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23 Homes For Sale in Chester, CT

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New
$169,000Est. Payment
7 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 Related

New
$119,000Est. Payment
4 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 Related

New
$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.

New
$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.

$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!

$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.

$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.

$10,000
$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!

$10,000
$539,900Est. 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.

$40,000
$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.

$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!

$20,000
$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.

$45,100
$215,000Est. Payment
1.5 Acres
11 Kings Highway, Chester, CT 06412
Lots Land For Sale

Escape to sought after quaint Chester and design your own dream home on an approved hilltop building lot with South facing water views. The 1.5 acre lot is clear cut and perfect for a passive or active solar home. An approved driveway is in place from street to top. Views of the Lower Connecticut River valley to the Lyme hills and past the Deer River harbor. Walk less than a mile to Chester Village to enjoy restaurants, theater and other amenities. Public water and utilities at road, three bedroom septic plan is in place. Ideal for year-round or second home.

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