Chester Homes for Sale

Welcome to Chester, a picturesque city nestled in the heart of Cheshire, England. With its rich history dating back over 2,000 years, Chester is a vibrant blend of ancient charm and modern convenience. The iconic medieval walls, stunning Roman amphitheater, and the enchanting Rows—unique two-tiered shopping galleries—create an atmosphere that is both captivating and inviting. The city boasts beautiful parks, such as Grosvenor Park and the Riverside, offering residents picturesque spots to unwind and enjoy nature. Chester’s thriving arts and culture scene, complemented by numerous festivals and events throughout the year, ensures there’s always something exciting happening.

For those considering a move to this delightful city, Chester offers a diverse range of homes for sale, catering to various tastes and lifestyles. From elegant period properties with historical significance to contemporary new builds designed for modern living, there’s something for everyone. Families will appreciate the spacious townhouses and charming cottages nestled in quiet neighborhoods, while professionals might find sleek apartments in the city center to be the perfect fit.

Chester’s excellent transport links make it easy to commute to nearby cities such as Liverpool and Manchester, while the city itself is home to top-rated schools and a strong sense of community. With a vibrant dining scene and a plethora of shops, Chester is not just a place to live, but a place to thrive. Explore the homes for sale in Chester today and discover the perfect property that aligns with your lifestyle in this enchanting city!

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

$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

$524,900

3 Beds ⋅ 2 Baths ⋅ 5112964 MLS

New price! The expensive work is already done in this 3-bedroom, 1.75-bath raised ranch, set on a private 0.62-acre wooded lot in Chester. Major updates include a newer architectural roof, a freshly paved driveway, and a newly finished lower level with brand-new LVP flooring. A pellet stove on a classic brick hearth keeps winter heating costs down. Upstairs, hardwood floors run throughout the bright main level. The eat-in kitchen has a large center island, generous cabinet space and room for a full dining table. The living room has recessed lighting, and the sunroom looks out over the back deck and wooded backyard. The primary bedroom has its own ¾ bath. The lower level adds flexible space for a rec room, home office or gym, with walls primed and ready for your colors. About 1,676 sq ft on the main level, plus a one-car garage under. Quiet setting with an easy commute to Derry, Manchester and I-93. Served by Chester Academy (PreK–8) and Pinkerton Academy (9–12); buyer to verify school assignment.

124 Haverhill 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

$789,900

3 Beds ⋅ 3 Baths ⋅ 5112505 MLS

The Eagle Farmhouse blends a classic colonial layout with a fresh, modern exterior. Step inside and you'll love the spacious open-concept design, perfect for both everyday living and entertaining! The kitchen features beautiful quartz countertops, ample cabinetry, and a seamless flow into the main living areas. Conveniently located off the garage, the mudroom provides the perfect drop zone for coats, shoes, and everyday essentials. A versatile den offers an ideal space for a home office, playroom, or guest area, while the inviting family room provides plenty of room to relax by the fireplace and gather with family and friends. Thoughtfully designed with comfort and functionality in mind the second floor offers two spacious bedrooms with walk-in closets, a dedicated laundry room, a full bath, and a spacious primary with en-suite with a lovely tiled walk-in shower designed to satisfy even the most discerning homeowner. Beautiful hardwood and tile flooring throughout. The full basement could be finished later for future additional living space if desired. Pet friendly and no age restrictions. Come and see what this small, charming community of detached condos in desirable Chester, NH has to offer. Builder's last home at Pipit Estates - do not miss out!

11 Robin Way Unit 2, Chester

$699,900

3 Beds ⋅ 3 Baths ⋅ 5112319 MLS

Here is your opportunity to get into Chesterbrook Estates! Welcome to 98 Lady Slipper Lane. Set in a private neighborhood, this 3-bedroom Colonial home in Chester NH offers 2.5 baths, approximately 3,260 square feet of finished living space across three levels, and more than 1.25 acres. Priced under $700,000, this 2004-built home pairs a spacious floor plan with a peaceful setting overlooking a serene pond. Inside, you'll find plenty of room to spread out, including a large family room designed for comfortable everyday living and gatherings. Three finished levels provide added flexibility, highlighted by a third-floor bonus room that expands the possibilities for additional living, work, recreation, or hobby space. Need more space? The walk-out lower level offers future expansion possibilities. Outside, the back deck creates an inviting place to enjoy the natural surroundings and pond views. Additional features include a newer roof and two-car garage and whole house pellet stove heating system that is connected to the duct work. Enjoy the private oasis in your back yard, while still benefitting from a neighborhood setting. All of this and part of the Pinkerton Academy School District, this is one that you will not want to miss out on. Schedule your private showing today!

98 Lady Slipper Ln, Chester

$569,000

3 Beds ⋅ 2 Baths ⋅ 5112156 MLS

Welcome to your own private retreat on 2.2 picturesque acres in beautiful Chester, New Hampshire! Set back on a peaceful lot surrounded by nature, this charming single-family home offers the perfect blend of peaceful country living, thoughtful updates, and everyday comfort. Inside, you’ll find 3 bedrooms and 1.5 newly renovated bathrooms, along with an inviting, recently updated kitchen featuring quartz countertops, a stylish tile backsplash, and brand-new stainless-steel appliances. The bright eat-in kitchen is made even more welcoming by a beautiful bay window, creating a wonderful spot to enjoy morning coffee or casual meals while taking in the view. Warm bamboo flooring & new carpet throughout the home, while the brick wood-burning fireplace adds a cozy focal point for relaxing evenings in the living room. One of the home’s true showstoppers is the breathtaking screened-in porch, a serene space surrounded by nature where you can unwind, entertain, dine, & relax to the sounds of the outdoors. The 20x22 basement provides ample bonus space, as well as a half bath, laundry, & plenty of storage options. Step outside and discover everything this special property has to offer. The expansive, private lot features an open field, mature apple trees, a small barn, and a shed with electricity, providing plenty of space for hobbies, gardening, storage, animals, or simply enjoying the outdoors. Whether you’re seeking a peaceful place to call home or a property that allows you to fully embrace the beauty of nature, this Chester gem offers a rare opportunity of privacy, charm, and modern updates. Come experience the setting, explore the possibilities, and discover all this special property has to offer.

136 Haverhill Rd, Chester

$620,000

3 Beds ⋅ 3 Baths ⋅ 5111937 MLS

Tucked into a private setting in the charming town of Chester, this 3-bedroom, 2.5-bath home offers plenty of space, natural light and a few unexpected surprises! The updated kitchen features granite countertops, stainless steel appliances, ample cabinetry and workspace, while radiant heat adds warmth and comfort throughout. Upstairs, the primary suite is a standout, featuring a beautifully appointed, luxurious private bath and access to its own balcony overlooking the natural surroundings, a peaceful spot to enjoy your morning coffee or unwind at the end of the day. Two additional bedrooms and another bath complete the upper level. Need more space? The finished lower level provides flexible bonus space for a family room, home office, gym or playroom, along with plenty of additional storage. Set back in a peaceful location with wonderful sun exposure and a sense of privacy, this home offers an opportunity to enjoy the quieter side of New Hampshire living while remaining convenient to surrounding towns, shopping and commuter routes. Bring your vision and make this Chester home your own!

21 Smith Rd, Chester

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Chester Homes for Sale

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