Chester Real Estate

Welcome to Chester, a picturesque city steeped in history and charm, located in the heart of Cheshire, England. Renowned for its stunning Roman architecture and vibrant cultural scene, Chester offers a unique blend of the old and the new, making it an ideal place to call home.

As you stroll through the cobbled streets, you'll be captivated by the city's rich heritage, showcased by the well-preserved Roman walls that encircle the city. Don't miss the iconic Chester Cathedral, a masterpiece of medieval architecture that invites visitors to explore its tranquil gardens and stunning interiors. The city is also famous for its unique Rows, a series of two-tiered shopping galleries that house an array of boutiques, cafes, and restaurants, perfect for a leisurely day out.

Chester is not just about history; it boasts a vibrant community and a thriving economy. The city is home to a diverse range of businesses, from independent shops to larger retailers, ensuring a bustling atmosphere. The Chester Market, with its eclectic mix of food stalls and artisan products, is a must-visit for food enthusiasts.

For nature lovers, Chester is surrounded by beautiful countryside, including the stunning Delamere Forest and the scenic River Dee, offering plenty of opportunities for outdoor activities like hiking, cycling, and boating. The city's excellent transport links make it easy to explore the wider Cheshire area and beyond.

Whether you're looking for a charming home in a historic setting or seeking a vibrant community with a wealth of amenities, Chester has something for everyone. Discover the magic of Chester and find your perfect place in this enchanting city!

Newest Listings in Chester

$749,900

3 Beds ⋅ 3 Baths ⋅ 5108579 MLS

First time in 26 years, one of only eight homes on Abenaki Circle is ready for its next chapter. Cared for by the same family since it was built, this distinctive home combines privacy, neighborhood connection, and special spaces, turning everyday moments into warm memories. Walk up onto the farmer's porch and into the home, and the centerpiece of the home greets you: an open-concept kitchen with an extended breakfast bar spills into a warm dining room and oversized great room defined by soaring vaulted ceilings, exposed wood beams, and a striking brick fireplace with custom mantel. Hardwood and tile flooring and natural wood finishes tie all three spaces together, creating the kind of first floor built for both everyday life and holiday gatherings full of stories and laughter. A dedicated home office/den and 1/4 bath with laundry round out this level, adding everyday convenience. Upstairs, the primary suite offers a peaceful retreat with a walk-in closet and ensuite bath, while two additional bedrooms, each with custom closets, share a full bath. The beautifully finished third level, with hardwood floors and exposed beams, extends the home further, providing a versatile bonus room, ideal as an office, playroom, or studio. Step back outside onto the farmer's porch or the expansive two-tiered back deck, framed by mature landscaping, established hydrangeas, and stone hardscaping, creating settings where morning coffee turns into watching deer move quietly through the yard, while hearing birdsong throughout the day. A well-organized custom mudroom, storage shed with firewood lean-to, full irrigation, and two-car garage provide everyday function to make the home easy to live in. Located in the acclaimed Chester Academy and Pinkerton Academy school communities, the home is minutes from Wason Pond with easy access to I-93, Route 101, and Manchester Airport. Lifetimes are built around homes with this type of charm, and rarely come to market in this quiet corner of Chester.

29 Abenaki Cir, Chester

$340,000

5107814 MLS

Exceptional mixed-use opportunity with strong visibility on South Main Street in downtown Chester. This versatile property features two residentialapartments—a 2-bedroom, 1-bath unit and a 1-bedroom, 1-bath unit—alongside two commercial spaces, creating a diverse and stable income stream. A large barn addstremendous upside with the potential for additional units or expanded uses, subject to local approvals. Positioned in the heart of one of Southern Vermont’s mostcharming villages, the property benefits from excellent exposure and convenient access to Chester’s vibrant downtown, local shops, restaurants, and year-round events.Ample parking provides added convenience for residents, customers, and tenants alike. Whether you're looking to expand your portfolio, establish a business presence, orcapitalize on future development potential, this well-located property offers the ideal blend of cash flow, visibility, and long-term opportunity. 3D Virtual Tour availableupon request.

145 S Main St, Chester

$700,000

2 Beds ⋅ 3 Baths ⋅ 5107796 MLS

A wonderful retreat on 35+/- acres in Chester is ready for new owners to enjoy. The gated, serpentine driveway threads its way through the woods and by the large pond, taking in the lovely, open meadow with stone works and gardens leading to the classic custom 2+ bedroom, 3 bath chalet in an absolutely charming setting. As if transported from the Alps, the architectural features, such as handsome exposed wood beams, cathedral ceiling with a large wrought iron chandelier, a dramatic wooden spiral staircase and ceramic tile, all echo elements of style from the slopes of Northern Italy. The current owners have restored and upgraded each of the three full baths with a spa-like sensibility and added cosmetic upgrades to the kitchen and throughout the home. The cozy living room features a woodburning fireplace and as well as a mini split to warm and cool off as needed. The cheerful kitchen with quartz counters and breakfast bar adjoins the dining area. A three-quarter bath with a luxurious tiled shower completes the first floor. The spiral stairway leads to a spacious light filled living/play area with a wood burning fireplace and a balcony to enjoy the stunning view. A third floor loft/aerie makes a wonderful study or play area. A solar array with two Tesla batteries offsets the electric bill and protects the property in a power outage. The two car garage is neatly tucked under the patio that features an inviting hot tub. Out front, the stone patio will delight with its custom granite picnic table and benches- a remarkable conversation piece! There are trails to hike through the woods, frontage along the Williams River for trout fishing, an old stone foundation, and a delightful pond with a floating dock to swim and relax with friends and family, all in a mesmerizing setting within 5 min. to the Chester village. Close to Okemo and several other ski mountains. This unique property would make an awesome vacation or full time home.

1260 Grafton Rd, Chester

$499,000

3 Beds ⋅ 1 Baths ⋅ 5107622 MLS

Wait until you see this charming, light and bright one-level Ranch with direct access to the Exeter River! Enjoy fishing or launching a canoe right from your own backyard, all while being located outside of a flood zone. Tucked away on a private lot in Chester with no neighbors visible on either side, this home offers a peaceful setting surrounded by nature. Inside, you’ll find a light-filled and inviting interior, 2–3 bedrooms, an updated kitchen, a full bathroom, and a basement offering plenty of storage. A cozy wood stove will keep you toasty during those chilly New Hampshire winters. Step outside onto the spacious deck overlooking the river, the perfect place to relax, entertain, or simply take in the beautiful natural surroundings. Outdoor enthusiasts will love the abundant birds and wildlife, fishing, and opportunities for canoeing or boating when water levels allow. A storage shed, additional she-shed, and extra parking add even more versatility. If you’ve been dreaming of a light, bright and peaceful home where you can enjoy the outdoors right from your own backyard, this one is a must-see! Showings start at the open house on Saturday, Sept 5 from 12-2.

56 Shepard Home Rd, Chester

$475,000

3 Beds ⋅ 2 Baths ⋅ 5107281 MLS

Storybook charm meets thoughtful modern updates in the heart of Chester! From the moment you arrive, you'll feel the character and the warmth of or this charming 3 bedroom, 1.5 bath cape. Thoughtfully remodeled through the years, the home has been lovingly updated while preserving the original charm and details that make it feel truly special. The inviting first floor offers a comfortable flow for everyday living, including a first floor primary bedroom and convenient first-floor laundry. Throughout the home, you'll find a wonderful balance of timeless character and practical updates, creating a home that feels both classic and comfortable. And then there's the yard! Level, spacious, and incredibly usable, it provides the perfect backdrop for summer gatherings, lawn games, entertaining, gardening, or simply enjoying a quiet afternoon outdoors. There's room here to make memories. Located in Chester, NH, a town known for its quintessential New England charm this home offers a wonderful sense of community while still being conveniently positioned for commuters. It's the kind of place that feels like home the moment you arrive-and a property you'll be proud to call your own and the perfect place to start your next chapter.

40 Old Sandown Rd, Chester

$1,379,900

4 Beds ⋅ 3 Baths ⋅ 5106863 MLS

OPEN HOUSE, Sat August 29th from 10am to 4pm. Stunning Brand-New Home READY NOW! Over 3.8 acres in Chester, NH showcasing over 3840 sq ft of an eye-catching design inside and out with metal roof accents, board/batten detail, stone veneer, black windows, 3 car garage plus gorgeous curb appeal with landscaping, granite paver walkway with 2 front porches. Inviting you inside to a 2-story foyer, wide plank natural white oak HDWD floors throughout, 9' first floor ceilings, interior transoms, coffered ceilings, solid core craftsman style doors, Baldwin door handles, crown molding, built-in bookcases to name a few... Designer dream mudroom complete with 2 built ins, closet, cabinetry and floating shelves. Top notch kitchen embraces all your senses with natural quartzite counters, CAFE appliances, 36" commercial stove with pot filler, oversized island, subtle yet striking backsplash, butler pantry area with glass cabs and a walk-in pantry. Light filled family room with a stone veneer gas fireplace. Spacious yet private 1st floor office/den with French door entry. Magnificent HDWD staircase makes a statement in this home from the light wood tone, boxed newels and rod iron balusters to the well-appointed 2nd floor. Private primary suite with a comfortable yet expansive space. His and hers oversized light and bright Walk in Closets. The primary bath tile shower with rain head/handheld features, glass enclosure, soaking tub, extra drawers in the double vanity, quartz counters, linen closet and private water closet. Every detail in this home has you in mind. Three roomy secondary bedrooms share a super functional full bathroom with double sinks, private tub shower/toilet room and 2 linen closets. 2nd floor laundry room with quartz counters/cabinets and designer floating shelves. Your private landscaped back yard oasis starts just steps from your impressive granite paver patio/back porch to plan all the best moments and create the best memories. Welcome Home! Agent interest.

109 Crowley Rd, Chester

$615,000

3 Beds ⋅ 2 Baths ⋅ 5106758 MLS

Step back in time without giving up today’s modern comforts in this thoughtfully designed antique replica Cape, beautifully crafted by the renowned Tammy Grimes. Set privately on 2.8 serene acres, this exceptional home captures the character, warmth, and timeless charm of an antique New England home while offering the conveniences and updates today’s buyers desire. Inside, you’ll find beautifully preserved character paired with thoughtful modern improvements. The newly redesigned first-floor bathroom features a stunning tiled shower, while the custom kitchen offers both functionality and distinctive style. Cozy up by the pellet stove or enjoy the comfort of forced hot-air heat throughout the home. A whole-house generator provides added peace of mind in every season. The private, peaceful setting offers plenty of room to relax, entertain, garden, or simply enjoy the tranquility of your surroundings. With its classic Cape architecture, inviting interior, custom details, and modern amenities, this is a truly special property that blends the romance of an antique home with the comfort of contemporary living. A rare opportunity to own a piece of timeless New England charm in a beautiful Chester setting.

15 Ledge Rd, Chester

$599,000

4 Beds ⋅ 2 Baths ⋅ 5106579 MLS

Tucked away on a quiet country road, this well-maintained 4-bedroom Cape home offers the peaceful Vermont setting so many buyers are searching for. Set on 12.86 acres, the property has been a place where generations have gathered, and now it's ready for its next chapter. Thoughtfully updated and meticulously cared for, the home features a new roof along with numerous improvements that provide confidence and convenience for years to come. Inside, the practical floor plan includes a desirable first-floor primary bedroom and first-floor laundry, making everyday living comfortable and accessible. The remaining bedrooms offer flexibility for guests, a home office, hobbies, or creative space. Step outside to enjoy beautifully landscaped grounds, a spacious deck built around an above-ground pool, and the quiet surroundings that define rural Vermont living. Multiple barns and sheds provide exceptional versatility, whether you're looking for a workshop, tractor or recreational vehicle storage, equipment space, or even a former horse stall ready for new possibilities. Combining privacy, usable acreage, and a property that has been lovingly maintained over the years, this home offers the opportunity to enjoy country living without sacrificing comfort. Whether you're looking for room to spread out, space for projects, or simply a peaceful place to call home, this property is ready to welcome its next owners.

548 Crow Hill Rd, Chester

$255,000

3 Beds ⋅ 2 Baths ⋅ 5106226 MLS

Welcome to 159 Lower Bartonsville Road, a charming carriage house nestled along a scenic country farm road in Rockingham, Vermont, just moments from the picturesque restored Bartonsville covered bridge. This 3 bed, 1.5 bath property features authentic 1830s architecture and timeless rustic character, offering a solid structural foundation with much of its original detail preserved. Seamlessly blending old-world appeal with boundless equity-building potential, this quintessential New England abode serves as the perfect canvas for your personal touch. It is entirely ready for cosmetic enhancements, custom modern finishes, and tailored design choices that will allow you to completely personalize the space to match your unique vision. Just 15 minutes from I-91 and Springfield VT, 35 minutes to Keene, NH and 40 minutes to Lebanon NH. Stop on by and see it for yourself!

159 Lower Bartonsville Rd, Chester

$289,900

3 Beds ⋅ 3 Baths ⋅ 5106191 MLS

Extremely well maintained and thoughtfully updated, this spacious three bedroom, two and a half bath home is privately nestled on 2.6 acres on a quiet dead end. Offering the convenience of single level living, the property has been meticulously cared for over the years, with numerous improvements that make it comfortable, efficient, and move in ready. Inside you’ll find generously sized rooms throughout, offering plenty of space for everyday living and entertaining. The home features a primary suite with its own private full bathroom with a soaking tub, two additional good sized bedrooms, another full bath, and a convenient half bath. The functional single level layout makes the home easy to enjoy, while the main living areas offer plenty of natural light and comfortable gathering space. The home has seen an impressive list of recent updates, including new kitchen flooring in 2021, a new roof and skylights in 2022, newer kitchen appliances, and a mini-split system installed in 2023. Additionally, a new hot water heater in 2025. Set on 2.6 acres, the property offers a peaceful and private setting while still providing convenient access to Chester and the surrounding area. With its spacious rooms, primary suite, 2.5 baths, single level living, extensive recent improvements, and exceptionally well-maintained condition, this is a home that has been cared for with attention to detail and is ready for its next owners to enjoy.

3713 Trebo Rd, Chester

$289,000

3 Beds ⋅ 2 Baths ⋅ 5104543 MLS

Antique charm at its best! This vintage beauty dates back to the horse and buggy days, but you'd hardly know it once you step inside. Beautifully done hardware floors, newer windows, custom built hardwood cabinets in the kitchen with loads of storage, modern appliances, and lots of natural light gives you that warm and relaxing feeling. Large first floor living room, dining room and bedroom add to the convenience. The second floor has two more generously sized bedrooms. Additionally, there is an incredible amount of storage in the barn. All this, within walking distance to shopping, restaurants, town hall, and all of the basics you might need in the quintessential town of Chester, Vermont! This house is anxiously awaiting it's next lucky owner.

447 Elm St, Chester

$330,000

4 Beds ⋅ 2 Baths ⋅ 5104013 MLS

***Open House Wednesday August 12th, from 4pm-5:30pm*** Attention Contractors, flippers, and Investors! Great opportunity to build some sweat equity. Single Family with 4 beds 2 baths and 3,734 sqft. This is a property with a TON of potential. SOLD AS IS! Cash or Hard Money ONLY. Sale is contingent upon the seller completing their purchase; seller currently has the property under contract. Seller and seller’s reps. hold a real estate broker or agent license. Some personal items to remain and become the buyer's responsibility.

55 Chester St, Chester

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