Chester CT Real Estate & Homes for Sale

20 Properties Found

The median home value in Chester, CT is $337,500. This is higher than the county median home value of $252,200. The national median home value is $185,800. The average price of homes sold in Chester, CT is $337,500. Approximately 62.07% of Chester homes are owned, compared to 26.34% rented, while 11.59% are vacant. Chester real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Chester real estate agent to arrange a tour today!
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Beds:
4
Baths:
4.00
Sq.Ft.:
3,630
Status:
Active
MLS#:
170142533
Type:
Single Family
Subdivision:
N/A
Lot size:
3.62 Acres
Year built:
1986
Courtesy: William Pitt Sotheby's Int'l
View additional info

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.

Beds:
4
Baths:
4.00
Sq.Ft.:
4,102
Status:
Active
MLS#:
170141423
Type:
Single Family
Subdivision:
N/A
Lot size:
2.67 Acres
Year built:
1999
Courtesy: Coldwell Banker Residential Br
View additional info

Cedar Lake area Contemporary style home privately nestled in the pines on a landscaped 2.67 acre lot. Built in 1999 and renovated in 2015/17 with new roofs, new solar power, new Geothermal heating and a fabulous appx. 1000 sq ft one bedroom first floor level in-law suite with own kitchen, living room, deck, garden area, laundry, and full bath. Freshly painted exterior. Home must be seen to be truly appreciated. Beautiful wood floors, central air, central vac, 4 bathrooms, light and airy open flow. 3 fireplaces including one in the master bedroom which also has a private terrace. You will love the year round sunroom and the spacious wrap around deck. The pool is privately situated on top of a sunny hill with a fire-pit area patio area. Utility bills are extremely low for a 4000 plus sq ft home!

Beds:
4
Baths:
5.00
Sq.Ft.:
4,051
Status:
Active
MLS#:
170140350
Type:
Single Family
Subdivision:
N/A
Lot size:
1.01 Acres
Year built:
1987
Courtesy: William Pitt Sotheby's Int'l
View additional info

One of Chester's finest homes is majestically sited with striking views of the CT River, the Hills of Lyme and expansive valley views. An absolutely immaculate home along with meticulously manicured grounds of lush lawns and gardens favor a peaceful feeling of serenity. Extraordinary quality throughout, custom designs and details have all been carefully selected, custom moldings, and cabinetry throughout the kitchen, the baths and the closets. This home is flooded with natural light, facing Northeast allowing for the magical views of the morning sunrise. The master bedroom en-suite includes a gorgeous stone gas fireplace and access to a private deck, a perfect way to start and end the day. Dine in the chefs kitchen, with all high-end appliances Sub Zero, Bosch, Viking and Wolf, granite counters, tumbled marble back splash and a wine cooler. The 3rd floor is adaptable in many ways from a guest suite with full bath and walk in closet with chandelier lighting to a game room or teenage get-away. The first floor family room is perfect for Sunday football games & movie nights with surround sound, gas fireplace and large windows. Outdoor dining on the large wraparound Trex deck, the stone paver patio or the gazebo while enjoying the impressive and breathtaking views is nothing short of stunning or at the end of the day take a leisurely stroll into town and dine at some of CT Shoreline's best ranked restaurants.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,304
Status:
Active
MLS#:
170133909
Type:
Single Family
Subdivision:
N/A
Lot size:
0.55 Acres
Year built:
1973
Courtesy: Joyce Co. Hill & Harbor, Inc.
View additional info

Call this one HOME! Set nicely on a .50 acre open lot in a subdivision has many improvements. Inviting living room is complimented by the fieldstone fireplace. The newer high end kitchen appliances just make the kitchen shine. Convenient breakfast bar plus the dining area. Step thru the sliders to the deck overlooking the large backyard. Great spot for outdoor living and entertaining. New stairs surrounded by raised paneling that continues down the hallway of the second floor that includes three bedrooms. The full bath offers a custom built double sink vanity and all new fixtures with a tile floor. Beautiful hardwood floors complete the upper level. The lower offers a walkout basement with a door to the to the driveway. Laundry is located on this level. Plenty of space for storage-great potential to add additional finished living space. Another set of stairs from there leads to more basement area which house the mechanicals. Presently serves a great workshop area. So many improvements to list, Complete new roof 2018 ($18,000). The lot offers a wonderful area for the avid gardener. Lots of sunshine! Short drive to the Chester ferry, center of the village and Cedar Lake. Plenty of special activities in the heart of the center of Chester. A must to preview this property.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,374
Status:
Active
MLS#:
170137937
Type:
Single Family
Subdivision:
N/A
Lot size:
1.49 Acres
Year built:
1900
Courtesy: REMAX Valley Shore Genovali RE
View additional info

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,726
Status:
Active
MLS#:
170126301
Type:
Single Family
Subdivision:
N/A
Lot size:
1.4 Acres
Year built:
1815
Courtesy: William Pitt Sotheby's Int'l
View additional info

The Historic P Watrous House Circa 1815 is located in the lovely Village of Chester,CT. With a bit of TLC this home and barn (studio/guesthouse) can be brought back to the magnificent condition it once was. The previous owners were a prominent Attorney, Historian and Author and his wife who was also an active Historian and the Managing Editor of Antiques Magazine, a prestigious position she held for many years. Majestically situated on a quiet road near the lively Chester Downtown Center this was not only a home for "pillars of the community" but was a gathering place for many Historical Society and political events. Imagine living in this stately historic 10+ room Center Chimney Colonial with it's original fireplaces and beautiful wideboard floors. A special feature is a one of a kind, unique elevator located in a later addition to the home. The house has a versatile floor plan with first floor Master Bedroom and 3 Baths. In addition to the home the property includes a Classic Post and Beam Barn/Studio/Guest House with two levels, kitchen and bath (1068 sq ft) and a 2 car garage under. Ideally located on 1.4 partially wooded acres this rare "Historic Treasure" can be yours!

Beds:
3
Baths:
5.00
Sq.Ft.:
3,031
Status:
Active
MLS#:
170134601
Type:
Single Family
Subdivision:
N/A
Lot size:
0.91 Acres
Year built:
1986
Courtesy: William Pitt Sotheby's Int'l
View additional info

'The Bow House' is a captivating waterfront dream house set steps from bustling Chester village, yet a world apart! Perched just above Jennings Pond, you will enjoy views of the pond, waterfall and your dock; from which you can launch your kayak, canoe or SUP. Soaring ceilings, Palladian and custom windows allow light and views to cascade throughout. Water view deck outside the kitchen. French doors in the master suite open to a balcony with commanding views of the pond. This charming 3,000SF bowed-roof Cape with attached two-story "barn" living area offers three bedrooms, four full plus one-half baths, three Rumford fireplaces and a newly remodeled upscale kitchen with custom cabinetry, Wolf and Subzero appliances. It's hard to imagine a more romantic setting or active lifestyle available between water activities, privacy and stone's throw proximity to village shops, restaurants,first-rate Norman Terris Theatre, galleries and the area's best farmer's market. The pondside gazebo is a great place to laze away the day with a good book. Artists will find a first floor study perfect for use as a studio. Amenities include a three bay garage, workshop and whole house standby generator. Brick walkways and stone walls grace the spacious just under an acre grounds. Located a little over two hours from NYC or Boston.This could be the weekend get-a-way in the quintessential quaint eclectic village you've dreamed of; or an invitation to live like you're on vacation every day!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,582
Status:
Active
MLS#:
170131816
Type:
Single Family
Subdivision:
N/A
Lot size:
2.39 Acres
Year built:
1996
Courtesy: William Raveis Real Estate
View additional info

More For Your Comfort, Convenience and Money! The home awaits someone who wants to fill its large porch with a swing or rocking chairs and a welcome mat that says something witty. The Colonial is move-in ready awaiting someone to fill its space with their own personal touches. Gleaming hardwood floors are throughout the house; kitchen boasts high top corian counters, cozy family room with gas fireplace and a master suite with bonus room. This home also features a new roof and new siding installed past two years. Off the back porch, you have an ideal level backyard, perhaps for the world's best backyard soccer field or for someone who loves to watch the deer prancing through. This home is near the river and close enough to the charming village of Chester. Never been to Chester? It's a perfect enclave of artists, cozy restaurants and a village stacked with cute nostalgic homes.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,452
Status:
Active
MLS#:
170084968
Type:
Single Family
Subdivision:
N/A
Lot size:
9.2 Acres
Year built:
1850
Courtesy: Berkshire Hathaway NE Prop.
View additional info

Beautiful Chester Retreat ready for the next Steward! The stately R.H. Webb Estate circa 1850 is a Currier and Ives postcard of New England with all the charm and graciousness of the period, but designed for today! The focal point of the property is a handsome Colonial sited proudly amongst the mature Sugar Maples and offers some of the most spectacular views of Gillette's Castle and the beautiful Connecticut River Valley atop the rolling meadows. Perfect for the gentleman farmer or anyone who enjoys over 9 acres of privacy so close to the quaint village of Chester. The home features the reclaimed original wide board floors, exposed beams in the vaulted Keeping room that opens to the designer kitchen with a breakfast island. The first floor continues to a combined formal living and dining area anchored by a lovely wood burning fireplace, a front entry parlor as well as the library. The second story has 3 charming bedrooms filled with nooks and cranny's you would expect to find in a period home, but with new skylights to bring in natural light. The detached Carriage House is a wonderful surprise that features a 2 bay garage area, a 1000 gallon septic system as well as 1776 square feet of beautifully finished space with a full bath, a finished bonus room, and a private balcony with full views of Gillette's Castle. Perfect for a home business or overflow guests. Come discover the charm that is historic Chester!

Beds:
5
Baths:
4.00
Sq.Ft.:
3,267
Status:
Active
MLS#:
170121383
Type:
Single Family
Subdivision:
N/A
Lot size:
3.64 Acres
Year built:
1971
Courtesy: William Pitt Sotheby's Int'l
View additional info

An exciting open and bright contemporary offering both a first floor master suite and spacious first floor office. This custom home features vaulted ceilings and walls of windows, creating a bright environment with just the right balance of cozy and open spaces. The separate one bedroom "cottage" creates a perfect opportunity for multi-generational living, guest use; or as a legal rental to generate income. Set on over 3.64 acres abutting nature conservancy for added privacy. Room for expansion or to add another building on the property. Just a short drive to beloved charming Chester village shops, restaurants and galleries. Minutes to marinas, yacht clubs, the CT River and Long Island Sound. The quintessential New England experience just a little over two hours from New York City and Boston.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,880
Status:
Active
MLS#:
170119584
Type:
Single Family
Subdivision:
N/A
Lot size:
0.65 Acres
Year built:
1986
Courtesy: William Pitt Sotheby's Int'l
View additional info

Stroll to Chester Village from this Greek Revival Colonial with its dramatic two story foyer and sweeping staircase. The home features a remodeled kitchen, 9 foot ceilings and three fireplaces. The large second floor landing boasts a balcony and palladium windows that provides a flexible space perfect for a sitting area, office nook and gallery. Chester is situated in the heart of the Lower Connecticut Valley and is renowned for its quaint village featuring unique shops, numerous galleries and diverse restaurants. Chester is only two and one half hours away by car from both New York City and Boston as well as an easy commute to Hartford, New Haven and New London. Do not miss this opportunity to call Chester home!

Beds:
3
Baths:
1.00
Sq.Ft.:
1,890
Status:
Active
MLS#:
170120440
Type:
Single Family
Subdivision:
N/A
Lot size:
13.72 Acres
Year built:
1972
Courtesy: Innovative Properties
View additional info

164 W Main St, Chester, CT is a single family home that contains 1,890 sq ft. & was built by the owner in 1972, also included 13 Acres of land... 3 bedrooms , 1 bathroom, 2 fireplaces, 2 car attached garage. NEEDS TLC

Beds:
3
Baths:
3.00
Sq.Ft.:
2,461
Status:
Active
MLS#:
170107482
Type:
Single Family
Subdivision:
N/A
Lot size:
6 Acres
Year built:
1987
Courtesy: William Pitt Sotheby's Int'l
View additional info

The charming Colonial sits on a tranquil hillside with over six acres of open fields, a large wildflower meadow, and a pond. The property has been featured in local garden tours. Walk to the front of house, up the field stone steps that lead you to the stone patio with perennial flowers overlooking the beautiful property. The main floor is comprised of a Kitchen with Breakfast area, Corian countertops, sit-at-center-island, gas cook-top, custom cabinets, chestnut floors and was remodeled in 2017. French doors open out to a full length porch with views of the open field, flower meadow and pond. The Living room has a fireplace and a formal Dining room has custom built-ins. The mud room connects to the bright workshop/artist studio, which has three sides of windows. The Master Suite is on the second floor overlooking the pond, and includes a sitting room with a large size dressing room, full Bath, Laundry and a spacious Office with built-ins. The lower level includes two Bedrooms, a full Bath and a sitting room. There is French door access to the outside patio and gardens from this level. Solar panels installed by Aegis have supplied all of the electricity for this house. There is a 10 kW whole house automatic standby generator fueled by propane. A separate guesthouse is included on the property; with its current rent, it can pay 1/3 of your mortgage.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,000
Status:
Active
MLS#:
170103868
Type:
Single Family
Subdivision:
N/A
Lot size:
2.04 Acres
Year built:
1998
Courtesy: Realmart Realty
View additional info

Wonderfully appointed home loaded with all amenities. Home fully updated within last 4 years . All major upgrades done. House will sell itself, bring your buyers in. One of the most desirable locations in town. Walking distance to CT River, Chester center and state forest trails . Adjacent building lot also available as a separate listing and separate price.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,000
Status:
Active
MLS#:
170087589
Type:
Single Family
Subdivision:
N/A
Lot size:
1.2 Acres
Year built:
2018
Courtesy: Berkshire Hathaway NE Prop.
View additional info

BUILD A CUSTOM HOME ON THE WATER FOR ABOUT $699K including the land! ENJOY WATERFRONT LIVING on one of the last building lots on the Connecticut River and award winning Connecticut Valley Homes can economically design/build the size and style home you want. CVH's estimate for a 2000 SF 3 bedrooms/2 bath home is only $371,000 or use your own builder. This level private location has beautiful views across the river of Gillette's Castle State Park in a group of upscale homes with electric and road already to the site. It is cleared, perc'd, with a boat launch and swimming area. Build you own dock or stroll over to your boat at the private marina. An engineered site plan has already been done and approved by ZBA which shows where the home can to be placed on the lot, septic, well, etc.. and the living space is elevated over the large garage/covered parking to meet current FEMA requirements so you could enjoy a substantial annual insurance savings. Agent/Owner

Beds:
4
Baths:
3.00
Sq.Ft.:
2,758
Status:
Active
MLS#:
170096296
Type:
Single Family
Subdivision:
N/A
Lot size:
3.86 Acres
Year built:
1860
Courtesy: William Pitt Sotheby's Int'l
View additional info

Looking for a home with room for everyone.... this is it! This circa 1860 stately country estate, rich in history, sits on 2+ acres with sweeping lawn and serene views. This listing includes a 1.58 acre additional lot abutting this property in this price. The main house has 3 bdrms, 3 baths plus an inlaw suite. It also features an updated 2 bdrm, 2 bath carriage house apartment in the adjacent 3 car garage, and currently offers additional income, making this property attractive to the savvy buyer. Skylights fill this space with light, with it's new kitchen, it's a delight. In the main house the in-law suite renovated in 2014, has a private entrance and full bath. The master suite was lovingly updated in 2008, which includes a sitting area to retreat to, large bath and stunning closet/dressing area. The renovated kitchen includes a butler's pantry and is steps from the large enclosed screen porch for dining and enjoyment. Also, an additional 1.58 acre building lot is being offered at $109,000. Imagine being a short walk to Chester Village filled with fine restaurants, coffee shops, the area's most robust farmer's market, shops, theater and galleries. Make this village country estate your home and write the next chapter of the most "Story'd home in Chester."

Beds:
4
Baths:
3.00
Sq.Ft.:
2,758
Status:
Active
MLS#:
170096283
Type:
Single Family
Subdivision:
N/A
Lot size:
2.28 Acres
Year built:
1860
Courtesy: William Pitt Sotheby's Int'l
View additional info

Looking for a home with room for everyone.... this is it! This circa 1860 stately country estate, rich in history, sits on 2+ acres with sweeping lawn and serene views. The main house has 3 bdrms, 3 baths plus an inlaw suite. It also features an updated 2 bdrm, 2 bath carriage house apartment in the adjacent 3 car garage, and currently offers additional income, making this property attractive to the savvy buyer. Skylights fill this space with light, with it's new kitchen, it's a delight. In the main house the in-law suite renovated in 2014, has a private entrance and full bath. The master suite was lovingly updated in 2008, which includes a sitting area to retreat to, large bath and stunning closet/dressing area. The renovated kitchen includes a butler's pantry and is steps from the large enclosed screen porch for dining and enjoyment. Also, an additional 1.58 acre building lot is being offered at $109,000. Imagine being a short walk to Chester Village filled with fine restaurants, coffee shops, the area's most robust farmer's market, shops,theater and galleries. Make this village country estate your home and write the next chapter of the most "Story'd home in Chester."

Beds:
4
Baths:
4.00
Sq.Ft.:
3,307
Status:
Active
MLS#:
170092064
Type:
Single Family
Subdivision:
N/A
Lot size:
4.1 Acres
Year built:
2018
Courtesy: Williams Realty Services
View additional info

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

Beds:
5
Baths:
7.00
Sq.Ft.:
6,054
Status:
Active
MLS#:
170053745
Type:
Single Family
Subdivision:
N/A
Lot size:
2.75 Acres
Year built:
1997
Courtesy: William Pitt Sotheby's Int'l
View additional info

Designed for the ultimate in one level living, this superb home was completely renovated with the finest craftsmanship in 2004, all while restoring and preserving the historical elements. A bright open Kitchen, with an informal dining area, has high coffered ceilings and every modern convenience a discerning chef could desire; two Bosch dishwashers, Wolf double ovens and wine cooler. Counters are black granite and sit down Center Island has a gas cook top. Cabinets are in rich cherry wood. Adjacent is a 1,500 sqft Living room with the original high wood barrel ceiling and large stone fireplace. For those with a flair of performing, there is an antique raised stage with hand painted backdrops and an antique bowling alley. A surround sound system throughout, the home is state-of-the-art, as is Lutron lighting. The elegant Master Bedroom Suite, also with a high barrel ceiling has recessed lighting, a stone propane fireplace and radiant heated floors. French doors lead out to the stone patio surrounding the Gunite heated pool and hot tub. The luxurious Master bath features an oversize Roman tub, tiled shower, granite counters with twin basins and a room size walk-in closet. Four additional bedrooms, each designed with unique themes, all have radiant heated floors. Above the three car garage is an in-law apartment with a full Kitchen. This fabulous home is only a short distance to Chester, one of the most charming and picturesque towns in Connecticut.

Beds:
4
Baths:
7.00
Sq.Ft.:
6,350
Status:
Active
MLS#:
N10223217
Type:
Single Family
Subdivision:
N/A
Lot size:
5.86 Acres
Year built:
2007
Courtesy: Coldwell Banker Residential Br
View additional info

Vermont in Connecticut! This timeless gem boosts a large first floor master-suite with private terrace and 4 additional bedrooms. Situated nicely on over 4 acres - the home is a 6200+ sq ft masterpiece built in 2007 with a focus on casual luxury living. Features include: Cedar shingle shake siding (treated), music room, large office, massive 1600+ sq ft walk-out lower level media/entertainment room, five full bathrooms & two half bathrooms, gym, wine cellar, and a 3 car garage . Minutes to the historic village of Chester which is vibrant with shopping, restaurants, local bazaars, and fairs. Close to Chester Airport, Cedar Lake and major commuting routes.

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This Information is from Smart MLS and has been compiled from various sources, all of which may not be completely accurate. Smart MLS makes no warranty or representation as to the accuracy of listing information. All information that influences a decision to purchase a listed property should be independently verified by the purchaser. Copyright 2017 Smart MLS, Inc. All rights reserved.

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