Killingworth Real Estate

Welcome to Killingworth, Connecticut – a hidden gem nestled in the heart of Middlesex County. This charming town, with its rich history and picturesque landscapes, offers a unique blend of rural tranquility and community spirit. Founded in 1663, Killingworth boasts a quaint, small-town atmosphere that is perfect for families, retirees, and anyone seeking a peaceful retreat from the hustle and bustle of city life.

Killingworth is renowned for its stunning natural beauty, featuring lush forests, serene lakes, and scenic trails that invite outdoor enthusiasts to explore. Whether you enjoy hiking, biking, or simply soaking in the beauty of nature, the town’s expansive parks and conservation areas provide ample opportunities for recreation. The nearby Cockaponset State Forest is a local favorite, offering miles of trails for adventurers of all skill levels.

The community in Killingworth is tight-knit, with a strong emphasis on local events and gatherings. The annual Killingworth Fair is a highlight, showcasing local artisans, delicious food, and family-friendly activities that foster a sense of camaraderie among residents. The town also boasts excellent schools, making it an ideal location for families looking to settle down.

With its convenient location, just a short drive from the vibrant cities of New Haven and Hartford, Killingworth provides the perfect balance of rural charm and urban accessibility. Whether you’re searching for a cozy home, a spacious property, or a serene piece of land to build your dream house, Killingworth offers a diverse array of real estate options to suit your needs. Come discover the warmth and beauty of Killingworth – where community and nature thrive in harmony.

Newest Listings in Killingworth

$699,000

2 Beds ⋅ 2 Baths ⋅ 24217578 MLS

Have you ever wanted to own your own Connecticut farm that dates back to the 1850s? For the very first time in over 170 years, this beautiful property is being offered to the market. Passed down through generations, this remarkable 35+ acre property has been in the same family since the mid-1800s. A true piece of New England history waiting to be brought back to life. Picture yourself stepping into scenes that feel lifted from an old New England painting: the weathered cranberry bog tucked along the edge of the property, the wide-open hay fields swaying in the afternoon sun, and the timeless act of stacking bales in the barn. This is a place where the past lingers in every detail, and the next chapter is ready to be written. With over 700 feet of frontage on Route 81 and the rear acreage backing up to preserved state land, the possibilities here are endless. Imagine restoring this historic farm to its working roots, cultivating crops or raising animals on its fertile ground, or take advantage of its prime location and acreage for a thoughtful development opportunity. Whether you're drawn to its history, its landscape, or its future potential, this property is more than just land, it's a once-in-a-lifetime chance to own a legacy.

511 Rte 81, Killingworth

$225,000

2 Beds ⋅ 2 Baths ⋅ 24216027 MLS

This one has it all, starting with a spacious front porch/entry for seasonal enjoyment. A carport for protection from the elements. a professional ramp that blends seamlessly into the structure. And that is just the outside! Step inside and you can feel the roomy interior, 990 sf. 2 bedrooms one on either side of the unit for ultimate privacy and a bath and 1/2. Half bath is adjacent to second bedroom. Lovely newer appliances and a roomy eat in kitchen. Also a roomy outdoor shed for whatever your needs. The community has a beautiful clubhouse and lots of activities if one wants to attend, or it can be rented out for personal use if available. Also a lovely in ground pool for summer enjoyment. This happens to be a short walk from this home! Come and take a look, you could be in for the upcoming holidays! This is a lovely 55+ community where everyone takes pride in their community.

37 Woodland Trl, Killingworth

$515,000

4 Beds ⋅ 2 Baths ⋅ 24214782 MLS

Pride of ownership shines throughout this beautifully maintained four-bedroom ranch! Generously sized rooms offer comfortable spaces for everyday living and entertaining. A large front bay window fills the living room with natural light, while the separate dining room and spacious eat-in kitchen provide plenty of room to gather. Step outside onto the brand-new deck, built in 2026, and enjoy outdoor dining or relaxing. During their years of ownership, the sellers have made numerous improvements, including updated windows and doors, a replacement septic system and leaching field, and the addition of a generator. A wonderful opportunity to enjoy a thoughtfully improved home with room to make it your own!

201 Emanuel Church Rd, Killingworth

$834,900

4 Beds ⋅ 3 Baths ⋅ 24213783 MLS

Welcome to 26 Overlook Farms Road, a beautifully maintained Colonial set on 2.2 private acres in one of Killingworth's most sought-after neighborhoods. With over 3,000 square feet of thoughtfully designed living space, this home offers 4 spacious bedrooms, 2.5 bathrooms, and a 3-car attached garage. The bright, open floor plan is perfect for both everyday living and entertaining, featuring inviting living areas, a cozy family room with a fireplace, and a well-appointed kitchen. The walk-out basement provides endless possibilities for future expansion-create a home gym, recreation room, media room, or additional living space to suit your needs. Step outside to your own private retreat with mature trees, beautiful landscaping, and plenty of room to relax, entertain, or enjoy the outdoors. A storage shed offers added convenience for lawn equipment, tools, and outdoor essentials. Ideally located just minutes from the shoreline, shopping, restaurants, and major commuter routes, this home combines the tranquility of country living with easy access to everyday conveniences. Don't miss this exceptional opportunity to own a beautiful home in one of Killingworth's premier neighborhoods. Schedule your private showing today

26 Overlook Farms Rd, Killingworth

$500,000

3 Beds ⋅ 3 Baths ⋅ 24208096 MLS

A charming and comfortable ranch set along Chestnut Hill, one of Killingworth's most picturesque roads. This inviting home offers a wonderful blend of warmth, privacy, and natural beauty. The open living and dining area features a handsome stone fireplace and hearth, while a wall of glass fills the space with natural light. French doors lead to a sunroom that extends the living area and captures views of the surrounding property. A gas fireplace adds year-round comfort and ambiance. The kitchen features granite countertops and a breakfast bar. Three bedrooms and two baths are located on the main level. Handsome hardwood floors throughout. A spacious 36' x 12' deck provides ample room for grilling, relaxing, and entertaining. Enjoy a sense of peace and privacy while taking in views of the yard and surrounding woods. The expansive lower level offers excellent flexibility, with space for a rec room, studio, home office, or family room. A half bath and convenient access to the attached two-car garage add to its versatility. Set on 3.8 acres, the property offers plenty of room to enjoy the outdoors. A generous fenced-in area is ideal for play, gardening, and pets. Located in southern Killingworth, the home offers convenient access to the shoreline, downtown Madison, shopping, and restaurants. Boston and New York are within a few hours' drive, and commuting routes are easily accessible.

173 Chestnut Hill Rd, Killingworth

$98,500

1 Beds ⋅ 1 Baths ⋅ 24213078 MLS

You will be impressed by the open concept in this home! The interior walls were removed to create a wide open feel with the kitchen, eat-in area and living room blended together into one continuous space! Even the bedroom has a spacious feel. There is a stackable washer and dryer hidden in the hall closet, full bath with walk-in shower and numerous built-ins and closets throughout. Beechwood is a lovely over 55 mobile home community in the wonderful, rural town of Killingworth. This home is sited on a level and sizable lot very close to the community clubhouse and inground pool. The home was pre-inspected and the seller had recommended repairs done by professional contractors. The inspection report and repair receipts are available for your review upon request.

16 Country Club Trl, Killingworth

$75,000

24212586 MLS

Business opportunity for hair stylist professionals. Long established salon on Route 81. Four stations and private massage and facial room. Beautifully appointed custom built furnishings throughout with central vac for convenience.

176 Rte 81 Unit 2A, Killingworth

$500,000

3 Beds ⋅ 3 Baths ⋅ 24211529 MLS

Incredible value! This turnkey home offers single-level living without compromise! Step into a sun-drenched, versatile open floorplan with hardwood floors, a harmonious palette, and updates throughout. The chef's kitchen anchors the main level with sleek cabinetry, granite countertops, stainless steel appliances, and chic accents and flows seamlessly into a spacious dining area. Framed by oversized windows & a handsome wood burning fireplace the living room is the perfect spot to gather & unwind. From here, you can step directly out to an oversized deck overlooking your glorious outdoor haven. The peaceful wooded views & enchanting koi pond are the ideal backdrop for grilling & al fresco dining. Back inside, the primary suite offers custom storage and a refreshed ensuite. Two additional bedrooms and a full bath round out the main level. Downstairs, the incredible finished flex space adds a superb layer of flexibility with room for a media room, home gym, or creative studio, plus a separate guest suite complete with its own full bath. The boxes are checked with central air, a 2 car attached garage, & lovely mature landscaping. Located moments from shoreline beaches, local trails, and everyday essentials, this home offers classic New England charm and small-town living at its best. 15 min to downtown Chester & Essex Village! Move-in ready, deeply peaceful, and built for easy living. The total package awaits!

240 Rte 148, Killingworth

$599,900

3 Beds ⋅ 2 Baths ⋅ 24211881 MLS

Set on 2.2 acres in Killingworth's historic farm country, this Classic Colonialoffers 2,480 sf across two stories - 8 rooms, 3 bedrooms, and 2 fullbaths. Hardwood floors run through the dining room, living area, and bedrooms,white raised-panel wainscoting adorns the dining room, family room is complete with a gas fireplace French doors. The gourmetkitchen features a huge center island, ideal for entertaining.An attached 576-square-foot two-car garage (2005) and a full 1,040-square-footwalkout basement provide generous storage, workspace and endless potential for expansion. Ductless cooling is highly efficient. The oversized primary bedroom is complete with walk in closet and additional changing room which could easily be turned into a full bath. Outdoor living extends the square footage: a 222-square-foot wood deck (2016)and a 520-square-foot paver patio (2020), plus a 200-square-foot shed (2011). A22kW Generac whole-house generator keeps the house running when everyone else is in the dark. Recent updates include a new front door (2025), 5-replacement windows (2022), and a main-house roof that is approx. 6 years old. Enjoy nearby Chatfield Hollow State Park, Cockaponset State Forest,Parmelee Farm, and Killingworth Recreational Park - plus resident beach access at Clinton Town Beach(small fee). SELLER OFFERING $7500 CLOSING COST CREDIT FOR ACCEPTABLE CONTRACT(must be written in contract).

433 Rte 148, Killingworth

$749,900

3 Beds ⋅ 3 Baths ⋅ 24207798 MLS

Tucked away on 4.5 beautiful acres in Killingworth, 79 Chestnut Hill Road offers exceptional privacy, peaceful pond views, and a welcoming sense of home from the moment you arrive. This distinctive 3-bedroom, 3-bath antique residence is filled with warmth and character, thoughtfully updated to provide the comfort and convenience of modern living. Extensive improvements completed between 2008 and 2026 include fresh interior paint, beautifully refinished natural hardwood floors, and a new elevated bluestone patio. Additional updates include the roof, windows, exterior paint, gutters, and water heater, along with updated electrical and plumbing, three-zone heating, central air, and a whole-house automatic generator. The kitchen and bathrooms have also been tastefully updated while preserving the home's timeless charm. Outside, mature trees, protected rear privacy, and an expansive, usable lawn create a serene backdrop with plenty of room to garden, entertain, explore, or simply enjoy the changing seasons. Whether spending a quiet morning at home, an afternoon outdoors, or an evening gathered with family and friends, this property offers a lifestyle that feels comfortable, private, and timeless. Offering generous land, historic character, substantial modern infrastructure, and convenient access to the shoreline and surrounding towns, 79 Chestnut Hill Road is a truly special property best experienced in person.

79 Chestnut Hill Rd, Killingworth

$245,000

24202311 MLS

Discover an exceptional opportunity to build your dream home on this beautiful 2.66-acre parcel, perfectly positioned to offer both privacy and convenience. Set well back from the road, the property provides a peaceful, secluded setting while remaining just minutes from area amenities and attractions. Much of the important preliminary work has already been completed, making this an outstanding opportunity for those looking to design and build a custom residence. Site preparation includes complete engineering and stamped site plans, professional land surveying with monuments installed, Town of Killingworth wetlands approval for a pre-installed culvert and established road access, Connecticut State septic system approval for a proposed home, and a CT DOT-approved driveway entrance directly from the state road. The lot has been thoughtfully cleared while preserving a generous natural buffer around its perimeter, creating an ideal combination of usable open space and privacy. Enjoy a tranquil setting surrounded by nature and wildlife with plenty of room for outdoor living, entertaining, gardening, or simply relaxing. Convenient access to the Connecticut shoreline, beautiful beaches, premier shopping outlets, and Middletown further enhances this desirable location. A rare opportunity to create your own private retreat in a beautiful natural setting with extensive planning and approvals already in place.

262 Rte 81, Killingworth

$575,000

5 Beds ⋅ 2 Baths ⋅ 24204501 MLS

Spacious 5-Bedroom Colonial on 3.6 Private Acres in Killingworth. Looking for space, privacy, and a home with major updates already completed? Welcome to 100 N Tower Hill Road in Killingworth! Set on 3.6 private acres, this spacious Colonial offers 5 bedrooms, 2 full bathrooms, and approximately 2,090 square feet of living space. Recent improvements include a new septic system, new boiler, new windows, new carpeting throughout, and fresh interior paint. The property also features an attached 2-car garage, a walk-up attic offering additional storage potential, and a private, level setting with room to enjoy the outdoors. With generous interior space, a peaceful setting, and several major improvements already completed, this property offers an opportunity to make a home your own in desirable Killingworth. Property is offered as is. Photo Disclosure: Some photos have been virtually staged using AI-generated furnishings for illustrative purposes. Furniture and decor shown in these images are not included with the property. Actual room appearance may vary.

100 N Tower Hill Rd, Killingworth

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Killingworth Real Estate

Newest Listings in Killingworth

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