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47 Ferry Rd, Chester
$1,275,000
3 Beds ⋅ 3 Baths ⋅ 24135466 MLS
A unique offering in Chester on the CT. River in the Pattaconk/Fort Hill area, bordering the Chester ferry. A small historic town known for its Main Street, art galleries, restaurants and hiking in the Cockaponset State Forest. Privately situated, fully remodeled charming colonial home sits above the River overlooking 5+ acres of waterfront meadow landscape. Ferry activity, views of Gillette's Castle and an abundance of nature surround you while fishing or swimming. (Dock access is feasible- refer to attachments.) Home parcel is nicely separated with manicured level grounds surrounding the home and an open lower meadow. (subdivision is feasible or expansion of the family compound.) Discriminating buyers will appreciate the detail and craftmanship in this home offering multi-generational appeal. Versatile and open floorplan, sunny, solid, and welcoming. 3 bay garage with full height and flooring provide great workspace for any hobbyist! Detached barn could be used for a horse of course or boat/recreational storage. The current steward of this home has proudly groomed the gardens/grounds and recently added a greenhouse for your enjoyment. Boiler, roof, kitchen, elec/generator, windows are only a few of the home updates that accompany the grounds. (refer to list of upgrades as an attachment) Immediate occupancy is feasible.

47 Ferry Rd, Chester
19 Denlar Dr, Chester
$1,200,000
2 Beds ⋅ 2 Baths ⋅ 24205746 MLS
Investors take note! Your vision and investment in Chester will be rewarded by adding this Chester, Ct income producing six-unit apartment building to your real estate portfolio. Built in 1972 and owned by one family since 1984, this is a rare opportunity to acquire a property that has been well maintained and has an excellent rental history. In addition to the solid construction and care the property has been given, 19 Denlar Dr benefits from its location in this desirable Connecticut River Valley/Shoreline town and the area's need for quality and affordable rental apartments. The Nature Conservancy named the Lower Connecticut River Valley one of the 40 "Last Great Places." Chester is located 2 hours from both New York and Boston. Amtrak service is available from nearby Old Saybrook and the Shoreline RR connects to Metro North in New Haven. Access to the route 9 corridor allows for quick commuting to Middletown and Hartford.

19 Denlar Dr, Chester
7 Old Depot Rd, Chester
$975,000
4 Beds ⋅ 3 Baths ⋅ 24069434 MLS
Bella Vista: A Timeless Italianate Treasure on 6 Acres. Step into a piece of history, a magnificent Italianate country villa that has graced the landscape since 1908. First time on the market, this storied estate has been lovingly preserved by the same family for generations, a testament to its enduring allure. Listed on the National Registry of Historic Places, Bella Vista is an architectural gem inspired by the quintessential farmhouses of northern Italy. Its grandeur is immediately apparent upon arrival, with six sprawling acres that offer a private and serene hill side retreat yet within a short stroll to Chester center. The European-style open terrace is a highlight, adorned with elegant pergolas inviting leisurely afternoons soaking in the panoramic views. It's the perfect setting for hosting gatherings or simply enjoying the tranquility of your surroundings. Inside, the residence boasts four well-appointed bedrooms, two and a half baths, and an impressive five fireplaces, ensuring a warm and inviting atmosphere throughout the home. Each room is a celebration of the past, with meticulous attention to detail that honors the original design while offering modern comforts. Bella Vista is not just a home; it's a legacy waiting to be continued by those who appreciate the romance and craftsmanship of a bygone era. Embrace the chance to make Bella Vista, your own and carry on the tradition of elegance and sophistication that only a home of this caliber can provide.

7 Old Depot Rd, Chester
136 Goose Hill Rd, Chester
$825,000
4 Beds ⋅ 3 Baths ⋅ 24172811 MLS
Welcome to 136 Goose Hill Rd. This home has been tastefully redesigned inside and out with no expense spared. Featuring 4 bedroom, 3 full bathroom, over 3,300 sq ft of beautifully finished living space sitting on just over 2 acres. Step inside to discover all-new hardwood flooring throughout the main level and a thoughtfully designed open-concept layout ideal for both everyday living and entertaining. At the heart of the home is a spectacular chef's kitchen featuring an oversized island, quartz counters, stainless steel appliances, custom wet bar area, formal dining space, and inviting sitting area. Just beyond the kitchen, the great room showcases vaulted ceilings, a fireplace, and an abundance of natural light. The first-floor primary suite is a true retreat with a spacious walk-in closet, and a beautifully remodeled spa inspired bathroom. Upstairs, you'll find three additional bedrooms, another full bathroom, and a dedicated laundry room for added convenience. The finished lower level offers flexible space perfect for a media room, home gym, recreation area, or playroom. Step outside onto the oversized two-tier deck overlooking the expansive backyard - an ideal setting for entertaining or relaxing in total privacy. Additional upgrades include a new roof, windows, siding, HVAC system, and brand-new 5-bedroom septic system. Complete with a 2-car garage and set in a picturesque location, this turnkey property offers the perfect blend of luxury, comfort, and functionality.

136 Goose Hill Rd, Chester
6 Pelton Hl, Chester
$813,500
3 Beds ⋅ 2 Baths ⋅ 24159531 MLS
Nestled at the end of a peaceful, dead-end street, this beautifully maintained Carpenter Gothic home offers the perfect blend of historic charm and modern comforts. With its unique architectural style and serene private setting, this property is truly a hidden gem. The three Bedrooms are spacious and bright, each bedroom offers a cozy retreat with plenty of natural light and charming details that highlight the home's architectural character. Enjoy year-round comfort with central air conditioning throughout the home, ensuring a perfect temperature no matter the season. The living room features an elegant Rumford fireplace, perfect for cozy evenings. The classic design enhances the room's inviting, warm atmosphere, making it an ideal space for gatherings or quiet nights in. Relax and unwind in the in-ground pool, set atop a beautifully terraced yard. The space is ideal for entertaining, lounging, or enjoying a swim while surrounded by nature. A spacious two-car garage offers both parking and additional storage. There are hardwood floors on the main level and wide board pine on the upper level adding a timeless elegance and warmth to each room. The home comes equipped with a generator, providing peace of mind in all weather conditions. Walking distance to the heart of Chester's charming town center, you'll have easy access to local shops, dining, and community events, while still enjoying the peace and privacy of your secluded retreat.

6 Pelton Hl, Chester
14 Maple St, Chester
$810,000
3 Beds ⋅ 4 Baths ⋅ 24127687 MLS
Quintessential Chester! This Federal Greek Revival Post and Beam Antique Colonial has been lovingly restored and updated. Mere steps to the Town Center! Taste the true flavor of New England by enjoying this characteristically charming Connecticut Village, well known for its resturants, art galleries, and seasonal events, along with boat marinas and yacht clubs for summer fun. Special features of the home include the copper kitchen countertop, custom spot lighting, wide King's Board flooring, exposed posts, and Rumsford Fireplaces. This home has been freshly painted throughout the interior and tastefully accented, as well as beautifully landscaped with stone patios and a Pergola. Have you always wanted a "secret garden"? Lots of parking is available for multiple cars and toys. There is also an additional in-law or private entry office with full kitchen and 1.1 baths. Make your plans to visit this exceptional home!

14 Maple St, Chester
6 Jagger Ln, Chester
$805,000
2 Beds ⋅ 3 Baths ⋅ 24164157 MLS
Step into timeless New England charm with this beautifully updated 1901 Colonial, where classic character meets modern comfort just moments from the heart of Chester. Thoughtfully renovated between 2008 and 2023, this inviting home offers warm, sun-filled spaces designed for both everyday living and and entertaining. Gather in the formal living and dining rooms, enjoy casual meals in the updated kitchen with granite countertops and stainless steel appliances, or relax in the open family room that flows seamlessly to the deck-complete with an outdoor shower for summer living. A first floor office or den with built-ins and it's own private entrance provides the perfect space for working from home or welcoming clients. Upstairs, two comfortable bedrooms and a full bath surround a charming landing, while the third floor offers a cozy retreat with bedroom area and sitting room-ideal for guest or a peaceful hideaway. Set on a level usable property with mature landscaping, the grounds feature a rustic cabin currently used as an art studio, adding creative flexibility and a touch of whimsy. All this, just around the corner from Chester's vibrant town center with it's shops, restaurants and community events, makes this home a rare blend of historic charm, modern updates and walkable small-town living. This property is subject to probate approval.

6 Jagger Ln, Chester
35 Maple St, Chester
$780,000
3 Beds ⋅ 2 Baths ⋅ 24138011 MLS
Steps to the Village! Vintage 1765 Cape with many updates but still true to the original charm of the Joseph Shipman House. Two staircases, 4 working firplaces, King's Board floors, wonderful floorplan and an up-to-date kitchen makes this home a step back in time but with the amenities of today. Quartz countertops and a complete kitchen renovation in 2017. New rear pressure treated deck in 2017. Renovated bath on first floor in 2018. Roof replaced in 2018 and gutters added. Complete second floor bath renovation off Primary Bedroom ( dual entrance ) in 2022. Invisible Fence. Brand new Post and Beam Barn with metal roof constructed in 2020 has a fantastic second floor space perfect for artists, craftsmen, or separate office - you have GOT to see it! Separate shed workshop with lighting and heater offers even more. Rear fieldstone patio was renovated and knee wall added in 2024. Freshly painted through out interior. Concrete floored basement. New hot water heater in 2022. A very special home on a totally usable level lot just a skip away from all the Village activities that Chester has to offer!

35 Maple St, Chester
28 Hoop Pole Hill Rd, Chester
$760,000
4 Beds ⋅ 4 Baths ⋅ 24104682 MLS
Discover the perfect blend of elegance and convenience in this custom Cape Cod home, nestled privately in Chester, CT. Boasting 4 bedrooms and 3.5 baths, this residence is convenient to the vibrant downtown area and easily accessible to the highway, yet set in a quiet woodland sanctuary, directly across from over 100 acres of state forest and trails. With timeless decor that exudes classic charm, the main level is thoughtfully designed with your comfort in mind. It features a primary bedroom suite with a spa-like full bath for ease of living, a cozy living room with built-ins provides a tranquil space to unwind, while the formal dining room is ideal for hosting gatherings. The heart of the home is the kitchen, where warm cabinetry and granite countertops invite culinary exploration made easy with a pot filler, warming drawer and 7 foot island with sink. Alfresco dining is steps away through the sliders to the trex deck. Upstairs, three additional generously sized bedrooms , including one with a private bath. The home's versatility shines with a bonus room accessed by a separate staircase- perfect for a home office, media room or family room. Additional living space awaits your finishing touches in the basement, complete with sliders that open to the backyard oasis with a Koi pond and rolling lush lawns. This Chester gem combines the warmth of a family home with the sophistication of upscale living. Don't miss the opportunity to make this house your forever home

28 Hoop Pole Hill Rd, Chester
16 Hickory Hill Dr, Chester
$755,000
3 Beds ⋅ 3 Baths ⋅ 24123794 MLS
Welcome to this well maintained 3 Bedroom Cape in the charming town of Chester, just a short distance from downtown. The first floor of this home has an upscaled eat-in kitchen with newer appliances, breakfast bar and granite countertops, a Living/Dining room running front to back, an Office with built-in custom bookshelves and file drawers and a large (17 X 14), inviting Family Room with Propane Fireplace & Atrium door access to the Patio and Garden. The Primary Bedroom with ensuite bath along with two other bedrooms and full bath complete the second floor. This home sits on 1.38 acres - where nature and landscaped gardens meet. Relax on the Bluestone Patio and enjoy the Garden water feature, Pergola and establisted Plantings for a peaceful retreat. Central Air, Buderus Furnace with Indirect water tank, 3 Zone Heat and 2- 750 Gallon oil tanks.

16 Hickory Hill Dr, Chester
9 Hickory Hill Dr, Chester
$750,000
3 Beds ⋅ 3 Baths ⋅ 24138968 MLS
Welcome to 9 Hickory Hill Drive! Set high on a hill in the heart of the charming Connecticut River Village of Chester. This striking Contemporary offers over 2800 sqft. of light-filled living space on 1.23 private acres-just a 3/10 mi stroll to Main St. The inviting foyer opens to a stunning, sun-drenched living area with skylights and gleaming hardwood floors throughout the living room, dining room, kitchen, library, and family room. The thoughtfully designed layout creates an easy flow for both daily living and entertaining. Also on the main level are two bedrooms-one currently serving as an artist's studio with a spacious adjacent walk-in storage room. Upstairs, an open loft-style office/media area overlooks the living space below and leads to the serene primary suite. An additional exercise or media room completes the upper level. Recent updates include several new windows, skylight, doors, flooring, and beautifully renovated kitchen featuring dramatic quartzite "Blue Explosion" counters, red maple floors, a bar with wine cooler, and newly updated bath. Enjoy peaceful, elevated views from the expansive deck overlooking the private, wooded backyard. The property also includes a two-car under-house garage plus a heated detached one-car garage/workshop-perfect for hobbyists & collectors. Ask to see the full list of improvements. Ideally located midway between New York City & Boston, you'll love the vibrant arts scene, fine dining, and welcoming spirit of historic Chester!

9 Hickory Hill Dr, Chester
8 Butter Jones Rd, Chester
$715,000
3 Beds ⋅ 3 Baths ⋅ 24124486 MLS
Enchanting Cape with Artisan Post & Beam Charm - Just Down the Road from Chester Village! Tucked away on 2 acres of picturesque land, this whimsical 3-bedroom, 2.5-bath Cape Cod home invites you to live among nature in style. Only a short distance from Cedar Lake and Chester Village, you'll have easy access to endless outdoor adventures and world-class restaurants and shopping just moments away. Inside, the home is a masterpiece of artisan post and beam craftsmanship, with a spacious great room featuring soaring ceilings, skylights that bathe the space in natural light, and exquisite woodwork that brings warmth and character to every corner. The thoughtful layout includes a generous primary suite with its own bath, two additional bedrooms, a full bath, and a convenient powder room for guests. Outside, the property is equally enchanting. The oversized detached garage and expansive workshop, both with the artisan craftsmanship of the main house, provide plenty of room for your hobbies and projects, while the barn and stables are ready for your animals. Whether you dream of an equestrian escape or simply crave a peaceful haven to enjoy nature, this home offers it all. From the captivating craftsmanship to the stunning natural surroundings, this is more than just a home, it's a retreat, a sanctuary, and a lifestyle.

8 Butter Jones Rd, Chester
226 Middlesex Ave, Chester
$695,000
4 Beds ⋅ 3 Baths ⋅ 24165416 MLS
Prominently set on over two picturesque acres in historic Chester, this custom-built and thoughtfully designed Saltbox Colonial offers the perfect blend of timeless New England charm and modern home comforts. Lovingly maintained by the original owner, a gracious entry leads to a cozy family room centered around the fireplace, creating a warm and welcoming atmosphere year-round. The formal living room and dining room with custom built-ins and gleaming hardwood floors is perfect for holiday gatherings or those special occasions with friends & family. The sun-filled kitchen with a center island and casual dining area leads to a private deck overlooking park-like grounds...ideal for outdoor entertaining. A half bath and laundry area complete the main level. Upstairs you'll find 4 bedrooms including the primary suite with its own private bath while the lower level features a bonus room and workshop. Bordered by mature trees and colorful perennials the spacious yard is ideal for gardening; a charming potting shed is perfect for all of your storage needs. A true highlight of this unique property is the 22 x 30 Country Carpenter carriage house barn/garage. Located just minutes from the Village, this quintessential New England home with seasonal views of the CT River, is close to Chester Boat Basin...offering easy access to boating and outdoor recreation. Whether you are looking for a full time residence or an ideal weekend retreat this is the perfect place to call home.

226 Middlesex Ave, Chester
59-61 Wig Hill Rd, Chester
$695,000
5 Beds ⋅ 3 Baths ⋅ 24166010 MLS
The spacious main house and separate guest/rental house sit on 3.64 park like acres abutting Chester Land Trust property. The front to back living/dining room features two large picture windows overlooking the rear landscape and a vaulted ceiling with second floor balcony. The cook's kitchen features newer appliances, granite counters, tile floor and eating area with sliding glass doors to a deck with Pau Lope decking. There is also a comfortable sitting area and half bath. The other end of the first floor has the primary bedroom with a large dressing room and bath. A separate den/office overlooks another rear deck. To complete the first floor is a large family room or office. Upstairs are four more bedrooms and a hall bath. The separate guest house is 720 square feet and has a kitchen, full bath, living/dining room and comfortable bedroom. It is currently rented. The property is in a convenient area to Chester Village featuring restaurants and specialty shops, the elementary school and Route 9.

59-61 Wig Hill Rd, Chester
112 Oakwood Trl Unit 112, Chester
$645,000
2 Beds ⋅ 3 Baths ⋅ 24202649 MLS ⋅ The Forest BLDG.
A distinctive offering in Chester's only 55+ condominium community, privately set along a quiet cul-de-sac. This beautifully appointed two-bedroom, two-and-a-half-bath residence pairs custom details with an open, light-filled design and a well-planned first-floor layout. The main living space features hardwood floors, abundant windows, and a gas fireplace creating a warm architectural focal point. The chef's kitchen is finished with rich cherry cabinetry, corian countertops, a generous island, and custom details throughout. The first-floor primary suite features a private full bath and two ample closets. Upstairs, a spacious open family room/loft with custom built-ins creates an inviting library, reading area, or study, accompanied by a private bedroom, full bath, and separate office/flex room. Just off the kitchen, a three-season sunroom overlooks the private backyard and lightly wooded surroundings, while a bluestone patio offers additional outdoor living space. An attached two-car garage and full basement provide additional storage. Set in the quintessential town of Chester, known for acclaimed restaurants, independent shops, galleries, and its celebrated village atmosphere. A rare opportunity for refined, low-maintenance living with exceptional space and craftsmanship.

112 Oakwood Trl Unit 112, Chester
1 Ferry Rd, Chester
$635,000
3 Beds ⋅ 3 Baths ⋅ 24146110 MLS
An extraordinary offering in one of Connecticut's most beloved river towns. Stunning sunrises over unobstructed views of Chester Creek sets the tone for this rare piece of Chester history. The Bani Denison homestead dates to 1781 and once served as Chester's first post office. Thoughtfully restored, this classic embankment Colonial with Dutch kick gambrel style roof offers modern amenities while preserving exceptional period detail throughout. Original wide-board chestnut floors and wall panels, six fireplaces (five working and wood-burning), original mantels and millwork, and two stairways, including the captain's staircase in the front foyer, define the home's character. The spacious primary bedroom features a barrel ceiling, fireplace and remodeled en-suite bath. A newly renovated kitchen blends seamlessly with the home's historic charm, while the finished lower level provides flexible space for a home office/studio/guest space with private entry. The home is filled with natural light throughout the day, the established backyard gardens providing privacy, and a seasonal floating dock offering access to the river for kayaks and small boats. Located in the picturesque Lower Connecticut River Valley, Chester is known for its charming village, galleries, shops, dining, and brewery. Nearby you'll find the historic Haddam-Chester Ferry, Goodspeed Opera House, and Gillette Castle State Park. Cockaponset State Forest nearby offers miles of trails for hiking, biking, and riding.

1 Ferry Rd, Chester
81 Main St, Chester
$618,000
2 Beds ⋅ 2 Baths ⋅ 24172804 MLS
Discover the perfect blend of mid-century character and modern efficiency in the heart of Chester Village. This impeccably maintained home offers a vibrant "walk-to-everything" lifestyle, just steps from award-winning dining, boutiques, and the theater. Officially a 2-bedroom home per town records, the layout offers incredible flexibility. The main level features a stunning den currently utilized as a primary suite. This light-filled space features a private, fully renovated ensuite full bath and a handsome armoire for storage, offering a sophisticated retreat for those seeking first-floor living. Note: This serves as the primary bath for the main level, enhancing the "suite" feel of the space. Upstairs, you will find two additional well-appointed rooms and a second fully renovated full bath, providing ample space for guests or a home office. The home's infrastructure has been flawlessly upgraded, featuring a new 50-year roof, on-demand propane heat/hot water, and an electric heat pump for heating and cooling (A/C on the first floor). The updated eat-in kitchen is a chef's delight, while the professional landscaping and beautiful stone patio create a private oasis for outdoor entertaining. Rarely does a home combine such high-end mechanical peace of mind with the undeniable charm of a downtown location. Turn-key and ready for its next chapter-experience the best of Chester right outside your front door.

81 Main St, Chester
16 Sypher Rd, Chester
$616,000
2 Beds ⋅ 3 Baths ⋅ 24170124 MLS
Good design is all about the detail and this the European inspired stucco home offers the perfect blend of casual and refined. Curated to perfection and offering desirable one floor living, spacious well-proportioned rooms blend seamlessly with the natural surroundings. Prominently set on 2.5 acres, natural stone steps lead to a warm and welcoming entrance. A light-filled entry foyer opens to the living room, centered around an impressive fireplace, and a casual dining area...ideal for everyday gatherings. Chef's will love the French country kitchen with its rustic charm and elegant, timeless design. Ideal for entertaining, French doors lead to a lovely screened-in porch overlooking park-like grounds. Two well-appointed en suite bedrooms, one opening to a private study with a cozy fireplace, feature plenty of closet space. The full basement offers ample storage & updated mechanicals are sure to give buyers peace of mind. This unique home is bordered by beautiful stone walls, pretty azaleas, colorful hydrangeas and mature rhododendrons...all woven into this magical landscape. Stately oaks, maples & specimen trees adorn the property and a charming potting shed is perfect for all your gardening needs. Whether you are looking for a full-time residence or the ideal weekend retreat, this precision-engineered home reflects the owners own signature style...providing the beauty of a traditional site-built home with the added benefits of modern home construction. Truly one of a kind!

16 Sypher Rd, Chester
13 Cross Rd, Chester
$610,000
3 Beds ⋅ 3 Baths ⋅ 24122260 MLS
Set on a private 4.48-acre lot, this inviting Colonial offers over 2,300 sq. ft. of comfortable living space with 8 spacious rooms, including 3 bedrooms. The welcoming family room features a fireplace, built-ins, soaring cathedral ceilings, a large skylight, and sliders leading to the rear deck, filling the home with natural light. Enjoy the tranquility and privacy of the setting while still having room to grow-expansion potential over the attached garage offers the perfect opportunity to create a home office, game room, or bonus retreat tailored to your lifestyle."

13 Cross Rd, Chester
26 Ferry Rd, Chester
$600,000
4 Beds ⋅ 2 Baths ⋅ 24148777 MLS
Located in the Town of Chester, this residential 2 Family property presents a rare opportunity to acquire a multifamily property in one of Connecticut's most desirable markets. The property consists of two 2-bedroom residential apartments. The improvements are situated on over 2 acres of land. Waterhouse Brook flows directly through the site, creating a tranquil backdrop, while the property enjoys a line of sight toward Gillette Castle, adding to its distinctive character and long-term appeal.

26 Ferry Rd, Chester
28 S Wig Hill Rd, Chester
$580,000
2 Beds ⋅ 3 Baths ⋅ 24112154 MLS
Step into history with this 1770 Cape, part of "Old Homes of Chester." Nestled on beautiful grounds featuring rolling hills, gardens, and stunning stone walls, the property abuts 8 acres of serene land trust, offering unparalleled privacy and a park-like setting. The main house spans 1303 square feet and includes 2 bedrooms and 2 full baths. Recent upgrades include a new furnace (2023), electric hot water heater, oil tank (2022), and a whole-house generator, ensuring modern comfort while maintaining historic charm. A delightful patio with a gazebo, adorned with wine grapes, provides a perfect spot to relax and enjoy the picturesque surroundings. Additionally, the property features a 1020 square foot heated "artist studio" complete with a kitchen, full bath, and loft. This versatile space is ideal for an in-law suite, office, workshop, art studio, or potential rental. The property also includes a detached garage with its own driveway and a storage shed, enhancing its functionality. Located close to Chester's fine dining, boutique shopping, and the recreational offerings of Cedar Lake with its two public beaches, this home offers a blend of historic elegance and modern convenience. Perfect for those seeking a serene, yet accessible retreat, 28 S Wig Hill Road is a unique opportunity to own a piece of Chester's rich history, set amidst a stunning natural landscape.

28 S Wig Hill Rd, Chester
7 Hickory Hill Dr, Chester
$549,000
3 Beds ⋅ 3 Baths ⋅ 24152380 MLS
Enjoy the convenience of walking to Chester Village from this 3 bedroom Colonial, perfectly situated on a quiet dead end street. The home features a spacious eat-in kitchen with stainless steel appliances, a cozy family room with fireplace, a formal dining room, and a separate living room ideal for entertaining. Upstairs, you'll find generously sized bedrooms with ample closet space. Packed with opportunity, this property is primed for your updates and creative vision.

7 Hickory Hill Dr, Chester
131 Middlesex Ave, Chester
$530,000
3 Beds ⋅ 3 Baths ⋅ 24125901 MLS
Discover this waterfront delight in charming Chester, rewarding with year-round views! Completely renovated in 2012 from the ground up (including brand new septic system), this pristine Colonial offers 3 floors of living space and a smart L-shape open floor plan ensuring that you always have a gorgeous view. In addition to some hardworking 1st floor spaces (roomy mudroom, full bath and laundry room), the main living area serves up the ideal layout for dining, cooking and relaxing. The space enjoys loads of windows and natural light, oak HW flooring, white kitchen cabinetry w/ granite counters and marble tile backsplash, tiered island with breakfast bar, and SS appliances including a new gas range -- all with amazing views of Chester Cove. Step through the slider and get even closer to those glorious sunsets from the large deck with stainless cable railing. Upstairs are 3 bedrooms, 2 with western exposure & unobstructed water views. The primary bedroom includes a walk-in-closet and Jack & Jill bathroom. The lower level provides additional storage & finished space, ideal for a yoga studio, or home gym. Need more to love? Central A/C, new hot water heater (2024), plenty of closets and storage, 1-car garage with 50 AMP EV charger & private level yard. Just a mile to Chester Village center and .5 mile to the marinas. Enjoy everything that this picturesque CT town has to offer and, remember, everything was new in 2012. AE flood zone w/ transferrable policy, premium just $1231/yr

131 Middlesex Ave, Chester
43 Goose Hill Rd, Chester
$525,000
3 Beds ⋅ 2 Baths ⋅ 24205998 MLS
Welcome to 43 Goose Hill Road, a well-maintained, one-owner residence offering a wonderful combination of privacy, character, and a beautiful Chester setting. A well-known local engineer designed and assisted in the building of this thoughtfully constructed home. The property has been carefully maintained and improved over the years. Set well back from the road, the property offers a peaceful and private setting accented by classic New England stone walls and its own pond. Inside, the home features an updated kitchen along with comfortable, inviting living spaces that have been well cared for throughout. A whole-house generator provides added peace of mind, while the attached heated two-car garage offers a spacious loft ideal for additional storage. The additional heated 1 bay garage is such a versatile space. You may want to use this space as extra outdoor/indoor living for your patio, as a workshop, or countless other possibilities. With its private setting, picturesque grounds, pond, stone walls, and long history of attentive ownership, 43 Goose Hill Road is a special property offering the quiet charm and character that make Chester such a desirable place to call home. Please note - Highest and best due Saturday the 19th at 5pm.

43 Goose Hill Rd, Chester
12 Meadow Ln, Chester
$515,000
3 Beds ⋅ 3 Baths ⋅ 24186457 MLS
Set at the end of a quiet dead-end road, this three-bedroom ranch offers the ease of one-floor living, exceptional privacy, and over four acres of peaceful surroundings in Chester. Inside, two inviting wood stoves create warm, comfortable gathering spaces, while a newer roof adds peace of mind. Step outside to a covered deck that flows seamlessly to an open deck overlooking the private backyard with seasonal views of the Connecticut River-an ideal setting for relaxing, entertaining, or enjoying the changing seasons. The home also features a spacious two-car attached garage and a large accessory dwelling unit (ADU) with a full walkout to the backyard, offering flexible space for extended living arrangements, guests, a home office, recreation, or other permitted uses. Combining acreage, privacy, versatile living space, and a tranquil setting, this property is ideally located just minutes from Chester Village, offering easy access to local shops, restaurants, art galleries, breweries, nearby marinas, and the scenic Connecticut River.

12 Meadow Ln, Chester
11 Castle View Dr, Chester
$502,500
3 Beds ⋅ 2 Baths ⋅ 24198796 MLS
Offered for sale for the very first time, this lovingly cared-for home is a rare opportunity in the welcoming Castle View Drive neighborhood, just moments from Chester Center. While the manicured lawn, mature gardens, and meticulous exterior maintenance create an excellent first impression, this home is much larger than it appears from the front elevation. Step inside and discover a spacious floor plan that extends deep into the level double lot, complete with a patio for outdoor enjoyment and over 465 square feet of additional finished space in the lower level. For added peace of mind, the lower level has been recently waterproofed by the renowned Connecticut Basement Systems (formerly Janesky). The main level features a generous family room with hardwood flooring and a cozy fireplace, while the bedroom wing offers two bedrooms as well as the primary suite with private bath. The flexible fourth bedroom, currently housing the conveniently located laundry area, can easily serve as a nursery, home office, or guest room. Thoughtful cosmetic updates include quartz countertops, stainless steel appliances, and a custom sliding pantry in the kitchen. Equally impressive are the home's significant mechanical and structural improvements, including central air conditioning, a newer architectural roof, a Buderus boiler, a new drilled well, and an upgraded electrical panel w/ generator hookup. This exceptionally maintained home offers comfort, flexibility, and confidence for years

11 Castle View Dr, Chester
22 Goose Hill Rd, Chester
$500,000
3 Beds ⋅ 3 Baths ⋅ 24192206 MLS
Welcome to this inviting 3-bedroom split-level ranch, ideally situated within walking distance to the heart of Chester Village. Designed for comfortable living and entertaining, the home features a spacious family room with sliders leading to a large deck overlooking the inground pool. The backyard is an outdoor retreat complete with a pool house, gazebo with electricity, mature fruit trees, and a large open yard offering endless possibilities. Inside, you'll find two fireplaces-one in the living room and another in the lower-level recreation room-creating warm and welcoming spaces throughout the seasons. The remodeled kitchen features granite countertops, ample cabinetry, and a functional layout for everyday living. The primary bedroom includes a private half bath, and the two-car attached garage provides plenty of storage and convenience. Recent upgrades include a newer boiler, central air condenser, and garage doors, providing added value and peace of mind. Just a short walk from Chester Village, you'll enjoy convenient access to art galleries, locally owned restaurants, unique boutiques, and seasonal community events. This home offers a wonderful opportunity to add your personal touches while enjoying a spacious property, exceptional outdoor amenities, and all that Chester has to offer.

22 Goose Hill Rd, Chester
275 W Main St, Chester
$495,000
4 Beds ⋅ 2 Baths ⋅ 24173958 MLS
***Multiple offers received. Seller has asked for best and final by Monday 5/18 5pm*** Set on an exceptional 2-acre parcel in the charming Connecticut River town of Chester, this 4-bedroom, 2-bath Colonial offers endless potential in a truly special setting. Being offered for the first time in 55 years, this well-loved home is filled with warmth and character throughout, featuring hardwood floors and three fireplaces, including one in the spacious primary bedroom. Mature plantings surround the property, creating a peaceful outdoor backdrop complete with a pond perfect for relaxing and enjoying nature. Additional highlights include an attached 2-car garage, two shed/barn outbuildings, and newer major mechanical updates including the roof, furnace, and oil tank. The home also offers finished space in the basement complete with a fireplace, ideal for entertaining, a home office, or flexible additional living space. Located directly across the street from Cockaponset State Forest, this property is ideal for those who appreciate outdoor recreation and nature. Whether you're looking to preserve its timeless charm or add your own finishing touches, this is an exceptional opportunity to make it your own. Enjoy all that Chester has to offer, including acclaimed restaurants, art galleries, unique local shops, and the charm of one of Connecticut's most beloved river towns.

275 W Main St, Chester
19 Castle View Dr, Chester
$470,000
3 Beds ⋅ 2 Baths ⋅ 24174952 MLS
Beautifully rebuilt from top to bottom, this stunning 3-bedroom, 1.5-bath home is not just remodeled - it has been completely reimagined for today's homeowner. Every detail has been thoughtfully designed so the new owner can simply turn the key and begin the next chapter. Step inside and immediately feel the warmth of the beautifully refinished hardwood floors flowing throughout the home. The inviting living room centers around a charming fireplace, creating the perfect gathering space where memories are waiting to be made. The brand-new kitchen features stylish cabinetry, quartz countertops, and all new stainless-steel appliances, offering both beauty and functionality. Just steps away, the sun-filled dining room provides ample space for everyday living and entertaining alike. Both bathrooms have been completely updated with tile flooring, new vanities, and modern fixtures. Major improvements include new windows, siding, roof, insulation, garage door, and septic system, giving peace of mind for years to come. With nothing left to do but enjoy, this home offers the perfect combination of classic charm and modern convenience. Ideally located just minutes from the heart of charming downtown Chester, you'll enjoy easy access to elegant boutiques, art galleries, exceptional restaurants, and the renowned Goodspeed Opera House. Small-town New England living has never looked so good.

19 Castle View Dr, Chester
36 Kings Hwy, Chester
$469,900
4 Beds ⋅ 2 Baths ⋅ 24130591 MLS
Charming Stone Home on Nearly 4 Acres! Just minutes from Chester Village, this distinctive home blends character and modern updates. Enjoy an eat-in kitchen with quartz counters, 3-4 bedrooms, and a versatile home office. Recent upgrades include hardwood floors, new roof and gutters, furnace, oil tank, solar panels, and surveillance system. A detached stone 2-car garage completes this rare find! **solar panels through energize CT. The company is Sunova and pays $90.00 a month. electric bill for last month was $36.00 but seller financed furnace through Eversource for .01% and that is $72.00 a month. So last month their solar paid half the furnace bill and had no electric charges. There are months that it pays the entire $72.00 and they don't owe anything. Their highest actual electric bill was about $120 - that is misusing out the $72.00 dollars a month for the furnace The Solar contract is transferrable, but seller has to pay off the furnace as that is a loan in sellers name and part of their electric bill. Last electric bill attached in documents.

36 Kings Hwy, Chester

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