Windham County, CT Real Estate Search

Windham County, CT Homes between $450,000 and $500,000 for Sale

Our website features the best real estate search for homes between $450,000 and $500,000 available in Windham County, CT and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest Windham County, CT Homes between $450,000 and $500,000 for Sale

$469,900
3 Beds 2 Baths 24203933 MLS
NOT YOUR TYPICAL RANCH! This exceptional ranch-style home offers an amazing contemporary floor plan with approximately 1400 square feet on the main level living space. Thoughtfully designed around a spacious central kitchen with multiple cabinets, granite counters, SS appliances and a corner built in table.The main level features three bedrooms, a full bath, a brand-new Kitchen creating a bright and inviting space for everyday living and entertaining and a living room with a pellet stove hearth. The improvements continue with new windows ,roof, and vertical siding installed in 2023 providing both modern appeal and peace of mind. Step outside onto the impressive 20' x 25' rear deck overlooking a beautiful flat, level and private yard. The perfect setting for outdoor dining, entertaining or simply relaxing. The fully finished lower level adds tremendous versatility and living space, offering three additional bedrooms, a living room, and a full bath along with a separate access. Whether you need space for guests. extended family, a home office, recreation, or additional living quarters this level provides endless possibilities and a perfect IN-LAW setup. A two-car garage adds convenience and functionality with its unique contemporary layout. Extensive updates, abundant living space, private level yard and exceptional flexibility, this is a ranch that truly stands apart from the ordinary. Come see all this special home has to offer!

478 Wauregan Rd, Killingly

$500,000
3 Beds 3 Baths 24204889 MLS
"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

$459,900
5 Beds 2 Baths 24199139 MLS
This beautiful 1740 antique Cape sits on a lovely 1.59 acres with the iconic stone walls of the area. The home is immaculate and ready for you to move right in. The first floor features a kitchen with the pantry everyone wants. In addition there is an impeccable butler's pantry with custom storage and display cases. The dining room is bright and can accommodate large family gatherings. There is a working fireplace in the sitting room and the office receives beautiful afternoon light. The sunny living room boasts a wood stove to keep you warm all winter. There is a first floor full bath & laundry. The second floor has four bedrooms, a full bath, and a large walk in attic. Other features include a screened porch, two barns, which would be ideal for a hobby farm or workshops/studios. There is a fenced-in area for pets, an above ground pool, a large garden area with two raised beds, in ground beds, 4 newly planted fruit trees, and an area for expansion. Half of the property is in the process of rewilding, but it has only been a year and can easily be returned to lawn if desired. Recent updates include a new roof in 2025 with a warranty ,which will convey, many replacement windows, new chimney cap, the well pump was replaced two years ago, and the woodstove was installed in 2025. The home is filled with charm and character and has a floor plan that provides many options. Schedule a time to view this exceptional Brooklyn property

136 Hartford Rd, Brooklyn

$500,000
4 Beds 4 Baths 24193694 MLS
Everyone loves a great wrap-around front porch, & this one feels like it was made for slowing down. Wrapped in classic columns & overlooking one of Connecticut's most scenic historic districts, this 1830 home offers 4 bedrooms, 3.5 bathrooms, & over 2,800 square feet filled with original character. Step inside to an elegant oak staircase, original hardwood floors, crown molding, & an interior that reminds you why people continue to fall in love with historic homes. The oversized living room is filled with natural light from dramatic floor-to-ceiling windows. A formal dining room flows into the eat-in farmhouse-style kitchen, where a remarkable brick fireplace once served as the home's original indoor cooking hearth. A first-floor en suite bedroom provides flexibility for guests, multigenerational living, or a private home office, while upstairs you'll find three additional bedrooms plus additional rooms ideal for offices, art studios, a library, or hobby space. Outside, the large rear deck overlooks a just over 3/4-acre, partially fenced lot with plenty of room to entertain, garden, or simply enjoy the outdoors. A new roof installed in 2026, solar panels that help offset electric costs, & a one-car garage add everyday convenience. Located along scenic Route 169 in Brooklyn's historic district, you'll enjoy the charm of Connecticut's Quiet Corner just five minutes from everyday conveniences & approximately 45 minutes from both Providence & Worcester.

31 Canterbury Rd, Brooklyn

$479,000
3 Beds 2 Baths 24192712 MLS
Welcome to 26 Old Putnam Road Extension, Plainfield-an impeccably maintained raised ranch offering nearly 2,000 square feet of finished living space in a quiet, convenient location. The bright, open-concept main level features a soaring vaulted ceiling, hardwood flooring, and abundant natural light. The updated kitchen boasts brand-new quartz countertops, newer appliances, and flows seamlessly into the dining and living areas, with easy access to the rear deck for entertaining. The flexible floor plan includes a spacious primary bedroom with a walk-in closet, Jack-and-Jill full bath and two additional main-level bedrooms, one of which is currently being used as a laundry room. A second laundry hookup is available on the lower level, making it easy to convert the space back into a bedroom if desired. The fully finished walkout lower level expands the living space with a family/media room, a potential fourth bedroom, a dedicated home office, and a second full bathroom. Additional highlights include an oversized attached garage, central air, efficient propane forced-air heat, and a brand-new propane tankless water heater. Outside, enjoy a beautifully landscaped yard with established perennial gardens, stone walls, and an expansive paved driveway. Conveniently located near shopping, restaurants, and major commuting routes, this move-in-ready home offers the perfect blend of comfort, flexibility and convenience.

26 Old Putnam Rd Extension, Plainfield

$479,999
24187613 MLS
An exceptional opportunity to own both a successful, established sports bar and the commercial real estate it operates from. This fully equipped, turn-key business is ready for its next owner and offers everything needed to hit the ground running. The spacious commercial kitchen is designed for high-volume service and features a fire suppression system, grill, oven, fryers, walk-in cooler, abundant prep space, and ample storage. The inviting layout includes a large bar, dedicated entertainment stage, multiple pool tables, and plenty of seating, creating the perfect atmosphere for live entertainment, leagues, and special events. Located in a highly visible, high-traffic location with excellent accessibility and abundant on-site parking, this property has built a loyal customer following and offers outstanding exposure. Commercially zoned, this property presents endless possibilities beyond its current use. Whether you're an experienced restaurateur, investor, or entrepreneur with a vision, the potential here is exceptional. Highlights include: Brand New Roof (April 2026),Turn-key business and real estate included, Fully equipped commercial kitchen,Fire suppression system, Walk-in cooler, Large bar and entertainment stage,Multiple pool tables and spacious dining areas, Ample storage throughout High-traffic location with excellent visibility, Plenty of on-site parking, Commercial zoning with numerous investment opportunities Don't miss this rare opportunity!!

1019 Norwich Rd, Plainfield

$500,000
3 Beds 2 Baths 24178930 MLS
Custom passive solar Contemporary set on 5+ private acres surrounded by natural beauty and peaceful scenery. A 5-year-young sunroom with tile flooring offers flexible space for relaxing, gardening, or enjoying year-round views of the landscape. Step outside to the spacious deck, ideal for outdoor dining or quiet mornings overlooking the tranquil setting. The inviting living room features a newer pellet stove and tile flooring designed for comfort and easy maintenance. Country dining room with wide plank floors, exposed reclaimed wood beams, and newer Andersen slider leading to the deck. Bright kitchen includes 3 skylights, porcelain farmhouse sink, solid wood cabinetry, stainless steel appliances, tile floor, and walk-in pantry. Convenient laundry/mudroom connects the kitchen to the attached 2-car garage. First Floor Primary Bed with new carpet, ceiling fan, slider to the deck to listen to the cute garden pond with water fountain. The second floor offers 2 additional bedrooms with exposed wood beams, a partially finished recreation room, and full bath with shower stall. The upper level sunroom includes a propane stove for supplemental heat. Energy-efficient design with strong insulation and berm construction helps maintain comfortable temperatures year-round. Additional updates include newer roof, water heater, washer and dryer, and new well water line. Convenient location close to shopping, dining, and commuter routes. Approx. 25 minutes to UCONN and 40 minutes to Hartford.

30 Grant Hill Rd, Brooklyn

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