63 properties for sale in Shailerville

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Step back in time without giving up a thing. The John Ventres Jr. House is a classic antique Colonial in Haddam, just minutes from the Connecticut River, and two centuries of character come with the big updates already done: a brand-new roof this year and a new septic system in 2025. Inside, hand-hewn beams, wide-plank pine floors, a brick chimney, and cast-iron radiators tell the home's story, while fresh paint throughout and newer carpeting make it move-in ready. The kitchen pairs creamy white cabinetry and stone counters with a wood-topped island, stainless appliances, and under-cabinet lighting, and it opens to a generous dining room for gatherings. A sunroom with a wood stove is the spot for cozy winter evenings. The first-floor bedroom sits near a full bath and a dedicated laundry room. Upstairs are three more bedrooms, an office, and a second full bath, plus a walk-up attic and a full basement for storage. Out back, the wraparound deck steps down to a stone patio and a private,

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Opportunity knocks! This fixer-upper is reasonably priced and affords first time home buyers or investors the chance to roll up their sleeves and create the home of their dreams. All mechanicals and appliances are in working order so you can move in and update at your own pace! Set on a beautiful, level lot, this 3 bedroom, 2.5 bath home features two fireplaces, soaring cathedral ceilings in the living room, hardwood flooring on most of the main level, replacement windows, newer water heater, wired for a generator, a large rear deck and a two car garage

13-Acre Secluded Country Oasis nestled in the beautiful Connecticut countryside, offering privacy and an extraordinary connection to nature. Set on a lovely pond with a dock ideal for kayaks, canoes or a rowboat, the property features a gorgeous waterfall cascading into the Ponset Brook. It is truly like living inside a postcard with nature and tranquility. The charming 8-room home features beautiful hardwood floors and inviting spaces throughout. A spectacular oversized office boasts a wall of windows overlooking the waterfall and a second wall lined with built-in bookcases-an inspiring setting for work, reading or simply enjoying the ever-changing beauty of nature. A portion of the home was once a historic button factory and has been thoughtfully incorporated into the residence as a wonderful family room, adding character and a unique sense of history. The property also includes a large barn style garage with a second-floor workshop and office, a convenient two-car garage and an addi

Tucked away in one of Higganum's most sought-after neighborhoods, this beautifully maintained hip-roof Colonial offers exceptional privacy, with woods and open space bordering three sides of the property. Thoughtfully positioned when built in 2014 to take full advantage of the serene setting, the home makes a lasting first impression. Guests follow the walkway to the front door passing beautiful landscaped grounds and enter into a spacious foyer, while everyday entry is through the attached two-car garage with durable epoxy flooring. Kick off your shoes in the thoughtfully designed mudroom featuring custom cubbies, bench seating, and coat hooks. From there, the home opens to inviting living spaces ideal for both daily living and entertaining. The kitchen serves as the heart of the home with white cabinetry, a contrasting center island, granite countertops, and stainless steel appliances, flowing seamlessly into the family room with its updated fireplace, raised hearth, and custom built

Re-imagined in partnership with Old Lyme's Nautilus Architects, this exceptional Whalebone Cove property offers commanding views, dock access and a rare connection to nature. A stone and pebble drive winds through mature woodlands and an orchard to park-like grounds dotted with native and specimen plantings, descending to the Cove. Thoughtfully designed for beauty, sustainability and long-term ease of living, this quietly stunning home boasts custom millwork, cedar-lined cabinetry and exceptional materials throughout. A barrel-vaulted entry beneath an 18th-century German stained-glass window leads to wonderfully versatile spaces. First, the main level vaulted kitchen, great room and dining area with a professional copper hood, soapstone sink, onyx accents and wood-burning fireplace, all illuminated by western sunsets. Ipe decks and bluestone patios with pergolas create inviting spaces to entertain. Accessibility is seamlessly integrated with level thresholds, widened doorways and an el

Selden Farm, a landmark 1690s property steeped in history and set in a picturesque corner of Lyme, is once again available for new stewardship. Upheld by only three families since 1695 when it sat on over 6,000 acres, it presents a rare opportunity to own a beautiful country Antique home now set on 9 pastoral acres abutting conservation land with sweeping views of Selden Cove and the CT. River. At its heart is a gracious and authentic 5-bedroom Colonial which exudes history, charm and character. House features include a tavern room, wide board floors, original paneling and moldings, 6 fireplaces and an abundance of windows which invite lovely views and light into each room. Adjacent to the home is a 3-bay garage with self-sufficient guest accommodation for visiting family and friends. Dotted throughout the property are a renovated barn used as a studio/office/ gym, several outbuildings, a greenhouse and sunny open meadow for animals or farming. Two privately situated guest houses (one

Pride of ownership will wow you at 15 Davison Rd in Moodus! This spectacular colonial home sits on over an acre of private land on a quiet, dead-end road lined with quintessential New England stone walls! This home features a sprawling, open floor plan with over 4,000 sq ft of flexible living space for all your needs. With 4 bedrooms, 2.5 baths, a 2-car garage, a living room, family room, recreation space and a dedicated gym area, you'll never want to leave! Enjoy outdoor living at its finest with beautiful views, serenely tucked in nature, a huge stone patio, and a sprawling deck off the breakfast nook. Neutral paint hues and gleaming hardwood floors make this home warm and inviting. Kitchen features granite countertops, stainless steel appliances and a plethora of cabinetry for all your storage needs as well as a large center island. Natural light spills into the expansive living room area off the kitchen and a propane fireplace adds warmth on cold New England nights. A large dining

Charming traditional 3-bedroom Colonial home located on quiet country and very scenic town road minutes to the newly renovated East Haddam historical swing bridge. This impeccably kept home is in move in condition. Perfectly and newly painted with neutral color pallet throughout and nice bright flat ceilings. New plumbing updates, electrical and brand-new carpeting upstairs! Upon entering to the left you will be delighted to see the front to back formal living room with a real masonry fireplace, gorgeous gleaming hard wood flooring and plenty of sunlight with the oversized thermal paned Anderson windows which would cost $1000 a window today. The spacious kitchen is in the back of the home with an island, pantry, separate closet space and hardwood flooring. The side door to the new deck opens to a world of abundant nature and a conservation preserve to explore! French doors to the pretty formal dining room with hardwood flooring. The master bedroom suite is on the upper level to the lef

Brand new home being constructed now- on great private lot. This home is will be situated on about 2 acres of sprawling space. Colonial style home with over 2500 sq ft of space featuring 4 bedrooms, 3 baths and open bright modern concept. Home features combination kitchen and dining layout with 9' ceilings and center island with large slider to exterior and lightly wooded private yard. Well designed family room and floor plan offers 4 large bedrooms and full bath on one side of home and a primary en-suite on other side of home making floor plan scaled correctly. Other misc features include a 3 car garage, plenty of storage and ability to customize. Home will take 8-10 months to construct. Please note - photos of the home shown are of same home builder recently built. This home is a to be built home and individual color choices will be selected by buyer. builder has finished home available to tour on 1 Quinn way in East Hampton - please text list agent for pricing on this and access Ple

13-Acre Secluded Country Oasis nestled in the beautiful Connecticut countryside, offering privacy and an extraordinary connection to nature. Set on a lovely pond with a dock ideal for kayaks, canoes or a rowboat, the property features a gorgeous waterfall cascading into the Ponset Brook. It is truly like living inside a postcard with nature and tranquility. The charming 8-room home features beautiful hardwood floors and inviting spaces throughout. A spectacular oversized office boasts a wall of windows overlooking the waterfall and a second wall lined with built-in bookcases-an inspiring setting for work, reading or simply enjoying the ever-changing beauty of nature. A portion of the home was once a historic button factory and has been thoughtfully incorporated into the residence as a wonderful family room, adding character and a unique sense of history. The property also includes a large barn style garage with a second-floor workshop and office, a convenient two-car garage and an addi

Welcome to 25 Carriage Drive, a beautifully situated 4-bedroom, 2.5-bath home nestled on a private-feeling rear lot surrounded by woods and protected land, offering a peaceful and secluded setting. Inside, you'll find a bright, open layout featuring hardwood floors, all-new carpeting, freshly painted, a spacious open kitchen, and an inviting fireplace that creates the perfect gathering space. Generously sized bedrooms provide plenty of room for everyone, while the primary suite offers a relaxing retreat complete with a walk-in closet and private full bath. The finished full basement provides additional living space with endless possibilities for a family room, home office, recreation area, or gym. A two-car garage adds convenience and plenty of storage. Located in the desirable lake community of East Hampton, you'll enjoy all the charm and recreation the area has to offer, including access to beautiful Lake Pocotopaug. With its spacious interior, wooded surroundings, and wonderful loca

Experience luxury and privacy in this new construction estate set on 3.24 secluded acres in East Haddam, surrounded by protected open space. Offering over 6,000 sq ft, this custom home combines refined craftsmanship with modern comfort. The layout includes 5 bedrooms, 4.5 baths, and 3 fireplaces, creating warm, inviting spaces perfect for both everyday living and elegant entertaining. A chef's kitchen with premium cabinetry and stone counters opens to expansive living and dining areas flooded with natural light and serene wooded views. The first-class primary suite features a spa-inspired bath and generous walk-in closets. Additional flexible rooms allow for a home office, media space, or library, and high-end finishes elevate every detail throughout the home. The property provides ample room for future outdoor enhancements such as a pool, patio, or gardens, offering endless possibilities for creating your ideal retreat. This rare setting delivers unmatched tranquility while remaining

This is not your typical older home! Built in 1930 for the local doctor, this distinctive Colonial beautifully blends the craftsmanship and character of its era with thoughtful updates for modern living. With just three owners, this well-maintained home reflects a tradition of pride in ownership. An inviting foyer with an impressive staircase welcomes you to hardwood floors, custom moldings, generously sized rooms and beautifully crafted built-ins. The expansive living room features a fireplace and handsome built-ins, while the formal dining room showcases elegant picture-frame wainscoting, perfect for family dinners and special occasions. The updated kitchen offers granite countertops, stainless steel appliances, an electric double-oven range and pantry. An extra-wide breakfast bar opens to the adjoining eating area, where sliders overlook the backyard. A unique feature is the doctor's former office, now a spacious 23' x 18' family room with its own entrance, cathedral ceiling, impres

Welcome to this beautifully maintained 4-bedroom, 5-bath Colonial, set on 2.9 beautifully landscaped, private acres in a desirable neighborhood, offering a wonderful blend of space, privacy, and natural beauty. The updated kitchen features granite countertops and offers a wonderful space for everyday living and entertaining. Hardwood floors throughout add warmth and timeless charm, while the formal dining room is enhanced by elegant crown molding. One of this home's exceptional features is its two spacious primary suites, each offering a walk-in closet and private full bath. The additional bedrooms and baths provide plenty of flexibility for family, guests, or a home office. Enjoy the peaceful surroundings from the large deck overlooking the beautifully landscaped backyard, which abuts protected nature conservancy land that will remain undeveloped. This special setting offers a wonderful sense of privacy, scenic natural surroundings, and the enjoyment of nature right beyond your backya

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

Spacious and versatile 4-bedroom, 2-bath home offering approximately 1,842 square feet of living space with a flexible layout and plenty of possibilities. Currently used as a single-family home, the upper and lower levels provide separate living spaces, (multi generational living) offering added privacy and flexibility. The property features two oil tanks and two electrical panels and may offer potential for a two-family setup, subject to town approval and buyer due diligence. Situated on approximately one acre with a private well and septic, this home offers plenty of room and opportunity for its next owner to make it their own

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. Zoned R

Step into timeless charm and craftsmanship in this distinctive home, where they truly don't make them like they used to! Wide decorative baseboards, classic doors, detailed trim, stained-glass windows, and a welcoming covered front porch showcase its character. The original stone fireplace feels straight out of a fairytale book, creating a warm and inviting focal point. The dining room features a built-in hutch and cabinetry, while hardwood floors run throughout, including beneath all carpeting. A versatile first-floor room offers a beautiful picture window and built-in window seat with storage, creating the perfect spot for reading or relaxing. The first floor also features a walk-in laundry room with the added convenience of a toilet, along with a kitchen located just off the driveway for easy access. Enjoy the outdoors from the covered front porch or back deck. Upstairs, the oversized primary bedroom boasts vaulted ceilings, three generous closets, abundant natural light, and hardwo

A unique opportunity, 2 Homes on 1 Lot. Plus a barn/garage. First Home has 2 bedrooms and is 1,061 sqft. Second Home has one bedroom and is 350 sqft. Separte town water and sewer to each home. Ready for your updating! Electric 100 AMPS each

A stabilized apartment complex just one half mile from the picturesque downtown of Chester, CT. This property features a strong CAP ex profile including a new roof, electrical service, and well water treatment system. A 6% CAP rate is projected at entry assuming fully burdened vacancy, maintenance, and management figures. Each unit pays their own electric bill which includes the cost of heat and hot water. The owners pay for the dumpster, well water and treatment, the common electric bill, taxes, and insurance. Three of the seven residential units in the main building have washer and dryer hookups and there is off street parking for all units. A 1,500 square foot warehouse is positioned along the driveway at the base of the hill

A truly special Chester Village treasure! Beautifully nestled in a private, peaceful neighborhood on a desirable cul-de-sac with no through traffic. This pristine home offers an exceptional blend of timeless character, refined comfort, and an enviable location less than a half-mile stroll to Historic Downtown Chester. From the moment you enter, the warmth and elegance are unmistakable. The gracious living room features a stunning paneled wall, gorgeous fireplace, and beautiful wide board hardwood floors. The elegant formal dining room is perfect for intimate dinners or festive gatherings. The inviting kitchen is a true focal point, offering a generous island with granite countertops and its own fireplace. Three bedrooms and two full baths are privately located on the second floor, while convenient main-level laundry adds to the ease of everyday living. The newly finished lower level provides versatile living space-ideal for a family room, media room, office, gym, or private retreat. Tw

PRICE IMPROVEMENT JUST IN TIME FOR THE HOLIDAYS! Discover the charm of Chester, one of Connecticut's most picturesque New England towns, celebrated for its vibrant arts scene, theater, unique boutiques, and exceptional dining. Set on over 2.5 private acres, this beautifully renovated 3-bedroom, 2.5-bath home is an ideal year-round residence or weekend retreat for those looking to escape the hustle and bustle of city life. Thoughtfully redesigned with modern finishes while preserving its warmth and character, this home features 9-foot ceilings, refinished hardwood floors, and inviting living spaces. The main level includes a spacious living room with fireplace and sliders opening to a deck overlooking the scenic grounds. The stunning new kitchen features quartz countertops, new cabinetry, center island, new appliances, wine cooler, and charming dining nook. A generous 17' x 13' bonus room offers wonderful flexibility for a home office, guest space, or additional living area. Upstairs, t

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

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 floo

Welcome home to this meticulously maintained Cape Cod-style residence, nestled on a tranquil cul-de-sac just steps from vibrant Chester Village. Cherished by the same owner for over 34 years, this home radiates pride of ownership, classic charm and everyday functionality. The main level features gleaming hardwood floors and a beautifully updated kitchen; complete with granite countertops, newer stainless steel appliances, a breakfast bar, and French doors providing access to the deck and private backyard. The seamless flow leads into a light-filled living room anchored by a cozy pellet stove, a formal dining room, and a generous laundry/pantry room with custom built-ins. A main-floor bedroom and full bath offer flexible options for guests, main-level living, or a dedicated home office. Upstairs, find two spacious bedrooms, including a primary suite with its own private bath. The second bedroom boasts a walk-in closet plus a separate oversized dressing/flex room. The lower level feature

A Unique opportunity, 2 Homes on 1 Lot. Plus a barn/garage. First Home has 2 bedrooms and is 1,061 sqft. Second Home has one bedroom and is 350 sqft. Separate town water and sewer to each home. Ready for your updating! Electric 100 AMPS each

Enjoy Lake Living at Hidden Lake in rural Haddam. Just a short walk to the beach, this charming home offers an open and flexible floor plan. This home was expanded in 2000 with a full second floor addition. It has a first floor bedroom and full bath, as well as 2 additional bedrooms, full bath and second floor living area. The layout offers the flexibility to accommodate guests, and possible in-law accommodations. Split heat pump system offers AC and heat. Additionally there are baseboards throughout and a propane stove in the basement. Full basement and shed offer good storage. 200 Amp electric with generator hook-up. Hidden Lake is a block away and available for Association members and their guests. Available activities are swimming, fishing, boating (electric motors only), ice skating and ice fishing. There are three beaches. The closest is Shore Beach at the end of either Shore Drive or White Birch Trail. East Shore Beach and West Shore Beach are also available. Hidden Lake Associa