Windham County CT Homes under $300,000

• 

  

  

  /12

  $250,000

  • Land
  • 5 Acres
  • $48,924 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
• 

  

  

  /3

  $239,900

  • 1 Bed
  • 1 Bath
  • 540 Sq Ft

  189 Chaplin Rd, Eastford, CT 06242

  Charming 1-Bedroom Cottage - Low-Maintenance Living This cozy 1-bedroom, 1-bath cottage offers simple and efficient living in a peaceful setting. With 540 square feet of space, it's the perfect option for a minimalist lifestyle, weekend getaway, or investment property. Inside, you'll find a comfortable layout with an open living area, full kitchen, and a nicely sized bedroom. Electric heat

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 916-6048

  189 Chaplin Rd, Eastford, CT 06242
• 

  

  

  /19

  $299,000

  • 6 Beds
  • 2 Baths
  • 1,932 Sq Ft

  100 South St, Willimantic, CT 06226

  Discover 100 South Street in Willimantic-a great opportunity to own a fully occupied 2-family home with solid rental income and key updates already done. The first floor unit hasbeen remodeled, including fresh flooring and paint, and a brand-new furnace. The property also features a 2-year-old roof, offering long-term durability and reduced future expenses. With great tenants already in place,

  

  Amber Jones

  KW Legacy Partners

  (860) 831-4634

  100 South St, Willimantic, CT 06226
• 

  

  

  /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
• 

  

  

  /5

  $299,000

  • 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
• 

  

  /13

  $300,000

  • 2 Beds
  • 1 Bath
  • 1,316 Sq Ft

  29 Cheney Rd, Pomfret Center, CT 06259

  Tucked away in the desirable town of Pomfret, CT, this charming single-family home offers the perfect blend of privacy, space, and convenience. Set on a generously sized yard, the property is surrounded by natural beauty, offering a peaceful, secluded atmosphere while still being close to local amenities. A spacious back deck provides an ideal spot for outdoor relaxation or entertaining. The home

  Kyle Seyboth Century 21 Limitless

  29 Cheney Rd, Pomfret Center, CT 06259
• 

  

  /24

  $289,900

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft

  53 Cleveland St, Putnam, CT 06260

  Welcome Home to 53 Cleveland St located in the heart of Putnam. Located in a quiet neighborhood, this 2 bed home has a an open concept kitchen/ living/ dining area perfect for entertaining. You'll be pleasantly surprised by the oversized bedrooms and well appointed kitchen and bath. Theres a extra heated bonus room off the living area perfect for an office or play room. Let's not forget about the

  Jarrod Lewis J. Christopher Real Estate Grp

  53 Cleveland St, Putnam, CT 06260
• 

  

  /18

  $274,900

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

  20 Greystone St, Willimantic, CT 06226

  Fully renovated 3 bedroom, 1 1/2 Bathrooms on a level lot. Updated plumbing, electrical, insulation, furnace, water heater, roof, appliances, kitchen, all new windows and framed in basement ready for completion to add additional bedrooms or space. All public utilities. Dont miss your chance to see this move in ready home !

  Frank Fonteyn Prestige Realty Group

  20 Greystone St, Willimantic, CT 06226
• 

  

  /13

  $280,000

  • 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
• 

  

  /17

  $259,000 Pre-Foreclosure

  • 3 Beds
  • 1.5 Baths
  • 1,624 Sq Ft

  77 Plains Rd, Windham, CT 06280

  BEST AND FINAL TUESDAY 7/15 5PM. Investors Take Notice! Endless potential awaits in this 3-bedroom, 1.5-bath home with an attached 2-car garage. Whether you're looking to renovate, flip, or hold as a rental, this property offers unlimited possibilities. Bring your vision and transform this space into something truly special! Estate is subject to probate approval, and property just came out of

  Lisa Barstow Simply Sold Real Estate

  77 Plains Rd, Windham, CT 06280
• 

  

  /8

  $225,000

  • 4 Beds
  • 12 Baths
  • 988 Sq Ft

  395 Hartford Pike, Dayville, CT 06241

  Welcome to this well-maintained 2-family home located in the heart of Dayville! Whether you're looking for an owner-occupied residence with rental income or a solid investment property, this one checks all the boxes. Each unit offers 2 bedrooms and 1 bath . Live in one side and rent the other unit With strong rental history and separate utilities, it's truly investor-friendly. Conveniently

  Courtney Ravenelle RE/MAX Bell Park Realty

  395 Hartford Pike, Dayville, CT 06241
• 

  

  /38

  $200,000

  • 3,008 Sq Ft

  326 Route 169, Wood Stock, CT 06281

  INVESTORS TAKE NOTICE! All the work on the outside of this building has been done! New roof, new windows, front deck has been shored up, siding has been redone and painted, porch has been redone and a handicap ramp has been put in. Inside needs complete work. No plumbing or furnace, no bathrooms, empty canvas for you to come in and make this building a home. Think of this bldg as a condo, since

  Diane White CR Premier Properties

  326 Route 169, Wood Stock, CT 06281
• 

  

  /13

  $279,900

  • 4 Beds
  • 2.5 Baths
  • 1,520 Sq Ft

  10 Tiffany St, Brooklyn, CT 06234

  2-Family with one unit ready for occupancy! 2/3 bedrooms with living room, eat in appliance kitchen with breakfast bar, & 1/2 bath. Room could be dining room or bedroom. Staircase leads to full bathroom with glass shower and 2 spacious bedrooms with plenty of closet space. Porch to enjoy your evenings. City water, sewer and gas! Unit B is rented and has a large deck, 1 bedroom, large living room,

  Christine Johnson RE/MAX One

  10 Tiffany St, Brooklyn, CT 06234
• 

  

  /12

  $205,000

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  27 August Dr, Brooklyn, CT 06234

  ATTENTION- Rare opportunity to own this affordable 3-bedroom, 2-bath mobile home on its own land in Brooklyn, CT!! This property offers a spacious layout with a large living area, an eat-in kitchen, and a primary bedroom with a full bath. No park fees, no shared land-just your own space in a quiet residential setting. Conveniently located near schools, shopping, and Route 6 for an easy commute.

  Brecken Ellsworth Kazantzis Real Estate, LLC

  27 August Dr, Brooklyn, CT 06234
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  /26

  $299,500

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  60 Sachem Dr Unit 60, Plainfield, CT 06374

  Welcome to this beautifully maintained END unit condo! 3 Bedrooms and 2 full bathroom! Open concept living room/ dining room.Tastefully updated. Great kitchen with granite countertops and stainless steel appliances. Lovely back deck off the kitchen over looking the backyard.1 Car under house garage with an additional storage/utility room. Central AC. A must see condo that will NOT last! Low HOA

  Skyla Gagnon RE/MAX Bell Park Realty

  60 Sachem Dr Unit 60, Plainfield, CT 06374
• 

  

  /26

  $229,900

  • 2 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  11 Fawn Ridge, Woodstock, CT 06281

  Nestled in the Fawn Ridge community, this tastefully updated 2-bedroom, 1.5-bath condo offers low-maintenance living in a prime location just minutes from the Woodstock Fairgrounds. Inside, you'll find beautiful hardwood floors and an inviting layout. The kitchen opens to the dining and living areas, seamlessly connecting the spaces. The full bathroom has been upgraded with a tiled shower stall,

  Kimberly Frasier Real Broker CT, LLC

  11 Fawn Ridge, Woodstock, CT 06281
• 

  

  /40

  $279,900

  • 7 Beds
  • 2 Baths
  • 2,422 Sq Ft

  110 Franklin St, Danielson, CT 06239

  Charming 2-family home in Killingly, CT, offering strong investment potential or multi-generational living! The first unit features 4 spacious bedrooms and 1 full bath, while the second unit offers 3 bedrooms and 1 full bath-perfect for rental income or extended family. This property is brimming with potential and awaits your personal touch and TLC to truly shine. Located in an incredibly

  Kyle Seyboth Century 21 Limitless

  110 Franklin St, Danielson, CT 06239
• 

  

  /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
• 

  

  /25

  $250,000

  • 3 Beds
  • 1.5 Baths
  • 1,088 Sq Ft

  18 Highland St, Moosup, CT 06354

  Plainfield ADORABLE remodeled Colonial with 2 to 3 bedrms, 1.5 baths on a dead end street. Beautifully NEW kitchen w/GRANITE COUNTERS, SS appliances, hardwood floors and a large deck to your back yard. Separate dining rm with refinished Hardwd floors and nice living rm with refinished hardwd floors. 3 bedrms on 2nd floor with new flooring. 3rd bedrm can be a bedrm, loft, play room or extra family

  Irene Adams Signature Properties of NewEng

  18 Highland St, Moosup, CT 06354
• 

  

  /5

  $235,000

  • 4 Beds
  • 2 Baths
  • 2,259 Sq Ft

  434 Pleasant St, Willimantic, CT 06226

  This 2 story multi-family gem offers two spacious 2-bedroom, 1-bath units (approx. 1,100 sq ft each), one upstairs and one downstairs-both currently leased by long-term tenants with separate utilities, providing hassle-free rental income. Many upgrades have already been done here. Schedule a showing for a better look of this property. Check agent remarks

  Chad Saba I.M.A. Realty LLC

  434 Pleasant St, Willimantic, CT 06226
• 

  

  /22

  $200,000

  • 3 Beds
  • 1 Bath
  • 1,068 Sq Ft

  117 State Ave, Dayville, CT 06241

  Welcome to 117 State Avenue in the Dayville section of Killingly. This 3 bedroom 1 bath home offers a unique opportunity for investors, rehabbers, or buyers looking to bring new life to a home with great potential. The property features a solid structure with classic bones and a new roof installed in 2023, providing a valuable head start on renovations. While the interior will need updating, the

  Ryan Braunagel Keller Williams Realty Prtnrs.

  117 State Ave, Dayville, CT 06241
• 

  

  /28

  $200,000

  • 2 Beds
  • 1 Bath
  • 1,077 Sq Ft

  301 Brick Top Rd, Windham, CT 06280

  Recently remodeled and ready for its next owner! This 2-bedroom, 1-bath ranch has a lot to offer. On the list is a brand new kitchen and appliances, brand new spacious bathroom with a stand-up cabinet shower, new flooring throughout, many replacement windows and lots of fresh paint inside and out. The open-concept floor plan flows from a spacious living room into a sunny dining area off the

  Anne Newmyer Simply Sold Real Estate

  301 Brick Top Rd, Windham, CT 06280
• 

  

  /13

  $210,000

  • 1 Bed
  • 1 Bath
  • 780 Sq Ft

  1 Cornfield Point, Woodstock, CT 06281

  Welcome to the coveted living of Cornfield point. Few condos are available in this lovely complex located close to Roseland Park and the golf course. This spacious unit has large living room with vaulted ceilings and sliders that open to a patio and lovely back yard. Small Kitchen and dining area. One big bedroom and full bath. Dry basement could easily be finished for a family area. Needs

  Amy Vinal Pine Knoll Real Estate

  1 Cornfield Point, Woodstock, CT 06281
• 

  

  /25

  $279,900

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

  34 Pleasant St Unit 8, Plainfield, CT 06374

  NOTE: Estimated Payments are incorrect on Zillow, Realtor and other websites.

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St Unit 8, Plainfield, CT 06374
• 

  

  /25

  $269,900

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

  34 Pleasant St Unit 7, Plainfield, CT 06374

  NOTE: Estimated Payments are incorrect on Zillow, Realtor and other websites.

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St Unit 7, Plainfield, CT 06374
• 

  

  /24

  $239,900

  • 2 Beds
  • 1 Bath
  • 1,215 Sq Ft

  34 Pleasant St Unit 6, Plainfield, CT 06374

  NOTE: Estimated Payments are incorrect on Zillow, Realtor and other websites.

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St Unit 6, Plainfield, CT 06374
• 

  

  /25

  $289,900

  • 2 Beds
  • 1 Bath
  • 1,343 Sq Ft

  34 Pleasant St Unit 5, Plainfield, CT 06374

  *** Seller incentivized financing options available through our preferred lender! Project has already been preapproved! *** Rates as low as 6.25% fixed for 30 years! No points paid by the buyer! Exclusively available thru our preferred lender for buyers purchasing a unit as a primary residence and meeting other criteria. *** Example offerings in attachments! Contact info included for further

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St Unit 5, Plainfield, CT 06374
• 

  

  /23

  $249,900

  • 2 Beds
  • 1 Bath
  • 1,188 Sq Ft

  34 Pleasant St Unit 3, Plainfield, CT 06374

  NOTE: Estimated Payments are incorrect on Zillow, Realtor and other websites.

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St Unit 3, Plainfield, CT 06374
• 

  

  /15

  $249,900

  • Land
  • 12 Acres
  • $21,178 per Acre

  634 Parcel A 5 Mile River Rd, Putnam, CT 06260

  Discover the beauty and serenity of this remarkable 11.8-acre parcel in scenic East Putnam. Highlighted by a stunning 2-acre pond, this property features over 1,300 feet of road frontage and offers a unique blend of natural beauty and thoughtful environmental stewardship. The pond and surrounding wetland ecosystem have been meticulously restored to a healthy, thriving habitat, including invasive

  Jared Meehan RE/MAX Bell Park Realty

  634 Parcel A 5 Mile River Rd, Putnam, CT 06260
• 

  

  /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

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft

  227 Ash St, Willimantic, CT 06226

  This charming older home offers classic details and great potential. It features a welcoming front porch and a large deck off the living room, perfect for outdoor relaxation. Inside, the home includes four bedrooms and two full bathrooms, along with a cozy wood stove for added warmth.There is plenty of opportunity to make it your own. The private driveway provides off-street parking, and the

  Kim Benoit CENTURY 21 Shutters & Sails

  227 Ash St, Willimantic, CT 06226
• 

  

  /4

  $210,000

  • Land
  • 7 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
• 

  

  /10

  $300,000

  • Land
  • 9 Acres
  • $32,967 per Acre

  384 Killingly Rd, Pomfret, CT 06259

  9.1 acres features frontage on Route 101 and appears to have substantial frontage on Nora Lane. CV zone allows many commercial uses as well as others by special permit. Possible subdivision. Please see Pomfret Zoning Regulations. Lot cleared.

  Richard Loomis RE/MAX Bell Park Realty

  384 Killingly Rd, Pomfret, CT 06259
• 

  

  /19

  $300,000

  • 2 Beds
  • 2 Baths
  • 2,240 Sq Ft

  338 Brooklyn Rd, Pomfret Center, CT 06259

  Restore this beauty to its full potential!! Complete rehab is needed on this antique home. Beautiful country location in Pomfret. A new electrical service has been installed, but the rest is up to you! Discover the perfect escape in this stunning 4 acre parcel located in the serene and sought-after area of Pomfret. Enjoy the peaceful surroundings with a picturesque pond that enhances the

  Cathy Duprey Duprey Real Estate, LLC

  338 Brooklyn Rd, Pomfret Center, CT 06259
• 

  

  /10

  $219,500

  • Land
  • 22 Acres
  • $10,209 per Acre

  00 Sarah Pearl Rd, Hampton, CT 06247

  Prime Development Opportunity: 21.5 Acres on Sarah Pearl Road, Hampton, Connecticut Overview: Presenting a rare opportunity to own 21.5 acres of pristine forested land located on Sarah Pearl Road in the picturesque town of Hampton, Connecticut. This parcel of land is perfectly positioned for development, offering both natural beauty and potential for future growth. Property Details: Size: 21.5

  Peter Plourde Berkshire Hathaway NE Prop.

  00 Sarah Pearl Rd, Hampton, CT 06247
• 

  

  /24

  $215,000

  • Land
  • 19 Acres
  • $11,316 per Acre

  XO Green Rd, Woodstock, CT 06281

  Appealing 19 acres on the corner of Green Rd & RT 169 has 1,510 feet of road frontage, the vast majority is dry and is subdividable. Road frontage points are flagged with surveyor's ribbon. Frontage on Green Rd goes around & has frontage on both sides of house #27. The westerly portion of the land goes up to a high, private, mostly level plateau. Minor subdivisions up to 3 lots, lot size must be

  Dennis Duga Dr. LAND

  XO Green Rd, Woodstock, CT 06281
• 

  /2

  $237,500

  • 5 Beds
  • 1 Bath
  • 2,548 Sq Ft

  33 MacHine Shop Hill Rd, South Windham, CT 06266

  Welcome to a unique chance to own a spacious multi-family property in the charming South Windham area. This home presents an outstanding opportunity for investors seeking rental income and invites a creative new owner to explore the renovation potential. With a total of five bedrooms and two bathrooms spread across 2,548 square feet, this property is ideal for offering flexibility to operate as a

  Franchesca Pescatello Prue Realty LLC

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

  /2

  $295,000

  • 3 Beds
  • 2.5 Baths
  • 2,248 Sq Ft

  Unlisted Address

  Raised Ranch on 1 acre lot. Three beds, three full baths, partially finished lower level basement. Home is being sold in "as is" condition. Home Inspections are for informational purposes only. Home will require work!

  Valerie Yankus Property Shoppe, LLC

  Unlisted Address
• 

  /2

  $300,000

  • Land
  • 19 Acres
  • $15,625 per Acre

  0 Lowell Davis Rd, Thompson, CT 06277

  Approved 19.2 AC building lot located on one of the most private, but convenient, roads in all of Thompson. Owner has completed a lot split and this approved lot is ready for your designs. Lot features beautiful stone walls, is lightly wooded, and very private. A lot of this size allows for many recreational activities including hiking, ATV use, along with hunting. Lot is located very close to

  Ryan LaJoie Johnston & Associates Real Estate, LLC

  0 Lowell Davis Rd, Thompson, CT 06277

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