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26 Chester, CT Real Estate Listings

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$469,900Est. Payment
3 Beds | 3 Baths | 1,644 Sqft
45 Maple Street, Chester, CT 06412
House For Sale

Prominently set on a quiet street in the heart of Chester, this well known & often admired village property is just what you have been looking for in the perfect shoreline home. The original house, built in the 1820's, was lost in a fire in 2004. With the guidance of architect Stephen Lloyd & master builder Bruce Lawrence of Bogaert Construction, the current owners created a new vision of the perfect home by combining traditional architecture with modern home design. Built on the original footprint to retain the old world charm the new house was completed in 2006. Stone steps lead to a gracious entry, the music room/study, a well-appointed kitchen w/new appliances & a light filled dining area...ideal for entertaining. The adjacent great room, brimming with charm & character, is centered around a custom fireplace built from hand selected stones from the original foundation. A full bath with a hand painted mural by well-known artist Liz Gourlay completes the first floor and in the center of the house is a unique custom stairway leading to the upper level... the the perfect space to highlight your favorite artwork. At the top of the stairs are two guestrooms with a shared bath & a romantic master suite with spa-like bath, cozy fireplace, an overhead skylight for stargazing & private deck overlooking park-like grounds. The lower offers plenty of storage and will give peace of mind with updated mechanicals. Located on .98 of an acre enjoy all Chester Village has to offer.

$369,900Est. Payment
2 Beds | 2 Baths | 1,040 Sqft
289 Middlesex Avenue, Chester, CT 06412
House For Sale

Charming two bedroom Ranch overlooking the CT River in the lovely "Historic" town of Chester. Beautiful water views of the CT River and valley on 8.67 acres of private land(may be subdivideable). This cozy ranch features hardwood floors, fireplace with a wood stove insert, sliders off kitchen and mbr, all appliances , 1 car garage, rear patio and so much more. Check out the 3D Tour ! Great size basement waiting to be finished (get out your drawings - family room, office...). Experience the beauty and culture Chester has to offer every day (Gillette Castle, Goodspeed Opera House, Essex Steam Train and Riverboat, shops, galleries, original Award Winning art created by local artists, delicious food..... Don't miss out! This home is going to go fast! Schedule your showing today! We are always here to help!

$995,000Est. Payment
3 Beds | 2 Baths | 1,888 Sqft
9 Parkers Point Rd, Chester, CT 06412
House For Sale

CT River Waterfront! Well maintained three bedroom Cape with charming Guest Cottage on nearly 4 acres gently sloping to the CT River. Over 300 ft of frontage in a No Wake Zone. Beautiful views and setting! The main house has two first floor bedrooms including the Master Suite. The third bedroom is spacious and on the second floor. It could make a great home office or hobby/media room. The family room has an original stone fireplace, custom built in shelving, and original beams. There is also a fireplace in the guest cottage. The enclosed porch and stone patio are situated nicely to relax and take in the views!

$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.

$279,900Est. Payment
3 Beds | 3 Baths | 1,192 Sqft
31 Castle View Dr, Chester, CT 06412
House For Sale

Open and bright floor plan. The first floor has a spacious 15 x 16' Living Room, kitchen with breakfast bar, dining room with slider to a 12 x 38' deck across the entire rear of the house. Two bedrooms and full bath. Finished lower level has a family room, bedroom and a full bath with potential for an in-law apartment. Buderus Furnace. Generator hook up. Two car under garage. Above ground pool needs work.

$10,000
$275,000Est. Payment
3 Beds | 3 Baths | 1,092 Sqft
37 Castle View Dr, Chester, CT 06412
House For Sale

Three bedroom Gambrel Colonial on a loop road in a quiet neighborhood. The Living Room is open to the Eat-In Kitchen. First floor bedroom with common access to a half bath. Potential to add a full bath on the first floor for true one floor living. 12 x 18' deck across the entire rear of the house. Two additional bedrooms and a full bath on the second floor. The walk out basement is ready for your finishing. Two car oversized garage with pulldown stairs to loft above. Needs some work including exterior paint and some trim repair.

$485,000Est. Payment
1 Bed | 3 Baths | 2,177 Sqft
61 Main Street, Chester, CT 06412
House For Sale

59-61 Main Street, Chester, Connecticut. Iconic dining landmark, this is currently operating as the award winning Hot French Chix. Zoned C (Commercial) this building offers exceptional flexibility in its Mixed Use Retail/Apartment definition. The outstanding integrity of construction is evident in this granite stone foundation, nearly 9' high interior ceilings, exposed antique beams, wide board wood floors, tile floors, all drenched in natural sunlight. Currently being used as a full service restaurant and bar on the main level, and one bedroom apartment on the second level of approximately 726 sf. There are two commercial kitchens, one on each level, plus a full dry basement for storage. Chester Village is a destination for locals and city visitors from New York, Boston, Providence and more. Location is prime and pristine just 10 minutes to the CT shoreline beaches of Long Island Sound and CT River Valley with an upscale country vibe. You'll be delighted to find antique shops, nautical stops, retail, dining, art galleries, more. This property can be transformed to suit your creative business and personal dreams. All kitchen and restaurant equipment conveys. Your restaurant (s), speakeasy, retail, art, museum, bar, etc will be a perfect addition to this desirable village. Live on the premises if you wish. Liquor license is in place but please make your application according to State of CT guidelines. You may lease out the entire building or a portion of it if you choose.

$449,900Est. Payment
3 Beds | 3 Baths | 2,880 Sqft
17 High Street, Chester, CT 06412
House For Sale

One-of-a-kind, Grand Colonial , 10 minute walk from Chester Village. Impressive Foyer welcomes you to the home leading to Formal Dining with French Doors and Living Room each with fireplaces. Kitchen showcase stainless steel appliances, granite counters, and large island. A second dining area or den can accommodate further family entertaining. Upper floor showcases hallway with stately chandelier and ornate windows leading to Master Bedroom Suite with sitting room, fireplace and newly renovated bathroom. Two additional bedrooms with a shared newly renovated bathroom. Full length front veranda with great views, perfect for outdoor cocktail parties and rocking chair relaxation. Gorgeous , private and quiet backyard with manicured moss garden and tons of raspberry bushes at the back of the property. Quarts and quarts of raspberries harvested last summer.! Plenty of birds as well who are attracted by the berries and vegetation. Very private space with tall trees in back and lining both sides of the property down to street level. Full House Generator Hookup available.

$325,000Est. Payment
3 Beds | 2 Baths | 2,196 Sqft
25 East Liberty Street, Chester, CT 06412
House For Sale

Built in 1800, this authentic colonial features original wood floors, door hardware and lighting fixtures. Two enclosed porches flood the entire first floor with natural light creating a cozy and cheerful atmosphere. Large and updated eat-in kitchen opens through French doors to one of the enclosed porches - perfect for entertaining. Conveniently situated full bath and laundry room are nestled privately off the kitchen. Partially finished attic is floored and offers unlimited potential. Two separate staircases lead to the second floor. Serene private backyard is surrounded by beautiful stone walls and includes a man-made rock pool and patio. Owned by a local artist, the home is colorful and fun with many creative details. Within walking distance to quaint Chester Village and Chester Cove.

$499,900Est. 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. There are 2 and 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 the Goodspeed Norma Terris theater.

$389,900Est. Payment
2 Beds | 2 Baths | 2,112 Sqft
3 Story Hill Road, Chester, CT 06412
House For Sale

Beautifully remodeled Chester Cape full of charm and coziness. Wide pine floors, gas stone fireplace, new open kitchen dining and a front porch to watch the sunsets are sure to please a first time or down sizing buyer. Finished walkout lower level with family room and office space, central vac, propane fueled dryer and oven range, views of the Chester green all within walking to the village. Come see what Chester has to offer. Only two hours from Boston or New York.

$169,000Est. Payment
7 Acres
180 Pinnacle Lane Lot #19, Chester, CT 06412
Lots Land For Sale

Beautiful lot in a neighborhood of fine homes. Chester Forest Estates is a prestigious neighborhood of 19 custom built homes. Located in the picturesque community of Chester, CT. Building lots are a minimum of 2 acres providing natural wooded settings for each home. Just minutes from Rt. 9 and the Village of Chester, Chester Forest Estates offers elegance, comfort and convenience in a special country setting. Deed restrictions apply. Owner/Agent

$119,000Est. Payment
4.09 Acres
190 Pinnacle Lane Lot 14, Chester, CT 06412
Lots Land For Sale

Beautiful lot in a neighborhood of fine homes. Chester Forest Estates is a prestigious neighborhood of 19 custom built homes. Located in the picturesque community of Chester, CT. Building lots are a minimum of 2 acres providing natural wooded settings for each home. Just minutes from Rt. 9 and the Village of Chester, Chester Forest Estates offers elegance, comfort and convenience in a special country setting. Deed restrictions apply. Owner/Agent

$129,900Est. Payment
4.1 Acres
201 Pinnacle Lane Lot 12, Chester, CT 06412
Lots Land For Sale

Beautiful lot in a neighborhood of fine homes. Chester Forest Estates is a prestigious neighborhood of 19 custom built homes. Located in the picturesque community of Chester, CT. Building lots are a minimum of 2 acres providing natural wooded settings for each home. Just minutes from Rt. 9 and the Village of Chester, Chester Forest Estates offers elegance, comfort and convenience in a special country setting. Deed restrictions apply. Owner/Agent

$129,900Est. Payment
4.46 Acres
220 Pinnacle Lane Lot #13, Chester, CT 06412
Lots Land For Sale

Beautiful lot in a neighborhood of fine homes. Chester Forest Estates is a prestigious neighborhood of 19 custom built homes. Located in the picturesque community of Chester, CT. Building lots are a minimum of 2 acres providing natural wooded settings for each home. Just minutes from Rt. 9 and the Village of Chester, Chester Forest Estates offers elegance, comfort and convenience in a special country setting. Deed restrictions apply. Owner/Agent

$169,000Est. Payment
7.82 Acres
170 Pinnacle Lane Lot 18, Chester, CT 06412
Lots Land For Sale

Beautiful lot in a neighborhood of fine homes. Chester Forest Estates is a prestigious neighborhood of 19 custom built homes. Located in the picturesque community of Chester, CT, All building lots are a minimum of 2 acres providing natural wooded settings for each home. Just minutes from Rt. 9 and the Village of Chester, Chester Forest Estates offers elegance, comfort and convenience in a special country setting. Deed restrictions apply. Owner/Agent

$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.

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