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291-293 School 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

183 Hillside Rd, Ashford
$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

111 Corey Rd, Canterbury
$649,000
3 Beds ⋅ 3 Baths ⋅ 24209263 MLS
Privacy abounds at this impeccably maintained, custom-built Colonial nestled on over 20 private, wooded acres. Loving care shines through from the original owner of this 2001 gem, featuring a unique and thoughtful floor plan. The main level boasts gleaming hardwood floors, a bright and sunny eat-in kitchen with sliders to the rear deck, and distinct family and living rooms separated by beautiful glass French doors. Stay cozy this winter with the woodstove, perfectly positioned to lower your heating bills with a endless supply of firewood right from your own land! Upstairs, the primary suite offers a peaceful retreat with a private full bath and walk-in closet. Two additional bedrooms flank a shared landing, sitting just steps down the hall from a second full bath that conveniently houses the laundry. A clever hallway nook makes the perfect crafting corner or mini-library, leading into a gigantic bonus room-currently a fantastic billiards and gaming space with endless possibilities. Complete with central air, a classic front porch, a 2-car attached garage, and flexible Canterbury high school choices, this peaceful oasis is within walking distance to the Kinne Preserve hiking trails while remaining an easy commute to major highways. Schedule your private showing today!

111 Corey Rd, Canterbury

346 Church St, Putnam
$399,000
4 Beds ⋅ 2 Baths ⋅ 24208130 MLS
A great opportunity to call Putnam home while enjoying the added benefit of rental income! This spacious two-family property offers approximately 3,198 square feet of living space, with two bedrooms and one full bath in each unit. One unit will be delivered vacant, making this an ideal setup for an owner-occupant looking for the comfort of their own space while having rental income from the second unit help offset monthly expenses. Inside, you'll find generous living areas, hardwood floors, and classic character throughout, along with a functional two-family layout that offers plenty of flexibility. A detached two-car garage and driveway provide convenient off-street parking and additional storage. Recent improvements include a new roof in 2025 and a new water heater. An in-ground pool is located on the property but is currently not in use. Conveniently located in Putnam, you'll be close to downtown, restaurants, shopping, recreation, and everyday amenities, with I-395 just minutes away for an easy commute. With one unit being delivered vacant and the flexibility that two-family living provides, this property offers a practical way to enjoy more space while helping offset the cost of homeownership.

346 Church St, Putnam

130 N Frontage Rd, Killingly
$399,000
3 Beds ⋅ 1 Baths ⋅ 24210130 MLS
Welcome to your new home. An updated raised ranch on nearly 2 private acres, beautifully maintained, move-in ready. Inside you will find rich, hardwood floors throughout. There is a large, open kitchen with granite countertops and newer, stainless appliances. The bathroom has also been renovated to include a new shower and sink. You will find comfort throughout the year with central air and a wonderful wood stove to cozy up to. Within the last 2 years a brand new boiler, along with a 40 gallon hot water tank, and a 3-stage water filtration system has been installed. Downstairs you will find an almost finished basement that can be used as an office or family room, and utility room with shelves and cabinets. There is also a great 2 car garage with plenty of storage and work benches for your next project. Step outside on the newer deck to enjoy a beautiful backyard, fire pit, and low maintenance landscaping. Start your own small homestead with chicken coop, greenhouse and compost bin and shed.The house is generator ready and a tri-fuel Winco generator can be made available upon request. Plenty of places for outdoor activities nearby, Old Furnace State Park, Ross Pond State Park, minutes away.

130 N Frontage Rd, Killingly

Aplin Hill Ln, Woodstock
$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

111 Ashford Center Rd, Ashford
$385,000
4 Beds ⋅ 4 Baths ⋅ 24198024 MLS
One-of-a-kind Ashford home in an extraordinary country setting! Offering approximately 2,866 sq. ft., 4 bedrooms and 3.5 baths, this distinctive home has evolved over the years into a wonderfully flexible floor plan well suited to multigenerational living, working from home or simply spreading out. Character is everywhere, from wide-board wood floors and exposed beams to two fireplaces and a terrific library with extensive built-ins. The spacious kitchen, multiple living areas and combination of first- and second-floor spaces offer possibilities rarely found in a conventional home. Set on 1.71 acres with garage, outbuildings, open yard and wooded surroundings, the setting is equally special. Immediately beyond the property is Joshua's Trust's 60+ acre Josias Byles Sanctuary, with extensive Boy Scouts of America land farther beyond, creating an exceptional backdrop of woods, wildlife and open space. The home is livable now while offering plenty of opportunity for its next owner to make it their own. Refinishing the wood floors, exterior painting and other thoughtful improvements could make a remarkable difference. A truly unusual property for buyers who value space, character, flexibility and nature.

111 Ashford Center Rd, Ashford

106 Church Street, Brooklyn
$744,999
3 Beds ⋅ 3 Baths ⋅ 1424643 MLS
Approved building lot on desirable street, property is on a shared driveway. TO BE BUILT: A 2,020 sqft., 3 bedroom, 2.5 bath colonial style home sits on a beautiful 2.6 acre lot. The kitchen features a tile backsplash, oversized island, stainless steel range hood, pantry cabinet, and quartz countertops. The living room flows from the kitchen creating an open feel. Hardwood flooring throughout the home. The staircase is a wonderful centerpiece of the home, with banisters and iron balusters. Upstairs you will find 3 large bedrooms. The primary bedroom features a walk-in closet and attached bath with tile shower and double sink vanity. Forced hot air and A/C climate control the home. Attached 2 bay garage, back deck, walk out basement and front porch are just a few other wonderful features.

106 Church Street, Brooklyn

32 Ashford Rd, Eastford
$435,000
3 Beds ⋅ 2 Baths ⋅ 24209461 MLS
If you've been searching for true country living, privacy, and land for exploration, this 17-acre property in Eastford delivers all of it. With Bigelow Brook (a Class A trout brook), running through the acreage and the Natchaug Blue Blaze Trail crossing the land, this is a dream setting for outdoor enthusiasts, nature lovers, and anyone seeking a peaceful retreat. The location places you near Natchaug State Forest, Ashford Lake, and between Buell's and Crooks orchards. The Cape Cod home is set back from the road, giving the ultimate sense of privacy. Inside, the large eat-in kitchen features a large moveable island, pantry closet, updated quartz countertops, luxury vinyl flooring, induction stove, newer refrigerator, and an elegant wood hood. Just off the kitchen is a flexible first floor bedroom or home office with double closets and stunning cherry wood floors milled from trees harvested on the property. The living and dining rooms continue the cherry flooring and offer a warm gathering space with a woodstove for alternative heating. A French door leads to the back deck with a ramp from the driveway, and overlooking the backyard and peaceful tree line. A full bath with tub/shower completes the main level. Upstairs are two bedrooms, a full bath, and a walk-in hallway closet. The larger bedroom includes a Jotul woodstove for additional heating, and both rooms feature skylights that fill the space with natural light.

32 Ashford Rd, Eastford

154 Manners Ave, Windham
$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

89 John Perry Rd, Eastford
$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

35 Sterling Ridge Ln Unit 29, Sterling
$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

11 Otis St, Killingly
$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

6 Old Rte 12, Thompson
$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

66 High Meadow Dr, Plainfield
$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

19 Bellevue St, Windham
$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

990 Riverside Dr, Thompson
$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

67 Perry St Unit 114, Putnam
$267,500
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

78 Hammond Hill Rd, Hampton
$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

357 Wrights Crossing Rd, Pomfret
$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

10 Homestead Rd, Killingly
$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

500 Rte 169, Woodstock
$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

11 Type Rd, Windham
$315,000
4 Beds ⋅ 2 Baths ⋅ 24207636 MLS
Investors and owner-occupants, take notice! This well-maintained two-family home is ideally situated on a quiet dead-end street and offers an excellent opportunity for both rental income and owner occupancy. One unit is currently unoccupied, providing flexibility for a buyer looking to move in while generating rental income from the second unit. Each spacious unit features 2 bedrooms, 1 full bath, and approximately 1,000 square feet of living space, with comfortable layouts and strong rental appeal. Separate utilities simplify ownership and management, while basement laundry hookups provide added convenience for tenants. Set on nearly half an acre, the property offers plenty of outdoor space, a welcoming front porch, and an abundance of off-street parking. Conveniently located near shopping, dining, schools, and major routes, this property combines a peaceful setting with easy access to everyday amenities. Whether you're looking to expand your investment portfolio or take advantage of an owner-occupied opportunity, this versatile two-family property is ready to deliver flexibility, space, and potential. Highest and Best by 8pm Friday 10/10/2026.

11 Type Rd, Windham

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