Windham County Homes under $750,000

Welcome to Windham County, Connecticut, a hidden gem nestled in the heart of New England. Known for its picturesque landscapes, charming small towns, and rich history, Windham County offers an inviting atmosphere for families, retirees, and anyone seeking a peaceful lifestyle. With its lush greenery, stunning parks, and vibrant community events, this county is perfect for those who appreciate the beauty of nature combined with a warm, welcoming community spirit.

One of the most appealing aspects of Windham County is the diverse array of homes available for under $750,000. Whether you're searching for a cozy cottage, a spacious family home, or a modern townhouse, you’ll find a variety of options that fit your budget and lifestyle. The real estate market here is thriving, with properties that boast modern amenities while still retaining that classic New England charm. Many homes feature sprawling yards, updated kitchens, and easy access to local attractions, making them ideal for both relaxation and entertainment.

Living in Windham County means enjoying a slower pace of life while still being close to urban conveniences. Explore the local farmers' markets, indulge in the rich culinary scene, or take a stroll through one of the many beautiful parks. With excellent schools, a strong sense of community, and a plethora of outdoor activities, Windham County is not just a place to live—it's a place to thrive. Discover your dream home in this enchanting county and experience all the warmth and beauty it has to offer!

Newest Windham County Homes under $750,000

$599,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$479,000

12 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24212338 MLS

This 1920 multi-family offers 2,516 sq ft of living space with one unit per floor. It has natural gas heat and natural gas water heaters, and public water and sewer keep maintenance simple. Off-street parking adds convenience for tenants. The building sits on Spring Street, across from Chestnut Street, just minutes from downtown Willimantic, Eastern Connecticut State University, shopping, dining, and major routes, with UConn a short drive away. It's a solid opportunity to add a well-located income property to your portfolio or to live in one unit and let the others help pay the mortgage. Schedule your showing today!

66 Spring St, Windham

$369,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24210680 MLS

Welcome to easy one-floor living at 1310 Route 169 in desirable Woodstock! Set on 0.6 acre, this thoughtfully updated home offers comfort, convenience and a peaceful outdoor setting. Step onto the large deck and enjoy a beautiful open backyard, where gardens and woodland views create a private retreat for morning coffee, summer gatherings or simply unwinding. Inside, updated flooring and granite countertops in the kitchen and bathroom add style, while the dining room window welcomes natural light. First-floor laundry makes everyday living easier. The open walk-out basement offers room for hobbies, storage and potential future expansion, with a pellet stove for added warmth. Numerous improvements include updated doors, a new water heater in 2023, and a freshly updated bathroom vanity. A new 20x20 two-car carport, added in 2026, complements the asphalt driveway. The 1,500-gallon septic tank was replaced in 2021 and the roof in 2011. A washer, dryer and generator with a whole-house plug-in connection are included. Enjoy the charm of Northeast Connecticut with convenient access to Massachusetts and I-395 in Putnam - a welcoming place to settle in and make your own.

1310 Rte 169, Woodstock

$499,900

6 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 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. Come see this hidden gem before its gone!

9 Ellen Ln, Woodstock

$339,900

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24212044 MLS

Welcome to 42 Church Street in Thompson! This move-in-ready home offers 3 bedrooms and 2 full baths with a comfortable layout and plenty of flexible living space. The main level features a spacious living room, 3 bedrooms, and a full bath, while the lower level includes an additional full bath and offers great potential for a family room, home office, gym, or guest space. The home has been refreshed from top to bottom with brand-new luxury vinyl plank flooring throughout and fresh interior paint, giving it a clean, updated feel that's ready for its next owner. Outside, enjoy an extremely private lot with plenty of space to relax, entertain, garden, or simply enjoy the peaceful surroundings. A huge storage shed provides excellent additional space for tools, lawn equipment, hobbies, and more.

42 Church St, Thompson

$425,000

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 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

$269,900

3 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 24211718 MLS

Priced to sell at $269,900, this move-in ready ranch home features a newer roof and the perfect blend of peace, privacy, and everyday convenience. Built in 1975, this ranch home offers 1,152 square feet of single-level living space situated on a spacious, level .91-acre lot. All kitchen and laundry appliances are included, allowing for a seamless transition. The functional Layout offers three comfortable bedrooms, one full bathroom, ideal for effortless single-level living. Features a large parking area with plenty of room for multiple vehicles, all set on a massive, level yard perfect for gardening, outdoor entertaining, or recreation. Centrally located, this home keeps you connected to everything you need. You are situated just minutes from Interstate I-395, offering incredibly quick access to area shopping plazas, diverse dining options, and local conveniences. Don't miss this fantastic opportunity to own a peaceful retreat with unbeatable modern accessibility at an incredible price point!

44 Putnam Rd, Plainfield

$315,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24211972 MLS

Welcome home to this well-cared-for ranch offering comfortable, easy one-level living! Featuring an attached one-car garage, a nice flat front and backyard, and a fenced-in outdoor space, this home is ready to enjoy. Inside, you'll find hardwood floors throughout the living room, hallway, and bedrooms. The clean and functional kitchen offers plenty of cabinet space and a window overlooking the backyard, while the sunroom/rec room off the back provides great additional living space. Updates include a UV filtration system for the well installed in 2019, an updated boiler and newer oil tank. Central AC that gets serviced yearly. Clean, comfortable, and move-in ready! Property is being sold as-is.

45 Fairview St, Killingly

$625,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24211826 MLS

Wake up to the water every day on Moosup Pond! This custom post-and-beam timber-frame Contemporary A-Frame offers direct waterfront with a private beach area, a stone path to the shoreline, room for two docks, and plenty of entertainment space. Bring the kayaks and the boat! Inside, soaring cathedral ceilings, exposed beams, free-standing propane log fireplace, and floor-to-ceiling glass bring water views to all 3 levels. The open main level features a granite kitchen with stainless steel appliances and a wraparound breakfast bar, a sun-filled sunroom, gleaming hickory floors, two generously sized bedrooms, and first-floor laundry. Step out to the Trex deck spanning the full width of the home and enjoy unforgettable sunsets. The entire upper level is a private primary suite with a balcony overlooking the main floor and more water views, cathedral ceilings, skylights, and an en-suite bath with jetted tub and separate shower. The finished walk-out lower level is made for entertaining, with a family room, full bath, and custom wet bar, plus sliders to a covered patio where your hot tub awaits just steps away. Outside, a shed with a separate BBQ area completes the setting. Additional highlights include Andersen windows and sliders, split-system air conditioning, a whole-house generator, sprinkler system, & central vac system. This professionally landscaped home has 3 full baths and 2,588 sq ft across 3 levels of lakefront living with true character. This one won't last!

133 Pond Hill Rd, Plainfield

$269,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24211966 MLS

Full of character, this 3-bedroom, 2 full bath home offers a spacious and functional layout in a convenient, walkable location. The main level features a large living room, a spacious kitchen with plenty of room to cook and gather, a dedicated dining room, a versatile bonus room perfect for a home office or playroom, and the convenience of first-floor laundry. All three bedrooms are located upstairs, offering separation from the main living spaces. Connected to city water and sewer and close to shops, restaurants, schools, and everyday amenities, this home is ready for its next chapter.

602 N Main St, Killingly

$319,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24189966 MLS

This lovely home has been thoughtfully updated and well maintained over the years. Recent improvements include a brand-new 40-year roof, beautifully refinished hardwood floors, and fresh paint through the majority of the home. Additional updates include Anderson windows, newer interior and exterior light fixtures, a brand-new beautiful black granite slab for the fireplace, a hatchway, dual oil tanks, rounded archways, and solid six-panel doors. The kitchen features custom-made solid wood cabinetry, including convenient pull-out pantry drawers, along with a newer countertop. The full baths have also been updated, including a second-floor bath with a valuted ceiling, as well as two new toilets. The basement has been freshly sealed, with the walls and floor treated with Drylok for added protection. The exterior was freshly painted including the spacious 14' x 21' deck and is ready for outdoor entertaining. Outside, the property offers a beautiful, open and level lot along with a substantial 12' x 16' outbuilding, providing plenty of space for storage, hobbies, a workshop, or other possibilities. Inside, you'll find spacious bedrooms, with skylights on the second floor bringing in an abundance of natural light. With its classic Cape charm, numerous updates, flexible living space, and generous outdoor areas, this home offers a wonderful combination of character, comfort, and functionality.

75 Mullen Hill Rd, Windham

$379,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

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