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. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in the Windham County, CT real estate market? Sign up for a  Windham County, CT Real Estate Market Report to see what’s active, under contract, and sold!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

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

$459,900
3 Beds 2 Baths 24194359 MLS
Welcome to this charming Cape Cod-style home located in desirable Huntington Estates. Nestled on 1.4 private acres and surrounded by mature trees and established gardens, this property offers a peaceful setting with beautiful views of the distant hillside. A long private driveway leads to the attached two-car garage and two additional outbuildings, providing plenty of space for vehicles, equipment, hobbies, and storage. The backyard is designed for relaxing and entertaining, featuring a massive deck connected to an above-ground pool-the perfect place to enjoy summer days, host gatherings, or take in the surrounding scenery. Inside, the open living room and kitchen area create a comfortable and inviting layout. The living room features beautiful hardwood floors and a striking stone-faced gas fireplace, adding warmth and character to the space. Sliding glass doors provide direct access to the expansive deck while filling the home with natural light. The kitchen and bathrooms feature durable tile flooring, while the generous room sizes and abundance of closets ensure that storage is never lacking. All three bedrooms are located on the second floor, while the basement offers two additional finished rooms that can be used as a home office, playroom, guest space, workout room, or hobby area. Above the garage is a large unfinished space currently used for storage. With some vision, this area could potentially be transformed into an office, fitness room, reading retreat,

11 Huntington Dr, Plainfield

$475,000
2 Beds 1 Baths 24193808 MLS
Wake up to beautiful lake views and enjoy year-round waterfront living in this charming single-family home on scenic Quaddick Lake.Whether you love fishing, swimming, or boating, Quaddick Lake offers it all, with access for all types of recreational boats.This inviting home features nearly 1,200 sqft of comfortable living space,including 2 bedrooms and 1 full bath.The spacious fireplaced living room creates a warm and welcoming atmosphere, while the formal dining room is perfect for family meals or entertaining guests. Convenient first-floor laundry and hardwood floors add to the home's comfort and character. One of the highlights is the heated sunporch overlooking the lake, providing a relaxing space to enjoy the view in every season. Central A/C keeps you cool in the warm weather and a Generator will be sure you have power during any storm outage.Step outside to the side deck, ideal for grilling, outdoor dining, or simply taking in the peaceful waterfront setting.Car enthusiasts, hobbyists, and those needing extra storage will appreciate the detached two-bay garage, along with an additional garage in the basement.The basement also includes a workbench and built-in storage shelving, making it an excellent workspace or storage area.Whether you're looking for a year-round residence, a weekend retreat, or a vacation home, this waterfront gem offers the perfect combination of comfort, recreation, and picturesque lakefront living.Don't miss this rare opportunity to own lakefront!

420 Brandy Hill Rd, Thompson

$489,000
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

$499,900
2 Beds 3 Baths 24189915 MLS
This beautifully crafted post-and-beam Saltbox home blends timeless character with modern functionality. 6.51 level acres! Designed with sustainability in mind, the home features solar power, well water, and an oil and wood burning furnace. With beautiful wide pine floors throughout, the open-concept living and dining area creates an inviting space for everyday living and entertaining, anchored by a cozy fireplace with wood stove perfect for winter evenings. The study on the main floor offers a quiet retreat with a convenient half bath that completes the first level. Upstairs, you'll find two comfortable bedrooms, each with its own fireplace, and a full bath, offering a peaceful and practical layout. The lower level offers a rec room, laundry room and full bath. This home features a large 24'x40' attached work shop ideal for a wood shop or art studio. Outside this property truly shines. Set back from the home is a 36'x24' barn suitable for 3 horse stalls or other animals, providing excellent flexibility for homesteading or equestrian use. This unique property offers space, craftsmanship, and versatility-perfect for those seeking a blend of rural charm, self-sufficiency, and thoughtful design. Located at the end of a quiet street, the property is bordered on three sides by a scout camp and is definitely a must see for those seeking privacy. Home could use some TLC but so much potential awaits! Possibly subdividable, buyer to do due diligence.

133 Fitts Rd, Ashford

$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

$495,000
3 Beds 2 Baths 24168086 MLS
Well-maintained 3-bedroom, 1.5-bath Cape that offers unique flexibility. For more than 75 years, this property was home to a family-run monument business, seamlessly blending residential living with a working space-an ideal setup for today's live/work lifestyle or those simply seeking extra room to fit their needs. Inside, you'll find a functional and inviting layout filled with character. The heated sun porch, formerly used as the business office, now serves as a bright and versatile space. The first-floor primary bedroom adds convenience and features a cedar closet. The home has seen several important updates, including a new hot water heater (2023), water holding tank (2024), oil tank, and septic tank. The roof is approximately 10 years old, and double-pane replacement windows help improve overall efficiency. Enjoy a Trex deck. Adding to the appeal, the abutting land is protected by Joshua's Trust, preserving the natural surroundings and offering lasting privacy. An exceptionally deep detached garage (roof 9 yrs) provides plenty of space for storage, hobbies, or workshop use. With zoning that allows for both residential and commercial use, this property presents a rare opportunity to create the lifestyle you want-whether that's purely residential or incorporating a home-based business. Conveniently situated on Route 6 close to shopping, restaurants, and everyday conveniences, this is a truly distinctive offering with history, flexibility, and potential

203 Willimantic Rd, Chaplin

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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.