion costs.

4351 Vermont Route 11 W, Chester

$290,000

3 Beds ⋅ 2 Baths ⋅ 73589335 MLS

Very well-maintained home on dead end street within walking distance to store, 2 restaurants and library. Walk out onto the back deck, to a nice size yard, with the West Branch of the Westfield River in your back yard. Come home and stick your toes in the water and relax to the serene sound of the babbling river, after a long day. 2 story conventional style home with 6 rooms, 3 bedrooms, 1.25 baths, 1 car attached garage and a cute front porch. Title V failed, perc test done, design completed and out for bid. and new septic system to be installed. Same owner for 50 years and it is time for new owners to enjoy this ready to move in home. Be in for the holidays. Don't miss this sweet home.

27 Maple Ave, Chester

$624,900

2 Beds ⋅ 3 Baths ⋅ 5113580 MLS

Welcome to 256 Villager Road, a beautifully upgraded ranch style condo offering a unique floor plan, exceptional living space and one of the more private settings in the community. Surrounded by woods to the left and rear, this home enjoys a peaceful setting with no neighboring condo on one side or directly behind. Inside, hardwood floors flow throughout the first floor, where a spacious family room at the front of the home takes the place of the typical second bedroom, creating an inviting and open layout for everyday living and entertaining. The kitchen features granite countertops, a large center island, stainless steel appliances, including a gas range, and plenty of workspace and storage. The primary suite is a true retreat with a large soaking tub, oversized walk-in shower and double sinks. A convenient first-floor half bath includes laundry hookups, offering the option for one level living. An inviting sunroom provides the perfect place to relax and enjoy the peaceful surroundings and leads directly to a spacious deck overlooking the wooded setting, ideal for morning coffee, outdoor dining or entertaining. The attached two car garage provides easy access to the home with just two steps inside and an oversized entry door. The finished walkout lower level significantly expands the living space and offers tremendous flexibility. Here you’ll find a large family room, bedroom, office/study and a full bath with double sinks, along with an additional set of laundry hookups. Whether you’re looking for space for guests, a home office, hobbies or a separate living area, this level offers plenty of possibilities. Enjoy low maintenance condo living along with community amenities including an inground pool and clubhouse. With its upgraded finishes, flexible floor plan, generous living space and exceptionally private location, 256 Villager Road offers the space and comfort of a single-family home with the convenience of condominium living.

256 Villager Rd, Chester

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Chester Real Estate

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