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luxury real estate for sale Chester, United States

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Property 1
Contract pending
45

Property Chester (United States)

Welcome to this magnificent colonial-style residence nestled in the picturesque town of Chester, CT, a haven for boating enthusiasts and those who appreciate the serene beauty of the Connecticut River. This expansive home is a perfect blend of classic charm and modern luxury, offering an exceptional living experience. As you step inside, you are greeted by an elegant foyer that sets the tone for the rest of the home. The heart of this residence is undoubtedly the chef's kitchen, a culinary dream featuring top-of-the-line appliances, oversized island and tons of natural sunlight. Whether hosting celebrations or intimate gatherings, the kitchen flows seamlessly into the formal dining area and living spaces, making entertaining a breeze. The home boasts generous living areas with plenty of natural light, accentuating the rich hardwood floors that run throughout. The traditional colonial layout includes spacious bedrooms, providing a private and tranquil retreat for family and guests. The finished basement is a bonus flex space. Outside enjoy the patio and hot tub. The proximity to the Connecticut River is a boater's dream, with easy access to marinas and waterways for endless aquatic adventures. This home is not just a residence but a lifestyle offering comfort, elegance, and the perfect setting for creating lasting memories. Experience the best of living in Chester and their amazing downtown filled with restaurants and shops.

$1,050,000
4bedrooms
4bathrooms
land  2.1ha

By William Pitt Sotheby's International Realty

House 2
Contract pending
31

House Chester (United States)

Step into a bygone era with this authentic bungalow home, a true gem that's poised for its second act. Brimming with original woodwork, period lighting, and classic architectural details, this residence is a rare find for the enthusiast of vintage charm. Greeted by an expansive front porch, envision leisurely afternoons and evenings spent enjoying the outdoors enjoying the view of Jennings Pond, a nod to the home's timeless appeal. Inside, the original woodwork and period lighting fixtures transport you to a different time, offering a sense of history and craftsmanship that's increasingly hard to find. The home features a dining room, generous front-to-back living room with a fireplace, providing a versatile space for relaxation and entertainment, complemented by the warmth of its original features. The kitchen, complete with a traditional pantry, awaits your vision to modernize while honoring the home's storied past. The second floor provides 4 sizable bedrooms with ample storage, an additional lounge area with sunshine beaming through the generously sized windows, and a half bath. Set on a sizable wooded lot, close to the downtown Chester shopping district, the yard offers privacy and the potential for creating a garden oasis or a natural playground for adventure. This original bungalow is an invitation to preserve a piece of history while infusing it with new life. It's perfect for those who cherish authenticity and dream of crafting a home in a sought after are

$379,900
4bedrooms
2bathrooms
land  4,452

By William Pitt Sotheby's International Realty

Property 3
35

Property Chester (United States)

Welcome to 9 Old County Road in picturesque Chester. This 4 bedroom, 3.5 bath home is nestled atop a quiet 5 home cul-de-sac. You will fall in love as you pull into the driveway, admire the perfect balance of privacy and community. A newer front door with transom and sidelites welcomes you and warms the entryway with light. The main floor offers both living room and family room, a formal dining room and eat in chef's kitchen. The well-appointed kitchen with abundant counter space, storage and cabinetry, sub zero fridge and Miele appliances; it's any home chef's dream. This area is the entertainment heart of the home as it opens up to the dining room and the family room with wood floor and focal point fireplace. This space is surrounded by over-sized sliders on all sides making for a sunfilled and calming space for guests and just everyday life. The first floor also transitions to a 1 bedroom in law, office or guest space that is secure and with own entrance. Home also features custom mudroom & pantry, new whole house generator, a flex space bonus room and new windows on both 1st and 2nd floor. Over 4000 sq ft of space but feels both sprawling and intimate at the same time. A conveniently located detached, deep 4 car garage is also located on this over 5 acre lot. The backyard space is large and flat while lined with mature trees for privacy and shade. All this minutes from charming downtown Chester, renowned for its arts scene, dining and quintessential NE experience.

$849,000
4bedrooms
4bathrooms
land  2.2ha

By William Pitt Sotheby's International Realty

136 listings near Chester

House 1
Nearby
40
Video

House Lyme (United States)

Perched atop the hills of Lyme, 44 Ferry Road stands as a beacon of luxury and refinement. This 5-bedroom, 5.5 bathroom estate is masterfully sited on 40 acres of picturesque terrain with stunning 360 degree views. Here, you will discover a retreat that blends privacy, tranquility, and the natural beauty of the Connecticut River, coves, and countryside. The main residence spans over 6,500 square feet of thoughtfully designed living space. A detached guest house adds 1,500 square feet, including an office or bedroom, a full bath, and a kitchenette. An impressive solar array reflects a commitment to environmental stewardship. Natural splendor calls from a private pond, massive rock formations, and the Lyme Preserves hiking network, which connects directly to the property. With expansive acreage, the potential to develop an equestrian paradise is within easy reach if desired. This estate is a rare offering that invites you to enjoy the pinnacle of Connecticut River Valley living, within a comfortable two-hour drive from Boston and Manhattan.

$3,700,000
5bedrooms
6bathrooms
land  16.2ha

By William Pitt Sotheby's International Realty

House 2
Nearby
Contract pending
37

House Deep River (United States)

Natures paradise! Wonderful custom-built home designed by one of the renowned Centerbrook Architects nestled near mature trees next to a land trust property. This home was exceptionally sited to take full advantage of a lovely natural and extremely private setting. No detail was missed to obtain the most benefit from natural light and surroundings. The home flows seamlessly from kitchen to dining room, to living room, reading nook, and sunroom. The first floor also features a bedroom and a full bath. Upstairs, the primary bedroom with ensuite bath is separated from the other rooms by a library, study/office to allow for privacy for all. The almost 5 acre parcel is nothing short of a birders paradise, and abuts the Florence Bidwell Sanctuary Deep River Land Trust. The property also has a patio, deck, two car detached garage, and some trails. A rare find with proximity to Deep River, Essex and Chester villages for shops, restaurants, art galleries and more.

$859,900
3bedrooms
3bathrooms
land  2ha

By William Pitt Sotheby's International Realty

Land 3
Nearby
6

Land Deep River (United States)

1.58 acre parcel offering tremendous Northly & Southerly CT River Views from high above!

$275,000
6,394

By William Pitt Sotheby's International Realty

House 4
Nearby
Contract pending
26
Video

House Deep River (United States)

This fabulous property is bursting with character, charm and is completely unique with a stunning farm stand that has proven great income potential. Grow your own produce and fill the stand with the farm's bounty. It's an amazing opportunity. Enjoy the almost 16 acres of farmland that boasts two ponds and the Deep River that runs right through the parcel. Horses, livestock, chickens, thrive in this environment. Complete with a glamping tent by the river, a platform for live music and even a brigade of ride on toy tractors. The massive barn is a wonderful feature on this property, a two story open barn is a fantastic place to entertain a large group or house animals. The farmhouse has been renovated and is quite cozy. The tractor shed could house all of your grown up toys and tools or could be turned into a nice she-shed! Take walks around the ponds, watch the sunrise and sunset, drink coffee then later cocktails or even enjoy a Farmcicle on adirondack chairs by the water. There are endless possibilities here at the Deep River Farm - a place which has quite a following, not to mention great swag - the Farmstand and Farmcicle were always bustling with weekenders and locals alike and definitely missed. Surrounded by other farms, it is also very convenient to town and to Route 9. Half way in between Boston and New York, (around 2 hours to each) it couldn't be a more convenient spot for weekenders that love a great destination farm. Schedule a tour and see it's beauty!

$995,000
3bedrooms
1bathroom
land  6.4ha

By William Pitt Sotheby's International Realty

House 5
Nearby
40

House Lyme (United States)

This charming, 2002 custom built, 3394 sqft contemporary cape on 6.25 woodland acres is quintessential Lyme living. A 4 bd/3 bth home for all seasons with a covered open porch that welcomes you home. The southern view features 2 granite patios, a screen porch, perennial gardens, a beautiful reflecting pond, all surrounded with granite outcroppings and mountain laurel. We all love nature, but not in our gardens! This property has a 6 ft high mesh fencing that surrounds the yard and gardens keeping natures critters at bay. Inside this beautiful home you will find 9ft+ ceiling heights along with vaulted ceilings in the primary suite and craft room. Custom details throughout such as a Limestone fireplace, built in bookcases, pocket doors, and a custom brick fireplace that adds warmth to the kitchen area. Maple floors are found on the main level and 2nd fl too. A stunning cooks kitchen with large island, pantry, and the smart floorplan is open to the brick fireplace gathering area and informal dining area. In the connector, you will find the laundry room, and office with full bath, and a bright windowed foyer that leads you to the 2 car garage. There are an additional 2 bedrooms and bath on the 2nd floor and storage closets galore. This is Elegant 1st floor living with room for guests above. Although this parcel is a natures paradise, nearby is the entrance to the Hadlyme Hills Preserves part of the Lyme Land Trust. Lace up your boots, this is the best of Lyme.

$995,000
4bedrooms
3bathrooms
land  2.5ha

By William Pitt Sotheby's International Realty

House 6
Nearby
Contract pending
16

House Deep River (United States)

This property boasts a wonderful 5 acre pasture right along the Deep River. The home could use some updating, but it is very clean and move in ready. This would make a great weekend home it would also be great for raising animals. Surrounded by farmland this area of Deep River is adjacent to many other farms and yet it is convenient to Route 9 and the lovely downtown shops. Come take a look and see where your vision takes you!

$450,000
4bedrooms
2bathrooms
land  2.1ha

By William Pitt Sotheby's International Realty

House 7
Nearby
33

House Lyme (United States)

Discover elegant country living in this 4600 SF Colonial home nestled on 3-acres overlooking nature's beauty. This property offers a first floor primary bedroom suite which includes a cozy fireplace for tranquil evenings along with dual walk-in closets. The large primary bath is an oasis of relaxation, featuring a jetted soaking tub, double vanities along with walk-in tiled shower. Entertain with grace in the living room, where two-story windows fill the room with natural light, and gleaming cherry hardwood floors reflect the home's attention to detail and design. A gourmet kitchen awaits the discerning chef, boasting cherry cabinets, built in china hutch, and center island, making meal preparation and entertaining a joy. Extend your entertaining outdoors to the 90 foot deck overlooking the natural landscape of the back yard. A luminous sunroom, with soaring windows and three sets of French doors, ensure a seamless connection with nature. Upstairs, three bedrooms offer comfort and privacy for family and guests alike. This home is a testament to a thoughtful layout that caters to both grand entertaining and intimate gatherings. The 3,000 SF finished walkout lower-level with full bath offers limitless possibilities. Easy to maintain yard with fenced area. Home built and owned by original owner of 18 years. 15 minutes to major shopping and I-95, 2 mins to Hadlyme market. 5+/- miles to restaurants, golf and opera house. Half way between Boston and New York.

$1,150,000
3bedrooms
5bathrooms
land  1.2ha

By William Pitt Sotheby's International Realty

House 8
Nearby
37

House Essex (United States)

Retreat to an enchanting home set on 1.51 acres atop a quiet, private cul-de-sac minutes from Essex village and the CT River. Combining timeless New England charm with expansive vistas and modern comforts, and offering the perfect sanctuary for those seeking tranquility and elegance. Fresh paint and recently refinished hardwood floors throughout. With 4,714 SF,(not including the 650 SF walk-out lower level one-bedroom apartment with a family room, fireplace, and kitchenette), this residence boasts 4 bedrooms, four full baths, plus two powder rooms. The first-floor primary suite offers direct access to a wrap-around deck. Newly remodeled ensuite bath in the well-appointed second-floor primary suite. The soaring two-story vaulted ceiling and stone fireplace in the family room perfectly complement the formal dining room, and living room with fireplace and wet bar. One of the favorite spots in this home is the screened porch set above the lush landscaped grounds. The spacious eat-in kitchen has a vaulted beadboard ceiling and opens to a serene bluestone terrace and garden oasis. Amenities include a three-bay garage, workshop, multiple office options, new furnace and air conditioning systems, a long private driveway, and glimpses of the CT River. If quiet, privacy, and elbow room are on your wish list, wish no longer. Located in the quaint town of Essex, rich in maritime history. Enjoy waterfront restaurants, shops, marinas, and nearby cultural venues. Live your Essex dreams here!

$1,395,000
4bedrooms
6bathrooms
land  6,111

By William Pitt Sotheby's International Realty

House 9
Nearby
36

House Essex (United States)

This home is a must see if you are looking for a custom-built colonial with a contemporary flair! Not a detail was spared in this gorgeous property which sits high above the CT River - only two hours from NYC or Boston via car or train. The true chefs kitchen opens to a spacious family room with 30' ceilings warmed by a granite encased fireplace. The open floor plan is completed by a beautiful dining area and custom designed dry bar. The spacious first floor ensuite has a full bath and generous walk in closet. A formal sitting room or office finishes out the mahogany floored main living space. Follow the curved staircase up to a breathtaking owner's suite with seasonal views of the CT River. The spa-like bathroom includes a 15-foot-long open shower, soap stone soaking tub and towel warmer rack. Two more spacious bedrooms, a full bath and oversized laundry room complete the second floor. The 930SF walkout lower level has an impressive custom-made wet bar, living room, half bath and a state of the art two-room recording studio which could easily be used for office space, workout room, etc. Step outside to enjoy 1000SF of front and back porch space that overlooks extensive lush landscaping. The property abuts Essex Land Trust with acres of walking trails. This custom made, builder-designed home is virtually maintenance free with Geothermal heat, tankless hot water heater, foam insulated interior walls and hardy board siding. Come see this beautiful home that is turn key ready!

$1,449,000
4bedrooms
5bathrooms
land  8,013

By William Pitt Sotheby's International Realty

Land 10
Nearby
18

Land East Haddam (United States)

Rarely do you find a village residential lot, in a lovely subdivision, walking distance to the Goodspeed Theater, Library, Coffee Shop, restaurants, and the Connecticut River. Even better we have two lots to show you! This one sit up on a knoll with peek a boo seasonal views of the Connecticut River, 2.06 acres, plus an additional .11 acre piece across the lane that will be included with this sale. The lot is lightly wooded with a rolling terrain. Utilities are at the street and this lot can now hook up to the city sewer. Lot 4 borders this lot with it Cul de sac location. This oasis is so convenient to Rt 9 for easy commuting routes. Come and view this special spot tucked up above the village, bring your plans and build your dream home.

$139,000
8,337

By William Pitt Sotheby's International Realty

Land 11
Nearby
18

Land East Haddam (United States)

Rarely do you find a village residential lot, in a lovely subdivision, walking distance to the Goodspeed Theater, Library, Coffee Shop, restaurants, and the Connecticut River. Even better we have two lots to show you! This one is on a quiet cul de sac, 1.67 acres, plus an additional .55 acre piece across the lane that will be included with this sale. The lot is lightly wooded with a rolling terrain. Utilities are at the street and this lot can now hook up to the city sewer. Lot 6 borders this lot with it's winter peek a boo views of the Connectiut River. Come and view this special spot tucked up above the village, bring your plans and build your dream home.

$139,000
6,758

By William Pitt Sotheby's International Realty

Property 12
Nearby
33
Video

Property East Haddam (United States)

Immerse yourself in breathtaking views of the Connecticut River from the comfort of your own home. This classic Greek Revival c.1840 home offers lovingly restored interiors throughout, beautiful light, and lush landscaping and gardens. Off the foyer is the formal living room with pocket doors and original moldings. The dining room is window lined and works for both formal and casual dining. The kitchen offers timeless beauty with solid cherry wood cabinets, stainless steel appliances and subway tile backsplash. The main floor also has an elegant and generously sized family room with wood burning fireplace and views on three sides. French doors open up to the covered back porch with solid mahogany decking, river and garden views. Dine al fresco while watching beautiful sunsets over the River. The 2nd floor holds 3 bedrooms including a luxurious primary with river views and an updated en suite bath with radiant heat, marble flooring, Waterworks soaking tub and a separate shower. The upper level is a versatile bonus space with a half bath that could be a guest room or home office. Entertain year round in the garden level sun room which opens to the back yard and walled garden with water feature. Unique to this home is a 540 square foot summer cottage with a wall of windows overlooking the river. It is a stunning entertaining space with wood burning fireplace. The river frontage is steep but could accommodate a boat lift or dock. This home really has it all!!

$1,400,000
3bedrooms
3bathrooms
land  5,625

By William Pitt Sotheby's International Realty

Land 13
Nearby
Contract pending
12

Land Essex (United States)

This lush building lot once a short game golf course is now made available for you to build on taking advantage of the wonderful surrounding landscape and proximity to Essex Village. Gorgeous landscape, amazing surroundings and short distance to all Essex Village offers. Gorgeous lot ready for you to build the home of your dreams!

$349,900
6,192

By William Pitt Sotheby's International Realty

House 14
Nearby
Contract pending
29

House Essex (United States)

You could be the third lucky person to own this property. This 1590 square ft, split-level ranch, welcomes you the moment you cross the threshold. The living room has a stone fireplace for cozy evenings and flows into the dining room with a modern chandelier. There are hardwood floors in both of these rooms. The kitchen has new (Dec. 2023) stainless-steel appliances, granite countertops and plenty of storage. The 3-season sunroom, 240 sq ft not represented in the square foot totals, is the bright star of the first floor with three walls of sliders, so you can see all that the backyard has to offer: stone patio, firepit and mature trees and flowers or to relax and enjoy a casual dinner or glass of wine. The three bedrooms, all with hardwood floors, provide plenty of options, especially if you need a home office or guest rooms. The hall bathroom was remodeled in July 2023 including tile floor, double vanity, new tub and tile surround as well as all new lighting, fixtures and window. The primary bedroom is large with two closets, carpeted floor but there is hardwood underneath and a master bath. The family room boasts a new luxury vinyl wood floor, built in bookshelves and south facing windows to keep everything light and bright. From the family room, walk out directly onto a stone patio which overlooks the large level yard. The lawn between the patio and stairs from the sunroom is awaiting sod as the pipe from the septic tank was recently replaced: March 2024,

$569,000
3bedrooms
2bathrooms
land  3,440

By William Pitt Sotheby's International Realty

Property 15
Nearby
41

Property Essex (United States)

This charming home in Essex Village offers a perfect combination of comfort and elegance. Located on a picturesque street just steps away from Main Street and the Connecticut River, this timeless residence has undergone meticulous renovations over the years. Features include wide-plank cherry hardwood floors and French doors that open to a professionally landscaped backyard, one of the finest in Essex Village. The expansive living room offers a propane fired fireplace and the family room is ideal for gatherings, the beautiful wood burning fireplace will keep you warm in the chilly months, while the impressive kitchen boasts high-end appliances, granite countertops, and a separate pantry. The open floor plan and generously sized rooms create a welcoming atmosphere, enhanced by a wrap-around blue stone patio for outdoor dining. The master suite is luxurious with a fireplace and beautiful marble mantel, balcony, walk-in closet, and private bath for a peaceful retreat. A first-floor study with a full bathroom and closet could easily serve as a guest room. Enjoy morning coffee on the front porch while taking in distant views of the CT River. The professionally landscaped yard with a waterfall adds to the beauty of the backyard. This home is a perfect blend of comfort and style, making it a truly exceptional property in Essex Village.

$1,250,000
4bedrooms
3bathrooms
land  1,416

By William Pitt Sotheby's International Realty

House 16
Nearby
38

House Essex (United States)

c 1837 - The Theodore Pratt Homestead. This Greek Revival home is one of the most admired homes in Essex. Stately, gracious, elegant and comfortable. From the moment you step inside this home you feel at ease. Updated, loads of natural sunlight, set up on a knoll with seasonal peeks of the Connecticut River. This property as been in the same family for more than 25 years. The first floor offers an updated kitchen with propane fireplace, a primary bedroom suite with a propane fireplace as well, a large comfortable family room, an office and an expansive formal dining room that opens to a bluestone patio. The second floor has three more bedrooms, two bathrooms, a recreation room, and a small office. The three car garage has a breezeway to the kitchen and above the garage is a bonus room with a full bath. This home offers the best of both worlds, quiet, spacious, steeped in history and all Essex Village offers. Restaurants, marinas, shops, galleries, yacht clubs, the world famous Griswold Inn. Essex is approximately 2 hours from NYC and Boston.

$1,925,000
4bedrooms
5bathrooms
land  2,266

By William Pitt Sotheby's International Realty

Property 17
Nearby
Contract pending
38

Property Essex (United States)

This immaculate, delightful, c.1804 Essex Sea Captain's House has been lavished with attention in the form of thoughtful, well-executed additions and updates. One recent addition is a spectacular English Conservatory with radiant-heated tile flooring, overlooking manicured grounds featuring multiple gardens, a brick garden house, and heated pool with separate spa. Above the two-bay garage you will find a spacious office complete with water views. The interior of this home subtly dazzles with details at every turn. Gleaming wide-board floors lead the way to tasteful rooms graced by fireplaces, custom built-ins, fine millwork and a sense the art of living well, lives here! Upstairs, the primary suite is as impressive as it is practical. A barreled ceiling and fireplace set the stage for luxe ambiance enhanced by French doors opening to the mahogany-paneled primary bath and closet/dressing room. A second upstairs bedroom suite adjoins an office/nursery/fitness room with it's own staircase. A bedroom with ensuite bath may be found on the first floor. A 500 bottle wine cellar, walk-out office/media room/ fitness room/studio, storage area, and top-of-the-line mechanical systems, occupy the lower level. Whole house generator and irrigation system. Set on a small, quiet lane, ending at North Cove. Just steps away from Essex village marinas, yacht clubs, shops, restaurants and the CT River. Essex is located mid-way between NYC and Boston. Make this quintessential Essex home yours!

$2,350,000
4bedrooms
4bathrooms
land  1,781

By William Pitt Sotheby's International Realty

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