Killingly Real Estate

Welcome to Killingly, Connecticut—a charming town nestled in the heart of Windham County. With its rich history, picturesque landscapes, and vibrant community, Killingly is a hidden gem that offers the perfect blend of small-town charm and modern conveniences.

Founded in the early 18th century, Killingly boasts a rich tapestry of history that is reflected in its well-preserved architecture and inviting neighborhoods. The town is home to several historical sites, including the Killingly Historical Society, where you can explore the area’s fascinating past. Nature enthusiasts will appreciate the abundant outdoor spaces, with parks like the picturesque Killingly Town Park and the serene Pomfret Reservoir offering opportunities for hiking, fishing, and picnicking.

Killingly is also known for its strong sense of community. Residents take pride in local events, such as the annual Killingly Harvest Festival, which showcases local artisans, delicious food, and family-friendly activities. The town’s schools provide quality education, making it an attractive option for families looking to settle down in a nurturing environment.

For those commuting to nearby cities, Killingly’s location offers convenient access to major highways, making travel to Hartford or Providence a breeze. With a variety of shopping, dining, and recreational options, you’ll find everything you need right at your doorstep.

Whether you’re seeking a peaceful retreat or a place to grow your family, Killingly, CT, is a delightful community that welcomes you with open arms. Discover the charm and warmth of Killingly—your future home awaits!

Newest Listings in Killingly

$699,900

5 Beds ⋅ 4 Baths ⋅ 24189180 MLS

Step back in time while enjoying the comforts of today at this remarkable circa-1770 property, where timeless New England charm meets modern convenience. Set on nearly 4 private acres, this one-of-a-kind estate offers endless possibilities for multi-generational living, rental income, a hobby farm, or the perfect retreat. The beautifully maintained main residence showcases the character and craftsmanship of the 18th century while benefiting from numerous thoughtful renovations and updates throughout. An attached apartment provides excellent flexibility for extended family, guests, or additional income potential. Adding even more value, a separate building on the property offers additional living or occupancy opportunities, making this an exceptional property for those seeking space and versatility. Outside, you'll find an impressive collection of amenities including your own private dock, multiple garage spaces, several outbuildings, and charming sheds that are ideal for entertaining, gatherings, workshops, or creative spaces. The expansive grounds offer room to relax, garden, explore, and enjoy the peaceful surroundings. Whether you're searching for a unique historic home, an investment opportunity, or a private country estate with endless possibilities, this extraordinary property is truly unlike anything else on the market.

1530 Hartford Pike, Killingly

$330,000

2 Beds ⋅ 1 Baths ⋅ 24194578 MLS

Don't miss this adorable, move-in-ready ranch! Offering just over 1,200 square feet of comfortable living space, this charming two-bedroom home features an inviting open floor plan filled with natural light and hardwood floors throughout much of the home. The spacious layout is perfect for everyday living and entertaining alike. Step outside to a generous backyard with a deck, ideal for summer barbecues, relaxing, or enjoying your morning coffee. A newer roof provides added peace of mind, while the attached garage adds everyday convenience. This home is also equipped with solar, providing added energy efficiency and the potential for long-term utility savings. Combining charm, comfort, and a fantastic location close to shopping, dining, parks, and major commuter routes, this home is ready for its next owner to move in and make it their own!

517 Davis Rd, Killingly

$309,000

3 Beds ⋅ 1 Baths ⋅ 24194315 MLS

Adorable Killingly Ranch on a quiet DEADEND street.w/1152 sqft, 3 bedrm, 1 Bath, 1 Car Garage on a HALF ACRE of LAND. Walk in from your front, back or basement door to an open family Rm w/ plenty of sunlight over looking your fully applianced kitchen w/ double sinks, separate dining area with sliders to your deck over looking your BEAUTIFUL back yard. Perfect for BBQ & Parties. Master suite w/ access to the large full bath from BOTH the master & hallway. All 3 bedrms are nice size bedrms with plenty of closet space throughout. Full basement for more expansion, storage or living space. Currently set up as the mechanical room & a finished storage area with a walkout & a 1 car garage w Garage door openers. But could easily be an office, living rm, or an in-law set up. So many possibilities for this cute home. Large PAVED DRIVEWAY. Many updates throughout the years including windows, heating, doors, well pump, curtain drains & MORE. LOW TAXES 3750 A YEAR, Septic, Well & Oil Heating. Sits nicely on .51 ac lot with a private yard in a desireable dead end street. Close to ALL major routes, airports, casinos, rt 6, 395 & RI line.

37 Henry Rd, Killingly

$400,000

4 Beds ⋅ 3 Baths ⋅ 24194082 MLS

This property offers exciting potential for both investors and owner-occupants. With additional buildable land and a river lining the rear of the property, there may be an opportunity to expand, build, or further develop the site, subject to zoning and municipal approvals. The existing layout also offers the flexibility to be converted into a spacious six-bedroom, three-bathroom single-family home with a relatively straightforward renovation. Washer and dryer hookups are already available on both floors, adding convenience and flexibility. Whether held as an income-producing investment, improved for future growth, or transformed into a large residence, this property presents multiple opportunities to add value.

61 Soap St, Killingly

$369,900

3 Beds ⋅ 2 Baths ⋅ 24192500 MLS

Move-In Ready Cape in a Quiet Neighborhood! Nestled on a beautiful 1/4-acre lot in a peaceful neighborhood, this charming 3-bedroom, 2-full-bath Cape offers the perfect combination of comfort, functionality, and flexible living space. Step inside to an inviting open-concept layout where the kitchen, dining area, and living room flow seamlessly together, creating an ideal space for everyday living and entertaining. A sliding glass door leads to the rear deck, overlooking a spacious backyard that's perfect for relaxing, gardening, or hosting gatherings. The main level features a convenient first-floor bedroom and full bathroom, offering flexibility for guests, a home office, or single-level living. Upstairs, you'll find two additional bedrooms and a second full bathroom. The fully walkout lower level adds nearly 700 square feet of additional living space, complete with two finished rooms. One room could easily serve as a potential fourth bedroom, while the other makes an excellent family room, home gym, office, or hobby space. Outside, a tool/storage shed provides added convenience for lawn equipment, seasonal items, and extra storage needs.

67 Katherine Ave, Killingly

$429,900

3 Beds ⋅ 3 Baths ⋅ 24192043 MLS

Welcome home to the heart of Connecticut's beautiful Quiet Corner, where peaceful country living meets modern comfort. Nestled on a quiet street in Killingly, CT, this well maintained 3-bedroom, 2.5-bath home sits on over half an acre of land, offering privacy, space, and a wonderful setting to enjoy all the area has to offer. Step inside to discover a thoughtfully designed floor plan featuring a formal living room, dining room, and a spacious family room just off the kitchen-the perfect gathering place for everyday living and entertaining. The family room offers brand new sliding doors out to the back deck. The house was recently fitted with brand new Anderson windows, new shower walls, 200 amp service, and professionally installed gutter leaf guards. Downstairs, the full basement includes a finished bonus room that offers endless possibilities as a home office, fitness room, craft studio, playroom, or media room. Designed with both convenience and sustainability in mind, this home features an attached two-car garage, energy-saving solar panels, and a Tesla backup battery system, providing increased efficiency and peace of mind during power outages. If you've been searching for a home that combines classic charm, modern updates, exceptional energy efficiency, and a peaceful setting, 40 Taft Street is ready to welcome you home.

40 Taft St, Killingly

$134,900

2 Beds ⋅ 1 Baths ⋅ 24193977 MLS

2 bedroom 2017 mobile home in excellent condition. New LVT flooring throughout, all new appliances, in highly desired R & R Park. Home is tucked in a secluded section of the park on a cul-de-sac. This community is conveniently located in Dayville, near Killingly Commons, and close to everything one might need. Lot rent of $568 includes the site rent, common area maintenance, water, sewer, and trash.

11 R And R Park, Killingly

$299,900

24193379 MLS

Imagine building your dream home on more than 5 scenic acres and creating your own private residential helicopter estate. This unique property is home to Yankee Airstrip (CT13), an officially licensed Connecticut private airstrip, offering the opportunity for a future owner to pursue conversion to a private heliport, allowing you to build a custom home, construct a hangar, and enjoy the convenience of a helipad right in your own backyard. Perched at approximately 720 feet in elevation, the property features breathtaking views, spectacular sunrises, and the peace and privacy of Connecticut's beautiful countryside, while remaining just minutes from shopping, restaurants, three prestigious preparatory schools, and other local amenities. Whether you're a helicopter owner, aviation enthusiast, or someone looking for an extraordinary homesite with endless possibilities, this is a rare opportunity to create a one-of-a-kind residential aviation property. Design your dream home, build your hangar, and enjoy the convenience of flying directly from your own property. Partial owner financing may be considered. Schedule your private tour today and discover the possibilities. If you would rather just purchase and use this property as the existing air strip, please check out MLS listing 24156652 for more pictures and details. Come take a look-let's talk!

1450 North Rd, Killingly

$619,900

24193011 MLS ⋅ Townhouses At Green Hollow Pond BLDG.

The Developmental right and infrastructure for 29 units with possible additional 4 units approved by town. 5 year site plan approval. Plans are recorded and available. Electric, sewer, water is in and available to be hooked up to units. Road is in and paved. Perfect location easy access to RT 6 and I395, Minutes to RI and MA line.

101 Green Hollow Rd, Killingly

$249,900

4 Beds ⋅ 2 Baths ⋅ 24192732 MLS

Opportunity awaits with this two-family home located in a neighborhood setting with convenient access to downtown, shopping, restaurants, and major routes. Whether you're looking to expand your investment portfolio or occupy one unit while generating rental income from the other, this property offers excellent flexibility. Let the rental income help offset your mortgage while building equity. Each unit features separate utilities, providing added convenience for both owners and tenants. The second-floor apartment has its own private exterior entrance for added privacy. Additional highlights include off-street parking, a newer roof, and a layout well-suited for long-term rental or owner-occupied living. Don't miss this versatile multi-family opportunity!

63 School St, Killingly

$850,000

5 Beds ⋅ 3 Baths ⋅ 24176144 MLS

Welcome to your own retreat on more than 5 acres along 5 Mile River. Offering over 5,000 square feet of living space, this custom Colonial combines timeless craftsmanship with modern conveniences. The heart of the home is a chef's kitchen featuring granite countertops, a six-burner Viking gas range with integrated charbroiler, an eat-in dining area, and direct access to the backyard patio. The main level also includes a formal dining room, home office, first-floor laundry, and an impressive living room with soaring cathedral ceilings, hardwood floors, and a custom solid stone gas fireplace. The spacious first-floor primary suite features cathedral ceilings, custom wood-burning fireplace, a walk-in closet, spa-inspired bath with jetted tub, and private patio access. Upstairs is a second full bathroom and four generously sized bedrooms, one of which offers a walk-in closet. The finished space above the three-car garage provides exceptional space for entertaining, recreation, or guests. Conveniences include central air, an oil heating system that can be supplemented by an efficient whole-house wood-burning furnace, generator hookup, hot tub hookup, tanning bed hookup, and numerous smart home features including connected lighting, ceiling fans, Nest thermostat, automatic door locks, video doorbell integrated with the home's phone system, driveway sensor alerts, and bathroom humidity sensors.

56 River Rd, Killingly

$474,900

8 Beds ⋅ 2 Baths ⋅ 24190300 MLS

Side by side two family home, perfect for owner-occupants or investors. Each unit offers a functional layout. One unit features all 4 bedrooms on the second floor with the convenience of a first floor laundry room, while the second unit offers a desirable first-floor bedroom and a similar layout. Recent improvements include new flooring on the second floor bedrooms in unit on the left. Situated on a generous lot, this property presents an excellent opportunity for multi-generational living, rental income, or expanding your investment portfolio.

232 Ballouville Rd, Killingly

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