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

15 Chaplin St, Chaplin
$469,900
3 Beds ⋅ 2 Baths ⋅ 24214543 MLS
-Step back in time and experience the timeless charm of this distinctive antique brick Colonial, set on approximately 3 acres of beautifully cultivated grounds. Blending historic character with thoughtful modern updates, this 3-bedroom, 2-full-bath home offers inviting living spaces, multiple fireplaces, and an exceptional chef's kitchen featuring an oversized island, stone countertops, new appliances, a large basin sink, and a convenient pantry. The kitchen overlooks the spectacular outdoor setting, where nearly 1,100 square feet of newly laid bluestone patio provides the perfect backdrop for entertaining, outdoor dining, or simply enjoying the surrounding gardens. The main level also features a bedroom, full bathroom, additional sitting room or formal dining room, and a grand living room rich with character. Upstairs, two generously sized bedrooms include a walk-in closet and dressing room, with an additional full bathroom completing the second floor. Modern comforts include Mitsubishi heating and cooling splits, a main-level pellet stove, and a high-end Biasi B10 Series boiler. The grounds are equally impressive, offering a thoughtfully established homestead with seven apple trees, three plum trees, two cherry trees, two peach trees, two fig trees, established hydrangeas, perennial flower gardens, specialty ornamental trees, and three large garden areas, all enhanced by beautiful stone walls. A partially unfinished rear section currently used for storage adds a

15 Chaplin St, Chaplin

1 Corttiss Rd, Thompson
$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

110 Church St, Putnam
$475,000
7 Beds ⋅ 3 Baths ⋅ 24206870 MLS
Step inside and you'll immediately understand what makes this home so unique. Beautiful wood floors, custom built-ins, intricate details, and four fireplaces with hand-carved mantels are reminders of an era when homes were built to be admired. Look up and you'll discover decorative ceiling medallions paired with gas-replica light fixtures that add warmth and authenticity to the home's historic character. The Albert C. Luke House, a captivating Queen Anne Victorian in the heart of Putnam where craftsmanship, character, and modern comfort come together beautifully. The updated kitchen blends old and new with quartz countertops and a marble backsplash while complementing the home's historic charm. The spacious first floor includes a welcoming foyer currently used as a sitting room, a library that could serve as a first-floor bedroom or office, and a full bath. A beautifully detailed staircase leads to four second-floor bedrooms, including one with a balcony and two with views of the Quinebaug River, plus a full bath with access from the hallway and primary bedroom. The third floor adds two more bedrooms and a full bath, offering incredible flexibility. Outside, enjoy established plantings, fruit trees, a greenhouse, and shed. The heating system and hot water heater are approximately five years old. Close to the river trail, downtown Putnam's restaurants, shops and entertainment, and minutes from I-395, this is more than a home, it's a piece of history ready for its next chapter

110 Church St, Putnam

1 Corttiss Rd, Thompson
$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

1019 Norwich Rd, Plainfield
$464,000
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

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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

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