Windham County CT Homes under $300,000

• 

  

  

  /17

  $235,000

  • Land
  • 5.11 Acres
  • $45,988 per Acre

  00 Joy Rd, Woodstock, CT 06281

  "Life is a Joy on Joy Road" Nestled in the heart of Woodstock, CT, this stunning 5.11-acre building lot offers the perfect balance of peaceful seclusion and easy access to modern conveniences. Surrounded by lush woodlands and gently rolling terrain, this property provides an idyllic setting for your dream home, offering privacy, natural beauty, and a connection to nature. Despite its serene

  

  Elizabeth Scranton

  Kazantzis Real Estate, LLC

  (860) 846-4563

  00 Joy Rd, Woodstock, CT 06281
• 

  

  

  /21

  $289,000

  • 6 Beds
  • 2 Baths
  • 1,736 Sq Ft

  96 South St, Willimantic, CT 06226

  Welcome to 96 South Street in Willimantic-a solid investment opportunity with tenants already in place through February and April 2026. This well-maintained 2-family property offers reliable rental income from day one. Recent improvements include: New windows and flooring on the first floor. Updated electrical and mechanical systems. 1-year-old roof for peace of mind and reduced maintenance

  

  Amber Jones

  KW Legacy Partners

  (860) 791-3791

  96 South St, Willimantic, CT 06226
• 

  

  

  /32

  $299,900 Open Sat 11AM - 1PM

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft

  371 Maple St, Danielson, CT 06239

  Welcome to this unique and versatile property in Killingly, where comfortable living meets incredible opportunity. The main ranch style home features 2 bedrooms and 1 full bath, offering just under 1,000 sq. ft. of thoughtfully updated space. Step inside to find a bright and welcoming layout with many recent improvements, including new appliances in the kitchen, a freshly updated bathroom, and

  Benjamin Carbone Lamacchia Realty

  371 Maple St, Danielson, CT 06239
• 

  

  

  /30

  $275,000

  • 3 Beds
  • 1 Bath
  • 1,674 Sq Ft

  245 Reardon Rd, North Grosvenordale, CT 06255

  Charming 3-bedroom, 1-bath Cape bursting with character, complete with a 2-car under-house garage, barn with hay loft & spacious outdoor living areas. Step inside to a warm & inviting layout with a carpeted living room that flows into the dining area & bright eat-in kitchen, complete with ample cabinetry & a breakfast bar. A large family room showcases wood floors, cathedral ceiling, built-in

  Tianna Wallace First Choice Realty

  245 Reardon Rd, North Grosvenordale, CT 06255
• 

  

  

  /36

  $299,900

  • 4 Beds
  • 1 Bath
  • 1,076 Sq Ft

  100 Morin Ave, Danielson, CT 06239

  Welcome to 100 Morin Ave! This charming 4-bedroom, 1-bath home is nestled in a peaceful setting, offering both comfort and tranquility. Set on a serene lot that backs up to a pond, you'll enjoy nature views right from your backyard. Inside, the home has been thoughtfully updated and is truly move-in ready. Recent improvements include new flooring and fresh paint throughout, brand-new appliances,

  Sean Doran William Raveis Real Estate

  100 Morin Ave, Danielson, CT 06239
• 

  

  /37

  $275,000

  • 3 Beds
  • 1.5 Baths
  • 1,113 Sq Ft

  36 Water St, Plainfield, CT 06374

  Don't miss this beautifully remodeled Cape-style home, featuring a thoughtfully updated interior and energy-efficient upgrades. The recently renovated kitchen boasts sleek stainless-steel appliances and modern finishes, while the updated full bathroom adds a touch of luxury. A convenient main-level primary bedroom with private half bath makes for easy living. You'll find vinyl flooring throughout

  Joshua Rodriguez CENTURY 21 Shutters & Sails

  36 Water St, Plainfield, CT 06374
• 

  

  /40

  $300,000

  • 4 Beds
  • 3.5 Baths
  • 3,523 Sq Ft

  69 Peckham Ln, Danielson, CT 06239

  Bring this storybook 1930's Tudor back to life! This classic Tudor Revival home filled with character and sits on a hill overlooking the Quinebaug River Valley. Steeply pitched rooflines, stone fireplace, charming half timbered details - nestled on a generous 1.267 acres, offers endless potential for restoration and customization. With solid bones and timeless architecture, this property is a

  Mary Collins Berkshire Hathaway NE Prop.

  69 Peckham Ln, Danielson, CT 06239
• 

  

  /12

  $299,900

  • 3 Beds
  • 1.5 Baths
  • 1,575 Sq Ft

  485 Hampton Rd, Pomfret Center, CT 06259

  New England Charmer in Historic Pomfret Center Step into this colonial-style antique, featuring timeless ship lap siding and an oversized barn. This 3-bedroom, 1.5-bath home offers wonderful curb appeal with its original white picket fence and rocking-chair-ready farmer's porch. Inside, you'll find an inviting eat-in kitchen with custom cubby storage, reminiscent of Pottery Barn style.

  Madison Litalien Berkshire Hathaway NE Prop.

  485 Hampton Rd, Pomfret Center, CT 06259
• 

  

  /21

  $289,000

  • 2 Beds
  • 1.5 Baths
  • 1,318 Sq Ft

  402 Whetstone Mills Unit 402, Dayville, CT 06241

  Peaceful 2BR Condo - Nature Lover's Dream! Private and serene, this 2-bedroom, 1.5-bath condo is nestled in a wooded setting with the calming sound of a nearby waterfall. Enjoy the scenic views along the hiking trail and the tranquil pond. This Townhouse offers a rare natural escape. Features include a private deck and an attached 2-car garage. Enjoy the benefits of homeownership with the ease of

  Laurie Mitchell Johnston & Associates Real Estate, LLC

  402 Whetstone Mills Unit 402, Dayville, CT 06241
• 

  

  /39

  $269,900

  • 4 Beds
  • 2 Baths
  • 2,275 Sq Ft

  209 Church St, Willimantic, CT 06226

  Now at an improved price! Come tour this wonderful and iconic Victorian home, nearly all interior woodwork has been preserved in its original, natural wood state. About the build date, the town records show 1879, but per the Willimantic Victorian Neighborhood Association, this home was built in 1888. This home is spacious, has replacement windows and a newer boiler and hot water heater, On the

  Rick Nassiff KW Legacy Partners

  209 Church St, Willimantic, CT 06226
• 

  

  /40

  $275,900

  • 2 Beds
  • 2 Baths
  • 804 Sq Ft

  188 Oxbow Dr, Willimantic, CT 06226

  This spacious Raised Ranch features a large kitchen with a center island and ample cabinetry, seamlessly connected to an open-concept living area-perfect for entertaining. The main level offers two comfortable bedrooms and a full bathroom. Downstairs, the finished lower level includes a second full bath and flexible space ideal for a home office, playroom, game room, or potential third bedroom.

  Peter Baker RE/MAX Bell Park Realty

  188 Oxbow Dr, Willimantic, CT 06226
• 

  

  /26

  $264,900

  • 3 Beds
  • 1 Bath
  • 1,314 Sq Ft

  34 Pleasant St Unit 4, Plainfield, CT 06374

  You can own this 3 bed home with NO money down and gain a pool for a little more than your monthly rent at $2301 a month....all taxes, insurance and HOA fees included. Take advantage of a program that has limited funding left! Rather than paying someone else's mortgage pay yourself!

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St Unit 4, Plainfield, CT 06374
• 

  

  /24

  $225,000

  • 3 Beds
  • 1.5 Baths
  • 1,496 Sq Ft

  88 Walnut St, Putnam, CT 06260

  Welcome to this charming 3 bed & 2.5 bath home. This home is conveniently located close to 395 and downtown Putnam. City sewer and water. Spacious front, side and back yard! First floor hosts a play room, a large living room, a designated dining room, open concept kitchen and full bathroom. Upstairs you will find all 3 bedrooms, the half bath and laundry area!. Windows and roof (2011) have been

  Skyla Gagnon RE/MAX Bell Park Realty

  88 Walnut St, Putnam, CT 06260
• 

  

  /28

  $229,900

  • 2 Beds
  • 1.5 Baths
  • 2,396 Sq Ft

  84 MacHine Shop Hill Rd, South Windham, CT 06266

  Take a look at this large ranch loaded with all the right features for a great price. There is a large living room, formal dining room, den, bedroom/office, sunroom with cath ceilings, fully finished walk out lower level containing a bedroom area, family room and 1/2 bath. Two car attached garage, patio and private rear yard.

  Scott Bayne Century 21 Bay-Mar Realty

  84 MacHine Shop Hill Rd, South Windham, CT 06266
• 

  /2

  $285,000

  • 6 Beds
  • 2 Baths
  • 2,170 Sq Ft

  157 S Main St, Brooklyn, CT 06234

  Two-Family Investment Opportunity! Bring your vision and tools to this spacious 2-family home featuring two identical units, each offering 3 bedrooms and 1 full bath. With a total of 6 bedrooms and 2 baths, this property has excellent potential for both owner-occupants and investors alike. The home is in need of repairs and TLC, making it a great option for those looking to build equity or

  Kerri Mullen CR Premier Properties

  157 S Main St, Brooklyn, CT 06234
• 

  

  /25

  $249,900

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  280 Cook Hill Rd, Danielson, CT 06239

  Country living at its best. Come and enjoy this beautiful Cape Style Log Cabin. This has a home just waiting for you to add your personal touches. Features three bedrooms, one and half bathroom, laundry room, fireplace, and much more potentials. Walkout basement, with a lot of possibilities. Minutes from the RI Line, and highways, shopping and all amenities.

  Glenn Stavens Aspen Realty Group

  280 Cook Hill Rd, Danielson, CT 06239
• 

  

  /22

  $225,000

  • 2 Beds
  • 1.5 Baths
  • 1,210 Sq Ft

  366 Ash St Unit 2, Willimantic, CT 06226

  Move right in to this seldom available townhouse style condo in Windham Oaks with open efficient floor plan. Kitchen overlooks the living room. Spacious second floor bedrooms and a bathroom with double sinks. Private lower level. Abundant storage space. This condo is convenient to shopping, downtown, Eastern Connecticut State University and the University of Connecticut.

  Deb Chabot RE/MAX One

  366 Ash St Unit 2, Willimantic, CT 06226
• 

  /2

  $289,900

  • 4 Beds
  • 2 Baths
  • 2,700 Sq Ft

  10 Black Hill Rd, Plainfield, CT 06374

  Great investor, property and price to sell quickly needs exterior work but inside apartments in good shape owner selling property in as is condition

  Pat Malek First Choice Realty

  10 Black Hill Rd, Plainfield, CT 06374
• 

  

  /22

  $214,000

  • 3 Beds
  • 1 Bath
  • 1,367 Sq Ft

  24 Tatem St, Putnam, CT 06260

  Welcome to this inviting 3-bedroom home with the potential for a 4th bedroom, offering flexibility for a growing household, guest room, or home office. With 1.5 bathrooms and set on a 0.18-acre lot, this property combines comfort, functionality, and convenience. Located in the heart of Putnam, CT, you'll enjoy the charm of a small-town community while being close to schools, shopping, dining, and

  Patrick Precourt Dorrance Realty

  24 Tatem St, Putnam, CT 06260
• 

  

  /8

  $300,000

  • Land
  • 37.5 Acres
  • $8,000 per Acre

  35 River Rd, Sterling, CT 06377

  Expansive 37.5-acre parcel offering excellent potential for development or subdivision, per town zoning regulations. With a mix of open space and woodlands, this versatile property lends itself to a variety of uses-from building a private estate or homestead to exploring subdivision options for future development. Enjoy the peace and privacy of a rural setting with convenient access to nearby

  Bradley Kazarian Executive Real Estate Inc.

  35 River Rd, Sterling, CT 06377
• 

  

  /22

  $289,900

  • 3 Beds
  • 1.5 Baths
  • 2,236 Sq Ft

  360 N Society Rd, Canterbury, CT 06331

  EXCEPTIONAL NEW PRICE!!! on this opportunity to renovate your own dream home to YOUR liking! A great opportunity to build GREAT EQUITY and be located in beautiful Canterbury, with choices of school, options for animals and gardens! This large house is currently mostly gutted and waiting for you to complete. 2 car garage attached to the house, and oversized 2 car garage workshop great for home

  Michelle Pivin Kazantzis Real Estate, LLC

  360 N Society Rd, Canterbury, CT 06331
• 

  

  /33

  $249,000

  • 3 Beds
  • 1 Bath
  • 1,076 Sq Ft

  222 Southridge Dr, Willimantic, CT 06226

  Welcome to 222 Southridge Drive, a spacious and inviting 3-bedroom, 1-bath ranch-style home offering comfortable, easy living with thoughtful cosmetic updates throughout. Step inside to find a bright and inviting living space featuring freshly painted walls, updated flooring, and plenty of natural light. The kitchen offers ample cabinet space and a functional layout perfect for everyday living

  Taylor Gildein Re/Max Results

  222 Southridge Dr, Willimantic, CT 06226
• 

  

  /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
• 

  

  /21

  $210,000

  • 1 Bed
  • 1 Bath
  • 974 Sq Ft

  45 Main St Unit 202, Plainfield, CT 06374

  This sun-filled end-unit 1-bedroom, 1-bath condo offers extra privacy, soaring two-story windows, and tranquil views of park-like grounds along the river. Inside, you'll find a dedicated office, in-unit laundry, central air, and an open living space perfect for both relaxing and entertaining. Convenient elevator in building with beautifully landscaped surroundings, this home combines modern

  Deanna Marler Mott & Chace Sotheby's Intl Rt

  45 Main St Unit 202, Plainfield, CT 06374
• 

  

  /19

  $228,500

  • 4 Beds
  • 1 Bath
  • 1,078 Sq Ft

  129 Walnut St, Willimantic, CT 06226

  Charming antique 1915 home in down town Willimantic on a beautiful corner lot showcasing its 20th century craftsmanship. The authentic wooden white picket fence is a beautiful addition to all of the craftsmanship . A two story carriage house style garage detached from the home offering an abundance of space and access onto two roads. Conveniently just walking distance from Eastern CT State

  Lisa Therecka Therecka & Associates LLC

  129 Walnut St, Willimantic, CT 06226
• 

  

  /5

  $290,000

  • 2 Beds
  • 1.5 Baths
  • 1,196 Sq Ft

  10 Laurel Hill Dr, Woodstock Valley, CT 06282

  LOCATION, LOCATION, LOCATION!!!! This cozy 2-3 bedroom ranch is nestled on .40 of an acre lot with views of Lake Bunggee. Lake Bunggee is a private lake association for residents only. Access to the beach and boat launch is across the street. The roof is only 10 years old, electrical was updated and new wood decks on each side of the home. One floor living including a woodburning fireplace for

  Simonne Corriveau KW Legacy Partners

  10 Laurel Hill Dr, Woodstock Valley, CT 06282
• 

  

  /25

  $249,900

  • 5 Beds
  • 2.5 Baths
  • 1,480 Sq Ft

  19 Boston Post Rd, North Windham, CT 06256

  Step into this charming 5-bedroom, 2.1-bath home that's full of character and solid bones-just waiting for your personal touch. Offering generous living space and a functional layout, this property is ideal for anyone looking for room to grow. A large storage shed out back provides plenty of space for tools, hobbies, or extra storage. Centrally located, you'll enjoy easy access to schools,

  Victor Santana Santana Realty Group LLC

  19 Boston Post Rd, North Windham, CT 06256
• 

  

  /21

  $300,000

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  29 Prospect St Unit A, Putnam, CT 06260

  Welcome to 29 Prospect St Unit A - a move-in ready, low-maintenance home in the heart of Putnam! This spacious 3-bedroom, 1.5-bath condo offers the perfect blend of comfort and convenience. Step inside to find beautifully refinished hardwood floors that flow through the bright and open living spaces. The kitchen features ample cabinet space, stainless steel appliances, and sliders leading to a

  Kendra Bonette Coldwell Banker Realty

  29 Prospect St Unit A, Putnam, CT 06260
• 

  

  /36

  $299,999 Open Thu 5:30PM - 6:30PM

  • 2 Beds
  • 1.5 Baths
  • 1,218 Sq Ft

  257 Sabin St Unit 23, Putnam, CT 06260

  Due to unforeseen personal circumstances, the seller must relocate after only a short time in the home. While this move comes sooner than expected, it presents a unique opportunity for the next owner to enjoy a thoughtfully maintained property that has seen recent investment and care. Well maintained by the original owner, this townhouse is located in a peaceful setting at the back of the

  Kim Synott Castinetti Realty Group

  257 Sabin St Unit 23, Putnam, CT 06260
• 

  

  /29

  $269,900

  • 3 Beds
  • 1 Bath
  • 1,350 Sq Ft

  34 Pleasant St, Plainfield, CT 06374

  You can own this 3 bed home with NO money down and gain a pool for a little more than your monthly rent at $2353 a month....all taxes, insurance and HOA fees included. Take advantage of a program that has limited funding left! Rather than paying someone else's mortgage pay yourself!

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St, Plainfield, CT 06374
• 

  

  /40

  $299,000

  • 6 Beds
  • 2 Baths
  • 2,981 Sq Ft

  87 North St, Willimantic, CT 06226

  TWO HOUSES ON ONE PROPERTY! This unique investment opportunity at 87-89 North Street in Willimantic, CT, presents a compelling proposition for investors. The property comprises TWO single-family homes situated on a single lot, each with its own driveway and access to a large garage located conveniently on the front house's driveway. The rear house, a charming 1,224 square-foot dwelling,

  Toni Iandoli William Pitt Sotheby's Int'l

  87 North St, Willimantic, CT 06226
• 

  

  /26

  $279,900

  • 3 Beds
  • 1.5 Baths
  • 1,429 Sq Ft

  34 Pleasant St Unit 8, Plainfield, CT 06374

  You can own this 3 bed home with NO money down and gain a pool for a little more than your monthly rent at $2366 a month....all taxes, insurance and HOA fees included. Take advantage of a program that has limited funding left! Rather than paying someone else's mortgage pay yourself!

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St Unit 8, Plainfield, CT 06374
• 

  

  /26

  $249,900

  • 3 Beds
  • 1.5 Baths
  • 1,259 Sq Ft

  34 Pleasant St Unit 7, Plainfield, CT 06374

  You can own this home with NO money down for only $2,108 a month....all taxes, insurance and HOA fees included. Take advantage of a program that has limited funding left! Rather than paying someone else's mortgage pay yourself!

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St Unit 7, Plainfield, CT 06374
• 

  

  /25

  $219,900

  • 2 Beds
  • 1 Bath
  • 1,215 Sq Ft

  34 Pleasant St Unit 6, Plainfield, CT 06374

  You can own this home with NO money down for only $1,939 a month....all taxes, insurance and HOA fees included. Take advantage of a program that has limited funding left! Rather than paying someone else's mortgage pay yourself!

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St Unit 6, Plainfield, CT 06374
• 

  

  /25

  $239,900

  • 2 Beds
  • 1 Bath
  • 1,343 Sq Ft

  34 Pleasant St Unit 5, Plainfield, CT 06374

  You can own this home with NO money down for only $2,155 a month....all taxes, insurance and HOA fees included. Take advantage of a program that has limited funding left! Rather than paying someone else's mortgage pay yourself!

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St Unit 5, Plainfield, CT 06374
• 

  

  /24

  $219,900

  • 2 Beds
  • 1 Bath
  • 1,188 Sq Ft

  34 Pleasant St Unit 3, Plainfield, CT 06374

  You can own this home with NO money down for only $1,955 a month....all taxes, insurance and HOA fees included. Take advantage of a program that has limited funding left! Rather than paying someone else's mortgage pay yourself!

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St Unit 3, Plainfield, CT 06374
• 

  

  /10

  $225,000

  • Land
  • 3.72 Acres
  • $60,484 per Acre

  80 Averill Rd, Pomfret, CT 06259

  Approved, shovel ready Commercial Building Site. Part of a 15.9 acre 3 Lot approved subdivision. This is Lot #3.04 the entrance is on Averill Rd It has 3.72 Acres. Just off US Route 44.Shared driveway access with Commercial Property owned by Centerville Bank. Zoned Village Commercial. Ideal for Retail Centers & Strip Malls. Drive-Thru, Restaurants, Cafe', Chains, Grocery Stores & Convenience

  Mary Collins Berkshire Hathaway NE Prop.

  80 Averill Rd, Pomfret, CT 06259
• 

  

  /5

  $225,000

  • Land
  • 3.86 Acres
  • $58,290 per Acre

  00 Mashamoquet Rd, Pomfret, CT 06259

  Approved, shovel ready Commercial Building Site. Part of a 15.9 acre 3 Lot approved subdivision. This is Lot #3.02 It has 3.86 acres. Boarders the popular Airline State Park Trail in Back. It is directly on US Route 44. Just after the Commercial Property owned by Centerville Bank. Zoned Village Commercial. Ideal for Retail Centers & Strip Malls. Drive-Thru, Restaurants, Cafe', Chains, Grocery

  Mary Collins Berkshire Hathaway NE Prop.

  00 Mashamoquet Rd, Pomfret, CT 06259
• 

  

  /16

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,654 Sq Ft

  297 Main St, Hampton, CT 06247

  Adventure Awaits in This 1850 Hampton Gem! Step back in time with this solidly built 1850 home featuring stunning exposed beams like no other! Located on historic Main Street in Hampton, CT-just outside of Pomfret and surrounded by picturesque farmland-you'll enjoy the serenity of country living while still being close to Killingly and other local conveniences. The home has been taken down to

  Missy Greene eXp Realty

  297 Main St, Hampton, CT 06247
• 

  

  /4

  $210,000

  • Land
  • 7.33 Acres
  • $28,649 per Acre

  308 Orchard Hill Rd, Pomfret Center, CT 06259

  VACANT COMMERCIALLY ZONED 7.33 ACRES ON BUSY ORCHARD HILL ROAD- NOTE: THIS IS ZONE COMMERCIAL VILLAGE - NO CURRENT TESTING RESULTS AVAILABLE

  Jim Nispel Coldwell Banker Realty

  308 Orchard Hill Rd, Pomfret Center, CT 06259

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