13 Houses For Sale in Chester, CT

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$449,900Est. Payment
3 Beds | 3 Baths | 2,219 Sqft
5 High Field Lane, Chester, CT 06412
House For Sale

PRISTINE! This impeccably kept 3br colonial home located on a quiet cul de sac is "move-in" ready. Nicely landscaped with classic curb appeal, the nearly 3.5 acres of land affords an abundance of privacy which abuts conservation land. Inside...a mill-workers delight. Upon entering the front door you can't help but notice the custom trim and moldings throughout. Newly painted, this sun filled homes' light is managed by the new custom window-shutters throughout. Recently new appliances are surrounded by new granite kitchen counters. The open family room includes a large working fireplace, capable of heating the entire house. Upstairs you will find new fixtures & granite counter tops' in both baths, laundry, a master walk-in closet and a large soaking tub beneath a cathedral ceiling. The clean basement includes custom storage shelving and a painted floor with full double-door walkout to the backyard. Additional features include generator-ready hookup, central vac/air and a 1,250/gal. septic tank. Minutes from the Goodspeed Opera House, Gillette Castle & Rt. 9.

$498,000Est. Payment
5 Beds | 4 Baths | 3,273 Sqft
96 Middlesex Avenue, Chester, CT 06412
House For Sale

This unique property, once a cider mill and orchard, includes a barn style home, circa 1830, on 6 open and landscaped acres. Perfect getaway with multiple outdoor living areas including a wrap around deck with outdoor kitchen, patios, and 2 gazebos. The picturesque acreage boasts flowering shrubs, mature trees and perennial flowers. New England charm and character abound in the interior of the home with 5 bedrooms, 2 fireplaces, a pot-belly stove and milled planking. The great room includes an open kitchen, dining room and large seating area with fireplace, book shelves and vaulted ceiling. A cozy den is complete with another fireplace. The pub/game room, measuring 24 X 22, has soaring ceilings, a built-in bar with sink, and loads of room for entertaining and games. " 5 Car garage too !" This property has already had preliminary work done to subdivide it with 3 additional lots. There is a survey available for the proposed subdivision. The town of Chester has become a well-known destination for an amazing variety of restaurants, one of a kind shops and galleries. Route 9 runs through town and connects to I95 and I84 for an easy commute to New York or Boston.

$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!

$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!

$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!

$549,900Est. 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.

$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.

$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.

$175,000Est. Payment
3 Beds | 4 Baths | 2,208 Sqft
Chester, CT 06412
House For Sale

2208 sq ft. Pre-Foreclosure Single Family Home features 3 bedrooms and 4 bathrooms. Pre-foreclosures can offer opportunities to purchase properties at attractive prices.

$220,924Est. Payment
2 Beds | 2 Baths | 1,392 Sqft
Chester, CT 06412
House For Sale

1392 sq ft. Pre-Foreclosure Single Family Home features 2 bedrooms and 2 bathrooms. Pre-foreclosures can offer opportunities to purchase properties at attractive prices.

$236,000Est. Payment
3 Beds | 3 Baths | 1,092 Sqft
Chester, CT 06412
House For Sale

1092 sq ft. Pre-Foreclosure Single Family Home features 3 bedrooms and 3 bathrooms. Pre-foreclosures can offer opportunities to purchase properties at attractive prices.

$213,350Est. Payment
-- Beds | -- Baths | 3,379 Sqft
Chester, CT 06412
House For Sale

3379 sq ft. Bank owned foreclosure Single Family Home features great opportunity. Bank-Owned Foreclosures can offer opportunities to purchase properties at attractive prices.

$472,500Est. Payment
3 Beds | 2 Baths | 1,248 Sqft
Chester, CT 06412
House For Sale

1248 sq ft. Pre-Foreclosure Single Family Home features 3 bedrooms and 2 bathrooms. Pre-foreclosures can offer opportunities to purchase properties at attractive prices.

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