Windham Homes with Cape Cod Style

Welcome to Windham County, Connecticut, a picturesque region that beautifully marries natural charm with vibrant community life. Nestled in the heart of New England, Windham County is renowned for its lush landscapes, historic towns, and a rich tapestry of culture and recreation. Whether you're hiking the scenic trails of the Natchaug State Forest or exploring the quaint shops and eateries in Willimantic, this county offers a delightful blend of outdoor adventure and small-town warmth.

One of the standout features of Windham County's real estate market is its enchanting Cape Cod-style homes. With their distinctive steep roofs, dormer windows, and inviting front porches, these homes exude timeless charm and character. Originally inspired by early colonial architecture, Cape Cod homes are designed to withstand the elements while providing a cozy and functional space for families. Inside, you’ll often find open floor plans, hardwood floors, and ample natural light, making them perfect for both entertaining and everyday living.

Living in a Cape Cod home in Windham County means embracing a lifestyle that celebrates both comfort and community. Imagine sipping your morning coffee on a sun-drenched porch, or hosting weekend gatherings in a beautifully landscaped yard. With a variety of styles and sizes available, there’s a Cape Cod home to suit every taste and budget.

Windham County is not just a place to live; it’s a community where memories are made, and dreams take root. Come explore the charm of Cape Cod-style homes and discover your perfect sanctuary in this enchanting corner of Connecticut!

Newest Windham Homes with Cape Cod Style

$309,900

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24201525 MLS

A delightful gem of a home, this Cape is set in the heart of Willimantic. This home offers easy access to town, shopping, and commuting routes. A charming, move-in-ready opportunity is updated and ready for its next owner, with an open-air plan and unique, tasteful finishing touches throughout. Fresh, modern updates within the last 4 years include: kitchen with granite counters and new stainless appliances (oven/range, microwave, range hood, refrigerator, dishwasher), first-floor bath, carpet in the upstairs bedrooms, newer vinyl siding, windows, roof, and furnace, 3-zone heat for comfort and efficiency. First-floor primary bedroom - easy single-level living, first-floor laundry in the expansive four-season sunroom, sunroom opens to a deck overlooking a very private backyard with stone walls, 3 bedrooms, 1 full bath, 6 rooms total, original wood panel interior doors; updated insulated exterior doors. Added features include, connected Bluetooth speaker in the shower, electric fireplace insert and, under-house 1-car garage plus private driveway (4 parking spaces) and Solar - schedule your tour today!

349 Mansfield Ave, Windham

$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

$589,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24201418 MLS

There's something special about being able to see the lake from home and be at the water in just a short walk. Welcome to 4 Oak Drive, a thoughtfully cared-for 2-bedroom, 2-full-bath home with a spacious loft in the Lake Bungee community. With deeded lake and beach rights and views of the water, this newer home sits on an inviting corner lot surrounded by colorful flowers, raised vegetable gardens and touches of classic New England charm. Traditional stone walls along the adjoining historic cemetery add to the peaceful character of the setting. Inside, the open-concept kitchen with granite countertops and center island flows comfortably into the dining and living areas, with windows bringing in plenty of natural light and views toward the lake. Step out onto the deck to unwind and enjoy the glowing sunsets that cast a warm light across the property. Both bedrooms are on the main level, including the primary with a large walk-in closet, private full bath and sliders to its own small deck. Upstairs, the open loft offers flexible additional space along with two closets and attic storage. The full walk-out basement with sliders provides plenty of storage and potential for future finished living space. Generator hookup ready for added peace of mind. Lovingly maintained and easy to settle into, this home offers a welcoming place to enjoy the seasons, the lake and the simple pleasures of home, all while being conveniently located near the Massachusetts line and area amenities.

4 Oak Dr, Woodstock

$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

$589,999

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24202965 MLS

Set on 5.19 mostly open and level acres just 1.5 miles from the center of Eastford, this 4-bedroom, 2-bath home offers space, privacy and an ideal setup for horses, hobby farming or simply enjoying country living. Approximately 1.5 acres are fenced with Ramm fencing and divided into large and small paddocks. The 3-stall barn includes a tack/feed room, storage for approximately 450 bales of hay and a lean-to for equipment. Outside you'll also find a raised-bed garden, established plantings, Kloter Farms shed, whole-house Generac generator, oversized driveway and 2-car garage. Major updates include a new roof in May 2026 and new Class A furnace chimney in June 2026. Inside, the impressive great room features hardwood floors, soaring 18' cathedral ceilings, gas fireplace and French doors to a composite deck. The kitchen offers granite counters, stainless appliances, island, eat-in area and access to a second large deck. Two bedrooms and a full bath complete the main level. Upstairs are two newly carpeted bedrooms and another full bath. The lower level provides two large basement rooms, laundry, water treatment system, Buderus boiler and abundant storage. Central A/C serves the main level, with portable units upstairs. Frontier Fiber ready. A wonderful opportunity for those seeking acreage, animals and room to spread out!

160 Westford Rd, Eastford

$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

$549,900

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24201270 MLS

There's something special about being the first to call a brand-new home your own! Set within a desirable Bunggee lake community in Woodstock Valley, this new construction Cape offers approximately 2,230 sq. ft. of finished living space across three levels with 3 bedrooms and 2.5 baths. The main level features an expansive wraparound kitchen, sliders leading to the back deck, and two separate living spaces that can easily adapt to your lifestyle. Create an eat-in kitchen with two living areas, a living room and den, or use one as a spacious formal dining room. A convenient half bath and laundry room complete the first floor. Upstairs are two generous bedrooms, a full bath, and a spacious primary suite with its own private bath and walk-in closet. The finished walkout lower level adds even more flexibility for a family room, home office, gym, hobbies, or additional recreation space and connects directly to the one-car under-house garage. Outside, the private backyard is surrounded by mature trees with a level, open area offering plenty of room for entertaining, gardening, play, or simply relaxing outdoors. The home is nearing its completion, giving you the opportunity to be its very first owner and enjoy all the benefits of new construction without starting from scratch. A great combination of space, privacy, flexibility, and lake-community living! Lake rights and fully recreational amenities offered by Bunggee Lake, including boating, fishing, and swimming opportunities.

61 Red Cedar Rd, Woodstock

$429,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24199786 MLS

Welcome to 55 Glebas Road, a charming Cape-style home offering comfortable living, desirable amenities, and plenty of space both inside and out. This inviting 3-bedroom home features an open and welcoming layout, 2.5 bathrooms, and a finished walk-out lower level providing additional living space and flexibility for a home office, recreation room, guests, or extended living. Enjoy the convenience of first-floor laundry and an attached two-car garage. Step outside to a private backyard retreat featuring a deck, patio, enclosed porch, and in-ground pool-perfect for relaxing, entertaining, and enjoying the warmer months. A fenced yard, storage shed, and paved driveway add convenience and functionality to this inviting property. Set in a peaceful Plainfield location, this home offers a great combination of privacy, space, and everyday convenience. With its versatile finished lower level, multiple outdoor living areas, and inviting pool area, 55 Glebas Road is ready to welcome its next owner! Sale dependent upon the contract owner's ability to take title

55 Glebas Rd, Plainfield

$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

$459,900

5 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24199139 MLS

This beautiful 1740 antique Cape sits on a lovely 1.59 acres with the iconic stone walls of the area. The home is immaculate and ready for you to move right in. The first floor features a kitchen with the pantry everyone wants. In addition there is an impeccable butler's pantry with custom storage and display cases. The dining room is bright and can accommodate large family gatherings. There is a working fireplace in the sitting room and the office receives beautiful afternoon light. The sunny living room boasts a wood stove to keep you warm all winter. There is a first floor full bath & laundry. The second floor has four bedrooms, a full bath, and a large walk in attic. Other features include a screened porch, two barns, which would be ideal for a hobby farm or workshops/studios. There is a fenced-in area for pets, an above ground pool, a large garden area with two raised beds, in ground beds, 4 newly planted fruit trees, and an area for expansion. Half of the property is in the process of rewilding, but it has only been a year and can easily be returned to lawn if desired. Recent updates include a new roof in 2025 with a warranty ,which will convey, many replacement windows, new chimney cap, the well pump was replaced two years ago, and the woodstove was installed in 2025. The home is filled with charm and character and has a floor plan that provides many options. Schedule a time to view this exceptional Brooklyn property

136 Hartford Rd, Brooklyn

$989,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24185445 MLS

There are properties, and then there are properties that invite you to imagine an entirely different way of living. Set in the heart of picturesque Pomfret, this extraordinary 51-acre estate offers a rare combination of land, history, architectural charter and limitless potential. For those who have envisioned an authentic country estate, the possibilities are extraordinary. Create a refined gentleman's-or gentlewoman's-farm, cultivate a private equestrian or agricultural retreat, surround yourself with beloved animals or simply enjoy the unparalleled freedom that comes with owning an expansive parcel of land.At the heart of the property is a beautifully restored Cape, offering charm and character. Nearby, a stately antique Colonial awaits a discerning owner with the vision to restore its historic grandeur. Complementing the residences are impressive barns,and outbuildings, creating an estate setting rarely found in today's market.For the collectors, craftsman, hobbyist or automobile enthusiasts the property's scale and collection of structures provide remarkable opportunities.For those seeking a more self-sufficient lifestyle, the acreage offers the canvas for a private homestead routed in the timeless traditions of country living while embracing today's ideals of sustainability and stewardship.Those who simply appreciate the finer things in life, there is another option:do nothing more than enjoy it.

236 Deerfield Rd, Pomfret

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