60 properties for sale in Shailerville

A distinctive board and batten exterior gives this inviting home a warm, rustic character that stands apart from your typical colonial, all set on a generous two acre lot with a backdrop of peaceful woods. Interior immediately impresses with a spacious front to back living room featuring a fireplace and French doors that draw in natural light. The kitchen is a true gathering space, offering a gas stove, granite counters, an island, and an eat in area with hardwood floors, all flowing seamlessly into the hardwood clad dining room. From there, step into the expansive 16X20 screened in porch with vaulted ceilings-an ideal spot to enjoy views of the private back lawn and surrounding woods. As you ascend the stairs, four comfortable bedrooms and full bath complete the second floor. The villages of Haddam, Higganum and Tylerville are an outdoor enthusiasts dream with State Parks for hiking and biking as well as the Higganum Cove, Haddam Meadows and area marinas to boat or to just appreciate

Welcome to 128 Killingworth Road, Higganum (Haddam)-a captivating contemporary country retreat where privacy meets spacious modern living. Nestled on an expansive and serene 3.1-acre wooded lot, this unique 2,577-square-foot home seamlessly blends mid-century character with flexible everyday functionality. Boasting 3 comfortable bedrooms, 2.5 baths, and an inviting 8-room layout, the interior features an open atmosphere anchored by a cozy fireplace and wrapped in natural light. Outside, the park-like grounds and mature landscaping offer a peaceful sanctuary from the daily hustle, while still keeping you close to local conveniences and major highways. Whether you are hosting weekend gatherings on the deck or unwinding in your own private slice of Middlesex County nature, this property offers an exceptional canvas for your next chapter FEATURES Custom Chefs kitchen. 4 season sunroom with separate zone radiant heat. Completely renovated 2022. New Roof 35 yr shingles. Recently painted insi

Classic Colonial set on 1.7 acres, offering the perfect blend of space, comfort, and a connection to nature. The backyard has been thoughtfully left natural, creating a peaceful setting for birds and wildlife, while the expansive, level side yard has been the perfect spot for countless football games, outdoor activities, and gatherings. Bordering a cul-de-sac street, this property offers the best of both worlds: room to play and entertain, along with a tranquil natural setting. Inside, hardwood floors highlight the first-floor formal living and dining rooms, while the back of the home features an inviting open-concept eat-in kitchen and family room with fireplace. The primary bedroom suite includes an additional room currently used as an office, offering flexibility for a nursery, dressing room, or private retreat. A fourth bedroom over the garage provides extra space for guests, a large sleeping area, or a versatile bonus room. Second-floor laundry adds everyday convenience, while the

SELLER FINANCING AVAILABLE WITH A POTENTIAL 5.25% INTEREST RATE FOR QUALIFIED BUYERS!* A rare opportunity to purchase a beautifully updated home with attractive financing options that could offer significant monthly savings compared to traditional mortgage financing! Welcome to 882 Killingworth Road, a 4-bedroom, 3-bath Colonial situated on two private acres in the heart of Haddam. Offering 2,286 sq ft of living space, this home blends classic New England charm with modern updates, including refinished hardwood floors and a bright, open layout ideal for everyday living and entertaining. The well-appointed kitchen flows seamlessly into the dining and living areas, with sliding glass doors leading to a newly installed stone patio overlooking the in-ground pool and expansive yard. A standout main-level primary suite features a spacious bathroom with walk-in shower, tile flooring, convenient laundry setup, and a generous walk-in closet. Upstairs, three additional bedrooms share a full bath

Set on 6.7 acres bordered on three sides by Cockaponset State Forest, this distinctive property combines wooded privacy with a shared pond, a flowing river on the land, and access to the Blue Trail hiking network. Imagine quiet mornings surrounded by mature trees, the gentle sound of moving water, birdsong, and peaceful outdoor moments with nature as your backdrop. The setting is suited to a full-time residence or second home, with opportunities to hike, explore the woods, and enjoy a country setting near Connecticut River towns and coastal destinations. The 1976 Saltbox Colonial was extensively renovated, with a 2008 addition doubling the original home's size. Features include hardwood floors, Anderson windows, quartz kitchen countertops, and appliances. Double Anderson doors open onto the deck. The flexible two-to-four-bedroom layout includes a first-floor bedroom or office, laundry, and full bath. The primary suite has a walkout deck and full bath with jetted tub. Two additional bed

New construction with farmhouse character and room to make it your own in Higganum's Chatham Lake community! Set on 2.27 acres, this 2,918 square foot Colonial offers 4 bedrooms, 2.5 baths and an attached 2 car garage. A covered front porch welcomes you inside to hardwood floors, a dedicated office and a separate dining room. The kitchen connects to a spacious breakfast nook and a great room with a gas fireplace and coffered ceiling, creating an inviting setting for everyday living and entertaining. Sliders lead from the breakfast nook to a rear patio, while a mudroom with a built-in bench provides a convenient entry from the garage. Upstairs, the primary suite features two walk-in closets and private bath with a double vanity, soaking tub and separate shower. Two additional bedrooms are complemented by a generous finished bonus room above the garage, offering space for a fourth bedroom, family room or recreation room. An open loft, second-floor laundry and another full bath complete t

Modern farmhouse design meets refined craftsmanship in this exceptional to be built offering in the highly desirable Chatham Lake neighborhood. Positioned atop a gentle rise, this higher-sitting homesite captures beautiful ridgeline views and stunning sunset views from the front of the home, creating a setting that's difficult to replicate. Buyers have the opportunity to choose between two distinctive home designs, each offered at $1,250,000. The featured plan offers 3,689 sq ft, 5 bedrooms, 3.5 baths, a dedicated first floor office and oversized great room. An open concept main level centers around the spacious great room with fireplace and coffered ceiling, flowing into the custom kitchen and dining area with an oversized island and butler's pantry. Upstairs are four bedrooms plus a large bonus room that may also serve as a fifth bedroom, along with three full baths and second floor laundry. Prefer a first floor primary suite? The alternate 3,528 sq ft Ridgeview design is also availa

Charming, well-maintained ranch in a private cul-de-sac setting with no immediate neighbors, offering easy one-floor living. This home features beautiful hardwood floors throughout, two fireplaces, and remodeled bathrooms. Major updates include a roof that is only six years old, furnace installed around 2019 and newer central air conditioning for added comfort and peace of mind. Additional highlights include a generator hookup in the garage, oil heat, and a walk-out basement providing valuable extra living space, perfect for a family room, home office, gym, or guest area. Enjoy the quiet, private location while still being conveniently close to local amenities. This home combines comfort, privacy, and practical updates, making it truly move-in ready

So much POTENTIAL here. Over 2 acres steps to Hidden Lake Association! 2400+ square ft home offering 4 bedrooms and 2-1/2 baths along with an oversized detached 2 car garage with finished space above perfect for in-home office, studio or in-law apartment! The open kitchen and dining areas are spacious with lots of windows to let the light indoors; large living room with fireplace; a separate family room just off the kitchen. On the second floor you'll find 4 bedrooms - the primary en-suite bedroom offers cathedral ceiling, a spiral stairway to a loft area! Accessible here are two separate SPACIOUS attic areas. In addition to the above, you will find a separate oversized two-car garage with an in-law suite and large deck on the second level perfect for family stay-overs, in-home office, etc. A lot of house, property and extra living quarters on a huge 2 acre lot - TLC and elbow grease needed - bring your plans, paint, tools to make this property your dream home - STEPS TO HIDDEN LAKE! P

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

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

Looking for an amazing house by the CT River' Look no further than this fabulous house! Enjoy views from almost every room in every season. 1192 Sq Ft additional lower level with full walk out.When you enter into the spacious foyer you will be wowed by the grand curved staircase, then a few steps down into the living room cathedral ceilings, bar, built in wine cabinet holding approx 280 bottles of your favorite reds and whites, sliders to the 3 season porch, built in cabinet and see through fireplace, all with a view. Round the corner through the arched entry to your dining room where the fireplace comes through for warmth and ambience while dining. With palladium and transom windows, a slider to the deck and high ceilings, this room is bright and airy. Take a couple steps up to the kitchen equipped with cherry cabinets, a gas cooktop with griddle, custom paneled refrigerator, granite counters, a dining nook and a pantry room with built ins and washer/dryer. The first floor also includ

Nestled behind the circular driveway and surrounded by curated landscaping, this exceptional French Normandy country home offers a rare combination of architectural charm, artistic vision, quality craftsmanship and complete privacy. With 4,000 square feet of living space, the residence features five bedrooms and five baths, a beautiful modern kitchen, dining room with wet bar and large living room with vaulted ceilings and a magnificant fireplace. There is a second fireplace in the family room adjacent to the kitchen which opens to the backyard. These spaces are all thoughtfully designed for both elegant entertaining and comfortable everyday living. The expansive primary bedroom suite is on the main floor and opens to a dedicated outdoor sitting area. The home and grounds have been created and refined over many years by owner, Ward Stegerhoek, a Dutch innovator and artist well-known in the fashion industry whose unique aesthetic is reflected inside and out. Every view has been carefull

Welcome to 44 Haddam Neck Road! This charming raised ranch offers 3 bedrooms, 2 full bathrooms, and 1 half bathroom, situated on approximately 0.78 acres in East Hampton. Inside, you'll find a warm and inviting atmosphere with beautiful hardwood floors, natural wood accents, and plenty of natural light throughout. The spacious living room features a brick fireplace, while the adjoining dining area provides a comfortable setting for everyday meals and gatherings. All three bedrooms offer generous space and comfortable layouts, with the primary bedroom featuring the added convenience of its own private en-suite bathroom. The finished lower level provides additional living space, complete with a family room, wood-burning stove, and built-in bar area, offering a great setting for entertaining or relaxing at home. A separate laundry room adds everyday convenience, while the attached two-car garage provides additional parking and storage. Outside, the elevated rear deck overlooks a spacious

Where Architectural Inspiration Meets the Majesty of the Connecticut River. Perched majestically on 15.22 acres along the eastern bank of the Connecticut River, 89 River Road offers a rare convergence of architectural pedigree, natural beauty, privacy, and fully realized lifestyle design. Designed, owned, and meticulously crafted by one of America's leading architects, this 12,836-square-foot, three bedroom compound, completed in 2018, was conceived to inspire creativity, wellness, and a connection to the outdoors. Protected by parkland, Nature Conservancy, and Land Trust preserves, the heart of the home is defined by extensive, floor-to-ceiling glass walls that command uninterrupted, panoramic vistas of the Connecticut River while a scenic jeep road offers direct access to Chapman Creek and the River beyond. A seamless flow connects the breathtaking entertaining and living areas with a variety of outdoor decks and terraces. The estate offers a rare sanctuary designed to fuel both the

Farmhouse on a nice half acre lot with Endless potential. 6 rms 2-3 bedrooms. Hardwood floors throughout. New roof. New well installed approximately 12 yrs. ago, per owner. House Needs work, but, well worth the effort. Cash or rehab financing only. House being sold in AS IS condition

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

EXCEPTIONAL NEWLY COMPLETED CONSTRUCTION - LUXURY, CRAFTSMANSHIP and TIMELESS ELEGANCE! Perched on an elevated 2.31-acre homesite in a desirable cul-de-sac neighborhood, this stunning 3,500 sq. ft. custom residence offers 4 bedrooms, 3 1/2 baths and an oversized 3-car garage. A dramatic two-story foyer with floor-to-ceiling picture-frame molding sets the tone for the exceptional craftsmanship throughout. Enjoy 9-foot ceilings on all three levels, hardwood floors, custom millwork, tray and coffered ceilings, and a beautifully appointed great room with gas fireplace. The chef's kitchen showcases premium Thermador appliances, a six-burner range, custom ceiling-height cabinetry, quartz countertops and backsplash, and a striking waterfall peninsula. An impressive butler's pantry features French doors, custom cabinetry and a prep sink. The luxurious primary suite offers a tray ceiling, spacious walk-in closet and spa-inspired bath with custom-tiled shower. A fourth bedroom with private bath

Welcome to 128 Killingworth Road, Higganum (Haddam)-a captivating contemporary country retreat where privacy meets spacious modern living. Nestled on an expansive and serene 3.1-acre wooded lot, this unique 2,577-square-foot home seamlessly blends mid-century character with flexible everyday functionality. Boasting 3 comfortable bedrooms, 2.5 baths, and an inviting 8-room layout, the interior features an open atmosphere anchored by a cozy fireplace and wrapped in natural light. Outside, the park-like grounds and mature landscaping offer a peaceful sanctuary from the daily hustle, while still keeping you close to local conveniences and major highways. Whether you are hosting weekend gatherings on the deck or unwinding in your own private slice of Middlesex County nature, this property offers an exceptional canvas for your next chapter FEATURES Custom Chefs kitchen. 4 season sunroom with separate zone radiant heat. Completely renovated 2022. New Roof 35 yr shingles. Recently painted insi

RESORT-STYLE LIVING IN THE HEART OF HIGGANUM! Discover an extraordinary private retreat tucked away at the end of a peaceful cul-de-sac, surrounded by mature, professionally designed landscaping. This exceptional property combines luxury, privacy, and breathtaking outdoor living. THE ULTIMATE BACKYARD PARADISE features a spectacular heated gunite infinity pool with granite-topped vanishing edge, integrated whirlpool spa, custom stonework, and expansive travertine patio. A stunning cedar-sided post-and-beam pool house with wood-burning fireplace and dramatic glass garage door creates the perfect entertaining destination. Inside, discover exceptional European craftsmanship, premium Rohl, Grohe, Geberit and Duravit fixtures, solid maple cabinetry, granite countertops, custom tilework, and hardwood closet organizers. The gourmet kitchen showcases Sub-Zero refrigeration, freezer and wine storage, Wolf cooking appliances, and oversized island. Premium plumbing fixtures by Rohl, Grohe, Geberi

Space, flexibility, and a peaceful setting come together in this inviting 4-bedroom, 3-full-bath Colchester home! Offering 2,899 sq ft of living space and a large yard bordering preserved State of Connecticut land, this property combines privacy, comfort, and versatility. The thoughtfully designed floor plan includes a desirable first-floor bedroom with its own exterior entrance and nearby full bath, ideal for guests or flexible living arrangements. A separate first-floor office or flex space and spacious mudroom with laundry add everyday convenience. Upstairs, the primary suite offers a private retreat with a full bath and walk-in closet. The finished lower level provides additional space for entertaining or relaxing, with a slider leading to a covered patio. Enjoy outdoor living with two separate decks, a covered patio, and a spacious yard surrounded by nature. An oversized 1-car garage adds convenience. Located near Salmon River, Pickerel Lake and Day Pond State Park, with opportuni

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 s

The Johnathan Warner house, and later known as the Warner-Brooks House was built by Johnathan Warner in 1798 and is a remarkable testament to early American prosperity, craftsmanship, and vision. Listed on the National Register of Historic Places, this exceptional Federal-style residence retains extraordinary architectural integrity. Heavily documented during construction are original bills, receipts, and construction records documenting the artisans materials, suppliers, and methods used to create this architectural masterpiece. Revered by historians and preserved with exceptional care, this irreplaceable legacy property offers a rare opportunity to own one of Connecticut's most significant surviving Federal residences. A once-in-a-generation opportunity to become the steward of one of the Connecticut River Valley's most important historic estates. Jonathan Warner was the founder of the Chester-Hadlyme Ferry which is right down the road and is still in operation today. Johnathan was a

Just a quick stroll from the heart of Chester Village, this absolutely charming three-bedroom, one-bath home offers a wonderful combination of classic character, recent improvements, and an exceptional location. From the moment you arrive, the inviting enclosed front porch welcomes you, providing additional living space and a wonderful spot to relax. Inside, the home retains much of its original charm, with beautiful hardwood floors, rich wood moldings throughout, and a lovely built-in corner hutch in the dining room. The kitchen has been updated from its original design, offering modern convenience while complementing the home's character. Recent improvements in 2026 include a freshly painted interior, refinished hardwood floors, and a professionally waterproofed basement. A walk-up attic offers potential for future expansion or additional storage. Situated on just under half an acre and only 0.2 miles from downtown, you'll enjoy easy access to Chester's wonderful restaurants, art gal

Good design is all about the details and this beautifully appointed New England Cape offers the perfect balance of traditional features with modern home design. Custom built and offering desirable one floor living, a warm and welcoming entrance leads to spacious well-proportioned rooms that blend seamlessly with the natural surroundings. The Chef's kitchen features rich wood cabinetry, stainless steel appliances, granite countertops and opens to a casual dining area. perfect for everyday gatherings. Sliders lead to the sun-filled private deck and is ideal for outdoor entertaining. The formal living room, centered around the wood burning fireplace, features crown moldings, 9 ft ceilings, gleaming hardwood floors and inspires a lifestyle of quality and comfort. A true highlight is the spacious first floor primary suite with a beautifully appointed bath, walk-in-closet and French doors opening to the deck. A half bath and mudroom complete the main level and the two car over-sized attach g

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

Modern farmhouse design meets refined craftsmanship in this exceptional to be built offering in the highly desirable Chatham Lake neighborhood. Positioned atop a gentle rise, this higher-sitting homesite captures beautiful ridgeline views and stunning sunset views from the front of the home, creating a setting that's difficult to replicate. Buyers have the opportunity to choose between two distinctive home designs, each offered at $1,250,000. The featured plan offers 3,689 sq ft, 5 bedrooms, 3.5 baths, a dedicated first floor office and oversized great room. An open concept main level centers around the spacious great room with fireplace and coffered ceiling, flowing into the custom kitchen and dining area with an oversized island and butler's pantry. Upstairs are four bedrooms plus a large bonus room that may also serve as a fifth bedroom, along with three full baths and second floor laundry. Prefer a first floor primary suite' The alternate 3,528 sq ft Ridgeview design is also availa

Charming, well-maintained ranch in a private cul-de-sac setting with no immediate neighbors, offering easy one-floor living. This home features beautiful hardwood floors throughout, two fireplaces, and remodeled bathrooms. Major updates include a roof that is only six years old, furnace installed around 2019 and newer central air conditioning for added comfort and peace of mind. Additional highlights include a generator hookup in the garage, oil heat, and a walk-out basement providing valuable extra living space, perfect for a family room, home office, gym, or guest area. Enjoy the quiet, private location while still being conveniently close to local amenities. This home combines comfort, privacy, and practical updates, making it truly move-in ready

One floor living in a quiet neighborhood just outside Chester Village. The main floor has a large Living Room, Kitchen and Dining Room, 3 bedrooms, 1 bathroom. The partially finished basement has 2 addional rooms, and storage. Some unfinished projects! Ready for your updating!

Discover move-in-ready living in desirable Chester, one of the Connecticut River Valley's most charming towns! Set on two picturesque acres across from Cockaponset State Forest, this beautifully renovated 4-bedroom, 3.5-bath home blends classic New England character with modern comfort, approximately three miles from Chester Village and Cedar Lake. Inside, refinished hardwood floors, multiple fireplaces, and inviting living spaces create a warm welcome, all updated and freshly painted. The stunning new kitchen features, beautiful cabinets, quartz countertops and premium THOR Gordon Ramsay Collection appliances. A first-floor bedroom and full bath offer flexibility for guests or main-level living. Upstairs, the primary suite boasts a fireplace, 6-foot walk-in closet, a spa-inspired bath with a rain shower and soaking tub! Two more bedrooms and yet another newly remodeled full bathroom complete this level. Approximately 800 square feet of permitted finished lower-level space, complete wi