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$1,900,000

The Johnathan Warner house, and later known as the Warner-Brooks House was built by Johnathan Warner in 1798 and is a remarkable testament to early American prosperity, craftsmanship, and vision. Listed on the National Register of Historic Places, this exceptional Federal-style residence retains extraordinary architectural integrity. Heavily documented during construction are original bills, receipts, and construction records documenting the artisans materials, suppliers, and methods used to create this architectural masterpiece. Revered by historians and preserved with exceptional care, this irreplaceable legacy property offers a rare opportunity to own one of Connecticut's most significant surviving Federal residences. A once-in-a-generation opportunity to become the steward of one of the Connecticut River Valley's most important historic estates. Jonathan Warner was the founder of the Chester-Hadlyme Ferry which is right down the road and is still in operation today. Johnathan was a Civic Leader, director of the Middlesex Turnpike, Merchant, Ship Owner, Farmer, Constable, and a justice of the peace with his courtroom right at the house. This is all documented in a book called Johnathan Warner 1728-1810 " A Man of Parts" telling all about the home building and Johnathan's life. Copies can be found at the Chester Historical Society. Buyer must due diligence regarding subdivision possibilities. 3.2 acres of which most is a huge level cleared open field. Come visit Chester

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24206419 MLS

The Johnathan Warner house, and later known as the Warner-Brooks House was built by Johnathan Warner in 1798 and is a remarkable testament to early American prosperity, craftsmanship, and vision. Listed on the National Register of Historic Places, this exceptional Federal-style residence retains extraordinary architectural integrity. Heavily documented during construction are original bills, receipts, and construction records documenting the artisans materials, suppliers, and methods used to create this architectural masterpiece. Revered by historians and preserved with exceptional care, this irreplaceable legacy property offers a rare opportunity to own one of Connecticut's most significant surviving Federal residences. A once-in-a-generation opportunity to become the steward of one of the Connecticut River Valley's most important historic estates. Jonathan Warner was the founder of the Chester-Hadlyme Ferry which is right down the road and is still in operation today. Johnathan was a Civic Leader, director of the Middlesex Turnpike, Merchant, Ship Owner, Farmer, Constable, and a justice of the peace with his courtroom right at the house. This is all documented in a book called Johnathan Warner 1728-1810 " A Man of Parts" telling all about the home building and Johnathan's life. Copies can be found at the Chester Historical Society. Buyer must due diligence regarding subdivision possibilities. 3.2 acres of which most is a huge level cleared open field. Come visit Chester

47 E Kings Hwy, Chester

$465,000

One level living at its best! Tucked away in a peaceful neighborhood, 6 Castle View Drive offers the perfect blend of comfort, charm, and convenience. This lovingly cared for home features 3 bedrooms, 1.5 baths, and 2,031 square feet of thoughtfully designed living space all set on a beautifully level 0.43 acre lot. Step inside through the breezeway, kick off your shoes, hang your coat, and make your way into the completely renovated kitchen before settling into the sun filled living room, where a wood burning fireplace creates the perfect spot for cozy evenings. Just beyond, the bonus room offers a quiet place to read your favorite book, work from home, or simply unwind. Outside, the large fenced in backyard is ready for summer barbecues, a garden, kids at play, or four-legged friends to roam. Sit back and enjoy a quiet afternoon while listening for the nostalgic whistle of the Essex Steam Train in the distance, a small reminder of the timeless New England charm that makes this area so special. Recent upgrades include a brand new roof and siding, offering added peace of mind for years to come. When you're ready to venture out, the charm of Chester Village is just minutes away. Enjoy dinner downtown, wander through the local shops and galleries, or make an evening of it with a show at the Goodspeed. Whether you're putting down roots or looking to simplify. 6 Castle View Drive is a wonderful place to call home and ready for its next chapter

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24102694 MLS

One level living at its best! Tucked away in a peaceful neighborhood, 6 Castle View Drive offers the perfect blend of comfort, charm, and convenience. This lovingly cared for home features 3 bedrooms, 1.5 baths, and 2,031 square feet of thoughtfully designed living space all set on a beautifully level 0.43 acre lot. Step inside through the breezeway, kick off your shoes, hang your coat, and make your way into the completely renovated kitchen before settling into the sun filled living room, where a wood burning fireplace creates the perfect spot for cozy evenings. Just beyond, the bonus room offers a quiet place to read your favorite book, work from home, or simply unwind. Outside, the large fenced in backyard is ready for summer barbecues, a garden, kids at play, or four-legged friends to roam. Sit back and enjoy a quiet afternoon while listening for the nostalgic whistle of the Essex Steam Train in the distance, a small reminder of the timeless New England charm that makes this area so special. Recent upgrades include a brand new roof and siding, offering added peace of mind for years to come. When you're ready to venture out, the charm of Chester Village is just minutes away. Enjoy dinner downtown, wander through the local shops and galleries, or make an evening of it with a show at the Goodspeed. Whether you're putting down roots or looking to simplify. 6 Castle View Drive is a wonderful place to call home and ready for its next chapter

6 Castle View Dr, Chester

$1,350,000

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.

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$764,900

Privacy, space, and location come together in this classic custom colonial nestled on over two private acres at the end of a quiet cul-de-sac just minutes from the heart of Chester Village. Lovingly cared for by its original owners, this 2,662-square-foot home offers a rare opportunity to enjoy the tranquility of a tucked-away setting without sacrificing proximity to downtown. An inviting covered front porch welcomes you to sit down and admire the professionally landscaped front yard before entering the home. Inside, the entryway is bordered by both a living room and a formal dining room with a bay window. There is also a spacious family room with a propane fireplace, and a sunny kitchen with a center island and ample cabinet space, a breakfast nook, and pantry. The nook leads to the large back deck overlooking the backyard, perfect for al fresco dining, entertaining, or simply enjoying the natural beauty and quiet surroundings. The second story offers four bedrooms, including the primary suite with a generous walk-in closet and ensuite bathroom that features both a soaking tub and shower. Three more bedrooms share another full bath, and there is also a bonus room over the garage that could serve as a den, office, or playroom. There is a two-bay, two car garage and a full unfinished basement. Ideally situated near Chester's acclaimed restaurants, shops, galleries, and village amenities, this property offers the best of both worlds: a private retreat with the character and

4 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24198973 MLS

Privacy, space, and location come together in this classic custom colonial nestled on over two private acres at the end of a quiet cul-de-sac just minutes from the heart of Chester Village. Lovingly cared for by its original owners, this 2,662-square-foot home offers a rare opportunity to enjoy the tranquility of a tucked-away setting without sacrificing proximity to downtown. An inviting covered front porch welcomes you to sit down and admire the professionally landscaped front yard before entering the home. Inside, the entryway is bordered by both a living room and a formal dining room with a bay window. There is also a spacious family room with a propane fireplace, and a sunny kitchen with a center island and ample cabinet space, a breakfast nook, and pantry. The nook leads to the large back deck overlooking the backyard, perfect for al fresco dining, entertaining, or simply enjoying the natural beauty and quiet surroundings. The second story offers four bedrooms, including the primary suite with a generous walk-in closet and ensuite bathroom that features both a soaking tub and shower. Three more bedrooms share another full bath, and there is also a bonus room over the garage that could serve as a den, office, or playroom. There is a two-bay, two car garage and a full unfinished basement. Ideally situated near Chester's acclaimed restaurants, shops, galleries, and village amenities, this property offers the best of both worlds: a private retreat with the character and

13 High Field Ln, Chester

$599,900

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.

2 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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

$2,995,000

Set along a coveted and historic stretch of the Connecticut River, East View is a rare waterfront compound where extraordinary frontage, architectural integrity and Connecticut River Valley charm converge. Just over one mile from the village, this turnkey 2.65-acre estate offers 285 feet of direct river frontage, protected views and deep-water access. The river is the focal point framed by manicured grounds and a broad terrace leading gently to the water. A six-pile, deep water dock with two slips and a 16-ton lift is designed for serious boaters, while paddling is enjoyed from the floating dock and a small beach. Rooted in historic design and masterfully renovated in 2010, the residence blends timeless New England architecture with modern livability. Equally suited to weekends on the water, extended family gatherings, or multi-generational living, the property offers flexible spaces designed to entertain and live comfortably. Find a total of six garage bays for auto collections, boats, or a workshop. Minutes away discover Chester Village restaurants and artisans. Just across the river, the Goodspeed Opera House adds celebrated cultural dimension, and the neighboring seasonal Connecticut Valley Railroad evokes the region's rich history. The quiet elegance of East View offers a rare opportunity to experience the Connecticut River at its most extraordinary-where boating, history, culture, village life, and natural beauty converge.

4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24201816 MLS

Set along a coveted and historic stretch of the Connecticut River, East View is a rare waterfront compound where extraordinary frontage, architectural integrity and Connecticut River Valley charm converge. Just over one mile from the village, this turnkey 2.65-acre estate offers 285 feet of direct river frontage, protected views and deep-water access. The river is the focal point framed by manicured grounds and a broad terrace leading gently to the water. A six-pile, deep water dock with two slips and a 16-ton lift is designed for serious boaters, while paddling is enjoyed from the floating dock and a small beach. Rooted in historic design and masterfully renovated in 2010, the residence blends timeless New England architecture with modern livability. Equally suited to weekends on the water, extended family gatherings, or multi-generational living, the property offers flexible spaces designed to entertain and live comfortably. Find a total of six garage bays for auto collections, boats, or a workshop. Minutes away discover Chester Village restaurants and artisans. Just across the river, the Goodspeed Opera House adds celebrated cultural dimension, and the neighboring seasonal Connecticut Valley Railroad evokes the region's rich history. The quiet elegance of East View offers a rare opportunity to experience the Connecticut River at its most extraordinary-where boating, history, culture, village life, and natural beauty converge.

288 Middlesex Ave, Chester

$1,900

LARGE 2 BEDROOM APARTMENT WITH NEWLY REDONE HARDWOOD FLOORS / FRESHLY PAINTED / UNIT HAS IT'S OWN FULL SIZE STACK WASHER & DRYER / UNIT IS RANCH ON THE SECOND FLOOR

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24201366 MLS

LARGE 2 BEDROOM APARTMENT WITH NEWLY REDONE HARDWOOD FLOORS / FRESHLY PAINTED / UNIT HAS IT'S OWN FULL SIZE STACK WASHER & DRYER / UNIT IS RANCH ON THE SECOND FLOOR

159 Main St Unit B, Chester

$284,900

Charming 1927 Colonial offering a rare chance to own directly on the water in the heart of Chester. This 3-bedroom, 1-bath home spans 1,217 sq ft across two stories, with a classic layout featuring a living room and dining room on the main level and three bedrooms upstairs. Set on a 0.27-acre lot with vinyl siding and a paved driveway, the home sits right on the water with tranquil river views - a fantastic canvas for a riverfront retreat, whether you're an investor or a homeowner seeking direct water access. Just a short stroll to downtown Chester's boutiques, art galleries, and acclaimed dining. This property can also be purchased together with the adjacent 90 Water St for a larger waterfront compound (the two share an existing septic system). Bring your vision - this rare Chester waterfront offering won't last long!

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24198196 MLS

Charming 1927 Colonial offering a rare chance to own directly on the water in the heart of Chester. This 3-bedroom, 1-bath home spans 1,217 sq ft across two stories, with a classic layout featuring a living room and dining room on the main level and three bedrooms upstairs. Set on a 0.27-acre lot with vinyl siding and a paved driveway, the home sits right on the water with tranquil river views - a fantastic canvas for a riverfront retreat, whether you're an investor or a homeowner seeking direct water access. Just a short stroll to downtown Chester's boutiques, art galleries, and acclaimed dining. This property can also be purchased together with the adjacent 90 Water St for a larger waterfront compound (the two share an existing septic system). Bring your vision - this rare Chester waterfront offering won't last long!

92 Water St, Chester

$269,900

Rare opportunity to own directly on the water in the heart of Chester. This 1950-built ranch offers 1,034 sq ft with a flexible layout - currently set up as a 1-bedroom, the spacious family room (10'3" x 20'10") could easily convert to a second bedroom or home office. The oversized living room (13'6" x 20'10") anchors the home, while the combined kitchen/dining area (10'5" x 16'2") and comfortable primary bedroom round out the interior. Step outside to direct river frontage with sweeping water views and endless potential for outdoor living on the riverbank. All of this just a short stroll from downtown Chester's boutiques, galleries, and acclaimed restaurants. This property can also be purchased together with the adjacent 92 Water St for a larger waterfront compound (the two share an existing septic system). A fantastic value-add opportunity for an investor or a buyer with vision - bring your contractor and imagination!

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24198111 MLS

Rare opportunity to own directly on the water in the heart of Chester. This 1950-built ranch offers 1,034 sq ft with a flexible layout - currently set up as a 1-bedroom, the spacious family room (10'3" x 20'10") could easily convert to a second bedroom or home office. The oversized living room (13'6" x 20'10") anchors the home, while the combined kitchen/dining area (10'5" x 16'2") and comfortable primary bedroom round out the interior. Step outside to direct river frontage with sweeping water views and endless potential for outdoor living on the riverbank. All of this just a short stroll from downtown Chester's boutiques, galleries, and acclaimed restaurants. This property can also be purchased together with the adjacent 92 Water St for a larger waterfront compound (the two share an existing septic system). A fantastic value-add opportunity for an investor or a buyer with vision - bring your contractor and imagination!

90 Water St, Chester

$2,500

Available 9/1/26! Taking applications now. Something special is happening at 100 W Main. This brand-new residence brings together thoughtful design, beautiful finishes, and the ease of modern living, all just minutes from the heart of Chester Village. **Unit B** has a style all its own. The bright, open living space centers around a beautifully finished kitchen with quartz countertops, a generous island, rich cabinetry, stainless steel appliances, warm brass accents, and pendant lighting. Wide-plank flooring carries throughout, complemented by abundant natural light and a clean, modern palette. The same attention to detail continues in the baths, with quartz surfaces, distinctive cabinetry, contemporary fixtures, and a glass-enclosed tiled shower. Generous closets and an in-unit stacked washer and dryer add the practical conveniences that make everyday living easy. And then there's Chester. One of those small towns that simply feels good to be in, with great restaurants, coffee, independent shops, galleries, theater, markets, and a genuine sense of community. The Connecticut River, trails, and outdoor spaces are nearby, while the village offers plenty of reasons to stay close to home. Enjoy the comfort and simplicity of a brand-new home while becoming part of a town with real character, culture, and community. A beautiful new residence, in a place you'll love calling home.

1 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24199482 MLS

Available 9/1/26! Taking applications now. Something special is happening at 100 W Main. This brand-new residence brings together thoughtful design, beautiful finishes, and the ease of modern living, all just minutes from the heart of Chester Village. **Unit B** has a style all its own. The bright, open living space centers around a beautifully finished kitchen with quartz countertops, a generous island, rich cabinetry, stainless steel appliances, warm brass accents, and pendant lighting. Wide-plank flooring carries throughout, complemented by abundant natural light and a clean, modern palette. The same attention to detail continues in the baths, with quartz surfaces, distinctive cabinetry, contemporary fixtures, and a glass-enclosed tiled shower. Generous closets and an in-unit stacked washer and dryer add the practical conveniences that make everyday living easy. And then there's Chester. One of those small towns that simply feels good to be in, with great restaurants, coffee, independent shops, galleries, theater, markets, and a genuine sense of community. The Connecticut River, trails, and outdoor spaces are nearby, while the village offers plenty of reasons to stay close to home. Enjoy the comfort and simplicity of a brand-new home while becoming part of a town with real character, culture, and community. A beautiful new residence, in a place you'll love calling home.

100 W Main St Unit B, Chester

$145,000

New to the market! Discover the perfect canvas for your dream home on this beautiful, private 4.91-acre wooded lot. Nestled within a private 8-lot subdivision just off Goose Hill Road, this parcel offers a rare blend of ultimate privacy and convenience, featuring excellent frontage on a paved, private road. The location is truly unbeatable, sitting just over a mile from the charming, historic village of Chester. A subdivision survey is already available, though no additional engineering has been performed on the lot. Opportunities like this in Chester are far and few between!

ACTIVE UNDER CONTRACT Status ⋅ 24180404 MLS

New to the market! Discover the perfect canvas for your dream home on this beautiful, private 4.91-acre wooded lot. Nestled within a private 8-lot subdivision just off Goose Hill Road, this parcel offers a rare blend of ultimate privacy and convenience, featuring excellent frontage on a paved, private road. The location is truly unbeatable, sitting just over a mile from the charming, historic village of Chester. A subdivision survey is already available, though no additional engineering has been performed on the lot. Opportunities like this in Chester are far and few between!

Goose Hill Rd, Chester

$1,995,000

A mixed-use and multifamily package located in Chester and Deep River, two of the most desirable towns in the Lower Connecticut River Valley. The offering includes: 59 Maple Street (Chester): 7-unit multifamily asset with an additional ~1,500 SF commercial warehouse on 2.5+ acres. 163 Main Street (Deep River): 5-unit mixed-use property positioned at the gateway to the downtown retail corridor. The portfolio is fully occupied and generates approximately $210,000+ in current gross income, with upside to over $280,000 stabilized, driven by residential and commercial rent growth. At stabilization, the portfolio delivers approximately $175,748 NOI and a 8.37% cap rate, supported by a strong 1.58x DSCR. The possibility to develop the 3rd floor of 163 Main Street into additional units can drive returns even higher! This is a rare opportunity to acquire scale across two supply-constrained markets, combining in-place cash flow with clear mark-to-market upside across both residential and commercial components.

11 Beds ⋅ 12 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24170551 MLS

A mixed-use and multifamily package located in Chester and Deep River, two of the most desirable towns in the Lower Connecticut River Valley. The offering includes: 59 Maple Street (Chester): 7-unit multifamily asset with an additional ~1,500 SF commercial warehouse on 2.5+ acres. 163 Main Street (Deep River): 5-unit mixed-use property positioned at the gateway to the downtown retail corridor. The portfolio is fully occupied and generates approximately $210,000+ in current gross income, with upside to over $280,000 stabilized, driven by residential and commercial rent growth. At stabilization, the portfolio delivers approximately $175,748 NOI and a 8.37% cap rate, supported by a strong 1.58x DSCR. The possibility to develop the 3rd floor of 163 Main Street into additional units can drive returns even higher! This is a rare opportunity to acquire scale across two supply-constrained markets, combining in-place cash flow with clear mark-to-market upside across both residential and commercial components.

59-65 Maple St, Chester