Dontayebrooksrealty.com Search Results

This beautifully maintained 1890 Farm House in coveted Deep Hollow Road is a rare opportunity and has been a labor of love over the time that the sellers have lived here. This 1.04 acre property on "The Hollow" consists of a house, an oversized 24' x 24' garage/shop, antique "pony" barn with authentic outhouse and custom built service barn suited for a man cave, cigar lounge or whatever else you can envision. Walking into the front door, expect an open floor plan with beautiful knotty alder doors, custom moldings, newly refinished arctic maple flooring, 2 tongue & groove cedar ceilings (1 w/rattan ceiling fans). New Kitchen Aid appliances in a kitchen just waiting for your vision & a spacious walk-in pantry w/ample storage. Gorgeous powder room tucked away features pedestal sink and a 100+ yr old antique cabinet. 2nd floor features 3 bedrooms, 2 which have cathedral ceilings w/remotely operated skylights w/rain sensors to automatically close at first sign of precipitation. Master bedroom has been plugged & wired for stackable washer/dryer. A stand up attic includes a whole house attic fan which creates an impressive amount of air flow. Second floor is on 4 zones of radiant heat; first floor is 1 zone. Basement is walk out and 400 sq ft of newly refreshed space. New carpet, great lighting and wonderful space for a playroom for children, man cave or home office/small business as utilized by the previous owners. Half bath in basement as well.

3 Beds ⋅ 3 Baths ⋅ 24199280 MLS

This beautifully maintained 1890 Farm House in coveted Deep Hollow Road is a rare opportunity and has been a labor of love over the time that the sellers have lived here. This 1.04 acre property on "The Hollow" consists of a house, an oversized 24' x 24' garage/shop, antique "pony" barn with authentic outhouse and custom built service barn suited for a man cave, cigar lounge or whatever else you can envision. Walking into the front door, expect an open floor plan with beautiful knotty alder doors, custom moldings, newly refinished arctic maple flooring, 2 tongue & groove cedar ceilings (1 w/rattan ceiling fans). New Kitchen Aid appliances in a kitchen just waiting for your vision & a spacious walk-in pantry w/ample storage. Gorgeous powder room tucked away features pedestal sink and a 100+ yr old antique cabinet. 2nd floor features 3 bedrooms, 2 which have cathedral ceilings w/remotely operated skylights w/rain sensors to automatically close at first sign of precipitation. Master bedroom has been plugged & wired for stackable washer/dryer. A stand up attic includes a whole house attic fan which creates an impressive amount of air flow. Second floor is on 4 zones of radiant heat; first floor is 1 zone. Basement is walk out and 400 sq ft of newly refreshed space. New carpet, great lighting and wonderful space for a playroom for children, man cave or home office/small business as utilized by the previous owners. Half bath in basement as well.

28 Deep Hollow Rd, Chester

$525,000

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.

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

$645,000

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 ⋅ 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

$502,500

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

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

$825,000

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.

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

$1,200,000

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 ⋅ 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

$140,000

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!

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

$430,000

Multiple offers - Seller requests highest and best, Monday, 7/27 by 5PM. No escalation clauses. Fantastic Opportunity in the Heart of Chester! Discover the potential of this charming 2 Bedroom, 1.5 bath ranch, perfectly situated within walking distance to downtown Chester. The highlight of this home is a newer, heated sunroom boasting wood floors, cathedral ceilings and an abundance of natural light overlooking a private 2.39 acre lot. The partially finished, walk-out lower level offers excellent flexible living space, complete with a half bath (with room to expand to a full shower) and a small kitchenette - ideal for an in-law or guest suite. Key features include: New oil-fired furnace; public water; central air; generator; freshly painted interior, one car garage and storage shed. Bring your updates and vision to life! With fabulous expansion possibilities, this property is ready for its next chapter. Enjoy being just steps away from Chester's vibrant village center, known for its boutiques, acclaimed restaurants, art galleries, theater and the historic Chester Ferry crossing the Connecticut River.

2 Beds ⋅ 2 Baths ⋅ 24185639 MLS

Multiple offers - Seller requests highest and best, Monday, 7/27 by 5PM. No escalation clauses. Fantastic Opportunity in the Heart of Chester! Discover the potential of this charming 2 Bedroom, 1.5 bath ranch, perfectly situated within walking distance to downtown Chester. The highlight of this home is a newer, heated sunroom boasting wood floors, cathedral ceilings and an abundance of natural light overlooking a private 2.39 acre lot. The partially finished, walk-out lower level offers excellent flexible living space, complete with a half bath (with room to expand to a full shower) and a small kitchenette - ideal for an in-law or guest suite. Key features include: New oil-fired furnace; public water; central air; generator; freshly painted interior, one car garage and storage shed. Bring your updates and vision to life! With fabulous expansion possibilities, this property is ready for its next chapter. Enjoy being just steps away from Chester's vibrant village center, known for its boutiques, acclaimed restaurants, art galleries, theater and the historic Chester Ferry crossing the Connecticut River.

25 Goose Hill Rd, Chester

$500,000

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.

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

$805,000

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.

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

$452,000

One floor living in this well maintained Ranch. 1 Full Bath & One 1/2 Bathroom. Hardwood floors. Fireplace in Living Room. Large Eat-in kitchen with Stainless Steel appliances. Recent upgrades include: New HVAC, New 200 AMP electric panel, new roof, new pellet stove, and remodeled bathroom. Open and level yard with nice plantings. Solar system recently installed to assure reasonable utility costs. All in a quiet neighborhood not far from Chester Village or CT River!

3 Beds ⋅ 2 Baths ⋅ 24190609 MLS

One floor living in this well maintained Ranch. 1 Full Bath & One 1/2 Bathroom. Hardwood floors. Fireplace in Living Room. Large Eat-in kitchen with Stainless Steel appliances. Recent upgrades include: New HVAC, New 200 AMP electric panel, new roof, new pellet stove, and remodeled bathroom. Open and level yard with nice plantings. Solar system recently installed to assure reasonable utility costs. All in a quiet neighborhood not far from Chester Village or CT River!

1 Kirtland Ave, Chester

$460,000

Discover the incredible potential of this custom-built Colonial, ready for your personal style and finishing touches. Designed with comfort and functionality in mind, the main level features a dedicated home office complete with extensive shelving and abundant storage, perfect for staying organized while working from home. Upstairs, you'll find three generously sized bedrooms and two full baths, including a beautifully glass tiled hall bath that adds beachy vibes. The spacious primary suite offers both a walk-in closet and an additional traditional closet, with ample room for a king-sized bed and your favorite furnishings. The bright, functional kitchen boasts an abundance of cabinetry, stainless steel appliances, and the convenience of a first-floor laundry room just steps away, between the kitchen and the powder room. The finished lower level provides valuable additional living space, ideal for a family room, recreation area, home gym, or hobby room, with direct access to the oversized two-car garage. With fresh paint and your personal decorating touches, this home can truly shine. Best of all, you're just a short walk from Chester's picturesque town center, where you'll enjoy charming shops, restaurants, galleries, and community events. Experience firsthand why Chester is consistently celebrated as one of Connecticut's most beloved small towns.

3 Beds ⋅ 3 Baths ⋅ 24192544 MLS

Discover the incredible potential of this custom-built Colonial, ready for your personal style and finishing touches. Designed with comfort and functionality in mind, the main level features a dedicated home office complete with extensive shelving and abundant storage, perfect for staying organized while working from home. Upstairs, you'll find three generously sized bedrooms and two full baths, including a beautifully glass tiled hall bath that adds beachy vibes. The spacious primary suite offers both a walk-in closet and an additional traditional closet, with ample room for a king-sized bed and your favorite furnishings. The bright, functional kitchen boasts an abundance of cabinetry, stainless steel appliances, and the convenience of a first-floor laundry room just steps away, between the kitchen and the powder room. The finished lower level provides valuable additional living space, ideal for a family room, recreation area, home gym, or hobby room, with direct access to the oversized two-car garage. With fresh paint and your personal decorating touches, this home can truly shine. Best of all, you're just a short walk from Chester's picturesque town center, where you'll enjoy charming shops, restaurants, galleries, and community events. Experience firsthand why Chester is consistently celebrated as one of Connecticut's most beloved small towns.

42 Straits Rd, Chester

$515,000

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.

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

$233,600

REO Occupied - NO ACCESS OR VIEWINGS of this property - no interior photos. Please DO NOT DISTURB the occupant. Built in 1974, this one level home offers approximately 1344 finished square feet, two bedrooms and two full baths, fireplace, unfinished basement and attached one car garage. This home sits on an approximate 14810 sqft lot. "As is" cash only sale with no contingencies or inspections. Buyer will be responsible for obtaining possession of the property upon closing.

2 Beds ⋅ 2 Baths ⋅ 24172965 MLS

REO Occupied - NO ACCESS OR VIEWINGS of this property - no interior photos. Please DO NOT DISTURB the occupant. Built in 1974, this one level home offers approximately 1344 finished square feet, two bedrooms and two full baths, fireplace, unfinished basement and attached one car garage. This home sits on an approximate 14810 sqft lot. "As is" cash only sale with no contingencies or inspections. Buyer will be responsible for obtaining possession of the property upon closing.

3 Kirtland Ave, Chester

$616,000

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!

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

$600,000

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.

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

$695,000

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.

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

$470,000

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.

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

$618,000

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.

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

$225,000

1.5+ acre lot, clear cut, open, sunny, with a clean air flow. SE facing with 4-mile view down CT River Valley to Deep River, and Lyme Hills; seasonal partial view of Gillette Castle in Hadlyme. Excellent solar, passive or active potential; 220 volts available at street. Ready to build with approvals in place for 3-bedroom septic, town building department, with Connecticut Water Co. supply line available at the street. Well-engineered and installed driveway roughed in with stone base from street level to elevation at top; highly engineered drainage system adjacent to driveway from top to bottom connected to town road storm drain. No wetlands, no water crossings, no shared access, no intrusive noise. Less than a mile walking via country roads to downtown Chester, and to historic Chester-Hadlyme Ferry. Not a development; no covenants or restrictions specific to lot. Drone footage available https://youtu.be/Ks6ut-XOkng

170533629 MLS

1.5+ acre lot, clear cut, open, sunny, with a clean air flow. SE facing with 4-mile view down CT River Valley to Deep River, and Lyme Hills; seasonal partial view of Gillette Castle in Hadlyme. Excellent solar, passive or active potential; 220 volts available at street. Ready to build with approvals in place for 3-bedroom septic, town building department, with Connecticut Water Co. supply line available at the street. Well-engineered and installed driveway roughed in with stone base from street level to elevation at top; highly engineered drainage system adjacent to driveway from top to bottom connected to town road storm drain. No wetlands, no water crossings, no shared access, no intrusive noise. Less than a mile walking via country roads to downtown Chester, and to historic Chester-Hadlyme Ferry. Not a development; no covenants or restrictions specific to lot. Drone footage available https://youtu.be/Ks6ut-XOkng

11 Kings Hwy, Chester

$495,000

***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.

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

$695,000

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.

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

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