Chester Homes for Sale

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

$749,000
4 Beds ⋅ 2 Baths ⋅ 5101760 MLS
Discover the perfect blend of rustic elegance and modern versatility at 34 Edwards Mill Road. Set on 3.89 expansive acres in the scenic countryside of Chester, NH, this stunning log home offers a serene lifestyle for any stage of life. Are you looking for a natural playground where you can explore the woods and the soothing waters of Towle Brook, or wanting a peaceful New Hampshire retreat with single-level living potential, this property delivers. The spacious interior has been thoughtfully maintained with fresh paint, featuring 9 spacious rooms including 4 bedrooms and 2 full bathrooms. The home’s flexible layout includes a first floor primary bedroom suite that opens directly into a gorgeous huge sunroom. For those prioritizing convenience, the first-floor separate laundry room facilitates true single-level living options. Recent updates ensure peace of mind, including log maintenance, new gutters, and freshly seal-coated driveway. Outdoor enthusiasts and hobbyists will fall in love with the substantial detached 3-car garage which features a brand-new roof, a convenient drive-through bay with heat and water access. Above, an enormous unfinished space presents incredible potential for a studio, storage, or an accessory dwelling unit (ADU), subject to approvals. Outside, the enormous 50 ft. deck provides the ultimate spot for hosting gatherings or simply relaxing to the sounds of the brook winding through your private acreage. Experience total privacy without sacrificing accessibility; this retreat is located just 25 minutes from the Massachusetts border and approximately one hour from the heart of Boston. This home has been lovingly cared for and is ready for its next chapter. Schedule your private tour today to experience the charm & serenity of this stunning Chester retreat. You won't want to leave.

34 Edwards Mill Rd, Chester
$925,000
5 Beds ⋅ 3 Baths ⋅ 5099745 MLS
Escape to the charm of Vermont in this spacious 5-bedroom, 3-bath country home, perfectly set amidst open meadows with a picturesque swim pond and peaceful surroundings. Designed for both everyday living and entertaining, this inviting property offers the perfect balance of rustic character and modern comfort. Step inside through the practical mudroom, where you'll be welcomed by a dramatic family room featuring soaring vaulted ceilings, a cozy wood-burning stove, and a loft overlooking the space. The heart of the original 1860's home is the open-concept living area, complete with a well-appointed kitchen, dining area, and a warm, inviting living room centered around a classic wood-burning fireplace. The main level also features a convenient half bath and a private primary suite with a ¾ bath. From the primary bath, step directly onto the back deck and unwind in the sunken hot tub while taking in the tranquil country setting. Second level, you'll find four additional bedrooms, a full bath, and a comfortable den/loft overlooking the family room, offering flexible space for guests, a home office, or recreation. Outside, enjoy Vermont's beauty from the private covered porch, gather around the expansive yard, or relax by the stone firepit or scenic pond surrounded by open meadows. An attached garage provides ample storage, while the finished game room above creates the perfect space for entertaining, hobbies, or additional guest accommodations. The flat meadows were the perfect setting for the family's recent wedding... What event will you host in this incredible backyard? Ideally located just minutes from the charming village of Chester and within easy reach of Okemo Mountain Resort, this exceptional property offers year-round enjoyment, whether you're seeking a full-time residence, a vacation getaway, or an investment opportunity. Visit the Okemo real estate community today. Taxes are based on town assessment.

1470 Popple Dungeon Rd, Chester
$199,000
2 Beds ⋅ 1 Baths ⋅ 5098053 MLS
Set on 18 forested acres along quiet, dead-end Potash Brook Road in Chester, this peaceful cabin offers a simple and inviting Vermont retreat with no through traffic and a true sense of calm. Well suited for a hunting camp, recreational getaway, or quiet place to unwind, the property provides privacy, natural surroundings, and easy access to the outdoor lifestyle Southern Vermont is known for. The cabin includes propane heat, a spring well, septic, and an inviting and cozy living space for weekends, seasonal use, or time away from the noise of everyday life. The structure will require new footings and is being sold as is, offering an opportunity for the next owner to make needed improvements while enjoying the land, setting, and existing cabin. The property is wooded and rustic in feel, with room to explore, observe wildlife, and enjoy the changing seasons. A brook runs through the land, adding natural character to the setting. Whether used as a base for hunting, hiking, snowmobiling, skiing, or simply relaxing in the woods, this property offers a practical and appealing Vermont escape. Ski areas, trail networks, fishing, and year-round recreation are all within reach, while the setting itself remains quiet, private, and refreshingly simple. If you are looking for land, privacy, and a modest cabin with key systems already in place, this Chester retreat is well worth a look.

1372 Potash Brook Rd, Chester
$850,000
4 Beds ⋅ 3 Baths ⋅ 5097911 MLS
Looking for a 4-bed colonial in Chester with space, privacy, and an ideal layout for entertaining? Welcome to 43 Emerson Road Where timeless Colonial charm meets comfortable everyday living. This well-maintained home set on two private acres is in a desirable cul-de-sac neighborhood. Enjoy spacious living areas, inviting outdoor spaces. Nestled on 2 private acres in a peaceful cul-de-sac neighborhood, this 4-bedroom, 3-bathroom Colonial offers the perfect balance of privacy, community, and convenience. The open and inviting first floor is designed for both daily living and entertaining, featuring a spacious kitchen, formal dining room, and an expansive family room with a soaring vaulted ceiling and cozy gas fireplace. New carpeting adds a fresh touch, making this home move-in ready. Step outside to your own backyard retreat featuring a multi-tiered deck, sparkling pool, and a private outdoor oasis designed for summer gatherings, barbecues, and relaxing evenings with family and friends. The generous two-acre lot provides room to play, garden, or simply enjoy the peaceful natural surroundings. Not far from shopping, dining, recreation, and major commuter routes while still offering the charm and tranquility that make Chester one of southern New Hampshire's desirable communities. Served by the highly regarded Pinkerton Academy school district. Whether you're hosting memorable celebrations or enjoying quiet evenings at home, this property delivers the lifestyle you've been searching for. Come experience everything 43 Emerson Road has to offer and discover why so many are proud to call Chester home. Schedule your private showing today. Showings begin Monday July 6, 2026

43 Emerson Rd, Chester
$649,000
3 Beds ⋅ 2 Baths ⋅ 5097737 MLS
Welcome to your private gated mini-estate...an enchanting sanctuary where every detail delights the eye. Nestled adjacent to meticulously manicured woods, this one-of-a-kind residence blends storybook charm with thoughtful, high-end finishes. A sweeping entry leads past intimate outdoor living spaces centered around a dramatic floor-to-ceiling exterior fireplace, perfect for cool evenings and quiet reflection. Step inside to discover warm, curated interiors where a matching floor-to-ceiling indoor fireplace anchors a cozy great room...an ideal focal point for gatherings and quiet nights in. The custom kitchen is a chef’s and designer's showcase making meal prep effortless and stylish. Cute, artful decor and exceptional millwork accentuate every room..every little detail has been considered and executed with eye-popping precision. Natural light pours through thoughtfully placed windows, highlighting textures, finishes, and curated vignettes around nearly every corner. In addition to the four private bedrooms, the special loft above the second-floor den offers a “fun” sleeping area and great retreat for the “kids”. Unique sightlines and charming nooks reveal something special at every turn.unexpected architectural details, refined accents, and cozy gathering spots create a home rich in personality and comfort. The floorplan flows intuitively while offering distinct spaces for entertaining and everyday living. Practicality meets luxury with a spacious second garage providing room for toys, workshop space, or secure storage perfect for multi-vehicle households or hobbyists. The gated setting ensures peace of mind and exclusivity, while the manicured wooded grounds offer a serene backdrop and a strong connection to nature. Come see how every corner captures your attention and inspires a sense of wonder at home. This mini-estate is only 10 miles from world-class skiing at Okemo and golf at Fox Run...then enjoy the 5 lakes of Okemo Valley and the nearby VAST trails!

168 Chandler Rd, Chester
$750,000
3 Beds ⋅ 2 Baths ⋅ 5097722 MLS
Tucked away on a quiet country road in one of Chester’s most coveted areas, this striking contemporary home offers the ultimate Vermont lifestyle, just miles from the Okemo Mountain base lodge. Embraced by nature and thoughtful landscape, the property seamlessly connects refined indoor living with the natural beauty of its private riverfront, complete with your own summer swimming hole. Inside, the main level centers around a commanding, floor-to-ceiling fieldstone wood-burning fireplace, beautifully complemented by rich hardwood floors and a bespoke custom kitchen. Designed for privacy, the primary suite features a spa-like ensuite bath, while two additional guest bedrooms and a 3/4 bath provide plenty of space for family or weekend visitors. Intelligently designed for flexible living, the upper-level loft serves as an inspiring home office or studio, while the bright, walk-out lower level offers incredible potential for a game room, home gym, or ski lounge. Transition effortlessly outdoors to the oversized front deck for morning coffee, or unwind in the expansive screened porch out back listening to the sound of the river. The detached, insulated, oversized, 2-bay, 2-level barn has full electrical service, electric garage doors, and a workshop with extra storage space. There is a greenhouse perfect for gardening. With direct access to nearby VAST trails for winter recreation, this is a true four-season retreat. Visit the Okemo real estate today. Taxes are based on the current town assessment.

955 Smokeshire Rd, Chester
$875,000
4 Beds ⋅ 3 Baths ⋅ 5097711 MLS
50K PRICE CUT! OPEN HOUSE | 11AM to 1PM | Sunday, July 26th, 2026 Welcome to 88 Crawford Road, a breathtaking residential haven nestled in the heart of Chester, New Hampshire. The Property This exquisite colonial estate seamlessly blends sophisticated architectural design with the tranquil beauty of its lush, private surroundings. Offering an expansive 3,675 square feet of meticulously crafted living space, the residence features 4 generously appointed bedrooms and 2.5 elegant bathrooms. From the grand, winding driveway to the majestic facade framed by mature trees, every detail of this home exudes luxury. The interior promises unparalleled comfort with expansive room layouts, high-end finishes, and an abundance of natural light pouring through magnificent feature windows. Location & Drivability Perfectly situated for those who demand both privacy and convenience, 88 Crawford Road offers an idyllic retreat without sacrificing accessibility. Located in the charming, historic town of Chester, you are mere minutes from top-rated local schools, pristine parks, and boutique community dining. For commuters, the property provides seamless access to major regional routes, putting the bustling commercial hubs of Manchester and Salem within easy driving distance, while offering a straightforward, scenic commute to downtown Boston and the gorgeous New Hampshire seacoast.

88 Crawford Rd, Chester
$249,500
4 Beds ⋅ 3 Baths ⋅ 5097620 MLS
Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits. The home is currently configured as two charming apartments, each showcasing timeless character with features such as stained-glass windows, soaring ceilings, and abundant natural light. The first-floor apartment boasts a beautiful brick fireplace with a classic hearth in the kitchen and opens directly onto a private patio, creating a warm and inviting living space. The impressive barn includes a heated workshop area, making it ideal for artisans, contractors, mechanics, or anyone needing year-round workspace. Whether you're looking to establish a small business, expand your existing operation, or simply enjoy the flexibility of extensive storage and workspace, this property offers endless possibilities. Conveniently located on Route 103 between Chester, Springfield, and Ludlow, the property provides excellent visibility, easy access, and ample parking for customers, clients, and guests.

3668 Vt Route 103 N, Chester
$789,000
5 Beds ⋅ 3 Baths ⋅ 5097600 MLS
Exceptional design, enduring craftsmanship, and an unrivaled Vermont setting define this remarkable custom residence on 11± beautifully landscaped acres just a short stroll from the village of Chester. Offering more than 3,600 square feet of thoughtfully designed living space, the home was built to an exacting standard where quality materials, timeless architecture, and exceptional attention to detail create a residence as enduring as it is beautiful. A flexible floor plan offers five bedrooms and three baths, including an elegant first-floor primary suite with ensuite bath, complemented by additional main-level bedroom options ideal for guests, multi-generational living, or a dedicated home office. Upstairs, two spacious bedrooms each feature adjoining bonus rooms perfectly suited as executive offices, dressing rooms, studios, or generous walk-in closets, while additional unfinished space presents exciting opportunities for future expansion. Designed for effortless entertaining and comfortable everyday living, the heart of the home is an open-concept kitchen, dining, and living area filled with natural light. A handsome library offers a quiet retreat, while integrated whole-home audio enhances the experience throughout. An oversized laundry and mudroom connects seamlessly to the attached two-car garage, delivering exceptional convenience without compromising design. Outside, mature gardens, specimen trees, and thoughtfully curated outdoor living spaces create a setting of remarkable beauty and privacy. Relax beneath the covered porch, entertain with family and friends, or simply enjoy the peaceful surroundings. Ideally located just minutes from Okemo, Stratton, Magic, and endless four-season recreation, yet within walking distance of Chester's vibrant village, this exceptional property offers a rare combination of privacy, convenience, and refined Vermont living. A home of lasting quality, exceptional versatility, and unmistakable character!

223 Coach Rd, Chester
$599,000
4 Beds ⋅ 2 Baths ⋅ 5096954 MLS
DON'T MISS THIS RARE OPPORTUNITY! One level living / Multigenerational opportunity. Discover this hard-to-find Ranch-style home set on two beautiful, level acres with exceptional backyard privacy in the heart of Chester's highly sought-after equestrian community. Properties like this don't come along often! This spacious 4-bedroom, 2-bath home offers desirable southern exposure across the backyard, creating the perfect setting to relax on the deck or porch while enjoying stunning sunsets. Inside, you'll find a large living room featuring a classic brick-hearth wood-burning fireplace and expansive hardwood floors that add warmth and timeless appeal. The main level includes three generously sized bedrooms with hardwood flooring, a full bath, and the convenience of first-floor laundry. The kitchen is well-appointed with stainless steel appliances, granite countertops, two pantry cabinets, and stylish recessed and pendant lighting. A bonus family room leads to the attached two-car garage, while the private primary suite above the garage features a sitting area, creating the perfect retreat at the end of the day. The full basement offers excellent potential for additional finished living space, giving you room to grow. Outside, the expansive level lot provides endless possibilities for entertaining, gardening, or enjoying the peaceful surroundings. The pool will require a new liner and possibly a new filter. ENTS & BUYERS to do their own Due Diligence to verify all listing information. Room sizes are for reference only; not guaranteed.

224 Haverhill Rd, Chester
$510,000
3 Beds ⋅ 2 Baths ⋅ 5096706 MLS
STAY-CATION LIVING IS CALLING. Nestled on a gorgeous, private, flat acre in Chester, this home delivers the outdoor lifestyle you've been dreaming of. Pull into the paved driveway and you'll already see it - the lush landscaping, the natural shade, and a backyard that's pure paradise. Three sheds plus a detached garage with partially finished bonus space give you room for all your gear and then some. Step inside through the foyer and you're greeted by warm wood floors and natural light throughout. The open concept kitchen features an island, updated cabinets, and a gas range - ideal for cooking after a long day outside. It opens to a cozy family room with a wood fireplace, one of TWO fireplaces in the home. Heat with propane, wood or electric baseboard. The half bath and laundry are conveniently tucked on the main level. Upstairs, the living room and dining area offer flexible everyday space, and the top floor holds the primary suite with a walk-in closet, a second bedroom with its own large closet, and a completely renovated full bath for both bedrooms to share. The middle floor is designed for a three-bedroom configuration — easy to convert back. Now for the MAIN EVENT: the backyard. Above-ground pool. Hot tub. Garden space. Deck. This is where summers happen. NEW SEPTIC & LEACH FIELD and 2-year-old heating system mean the big-ticket items are already done. Pinkerton Academy district. Book your tour today!

111 Shepard Home Rd, Chester
$825,000
3 Beds ⋅ 3 Baths ⋅ 5096334 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 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. 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 charming community of 8 detached condos in desirable Chester, NH has to offer. Last lot left - do not miss out! Home should be ready late Summer/early Fall.

Lot 2 Lot 2 Robin Way Unit 2, Chester
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