169

Windham County CT Homes for Sale with Acreage

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  • /27

    $200,000

    • 2 Beds
    • 1 Bath
    • 1,902 Sq Ft

    701 Squaw Rock Rd, Moosup, CT 06354

    1790 home is possible tear down on 6.86 acres sold as is/ where is CASH ONLY! A couple of outbuildings sold as is/where is. What ever is left will convey inside and outside. Do your diligence at TOWN HALL for possible use. Abutting 36.7 acres goes with home. SOLD TOGETHER ONLY. CAMERAS on property DO NOT GO ON PROPERTY-APPOINTMENT ONLY. Bring a flashlight. 1/2 pond may be on this property.

    Christine Johnson RE/MAX One

    701 Squaw Rock Rd, Moosup, CT 06354
  • /30

    $499,900

    • 3 Beds
    • 1.5 Baths
    • 2,146 Sq Ft

    8 Juniper Ln, Moosup, CT 06354

    Welcome to this beautifully maintained Colonial / Contemporary home, set on a generous 1.38 acre private lot and located on a cul-de-sac road. The inviting first floor offers cathedral ceilings, a large, updated kitchen with stainless steel appliances, a breakfast bar, abundant cabinet and counter space which is perfect for cooking and entertaining. Also offers a spacious half bathroom and

    Paige Wojcik Berkshire Hathaway NE Prop.

    8 Juniper Ln, Moosup, CT 06354
  • /7

    $450,000

    • Land
    • 3.20 Acres
    • $140,625 per Acre

    0 Putnam Rd Unit 24117166, Plainfield, CT 06332

    Discover the potential of this prime piece of land at 0 Putnam Rd, Plainfield! This spacious residential lot offers endless possibilities, whether you're envisioning your dream home or exploring its potential as a commercial property. With a strategic location near major roadways and local amenities, this lot provides the perfect balance of convenience and opportunity. Positioned in a growing

    Phil Davis eXp Realty

    0 Putnam Rd Unit 24117166, Plainfield, CT 06332
  • /9

    $750,000

    • Land
    • 4.00 Acres
    • $187,500 per Acre

    0 Wauregan Rd NE Unit 24117158, Plainfield, CT 06374

    Unlock the potential of over 17 acres of prime commercial land at 0 Wauregan Road, strategically located in the growing town of Plainfield. Previously divided into smaller parcels, this expansive lot is now available as one large tract, offering incredible versatility for your business or development vision. Positioned near I-395 with excellent accessibility, this property is ideal for a wide

    Phil Davis eXp Realty

    0 Wauregan Rd NE Unit 24117158, Plainfield, CT 06374
  • /36

    $1,700,000

    • 7 Beds
    • 5 Baths
    • 4,283 Sq Ft

    90-94 & 93 Upton Rd, Ashford, CT 06278

    Welcome to one of the most extraordinary and locally adored estates in Eastern Connecticut-nearly 300 acres of rolling fields, woodlands, and historic charm offered as a single, unmatched property. Privately set along a quiet, town-maintained dirt road, this expansive estate combines 93 and 90-94 Upton Road into a rare opportunity for legacy ownership. The centerpiece is a breathtaking

    Nicole Gleason CR Premier Properties

    90-94 & 93 Upton Rd, Ashford, CT 06278
  • /12

    $474,995

    • 3 Beds
    • 2.5 Baths
    • 1,836 Sq Ft

    29 Meadowbrook Dr, Brooklyn, CT 06234

    Welcome to this charming two-story home that blends classic appeal with modern comforts. From the moment you arrive, the covered front porch and decorative window shutters invite you in with timeless curb appeal. Inside, the kitchen stands out with sleek quartz countertops and flows seamlessly into the main living spaces, all featuring rich hardwood flooring that adds warmth and character

    Steven Koleno Beycome of Connecticut

    29 Meadowbrook Dr, Brooklyn, CT 06234
  • /10

    $199,000

    • Land
    • 44 Acres
    • $4,545 per Acre

    571 Mashamoquet Rd, Pomfret Center, CT 06259

    This undeveloped parcel has a history of agricultural use and is currently designated as open space. Access is provided by a shared driveway, with a right-of-way (ROW) granted to one neighboring home. The driveway itself is owned by this property. Electricity would need to be extended from the nearby home that shares the driveway. The land is mostly high and dry, with a steep slope leading down

    Katie Spenard Kazantzis Real Estate, LLC

    571 Mashamoquet Rd, Pomfret Center, CT 06259
  • /9

    $149,900

    • 2 Beds
    • 1 Bath
    • 733 Sq Ft

    52 Park Dr, Chaplin, CT 06235

    Remodeled Mobile Home at the End of a Private Road on a Gorgeous 1.25 Acres! Private Level Lot with Two Bedrooms Plus Office!

    Antonio Incontro Countryside Realty

    52 Park Dr, Chaplin, CT 06235
  • /26

    $399,000

    • 3 Beds
    • 1.5 Baths
    • 1,528 Sq Ft

    68 Allen Hill Rd, Brooklyn, CT 06234

    This beautifully renovated home offers the perfect blend of modern upgrades and timeless charm. Step inside to find a brand-new kitchen featuring sleek granite countertops, stainless steel appliances, and custom cabinetry that provides both style and functionality. The warm glow of refinished hardwood floors flows throughout the main living areas, anchored by a stunning stone fireplace that adds

    Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

    68 Allen Hill Rd, Brooklyn, CT 06234
  • /15

    $385,000

    • 3 Beds
    • 1.5 Baths
    • 1,712 Sq Ft

    41 Jennings Ln, Windham, CT 06280

    Welcome to this beautifully maintained raised ranch nestled on a meticulously landscaped lot-offering exceptional curb appeal and plenty of space for outdoor entertaining. The oversized front, side, and backyard areas, along with the long, wide paved driveway and ample parking, provide the perfect setting for hosting family and friends. Inside, enjoy a bright and open floor plan featuring 3

    Sheri Shvonski List N Show LLC

    41 Jennings Ln, Windham, CT 06280
  • /40

    $500,000

    • 4 Beds
    • 3 Baths
    • 2,464 Sq Ft

    81 Lovers Ln, Plainfield, CT 06374

    You don't want to miss this home - where charm, comfort, and cherished memories await. Lovingly maintained by the same owners for over 30 years, this classic 4-bedroom, 3-bath Cape Cod offers over 2,400 square feet of warm, inviting living space across a beautifully designed layout. Enjoy the ease and comfort of a main floor primary bedroom, offering convenient single-level living while still

    Lisa Romano William Pitt Sotheby's Int'l

    81 Lovers Ln, Plainfield, CT 06374
  • /35

    $480,000

    • 3 Beds
    • 2.5 Baths
    • 2,144 Sq Ft

    8 Huntington Dr, Plainfield, CT 06374

    Welcome to 8 Huntington Drive, a beautifully maintained Colonial nestled in the trees in the desirable Huntington Estates neighborhood. This spacious 3-bedroom, 2.5-bath home offers over 2,200 square feet of living space with an open floor plan, hardwood floors throughout the main level, and a cozy fireplace in the family room. The kitchen features tile flooring and flows seamlessly into formal

    Christopher Scagliarini Signature Realty LLC

    8 Huntington Dr, Plainfield, CT 06374
  • /28

    $384,900 Open Sat 1PM - 4PM

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft

    184 Phoenixville Rd, Chaplin, CT 06235

    A unique blend of old-world charm and modern conveniences. Featuring 3 bedrooms and 2 baths, and 1,848 sqft sitting on 1.3 acres. Perfect for those looking for a piece of history with all the comforts of modern living. New windows, new garage roof, landscaping, a large garage and work shop with an above storage loft and parking for 6+. Also an outdoor shower and some beautiful river views steps

    Derek Greene Derek Greene

    184 Phoenixville Rd, Chaplin, CT 06235
  • /40

    $409,900

    • 4 Beds
    • 2 Baths
    • 1,068 Sq Ft

    686 Cook Hill Rd, Danielson, CT 06239

    Set on nearly 3 acres in a quiet Killingly location, this charming 4-bedroom, 2-bath mini-farm blends country character with modern upgrades. The home features a spacious layout, mini-split AC in the kitchen, a new well pressure tank (2024), wood stove in the bonus building, and added solar panels for energy efficiency. Outside, enjoy an expansive property ideal for equestrian use-including a

    Jonathan Bolano eXp Realty

    686 Cook Hill Rd, Danielson, CT 06239
  • /32

    $299,000

    • 2 Beds
    • 1 Bath
    • 1,040 Sq Ft

    242 Herrick Rd, Brooklyn, CT 06234

    1.93 acres of pure retreat await you! Follow the country roads to this charming 2-bedroom split-style home on an incredible lot. Private, yet accessible to all of the downtown conveniences you need. Lush fruit trees & bushes surround this outdoor oasis, with endless options for gardening! Double fire pits, gazebos of greenery - a must see. Many recent updates - priced to sell & ready for your

    Jackie Tacy RE/MAX One

    242 Herrick Rd, Brooklyn, CT 06234
  • /40

    $939,000

    • 3 Beds
    • 2.5 Baths
    • 3,282 Sq Ft

    133 Munyan Rd, Putnam, CT 06260

    Welcome to 133 Munyan Road in Putnam, Connecticut-a beautifully maintained and private retreat nestled on over 4 acres of picturesque land. This elegant 3-bedroom, 2.5-bathroom home, built in 1988, offers approximately 3,282 square feet of refined living space. Recent upgrades include a brand-new roof and an updated kitchen, blending modern comfort with timeless charm. Inside, you'll find a warm,

    Joel Grispino Drawbridge Realty

    133 Munyan Rd, Putnam, CT 06260
  • /37

    $399,900

    • 3 Beds
    • 2.5 Baths
    • 1,858 Sq Ft

    9 Main St, Hampton, CT 06247

    GORGEOUS field with a view with 6.7 ACRES to bring the horses and cows! OVERSIZED detached 2 car garage built in 2008 w/ LARGE LOFT above would make a great office. Gambrel awaits your finishing touches with trim, Moulding and paint. BEAUTIFUL eat in kitchen w/ GRANITE COUNTERS and breakfast bar w/ FRENCH doors leading to back yard and formal dining w/ FIREPLACE and wide plank flooring. LARGE

    Christine Johnson RE/MAX One

    9 Main St, Hampton, CT 06247
  • /4

    $125,000

    • Land
    • 2.00 Acres
    • $62,500 per Acre

    174 Mechanics St, Putnam, CT 06260

    2 Acres near downtown Putnam. Property has been perc tested. Bring your home plans and build your dream home. 2 Acres in an R-10 Zone is a rare find, check out this property today! You have options for water and sewer. There is city water at the corner of the property line. You have the option of connecting to the public water supply but do not have to, you can drill your own well. As far as

    Scott Pempek Berkshire Hathaway NE Prop.

    174 Mechanics St, Putnam, CT 06260
  • /30

    $335,000

    • 2 Beds
    • 2.5 Baths
    • 1,904 Sq Ft

    433 Norwich Rd, Plainfield, CT 06374

    Well maintained Colonial on 1.90 acres, enjoy nature with your private, fenced in back yard with plenty of room for the animals! Fireplaced living room, fresh carpet, updated kitchen with slider to back deck, huge upstairs master bedroom, large closets and a large, updated, upstairs bath with jet tub and laundry. Many updates include well pump, electrical, appliances are less than 5 years,

    Cheryl Roireau William Raveis Real Estate

    433 Norwich Rd, Plainfield, CT 06374
  • /9

    $160,000

    • Land
    • 10 Acres
    • $15,534 per Acre

    0 Sunnyside Dr, Thompson, CT 06277

    Rare 10-Acre Waterfront Lot - Approved & Ready to Build! Discover the perfect blend of privacy and natural beauty with this stunning 10-acre approved building lot featuring direct waterfront access. Whether you're dreaming of a year-round residence or a peaceful retreat, this property offers endless possibilities. Gently wooded with scenic views and ample space to design your ideal home, enjoy

    Cary Marcoux RE/MAX Bell Park Realty

    0 Sunnyside Dr, Thompson, CT 06277
  • /40

    $989,900

    • 3 Beds
    • 2 Baths
    • 1,808 Sq Ft

    641 5 Mile River Rd, Putnam, CT 06260

    A truly rare and magical offering - live immersed in nature on a private, ~13-acre brook-fed private pond, complete with cascading waterfall, serene wetlands, forested trails and wildflower meadows. This one of a kind sanctuary has been lovingly restored and planted to support thriving bird and wildlife habitats, including ospreys, herons, eagles, warblers and swallows. Take a sunset canoe ride,

    Jared Meehan RE/MAX Bell Park Realty

    641 5 Mile River Rd, Putnam, CT 06260
  • /40

    $465,000

    • 4 Beds
    • 2 Baths
    • 1,524 Sq Ft

    59 Ulasik Rd, Canterbury, CT 06331

    Rustic charm meets tranquil living - welcome to 59 Ulasik Road in beautiful Canterbury! Nestled in the heart of Connecticut's Quiet Corner, this circa 1973 log home offers the perfect blend of seclusion, character, and convenience. Set on an expansive 6-acre parcel surrounded by nature, this timeless retreat welcomes you with warmth and serenity. Features include a 2-car garage with a covered

    Sue Esposito Home Selling Team

    59 Ulasik Rd, Canterbury, CT 06331
  • /40

    $464,900

    • 3 Beds
    • 2 Baths
    • 1,836 Sq Ft

    156 Quaddick Rd, Thompson, CT 06277

    This one has it all! Loved for the last 35 years, this 3 bedroom 2 bathroom Ranch is more than meets the eye. Sitting on a flat 1+ AC lot, this entire property is designed for entertaining. A lined basketball court in the driveway, rear deck/patio, Above Ground pool, shed with power, the biggest playground you have seen, zipline and more! Don't let this homes age fool you also, an addition in

    Ryan LaJoie Johnston & Associates Real Estate, LLC

    156 Quaddick Rd, Thompson, CT 06277
  • /40

    $715,000

    • 4 Beds
    • 3.5 Baths
    • 4,536 Sq Ft

    101 Center Rd, Woodstock, CT 06281

    This beautiful sprawling custom colonial is set on 9 acres of land at the end of a winding long driveway and surrounded by open area. Grand living spaces with cathedral ceilings and a floor to ceiling fireplace, tons of natural light, 4 bedrooms & 3.5 bathrooms, a 1500 sqft in-law suite with additional bedroom, new appliances, spacious 2 car garage, and an out building with electricity and

    Jeff Valentine William Pitt Sotheby's Int'l

    101 Center Rd, Woodstock, CT 06281
  • /40

    $1,100,000

    • 5 Beds
    • 4 Baths
    • 5,079 Sq Ft

    76 Mill Brook Ln, Woodstock, CT 06281

    Tucked away on 6.5 private acres in the prestigious MillBrook Estates, this 5,000+ sq ft custom home offers an exceptional blend of elegance, functionality, and luxury. A long paved drive leads to this stately residence, featuring 5 bedrooms, multiple living areas, and rich architectural details throughout. The grand foyer with a hydraulic chandelier sets the tone for the craftsmanship found

    Katie Totten William Raveis Real Estate

    76 Mill Brook Ln, Woodstock, CT 06281
  • /2

    $45,000

    • Land
    • 1.50 Acres
    • $30,000 per Acre

    284 Willimantic Rd, Chaplin, CT 06235

    Build your dream home on this approved 1.5-acre lot.

    Lisa Sader-Goede Aspen Realty Group

    284 Willimantic Rd, Chaplin, CT 06235
  • /40

    $739,000

    • 5 Beds
    • 2 Baths
    • 2,443 Sq Ft

    393 N Canterbury Rd, Canterbury, CT 06331

    Built in 1750 and celebrating its 275th anniversary, this distinguished Colonial farmhouse remains a pristine exemplar of early New England architecture. Set on 8.5 acres, the estate features a secluded pond, a gently winding brook, and two traditional barns-all original to its historic rural setting. This graceful home offers 4 bedrooms, 2 full bathrooms, and approximately 2,443 sf of living

    Adam Gumula Kazantzis Real Estate, LLC

    393 N Canterbury Rd, Canterbury, CT 06331
  • /8

    $125,000

    • Land
    • 1.70 Acres
    • $73,529 per Acre

    97 Blossom Dr, Pomfret, CT 06259

    Two adjacent lots [97 BLOSSOM DR - 1.7 acres + 77 BLOSSOM DR - 2.3 acres] with south-facing slopes and scenic rolling hill views are available in a 26-lot subdivision. Both lots can be bought separately or together and offer walkout basement potential. This listing is for 97 ONLY. Underground utilities [lots would have well + engineered septic systems]. This subdivision features homes valued

    Sanam Solati New England Prestige Realty

    97 Blossom Dr, Pomfret, CT 06259
  • /9

    $125,000

    • Land
    • 2.30 Acres
    • $54,348 per Acre

    77 Blossom Dr, Pomfret, CT 06259

    Two adjacent lots [97 BLOSSOM DR - 1.7 acres + 77 BLOSSOM DR - 2.3 acres] with south-facing slopes and scenic rolling hill views are available in a 26-lot subdivision. Both lots can be bought separately or together and offer walkout basement potential. This listing is for 77 ONLY. Underground utilities [lots would have well + engineered septic systems]. This subdivision features homes valued

    Sanam Solati New England Prestige Realty

    77 Blossom Dr, Pomfret, CT 06259
  • /36

    $419,900 Open Sat 12PM - 2PM

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    367 Pine Hill Rd, Sterling, CT 06377

    Charming Ranch House in Tranquil Sterling, CT, welcome to your dream home in a small-town atmosphere! Nestled on a stunning 1.46-acre lot in the picturesque town of Sterling, Connecticut, this beautifully updated ranch house presents an exceptional blend of comfort and modern elegance. Two-bedroom, one-bathroom, updated flooring, newer appliances, perfectly designed for relaxation and nature

    Allen Gammons BHHS Commonwealth/Robert Paul

    367 Pine Hill Rd, Sterling, CT 06377
  • /39

    $2,995,000

    • 5 Beds
    • 4.5 Baths
    • 5,977 Sq Ft

    66 Bebbington Rd, Ashford, CT 06278

    PROMINENT 55-ACRE EQUESTRIAN FACILITY w/PRIMARY 6,000SF RESIDENCE w/2 APARTMENTS! Nestled amid a peaceful countryside, this exceptional horse property presents a rare opportunity to acquire a versatile estate that seamlessly combines elegant residential living w/impressive equestrian facilities. A turnkey sanctuary for those seeking solitude, sophistication, & functionality. A private gated entry

    Kiara Rusconi William Raveis Real Estate

    66 Bebbington Rd, Ashford, CT 06278
  • /38

    $389,000

    • 2 Beds
    • 1.5 Baths
    • 1,048 Sq Ft

    361 Westminster Rd, Canterbury, CT 06331

    Step into history with modern comfort at 361 Westminster Road in Canterbury, CT. Originally built in 1800, this beautifully restored 2-bedroom, 1.5-bath home blends classic New England character with thoughtful updates throughout. Featuring brand-new flooring, fresh paint, a new roof, and ductless air conditioning units, this home is completely move-in ready. The updated kitchen showcases butcher

    Adam Gumula Kazantzis Real Estate, LLC

    361 Westminster Rd, Canterbury, CT 06331
  • /6

    $242,000

    • 2 Beds
    • 1 Bath
    • 928 Sq Ft

    Unlisted Address

    House, garage and 3 additional lots being sold as 1-sale. House is in very poor condition and not livable as it sits. Total acres are 19.46. Do not access the house without permission! Driveway turn around is available, do not proceed to last house's driveway!

    Roberta Cardinal RbRE, LLC

    Unlisted Address
  • /31

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 3,983 Sq Ft

    584 Prospect St, Woodstock, CT 06281

    For those who belong to the land. Over 100 acres of private, usable terrain at the CT/MA line, Bear Hill Estate is a fully realized lifestyle retreat for the discerning equestrian or outdoor enthusiast, with effortless access to I-395, I-84, and the Mass Pike. At its heart sits a 3 bed, 2.5 bath custom log home-crafted from white pine logs hand-felled in Nova Scotia, where the bespoke cabinetry

    Jennie Kesselman Berkshire Hathaway NE Prop.

    584 Prospect St, Woodstock, CT 06281
  • /40

    $1,375,000

    • 4 Beds
    • 6 Baths
    • 4,907 Sq Ft

    30 Tyrone Rd, Pomfret Center, CT 06259

    Welcome to 30 Tyrone Road, Pomfret Center, CT. 4 Beds | 4 Full Baths | 2 Half Baths | Nearly 5,000 Sq Ft | 3.13 Acres- Set on over 3 acres in the heart of Pomfret Center, this newly built custom home offers nearly 5000 square feet of thoughtfully designed living space with panoramic scenic views and exceptional craftsmanship throughout. This property is the perfect balance of luxury,

    Jennifer Mahr RE/MAX Bell Park Realty

    30 Tyrone Rd, Pomfret Center, CT 06259
  • /2

    $2,816,000

    • Land
    • 11 Acres
    • $256,000 per Acre

    842 Hartford Pike, Dayville, CT 06241

    Property is basically level and gently sloping, Ideal site for development of Professional or Medical offices, Dental, Clinics, Retail outlets, Restaurants, Multi-Family units, Also by "Special Permit" Banks, Hotels & Motels, Self service storage facilities, distribution centers etc. See Sections 430 & 420.1 of the Killingly Zoning Regulations for a more comprehensive lists of permitted uses

    Derek Greene Derek Greene

    842 Hartford Pike, Dayville, CT 06241
  • /4

    $99,000

    • Land
    • 6 Acres
    • $15,789 per Acre

    0 Drain St, Hampton, CT 06247

    Ever dream of owning 6+ Acres of land, well dream no more. Come take a look at this secluded piece of property located in Hampton Connecticut. Located near Route 6.

    Billie Jo Parkos Coldwell Banker Realty

    0 Drain St, Hampton, CT 06247
  • /39

    $799,000 Open House 8/16

    • 3 Beds
    • 2.5 Baths
    • 3,165 Sq Ft

    14 Finn Ln, Plainfield, CT 06374

    Welcome to 14 Finn Lane - Where Modern Comfort Meets Peaceful Living. Tucked away at the end of a quiet cul-de-sac, this beautifully maintained 3-bedroom, 2.5-bath Cape Cod-style home offers 3,165 square feet of thoughtfully designed living space. Built in 2014, this home combines quality craftsmanship with modern features, ideal for both everyday living and entertaining. Step inside to an

    Greg Lehto William Pitt Sotheby's Int'l

    14 Finn Ln, Plainfield, CT 06374
  • /40

    $449,000

    • 3 Beds
    • 2 Baths
    • 2,467 Sq Ft

    226 Harris Rd, Sterling, CT 06377

    Spacious Raised Ranch with Modern Comforts and Country Charm in Sterling! Welcome to this beautifully expanded 3-bedroom, 2.5-bath raised ranch nestled on over an acre of serene countryside in Sterling. This home offers a perfect blend of comfort, space, and versatility, ideal for those seeking privacy and room to grow. Step inside to find a modern tile kitchen equipped with everything you need

    Coleen Brakenwagen Jason Mitchell Real Estate Connecticut LLC

    226 Harris Rd, Sterling, CT 06377
  • /39

    $1,250,000

    • 2 Beds
    • 2 Baths
    • 2,340 Sq Ft

    1669 Route 169, Woodstock, CT 06281

    Welcome to Hilltop Meadows-a one-of-a-kind, 60-acre luxury hay farm nestled in Connecticut's scenic "Quiet Corner." Set high above Route 169 in North Woodstock, this breathtaking property offers rolling meadows, mature forests, and serene privacy just 60 miles from Boston and 150 from Manhattan. The heart of the property is a newly updated 2-bed, 2-bath, 2,340 sq ft farmhouse blending historic

    Ryan De Lello William Pitt Sotheby's Internatiomal Realty

    1669 Route 169, Woodstock, CT 06281

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