Chester Homes for Sale

**Discover the Charm of Chester: Your Next Home Awaits**

Nestled in the heart of Cheshire, Chester is a city that beautifully marries history with modern living. Renowned for its stunning Roman walls, medieval architecture, and vibrant cultural scene, Chester offers a unique blend of old-world charm and contemporary convenience. Stroll along the picturesque River Dee, explore the iconic Chester Zoo, or indulge in shopping at the quaint boutiques and popular high street stores. With its rich heritage and lively atmosphere, Chester is not just a city; it's a community where people thrive.

For those considering making Chester their home, the real estate market is as diverse as the city itself. From charming period properties that reflect the city’s historical significance to modern family homes nestled in peaceful neighborhoods, there’s something for everyone. Whether you’re a first-time buyer or looking to upgrade, Chester offers a variety of homes for sale that cater to different lifestyles and budgets.

Imagine living in a beautifully restored Victorian townhouse with original features, or a sleek contemporary apartment with stunning views of the city skyline. Families will appreciate the spacious homes in well-established suburbs, complete with gardens and proximity to excellent schools.

With its friendly community spirit, excellent transport links, and a plethora of amenities, Chester is an ideal place to settle down. Explore our listings today and find your dream home in this enchanting city. Chester is waiting to welcome you home!

Newest Chester Homes for Sale

$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

$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

$545,000

3 Beds ⋅ 2 Baths ⋅ 5112964 MLS

Welcome to 124 Haverhill Road, a well-cared-for raised ranch on a beautifully landscaped lot in Chester, NH. Mature pear, cherry, apple and peach trees, along with blooming magnolias and established plantings, frame the property with color in spring and a harvest each season. The main level features gleaming hardwood floors throughout. The spacious living room is bright with natural light and recessed lighting. Near the entry, a pellet stove set on a classic brick hearth adds cozy warmth and helps keep heating costs down. The eat-in kitchen offers two ways to dine: a large center island with seating for three, perfect for quick breakfasts and casual conversation, plus a separate dining area with room for a full-size table, set beside a sunny picture window. Plenty of wood cabinet storage and pendant lighting complete the space. Three bedrooms include a primary bedroom with its own private 3/4 bath, plus a full bath for a total of 1.75 baths. Step out back to the three-season porch overlooking the private yard, a relaxing spot for quiet evenings or entertaining from spring through fall. The partially finished lower level has been updated with brand-new luxury vinyl plank flooring and features a second stove on a brick hearth, ready for a rec room, home office or gym. The one-car garage under offers everyday convenience and extra storage, and the driveway has been recently paved. Small-town Chester living with easy access to Derry, Manchester and I-93.

124 Haverhill Rd, Chester

$39,000

73586614 MLS

Unique Property with Multiple Outbuildings and Versatile Use Potential Discover a rare opportunity in Chester — a property offering multiple outbuildings, upgraded utilities, and flexible space for storage, recreation, or future development.The land includes two well-built sheds:Utility Shed — insulated, equipped with electric heat, and houses the well pump, providing reliable year-round functionality. Cabin-Style Shed — transformed into a comfortable retreat with 200-amp electrical service, electric heat, and full insulation, making it ideal as a workshop or hobby space.A metal shipping container on the property adds substantial secure storage for equipment, tools, or recreational gear. Whether you’re looking for a getaway spot, a base for outdoor activities, or a property with ready-made utility structures, this location offers exceptional versatility.

2 Taft Rd, Chester

$229,000

2 Beds ⋅ 1 Baths ⋅ 5112828 MLS

Sometimes, just the right amount of space is exactly what you need. Set on two pleasant acres in Chester, this tidy 2-bedroom, ¾-bath home offers comfortable, efficient one-level living with a practical layout that makes everyday life easy. Inside, the home is bright and well cared for, with a modern kitchen, comfortable living space, two nicely sized bedrooms, laundry, and the convenience of everything on one floor. Propane heat keeps things simple and efficient, while the manageable footprint means less house to maintain and more time to enjoy Vermont. Outside, the level lawn provides plenty of usable space for gardening, pets, a fire pit, or simply relaxing outdoors without taking on an overwhelming property. A detached two-car garage offers excellent parking, storage, and room for the tools and gear that come with Vermont living. Whether you're looking for a first home, ready to simplify, or searching for a comfortable retirement property with minimal stairs and manageable upkeep, this Chester home checks a lot of boxes. Simple, practical, and easy to maintain, it is a home that makes perfect sense.

547 Andover Rd, Chester

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Chester Homes for Sale

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