26 Chester, CT 06412 Real Estate Listings

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$342,500Est. Payment
3 Beds | 3 Baths | 2,311 Sqft

40 Middlesex Avenue, Chester, CT 06412

House For Sale

Wonderful opportunity to own a classic Victorian farmhouse just a stones throw from fabulous Chester Village! This home has been maintained and updated throughout the many years the seller has owned it and has some great features including wrap around farmers porch, beautiful restored period trim and moulding, and an updated kitchen by a well known area kitchen designer. The BIG bonus to this property is the one bedroom apartment for income or private guest suite.

Open 1/17
$399,000Est. Payment
3 Beds | 3 Baths | 4,692 Sqft

74 Turkey Hill Road, Chester, CT 06412

House For Sale

Beautiful colonial located in the charming town of Chester, close to town and Cedar Lake! Privately set off of Turkey Hill Road with convenient access to Route 9. This 3,400 sq ft house situated on 2.91 acres has 3 bedrooms, 3 full bathrooms, office, formal dining room, living room, and bonus room above the garage. The living room/formal dining room features a lovely bay window and brick fireplace. Off the kitchen is a wrap around deck with plenty of space for outdoor entertainment. The bonus room above the garage features a beautiul stone fireplace and vaulted ceilings. The full basement includes walkout to the yard and a workshop area. Central air updated with new unit in place. The walk up attic is all framed out for a master suite or additional bedrooms. Attached 2 car garage and mudroom with plenty of storage space. Large master suite with walk in closet and full bathroom. Schedule your showing today!

$150,000Est. Payment
2 Acres

16 Old County Road, Chester, CT 06412

Lots Land For Sale

Truly one of the best locations in Chester. A rare find. Breath taking views of the river valley, private location on private drive shared only by 2 other well appointed and cared for homes. Utilities already on property and asphalt driveway to house site exists. No other building lots like this in town. Mature trees, rock out croppings with deeded cutting rights over three other properties to maintain view easement across other properties.

$265,000Est. Payment
4 Beds | 2 Baths | 1,428 Sqft

2 Marina View Drive, Chester, CT 06412

House For Sale

Walk to the water from this little gem! Located on a corner lot in a small neighborhood, close to town and water! A wonderful 4 bedroom Cape with 2 full baths, fireplace and deck. Upstairs was finished around 2013 and the first floor bathroom was updated then too. The driveway was newly paved in the last 8 years. The home sits on .50 acres with a sprawling front lawn. A must see!

$1,350,000Est. Payment
3 Beds | 5 Baths | 3,876 Sqft

260 Middlesex Avenue, Chester, CT 06412

House For Sale

This remarkable country home becomes available for the first time in over 30 years. Until recently the rural retreat of a renowned journalist, it is located in the charming small town of Chester, Connecticut. New York City and Boston are just over two hours by car or train. Spread over 7 private park-like acres, the landscape is filled with such diverse decorative elements as a Bermudian moon gate, an Italian garden grotto, and prides of terracotta and stone lions. The center of the house is the original early 20th C eclectic cottage with its multiple architectural styles ranging from Medieval to Arts and Crafts. Surrounding the original cottage, a totally reconceived home now has a large stone patio, a spacious family room/kitchen, 2 fireplaces, 4 full baths, a classic English greenhouse, and a first-floor master suite with beamed cathedral ceiling and a huge closet/dressing room/storage area. Separated from the main house, an ample writer's studio, with wood-burning fireplace, a fifth full bath with steam shower, and a covered porch overlooks a heated swimming pool and gazebo. The 19th C. barn incorporates a new four-car garage. All this is just a mile from downtown Chester, home to artists and writers, a theater, some of Connecticut's finest restaurants and a celebrated Sunday Farmers Market in the town center from May through October. And when it's time to leave, your full house generator, security system and irrigation system will keep watch until you return.

$199,900Est. Payment
3 Beds | 1 Bath | 1,183 Sqft

5 Brookside Road, Chester, CT 06412

House For Sale

Enjoy one level living in this move-in ready Ranch on Cedar Lake! Situated on a corner lot at the end of a cul-de-sac, right across the street from your driveway is your deeded access way to Cedar Lake by small boat, canoe or kayak. Close by is the larger, state boat launch. This well maintained home offers hardwood floors, a spacious living room with large windows allowing lots of natural light and an eat-in kitchen with slider out to the large deck perfect for entertaining. Plenty of cabinet and counter space and a convenient mudroom with pantry off the kitchen. 3 spacious bedrooms with abundant closet space complete the main level. Lots of room in the basement for storage, and an attic capable of pull down-stairs allow for more storage. Enjoy year round living and swimming, fishing and boating all summer at the lake!

$369,000Est. Payment
-- Beds | -- Baths | 2,610 Sqft

5 West Main Street, Chester, CT 06412

Multi Family For Sale

Lucrative investment opportunity in downtown Chester for multiple apartments or mixed use! The Village of Chester known for its quaint shops, galleries, and excellent restaurants is a highly sought-after destination with limited apartment inventory. Being in the middle of all the action, this property has endless possibilities with 3,000 SF +/- of utilizable space. Be part of this wonderful community in this beautifully renovated historic building! This previously under contract listing is now back on the market and priced to sell! **Rare in Chester: 5-6 Parking Spaces located on Lower Level**

$110,000Est. Payment
1.89 Acres

48 Wig Hill Road, Chester, CT 06412

Lots Land For Sale

Beautiful level 1.89 acre lot with old stone walls. Raw land - bring your plans and build your dream home in the lovely town of Chester! Chester is ideally situated midway between NYC and Boston, making Chester a popular destination for weekend getaways. Stroll the enchanting Village of Chester known for its charming shops, outstanding restaurants and the Norma Terris Theatre. Take a ferry across the Connecticut River to Gillette Castle or drive to the quintessential New England town of Essex, or Mystic Seaport and downtown Mystic. Plenty of places to explore and things to do, so bring your plans and bring your dreams and find yourself HOME SWEET HOME!

$369,500Est. Payment
4 Beds | 3 Baths | 2,622 Sqft

16 Ridge Road, Chester, CT 06412

House For Sale

Lovely Colonial home in prime Chester location. Beautifully appointed with unique additional living spaces. Remodeled attractive kitchen opens to Family room featuring cathedral ceilings and access to large private deck w/hot tub. This special home also offers formal living and dining rooms, plus a 1st floor den w/half bath all with period wood floors and crown moldings. Upstairs is 3/4 bedrooms with wood floors. The additional living spaces include a walk up attic and a converted garage into great room in the lower level. This space is open and bright, fabulous for many uses. The quaint front wrap around porch is a great spot to enjoy a cup of tea and a comfortable rock in your favorite chair. Outside features include outbuilding and brand new septic system. All of this is within walking distance to Chester Village and Chester Elementary School.

$299,900Est. Payment
11.65 Acres

18/1 Hoop Pole Hill Road, Chester, CT 06412

Lots Land For Sale

18/1 Hoop Pole Hill Rd., Chester, CT! Developers & Builders take note: 11.65 acres, 950+/- frontage nestled on a peaceful country road. Possible 2/3 picturesque lots. Build your dream home and enjoy amazing views, rolling hills, pastures and forests of Hoop Pole Hill. In an area of fine homes of Chester Forest Estates! Enjoy the rich history of Chester and surrounding towns like Deep River, Essex, Haddam and E. Haddam. Amazing views and Summertime enjoyment at Pattakonk Recreational Area and Cedar Lake. Town lake rights to Cedar Lake for residents for swimming, two beaches, life guards on duty, free parking & swimming lesson. Goodspeed Opera House, Gillette Castle, Chester-Hadlyme Ferry, Essex Steam Train, and countless restaurants and shops, are just some of the many reasons you'll want to build your dream home in the quaint rural town of Chester. Close to RT 9 and just a short drive to the shoreline!

$559,900Est. Payment
3 Beds | 3 Baths | 2,302 Sqft

24 Pleasant Street, Chester, CT 06412

House For Sale

Located on 1.11 acres in the quintessential Chester Village, this 1850's Federal Colonial was remodeled from the studs out in 2004. The kitchen has custom cherry cabinets, granite countertops and new mosaic glass backsplash. The cabinets carry through into one of the two dining areas, perfect for entertaining. This home is complete with two gas fireplaces in both the living room and master bedroom. Very large family-room with sliders to patio area. There are 2 1/2 baths with the master bath having a Jacuzzi tub. Second floor laundry area for convenience. There is a two story garage for extra storage or hobbies. Within walking distance to all of Chester Village restaurants, shops, and elementary school. Room for pool.

$415,000Est. Payment
3 Beds | 3 Baths | 2,065 Sqft

64 West Main Street, Chester, CT 06412

House For Sale

This Historic Chester home, Circa 1850, is absolutely wonderful! A beautiful level yard with privacy fence and raised bed gardens leads to a Barn/Garage complete with workshop and a second floor office space. This home has a formal front parlor which opens to a spacious Living room/ Dining room with lovely builtins. From the dining room take your coffee or cocktail to a peaceful enclosed porch overlooking your raised bed gardens. The warm and welcoming kitchen has a Fireplace with woodstove insert for those cool Fall and Winter days. Off the kitchen is another wonderful porch with bluestone floor. This porch is screened, and ideal for entertaining friends and family. Two staircases access the second floor where there are three pretty bedrooms with wideboard floors and two bathrooms. The Master Bedroom is quite bright and spacious. A portion of the basement area is used by the current owner for her design business. Move to Chester! Walk to town! This quaint Connecticut River Village has amazing Shops and Restaurants! Easy access to major highways. Located midway between Boston and New York. You will love this home and property!

$859,000Est. Payment
3 Beds | 3 Baths | 1,978 Sqft

71 Dock Road, Chester, CT 06412

House For Sale

THIS is what Waterfront Living is supposed to be about. Accept no substitutes. You cannot get much closer to the water, unless you're in a boat! A turnkey CT River dream escape from any and all of life's cares. Lovingly remodeled from top to bottom. Spacious kitchen/great room incorporates an island, stainless appliances, oven/range w/hood, wall ovens, dining area with bay windows, home theater and sliders to a spacious deck overlooking the river, your own private sandy beach and a kayak launch. Approximately 2,000SF of carefree living on one floor. Master suite with full bath and private deck. Two guest bedrooms, two additional full baths, plus office with Murphy bed and laundry room. Zoned propane heat, on-demand hot water and central air conditioning. Nearby Chester Village is reknowned as an eclectic melting pot where artists, artisans, writers, actors, foodies, followers of fashion, farmer's market devotees, captains of industry and fifth generation natives all mingle on a Main Street ripped straight from a Hollywood movie lot built to evoke the perfect New England small town. To-die-for restaurants, coffee shops and useful boutiques beckon. Just ten minutes of country drive will bring you through Deep River to Essex village, steeped in a rich seafaring history and graced by well-preserved period homes, yacht clubs and marinas. Whether out exploring, or sitting home watching the river roll by, life is good here. Only a bit over two hours to NYC or Boston.

$475,000Est. Payment
1 Bed | 1 Bath | 2,177 Sqft

59-61 Main Street, Chester, CT 06412

House For Sale

With a fabled history and successful present, 59-60 Main Street is a prominent building in the sought after village of Chester. With a truly charming studio apartment on the second floor befit for a true entrepreneur, you can live where you work (or rental income potential). Chester has become a small business haven; clusters of bespoke shops, galleries and restaurants line the streets with apartments such as this nestled on the second floor. This space has also been a "hidden" restaurant. The studio is complete for the home-chef or professional food service business with commercial kitchen. The roof deck is something special for private parties or your own personal getaway. Downstairs is included in this sale; a complete restaurant with all fittings run it yourself or rent it. This successful restaurant comes with a famous history. This dual usage space is something you really must see in person to understand just how one of a kind it is. Virtual tour available. Commercial listing MLS #170305939.

$89,000Est. Payment
0.89 Acres

02 Main Street, Deep River, CT 06412

Lots Land For Sale

Location Location first time offered this lightly wooded .89 acre lot is located on Main street near downtown. Once part of a large parcel it was a Nursery in 1920's designated to grow Evergreen trees for the war effort to be made into Gliders to fly quietly into enemy territory. Beautiful holly Rhododendron and evergreens are scattered through out the property which shares a partial sideline of the property on Sylvan Terrace .42 acres also listed for sale at $79 000. MLS#170343622.Close to downtown amenities and CT River Landing. Devitts Field baseball diamond local dining and grocery stores. Region 4 schools. Excellently located near Tacos Farm stand Deep River Market Tailgaters Pub within a mile of Scott's Orchard Deep River Farm and coffee stop Plattwood Park- swimming fishing skate-park playscapes baseball diamond and even movies on the beach (seasonal) Laimar Show Stables across from park.Please do not walk property with out an appointment. Thank you.

$875,000Est. Payment
3 Beds | 3 Baths | 3,545 Sqft

19 West Main Street, Chester, CT 06412

House For Sale

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.

$254,900Est. Payment
4 Beds | 2 Baths | 1,224 Sqft

15 Wig Hill Road, Chester, CT 06412

House For Sale

Close to the center of Chester Village, this cozy four bedroom cape on 2 private acres has a patio with a stone fireplace perfect for enjoying the quiet yard. With hardwood floors throughout and recess lighting, the home offers two first floor bedrooms and two on the second. A lower level family room with a wood stove and sliders provides more living space.

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