Chester Homes for Sale

Welcome to Chester, a historic gem nestled in the heart of Cheshire, England. Renowned for its stunning medieval architecture and vibrant cultural scene, Chester offers a unique blend of history and modern living. Stroll along the ancient city walls, explore the iconic Chester Cathedral, or indulge in a shopping spree at the charming Rows, where you’ll find a mix of high-end boutiques and quaint cafés. The city is also home to picturesque parks and the scenic River Dee, perfect for leisurely walks or family picnics.

When it comes to finding your dream home, Chester has an impressive array of properties for sale that cater to diverse tastes and lifestyles. From elegant Victorian townhouses with period features to contemporary new builds that boast modern amenities, there’s something for everyone in this captivating city. Families will appreciate the spacious homes located in sought-after neighborhoods, while young professionals can find stylish apartments within easy reach of the city center.

Chester’s strong sense of community, excellent schools, and convenient transport links make it an ideal place for families and individuals alike. The city’s rich heritage combined with a thriving local economy ensures that investing in property here is not just a wise choice but a delightful experience.

Explore the homes for sale in Chester today and discover the perfect setting for your next chapter. Whether you’re drawn by the city’s charm or its vibrant lifestyle, Chester awaits to welcome you home!

Newest Chester Homes for Sale

$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

$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

$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. Open House Saturday, August 22 10:00am-12:00pm.

34 Edwards Mill Rd, Chester

$900,000

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

$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

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