Thompson Real Estate

Welcome to Thompson, Connecticut – a hidden gem nestled in the picturesque Windham County. Known for its serene landscapes and charming small-town vibe, Thompson offers a perfect blend of rural tranquility and modern convenience. With its rich history and vibrant community, it’s no wonder that this quaint town is becoming a sought-after destination for homebuyers looking for a peaceful retreat.

Thompson is characterized by its stunning natural beauty, featuring lush greenery, rolling hills, and sparkling lakes, making it an ideal spot for outdoor enthusiasts. Residents can enjoy a variety of recreational activities, from hiking and biking along scenic trails to fishing and kayaking on the pristine waters of Quaddick Lake. The town’s commitment to preserving its natural resources ensures that these stunning landscapes remain untouched for generations to come.

In addition to its natural allure, Thompson boasts a warm and welcoming community, where neighbors become friends and local businesses thrive. The town hosts numerous events throughout the year, fostering a sense of camaraderie among residents. From farmers' markets to seasonal festivals, there’s always something happening in Thompson.

Families will appreciate the town’s excellent school system and safe neighborhoods, making it a great place to raise children. With easy access to major highways, Thompson is conveniently located just a short drive away from larger cities, providing the perfect balance between rural living and urban accessibility.

Whether you're looking to settle down in a peaceful environment or seeking an investment opportunity, Thompson, CT, is a charming choice that promises a fulfilling lifestyle. Come explore all that this delightful town has to offer!

Newest Listings in 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

$874,000

5 Beds ⋅ 4 Baths ⋅ 24203344 MLS

EXCEPTIONAL EQUESTRIAN PROPERTY WITH 19 ACRES & TWO-FAMILY HOME! Set on 19 picturesque acres in Thompson, this unique property offers tremendous flexibility for residential and equestrian use. The two-family home provides options for 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

$489,900

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

$424,900

4 Beds ⋅ 2 Baths ⋅ 24203691 MLS

Nearly 1,700 SF ranch offering a hard-to-find 1-bedroom in-law setup, all conveniently located on the first floor! The in-law space features its own full kitchen/living area, full bath with laundry, bedroom & separate entrance, providing excellent options for extended household needs. The main living area offers a spacious layout with an updated kitchen featuring granite counters, refreshed bath & fresh paint! Numerous updates include the roof, electrical service & more, making this home truly turnkey. Step outside to an enormous rear deck overlooking the flat backyard, perfect for relaxing or entertaining. The lower level offers substantial additional space & excellent potential for future finishing. Ideally located just minutes from highway access, approximately 20 minutes to Worcester & about an hour to Boston, Providence, Hartford & Springfield. A versatile, updated home in an exceptionally convenient commuter location!

177 Sand Dam Rd, Thompson

$874,000

24203317 MLS

This is a thriving equestrian facility offering several barns, indoor riding arena, tractor/equipment barns on 19.1 acres with a multi family home.

91 Church St, Thompson

$380,000

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

$1,100,000

3 Beds ⋅ 3 Baths ⋅ 24202934 MLS

Lakefront luxury awaits on Little Pond in Thompson, CT. This brand-new 2,100sq. ft. custom build retreat offers effortless waterfront living with panoramic views throughout. Enjoy a brigh open-concept great room, a custom kitchen, and a main-floor primary suite with its own private sreened porch overlooking the water. Upstairs, you'll find two additional bedrooms and a full bath, perfect for family or guests. Downstairs, a walk-out basement with three shoreline sliders adds an optional 900 sq.ft. of flexible space for a home gym or rec. room.Step right outside to kayak, boat or fish year-round, all just minutes from I-395. Estimated Delivery Spring 2027.

25 Lakeview St, Thompson

$359,900

3 Beds ⋅ 2 Baths ⋅ 24202370 MLS

1940's Cape Cod style home that has been completely remodeled from the studs in over the past 25 years of ownership. Home features a flexible floor plan with 3 bedrooms and 1.5 bathrooms, a large & open eating space kitchen, first floor bedroom potential, along with over 1/2 AC of yard and a large Barn Yard detached Garage/Shed with power perfect for toys & vehicles. Newer septic updated 200-amp circuit breakers with generator ready connections & fully insulated. First floor features a tiled floor kitchen, wood floors in the living room along with the 1st floor bedroom currently utilized as an offer. The full bathroom was recently renovated & updated. Upstairs, 2 additional bedrooms along with a primary suite with 1/2 bathroom. Walk-in attic space is a great plus along with the walk-out basement.

133 Church St, Thompson

$599,900

3 Beds ⋅ 3 Baths ⋅ 24202365 MLS

One owner, meticulously maintained Ranch style home featuring almost 2,000 sq. ft. of 1 floor living, 3 bedrooms & 2.5 bathrooms situated on a cul-de-sac of just 3 homes. Sitting on 7.79 AC, plenty of room for exploring, expanding, along with animals with an existing 2 stall horse barn/shed & paddock. This home was designed with an attractive cape style roof and brick facade, setting this apart from any cookie-cutter design. Entering the front door to the living room you'll find 10 ft. ceilings, a fireplace with wood burning stove, Brazilian cheery hardwood floors along with an open floor plan to the dining & kitchen area. The tiled floor kitchen has plenty of working space for the cook, an island for additional prep & storage & Quartz counters. Just off the kitchen, and accessible from the 3-car garage (1 double deep/tandem), you will find a laundry room/mudroom along with 1/2 bath for convenience. The primary suite features a tray ceiling, walk-in closet, along with private bathroom: double sinks, claw foot tub, & tiled shower stall. Both other bedrooms are generous in size and are conveniently located across from the second full bathroom. A rear slider off the dining room leads to the private backyard. Home has very efficient Buderus hydro heat along with central air, all up to date on maintenance, along with underground power & is generator ready. 2x6 construction, added insulation, blown-in attic insulation, hot & cold water in the garage, paved driveway, & much more!

3 Jason Hts, Thompson

$584,900

4 Beds ⋅ 4 Baths ⋅ 24200678 MLS

Step into the Quiet Corner's storied past at this beautifully renovated 1814 Greek Revival and Italianate farmhouse, set on nearly an acre in the heart of the Thompson Hill Historic District, a 550-acre National Register district anchored by the town green. This 4-bedroom, 3.5-bath antique colonial blends original detail with modern comfort, including a grand entry staircase, two fireplace-warmed sitting rooms, a formal dining room, and an eat-in kitchen with stainless appliances that walks out to a private deck. A main-floor bedroom and half bath add flexibility. Upstairs, three bedrooms, two with private ensuites, and a bonus parlor. Outside, a spacious 30x40, two-story, three-bay barn with a workshop opens up real possibilities, from a car enthusiast, hobbyist, extra storage or even a home-based venture. Anyone interested in a B&B, event space, or short-term rental use should confirm zoning with the Town of Thompson. The location is a true draw: minutes from Lord Thompson Manor, a 1918 historic wedding estate, the William Mason House, and ANYA, an acclaimed fine dining destination that draws visitors from across New England. For those who want small-town history, architectural character, and a genuine sense of place, this is a rare opportunity.

369 Thompson Rd, 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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