Windham County, CT Real Estate | Windham County, CT Homes for Sale

Small cul-de-sac with 3 colonials built. 2.5 acres with underground utilites. 4 bed septic design. Peaceful country setting but close to everything. 5 minutes from RI state line in coventry and 7 minutes to ct 395. 30 minutes north to worcester ma and 40 minutes south to ct coastline. A build package is available with lot included in the 699k range. The seller is a real estate licensee

8 Partridge Pl, Sterling

$599,900

3 Beds ⋅ 2 Baths ⋅ 24208918 MLS

LAKE LIFE AWAITS!! This stunning like-new home has been fully renovated to include 2 full beds and baths, with a 3rd loft style flex room which can be used for a bedroom or added living space. This home features soaring ceilings, incredible waterfront views and an open concept kitchen with OVERSIZED island. The thoughtfully designed lake house could be the ideal getaway, or used for investment. You will LOVE the sunsets and cozy nights on the large trex deck looking over the tranquil lake. Within minutes from the highway making this an ideal destination or full time lifestyle! The house was fully restored from a shell and has high energy efficiency, electric heat and mini split systems for clean air flow, and low maintenance. Set on a private road with charming New England views at all seasons, you wont want to miss this one!!

7 Amidon Dr, Ashford

$2,500,000

24212430 MLS

Rare opportunity to acquire a profitable and permitted tan stone and quartz quarry consisting of two adjoining lots being sold as one. The offering includes a 58.76-acre active quarry and an adjoining cleared 8.8-acre lot, totaling approximately 67.56 acres. The quarry has produced a variety of desirable natural stone products, including slabs, thin wall stone, wall stone, and other tan stone and quartz materials. These materials have a wide range of uses, including landscaping, retaining and decorative walls, patios, walkways, steps, hardscaping, building applications, and construction projects. Also included in the sale are 4,000+ tons of cut granite in a variety of sizes, providing a substantial existing inventory of marketable material. With established permits, proven stone production, valuable natural resources, significant granite inventory, and additional cleared acreage, this is an exceptional opportunity for an investor, contractor, stone supplier, or quarry operator looking to expand.

94 & 100 Hubbard Hill Rd, Killingly

$578,520

24212010 MLS

New Roof (2011), Natural Gas Heat (Converted 2012), New Chimney Liner (2012). City Water, Sewer & Gas. Town owned. They will rezone for you depending on your use.

47 Crescent St, Windham

$769,000

3 Beds ⋅ 3 Baths ⋅ 73586961 MLS

A truly extraordinary property, 332 Ravenelle Road offers space, quality, privacy and versatility that are nearly impossible to find! Set on 13.5 gorgeous acres, this expansive ranch was built and occupied by its contractor/builder with exceptional attention to quality throughout. Designed for easy one-floor living, the home features 9-foot ceilings and a spectacular open floor plan anchored by a chef's kitchen and enormous family room-perfect for everyday living and entertaining. The massive 3-car garage boasts impressive 13-foot ceilings, while the 9-foot-ceiling basement runs virtually the full footprint of the home and previously housed the builder's extensive workshop-ideal for a contractor, car enthusiast, hobbyist or home-based business. Outside is your own private retreat with an above-ground pool, fenced area for animals, shed, abundant wildlife and beautiful seasonal views. Approximately 100 acres of landlocked private property and hundreds of acres of conservation land beyond create remarkable surrounding privacy and make this setting especially appealing to hunters and outdoor enthusiasts. Just across the street, West Thompson Lake offers fishing, boating and a public boat launch. A rare combination of exceptional craftsmanship, one-floor living, serious workspace and an incredible country lifestyle!

332 Ravenelle Road, Thompson

$499,900

6 Beds ⋅ 3 Baths ⋅ 24212211 MLS

Beautifully charming and beaming with character is this very spacious 2-family duplex; a rare find in Woodstock! This home is not your typical duplex and has a great floor plan in each unit. Perfect for an owner that wants to occupy a lovely home in a great location. Also nice for investors because the nicely updated and generously-sized units, each with their own laundry on the main floors, brings a higher rental income! The very large main house has attractive character, 4 large bedrooms, 2 full bathrooms, a dreamy updated kitchen with open floor plan to living room and dining areas. A first floor 4th bedroom and a laundry room on the main floor is large enough to be a 5th bedroom or office space! The second floor has three large bedrooms and a very large open den/craft room/office/home or college school area and a 2nd full bath! This unit has more space than you can dream to fill! The second unit is also generously-sized and nicely updated with 2 large bedrooms and a laundry room large enough to be a 3rd bedroom or office. Large living room leads to the updated open kitchen with an island and separate dining room. The home has a 3-car detached garage and peacefully landscaped grounds with room to garden. All separate utilities. Well water and public sewer. Listing Agent related to Seller. Come see this hidden gem before its gone!

9 Ellen Ln, Woodstock

$200,000

24212217 MLS

Opportunity awaits with this 16.76-acre parcel in Canterbury's Rural District! With frontage along both Water Street (approx. 300') and Kinne Road (approx 350'), this undeveloped property offers exciting possibilities for a variety of buyers. Explore the potential for subdivision and development, or create a private homesite surrounded by acres of your own land. The property's size, configuration and access from two roads may offer flexibility when considering future development plans. RD zoning allows residential and agricultural uses by right, among other potential uses subject to applicable approvals. Whether you're a builder/developer looking for your next project, an investor adding land to your portfolio, or a buyer dreaming of a secluded country property with room to spread out, this parcel is worth exploring. Conveniently located in Canterbury while offering the space and privacy that make rural living so appealing. Buyer to perform due diligence regarding subdivision potential, wetlands, soils, septic, utilities, road frontage and intended use.

21/10/A Water St, Canterbury

$409,900

3 Beds ⋅ 2 Baths ⋅ 24211842 MLS

Classic New England Charm Meets Flexible Modern Living! Welcome home to Killingly, Connecticut, where you will find this picture-perfect 3-bedroom Cape Cod-style home tucked away at the very end of a peaceful, private cul-de-sac. Offering the ideal blend of classic architectural character and highly sought-after functional spaces, this property is ready for its next chapter. Gather or unwind in a bright, airy living room highlighted by an impressive vaulted ceiling that elevates the entire main living floor. A spacious kitchen features sliding glass doors that open directly onto a spacious back deck-perfect for indoor-outdoor dining, morning coffee, and summer BBQs. The ultimate flexible space! Positioned over the attached 2-car garage, this bonus room is perfect for a private home office, an epic media room, a fitness studio, or a secluded guest suite. Whether you love the idea of crisp New England autumns hosting on your private deck or want a dedicated workspace that feels entirely separate from your main living areas, this Killingly gem checks every single box.

16 Jefferson Dr, Killingly

$379,900

3 Beds ⋅ 2 Baths ⋅ 73586518 MLS

If you're looking for a place to be surrounded in all that nature has to offer, you'll want to call this home! This 3 bedroom, 2 bath, saltbox colonial is sited on a double lot, bordering Wyndham Land Trust. You'll love watching the deer and other wildlife from the 10'x20' deck. As a part of the private community of Lake Bunggee, you may also take a short stroll to the beaches to enjoy water rights and access. The lake is about 112 acres to enjoy boating, fishing, swimming and hiking areas. The light filled, open floor plan is perfect for entertaining; vaulted ceiling living room/dining area has hardwood flooring, an expansive wall of windows, and slider open to deck. Tiled kitchen has cozy breakfast bar and spacious walk-in pantry. 1st floor bedroom has ensuite bath with shower. 2nd floor primary also has ensuite bath with tub/shower unit and walk-in closet. Additional bedroom on second floor. Walk-out lower level has wood stove. Updates include newer hot water tank, septic system, and oil tank. Roof shingles 2015. Welcome Home!

35 Old Sawmill Rd, Woodstock

$379,900

3 Beds ⋅ 2 Baths ⋅ 24211726 MLS

If you're looking for a place to be surrounded in all that nature has to offer, you'll want to call this home! This 3 bedroom, 2 bath, saltbox colonial is sited on a double lot, bordering Wyndham Land Trust. You'll love watching the deer and other wildlife from the 10'x20' deck. As a part of the private community of Lake Bunggee, you may also take a short stroll to the beaches to enjoy water rights and access. The lake is about 112 acres to enjoy boating, fishing, swimming and hiking areas. The light filled, open floor plan is perfect for entertaining; vaulted ceiling living room/dining area has hardwood flooring, an expansive wall of windows, and slider open to deck. Tiled kitchen has cozy breakfast bar and spacious walk-in pantry. 1st floor bedroom has ensuite bath with shower. 2nd floor primary also has ensuite bath with tub/shower unit and walk-in closet. Additional bedroom on second floor. Walk-out lower level has wood stove. Updates include newer hot water tank, septic system, and oil tank. Roof shingles 2015. Welcome Home!

35 Old Sawmill Rd, Woodstock

$799,000

5 Beds ⋅ 4 Baths ⋅ 24211775 MLS

Set on 19 picturesque acres in Thompson, this unique property offers tremendous flexibility for residential and equestrian use. Formerly used as a two-family home it provides options for single family, multi-generational living, farm staff, owner occupancy, or rental income. The home has been professionally cleaned, with major improvements already completed including a new roof, windows, garage doors, repointed chimney, serviced furnace, new dishwasher in the upper unit, refinished upstairs floors, repainted porch, and rebuilt deck. Kitchens and bathrooms offer an opportunity for additional cosmetic updating and personalization. Equestrian amenities are extensive, including a 12-stall main barn with multiple tack, feed and storage areas, lounge, bathrooms, water, and an approximately 2,000-bale hay loft. The lower barn offers 7 additional stalls with room to expand, plus storage. Two accessory buildings include a garage-style structure ideal for equipment storage. A 50' x 100' indoor arena provides year-round riding, while five fenced grass pastures with automatic waterers offer excellent turnout. With substantial infrastructure, multiple buildings, established fencing, and 19 acres - this property is ready for its next chapter. A rare opportunity for an equestrian estate, boarding or training operation, or simply the space to create your ideal multi-generational property.

91 Church St, Thompson

$329,000

4 Beds ⋅ 2 Baths ⋅ 24211232 MLS

Perfect for a first-time homebuyer looking to offset housing costs with rental income. Live in one unit while the tenant helps pay the mortgage. This two-family home offers 2 bedrooms, 1 full bath, a kitchen, living room, and an enclosed front porch. Several recent updates include a NEW ROOF, a NEW GAS HOT WATER HEATER, NEW CARPETING, and a REGLAZED TUB and SINK. Each unit features plenty of off-street parking and a one-car garage. Each unit has its own utilities, NATURAL GAS for heat. The full basement includes washer and dryer hookups and offers plenty of storage space. An enclosed rear porch at ground level leads to a private backyard. Conveniently located, close to downtown, shopping, restaurants, and local amenities, this property combines affordability, comfort, and income-producing potential. A great opportunity for first-time buyers, owner-occupants, or investors looking to build equity while generating rental income.

25 Gilman St, Putnam

$375,000

3 Beds ⋅ 1 Baths ⋅ 24211687 MLS

Welcome to 62 Bates Pond Road in Canterbury-a three-bedroom, one-bath home on just over two acres, offering privacy and a peaceful country setting. The newly finished basement provides flexible space for relaxing, entertaining, a home office, or hobbies. Canterbury offers town-funded high school options, including Woodstock Academy and other area schools, with tuition supported through local taxes. The home will be sold with a full oil tank and a brand-new generator included with the purchase

62 Bates Pond Rd, Canterbury

$550,000

4 Beds ⋅ 2 Baths ⋅ 24211512 MLS

*MOTIVATED sellers, bring offers* Welcome to this spacious 4 Bedroom Cape, offering a versatile floor plan with plenty of room to spread out, this home blends classic character with thoughtful updates. The main level features beautiful hardwood floors and an inviting eat-in kitchen with a center island and cooktop, wall oven, and plenty of space for everyday meals. A separate dining room, comfortable living room, & additional sitting room provide multiple gathering spaces, with the sitting room offering flexibility as a home office, den, or reading room. Two beautifully remodeled full bathrooms add modern style and convenience, one with radiant heat floors. Upstairs, you'll find four generously sized bedrooms plus a charming hallway nook that offers additional flexible space for a desk, study area, fitness equipment, or hobbies. Loads of closets everywhere! Brand new roof & Skylights offer additional value. Set on 1.7 acres with room to enjoy the outdoors, this property is conveniently located near a golf course, parks, bike trails, and area private schools. A wonderful opportunity to enjoy space, versatility, and the beauty of Pomfret living!

248 Paine Rd, Pomfret

$209,900

5 Beds ⋅ 1 Baths ⋅ 24211639 MLS

The potential is endless in this classic 1890 conventional style home which sits on a spacious .69 acre open level corner lot, offering strong curb appeal and plenty of outdoor usability. The property features 5 bedrooms, providing excellent space for larger households or flexible room arrangements. With its old-world charm and traditional layout, the home presents a solid foundation for buyers looking to update and personalize to their own taste. The structure, lot size, and location create meaningful long term value, and buyers will appreciate the opportunity to restore this well situated Plainfield property into a comfortable and character filled residence. Hurry to book a viewing, simply too good to be true. Don't miss this diamond in the rough.

31 Depot Rd, Plainfield

$410,000

3 Beds ⋅ 2 Baths ⋅ 24211572 MLS

Tucked away at the end of a quiet Killingly cul-de-sac, this 3-bedroom, 2-full-bath ranch offers comfortable one-level living, privacy and a long list of updates. Set on 0.88 acres and surrounded by a natural buffer, this 1,144 sq. ft. home was extensively renovated in 2022, including a new roof, siding, electrical, plumbing, propane heating system, insulation, sheetrock and flooring. Step inside to a bright, neutral interior and an updated kitchen with appliances installed as part of the 2022 renovation. The convenient one-level floor plan offers three bedrooms and two full baths, making excellent use of the home's space. The full basement provides additional storage and a one-car garage with plenty of room for tools, equipment and projects. Outside, the spacious lot offers wonderful potential to create your own backyard retreat; add a patio or firepit area, expand the gardens, create space for outdoor entertaining or simply enjoy the privacy. The open cul-de-sac setting provides additional breathing room and space for outdoor play with minimal through traffic. With the major renovations already completed, efficient propane heat and a peaceful setting, this is an opportunity to move in and enjoy while making the outdoor space your own.

549 Squaw Rock Rd Extension, Killingly

$399,000

3 Beds ⋅ 2 Baths ⋅ 24211443 MLS

Numerous improvements have been completed since 2024 at this 3-bedroom, 1.5-bath ranch set on 5.14 acres in Ashford. Updates include a new septic system with basement plumbing, new oil tank, new attic insulation, furnace service, chimney repointing and new chimney cap, tree removal, and professional survey. Inside, the home offers refinished hardwood floors, a bay window, and a beautiful fieldstone fireplace in the living room. The eat-in kitchen features knotty pine cabinetry and a cozy breakfast nook. An enclosed breezeway connects the main house to the one-car garage, providing convenient access and additional storage. Each bedroom offers built-in storage, while the walk-out lower level provides excellent potential for a family room, home office, workshop, or additional living space. The home is also generator-ready with a transfer switch. The property offers privacy, outdoor space, and room to enjoy the peaceful Ashford setting while remaining conveniently located to area amenities and UConn.

108 Krapf Rd, Ashford

$330,000

3 Beds ⋅ 1 Baths ⋅ 24211453 MLS

The ranch you've been waiting for! Freshly remodeled, bright, clean & full of charm, this 3-bedroom home is ready to steal your heart. New flooring flows throughout, complemented by modern lighting and a beautifully refreshed full bath. The updated kitchen features stainless steel appliances, a center island, and plenty of room for a dining table-because the best memories happen gathered around good food! Outside might be even better: a fenced-in backyard, custom patio, and outdoor fireplace ready for crisp fall nights, cozy fires & s'mores. Add in a newer roof and a neighborhood setting right next to a ball field and park, and this little ranch packs a whole lot to love. Cute, cozy & completely move-in ready! One level living at its best!

21 Potvin Ave, Plainfield

$330,000

3 Beds ⋅ 2 Baths ⋅ 24210972 MLS

There's something especially inviting about a home with room to settle in, spread out, and make it your own. Set on .89 acres, this charming 1941 property offers three bedrooms, two full bathrooms, and hardwood floors throughout much of the interior. Decorative wood cornices above the living and dining room windows add a touch of character, while the enclosed front porch creates a cheerful entrance. A sliding door in the kitchen provides access to the spacious, tiered deck overlooking the backyard, an easy spot for summer dinners, weekend barbecues, or simply enjoying the view. Laundry is conveniently situated in the second-floor bathroom. Outside, there is plenty of space to garden, play, entertain, or gather around a firepit. A detached one-car garage and newer Klotter Farms shed provide additional storage. Just minutes from downtown Putnam, this sweet and comfortable property offers wonderful outdoor space and room to grow.

178 Farrows St, Putnam

$449,900

7 Beds ⋅ 4 Baths ⋅ 24210750 MLS

Great two family opportunity in downtown Putnam featuring a rare to find, 4 bay garage & commercial/industrial shop space with separate electric & sewer connections. The existing large duplex, believed to be two single families that have been long ago connected, features architectural singled roof, vinyl siding, replacement windows, updated boilers, electrical & oil tanks. Two stable tenants in both units which are very large with many potential bedrooms setups and both units featuring multiple bathrooms. The large covered front porch is a great feature. The shop/garage has tons of potential. Shop has two floors (main & cold storage basement). Great for contractors! This investment is more like a 3 unit investment or a commercial owner occupant with residential income.

291-293 School St, Putnam

$790,000

4 Beds ⋅ 2 Baths ⋅ 24209026 MLS

Set high above the road at approximately 900 feet in elevation, this beautifully maintained home combines privacy, natural light and a versatile floor plan in a picturesque setting. Southwestern exposure fills the home with sunlight, while the two-story entry and catwalk overlooking the dramatic living room create an impressive sense of space. The living room features a woodstove and direct access to the covered back deck, creating an inviting connection to the outdoors. A charming three-season sunroom at the front of the home provides another bright and comfortable space to enjoy the surrounding setting. The main level offers convenient one-floor living with two bedrooms, a full bath and a laundry room with both exterior and garage access. There is no carpet in the home-hardwood and tile run throughout. Upstairs, the private primary bedroom suite is joined by an additional bedroom and a flexible office/library/den. An unfinished walk-out basement provides excellent storage and plenty of potential for future finished space or possible in-law accommodations. Well insulated with 12-inch foundation walls, a dry basement, good drainage and excellent well water. Enjoy the privacy of the property while being just down the road from the approximately 8,000-acre Yale-Myers Forest with miles of trails and outdoor recreation. Conveniently located only 1 mile to I-84, with easy access to Hartford and approximately one hour to Boston and two hours to New York City.

183 Hillside Rd, Ashford

$85,000

24210559 MLS

What could you build on Lot 4 at Aplin Hill? We've already started imagining the possibilities. This .88-acre homesite is tucked within a thoughtfully planned Woodstock subdivision, with conservation land along the northern and eastern boundaries providing a natural buffer. A local builder has developed a proposed home design with this lot in mind, giving buyers a great starting point for seeing what could take shape here. The rendering and floor plan are conceptual and can be modified, or buyers are welcome to bring their own plans and builder. For buyers who prefer a more streamlined path to building, the proposed builder package takes much of the guesswork out of the process. The builder's estimated price includes construction of the home, site work, septic, well and driveway. Current builder pricing, specifications and details of what is included are available upon request. Aplin Hill features just 10 homesites across 29 acres, with approximately 18 acres preserved as permanent open space. Infrastructure includes a town road, walking path, underground power at the street and hydrant. Architectural guidelines help maintain the character of the neighborhood, where newer homes have recently been completed on neighboring lots.

Aplin Hill Ln, Woodstock

$499,900

3 Beds ⋅ 3 Baths ⋅ 24210893 MLS

Beautiful new country home to be built on a picturesque 1.03-acre lot, offering the perfect blend of quality, comfort, and modern design. The thoughtfully designed open floor plan features solid wood flooring, vaulted ceilings in the living and dining rooms, and an abundance of natural light. The custom kitchen will showcase granite countertops and plenty of space for cooking and entertaining. Enjoy the convenience of 2 full baths plus a half bath, central air conditioning, and an attached 2-car garage. This is your opportunity to personalize and customize a brand-new home to fit your style and needs. Build the home you've been dreaming of in a peaceful country setting!

7 Scarborough Rd, Windham

$169,900

5 Beds ⋅ 2 Baths ⋅ 24210829 MLS

Do not miss out on the opportunity to own this Mansard style Victorian in Putnam for ONLY $169,900! Currently zoned as a single family but has the possibility of changing use back to a duplex for income producing opportunities. 3 Stories featuring 2,767 square feet consisting of 5 bedrooms and 2 full baths with room to expand the square footage even more. This property is in need of extensive renovation, but offers tremendous potential for the right buyer. With vision, effort, and the right improvements, there is a great opportunity to build significant sweat equity and transform the property into something truly special. More photos coming soon. Call today for private tour!

20 Bradley St, Putnam

$102,000

24210652 MLS

The property was recently subdivided from a larger 6-acre parcel, has been perc tested, and has a 3-bedroom septic plan available. Lightly wooded, 4.125-acre residential building lot with about 330 feet of paved-road frontage. The terrain rises gently into the wooded area.

Lot 169A Kapitulik, Thompson

$288,000

3 Beds ⋅ 1 Baths ⋅ 24210578 MLS

Welcome to this well-cared-for home, where thoughtful updates and a comfortable layout create an inviting place to call home. The spacious eat-in kitchen provides plenty of room for meals and entertaining and flows naturally into the living area. The home offers three bedrooms and a well-maintained bathroom. A full walkout basement provides excellent potential space, whether you need a recreation room, home office or workshop. Outside, you'll find a private deck, paved driveway, an a carport for convenient parking and outdoor enjoyment. The roof was newly installed in September 2026, providing an important recent improvement for the next owner. With its comfortable floor plan, outdoor amenities, and opportunity to expand, this home offers plenty of room to make it your own. Situated in a peaceful and desirable part of town, the property is also conveniently located near UConn and Eastern Connecticut State University.

154 Manners Ave, Windham

$625,000

4 Beds ⋅ 3 Baths ⋅ 24210501 MLS

The Benjamin Bosworth House has been part of Eastford's landscape for more than two centuries, and there is still nothing quite like it. Set on 3 acres, this Federal-style home, completed around 1800, offers 4,538 square feet, 4 bedrooms, 2.5 baths and 11 fireplaces. Its defining feature is a rare full-height monitor, once used as a Masonic meeting hall, with built-in benches and fireplaces. Throughout the house, hand-carved woodwork, historic finishes and generously scaled rooms tell the story of its past. The main level includes a formal dining room, parlor, sunlit sitting room, kitchen, studio and workshop, with additional flexible space upstairs. Since purchasing the home in May, the current owner has continued restoration work, including new lime plaster in the parlor and second-floor hall, a retiled upstairs bath and fresh paint in several rooms. Listed on the National Register of Historic Places, this is a remarkable opportunity for someone who appreciates early American craftsmanship and wants to carry its story forward.

89 John Perry Rd, Eastford

$399,900

3 Beds ⋅ 2 Baths ⋅ 24210420 MLS

Welcome to Sterling Hills Estates, where luxury meets convenience! This Brand New 2026 to be built Raised Ranch offers the epitome of modern living, with time to choose appliances, countertops and interior paint color. With Central Air and Hardwood flooring throughout, this home boasts City water and Sewer for added comfort. Picture yourself in the Gorgeous Granite Kitchen, complete with a view of the valley while you do dishes! Enjoy the ease of a maintenance-free lifestyle, including lawn, road maintenance, and snow removal for just $140 a month. This one-of-a-kind home sits at the end of a cul-de-sac amidst fine homes, offering privacy & prestige. With a lower level ready for your personal touch, plus a 2-car garage & a paved driveway, convenience is key. Located right on the RI & CT Line, commuting is a breeze. Experience Quality Craftsmanship & Construction with high-end finishes, including gourmet granite kitchen, crown molding, and sleek vinyl siding. This private community on the Rhode Island & Connecticut Line offers proximity to major routes & highways, making this the perfect opportunity to own your dream home in Sterling Hills Estates.

35 Sterling Ridge Ln Unit 29, Sterling

$69,000

24210414 MLS

Unlock the potential of this residential property located at 11 Otis Street in Killingly. Offering a unique opportunity for investors, builders, or anyone looking to create something new, this property is being sold as part of a bundled package with 411 Hartford Pike, Killingly, CT. Whether you're exploring development possibilities, expanding your portfolio, or securing land in a convenient location, this offering provides flexibility and long-term value. Situated close to local amenities, schools, shopping, and major routes, the property benefits from both accessibility and a well-established community setting. Both properties are to be sold together. Please perform all diligence regarding zoning, permitted uses, utilities, and any potential development opportunities. Property is being sold as-is.

11 Otis St, Killingly

$349,999

9 Beds ⋅ 4 Baths ⋅ 24210190 MLS

HISTORIC CHARM MEETS VALUE ADD POTENTIAL in Connecticut's Quiet Corner! This distinctive multi family property offers 3 residential units plus a fourth space with commercial potential, and a fascinating history as Kenney's Store, a post office and train depot. Units 1, 2 and 3 feature spacious layouts, beautiful hardwood floors and timeless character. Two units offer 3 bedrooms, while the third offers 2 bedrooms. Unit 1 is currently configured as a 1-bedroom but can be converted back to a 2 or 3 bedroom layout. The property is ready to be repositioned, with one or two residential units requiring significant renovation and the former commercial space offering a true blank canvas for its next use. The commercial space includes two large rooms and a half bath. For the investor, owner occupant or entrepreneur with vision, this is an opportunity to transform a historic property and unlock its potential. Conveniently located near Acme Pond, the Air Line North State Park Trail, local vineyards and breweries, antique shops and scenic country roads. Bring your vision and create the next chapter of this unique property! CASH BUYER ONLY

6 Old Rte 12, Thompson

$389,900

4 Beds ⋅ 2 Baths ⋅ 24209361 MLS

OVERSIZED Cape w/ NEW FLOORING throughout main level on the end of a cul-de-sac w/ CITY WATER & SEWER! 4 BEDROOMS- 2 LARGE bedrooms upstairs (one has a WALK IN CLOSET) REMODELED bathroom w/ TILE flooring, updated vanity and tub w/ TILE back splash. 2 additional bedrooms on first floor, UPDATED bathroom w/ NEWER toilet and VANITY. SPACIOUS living room, eat in kitchen w/ LARGE ISLAND NEW BOSCH dishwasher, stove & microwave conveying. SLIDER leads to 10 x 12 DECK overlooking .70 of an acre. GENERATOR 8000 WATT will CONVEY for peace of mind during storms. SOME furniture WILL BE CONVEYING. PAVED driveway w/ plenty of parking and ! CLOSE to 395 for easy commute. 28 x40 BASEMENT for ALL your storage. CAN CLOSE ANYTIME! Camera & Audio inside and out.

66 High Meadow Dr, Plainfield

$349,900

5 Beds ⋅ 2 Baths ⋅ 24210038 MLS

Spacious two-family home offering 5 bedrooms, 2 baths, a large basement, detached garage, covered front porch, and flexible space throughout. Great opportunity for an owner-occupant or investor. Unit 1 offers approximately 1,453 sq. ft. with 3 bedrooms and 1 full bath. The first floor features a large bedroom, spacious living room, kitchen, and full bath, with two additional bedrooms upstairs. The unit also has access to an approximately 1,201 sq. ft. unfinished basement with washer and dryer and plenty of storage space. Unit 2 offers approximately 1,026 sq. ft. with 2 bedrooms and a 3/4 bath. It includes a living room, kitchen, large bedroom with balcony, second bedroom, and approximately 216 sq. ft. of additional attic/storage space on the third floor. The property also includes a 462 sq. ft. detached garage and off-street parking. Convenient opportunity to live in one unit while renting the other, or add a two-family property to your investment portfolio. Furniture shown in the photos can be included with the sale at no additional cost.

19 Bellevue St, Windham

$424,900

5 Beds ⋅ 2 Baths ⋅ 24209915 MLS

Over 2,100 SF of beautifully updated living space awaits at 990 Riverside Drive! A welcoming farmer's porch adds to the curb appeal, while the home itself has been extensively renovated over the past approximately 10 years, including plumbing, electrical, HVAC with central air, insulation, kitchen, baths, flooring, paint and more. The spacious first floor offers a gorgeous kitchen with granite counters, abundant cabinetry, a new slider to the oversized deck and stairway leading to the upper level. An oversized dining room provides plenty of room for gatherings and entertaining, while the pellet stove offers an economical supplemental heat source. The enormous foyer offers incredible flexibility as an office, playroom, sitting area or additional living space as well as the second access to the upper level. A separate first-floor bedroom, office or flex room with access to the deck adds even more versatility. Upstairs are 4 generously sized bedrooms all completely updated. The second-floor bath is a standout with a whirlpool tub, double vanity, solid-surface counters, separate tiled shower, tile flooring and generous built-in storage. A walk-up attic and full basement provide excellent additional storage. Outside, enjoy the oversized deck, farmer's porch and detached 2-car garage. Conveniently located near the MA and RI borders with easy highway access, making commuting throughout the region a breeze. This is as turnkey as you are going to get with tons of space!!

990 Riverside Dr, Thompson

$270,000

2 Beds ⋅ 2 Baths ⋅ 24209356 MLS ⋅ Heritage Pines Estates BLDG.

Welcome to Heritage Pines Estates, where comfort, convenience, & low-maintenance living come together in this extensively renovated 2-bedroom, 2-full-bath condo. Nearly every aspect of this unit has been thoughtfully crafted, with an emphasis on quality workmanship & attention to detail. The renovations include new cabinetry, granite countertops, backsplash, stainless steel appliances, sinks and vanities, updated light fixtures, new flooring, new interior doors, new windows, and professional painting throughout. Thoughtful finishing touches, including a shiplap accent wall and custom shelving, add character and showcase the attention to detail carried throughout the renovation. A new washer and dryer and new hot water tank complete the improvements. The result is a beautifully finished home where the work has already been done, just move in and enjoy. Professionally managed Heritage Pines Estates offers the ease of condo living with two assigned parking spaces and an HOA that includes snow removal, lawn care, trash pickup, and access to the clubhouse. Centrally located near shopping, dining, entertainment, medical facilities, I-395 and Route 44, plus an easy commute to RI & MA. Just minutes from downtown Putnam and its popular restaurants, shops, and local attractions. HOA Fee: $353/month, Pet-friendly with restrictions.

67 Perry St Unit 114, Putnam

$449,900

4 Beds ⋅ 2 Baths ⋅ 24209513 MLS

Welcome to 78 Hammond Hill Road, a charming New England Cape set on approximately 1.7 picturesque acres in peaceful Hampton Connecticut. This inviting four-bedroom home offers about 2,000 square feet of living space, surrounded by mature landscaping and beautiful countryside views. Enjoy summer days by the in-ground pool, relax overlooking the rolling wooded hills, or explore the spacious grounds and private pond. A detached two-car garage, solar, and additional unfinished space with in-law potential add versatility. This is a wonderful country retreat offering privacy, character, native plants, fruit trees and a quaint private pond. The attached in-law apartment is adjoining and shares the quintessential northeastern Connecticut scenery of Hammond Hill.

78 Hammond Hill Rd, Hampton

$2,500,000

5 Beds ⋅ 6 Baths ⋅ 24198180 MLS

Welcome to Ufton Estate, a remarkable 41-acre private estate where historic character, exceptional craftsmanship and modern luxury come together in an extraordinary setting. Originally built in 1850 and thoughtfully reimagined in the early 1900s, the residence is filled with distinctive architectural details. Intricate hand-carved woodwork, elegant millwork and grandly proportioned rooms reflect the artistry of another era. Each space offers a sense of history while remaining comfortable, inviting and well suited to modern living. The home provides an impressive backdrop for both everyday life and memorable gatherings. Gracious entertaining spaces flow throughout the residence, complemented by intimate rooms that invite relaxation. Abundant windows frame views of the surrounding landscape and fill the interiors with natural light. Outside, the estate unfolds across 41 private acres with a heated pool, greenhouse, established gardens and expansive lawns. The beautifully layered grounds provide a timeless setting with endless opportunities for personalization. Reimagine the gardens and greenhouse, introduce an equestrian or agricultural component, enhance the outdoor entertaining spaces or simply enjoy the privacy and natural beauty of the estate as it is.

357 Wrights Crossing Rd, Pomfret

$400,000

4 Beds ⋅ 2 Baths ⋅ 24208690 MLS

Vintage 1944 home in the heart of Dayville, set on 2.5 acres at a convenient corner location close to shopping and with easy highway access, close to the Mass & RI lines. The attached garage provides convenient access to the home. The quaint kitchen features cozy bench seating, built-in glass-front storage perfect for displaying collectibles, and a door leading to the screened front porch-an inviting spot to enjoy morning coffee and the changing seasons. The spacious living room offers a sunny bay window, sliders to a private rear patio, hardwood floors, and a cozy fireplace creating a warm and inviting gathering space. The first floor includes a primary bedroom, an additional bedroom or office, and a full bath. Upstairs are two generously sized bedrooms, a large hallway closet, and another full bath. A detached outbuilding offers versatile space for a studio, workshop, or hobby area. Being sold AS IS, this solid home offers an opportunity to bring your vision and updates while preserving its vintage charm and character.

10 Homestead Rd, Killingly

$779,000

5 Beds ⋅ 4 Baths ⋅ 24209434 MLS

Set high on historic Woodstock Hill, this distinctive 19th-century property offers a rare combination of history, character, exceptional views, flexible living spaces, guest accommodations, gardens, and opportunity. Offering approximately 2,500 square feet, this beautifully maintained home features five bedrooms and three-and-a-half baths, along with multiple living areas and a beautiful sitting porch overlooking the surrounding landscape. The home has been thoughtfully adapted to accommodate both private living and hospitality, creating flexibility for a variety of lifestyles. Two separate, thoughtfully furnished guest suites provide an established short-term rental opportunity and have enjoyed strong bookings. Guests have included parents visiting their children attending Woodstock Academy and Pomfret School, families attending weddings and local events, and visitors seeking to experience the beauty and charm of Woodstock. The grounds offer another exceptional dimension. Flower-growing areas, gardens, and a flower stand have been developed by the current owners during their first year on the property, building upon their longstanding experience with gardening and growing. The property offers an exciting opportunity to continue and expand the flower-growing vision, create a garden-based business, or explore the possibility of a future studio or shop, subject to applicable approvals.

500 Rte 169, Woodstock

$449,900

3 Beds ⋅ 3 Baths ⋅ 24209472 MLS

Situated along Wolf Den Dr, as it passes directly through Mashamoquet State Park, this exceptional location is a dream for nature enthusiasts, hikers, and trail riders alike. Just a short walk from your door you'll access miles of scenic state park trails and pristine outdoor beauty (See attached trail map for full details). Welcome to this 2000-built raised ranch offering 1,775 sq. ft. of living space and a layout that is exceptionally rare for this style of home. Unlike traditional raised ranches with clustered bedrooms, this smart floor plan features a private primary suite with an en-suite bath on one side, while two guest bedrooms and a full bath sit on the opposite end for optimal privacy. At the center of the main level, an open-concept kitchen, dining, and living area forms the heart of the home. The lower level extends your living space with a large family room, utility room, and a half bath/laundry room. Situated on a quiet and peaceful street; the property features a serene and quiet yard with no neighbors directly in front or behind. The sprawling cleared 1.4-acre lot features an upper deck, an expansive lower deck, and an above-ground pool-perfect for summer relaxation and outdoor gatherings. Located just 3 minutes to the PreK-8 school and less than 15 minutes to Woodstock Academy, shopping, dining, and I-395 for easy commutes to MA and RI. With incredible potential, space, and a hard-to-find layout, this home is a fantastic find! Schedule your appointment today

45 Wolf Den Dr, Pomfret

$544,900

3 Beds ⋅ 3 Baths ⋅ 24209290 MLS

Privacy, space & comfort come together at 345 Cook Hill Rd, set on over 6 acres of private land in Killingly close to the RI border! This well-maintained 3-bedroom, 2.5-bath home offers a spacious, open layout designed for everyday living & entertaining. The kitchen has been lovingly cared for and features updated solid-surface counters, timeless wood cabinetry & plenty of workspace, opening to the main living area with a cozy propane fireplace. A flexible dining room/office provides the perfect space for formal dining, working from home, a playroom or additional living space. Convenient 1st-floor laundry is located in the half bath. Upstairs you'll find 3 comfortable bedrooms & 2 full baths including spacious primary suite. Outside, enjoy the peace and privacy of the expansive property from the deck, porch or patio, along with an above-ground pool for summer enjoyment. The 2-car garage includes additional storage & a workbench, while the full basement provides plenty of room for storage, hobbies or future possibilities. Underground utilities add to the clean setting and curb appeal. A private retreat with acreage, flexibility & plenty of room to enjoy inside and out.

345 Cook Hill Rd, Killingly

$379,900

5 Beds ⋅ 2 Baths ⋅ 24209326 MLS

Discover the possibilities at 8 Dyer St in Killingly, a versatile two-unit property offering a unique combination of residential space, parking, and flexible layouts. One of the two units has been fully converted from a former commercial storefront, creating a distinctive living space with an open and adaptable floor plan. The property features two generously sized bedrooms on the first floor, while the second-floor unit offers three bedrooms, providing plenty of room for residents, guests, a home office, or additional living space. Additional highlights include a two-car garage with convenient interior access and off-street parking, adding valuable storage, convenience, and functionality. Whether you're looking for an investment property, owner-occupied multifamily, or a property with flexible residential possibilities, 8 Dyer St offers a unique opportunity in Killingly

8 Dyer St, Killingly

$393,000

4 Beds ⋅ 2 Baths ⋅ 24209373 MLS

Welcome to this inviting 4-5 bedroom, 2-bath Colonial in the heart of Danielson, CT. Set on a generous .35-acre lot with 1,904 square feet of living space, this two-story home blends classic charm with everyday comfort. Gleaming hardwood floors run through the kitchen, living room, and dining room, while the sun-filled living room addition, built in 1999, adds extra space to spread out. The kitchen was refreshed about eleven years ago with new cabinets and countertops, and nearly every appliance has been updated in recent years, with the exception of the microwave. Siding and windows were replaced in 2007, the roof is roughly eleven years old, and the furnace is about 2 years old, meaning many of the big-ticket updates are already done. Upstairs, the bedrooms feature carpet and paint that were refreshed within the past couple of years. Additional highlights include a detached 2-car garage and a walk-up attic filled with natural light from its front-facing windows, perfect for storage or future finished space. Outside, enjoy a large back deck and a fully fenced yard. All of this in a peaceful residential neighborhood with easy access to local roads and amenities. This home truly offers the perfect mix of comfort and convenience.

85 Robertson Ave, Killingly

$399,900

4 Beds ⋅ 2 Baths ⋅ 24209211 MLS

Step into this beautifully maintained 1885 home full of charm and character. The home is in great condition, with updates of roof, exterior paint, windows, wood floors, boiler and electric panel. Crown molding and high ceilings throughout the main level combine to add warmth and flair. A formal living room, family room with built-ins, and large dining area accommodate entertaining, or relaxed living. The primary bedroom suite is on the 2nd level, and features a sitting area, propane fireplace, walk-in closet, and full bath. Host the next gathering on the wrap around porch, complete with haint blue ceiling, or just sip apple cider with a friend. The barn provides great space for storage, hobbies or a workshop. After 50 years, this property is ready for it's next owner.

225 Woodstock Ave, Putnam

$225,000

24209300 MLS

Picturesque lot with building site off the road. Ready to go with testing complete for a 5 bedroom home. Build your dream home!

Church Street, Thompson

$895,000

12 Beds ⋅ 12 Baths ⋅ 24209225 MLS

Rare six-family investment opportunity featuring six townhouse-style units! Built in 1981, this exceptionally clean and well-maintained property offers 5,400 square feet of living space with six identical, turnkey 2-bedroom, 1.5-bath layouts. Each unit features main-level living space with a convenient half bath, two bedrooms and a full bath upstairs, private laundry hookups, and its own private basement offering additional storage and utility space. Designed with investment ownership in mind, the property features public water and sewer, individually metered electricity, and tenant-paid electric baseboard heat-helping limit owner-paid utility expenses. A private paved driveway and parking area, along with a 0.55-acre lot, complete the property. All occupied units are currently month-to-month, offering flexibility for the next owner. Purpose-built six-family properties with townhouse-style layouts like this are a rare find. A compelling opportunity to acquire a clean, turnkey multifamily asset with existing income and meaningful potential for future growth.

82 Hutchins St, Killingly

$550,000

2 Beds ⋅ 1 Baths ⋅ 24209159 MLS

204 Pine Hollow Road-an exceptional waterfront opportunity on beautiful Alexander's Lake. Enjoy the very best of the lake lifestyle, with a functional one-car garage offering valuable additional storage and bonus space. A special property in a truly special setting!

204 Pine Hollow Rd, Killingly

$699,900

3 Beds ⋅ 2 Baths ⋅ 24208396 MLS

Investors and homeowners, take notice! Welcome to The Gathering House, a breathtaking 1837 Greek Revival church seamlessly transformed into a stunning, turnkey residence. Nestled in historic South Killingly, this architectural gem underwent a complete, top-to-bottom restoration. Today, it stands as a fully furnished, 5-star Airbnb/VRBO destination, an exceptional second home, and the ultimate venue for grand-scale entertaining.The main level is dedicated to hosting. Step into the spectacular 1,200 sq ft multi-purpose great room, boasting soaring 14-foot ceilings and flooded with light from seven massive 10-foot windows. This jaw-dropping space features a built-in stage, dining area, comfortable seating for a crowd, and an 85" TV with a sound bar. A convenient kitchenette and half bath are located adjacent to the great room to effortlessly serve your guests.The lower level offers a beautifully designed residential retreat. It features a gorgeous, open-concept kitchen, dining area, and cozy den, alongside 3 bedrooms and a full bathroom. The fully equipped kitchen is ready for business, showcasing rich cherry cabinetry and elegant granite countertops with bar seating. Two bedrooms feature large walk-in closets, while the spacious full bath includes a linen closet and an all-in-one washing machine.Don't miss this incredible turnkey opportunity. Check out the 3D tour and read the glowing guest reviews! The listing agent is one of the owners.

160 Halls Hill Rd, Killingly

$295,000

2 Beds ⋅ 2 Baths ⋅ 24208659 MLS

Situated on a tranquil lot in a quiet Ashford neighborhood, this inviting 2-bedroom, 2-bathroom ranch offers an open floor plan and versatile living spaces across two levels. Step inside to a light-filled main level where the spacious living room features low-maintenance vinyl flooring and glass sliders opening directly onto the back deck. The remodeled eat-in kitchen (2023) boasts sleek granite countertops, generous cabinet storage, and a dedicated eating area for daily meals. Two well-proportioned bedrooms with vinyl flooring and ample closet storage complete the main level, along with a full bath. Downstairs, the partially finished lower level expands your options with vinyl flooring and flexible additional rooms, ideal for a home office, recreation room, and/or gym. Sliders lead out to a private patio overlooking a peaceful, wooded backyard, creating a wonderful setup for outdoor relaxation and quiet mornings. Major recent improvements include a new hot water heater (2024) and a new roof (2025) for added peace of mind. Enjoy the serene setting while staying conveniently connected. The property offers easy access to major highways and state roads, as well as excellent proximity to UConn Storrs, local dining, and surrounding state parks. Schedule your private showing today!

31 Chetelat Dr, Ashford

$365,000

8 Beds ⋅ 2 Baths ⋅ 24208553 MLS

Excellent opportunity to own a spacious two-family home offering flexibility for owner-occupants or investors. Each unit features 4 bedrooms and 1 full bath. Both units have their own utilities. Outdoors, each unit enjoys its own backyard area separated by fencing, creating defined outdoor spaces for each residence. A detached 2-car garage provides additional parking and storage, adding even more value. Whether you're looking to live in one unit while generating rental income from the other or add a multi-unit property to your investment portfolio, this two-family home is well worth a look!

137-139 S Chestnut St, Plainfield

$500,000

3 Beds ⋅ 3 Baths ⋅ 73580137 MLS

SELLER OFFERING CLOSING COST CREDIT!"Exceptional Raised Ranch with Custom Greenhouse, New Composite Deck, Solar & Flexible Finished Lower Level" Welcome to this thoughtfully enhanced 3-bedroom, 2.5-bath raised ranch set on 0.75 beautifully maintained acres in North Grosvenordale. Offering 2,628 square feet of living space, this home combines comfortable everyday living with exceptional spaces for entertaining, gardening, fitness, and relaxation. The spacious eat-in kitchen provides direct access to a custom-built greenhouse, making it easy to enjoy gardening throughout the seasons. Outside, established gardens and a brand-new composite deck create a wonderful setting for morning coffee, outdoor dining, or just relaxing. The main level features two professionally designed full bathrooms, including one with a walk-in shower and another with a luxurious soaking tub. The finished lower level provides impressive versatility, with 2 separate exterior entrances, pellet stove, half bath, laundry, and a state-of-the-art exercise space. The garage-under has been transformed into a dedicated home gym and could offer additional possibilities for recreation, hobbies, or potential in-law accommodation, subject to buyer verification and applicable requirements. Additional highlights include new water heater and solar panels. Originally built in 1965, this unique property has been designed to offer modern amenities while maintaining the character and functionality of a classic raised ranch.

1 Corttiss Rd, Thompson

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