Chester CT Real Estate & Homes for Sale

23 Properties Found

The median home value in Chester, CT is $206,000. This is lower 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 $206,000. 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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$269,900

44 Castle View Dr Chester, CT 06412

Beds:
3
Baths:
2.00
Sq.Ft.:
1,445
Status:
NEW LISTING
MLS#:
G10191215
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
0.4 Acres
Year built:
1987
Courtesy: Sovereign Asset Mgmt Realtors
View additional info

Lovely 3 bedroom cape situated on corner lot. Updated kitchen with granite counter tops and stainless appliances. Features 1.5 bathrooms which were recently updated. Oil heat and hot water with central air. 2 car garage. Full unfinished basement. Minutes from route 9 and downtown Chester.

$380,000

17 High St Chester, CT 06412

Beds:
3
Baths:
2.00
Sq.Ft.:
2,880
Status:
Active
MLS#:
N10190024
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
0.41 Acres
Year built:
1986
Courtesy: William Pitt Sotheby's Int'l
View additional info

Stroll to Chester Village from this Greek Revival Colonial. Dramatic two story foyer, 9 foot ceilings, three fireplaces. Large second floor landing with balcony and palladium window offers wonderful space for sitting area, gallery. Newly renovated kitchen with island breakfast bar. Convenient to Route 9 for commuting. Chester is situated in the heart of the scenic Lower Connecticut River Valley and is renowned for its quaint village featuring unique shops, numerous galleries and diverse restaurants. Chester is only two and one half hour away by car to both New York City and Boston as well as an easy commute to Hartford, New Haven and New London. Seller will consider Lease Purchase option. 17 High Street is also available for rent. See MLS listing #N10184003 for rental detail.

$529,000

107 West Main St Chester, CT 06412

Beds:
4
Baths:
2.00
Sq.Ft.:
2,117
Status:
Active
MLS#:
G10189777
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
24.89 Acres
Year built:
1976
Courtesy: William Raveis Real Estate
View additional info

24.89 ACRES! ENCHANTED, WINDING BABBLING PATTACONK BROOK EMBRACING THIS RARE PROPERTY! NESTLED ON A SECLUDED LOT SECONDS FROM RT 9! SOUGHT AFTER 4 BEDROOM BARN STLYE HOME WITH OPEN FLOOR PLAN, EAT IN COUNTRY KITCHEN WITH ANTIQUE BRICK WOOD FIRED OVEN, OVERSIZED LIVING ROOM WITH FIREPLACE, MASTER SUITE WITH WOOD STOVE, WALK OUT BASEMENT, 2 CAR GARAGE WITH LOFT FOR STORAGE, FULLY FLOORED ATTIC, 4 + HEATED GARAGE AND IN-LAW APARTMENT WITH ADDITIONAL 1500 SQUARE FEET OF LIVING SPACE. GORGEOUS VAULTED CEILINGS, SKYLIGHTS AND RECESSSED LIGHTING. APARTMENT WAS BUILT IN 2002 WITH NO NEED TO UPDATE. THIS PROPERTY WOULD BE SUITED FOR MANY DIFFERENT USES.

$199,900

1 Brookside Rd Chester, CT 06412

Beds:
3
Baths:
2.00
Sq.Ft.:
1,410
Status:
Active
MLS#:
N10189201
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
0.49 Acres
Year built:
1970
Courtesy: REMAX Valley Shore Genovali Realty
View additional info

Three bedroom, two bath Ranch on an oversized lot near Cedar Lake. Large, open living room with fireplace, three season sun room off kitchen, one car attached garage. Good condition, could use some updating.

$349,900

51 Straits Rd Chester, CT 06412

Beds:
3
Baths:
3.00
Sq.Ft.:
1,953
Status:
Active
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.

$234,900

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.

$99,000

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.

$267,435

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 turn of the century home in Chester,on a dead end rd. not to be missed shows very well. Finished attic, enclosed front porch, 2nd floor porch too. Short walk to downtown shops, art galleries and a wide variety of wonderful restaurants. Well maintained, turn key property. A must see.

$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.

$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!

$112,000

3 Birch St Chester, CT 06412

Beds:
2
Baths:
1.00
Sq.Ft.:
792
Status:
Active
MLS#:
G10069815
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
0.14 Acres
Year built:
1957
Courtesy: The Greene Realty Group
View additional info

SOLD AS-IS. Fully furnished. Kitchen remodeled 1998. Water filtration system. New well dug 1999, Electric Panel box replaced 2006. All underground piping from well to house replaced 2010; Windows replaced 2010. Thermostats replaced 2015.

$799,900

160 Pinnacle Ln Chester, CT 06412

Beds:
4
Baths:
8.00
Sq.Ft.:
3,307
Status:
Active
MLS#:
G610147
Type:
Single Family
Subdivision:
Chester (87)
Lot size:
3.12 Acres
Courtesy: Williams Realty Services
View additional info

This 4br, 3.5 Ba home features a graceful open plan w/1st flr master suite, vaulted family room w/stone fp, granite & cherry eat-in kitchen, formal dr & home office/study. 2Nd flr includes 3 br & @ ba as well as a spacious loft.

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