Windham County CT Homes for Sale

/4
$89,000
- Land
- 0.93 Acre
- $95,699 per Acre
0 Thompson Rd Unit Lot 3G, Thompson, CT 06277

Build your dream home in the peaceful town of Thompson, where privacy, space, and New England charm come together. This residential lot offers the perfect setting for a custom home surrounded by nature, while still providing convenient access to major routes, nearby towns, and everyday amenities. Thompson is known for its scenic landscapes, rural character, and strong sense of community-ideal for

The Schlesman Realty Group ERA Key Realty Services

0 Thompson Rd Unit Lot 3G, Thompson, CT 06277
/17
$95,000
- Land
- 3.86 Acres
- $24,611 per Acre
Lot 13A Somers Turnpike, Woodstock, CT 06281

Located in the heart of Woodstock on the scenic Somers Turnpike, this nearly 4-acre elevated lot offers you the perfect setting for your dream home. A long driveway will lead you to a secluded potential home site with stone walls, lush landscape and beautiful sunsets. There is a recent plot survey and a perc test (11/2025), which will be available upon request. The property has 113 feet of road

Brenda Chubbuck CR Premier Properties

Lot 13A Somers Turnpike, Woodstock, CT 06281
/20
$359,900
- 3 Beds
- 3 Baths
- 2,128 Sq Ft
91 Insalaco Dr, Windham, CT 06280

This beautiful colonial is situated on a private lot in a wonderful cup-de-sac neighborhood setting. A unique aspect of this home is that it has 2 primary bedroom suites with one being on the first floor allowing for handicap accessibility if needed. Both bedroom suites feature full bathrooms, walk-in closets, hardwood floors and tile in the baths. You will love the spacious first floor open

Mike Thompson Countryside Realty

91 Insalaco Dr, Windham, CT 06280
/27
$359,900
- 1 Bed
- 1.5 Baths
- 3,391 Sq Ft
239 Main St, Danielson, CT 06239

INVESTORS LOOK! One of a kind FABULOUS Mixed Use/ Residential Building with OFFICES, APARTMENTS and VISIBILITY for your Business right on Main Street! CITY WATER, SEWER and GAS! Building features a 1 Bedroom Apartment with private entrance, another PRIVATE office, as well as 3 offices with a shared sitting area and storage area and full bathroom. There is also an unfinished room upstairs that is

Christine Johnson RE/MAX One

239 Main St, Danielson, CT 06239
/40
$2,840,000
- 6 Beds
- 3.5 Baths
- 10,908 Sq Ft
5 Brookside Ln, Woodstock, CT 06281

Exceptional pride of ownership is evident in this rare opportunity to acquire a 14-unit multifamily asset in Woodstock, CT, with the option to combine with an additional 14 units at Pinecrest Apartments for portfolio sale. Built in 1987, the property features tenant-paid utilities with individual hot water heaters and electrical subpanels in every unit-supporting efficient operations and strong,

Lisa Cozzi Century 21 AllPoints Realty

5 Brookside Ln, Woodstock, CT 06281
/29
$4,320,000
- 9 Beds
- 8 Baths
- 14,103 Sq Ft
23 Pine Crest Ridge, Woodstock, CT 06281

Pinecrest Apartments is a meticulously maintained 14-unit residential community situated on 5.5 acres in Woodstock, CT, reflecting clear pride of ownership, durable construction, and sustained tenant demand. Built in 1989, the property is 100% occupied and offers a highly desirable mix of 13 townhome-style units and one ranch-style residence. The unit mix includes: (2) 1BR/1BA, (9) 2BR/1.5BA, (1)

Lisa Cozzi Century 21 AllPoints Realty

23 Pine Crest Ridge, Woodstock, CT 06281
/24
$214,900
- 2 Beds
- 2 Baths
- 1,359 Sq Ft
261 Old Colony Rd, Eastford, CT 06242

Cape-style home built in 1767, offering 6 rooms, 2 bedrooms, and 2 full bathrooms across 1,359 square feet. Features include a full basement and a one-car detached garage. The house and detached garage both have a new roof. Built in 1767, the property offers original architectural features alongside functional living space on a rural lot. This property is eligible under the Freddie Mac First Look

Michael Calabro Coldwell Banker Calabro

261 Old Colony Rd, Eastford, CT 06242
/3
$719,900
- 3 Beds
- 2.5 Baths
- 2,534 Sq Ft
771 Brook Rd, Hampton, CT 06247

Beautiful new construction Colonial offering over 2,500 sq ft of thoughtfully designed living space in a peaceful country setting. This home features 9-foot ceilings, an applianced kitchen with granite countertops and center island, and an open layout ideal for both everyday living and entertaining. Offering 3 bedrooms, 2.5 baths, plus a second-floor bonus room perfect for a home office,

Cary Marcoux RE/MAX Bell Park Realty

771 Brook Rd, Hampton, CT 06247
/2
$719,900
- 3 Beds
- 2.5 Baths
- 2,534 Sq Ft
769 Brook Rd, Hampton, CT 06247

Stunning new construction Colonial set on over 2 private acres in a serene country location. This 2,500+ sq ft home offers 9-foot ceilings, a bright open floor plan, and a beautiful applianced kitchen with granite countertops and center island-perfect for entertaining. The home features 3 bedrooms, 2.5 baths, and a versatile second-floor bonus room ideal for a home office, gym, or additional

Cary Marcoux RE/MAX Bell Park Realty

769 Brook Rd, Hampton, CT 06247
/7
$420,000 New Construction
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
279 Gorman Rd, Brooklyn, CT 06234

To-be-built raised ranch located in "The Fields" in Brooklyn, CT offering approximately 1,248 of well-designed living space with a 2-car attached garage below. The main level features the living space with vaulted ceilings; an open-concept kitchen, living and dining layout which offers ample natural light, ideal for modern living and entertaining. The kitchen is appointed with shaker-style

Katie Spenard Kazantzis Real Estate, LLC

279 Gorman Rd, Brooklyn, CT 06234
/40
$330,000
- 4 Beds
- 2 Baths
- 1,294 Sq Ft
34 N Windham Rd, Windham, CT 06280

Charming 4-Bedroom Colonial on 1.76 Acres in Windham! Welcome to 34 N Windham Rd, a lovingly maintained 1930 colonial set on a spacious 1.76-acre parcel offering privacy, outdoor space, and classic New England character. This home features 4 bedrooms and 2 full baths across 1,294 sq ft of comfortable living space - perfect for families, first-time buyers, or anyone seeking room to grow. Step

Marco Epifani The Hive Real Estate LLC

34 N Windham Rd, Windham, CT 06280
/40
$650,000
- 3 Beds
- 2.5 Baths
- 2,316 Sq Ft
483 North Rd, Ashford, CT 06278

Exceptional Currier and Ives type setting in peaceful Ashford CT. This property has a Barn with three oversized stalls and pastures; property absolutely designed for horses. This home has been tenderly updated to maintain all that historic feeling of this 225-year-old home while having all of the modern conveniences needed for today's living. 1st floor has a large dining room with a fireplace and

Dan Keune Campbell-Keune Realty Inc

483 North Rd, Ashford, CT 06278
/40
$650,000 New Construction
- 3 Beds
- 2.5 Baths
- 2,040 Sq Ft
143 Goshen Rd, Plainfield, CT 06354

GORGEOUS BRAND NEW colonial that has it ALL w/2040sqft,2.5ac,3bedrm, 2.5 Baths, 2 Bay Garage ,privacy (sitting 400ft of the road), minutes away from MOOSUP POND for your summers of boating, fishing & enjoying the beach w/all the bells & whistles. Pull into your driveway to your eye catching gray color siding w/ white trim & stamped concrete walkway to your Beautiful full length FARMERS PORCH

Irene Adams Signature Properties of NewEng

143 Goshen Rd, Plainfield, CT 06354
/38
$729,900
- 3 Beds
- 2.5 Baths
- 2,400 Sq Ft
56 W View Dr, Woodstock, CT 06281

This stunning custom-built 2019 Colonial farmhouse blends modern design with efficient, thoughtful craftsmanship. Meticulously maintained, it features an inviting open-concept layout, hickory wood floors, and a gourmet chef's kitchen with an Electrolux 36" induction range, custom range hood, GE Profile stainless steel appliances, and a pantry. Natural light fills the spacious living and dining

Pamela Therrien The Neighborhood Realty Group

56 W View Dr, Woodstock, CT 06281
/7
$49,900
- Land
- 1.5 Acres
- $33,267 per Acre
0 Center Rd, Woodstock, CT 06281

Lovely 1.5 wooded acres with spring fed pond with over 200 feet of road frontage. Beautiful area of town. Property was perc'd at one time, but hasn't been done in years. Build your dream house in the Woodstock school district. Buyer and buyers agent to due their due diligence.

Diane White CR Premier Properties

0 Center Rd, Woodstock, CT 06281
/40
$528,000
- 3 Beds
- 3 Baths
- 1,700 Sq Ft
93 Lakeside Dr, Eastford, CT 06242

Welcome to the lake house you've been searching for. Enjoy year-round comfort in this beautifully maintained 3-bedroom home on the quiet shores of Ashford Lake. A high-efficiency propane furnace keeps you warm all winter, while mini-split systems provide cool, efficient comfort in the summer. The main-level living room features five new thermopane windows framing stunning, panoramic views of the

Honglian Wu Home Selling Team

93 Lakeside Dr, Eastford, CT 06242
/13
$299,900
- 3 Beds
- 2 Baths
- 1,680 Sq Ft
625 Pudding Hill Rd, Hampton, CT 06247

Nestled back on 2 PRIVATE ACRES sits a sprawling COUNTRY ranch w/ APPLIANCE kitchen w/ NEW white shaker cabinets and countertops open to LARGE dining room. SPACIOUS living room and 3 bedrooms w/ 2 full bathrooms. ALMOST 1700 sq ft! Outbuilding for storage (there is NO basement). This is a COUNTRY home and setting perfect for animals! CAMERAS on property do NOT drive down driveway.

Christine Johnson RE/MAX One

625 Pudding Hill Rd, Hampton, CT 06247
/33
$332,000
- 3 Beds
- 1 Bath
- 1,242 Sq Ft
40 Tarbox Rd, Plainfield, CT 06374

Welcome to this fully renovated 3 bedroom, 1 bath home that has been completely brought back to life! This house has been transformed from top to bottom. Notable exterior upgrades include new roof, new siding, new windows, and a new drilled well. Once you step inside this home you will notice a completely refreshed interior which provides a modern feel with fresh neutral paint to suit any decor

Joseph Rivers Larrow's Real Estate

40 Tarbox Rd, Plainfield, CT 06374
/40
$379,900
- 2 Beds
- 2 Baths
- 2,066 Sq Ft
127 Windy Hill Rd, Hampton, CT 06247

Circa 1820's Cape Cod style home conveniently located in Hampton. Sitting on over 2.5AC of great usable land, this 2-bedroom 2-bathroom home has been well maintained and updated over the years. This home received 1990's addition with full basement adding great additional living space. Additionally, a first floor "den" makes an easy 3rd bedroom. The living room with wood floor & exposed beams

Ryan LaJoie Johnston & Associates Real Estate, LLC

127 Windy Hill Rd, Hampton, CT 06247
/40
$370,000
- 5 Beds
- 3 Baths
- 2,700 Sq Ft
385 Putnam Pike, Dayville, CT 06241

Unique investment offering: two separate homes for the price of one - a charming cottage plus a two-family home - totaling roughly 2,700 SF. This property presents an ideal opportunity for investors, house-hackers, or anyone looking to build equity and generate cash flow. Both structures need some updating - perfect for someone looking to add value and maximize return. Whether you live in one

Marco Epifani The Hive Real Estate LLC

385 Putnam Pike, Dayville, CT 06241
/24
$435,000
- 3 Beds
- 2 Baths
- 1,832 Sq Ft
11 Stone House Dr, Plainfield, CT 06374

In the Highland Court subdivision off of High Street, you'll find this lovely Cape Cod (a one-owner home built in 2017). Gorgeous new homes are currently under construction in this limited cul-de-sac neighborhood. The home offers a flexible floorplan. On the upper level, you'll find 2 generously-sized bedrooms and a full bath. On the main level, you'll find a beautiful dining room adjacent to the

Joan Casey

RE/MAX Legends

(860) 850-2035

11 Stone House Dr, Plainfield, CT 06374
/24
$379,900
- 2 Beds
- 2 Baths
- 1,500 Sq Ft
123 Ashford Rd Unit 1, Eastford, CT 06242

BEAUTIFUL COUNTRY Stand Alone CONDO in a 8 LOT subdivision with WRAP AROUND farmers porch. OPEN FLOOR plan with TILED flooring throughout. CHERRY cabinets, STAINLESS appliances (conveying) and GRANITE counters open to SPACIOUS living room w/ LARGE bright windows. 1 st floor bedroom and full bathroom w/ GLASS shower, GRANITE vanity and washer & dryer area (conveying). HARDWOOD stairs lead to upper

Christine Johnson RE/MAX One

123 Ashford Rd Unit 1, Eastford, CT 06242
/36
$349,000
- 3 Beds
- 1 Bath
- 1,423 Sq Ft
151 Brandy Hill Rd, Thompson, CT 06277

Antique-style farmhouse with over one acre of open land for gardening or your new inground pool! Home has 3 bedrooms and one bath. Large front-to-back living room with sliders out to a wrap-around deck. Kitchen with stove, refrigerator, dishwasher and washer/dryer hookups. Two large bedrooms on the second floor with ample hallway space to serve as a small den. Third bedroom on the first floor.

Joann Hall RE/MAX Bell Park Realty

151 Brandy Hill Rd, Thompson, CT 06277
/3
$44,000
- Land
- 0.43 Acre
- $102,326 per Acre
0 Echo Dr, Windham, CT 06226

Nestled in a quiet, rural setting, this parcel offers an excellent opportunity to build your dream home, weekend retreat, or long-term investment. The property provides a generous amount of open space surrounded by natural scenery, offering privacy and a classic country feel while still being within convenient reach of local amenities, lakes, and major routes. Whether you're seeking a fresh start

Thomas Mele Dorrance Realty

0 Echo Dr, Windham, CT 06226
/5
$80,000
- Land
- 8 Acres
- $10,000 per Acre
147 Kelly Rd, Dayville, CT 06241

Welcome to the site of your future home! This 8 acre parcel offers privacy and a small stream that runs through the front portion of the land. Those with a vision will have an easy time creating a homesite that provides the ideal country setting. Offering over 200 feet of frontage this parcel of land has a ton of potential for anyone who is looking for a larger lot to build on!

Brendan Meehan RE/MAX Bell Park Realty

147 Kelly Rd, Dayville, CT 06241
/15
$215,000
- 2 Beds
- 1.5 Baths
- 1,344 Sq Ft
74 Athol St, Danielson, CT 06239

Welcome to Townhouse Place! This well-maintained 2-bedroom, 1.5-bath townhouse offers comfortable living in a highly convenient location. Situated at the back of the complex, this unit provides added privacy and a serene setting-step out through your sliders and enjoy a beautiful open yard right outside your door. Inside, the home features an open-concept main level perfect for modern living and

Kevin Brignole Spaulding Realty Group, LLC

74 Athol St, Danielson, CT 06239
/4
$85,000
- Land
- 3.36 Acres
- $25,298 per Acre
0 Brook Rd Unit lot 4, Hampton, CT 06247

Discover the perfect spot to build your dream home in the heart of quiet, picturesque Hampton. Surrounded by mature trees and classic New England Scenery, this 3.5 acre lot offers a serene, wooded setting with plenty of privacy. Approved building lot for septic and well. Owner of property is Ct Realtor

Lisa Labadia Houlihan Lawrence WD

0 Brook Rd Unit lot 4, Hampton, CT 06247
/13
$475,000
- 3 Beds
- 3 Baths
- 2,777 Sq Ft
10 Center St, Danielson, CT 06239

Located in the heart of a thriving downtown, this income earner is mixed use with endless possibilities! 2 commercial units street level great for office or retail and 3 residential, second floor rented units. 4 units have been recently renovated. LVP flooring throughout units and stairway. Private entry for residential tenants and commercial units have their own separate entries. On street

Amy Brunet Brunet and Company Real Estate

10 Center St, Danielson, CT 06239
/2
$400,000
- Land
- 11.8 Acres
- $33,898 per Acre
131 Church St, Sterling, CT 06377

11.80 of sand, gravel and rock. Current owner has permits in place. 1300 ft of road frontage. Lots of possibilities. Seller will be removing large boulders.

Cary Marcoux RE/MAX Bell Park Realty

131 Church St, Sterling, CT 06377
/40
$449,000 New Construction
- 3 Beds
- 2 Baths
- 1,696 Sq Ft
6 Prospect St, Putnam, CT 06260

Welcome to this stunning NEW BUILD, offering modern comfort with a warm and inviting feel. The kitchen features beautiful quartz countertops and a wood-tone island with a waterfall quartz finish that adds both style and warmth to the space. Enjoy brand-new appliances, new flooring throughout, and an ample-sized garage with a concrete driveway. A spacious deck provides the perfect spot to relax or

Tanya McDermott Berkshire Hathaway NE Prop.

6 Prospect St, Putnam, CT 06260
/31
$399,000 Open Sun 1PM - 3PM
- 4 Beds
- 2 Baths
- 2,104 Sq Ft
63 Glebas Rd, Plainfield, CT 06374

Welcome to 63 Glebas Rd! The killer views from this home are hard to beat! This fantastic raised ranch located in a quiet walkable neighborhood at the top of the Black Hill, is surrounded by fields and farms. Offering true country charm, this 4-bedroom, 2 bath home with a mostly finished walkout basement is ready for you to enjoy. The private fenced in back yard includes a large above ground

Lorraine Bandoni CrossRoads Real Estate Group

63 Glebas Rd, Plainfield, CT 06374
/11
$135,000
- 1 Bed
- 1 Bath
- 718 Sq Ft
49 Canterbury Rd Unit K, Plainfield, CT 06374

Welcome to Cornerstone Place Condos at 49 Canterbury Road in Plainfield, CT! This well-maintained unit offers comfort and convenience throughout. The home includes newer carpeting, a newer washer and dryer, and a newer water heater for added peace of mind. Enjoy a quiet, well-kept neighborhood setting with a large walk-in closet in the bedroom and two generous closets in the living room. A

Kaylyn Pusczynski Century 21 AllPoints Realty

49 Canterbury Rd Unit K, Plainfield, CT 06374
/2
$750,000
- Land
- 16.9 Acres
- $44,379 per Acre
0 Wauregan Rd NE Unit 24143170, Plainfield, CT 06374

Commercial land located at the Wauregan four corners. Prime spot for development. The 16.9 acres is a combination of 8 lots. Some lots may be able to sell individually. Dollar General is located across the way. Located near the old C & M Corporation and in the area of other Commercial Industrial Buildings.

Cary Marcoux RE/MAX Bell Park Realty

0 Wauregan Rd NE Unit 24143170, Plainfield, CT 06374
/35
$445,000
- 5 Beds
- 3.5 Baths
- 3,719 Sq Ft
16 Wilkinson St, Putnam, CT 06260

Opportunity is back on the market!A compelling investment opportunity in the center of Putnam, this 1867 Victorian style home combines historic appeal with practical updates and multiple paths for added value. Used today as a two-family, the property offers spacious floor plans, high ceilings, and a layout that lends itself to strong rental demand or a comfortable owner-occupied arrangement.

Kristen Kaskela Berkshire Hathaway NE Prop.

16 Wilkinson St, Putnam, CT 06260
/31
$299,000
- 3 Beds
- 2 Baths
- 1,401 Sq Ft
162 Scotland Rd, Windham, CT 06280

2.5 Acres with a beautiful updated 3 bed, 2 bath. Full mechanical upgrade including new well to be made prior to closing! 1400 sqft home with a detached garage and a barn with electric hookups that also sit on the property! Discover the charm and potential of this Windham property, offering a spacious layout and a peaceful setting in a desirable location. Perfect for buyers seeking comfort,

Dillon Cass eRealty Advisors, Inc.

162 Scotland Rd, Windham, CT 06280
/4
$60,000
- Land
- 0.61 Acre
- $98,361 per Acre
81 Deerfield Dr, Sterling, CT 06377

Discover this beautiful 0.61-acre lot-ready and waiting for your dream build. Tucked away on a private road in Sterling, CT, this property offers the perfect opportunity to create your own peaceful retreat. Whether you're envisioning a custom home or a quiet getaway, this slice of heaven provides the privacy and space you've been looking for.

Kristopher Tramont Real Broker CT, LLC

81 Deerfield Dr, Sterling, CT 06377
/36
$499,000
- 3 Beds
- 1.5 Baths
- 2,003 Sq Ft
1436 North Rd, Dayville, CT 06241

Welcome to this charming 3-bedroom, 2-bath ranch located in a desired area on North Road. This classic 1966 brick home offers timeless character with a cozy fireplace and inviting layout. Enjoy newer flooring throughout the main living area and fresh carpeting in the bedrooms for a move-in ready feel. The main bathroom renovation has been started, offering a blank canvas for you to customize to

Scott Pempek Berkshire Hathaway NE Prop.

1436 North Rd, Dayville, CT 06241
/25
$299,900
- Land
- 1.07 Acres
- $280,280 per Acre
71 Deerfield Dr, Sterling, CT 06377

Discover the potential of this 1.07 acre lot. The property currently features a barn structure, but the true value lies in the land itself, being located on a private - no outlet road! With ample space to develop to dream property. Explore the possibilities this well-situated property has to offer. Trailer on property does not convey.

Kristopher Tramont Real Broker CT, LLC

71 Deerfield Dr, Sterling, CT 06377
/31
$975,000
- 2 Beds
- 2 Baths
- 2,895 Sq Ft
564 Hubbard Rd, Danielson, CT 06239

The escape begins the moment you turn onto the perfectly etched country drive ,where a winding dirt road leads through the meadow revealing a distinctive 3 BR 2 Bath 2800 sqft + contemporary home remodeled to blend rustic charm & comfort. Steps away you will find a perfectly situated 4 bay car garage with office loft. The setting feels like a private retreat, with multiple decks, each season

C. Tina Pappalardo Coldwell Banker Realty

564 Hubbard Rd, Danielson, CT 06239
/7
$139,900
- Land
- 16.11 Acres
- $8,684 per Acre
Lot 12-1 Tripp Hollow Rd, Brooklyn, CT 06234

Private, secluded 16+ Acre lot to be built with a custom build package in Brooklyn CT! Discover the ultimate sanctuary on over 16 acres of seclusion in picturesque Brooklyn. This remarkable lot is offered and to be sold only with a custom home-building package from Square 1 Building Assoc, tailored precisely to your vision. Bring your own architectural plans or choose from our thoughtfully

Jared Meehan RE/MAX Bell Park Realty

Lot 12-1 Tripp Hollow Rd, Brooklyn, CT 06234

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