Chester Real Estate

Welcome to Chester, a charming city steeped in history and vibrancy, nestled in the heart of Cheshire, England. Known for its stunning medieval architecture and picturesque riverside views, Chester is a delightful blend of the old and the new, making it a perfect place to call home.

One of Chester’s most striking features is its well-preserved Roman walls, which encircle the city and offer breathtaking views of the surrounding area. A leisurely stroll along these ancient fortifications provides a unique perspective on the city’s rich heritage. The iconic Chester Cathedral, with its stunning Gothic architecture, serves as a cultural hub, hosting various events and exhibitions throughout the year.

The city is also famous for its unique shopping experience. The Rows, a series of two-tiered shopping galleries, boasts an eclectic mix of independent boutiques, high-street brands, and delightful cafes, perfect for a relaxing afternoon. For those who enjoy the outdoors, the picturesque Chester Zoo and the beautiful Grosvenor Park provide ample opportunities for family fun and recreation.

Chester is well-connected, with excellent transport links to major cities like Liverpool and Manchester, making it an ideal base for commuters. The city’s vibrant dining scene features everything from traditional pubs to gourmet restaurants, ensuring there’s something to satisfy every palate.

Whether you’re seeking a bustling urban lifestyle or a peaceful retreat, Chester offers a unique blend of history, culture, and modern convenience. Discover the charm of Chester, where every street tells a story and every corner holds a new adventure. Embrace the opportunity to make this enchanting city your home!

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

$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

$40,000

73563694 MLS

10-Acre Land OpportunityBring your vision to this beautiful 10-acre parcel of land and imagine what could be created here. The sellers once had grand plans for this property, but life has changed, creating an exciting opportunity for someone else to bring those plans to life.The property offers the potential to recreate what was once here, with building limited to the footprint/use of the former structure. A well and septic system will be required. Buyers are encouraged to conduct their own due diligence with the town regarding building, septic, well, permits, and allowable uses.Bring your design. Bring your vision. Bring your dreams. This could be the opportunity to create something truly your own on 10 acres of land.

50 Smith, Chester

$245,000

2 Beds ⋅ 1 Baths ⋅ 73562806 MLS

Absolutely charming and lovingly maintained home across the road from Walker Brook! Enjoy the tranquil sounds of the running water, cool off on a hot summer day or cast out a line and enjoy a vacation right at home. Relaxing wrap around deck to enjoy your peaceful surroundings and seasonal views. An amazing sun room that provides for more space to take in the nature around you, even from inside! The living room with hardwood floors and a gas stove for cozy winter nights offers a large bow window to let in the natural light. The kitchen is bright and spacious with cathedral ceilings and a dining area. Convenient first floor laundry off the kitchen too. Good size bedrooms! The main bedroom has 2 closets, sliders to the wrap around deck and sunroom. This truly special home is move in ready. Garage area, two storage sheds, garden beds and nicely landscaped. This one has it all, for year round or vacation living! Great location! An easy drive to the Berkshires and Northampton. Close to all the great local amenities, historic town center, Chester Theater and never ending popular recreational spots all through-out the hilltowns! Call today.

28 Hampden St, Chester

$100,000

2 Beds ⋅ 2 Baths ⋅ 73561688 MLS

Investors take note of the potential offered by this charming colonial home. Property is being sold as-is. The seller prefers a 60-day closing to allow sufficient time for removal of personal items from the house, yard, and barn. Title V has failed and will be the buyer’s responsibility. The home features partially updated plumbing and electrical systems, including an electrical panel and hot water tank installed approximately three years ago.

166 Route 20, 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

$449,000

2 Beds ⋅ 2 Baths ⋅ 5103536 MLS

** New Siding Being Installed ** 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. Association covers the roof, deck and siding. 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

$739,900

3 Beds ⋅ 3 Baths ⋅ 5102111 MLS

New Construction Without the Wait! Recently completed and loaded with premium upgrades, this beautifully appointed detached condominium offers modern design, quality craftsmanship, and low-maintenance living. Welcome to Pulpit Estates, an exclusive, non-age-restricted and pet friendly community of just eight detached condominiums set on 16 picturesque acres in desirable Chester, NH. The sought-after Osprey floor plan offers the ease of FIRST FLOOR living with a spacious PRIMARY SUITE on the main level, while the second floor features two generously sized bedrooms and a full bath - ideal for family, guests, or a home office. Designed for today's lifestyle, the open-concept living, dining, and kitchen area is anchored by a gas fireplace and showcases numerous builder upgrades throughout. The custom kitchen features Wolf Grantley recessed-panel shaker cabinetry with soft-close drawers, a tall pantry cabinet, 30-inch upper cabinets with crown molding, a 60-inch center island with seating, granite countertops, recessed lighting and Frigidaire Galley stainless steel appliances, including a gas range. Quality finishes continue throughout with 3¼-inch red oak flooring finished in upgraded Bona Traffic HD satin throughout the main living areas and primary bedroom, while all baths feature elegant 12" x 24" staggered brick-pattern tile. Central air conditioning, a whole-house water filtration system, upgraded lighting, and thoughtful designer selections complete the home. Need additional space? The daylight walk-out lower level offers outstanding potential for future finished living space, a home gym, recreation room, or media area. Enjoy all the benefits of brand-new construction - without the delays, decisions, or surprises of building. 3 beds, 2.5 baths and 2 car garage. Lawn to be seeded/virtual grass. Conveniently located in the charming town of Chester with easy access to shopping, dining, major commuter routes, and the highly regarded Pinkerton Academy school district.

8 Robin Way Unit 7, 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

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board logo Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .