Chester CT Real Estate & Homes for Sale

28 Properties Found

The median home value in Chester, CT is $279,500. This is higher than the county median home value of $248,700. The national median home value is $177,414. The average price of homes sold in Chester, CT is $279,500. Approximately 79.41% of Chester homes are owned, compared to 16.41% rented, while 4.19% are vacant. Chester real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Chester real estate agent to arrange a tour today!
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$267,750

17 Ridge Rd Chester, CT 06412

Open House:

Saturday, 12/10 12:00-3:00PM

Beds:
3
Baths:
2.00
Sq.Ft.:
1,344
Status:
NEW LISTING
MLS#:
N10185347
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
0.22 Acres
Year built:
1951
Courtesy: Berkshire Hathaway NE Prop.
View additional info

Small town charm of Chester Village!! Adorable updated Cape with sparkling hardwood floors throughout. Master Bedroom on the first floor. Open floor plan where the living room flows into the remodeled kitchen with granite counters and stainless appliances. Possible 4th bedroom on the first floor currently being used as a Nursery/Laundry Room. Level corner lot. 1-car garage. Oil heat. Explore downtown lined with galleries, shops, theater and restaurants. Chester elementary school next door. Convenient to Route 9 for commuting.

$349,900

51 Straits Rd Chester, CT 06412

Beds:
3
Baths:
3.00
Sq.Ft.:
1,953
Status:
NEW LISTING
MLS#:
N10185294
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
1.75 Acres
Year built:
1986
Courtesy: Coldwell Banker Res Brokerage
View additional info

Warm and inviting this cape style home is situated privately, yet is walking distance to downtown Chester Village. As you enter the driveway there is a picturesque pond, great for skating parties or summer bonfires. Once closer to the home notice the lovely landscaping which includes a new blue stone terrace which overlooks the property. Once inside the home has a remodeled eatin kitchen complete with a large pantry for storage. The kitchen opens to the family room which is cozy with a wood burning fireplace, and a slider leads you out to a deck which overlooks the back yard. The powder room on the first floor has been remodeled impeccably. Upstairs the master suite is very roomy with a full bath and dressing area. Two additional bedrooms and a full sized guest bath complete the upstairs.

$244,000

2 Butter Jones Rd Chester, CT 06412

Beds:
2
Baths:
2.00
Sq.Ft.:
1,392
Status:
Active
MLS#:
N10182312
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
2.21 Acres
Year built:
1978
Courtesy: BerkshireHathawayNEProperties
View additional info

An architectural charmer offers a private country escape nestled between hundreds of acres of state forest land, pristine lakes, and historic Chester village. Easy to maintain open floor plan with vaulted interior, galley style kitchen, functional and flexible living spaces. Two spacious bedrooms and a full bath on the second floor offer a quite and comfortable nights rest. The great room features a stunning European stone hearth with a one of a kind cast iron insert designed to heat the entire house if desired, with either wood or coal. Enjoy an enclosed porch and covered southern exposure patio. A whimsical "Coop" design barn features a large garage, ample work shop area, and the hayloft provides exceptional storage. Over two acres of privacy set off a dead end street, but easy access to Rt. 148 and Rt. 9. Level, open areas with full sun exposure would support the most ambitious garden bordered by mature fruit trees. This property has had a recent inspection and septic upgrade. A solid and well constructed home.

$119,000

62 Bokum Rd Chester, CT 06412

Beds:
3
Baths:
1.00
Sq.Ft.:
1,272
Status:
Active
MLS#:
N10181037
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
1.28 Acres
Year built:
1950
Courtesy: Coldwell Banker Residential Br
View additional info

Great opportunity for affordable home ownership in one of the areas most desirable towns. This home does need work but well worth it you can own for less than the cost of renting. The house is near Rt. 9 so please check the overhead view before scheduling a showing. Nice open lot with potential for many uses including play space, gardening and recreation. Great 203K loan opportunity.

$439,900

5 Pine Knls Chester, CT 06412

Beds:
6
Baths:
4.00
Sq.Ft.:
3,612
Status:
Active
MLS#:
G10178025
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
2.76 Acres
Year built:
1994
Courtesy: Property Works Connecticut
View additional info

NOTHING TO DO BUT, MOVE IN. EXCELLENT HOME WITH AMAZING VIEWS.6 BEDROOMS,4 FULL BATHS, NEW KITCHEN CABINETS,GRANITE COUNTERS,SUBWAY TILED BACK SPLASH,STAINLESS STEEL APPLIANCES,REFINISHED HARDWOOD FLOORS THROUGH OUT,FRESHLY PAINTED,FIREPLACE,TILED BATHS,CENTREAL AIR,LAUNDRY ROOM,2 CAR GARAGE,DECK AND FIRE PIT.

$279,000

2 Pratt St Chester, CT 06412

Beds:
3
Baths:
2.00
Sq.Ft.:
1,320
Status:
Active
MLS#:
N10179492
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
0.27 Acres
Year built:
1902
Courtesy: Reyher Real Estate
View additional info

Cute adorable home in Chester, not to be missed shows very well. Finished attic, enclosed front porch, 2nd floor porch too. Walk to downtown shops & cafe's.

$359,000

6 Sypher Rd Chester, CT 06412

Beds:
3
Baths:
2.00
Sq.Ft.:
2,994
Status:
Active
MLS#:
G10173615
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
2.16 Acres
Year built:
1974
Courtesy: William Raveis Real Estate
View additional info

Spacious ranch home offers an open floor plan, updated kitchen, hardwood floors, updated baths. There is a nice master with a full bath and walk in closet. The Laundry is on the main level. The family room has a fieldstone corner fireplace and there is a screened in porch. The lower level has heat and a recreation room as well as an office. Workshop space and utility area is off the rec room. Outside you will find a wonderful gardeners shed, an in ground pool with a stunning stone wall, a Post and Beam 2 stall barn with 12x12 stalls, tack room, tractor bay, hot water and a hay loft that will hold approx. 600 bales of hay. There are 2 large paddocks for your horses. One is grass and the other is treed and mostly dirt with a small grass area. Trails are endless. Just a few steps off the property are two different trailhead to the Cockaponsett State forests. Top it off with an attached 2 car garage and you have a great Chester property.

$319,000

51 Castle View Dr Chester, CT 06412

Beds:
2
Baths:
2.00
Sq.Ft.:
1,304
Status:
Active
MLS#:
N10175348
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
0.55 Acres
Year built:
1980
Courtesy: Coldwell Banker Residential Br
View additional info

One floor living at it's best only minutes from Chester Village! This brand new ranch has an open floor plan, cathedral ceilings and attached two car garage and is a great low maintenance offering at a reasonable price. This house has been lovingly taken down to the foundation and completely re-framed, modernized and updated to suit the needs of today's buyer. Bamboo and Italian tile floors, granite counters in kitchen and cultured marble in baths, shaker style raised panel doors and higher quality trim throughout. This home has taken into account the energy efficient desires of today's buyer and offers a very low maintenance life style. Professional landscaping and a private yard makes this the ultimate retreat minutes from the village, route 9 and the Connecticut River. Room dimensions are approximate and the Kitchen, Living Room area is one large open area with a cathedral ceiling. Oversized 2 car garage offers convenient storage option.

$489,000

17 Kings Hwy Chester, CT 06412

Beds:
4
Baths:
3.00
Sq.Ft.:
2,428
Status:
Active
MLS#:
N10173268
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
2.52 Acres
Year built:
1988
Courtesy: William Pitt Sotheby's Int'l
View additional info

CHARM, LOCATION, MOVE-IN CONDITION. This fully updated contemporary is a nature lover's dream. Perched atop a hill in the middle of the woods, it is less than one mile from Chester town center. Floor to ceiling windows and sliding glass doors open to a wrap around deck that looks out onto the woods in summer and Gillette Castle in winter. The updated kitchen with Bosch/Sub Zero appliances features a unique brick hearth around the oven and stove giving the airy, light filled great room a feeling of warmth and comfort. A private stone patio with built in grill and professional landscaping offers outdoor summer living and entertainment at its best. Master bedroom suite with large windows, just up 1/2 flight of stairs from main level. On the ground level there is a mini spa with bamboo floors, new exercise equipment and an infrared sauna. Freshly painted interior throughout. All new carpeting in the bedrooms and office. Beautiful hardwood floors. This home will take your breath away.

$179,900

62 Cedar Lake Rd Chester, CT 06412

Beds:
3
Baths:
1.00
Sq.Ft.:
944
Status:
Active
MLS#:
N10172600
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
0.67 Acres
Year built:
1920
Courtesy: REMAX Valley Shore Genovali Realty
View additional info

Cute as a button! Just steps from Cedar Lake, this 2 bedroom cape on a nice lot has a newer kitchen and bathroom, as well as hardwood floors throughout the rest of the downstairs. The property abuts a brook with access to the lake, perfect for those who love water activities. Needs a little TLC.

$895,000

16 Waterhouse Ln Chester, CT 06412

Beds:
4
Baths:
5.00
Sq.Ft.:
4,661
Status:
Active
MLS#:
N10162687
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
2.78 Acres
Year built:
1988
Courtesy: Page Taft - Christie's IRE
View additional info

Walk to Chester Village from this privately situated stately home. Beautiful lush landscaping with perennials and specimen plantings, in ground heated Gunite pool with refined stone terrace, 3-car detached barn/garage, and refined stone covered walkways leading to this sunlight filled home with all luxury amenities. The gourmet kitchen boasts 2 islands and built in banquette seating as well as a large walk in pantry. The living room sports a two story granite fireplace and the master suite optimizes luxury from it's private exercise room to glass enclosed seating area overlooking the grounds and the hills beyond, to the newly remodeled master bath featuring Ming green marble. This home is in pristine condition and very timeless in it's styling. Move right in!

$495,000

80 West Main Chester, CT 06412

Beds:
3
Baths:
2.00
Sq.Ft.:
2,389
Status:
Active
MLS#:
N10162412
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
1.4 Acres
Year built:
1835
Courtesy: Berkshire Hathaway NE Prop.
View additional info

Great location in Chester-close to town center. This 1835 built Federal home has a lot to offer including a fully updated kitchen with Viking Stove, new Bosch dishwasher, SubZero Refrigerator, large island, and beautiful granite counters. The charm of an antique with quality updates and additions including an artists studio/bonus room with loads of light and beautiful windows. 3 fireplaces, plus a wood stove and a whole house GENERATOR! A new architectural asphalt roof was just installed on the main home. Two adjacent buildings are close to the main home. One is a large Artist Studio/Workshop that could be used for many purposes with its high ceiling and separated office space. The other outbuilding is perfect for an office or small studio. The home, location, and separate outbuildings are truly special. Don't wait to see for yourself!

$590,000

16 Gilbert Hill Rd Chester, CT 06412

Beds:
4
Baths:
3.00
Sq.Ft.:
2,648
Status:
Active
MLS#:
N10159086
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
1.01 Acres
Year built:
2004
Courtesy: William Raveis Real Estate
View additional info

Do you love traditional colonial homes but want an open floorplan? Look no further! High ceilings and expansive windows throughout bring in natural sunlight from morning to evening. The living room, dining room, and kitchen area open to each other creating a wonderful flow. Enjoy the salt water heated pool and the many outside entertaining spaces. The placement of the home gives you ample privacy and you are very close to the lovely downtown Chester shops and restaurants.

$499,000

15 Gilbert Hill Rd Chester, CT 06412

Beds:
4
Baths:
3.00
Sq.Ft.:
2,924
Status:
Active
MLS#:
N10157924
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
1.44 Acres
Year built:
1950
Courtesy: REMAX Valley Shore Genovali Realty
View additional info

Gorgeous Cape on Hilltop setting overlooking the Connecticut River Valley. Generous windows bring in the light and the view! Huge master suite with master bath, twin walk-in closets and a screened balcony overlooking the grounds with distant views of the river. Recent updates include a new granite kitchen, mahogany deck, and a high efficiency propane heating system. Additional features include a 3 car attached heated garage, and a detached barn with kitchen, full bath, and game room - great for in-law potential or a studio. Irrigated, beautiful grounds surround the home, nestled just outside one of the most quaint villages in Connecticut.

$639,900

78 Pinnacle Ln Chester, CT 06412

Beds:
4
Baths:
5.00
Sq.Ft.:
3,542
Status:
Active
MLS#:
P10154694
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
5.69 Acres
Year built:
2005
Courtesy: RE/MAX Edge
View additional info

Spectacular colonial in Chester Forest Estates! Nestled on over 5 private acres. Love entertaining? This is the perfect home. Open floor plan, chefs kitchen with a center island, granite counters, cherry cabinets, stainless steel appliances, double oven and a wolf cook top! Brazilian cherry floors throughout, 2 fireplaces, inviting light filled family room with cathedral ceilings and built-ins. Master bedroom featuring tray ceilings, a gorgeous 14x9 walk-in closet/dressing room and a huge bathroom with double sinks, over sized jetted tub and separate shower. Au pair suite with full bath and separate staircase. Finished 1100 sqft walkout basement leading to a large patio. Hydro air heat, 3 car garage, cul-de-sac street, to many upgrades to list! Come see for yourself the quality of living this beautiful home offers in the quaint town of Chester.

$415,000

21 Baker Rd Chester, CT 06412

Beds:
3
Baths:
3.00
Sq.Ft.:
2,378
Status:
Active
MLS#:
N10151741
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
3.97 Acres
Year built:
1991
Courtesy: Reyher Real Estate
View additional info

Chester very private location near Cockaponset State Forest. Beautiful home with many custom features and luxurious finishes. 3 bedrooms, 2 full & 1 1/2 bath, 1st floor master suite w/ walk-in closet. Spacious open floor plan, custom kitchen with quartz and stainless appliances. 1st floor laundry area. 1000sqf deck for entertaining, w screened dining area. Partially finished basement w/ double door walkout. Large living room w/ fireplace with wood stove insert. Central a/c & central vac, generator hookup. Bay windows and more, come see this turn key home.

$439,900

83 Main St Chester, CT 06412

Beds:
2
Baths:
2.00
Sq.Ft.:
1,677
Status:
Active
MLS#:
N10150748
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
0.38 Acres
Year built:
1920
Courtesy: William Pitt Sotheby's Int'l
View additional info

"Located in the village district", this versatile property lends itself to a residence with commercial or office use, a hard to find combination !! This c 1920 classic Federal style home is loaded with charm and character, has an open floor plan with light filled rooms, remodeled kitchen and baths (2 ), an office and a finished lower level as well as an attached 2 car garage with "ELEVATOR access" to the basement, main floor and upper level!! It boasts a newer roof too ! "WHOLE HOUSE GENERATOR" !!! THIS IS A RARE FIND IN THE VILLAGE ! See MLS # N10150850 also.

$375,000

2 Winthrop Rd Chester, CT 06412

Beds:
4
Baths:
4.00
Sq.Ft.:
3,257
Status:
Active
MLS#:
N10149482
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
1.66 Acres
Year built:
2006
Courtesy: William Pitt Sotheby's Int'l
View additional info

Contemporary Colonial. Dramatic two story foyer. Hardwood with walnut inlay. Eat-in kitchen with island. Formal dining room. In-law/ au pair suite with separate entrance offers fifth bedroom or second master suite option. Energy efficient 3 zone geothermal, electric heat pump forced hot air system w/ active solar. Oil H2O heater. Stroll to Chester Lake. Convenient to Route 9 for commuting.

$775,000

Castle View Dr Chester, CT 06412

Beds:
3
Baths:
3.00
Sq.Ft.:
2,006
Status:
Active
MLS#:
N10140537
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
1.04 Acres
Year built:
1996
Courtesy: William Pitt Sotheby's Int'l
View additional info

Connecticut River waterfront home on a 1 acre lot with a private deep water dock and a deck right at the water's edge! Captivating custom contemporary with an open floor plan, soaring ceilings in the living/dining room with walls of glass, and an open and bright kitchen with brand new stainless appliances. Other striking features include a 2 story stone fireplace, a covered porch, and decks off of the living/dining room and the master bedroom. The 3 bedroom, 2 1/2 bath home is a one of a kind design with unique iron work, and the manicured grounds have an abundance of decorative grasses, hydrangeas and specimen trees. Located in a quiet four home enclave with amazing views looking up and down river. Just a short drive to Chester Village with it's fine restaurants, galleries & shops.

$845,000

44 Spring St Chester, CT 06412

Beds:
3
Baths:
5.00
Sq.Ft.:
3,841
Status:
Active
MLS#:
N10122653
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
1.91 Acres
Year built:
1996
Courtesy: William Pitt Sotheby's Int'l
View additional info

Presenting a classic shingle-style colonial with over 600 feet of frontage on Jennings Pond. Adjacent to a protected conservation area. Enjoy the peacefulness of Jennings Pond and the sound of a rushing brook that borders the property. The setting is serene and the spacious house is like-new and offers every amenity for comfortable waterfront living. Open floor plan kitchen/great room with breakfast area leads to a gracious living room with fireplace, formal dining room, family room and both an enclosed porch overlooking the pond and a deck conveniently located off the kitchen - perfect spot for a grill. Three bedrooms upstairs, each with full bath, one with a fireplace and a master suite with generous walk-in closet. There is also a cedar closet and laundry room on this level. Fully finished walk-out lower level family room with huge fireplace and kitchenette adds another 1,200 SF of living space. Every room has a view. A bench by the pond offers the ideal place to contemplate nature. The gently sloping lawn leads to water's edge, where there is easy kayak, canoe and SUP access. A lovely restored red barn provides great storage. Just minutes to quaint Chester village shops, galleries, restaurants and CT river marinas and yacht clubs. Two hours from NYC and Boston. With easy village access and the ability to enjoy an active waterfront lifestyle, enjoy the best of two worlds!

$375,000

15 Maple St Chester, CT 06412

Beds:
4
Baths:
2.00
Sq.Ft.:
1,881
Status:
Active
MLS#:
G10120396
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
0.22 Acres
Year built:
1902
Courtesy: Coldwell Banker Res Brokerage
View additional info

A unique opportunity to own a beautifully appointed 1902 Colonial in historic Chester Village. Steps from exceptional eateries, historic pub, shopping and the Farmers Market held in the village square Sunday's June-October. The home has been remodeled to an open floor plan, remodeled baths and newly finished third floor bonus room. Enjoy relaxing on the charming covered front porch or the slate patio in the quiet backyard. Fire pit, walk out basement and electrified shed are a bonus. Backyard abutts town parking for your quests parking convenience.

$339,900

75 West Main St Chester, CT 06412

Beds:
3
Baths:
3.00
Sq.Ft.:
1,704
Status:
Active
MLS#:
N10118049
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
0.78 Acres
Year built:
1825
Courtesy: William Pitt Sotheby's Int'l
View additional info

SO SPECIAL!! This village home is set on a beautiful spacious lot that slopes down to a restful creek. A must see with kitchen that has beamed cathedral ceiling with skylights, ceiling fan, granite counter tops and large window to enjoy the lovely back yard. The sun room has wrap around windows, skylights, stone floor, propane stove to keep you toasty warm during cool weather. The dining room is comfortably adjacent to kitchen and sun room. Large and warm L shaped living room/den combination is perfect for entertaining and/or just relaxing. Renovated barn is one more of the many special features on this property. Very close to the center of town to enjoy all it has to offer. Only 2 minutes to Rte 9. An amazing opportunity --- don't miss it!!!

$450,000

12 Winthrop Rd Chester, CT 06412

Beds:
5
Baths:
4.00
Sq.Ft.:
4,117
Status:
Active
MLS#:
N10095660
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
2.17 Acres
Year built:
1985
Courtesy: William Pitt Sotheby's Int'l
View additional info

This is a must see! If you're a member of the sandwich generation, this house is perfect. The freshly painted main house, situated on over 2 acres, started as a Cape and morphed into so much more. The first floor apartment with separate entrance, fireplace, deck and wheelchair accessible bath can be used for in-laws, a live-in nanny, supplemental income, or office for the work from home professional. The main house offers a center staircase dividing the formal living and dining rooms. Behind is the eat-in kitchen which leads to the deck. Just off the kitchen area is the great room/family room/ballroom. Yes, a ballroom! The furniture can be moved aside to create a dance floor. Marble floors, a cathedral ceiling and a fireplace (one of 3) complete the room. Upstairs the master suite has a dressing room as well as a master bath featuring a Jacuzzi tub and steam shower. The three other bedrooms are roomy and all share the second floor laundry. Downstairs is partially finished with space for a media room, fitness center, office and play room. Oh, did I mention there's an oversized three car garage under the house and ample room for parking in the circular driveway. Lovely Cedar Lake is a short walk away.

$1,175,000

134 Pinnacle Ln Chester, CT 06412

Beds:
4
Baths:
6.00
Sq.Ft.:
4,694
Status:
Active
MLS#:
N10093576
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
5.86 Acres
Year built:
2007
Courtesy: William Pitt Sotheby's Int'l
View additional info

Take advantage of the opportunity to own a recently constructed, magnificent shingle-style contemporary set in an enviable location. Privately sited in a quiet neighborhood, this home is just minutes from quaint Chester village. Chester is renowned for it's small-town artsy vibe, first class restaurants, shops and live theatre. Enjoy weekly farmer's markets, annual events like Winter Carnival, stroll nights and gallery openings. This immaculate, move-in ready dream house is also just minutes from charming Essex village on the CT river and a short drive to neighboring beaches on Long Island Sound. Almost equidistant between Hartford/Middletown and New Haven and only two hours to Boston or New York City. Spacious in-law opportunity. Coffered and vaulted ceilings, a massive fieldstone fireplace and a chef's kitchen with Sub-Zero and Wolf appliances and a custom wine cellar, are just some of the amenities you will find here. If you are looking for a new home built with attention to detail in a location offering a unique lifestyle, then come home here!

$588,000

16 North Main St Chester, CT 06412

Beds:
4
Baths:
3.00
Sq.Ft.:
2,737
Status:
Active
MLS#:
N10078523
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
0.44 Acres
Courtesy: William Pitt Sotheby's Int'l
View additional info

The charming village of Chester lies just steps away from the historic Thomas Dunk homestead circa 1672. Meticulously deconstructed by a devoted antiquarian in 1975, this classic Colonial post and beam was insulated, re-sheathed and rebuilt from the original timbers and flooring. Nearly nine foot ceilings, unusual for this era, span the first floor. The 1980's addition of a two car garage includes a charming guest master suite with a separate entrance and balcony. New shake shingle roofing, copper gutters and downspouts grace the exterior of the first home in Chester. The remarkable condition of this well maintained 18th century home bodes well for the next 300 years. Currently home to a colorful local artisan and former chef, the fire-placed kitchen includes professional appliances and is fitted with custom shelving, granite counters, multiple pot racks and book cases in a unique and efficient layout. Family room adjoins. Zoned both residential and commercial a period style 1980's improvement includes a master suite with separate entry suitable for a professional office, rental apartment or for guests, in-laws, visitors, family and friends. Outside, the property is bordered by a gently flowing stream. A charming, private and peaceful rear patio is surrounded by perennial gardens, fruit and dogwood trees. As you walk a block to the village and experience the regions favorite eateries and shops, you may well wonder why it took so long to discover the charm of Chester.

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