52

Windham County CT Homes under $400,000

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  • /8

    $350,000

    • Land
    • 4.57 Acres
    • $76,586 per Acre

    9 Kennedy Dr, Putnam, CT 06260

    A great location in a convenient, highly visible and well-traveled spot right off of Route I-395. This listing includes two separate adjoining parcels, a 2.57-acre piece fronts Kennedy Drive and 2-acre rear piece on back side of Park Street. Property is across from access to the Tech Park and YMCA. Putnam is a great place for your business! Bring your ideas / proposals and let us assist you with

    Agent Photo

    Tina Lajoie

    William Raveis Real Estate

    (860) 754-3940

    9 Kennedy Dr, Putnam, CT 06260
  • /14

    $330,000

    • 8 Beds
    • 2 Baths
    • 2,910 Sq Ft

    85 Oak St, Willimantic, CT 06226

    Charming, Victorian-style side-by-side multifamily in a desirable part of Willimantic! This oversized home blends classic details with smart functionality. Each unit offers a spacious layout, large rooms, and bonus areas-including a beautifully finished walk-up attic on the vacant #83 side. One unit is recently available, (seeking tenants) offering an ideal opportunity for owner-occupants or

    Agent Photo

    Amber Jones

    KW Legacy Partners

    (860) 485-7698

    85 Oak St, Willimantic, CT 06226
  • /16

    $374,900

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft

    19 Squaw Rock Rd, Danielson, CT 06239

    Own Your Dream Home with Zero Money Down! Unlock the door to your future with an exclusive offer: Purchase this home and receive $3,749 back in closing costs credits OR $2,216 per month at an exceptional financing rate of 5.87% APR with ZERO down payment available for those who qualify. Your Private Oasis Awaits! Welcome to this beautifully maintained raised ranch, just nine years young and

    Nathan Clark Your Home Sold Guaranteed Realty, The Nathan Clark Team

    19 Squaw Rock Rd, Danielson, CT 06239
  • /32

    $400,000

    • 3 Beds
    • 2.5 Baths
    • 3,502 Sq Ft

    150 Fabyan Rd, North Grosvenordale, CT 06255

    Located in Thompson, Connecticut, this contemporary modern home, built in 1990, sits on a spacious 8.12-acre lot. The property presents a unique opportunity for the right person, offering a distinctive floor plan characterized by high ceilings, wide-open rooms, and a grand foyer, eat-in kitchen, dining area, family room and so much more. While the house may require some work to restore it to its

    Jennifer Jackson Berkshire Hathaway NE Prop.

    150 Fabyan Rd, North Grosvenordale, CT 06255
  • /39

    $389,000

    • 4 Beds
    • 2 Baths
    • 2,218 Sq Ft

    16 Center St, Putnam, CT 06260

    Come see this wonderful & charming farmhouse style home. With a little updating/ painting this home would bring this home back to its glory. Eat in kitchen with side pantry area. First floor full bathroom. Secondary staircase to upstairs. Formal living room large enough for that oversized table, buffet, and china closet you may have. Fireplaced living room with good floors and coffered ceilings

    Robin Smith RE/MAX Bell Park Realty

    16 Center St, Putnam, CT 06260
  • /25

    $399,900

    • 2 Beds
    • 1.5 Baths
    • 1,356 Sq Ft

    248 Rukstella Rd, Brooklyn, CT 06234

    BRAND NEW BEAUTIFUL 2025 Cape on 3.73 PRIVATE ACRES sits way back off dead end road. Gorgeous GRANITE Counters, island and STAINLESS APPLIANCES open to dining/ large living room with bright windows and SLIDER leading to HUGE 10 x 24 Deck to enjoy your Summer evenings. Large Office/ Den on main level, utility room and FULL bathroom. NEW carpet on stairs and 2 SPACIOUS bedrooms with plenty of

    Christine Johnson RE/MAX One

    248 Rukstella Rd, Brooklyn, CT 06234
  • /14

    $385,000

    • 4 Beds
    • 2 Baths
    • 1,849 Sq Ft

    357 Green Hollow Rd, Danielson, CT 06239

    Set back on a quiet, secluded lot, this home has something for everyone. The large, open yard is a perfect place for pets to run and is ideal for anything from entertaining and outdoor activities to growing a garden or just relaxing next to a fire pit. When you step inside, you will be surprised at how much more this home has to offer! On the main level, you will find a large, sunny kitchen, a

    Stephanie Harkins Coldwell Banker Realty

    357 Green Hollow Rd, Danielson, CT 06239
  • /40

    $375,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    40 Deerfield Dr, Ashford, CT 06278

    Lake life at its finest-fully updated and turn-key in the desirable Lake Chaffee community! Welcome to 40 Deerfield Drive, where every detail has been thoughtfully renovated for effortless living. This 3-bedroom, 2-bath ranch boasts a stunning kitchen with quartz countertops, all-new appliances, and modern lighting. Enjoy the warmth of the wood-burning fireplace in the vaulted living room that

    Michael Hvizdo Coldwell Banker Realty

    40 Deerfield Dr, Ashford, CT 06278
  • /27

    $380,000 Open Sat 11AM - 12:30PM

    • 3 Beds
    • 2 Baths
    • 1,869 Sq Ft

    90 Broad St, Danielson, CT 06239

    This well-maintained 3-bedroom, 1.5-bath antique home offers timeless charm and practical updates throughout. Enjoy the warmth of refinished hardwood floors and fresh paint in every room. The kitchen features stainless steel appliances and flows directly to a cozy screened-in porch-perfect for morning coffee or evening relaxation. A beautifully updated full bath, first-floor laundry, and a

    Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

    90 Broad St, Danielson, CT 06239
  • /28

    $400,000

    • 4 Beds
    • 1.5 Baths
    • 1,582 Sq Ft

    171 David Cir, Putnam, CT 06260

    Welcome to this warm and inviting four bedroom one and a half bath, raised ranch, proudly cared for by its original owners for more than half a century. Set on a beautifully landscaped lot, this home radiates pride of ownership. Step inside to discover updated flooring throughout the main living areas (2024). Replacement windows with a lifetime warranty fill the space with natural light and offer

    Valerie MacNeil Kazantzis Real Estate, LLC

    171 David Cir, Putnam, CT 06260
  • /35

    $375,000

    • 5 Beds
    • 3 Baths
    • 1,810 Sq Ft

    15 Stanmark Dr, Plainfield, CT 06374

    Versatile 4-Bedroom Home with In-Law Suite in Convenient Plainfield Location! Welcome to this spacious and well-maintained 4-bedroom, 2-bathroom home in the heart of Plainfield! With versatile living space and a fully equipped in-law apartment, this property is perfect for multi-generational living, guests, or potential rental income. The home features durable vinyl siding, public water and

    Jason Kenny Real Broker CT, LLC

    15 Stanmark Dr, Plainfield, CT 06374
  • /20

    $379,995

    • 5 Beds
    • 2 Baths
    • 3,112 Sq Ft

    413 Maple St, Killingly, CT 06239

    Step inside this meticulously remodeled, oversized Colonial that blends timeless charm with modern elegance. This expansive home offers generous living spaces, perfect for both entertaining and comfortable everyday living. Every detail has been carefully updated, featuring gleaming brand-new hardwood floors, designer tile showers, and luxurious stone countertops throughout. The flowing layout

    Marco Epifani eRealty Advisors, Inc.

    413 Maple St, Killingly, CT 06239
  • /31

    $374,900

    • 3 Beds
    • 2.5 Baths
    • 1,802 Sq Ft

    3 Julian Cir Unit 3, Sterling, CT 06377

    BACK ON MARKET DUE TO BUYER FINANCING FALLING THROUGH! Charming Young Colonial with 3B, 2.5BA & Low Maintenance Living! Welcome to Sterling Hills Estate! This lovely home is located in a desirable community with an HOA of only $140 a month that takes care of ALL GROUNDS MAINTENANCE! This home lets you enjoy more leisure time and less upkeep. Gleaming hardwood floors throughout first floor and a

    Kim Ricard Priority Real Estate Group,LLC

    3 Julian Cir Unit 3, Sterling, CT 06377
  • /34

    $374,999

    • 2 Beds
    • 2 Baths
    • 884 Sq Ft

    3 Arnold Ln, Dayville, CT 06241

    Welcome to 3 Arnold Lane, situated in the highly desirable area of Alexander's Lake! This fully remodeled year-round cottage has so much to present! As you drive in, you'll be welcomed by a stunning view of your new home featuring white vertical siding and grey stone accents, farmers porch, and a 14'x16' rooftop deck perfect for entertaining friends, family, and neighbors while enjoying the

    Katie Spenard Kazantzis Real Estate, LLC

    3 Arnold Ln, Dayville, CT 06241
  • /36

    $380,000 Coming Soon

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

    37 Underwood Rd, Woodstock, CT 06281

    Discover the charm and comfort of this beautiful 3 bedroom, one-bathroom home which was completely renovated in 2019! The renovation included a new furnace, hot water heater, electrical panel w/ generator hookup, roof and appliances! The remodel provides you a beautifully updated home with a cozy ambiance perfect in size for a small family or anyone downsizing. You will love the covered

    Belinda Culp Berkshire Hathaway NE Prop.

    37 Underwood Rd, Woodstock, CT 06281
  • /29

    $339,900

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    101 Shippee School House Rd, Danielson, CT 06239

    Great Ranch - Spacious 3 bedrooms and 2 baths. Large living room. Kitchen with eat-in dining with slider out to the deck. Many updates: Front door - New June 2023, Back door - New August 2020, Bathroom update 2019; added window, new flooring and painted. New insulation in attic March 2025, New Sump pump w/battery backup October 2024, New Dehumidifier October 2024, House fan added to attic in

    Sharon Fox Carl Guild & Associates

    101 Shippee School House Rd, Danielson, CT 06239
  • /22

    $350,000

    • 2 Beds
    • 1.5 Baths
    • 1,296 Sq Ft

    1534 Route 171, Woodstock Valley, CT 06282

    LOCATION, LOCATION! Right on Mass line and. Close to RI sits this PRIVATE COUNTRY CAPE on 5 ACRES! OVERSIZED 1 car garage (18 x 24) w/ attached breezeway w/ laundry room next to BRIGHT open appliance kitchen w/ BRAND NEW GRANITE counters, skylight for natural light in dining area leads to large 12 x 18 deck for entertaining. HARDWOOD floors in spacious living room w/ wood stove for second source

    Christine Johnson RE/MAX One

    1534 Route 171, Woodstock Valley, CT 06282
  • /39

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,482 Sq Ft

    163 State Ave, Dayville, CT 06241

    This charming home was thoughtfully remodeled in 2018 and recently updated again under new ownership. Enjoy a stunning brand-new kitchen featuring quartz countertops and all-new cabinetry complemented by modernized bathrooms. The flexible layout includes a convenient first-floor bedroom, two additional bedrooms upstairs, and a versatile bonus room-ideal for a home office or playroom. You'll love

    Tanya McDermott Berkshire Hathaway NE Prop.

    163 State Ave, Dayville, CT 06241
  • /3

    $349,500

    • Land
    • 1.14 Acres
    • $306,579 per Acre

    423 Providence Rd, Brooklyn, CT 06234

    * City Water, Septic, and Gas * Located across the street from Walmart Supercenter * Traffic Count: 14,900 * Conceptual Plans for Various Uses * Zoning Uses: Retail, Self Storage/Contractor Bays, Apartments/Condos * Zone: PC * Nearby Tenants: McDonald's, CVS, NAPA, Advance Auto Parts, Dollar Tree, Ocean State Job Lot, Dunkin', KFC, AutoZone, & (coming soon) Tractor Supply

    Sam Lyman Samuel Lyman, Broker

    423 Providence Rd, Brooklyn, CT 06234
  • /29

    $399,999

    • 8 Beds
    • 3 Baths
    • 2,782 Sq Ft

    36 Carter St, Danielson, CT 06239

    Wonderfully situated 3-family property in the heart of Danielson, ideal for both investors and owner-occupants. This versatile asset features a variety of unit sizes, offering flexibility and strong rental appeal. All three units are currently rented on a month-to-month basis, with long-term tenants in place ranging from 6 to 10 years-providing immediate income and potential for rental upside.

    Lexie Brunet Brunet and Company Real Estate

    36 Carter St, Danielson, CT 06239
  • /32

    $360,000

    • 3 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    12 John St, Danielson, CT 06239

    Welcome to your dream home, a beautifully renovated residence brimming with modern charm! This light-filled, airy home features an open-concept kitchen and dining area, perfect for entertaining. The gourmet kitchen boasts sleek granite countertops, a spacious island, and a breakfast bar. A convenient mudroom leads to the backyard and driveway, complete with a deck ideal for an above-ground pool.

    Nicholas Tomanelli Coldwell Banker Realty

    12 John St, Danielson, CT 06239
  • /27

    $325,000

    • 2 Beds
    • 1 Bath
    • 1,125 Sq Ft

    28 Oak Dr, Woodstock Valley, CT 06282

    LAKE LIFE IN WOODSTOCK. This charming year-round home in Woodstock, CT, offers a unique opportunity to embrace a peaceful lake lifestyle. Built in 1955, the residence sits on a generous 1.1-acre multi-tiered lot, providing ample privacy and seasonal lake views. KEY FEATURES: Deeded Beach Rights: Enjoy direct access to Bungee Lake with deeded beach rights, including access to association beaches

    Donna Copeland William Raveis Real Estate

    28 Oak Dr, Woodstock Valley, CT 06282
  • /16

    $350,000

    • 6 Beds
    • 2 Baths
    • 2,673 Sq Ft

    42 1st St Unit 44, Plainfield, CT 06374

    Well-maintained side-by-side duplex in the heart of Plainfield. This is an excellent opportunity for both investors and owner-occupants. Each spacious unit features 3 bedrooms, 1 full bath, an updated eat-in kitchen with wood cabinetry and stone countertops, and in-unit laundry hookups. Additional highlights include separate basements, separate utilities, and a detached garage for each unit.

    Kendra Bonette Coldwell Banker Realty

    42 1st St Unit 44, Plainfield, CT 06374
  • /39

    $350,000

    • 3 Beds
    • 1 Bath
    • 1,320 Sq Ft

    19 Thompson Pike, Dayville, CT 06241

    Highest & Best Offers: Wed. June 18 @ 5 pm. Welcome to 19 Thompson Pike in Killingly, where your ideal home awaits. Built in 2002, this inviting residence combines modern amenities with a cozy, welcoming atmosphere. Walk into an open floor plan filled with natural light, where the beautiful hardwood floors guide you through its inviting spaces. The kitchen is a chef's delight, featuring newer

    Kassi Mazzucco Compass Connecticut, LLC

    19 Thompson Pike, Dayville, CT 06241
  • /18

    $359,900

    • 3 Beds
    • 2 Baths
    • 1,732 Sq Ft

    552 Squaw Rock Rd, Moosup, CT 06354

    Private, set back from road, wooded 6+ acre lot with great views from rear deck and balcony off of primary bedroom! LARGE updated white kitchen with granite counters and appliances included, with dining area. LVP floors throughout first floor. First floor bedroom, full bath with jetted tub, separate shower & double sinks. Fpd living room that currently houses a stove (sold as is). Interior is

    Michelle Pivin Kazantzis Real Estate, LLC

    552 Squaw Rock Rd, Moosup, CT 06354
  • /37

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,807 Sq Ft

    42 Sycamore Terrace, Windham, CT 06280

    Nestled at the end of a quiet cul-de-sac, this beautifully maintained Cape-style home offers the perfect blend of privacy, comfort, and convenience. Boasting 3 spacious bedrooms, 2 full bathrooms, and an attached two-car garage, this property is thoughtfully designed to suit a variety of lifestyles. Step inside and discover an abundance of recent upgrades, including a brand-new architectural

    Stacey Silvia Lock and Key Realty, Inc

    42 Sycamore Terrace, Windham, CT 06280
  • /29

    $319,900 Open Sat 11AM - 12:30PM

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft

    34 Pleasant St, 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, Plainfield, CT 06374
  • /40

    $320,000

    • 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
  • /27

    $319,900 Open Sat 11AM - 12:30PM

    • 3 Beds
    • 1 Bath
    • 1,314 Sq Ft

    34 Pleasant St Unit 4, 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 4, Plainfield, CT 06374
  • /37

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,215 Sq Ft

    143 S Main St, Brooklyn, CT 06234

    Welcome to this spacious single-family home located in the charming town of Brooklyn, CT. Offering 3 generously sized bedrooms and 2 full bathrooms, this home features a bright and open layout with an abundance of natural light streaming through large windows. Beautiful hardwood flooring flows throughout, adding warmth and character. The modern kitchen is equipped with stainless steel appliances,

    Kyle Seyboth Century 21 Limitless

    143 S Main St, Brooklyn, CT 06234
  • /36

    $399,900 Open Sat 10AM - 12PM

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

    16 North Rd, Ashford, CT 06278

    Charming Antique Home with Timeless Beauty and Modern Comforts Step into the elegance of yesteryear with this beautifully maintained 3-bedroom, 2-bathroom antique home, where classic charm meets thoughtful updates and professionally landscaped surroundings. Nestled in a picturesque setting, this home welcomes you with warmth, character, and enduring appeal. Inside, you'll find sun-filled rooms,

    Kerri Mullen CR Premier Properties

    16 North Rd, Ashford, CT 06278
  • /13

    $330,000

    • 5 Beds
    • 2 Baths
    • 2,200 Sq Ft

    9 Ann St, Willimantic, CT 06226

    2 family house on a quiet street. First floor is a 2 bed 1 bath with hardwood floors throughout. Direct access to their side of the basement. Front foyer, eat in kitchen, living room. Second unit is the 2nd floor & 3rd floor and open, perfect for owner occupied multifamily. 2 bedrooms on the upper level with new carpet. Kitchen, dining room, living room, bathroom and 1 bedroom on the second floor

    david breau eXp Realty

    9 Ann St, Willimantic, CT 06226
  • /14

    $350,000

    • Land
    • 3.01 Acres
    • $116,279 per Acre

    199 Shippee Schoolhouse Rd, Killingly, CT 06241

    Start building your dream home right away on this stunning 3.01-acre property, fully prepared for you to hit the ground running. Approved, stamped building plans are ready to submit for permits, and trusted builders are lined up to begin - just add your final touches and you could be home by Christmas! The foundation is installed and painted, featuring a walkout basement with plumbing roughed in

    Jennifer Morton-Dumais LPT Realty - IConn Team

    199 Shippee Schoolhouse Rd, Killingly, CT 06241
  • /39

    $395,000

    • 3 Beds
    • 3 Baths
    • 1,728 Sq Ft

    23-25 Waterfall Rd, Ashford, CT 06278

    Welcome to 23-25 Waterfall Road! This oversized ranch, nestled on a 3.7 acre lot, boasts three bedrooms, three full baths, two wood burning fireplaces, a sun room, in-law suite, and a spacious attached garage. Additionally, this home comes equipped with a second two bay shop that includes ample storage and a vehicle lift. Other features of this home include a skylight overlooking the large eat-in

    Franchesca Pescatello Prue Realty LLC

    23-25 Waterfall Rd, Ashford, CT 06278
  • /23

    $385,000

    • 7 Beds
    • 4.5 Baths
    • 2,926 Sq Ft

    25-27 Farrows St, Putnam, CT 06260

    Invest in your next multi family. With the high demand for multi families, this oversized TWO family is set to be a money maker. Entire property has been properly updated and maintained for many years. Stable tenants in place with potential to increase rents in the future. Newer asphalt roofing, vinyl siding, updated interior units all make this property low maintenance for many years. The two

    Mark Tetreault, II RE/MAX Bell Park Realty

    25-27 Farrows St, Putnam, CT 06260
  • /37

    $399,999

    • 3 Beds
    • 1.5 Baths
    • 1,922 Sq Ft

    3 Woodstock Ave W, Putnam, CT 06260

    This character-filled home sits on a private and generous 1.39-acre lot-offering room to breathe, space to grow, and plenty of possibilities. With 1,922 square feet, this 3-bedroom, 1.5 bath residence is move-in ready and full of potential for the right buyer with vision and energy. Durable HardiePlank fiber cement siding wraps the home in timeless style and long-term protection-resisting

    Beth Fournier Compass Connecticut, LLC

    3 Woodstock Ave W, Putnam, CT 06260
  • /17

    $339,900

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

    360 N Society Rd, Canterbury, CT 06331

    Located in beautiful Canterbury, this large house is currently mostly gutted and waiting for you to complete. 2 car garage attached to house, and oversized 2 car garage workshop great for home business or car enthusiasts. Sold AS IS great for a handy man or flipper, its a great candidate for a 203K loan!

    Michelle Pivin Kazantzis Real Estate, LLC

    360 N Society Rd, Canterbury, CT 06331
  • /24

    $385,000

    • 3 Beds
    • 2 Baths
    • 2,034 Sq Ft

    105 Brick Top Rd, Windham, CT 06280

    Welcome to 105 Brick Top Rd.! Move right into this tastefully renovated home set on 1.49 acres of serene land. Step onto the beautifully updated porch, ready to be adorned with your personal touch. Inside, you'll be greeted by gorgeous, gleaming hardwood floors that flow throughout the main living spaces (excluding the bedrooms). The oversized foyer invites you into a desirable open floor plan,

    Maricela Rivera Coldwell Banker Realty

    105 Brick Top Rd, Windham, CT 06280
  • /20

    $310,000

    • 4 Beds
    • 2 Baths
    • 3,016 Sq Ft

    400 Main St, Danielson, CT 06239

    Unlock the potential of this spacious, well-maintained two-family property, perfect for both investors and owner-occupants! Each unit boasts over 1,500 sq. ft. of living space, featuring 2 bedrooms and 1 bath. The first-floor unit will be delivered empty, offering a prime opportunity for owner occupancy or market pricing, while the upstairs unit is currently rented month-to-month at $1,500/month.

    Brooke Packard Lamacchia Realty

    400 Main St, Danielson, CT 06239
  • /29

    $399,900

    • Land
    • 5 Acres
    • $76,904 per Acre

    1450 North Rd, Killingly, CT 06241

    This spectacular back lot down a private drive brings you into the wonder of nature. This expansive length of property has so much potential. With the land being previously cleared, it's ready for what you desire. The open space is unlimited from homesteading to possibly continuing the private airstrip rights to anything your dreams bring you. Make an appointment as this rare strip won't last

    Vicki McKee Spaulding Realty Group, LLC

    1450 North Rd, Killingly, CT 06241

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