Windham County Homes under $1.5 million

Welcome to Windham County, Connecticut, a hidden gem nestled in the heart of New England. Known for its picturesque landscapes, rich history, and vibrant communities, Windham County offers a unique blend of rural charm and modern conveniences. With its lush forests, serene lakes, and rolling hills, outdoor enthusiasts will find plenty of opportunities for hiking, fishing, and exploring nature.

Windham is home to a diverse array of towns, each with its own character and charm. From the quaint streets of Willimantic, known for its historic architecture and lively arts scene, to the peaceful surroundings of Mansfield, where you can enjoy the beauty of the University of Connecticut campus, there’s something for everyone here. The county also boasts excellent schools, making it a great place for families to settle down.

For those looking to invest in real estate, Windham County offers an impressive selection of homes under $1.5 million. Whether you’re seeking a cozy cottage, a spacious family home, or a modern new build, you’ll find a variety of options to suit your lifestyle. Many properties feature stunning views, expansive yards, and easy access to local amenities.

With its affordable housing market and welcoming communities, Windham County is not just a place to live; it’s a place to thrive. Discover the perfect home in this enchanting region of Connecticut, where you can enjoy the tranquility of nature while being just a short drive from vibrant cities and bustling activities. Come and explore all that Windham County has to offer!

Newest Windham County Homes under $1.5 million

$269,900

3 Beds ⋅ 1 Baths ⋅ 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 ⋅ 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 ⋅ 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 ⋅ 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 ⋅ 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 skylight that fills the space with natural light, 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 painted just a few years ago, and the spacious 14' x 21' deck was recently painted and is ready for outdoor entertaining. Outside, the property offers a beautiful, open and level lot along with a substantial 12' x 26' 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 ⋅ 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

$699,900

5 Beds ⋅ 4 Baths ⋅ 24211323 MLS

Welcome to your private country retreat! Set on approximately 2 acres overlooking a beautifully groomed field, this exceptional property offers unparalleled space, privacy, and versatility. The main residence features 5 bedrooms, 3.5 baths, hardwood floors throughout, a second-floor laundry area, and a spacious bonus room above the garage. Adding incredible value is the full walk-out in-law suite featuring 1 bedroom, 1 full bath, a full kitchen, living and dining areas, dedicated washer/dryer hookups, a private driveway, separate entrance, and its own 16x16 covered deck-perfect for multigenerational living or potential rental income. Step outside to your ultimate outdoor oasis, complete with an above-ground swimming pool with surrounding deck, hot tub, treehouse, and a 16x16 heated shed with a wood stove. The detached garage is fully equipped with heat, AC, electricity, and internet, making it an ideal workshop, home gym, or studio space. Best of all, the home includes 37 fully paid-for solar panels paired with two electric heat-pump systems for exceptional energy efficiency. Properties offering this rare combination of amenities, flexibility, and charm don't come along often-schedule your showing today!

2 Logans Way, Sterling

$355,000

4 Beds ⋅ 1 Baths ⋅ 24211424 MLS

RAISED RANCH: This 1,700-square-foot raised ranch offers 4 bedrooms, 1 full bath, and versatile space to fit your needs. Hardwood and carpet flooring add warmth, while an additional lower-level room provides options for a home office, storage, or other use. A laundry area adds everyday convenience. Recent updates include a new roof in 2024, a new deck and above-ground pool in 2025, and a renovated bathroom in 2026. Spend warmer days relaxing on the deck or enjoying the pool, with a shed offering extra storage for outdoor essentials. Additional features include solar panels, electric heat, and city water and sewer. Conveniently located near downtown, shopping, and walking trails, with easy access to Interstate 395, this home keeps everyday destinations within reach.

78 Viens St, Putnam

$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

$529,900

3 Beds ⋅ 2 Baths ⋅ 24180667 MLS

Set privately on 10 acres, this beautiful 3-bedroom, 3-bath home is in excellent condition and offers the privacy you've been looking for. The open floor plan creates an inviting flow between the living, dining, and kitchen areas, with a spacious kitchen island providing the perfect gathering spot for everyday living or entertaining. Sliding doors open directly to the back deck, extending the living space outdoors and offering a peaceful setting surrounded by your own acreage. The finished lower level with a full bathroom provides valuable additional living space and flexibility for a family room, home office, recreation area, or guests. The oversized two-car garage offers plenty of room for vehicles, equipment, hobbies, and storage, with additional, easy access, storage space above. Every area of the home has been exceptionally cared for, with a fresh, cohesive feel throughout and attention to detail evident in the finishes and overall presentation. Surrounded by 10 acres of private land, this is a rare opportunity to enjoy a comfortable, move-in-ready home with room to spread out while still having convenient access to everything you need. Every area of the home has been exceptionally cared for, with a fresh, cohesive feel throughout and attention to detail evident in the finishes and overall presentation. Surrounded by 10 acres of private land, this is a rare opportunity to enjoy a comfortable, move-in-ready home.

155 Tripp Hollow Rd, Brooklyn

$329,000

2 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 classic charm along with several recent updates, including a new roof, new carpeting, and a recently reglazed tub and sink, making it move-in ready and easy to maintain. Each unit features 2 bedrooms, 1 full bath, a kitchen, living room, and an enclosed front porch that provides additional living space. Each unit has its own utilities. 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, perfect for relaxing, gardening, or entertaining. 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

$385,000

3 Beds ⋅ 1 Baths ⋅ 24211687 MLS

Welcome to 62 Bates Pond Road in Canterbury, Connecticut - a 3 bed 1 bath SFR with a newly finished basement on a little over 2 acres of land. This property offers privacy, space, and comfortable living in a peaceful setting. Come see what this Canterbury property has to offer.

62 Bates Pond Rd, Canterbury

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