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Chester Real Estate, Homes and Condos for sale

All Chester homes currently listed for sale in Chester as of 08/20/2019 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

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$950,000
19 West Main Street, Chester CT 06412
3
BEDS
3
BATHS
3,545
SQFT
$268
$/SQFT
0.75
ACRES
1999
BUILT
"Waterfront living at The Jennings Pond Estate - A true hidden gem! A phenomena of history, nature, and architecture privately tucked away in historic Chester Village. This charming contemporary French Country retreat built in 1999 overlooks Jennings Pond and it s magnificent waterfall creating a magical display of water and nature creating a fascinating sense of well-being. The home is in excellent condition and is Appx 3500 Sq ft. It includes a guest house studio with Appx 800 Sq ft of living area. The main house has waterviews from most rooms and has a great open flow. There are 3 large fireplaces, a chefs working French country kitchen Stainless steel Viking gas stove and a subzero refrigerator, a spacious master-suite with attached office/library area and a fireplace. A wonderful bedroom suite on lower lever with fireplace walks out to a terrace overlooking the waterfall. Beautiful perennial beds and herb gardens grace the .75 lot with room for a pool overlooking the Pattaconk River. This piece of heaven is a 5 minute walk to village restaurants, shops and worship facilities. Minutes to major commuting lines and Amtrak stops. 90 mins to Boston and 2 hrs to NYC. Movie buffs will love that Jennings Pond was the site of the 1958 movie It happen to Jane starring Doris Day and Jack Lemmon."
* NEW LISTING 
$899,900
134 Pinnacle Lane, Chester CT 06412
4
BEDS
6
BATHS
6,350
SQFT
$142
$/SQFT
5.86
ACRES
2007
BUILT
"Brimming with charm & character, this custom built and well maintained Adirondack shingle style home offers the perfect blend of traditional architecture and modern home design. Meticulous craftsmanship, quality materials and vaulted ceilings throughout add to the sense of spaciousness while the distinctly versatile floor plan makes this home ideal for entertaining. A welcoming foyer leads to the dramatic two story great room with stone fireplace creating a warm an inviting gathering space for friends & family. The elegant formal dining room with coffered ceilings and the music room/study is the perfect place for enjoying special occasions. A well appointed chef's kitchen with center island features granite counters, high end stainless appliances and offers easy access to a pantry, laundry room, 1/2 bath & 3 car garage. The first floor Master suite and spacious bath with walk-in closet offers convenient one floor living; a private deck is a wonderful place to relax while overlooking park like grounds. Upstairs you ll find an impressive in-home office, 3 guest rooms, 2 full baths and balcony with a view of the great room below. The finished lower level features a game room with fireplace, exercise room, full bath and wine cellar. A private deck with custom pergola provides a relaxing environment and is ideal for outdoor entertaining. Prominently set on 5+ acres overlooking rolling lawns, mature plantings & natural woodlands you will enjoy this special home for years to come."
* NEW LISTING 
$899,900
18 East Liberty Street, Chester CT 06412
5
BEDS
7
BATHS
6,054
SQFT
$149
$/SQFT
2.75
ACRES
1997
BUILT
"Luxury Home set high above the picturesque Village of Chester, CT with it's Upscale Restaurants and Country Shops. The approach down this driveway gives you the feeling of a country estate. The moment you enter this home you'll be in awe of the elegance, it's unique features and style. You'll be great by the view of an large Great Room with a barrel Style High Ceiling, A Drop Down Entertainment Center, a Center Stone Fireplace, a Theatre/Stage and even a Duckpin Bowling Alley! The open Dining area leads to a Gourmet Kitchen with High End Appliances, A Center Island with Seating and French Doors leading to a Wrap Around Deck overlooking Chester Village. The Master Bedroom with a high Barrel style Ceiling, Stone Gas Fireplace, Large Master Bath, Plenty of closets and French Doors that lead to a Patio and the In-Ground Pool. There are (4) Additional Bedrooms, a Den, Office and a Workout room. If you love to Entertain, Play Tennis or are a Thespian in search of a home with an Antique Theatre on site, this just might be the rare find you've been searching for!"
* PRICE LOWERED - $939,900 TO $899,900 
$799,900
88 Goose Hill Road, Chester CT 06412
4
BEDS
5
BATHS
6,261
SQFT
$128
$/SQFT
14.29
ACRES
2001
BUILT
"This Chateau-Castle Style Cape sits on 14+ acres down a gorgeous country road. Devoted to privacy, yet only ~1mile from the quaint village of Chester. As you enter the driveway you ll meet the welcoming garden shed and three-bay barn, then on to the home atop the highest point of the land. The exterior includes stone turrets, chimney pots imported from England and landscape lighting. Out back, seen from the massive wraparound porch are multiple firesides, a frog pond with a waterfall, grilling patio with a roof for year-round use and many thoughtful and intentional gardens. The first-floor master suite also steps out onto the back porch, where indoor/outdoor life collides throughout the day. The kitchen serves two chefs, with dual ovens, sinks, cooktops and dishwashers. Above the three-bay attached garage is a fully equipped studio apartment with a full kitchen, wood stove, laundry, it s own entrance and a large deck to enjoy the prideful grounds. The lower level has a custom built bar, wine cellar, an office/hobby space, workshop, full bath and laundry/mud room. This property boasts so many components and personality, it is nearly impossible to list them all! Chester Center is home to a variety of fine restaurants, art galleries, boutiques and the Norma Terris Theater - part of the Goodpseed program. Home of the highly regarded Summer Sunday Farmer s Market and close to the Chester Hadlyme Car Ferry, providing a time saving alternative for crossing the Connecticut River."
* NEW LISTING 
$799,900
201 Pinnacle Lane, Chester CT 06412
4
BEDS
4
BATHS
3,307
SQFT
$242
$/SQFT
4.10
ACRES
2018
BUILT
"This beautiful two floor custom design home by ASW incorporates the attributes of a home built for entertaining with main floor master suite and laundry to suit an age-in-place lifestyle. The interior has nine foot ceilings atop an impressive open- concept great room and custom gourmet kitchen with granite throughout. Vaulted family room with fireplace. Separate formal dining room and study on main floor, 4 bedrooms, 3.5 baths, loft are all part of this design. Other plans & designs are available ! Call for builders spec's. Subject to change and availability. Agent related"
* LISTED OVER 120 DAYS 
$599,000
42 Winthrop Road, Chester CT 06412
3
BEDS
3
BATHS
1,644
SQFT
$364
$/SQFT
25.60
ACRES
1976
BUILT
"Oakfield Farm, You'll first notice the beautiful stone walls and entry. Running horse sculptures adorn the first pasture as you head into the rest of this 25 acre horse farm. Sitting back off the road is a 1644 sf 3 bedroom 2.1 bath home with master bedrooms with en suite on first floor. The 9 -10 stall barn has 12x12 box stalls, tack room, grooming stall, hay storage and a 1/2 bath. There is a 190 x 140 foot sand ring for riding and training. Long views of pastures with mature oak trees gives this farm it's name. There is even a pond. If your looking for a well thought out horse farm in an idyllic setting, Oakfield Farm is for you. Additional features include a 15x15 sun room that overlooks the farm, 2 additional bedrooms and a full bath on the 2nd floor, 2 car detached garage that is attached to the horse barn, Run-in sheds in the large pastures, security system and possible subdivision potential if your looking for a second residence."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $619,000 TO $599,000 
$575,000
83 West Main Street, Chester CT 06412
3
BEDS
3
BATHS
2,264
SQFT
$254
$/SQFT
1.00
ACRES
1800
BUILT
"Rarely does old world post and beam charm, modern construction, and one floor living come together in such a spectacular setting. Largely re-built with new kitchen and baths, mechanicals, siding, chimneys, and stairs; beams were braced, fresh concrete poured and foundation masonry re-pointed. An entirely new wing was added in the early 2000s housing a 1st floor master suite and a lower level terraced family room. Lovingly maintained by the current owners, the roof and skylights have been recently replaced, copper gutters added, decks re-built, windows and storms updated, French doors replaced, the master bath updated, and the house refreshed with exterior and interior paint. All this can be enjoyed from one of two decks, or one of five patios, overlooking park-like grounds and the Pattaconk brook at boundary s edge."
$550,000
16 Gilbert Hill Road, Chester CT 06412
4
BEDS
3
BATHS
4,100
SQFT
$134
$/SQFT
1.01
ACRES
2004
BUILT
"You will love delightful finely appointed custom home located half mile from downtown Chester shops and restaurants https://www.visitchesterct.com/ Chester offers an easy commute to New York City and Boston. This 4-bedroom home, 2.5-bathroom home has a 2-car garage giving you 2,648 square feet of spacious elegance, natural oak floors throughout. Enter thru the front door into this bright and sunny home with tasteful d cor, and most of all open floor plan with built ins, vaulted ceiling living room with expansive walls of windows. Master bedroom and bath includes jacuzzi with separate walk-in shower, and large California closet. Enjoy the outside with a covered porch and a fenced-in backyard with deck and patio overlooking the salt water heated pool. Coming home to this warm setting is simply just that Coming Home!"
$489,900
22 Old County Road, Chester CT 06412
4
BEDS
4
BATHS
3,630
SQFT
$135
$/SQFT
3.62
ACRES
1986
BUILT
"Situated in the heart of the picturesque Lower Connecticut River Valley, this fascinating, Contemporary hilltop retreat boasts an open floorplan enhanced by soaring ceilings & expansive walls of windows. Flooded with natural light, the home is warm & inviting, creating the ideal space for comfortable, everyday living as well as a wonderful place to graciously entertain family & friends. The eat-in kitchen is newly renovated & features quartz countertops, tile backsplash & stainless appliances. The first-floor, master bedroom suite includes a gracious sitting room with French doors that provide access to the expansive, multi-faceted deck. The spacious family room & exercise area have a separate outdoor access & offers the potential for an in-law or au-pair suite. The property s professional landscaping incorporates a variety of perennial plantings with the mature trees that heightens the beauty of the home s natural surroundings. Chester is renowned for its quaint village featuring unique shops, numerous galleries & diverse restaurants. Multiple marinas & boat launches are found along Chester s river front offering boaters & water sports enthusiasts access to this recreational water course. Entrances to the Cockaponset State Forest provide hikers, bikers & horseback riders with miles of trails to explore. Chester offers an easy commute between Hartford, New Haven & New London and is located only two & one-half hours by automobile from both New York City & Boston."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $499,900 TO $489,900 
$488,000
45 Main Street, Chester CT 06412
5
BEDS
5
BATHS
3,531
SQFT
$138
$/SQFT
0.19
ACRES
1790
BUILT
"Chester Village cash cow! Annual rental potential of $60K gross. Beautifully restored 3 unit building with charm and character overlooking the beautiful Pattaconk river. Live for free in one unit and rent out the rest or rent all three. The middle unit is perfect for a business downstairs and live upstairs situation. The first two units are two bedroom, 1.5 bath, townhouse style with laundry on the second floor. The third unit is ranch style with one bedroom and one bath and is in pristine condition - currently used as an Air B&B with a strong rental history. The two bedroom units are adorned with stunning wide-plank hardwood floors and magnificent fireplaces, and all three have an added touch of character and history with beautiful wooden beams decorating the ceilings. All three units have separate utilities and basement storage, as well as their own private deck overlooking the peaceful and serene Pattaconk river. City water and city sewer. Unbeatable location with shopping, restaurants, and galleries just outside your front door. Convenient to Route 9 and I-95. The property is also zoned commercial."
* PRICE LOWERED - $499,000 TO $488,000 
$439,000
5 West Main Street, Chester CT 06412
2
BEDS
2
BATHS
2,610
SQFT
$168
$/SQFT
0.08
ACRES
1900
BUILT
"Investors dream! Live and work in one of New Englands quintessential, Historic towns! Great location in the charming village of Chester, this beautifully remodeled mixed use building abuts the Pattaconck brook and is currently being used as a residence and commercial space. The lower level two bedroom apartment has been beautifully remodeled with newer kitchen and bathroom, extra large walk in closet in master bedroom with 1/2 bath and laundry. Retail store front at street level provides income with flexible rental space for 2-4 units, can easily work for retail, office, salon, art gallery, art studio to suit your needs. Extra storage in the full attic as well as the basement. Visitors, artists and musicians alike enjoy this vibrant community with many shops, art galleries and restaurants within walking distance as well as local attractions featuring the Chester-Hadlyme ferry to Gillette Castle State Park, Norma Terris Theatre and seasonal Farmers market. Property also listed as commercial listing - 170197774"
$399,900
28 Winthrop Road, Chester CT 06412
3
BEDS
3
BATHS
1,980
SQFT
$202
$/SQFT
13.00
ACRES
1947
BUILT
"BEAUTIFUL NEW CONSTRUCTION ON 13 ACRES. CAPE STYLE HOME WITH 3 BEDS A 2.1 BATHS. BLUE STONE WALKWAY. OVER-SIZED ATTACHED 2 CAR GARAGE. HARDWOOD FLOORS THROUGHOUT MAIN LEVEL. HUGE EAT IN KITCHEN WITH CATHEDRAL CEILINGS AND RECESSED LIGHTING. SLIDER OFF THE REAR TO AN OVERSIZED PATIO. BREATH TAKING VIEWS! LIVING ROOM WITH WALL MOUNTED ELECTRIC FIRE PLACE. MASTER BEDROOM WITH WALK IN CLOSET AND FULL BATH. UPSTAIRS HAS A FAMILY ROOM WITH NEW CARPET IDEAL FOR KIDS PLAY ROOM AND AN OFFICE. BRAND NEW SEPTIC SYSTEM. WALKING DISTANCE TO CEDAR LAKE. CLOSE TO CHESTER AIRPORT. MANY POSSIBILITIES WITH ALL THIS LAND!!"
* PRICE LOWERED - $409,900 TO $399,900 
$399,900
38 Railroad Avenue, Chester CT 06412
4
BEDS
3
BATHS
2,226
SQFT
$180
$/SQFT
1.18
ACRES
1918
BUILT
"Charming 1918 Colonial with curb appeal!! Situated on a park like setting with a beautiful deep backyard including a barn! Less than a mile walking distance to Chester Village! Walking distance to Chester Marina! The yard is a gardeners dream! Welcoming front porch! Spacious entry foyer opens up to the living room with a gas fireplace, built-ins & hardwood floors. Large formal dining room with built-ins & a gorgeous vintage lighting fixture! The kitchen was completely remodeled with white cabinetry, quartz counter tops, a farmhouse sink, stainless appliances & wonderful pull-out storage everywhere! The main floor master bedroom has a walk-in closet, full bath & french doors leading to the deck! Main floor laundry closet has full sized stack-able washer & dryer. Main floor den/family room is perfect for TV watching with a cozy gas fireplace & atrium doors to the expansive deck! The mudroom adjacent to the kitchen is the full length of the garage with storage galore! 2 car garage is attached to the mudroom/breezeway. 3 additional bedrooms on upper level with another full bath. There is a walk-up attic for easy storage access. The Trex deck & front porch are low maintenance. Charming barn out back has a gardeners potting area, great storage & a whimsical playroom for your pool table or hobbies! A grape arbor adds a nice touch in the garden. This home offers all the character you want with all the updates for your comfortable living!"
* PRICE LOWERED - $414,900 TO $399,900 
$389,900
289 Middlesex Avenue, Chester CT 06412
2
BEDS
2
BATHS
1,040
SQFT
$375
$/SQFT
8.67
ACRES
1974
BUILT
"Ct. Water Views! Gem of a Ranch with central air conditioning sited on 8.67 acres. Hardwood floors through out home. Two nice size bedrooms, Master bedroom with slider to patio area and hot tub. Kitchen with slider to brick patio and hot tub .Combination living room/dining room with bow window with views of Ct. River, built in bookcases, and wood burning fireplace with wood stove insert. Large yard for gardening and fenced area and privacy for the whole family to enjoy. This home can be expanded or BUILD YOUR DREAM HOME ON KNOLL and subdivide ranch on 2 acres, while living in the ranch. Area of fine homes. Basement can be finished for family room/rec room or office. Over sized garage with plenty of storage and/or workshop. This charmer is close to quaint Chester Village for shopping, restaurants, Ct. River and marinas for you boaters! Convenient location for commuting. Mid way between New York and Boston. Amtrak close by. RARE OPPORTUNITY AWAITS YOU!"
* LISTED OVER 120 DAYS 
$379,000
81-2 Turkey Hill Road, Chester CT 06412
3
BEDS
3
BATHS
2,032
SQFT
$187
$/SQFT
6.82
ACRES
1988
BUILT
"Nature lovers take notice! This private 6.82 acres abuts the Cockaponsett State Forest. Flat around the house, but rolling to the forest. Built in 1988, this contemporary home has been lovingly and meticulously cared for by the owners. It boasts a large three car garage, beautiful eat in kitchen, dining area, hot tub room, conversation pit, living room, three bedrooms, 2 1/2 baths and loads of storage. A rose garden, horseshoe pit and nature trails make this a spectacular paradise for nature lovers! Freshly painted in a gray tone through the interior. Just waiting for new owners to live it as much as the current owners have for years!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $389,000 TO $379,000 
$299,900
89 Cedar Lake Road, Chester CT 06412
2
BEDS
2
BATHS
1,336
SQFT
$224
$/SQFT
4.00
ACRES
1806
BUILT
"A gentleman's farm on 4 picturesque acres of rolling countryside and meadow land with babbling brook and waterfall, this 6 room country Cape circa 1806, has been lovingly restored and updated. All rooms and ceilings have been freshly painted. The kitchen features new cabinets and granite counter tops. The spacious dining room and living room are accented with walls of reclaimed old barn board. The dining room and living room are separated by a sliding barn door authentically hand crafted by a local artisan. Wood floors through-out the first floor and carpet upstairs. Replacement windows. A short walk to Cockaponsett State Park with seemingly unending hiking trails and Cedar Lake with two resident beaches and boat launch ideal for small boats and canoes. A picture perfect country escape."
* PRICE LOWERED - $315,000 TO $299,900 
$295,000
7 Castle View Drive, Chester CT 06412
3
BEDS
2
BATHS
1,758
SQFT
$168
$/SQFT
0.36
ACRES
1960
BUILT
"Super Sweet Updated Ranch with Inground Pool in Great Price Point in CHESTER! Features Include * New Roof 2016 * Newer Windows * New Furnace 2016 * Remodeled Family Room * Granite Kitchen wi Stainless Appliances * Central Air & Attic Fan * Recessed Lighting * Hardwood Floors * New Hot Water Heater 2016 * Decorative Wainscoting in Kitchen * New Carpet in Living Room wi Fireplace & Built-Ins * The back yard with the pool is completely fenced in for privacy and entertainment along with the electric equipped pool house. The master bedroom and bath has been remodeled and features additional built-in closets, a cozy window seat plus beautiful fully tiled bath in pleasing colors for any d cor. User friendly basement opens into 12'X23' sunroom space offering more living and relaxing area looking out on to back yard and pool. This home is move in ready and the current sellers have enjoyed their time here!"
$249,900
6 Middlesex Avenue, Chester CT 06412
4
BEDS
2
BATHS
2,374
SQFT
$105
$/SQFT
1.49
ACRES
1900
BUILT
"Charming Colonial with wrap around front porch. This home retains much of its old world charm with some updating done. Updates include thermal windows, vinyl siding, and an addition off the rear adding a 19 x 24 family room with cathedral ceiling. Patio doors lead to the deck overlooking the private backyard and inground pool. First floor laundry room. Home office. Detached 2 car garage."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $275,000 TO $249,900 
$239,900
115 Goose Hill Road, Chester CT 06412
3
BEDS
2
BATHS
1,755
SQFT
$137
$/SQFT
1.00
ACRES
1968
BUILT
"Much remodeling and updating done on this three bedroom Cape with potential one bedroom in-law apartment on the lower level. The living room is open to the kitchen and has a cathedral ceiling with exposed beams. New roof. New siding. New thermal windows. Quiet country setting with 16 x 24 barn."
$219,000
7 Railroad Avenue, Chester CT 06412
2
BEDS
1
BATHS
784
SQFT
$279
$/SQFT
0.10
ACRES
1905
BUILT
"Start your morning seeing the sunrise from your master bedroom and close the day relaxing with friends on the farmers porch. This perfect perch is a stroll to all of Chester Village with restaurants, art galleries, artisan shops, and of course the amazing Chester Farmers Market on Sunday mornings in season and is approximately 1/2 mile to Connecticut River and marinas. 2 bedrooms on the second floor, kitchen, breakfast nook, living room and full bath on the first floor. A tidy yard with space for gardening, full basement and one car garage. The roof was replaced 2016, and house (exterior) professionally painted in 2018. This sweet little home has just what you need."
* PRICE LOWERED - $229,000 TO $219,000 
$109,900
65 Middlesex Avenue, Chester CT 06412
2
BEDS
1
BATHS
792
SQFT
$139
$/SQFT
0.26
ACRES
1905
BUILT
"CLASSIC CAPE WITH ITS ORIGINAL CHARM. OPEN FRONT PORCH LEADING INTO A CHARMING ENTRY. ORIGINAL TRIM, HARDWOOD FLOORING. ENCLOSED REAR PORCH OVERLOOKING CARINI PARK. FULL WALKOUT BASEMENT WITH HIGH CEILINGS. SHORT DISTANCE TO DOWNTOWN AND MAJOR ROADS."
* NEW LISTING 
 
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