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Welcome home this beautifully redesigned house set on over 2.5 acres in picturesque Chester, a quintessential New England town celebrated for its art, history, music, theater and exceptional dining. Completely renovated for today's lifestyle while retaining its warmth and character, this three-bedroom, 2.5-bath home offers beautifully refinished hardwood floors, 9-foot ceilings and thoughtfully designed living spaces throughout. The main level is ideal for entertaining, featuring an inviting living room with fireplace and sliders opening to a balcony/deck overlooking the property. The stunning new kitchen features quartz countertops, new cabinetry, a center island, new appliances, wine cooler and a charming dining nook. A spacious 17' x 13 room provides wonderful flexibility as a home office, or guest room. An updated half bath completes the main level. Upstairs, the primary suite offers a beautifully remodeled luxury bath and walk-in closet. Two additional bedrooms and a remodeled full bath complete the second floor. The finished lower level adds even more living space with an 11' x 21' family room, interior and direct garage access. The auxiliary generator has you covered for New England winters. Move-in ready and beautifully updated inside and out, this special property combines privacy, space and modern comfort with the charm of one of Connecticut's most desirable small towns. The home you've been waiting for-just in time for the holidays!

3 Beds ⋅ 3 Baths ⋅ 24212291 MLS

Welcome home this beautifully redesigned house set on over 2.5 acres in picturesque Chester, a quintessential New England town celebrated for its art, history, music, theater and exceptional dining. Completely renovated for today's lifestyle while retaining its warmth and character, this three-bedroom, 2.5-bath home offers beautifully refinished hardwood floors, 9-foot ceilings and thoughtfully designed living spaces throughout. The main level is ideal for entertaining, featuring an inviting living room with fireplace and sliders opening to a balcony/deck overlooking the property. The stunning new kitchen features quartz countertops, new cabinetry, a center island, new appliances, wine cooler and a charming dining nook. A spacious 17' x 13 room provides wonderful flexibility as a home office, or guest room. An updated half bath completes the main level. Upstairs, the primary suite offers a beautifully remodeled luxury bath and walk-in closet. Two additional bedrooms and a remodeled full bath complete the second floor. The finished lower level adds even more living space with an 11' x 21' family room, interior and direct garage access. The auxiliary generator has you covered for New England winters. Move-in ready and beautifully updated inside and out, this special property combines privacy, space and modern comfort with the charm of one of Connecticut's most desirable small towns. The home you've been waiting for-just in time for the holidays!

42 Straits Rd, Chester

$579,900

Rare opportunity to own a hard to find multifamily in the beautiful town of Chester! This unique 2 unit property offers space, character and flexibility in a wonderful location, just a short drive to Cedar Lake and approximately a 15 minute walk to charming downtown Chester with its shops, restaurants and small town New England appeal. Unit 1 spans 3 levels and features 3 bedrooms, with 2 upstairs and 1 on the main level, 1.5 baths, hardwood floors, exposed beams in the living room and mini splits for heat and A/C. The half bath is ready to be completed, with the seller leaving the toilet, vanity and lighting for the next owner. Some windows have been replaced and the porch features new decking. Unit 2 offers 1 bedroom, 1 full bath, propane heat and a spacious living room with high ceilings. The bathroom features a new vanity and walk in shower. Each unit enjoys its own separate yard space. Major improvements include a new roof, new septic system and new insulation. The property also has a tankless hot water heater and separate electrical meters. Generator stays! A very large basement provides excellent storage and includes an area a previous owner began framing, along with multiple additional storage spaces. A rare opportunity for an investor or owner occupant looking to enjoy all that Chester has to offer!

4 Beds ⋅ 3 Baths ⋅ 24207359 MLS

Rare opportunity to own a hard to find multifamily in the beautiful town of Chester! This unique 2 unit property offers space, character and flexibility in a wonderful location, just a short drive to Cedar Lake and approximately a 15 minute walk to charming downtown Chester with its shops, restaurants and small town New England appeal. Unit 1 spans 3 levels and features 3 bedrooms, with 2 upstairs and 1 on the main level, 1.5 baths, hardwood floors, exposed beams in the living room and mini splits for heat and A/C. The half bath is ready to be completed, with the seller leaving the toilet, vanity and lighting for the next owner. Some windows have been replaced and the porch features new decking. Unit 2 offers 1 bedroom, 1 full bath, propane heat and a spacious living room with high ceilings. The bathroom features a new vanity and walk in shower. Each unit enjoys its own separate yard space. Major improvements include a new roof, new septic system and new insulation. The property also has a tankless hot water heater and separate electrical meters. Generator stays! A very large basement provides excellent storage and includes an area a previous owner began framing, along with multiple additional storage spaces. A rare opportunity for an investor or owner occupant looking to enjoy all that Chester has to offer!

84-86 Spring St, Chester

$559,000

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

$449,000

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 ⋅ 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

$499,900

Set in the charming town of Chester, this three-bedroom, two-bath home offers a versatile layout with thoughtfully updated spaces throughout. The main level features an updated kitchen, wood floors, and an inviting living room anchored by a striking raised gas fireplace that serves as a beautiful focal point. Recent improvements include a new roof and new central air conditioning condenser, adding to the home's appeal. Step outside to a multilevel deck overlooking the private backyard, creating a wonderful extension of the living space. The lower level adds exceptional flexibility with an ADU featuring its own private entrance, along with a separate laundry room and access to the two-car garage. Whether used for additional living space, guests, a home office, or other needs, the layout offers plenty of possibilities. Just a short distance from Chester Village, known for its acclaimed restaurants, independent shops, galleries, and distinctive small-town atmosphere. A unique opportunity to enjoy flexible living, outdoor space, and all that Chester has to offer.

3 Beds ⋅ 2 Baths ⋅ 24202647 MLS

Set in the charming town of Chester, this three-bedroom, two-bath home offers a versatile layout with thoughtfully updated spaces throughout. The main level features an updated kitchen, wood floors, and an inviting living room anchored by a striking raised gas fireplace that serves as a beautiful focal point. Recent improvements include a new roof and new central air conditioning condenser, adding to the home's appeal. Step outside to a multilevel deck overlooking the private backyard, creating a wonderful extension of the living space. The lower level adds exceptional flexibility with an ADU featuring its own private entrance, along with a separate laundry room and access to the two-car garage. Whether used for additional living space, guests, a home office, or other needs, the layout offers plenty of possibilities. Just a short distance from Chester Village, known for its acclaimed restaurants, independent shops, galleries, and distinctive small-town atmosphere. A unique opportunity to enjoy flexible living, outdoor space, and all that Chester has to offer.

55 Wig Hill Rd, Chester

$269,900

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! One of the parties to the LLC has an active real estate license

3 Beds ⋅ 1 Baths ⋅ 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! One of the parties to the LLC has an active real estate license

92 Water St, Chester

$254,900

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! One of the parties to the LLC has an active real estate license.

1 Beds ⋅ 1 Baths ⋅ 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! One of the parties to the LLC has an active real estate license.

90 Water St, Chester

$475,000

NEW PRICE!! Beautiful view from this WATERFRONT home on Chester Cove! Steps to fishing or kayaking just out your door. Enjoy watching the wildlife from the 20x10 deck directly off the kitchen/dining/living rooms. Wonderful light enters through the abundant windows on the first floor with its open floor plan, kitchen with granite, newer appliances and a window over the kitchen sink you won't want to walk away from; there's also sliders to the deck and a full bath. On the second floor there are three spacious bedrooms along with a second full bath. The whole house underwent full renovations between 2012-2013 including new kitchen, baths, gleaming oak flooring, foam insulation, new HVAC, new electrical; the updates continued along with a new roof in 2017, and just recently new carpeting on second floor, new stove and microwave plus a new dryer. Bring your creativity to finish the lower walk-out level with its charming brick architecture along with newer radiant-heated, poured concrete floors and french doors -- this could be an amazing walkout steps to the water! This house would be a perfect vacation rental.... Rent a few weeks/Stay a few weeks!

3 Beds ⋅ 2 Baths ⋅ 24189125 MLS

NEW PRICE!! Beautiful view from this WATERFRONT home on Chester Cove! Steps to fishing or kayaking just out your door. Enjoy watching the wildlife from the 20x10 deck directly off the kitchen/dining/living rooms. Wonderful light enters through the abundant windows on the first floor with its open floor plan, kitchen with granite, newer appliances and a window over the kitchen sink you won't want to walk away from; there's also sliders to the deck and a full bath. On the second floor there are three spacious bedrooms along with a second full bath. The whole house underwent full renovations between 2012-2013 including new kitchen, baths, gleaming oak flooring, foam insulation, new HVAC, new electrical; the updates continued along with a new roof in 2017, and just recently new carpeting on second floor, new stove and microwave plus a new dryer. Bring your creativity to finish the lower walk-out level with its charming brick architecture along with newer radiant-heated, poured concrete floors and french doors -- this could be an amazing walkout steps to the water! This house would be a perfect vacation rental.... Rent a few weeks/Stay a few weeks!

135 Middlesex Ave, Chester