Thompson Real Estate

Welcome to Thompson, Connecticut—a hidden gem nestled in the heart of Windham County. This charming town, known for its picturesque landscapes and rich history, offers a unique blend of rural tranquility and modern convenience, making it an ideal place to call home.

Thompson is characterized by its serene atmosphere, with lush greenery, rolling hills, and scenic lakes that invite outdoor enthusiasts to explore. The town is dotted with beautiful parks and nature trails, perfect for hiking, biking, or simply enjoying a leisurely stroll. Thompson's commitment to preserving its natural beauty makes it a haven for those who appreciate the great outdoors.

In addition to its stunning landscapes, Thompson boasts a vibrant community spirit. The town hosts various events throughout the year, including farmers' markets, craft fairs, and seasonal celebrations that bring residents together. With a strong sense of camaraderie, Thompson fosters a welcoming environment for families, retirees, and young professionals alike.

Education is a priority here, with access to quality schools that prioritize student growth and community involvement. Thompson's location also offers convenient access to nearby towns and cities, providing residents with an array of shopping, dining, and entertainment options.

Whether you're looking for a peaceful retreat or a place to plant roots, Thompson, CT, offers a delightful blend of nature, community, and opportunity. Explore the charming neighborhoods and discover why so many are proud to call Thompson home. Embrace the tranquility and vibrant community spirit that await you in this beautiful corner of Windham County!

Newest Listings in Thompson

$399,000

6 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24206557 MLS

Unlock the potential of 5.18 acres in Thompson! With substantial acreage and an existing residence already in place, 150 Wilsonville Road presents an exciting opportunity for investors, developers, or buyers looking to create something of their own. The land may offer potential for subdivision or additional development, subject to town approvals, zoning requirements, and buyer due diligence. The property features a character-filled 1800s farmhouse with a later addition, offering a spacious layout, hardwood flooring, built-ins, a large kitchen, first-floor laundry, and a distinctive two-story brick fireplace/chimney. The home is ready for renovation and provides an opportunity to restore, redesign, and add value while preserving some of its original character. Three storage structures located to the right of the home provide additional utility. Solar panels are present; ownership and terms are being verified. Conveniently located just minutes from I-395. A unique opportunity to combine acreage, an existing home, and potential future possibilities all in one property. Buyer and buyer's agent to perform due diligence regarding subdivision/development potential, property condition, solar, utilities, zoning, and permitting requirements. Sale contingent upon contract owners ability to take title.

150 Wilsonville Rd, Thompson

$899,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204987 MLS

A truly extraordinary property, 332 Ravenelle Road offers space, quality, privacy and versatility that are nearly impossible to find! Set on 13.5 gorgeous acres, this expansive ranch was built and occupied by its contractor/builder with exceptional attention to quality throughout. Designed for easy one-floor living, the home features 9-foot ceilings and a spectacular open floor plan anchored by a chef's kitchen and enormous family room-perfect for everyday living and entertaining. The massive 3-car garage boasts impressive 13-foot ceilings, while the 9-foot-ceiling basement runs virtually the full footprint of the home and previously housed the builder's extensive workshop-ideal for a contractor, car enthusiast, hobbyist or home-based business. Outside is your own private retreat with an above-ground pool, fenced area for animals, shed, abundant wildlife and beautiful seasonal views. Approximately 100 acres of landlocked private property and hundreds of acres of conservation land beyond create remarkable surrounding privacy and make this setting especially appealing to hunters and outdoor enthusiasts. Just across the street, West Thompson Lake offers fishing, boating and a public boat launch. A rare combination of exceptional craftsmanship, one-floor living, serious workspace and an incredible country lifestyle!

332 Ravenelle Rd, Thompson

$500,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

ACTIVE Status ⋅ 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

$365,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

$584,900

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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

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