Chester Real Estate

Chester Real Estate

Chester, a historic gem nestled in the heart of Cheshire, England, is a city that effortlessly blends rich heritage with modern living. Known for its stunning medieval architecture, Chester boasts an impressive array of attractions, including the iconic Chester Cathedral and the ancient Roman walls that encircle the city. Strolling through its cobbled streets, visitors and residents alike can explore the unique two-tiered shopping galleries known as the Rows, offering a delightful mix of high-end boutiques, charming cafes, and local artisans.

Beyond its picturesque streets, Chester is also home to vibrant green spaces, such as Grosvenor Park, providing a serene escape from the hustle and bustle of city life. The River Dee flows gracefully through the city, offering opportunities for leisurely boat trips and riverside picnics, making it an ideal spot for families and nature enthusiasts.

Chester is not just about its past; it is a thriving community with a diverse population and a strong sense of belonging. The city is well-connected, with excellent transport links to major cities like Manchester and Liverpool, making it a perfect location for commuters. Additionally, Chester's educational institutions, including the University of Chester, offer a range of courses and contribute to the vibrant, youthful atmosphere.

With its rich history, cultural offerings, and a welcoming community, Chester is a charming place to call home. Whether you're looking to settle down in a quaint cottage or a modern apartment, Chester has something for everyone, making it a desirable destination for both residents and visitors alike.

Newest Listings in 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
$610,000
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
$529,500
3 Beds ⋅ 2 Baths ⋅ 5104064 MLS
20K Price Improvement on this 3 bedroom/2 bath raised ranch has had lots of recent updates - exterior painted, new windows, new roof, new gutters, new water heater, new high-efficiency Viessmann boiler, new baseboards, recently paved horseshoe driveway, new pool liner (replaced in 2025). The living room has a cozy woodstove, an eat-in kitchen, a dining room, and a huge family room with dual sliders opening onto your multi-level deck. The recently updated main bath has a washer/dryer hookup. The lower level is finished and could make a great home office, gym, recreation space, in-law or guest bedroom. The lower level bath has been updated and includes a washer/dryer hookup. The spacious yard is level with mature landscaping. As you make memories around the fire pit and in splash the above-ground pool, you'll feel like you're on vacation every day! The workshop area provides space for hobbies or a great place to put your bike. Both sheds have ramps providing easy access to for your lawn tractor, ATV or pool toys. Located on a rural scenic road which is town-maintained, This house is a great commuter location, as North Chester is just a few miles from the highway. The town of Chester offers a quaint New England feel. Like fishing, Norton Pond is just down the road and the Wason Pond Recreation Area has hiking trails and a beach. School-aged children attend Chester Academy and Pinkerton Academy, which are highly sought-after schools. Offers to be submitted with a copy of financial proof of funds/pre-approval letter. Property being sold "As Is"

25 Shattigee Rd, 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
$459,000
2 Beds ⋅ 2 Baths ⋅ 5103536 MLS
Welcome home to the Villages at Chester, a private, well maintained condominium community in a quiet country setting surrounded by an abundance of trees and ponds. Luxury Meets Effortless Living in Chester! Discover the perfect blend of sophisticated style, carefree condominium living, and a peaceful country setting. Enjoy a sparkling pool and clubhouse, all while coming home to this truly move-in-ready residence. From the moment you step through the front door, you'll appreciate the exceptional care and quality throughout. Beautifully refinished bamboo wood flooring, recently replaced Andersen windows ($30k value), and tasteful updates create an inviting, light-filled atmosphere. The elegant kitchen is designed to impress with rich natural wood cabinetry, gleaming granite countertops, a breakfast bar, and abundant workspace for both everyday living and entertaining. Host memorable gatherings in the spacious dining room, then relax in the warm and welcoming living room featuring a cozy fireplace. A convenient mudroom and stylish powder room are located just off the attached garage. Upstairs, you'll find two generously sized bedrooms and a beautifully appointed full bath with a double vanity. The primary bedroom offers a spacious walk-in closet with floor-to-ceiling custom California Closet style cabinetry upgrade, providing exceptional storage. Custom window blinds throughout the home are also included. The finished lower level expands your living space with abundant natural light, offering endless possibilities for a family room, home office, fitness area, or guest retreat. Sliding glass doors lead directly to a peaceful garden setting, creating the perfect indoor-outdoor connection. Energy efficient tankless water heater. AGENTS & BUYERS to do their own Due Diligence to verify all listing information. Room sizes are for reference only; not guaranteed.

25 Villager Road Unit 25, Chester
$149,000
5102503 MLS
Discover the perfect setting for your Vermont dream home or future development on this picturesque rural parcel. Set along scenic Trebo Road, a quiet country road lined with historic homes, open fields, and mature woodlands, this nearly 18-acre property offers exceptional potential. Highlights include approximately 1,500 feet of road frontage, a charming pond, beautiful stone walls, and a Vermont Wastewater Permit for a five-bedroom residence. With zoning requiring a minimum of three acres and 200 feet of road frontage, the property presents an excellent opportunity for subdivision. One building site has already been identified as suitable, while the extensive road frontage provides the flexibility to explore additional potential home sites. A rare opportunity to create a private estate, family compound, or thoughtfully planned development in a quintessential Vermont setting. The location makes it easy to participate in all of the Chester Community events. Just a short drive to Okemo Mountain Resort for all of your outdoor adventures.

Trebo Rd, Chester
$354,000
2 Beds ⋅ 1 Baths ⋅ 5102316 MLS
If you're looking for your forever home or the perfect mountain getaway, take a peek at this locally built Green Mountain Log Home. Davidson Hill Road is home to many craftsman quality homes perched above Chester, overlooking Mt. Ascutney. The open concept first floor spills out onto the generous front deck, essentially doubling the first floor area to roam. Two nearly identical wooden clad bedrooms make up the second floor. The home has a new roof, new on-demand hot water system, fresh stain on the log exterior, updated electrical, and brand new LVL carrying beam and floor joists in the basement. Many other practical upgrades and extensive landscaping has been made and this home is in mint condition. The sellers recently did a drinking water test, had the septic pumped, and did a home inspection, leaving no stone unturned. The 11 acre parcel transitions from a large sunny open yard to old stone walls and hemlock-hardwood forest and rises nearly to the humble summit of Davidson Hill (1053' elevation). The owners let a neighboring property tap most of the maple trees in exchange for maple syrup. The house is located just feet from Trail #5 of the Hawks Mountain Ridge Riders VAST trail network, and is minutes from downtown Springfield and Chester. Just 15 minutes from I-91 and Okemo. While surrounded by forest and situated for optimum privacy, this home does have seasonal views of Mt. Ascutney and there is a good possibility of spectacular views higher up on the property. The height of the property would make an awesome camping or gazebo spot. Many logging roads and four wheeler trails throughout the property. The dog on the couch does not convey.

302 Davidson Hill Rd, Chester
$250,000
5102143 MLS
Nestled on 10 private acres between the towns of Chester and Springfield Vermont, this property offers an exceptional opportunity to build your dream home in a peaceful country setting. A driveway has already been installed, providing easy access to the center of the property where several potential homesites offer the possibility of beautiful mountain and valley views with selective clearing. An existing trailer on the property provides a convenient place to live or use as a base while planning and constructing your new home. With a blend of privacy, natural beauty, and existing improvements, this property is ready for you to bring your vision to life while remaining just minutes from shopping, dining, and year-round outdoor recreation. Selling as-is and needing at least 60 days to close. Also listed under MLS #5102142.

3781 Flamstead Rd, Chester
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