Thompson Homes under $500,000

Welcome to Thompson, Connecticut—a hidden gem nestled in the picturesque Windham County. Known for its serene landscapes and tight-knit community, Thompson offers a perfect blend of rural charm and modern conveniences. With its rich history, scenic parks, and vibrant local culture, this town is an ideal place for families, retirees, and anyone looking to escape the hustle and bustle of city life.

Thompson is characterized by its beautiful countryside, featuring lush greenery, tranquil lakes, and an abundance of outdoor activities. Residents enjoy exploring the scenic trails of the Bigelow Hollow State Park or soaking in the beauty of the Quaddick State Forest. The town is also home to several local shops, delightful eateries, and community events that foster a warm and welcoming atmosphere.

For those looking to make Thompson their home, there are fantastic opportunities to find properties under $500,000. This budget-friendly market offers a variety of charming homes, from cozy single-family residences to spacious multi-level houses, all set against the backdrop of Thompson’s stunning natural beauty. Whether you’re a first-time homebuyer or seeking a peaceful retreat, you’ll discover that Thompson has something for everyone.

With its affordable housing options, vibrant community spirit, and stunning surroundings, Thompson, CT, is not just a place to live—it's a place to thrive. Come explore the beauty of Thompson, where your dream home awaits!

Newest Thompson Homes under $500,000

$349,999

9 Beds ⋅ 4 Baths ⋅ 24210190 MLS

HISTORIC CHARM MEETS VALUE ADD POTENTIAL in Connecticut's Quiet Corner! This distinctive multi family property offers 3 residential units plus a fourth space with commercial potential, and a fascinating history as Kenney's Store, a post office and train depot. Units 1, 2 and 3 feature spacious layouts, beautiful hardwood floors and timeless character. Two units offer 3 bedrooms, while the third offers 2 bedrooms. Unit 1 is currently configured as a 1-bedroom but can be converted back to a 2 or 3 bedroom layout. The property is ready to be repositioned, with one or two residential units requiring significant renovation and the former commercial space offering a true blank canvas for its next use. The commercial space includes two large rooms and a half bath. For the investor, owner occupant or entrepreneur with vision, this is an opportunity to transform a historic property and unlock its potential. Conveniently located near Acme Pond, the Air Line North State Park Trail, local vineyards and breweries, antique shops and scenic country roads. Bring your vision and create the next chapter of this unique property! CASH BUYER ONLY

6 Old Rte 12, Thompson

$439,900

5 Beds ⋅ 2 Baths ⋅ 24209915 MLS

Over 2,100 SF of beautifully updated living space awaits at 990 Riverside Drive! A welcoming farmer's porch adds to the curb appeal, while the home itself has been extensively renovated over the past approximately 10 years, including plumbing, electrical, HVAC with central air, insulation, kitchen, baths, flooring, paint and more. The spacious first floor offers a gorgeous kitchen with granite counters, abundant cabinetry, a new slider to the oversized deck and stairway leading to the upper level. An oversized dining room provides plenty of room for gatherings and entertaining, while the pellet stove offers an economical supplemental heat source. The enormous foyer offers incredible flexibility as an office, playroom, sitting area or additional living space as well as the second access to the upper level. A separate first-floor bedroom, office or flex room with access to the deck adds even more versatility. Upstairs are 4 generously sized bedrooms all completely updated. The second-floor bath is a standout with a whirlpool tub, double vanity, solid-surface counters, separate tiled shower, tile flooring and generous built-in storage. A walk-up attic and full basement provide excellent additional storage. Outside, enjoy the oversized deck, farmer's porch and detached 2-car garage. Conveniently located near the MA and RI borders with easy highway access, making commuting throughout the region a breeze. This is as turnkey as you are going to get with tons of space!!

990 Riverside Dr, 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

$465,000

4 Beds ⋅ 3 Baths ⋅ 24206701 MLS

A great place to call home...4 bedrooms, 3 baths, large, open eat-in kitchen with island and high ceilings, living room with skylights and high ceilings opening to a screened porch and deck. The primary suite is located on the main floor with sliders to the deck and an ensuite bath, along with 2 other bedrooms and a hall bath. Upstairs bedroom has an ensuite bathroom and storage area. The basement is really expansive with high ceilings just waiting for someone to finish it for additional living space, workshop, etc. Set on 2.43 acres, there is a very large, partially fenced yard with some lightly wooded area perfect for outdoor activities. Previously there had been an above-ground pool off of the deck and it would be very easy to add one in again. Conveniently located in the East Thompson area with a quick drive to Rt 395 and an easy drive to Boston, Worcester and Rhode Island Come and see how this home will work for you!

29 Lehtinen Rd, Thompson

$499,900

6 Beds ⋅ 3 Baths ⋅ 24206136 MLS

ONE of a KIND property close to the mass line! INVESTORS take notice! There are 3 single-family RANCH homes on this 1 ACRE property!! One is rented and the other 2 you can make your own rent and leases! 2 bedrooms each 2 of the homes are on a slab and the 3 rd one has a dirt basement. Mini splits, electric baseboard, and SOLAR! Built in 1953, 1968 and 1974.

1-5 Mountain Hill 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

$415,000

4 Beds ⋅ 1 Baths ⋅ 24196428 MLS

~*~ BRING YOUR CREATIVITY ~ TOOL BOX & LONG TERM VISION to 303 RIVERSIDE DRIVE!! ~*~ ... Although this Property Requires The "3 RRRs" Renovation, Repairs & Restoration .... It will be a Rewarding Opportunity for the Right Buyer!!!... Being Sold As-Is....This Cape Style House comes with 4 Sprawling Acres of Wooded Privacy! Not to Mention the "Aged" wide Stonewall Borders!... The House offers 1,652 Square Feet of Living Space across 2 Floors ~ 4 Very Good Sized Bedrooms - 2 on Each Level!.. This Classic Layout has a Wood Fireplace, Dining Area and Sun Room!.. Oil Heat, Private Well & Private Septic (Recently inspected showing a functioning system)... The Crown Jewel of this Property is the Two-Story Barn!!.. Need extra Storage? Need a Work Shop? Need a Fun Place for the Grandkids to hang out?... Endless Possibilities!!.. And there's More..... 1-Car Garage and a Separate Structure on the hill once used as a Kids Place House! .... The back part of the land borders the AIRLINE TRAIL !.. Highway Access is only Minutes to I-395! You will be close to Antique Shopping , Great Dining & Entertainment in the Surrounding Towns!!... Bring your Furry Friends to the West Thompson Dam ~ walking trails. You are also close to the Woodstock Orchards ~ Just in time for "Pick Your own Apples!!" ... Or Relax with an Adult Beverage at the Tree House Brewery and/or Taylor Brook Vineyard!... Don't miss this Opportunity !! :)

303 Riverside Dr, Thompson

$479,900

3 Beds ⋅ 2 Baths ⋅ 24203203 MLS

Built solid with the intention of lasting, this 1950's Cape style home has received a full renovation just 3 years ago. Home has a modern feel with still remaining the vintage charm. Set on a 1/2 acre of land, this 3 bedroom 2 bathroom home is move-in ready. Newly installed hardwood floors throughout, home features a modern kitchen-granite counters, newer cabinets, island, & stainless steel appliances. The open living room & dining area are just off the kitchen, with access to a first floor full bathroom along with a pantry & laundry room. An additional family room with gleaming hardwood floors along with a wood burning fireplace is a potential first floor primary bedroom (town has 4 bedrooms listed in records). Upstairs-three generous size bedrooms along with an additional full bathroom. Mechanically, you will enjoy efficient propane WAIR heat along with central heat, a newly installed whole house automatic generator, along with a professional basement waterproofing/French draining system to ensure a dry basement for storage or additional living space. A detached 2 car garage makes great vehicle, lawn equipment, workshop space. Home is located just minutes from the MA line for commuting/shopping.

25 Watson Rd, Thompson

$365,000

3 Beds ⋅ 1 Baths ⋅ 24203021 MLS

Welcome home to this 3 bedroom ranch, offering the perfect opportunity for first time home buyers, those looking to downsize, or anyone seeking easy one-level living. A spacious basement provides endless possibilities for storage, a workshop, home gym, or future finished living space. Enjoy peace of mind with a roof that is only 8 years old and an electric hot water heater that's just 9 months old. Connected to public water and public sewer, this home is ready for its next owners to make it their own. Conveniently located with easy access to local amenities, this property is full of potential.

2 Rachel Dr, Thompson

$359,900

3 Beds ⋅ 2 Baths ⋅ 24202370 MLS

Welcome home to this 1940's Cape Cod style home that has been completely remodeled from the studs in over the past 25 years of ownership. The flexible floor plan offers 3 bedrooms and 1.5 bathrooms, with an open eating-space kitchen featuring tiled floors, a comfortable living room with wood floors, and a first-floor bedroom currently being used as an office. The recently renovated full bathroom adds another modern touch. Upstairs, you'll find two additional bedrooms, including a primary suite with its own half bath, plus a fantastic walk-in attic space for storage or future possibilities. Outside, enjoy over half an acre of yard along with a large barn-style detached garage/shed with power-perfect for vehicles, toys, hobbies, or extra storage. Additional features include a newer septic system, updated 200-amp electrical service with generator-ready connections, full insulation, and a walk-out basement.

133 Church St, Thompson

$499,000

3 Beds ⋅ 2 Baths ⋅ 1420812 MLS

Set on a private, park-like .84-acre property in North Grosvenordale, 29 Vandall Street is a truly distinctive 1958 ranch offering approximately 5,700 square feet of finished living space across two levels, with 5,794 gross square feet per tax records. The home features 3 bedrooms, 2 full baths, generous living spaces, central air, two fireplaces, town sewer, and a 35-panel solar system. The centerpiece is an impressive indoor swimming pool, creating a year-round space for recreation, relaxation, and entertaining. The spacious primary suite includes a walk-in closet and an expansive bath finished with distinctive Vermont Verde Antique Serpentine stone, featuring double sinks, a bidet, jetted corner tub, and walk-in shower with bench and body jets. The finished lower level expands the home's versatility with a large game and recreation room, built-in bar, and fireplace surrounded by floor-to-ceiling stonework. Additional finished spaces provide room for hobbies, gatherings, storage, or flexible living needs. Adding to the property's unique character are a Cold War-era fallout shelter with original U.S. Civil Defense materials, hidden compartments, and other unexpected features throughout the home. With substantial indoor space, a private setting, and amenities rarely found under one roof, 29 Vandall Street offers a remarkable combination of character, history, and functionality.

29 Vandall Street, Thompson

$499,000

3 Beds ⋅ 2 Baths ⋅ 24200502 MLS

29 Vandall St, Thompson

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