Thompson Homes with Cape Cod Style

Welcome to Thompson, Connecticut – a hidden gem nestled in Windham County that perfectly blends the charm of rural living with modern conveniences. Known for its picturesque landscapes, Thompson is a haven for those who appreciate the beauty of nature, featuring lush forests, serene lakes, and scenic walking trails. With a friendly community and a rich history, this quaint town offers a peaceful retreat while still being conveniently located near major highways for easy access to surrounding areas.

One of the standout features of Thompson's real estate market is its stunning collection of Cape Cod-style homes. These iconic residences, characterized by their steep roofs, symmetrical facades, and charming dormer windows, embody a timeless elegance that appeals to many buyers. Inside, you'll find cozy interiors filled with warmth, often featuring hardwood floors, inviting fireplaces, and open layouts that are perfect for family gatherings or entertaining friends.

Living in a Cape Cod home in Thompson means embracing a lifestyle that values both comfort and style. Imagine sipping your morning coffee on a sun-drenched porch, surrounded by the tranquility of nature, or hosting summer barbecues in your spacious backyard. The community spirit here is palpable, with local events and farmers' markets that foster connections among neighbors.

Whether you're a first-time homebuyer or looking to settle down in a peaceful environment, Thompson's Cape Cod homes offer an ideal blend of character, charm, and community. Explore the possibilities of making this enchanting town your new home, where every day feels like a vacation in your own backyard.

Newest Thompson Homes with Cape Cod Style

$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

$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

$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

$579,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24199517 MLS

Custom-built Cape with an Accessory Dwelling Unit (ADU) on 1.62 acres just minutes from Thompson Speedway Motorsports Park, home to a racing track and the Raceway Golf Club, with easy access to 395. This one-of-a-kind property is a true car enthusiast's dream, anchored by a massive eight-car barn garage, ideal for collectors and hobbyists alike. The 1,552 square foot main house offers two bedrooms, hardwood and native pine floors throughout, a custom maple staircase, and French doors leading to an English garden. The kitchen features cherry cabinets and granite countertops, and the dining room includes a fireplace. Upstairs, the primary bedroom opens to a private deck overlooking the backyard. A partially finished basement adds flexible living space, Mitsubishi mini-split heating and cooling keeps every room comfortable, and a whole-house generator offers year-round peace of mind. A two-car garage with a ramp provides convenient access into the home. The property also includes a fully separate 576 square foot accessory dwelling unit with two bedrooms, one bath, a full kitchen, an additional downstairs room, and its own laundry and private garage, perfect as a guest house, home office, in-law, or rental. Set in a peaceful country setting in Connecticut's Quiet Corner, this property offers space, versatility, and craftsmanship rarely found together. Subject to Seller securing suitable housing, Seller has next home under contract.

22 Kingsbury Rd, Thompson

$694,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24197370 MLS

Attention log home lovers, hunters, car enthusiasts & more! Amazing opportunity to own this private, Log sided home, sitting on over 9.25 Acres of wooded land abutting 250+ acres of Windham Land Trust protected land. This young home was built just in 2004 and is over 2,000+ sq. ft. with an additional 300 sq. ft. rec room in the walk-out basement area. Imagine watching wildlife year-round on the wrap around farmers porch. Entering on the main level, the vaulted ceiling living room has a stone wood burning fireplace along with oak floors. The open concept kitchen & eating space area has plenty of working counterspace for entertaining. There are two good sized bedrooms on the main level along with a full bathroom & laundry for convenience. The second floor features a primary suite, walk-in closet, along with a full bathroom w/jetted tub & shower stall. Theres even a catwalk to a bonus loft area which would be a readers dream or a perfect home office! The inground pool with brand new fence is ready to enjoy. A detached 10+ car garage has 3 overhead doors, extra deep for tandem storage, metal roof, 2 post car lift, 100amp electric, along with a full loft, designed for vehicle storage, with additional garage door has tons of potential! Would make an excellent ADU for family. Flat driveway, Underground utilities, large-paved driveway pad, & Buderus boiler. Walking distance to Quaddick State Park. Minutes from MA & RI. Schedule your showing today!

751 Quaddick Town Farm Rd, Thompson

Start Your Search

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.