Windham County CT Homes under $400,000

• 

  

  

  /23

  $330,000

  • 3 Beds
  • 1.5 Baths
  • 1,302 Sq Ft

  654 N Main St, Danielson, CT 06239

  Welcome to this beautifully refreshed New England home. Offering a blend of classic charm and modern updates, this property provides a warm and inviting setting both inside and out. Step inside to a bright, open interior featuring updated flooring, fresh finishes, and abundant natural light. The main living spaces flow seamlessly, including a comfortable living room and a dedicated dining area

  

  Ben Emerick

  Flagship Real Estate Advisors

  (860) 362-2982

  654 N Main St, Danielson, CT 06239
• 

  

  

  /29

  $325,000 New Construction

  • 1 Bed
  • 1.5 Baths
  • 1,167 Sq Ft

  7 Nahaco Hill Ln, Eastford, CT 06242

  Construction has started! Roof and siding going on 3rd week of April. Welcome to Nahaco Hills, a private, all ages community of 24 single family ranch homes. Step into bright, open-concept living filled with natural light and luxury vinyl plank floors throughout. The vaulted living room features a spacious storage closet and access to a composite deck, perfect for relaxing and enjoying the

  

  Valerie MacNeil

  Kazantzis Real Estate, LLC

  (860) 356-3831

  7 Nahaco Hill Ln, Eastford, CT 06242
• 

  

  

  /40

  $398,000 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,632 Sq Ft

  50 Old Sawmill Rd, Woodstock, CT 06281

  Set within the Bungee Lake community in Woodstock Valley, this home offers a comfortable layout with peaceful surroundings and water views. The property sits on a flat, open 0.6-acre lot, providing usable outdoor space for recreation, gatherings, or everyday enjoyment. This home offers 1,632 sq ft of living space with 3 bedrooms and 2 full bathrooms. The primary bedroom on the upper level

  Darius Baturo Berkshire Hathaway NE Prop.

  50 Old Sawmill Rd, Woodstock, CT 06281
• 

  

  

  /38

  $375,000

  • 2 Beds
  • 1.5 Baths
  • 864 Sq Ft

  70 Hawkins Rd, Woodstock Valley, CT 06282

  Welcome to this charming 2-bedroom, 1.5-bath home that offers the perfect blend of comfort and convenience. Ideal for empty nesters, downsizers, or anyone looking for a fantastic condo alternative, this home provides the privacy of single-family living without the hassle HOA. Step inside and enjoy a warm and inviting layout with comfortable living spaces that make the home feel instantly

  Joyce Teixeira Dream Living Realty, LLC

  70 Hawkins Rd, Woodstock Valley, CT 06282
• 

  

  

  /40

  $399,000

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft

  189 Wilsonville Rd, North Grosvenordale, CT 06255

  Set on a spacious half-acre lot and close to I-395, this updated Cape combines classic charm with flexible living space and extensive recent improvements. The main-level primary bedroom features a walk-in closet, while the remodeled upper level, completed in 2024, offers additional finished space ideal for a possible fourth bedroom and full bath setup. Recent updates include a new roof in 2024,

  Lauren Heidelberger Berkshire Hathaway NE Prop.

  189 Wilsonville Rd, North Grosvenordale, CT 06255
• 

  

  /14

  $400,000

  • 11 Beds
  • 2.5 Baths
  • 3,748 Sq Ft

  30 Main St, Plainfield, CT 06374

  Nestled in the heart of history, this extraordinary three-level estate exudes timeless elegance and vintage charm. With soaring ceilings, sprawling rooms, and intricate architectural details, this home captures the essence of a bygone era while offering the space and amenities for today's lifestyle. Every corner of this impressive residence tells a story-from the grand entryway with original

  Adam Gonzalez Century 21 Limitless

  30 Main St, Plainfield, CT 06374
• 

  

  /33

  $359,900

  • 2 Beds
  • 2 Baths
  • 1,643 Sq Ft

  45 Breaults Landing Rd, Thompson, CT 06277

  Water views and sunset skies come standard in this 1,643 sq ft 2-bedroom, 2-bath home overlooking Quaddick Lake with deeded water privileges. The primary suite features vaulted ceilings, a skylight, and beautiful lake views, creating a bright, airy space. A flexible loft area adds versatility for a variety of uses. The open concept main level offers a functional layout for both everyday living

  Christine Johnson RE/MAX One

  45 Breaults Landing Rd, Thompson, CT 06277
• 

  

  /40

  $365,000

  • 3 Beds
  • 1 Bath
  • 1,988 Sq Ft

  44 Ballamahack Rd, Windham, CT 06280

  *Sellers are reviewing offers in hand, but continuing to entertain offers at this time* A rare offering, this beautifully preserved circa 1766 Cape-style residence blends timeless New England character with thoughtful modern updates on just under 4 picturesque acres in Connecticut's Quiet Corner. Rich in historic detail, the home showcases wide plank floors, exposed hand-hewn beams, decorative

  Sue Esposito Home Selling Team

  44 Ballamahack Rd, Windham, CT 06280
• 

  

  /36

  $369,900

  • 3 Beds
  • 1 Bath
  • 1,266 Sq Ft

  44 Red Bridge Rd, North Grosvenordale, CT 06255

  Welcome to 44 Red Bridge Rd in Thompson, CT - a charming 3-bedroom, 1-bathroom home offering 1,266 square feet of comfortable living space in a convenient location across from a park and just minutes to town. This home blends everyday functionality with thoughtful touches that make it easy to enjoy both inside and out. The kitchen features quartz countertops and stainless steel appliances,

  Anthony La Penna Exceptional Real Estate LLC

  44 Red Bridge Rd, North Grosvenordale, CT 06255
• 

  

  /15

  $389,900

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  633 Wauregan Rd, Brooklyn, CT 06234

  2 full nice bathrooms and 3 bedrooms with one having access to fully finished and heated attic. Dining room could be used as a first floor bedroom with closet. New 4 bedroom septic installed.

  Ray Preece Signature Properties of N.E.

  633 Wauregan Rd, Brooklyn, CT 06234
• 

  

  /32

  $360,000

  • 3 Beds
  • 1.5 Baths
  • 1,517 Sq Ft

  143 Prospect St, Moosup, CT 06354

  Welcome to 143 Prospect St., Plainfield, CT-a beautifully updated turn-of-the-century home where classic charm meets modern comfort. The inviting wraparound porch provides a warm and welcoming first impression. Inside, the home has been beautifully renovated to suit today's lifestyle while preserving its original warmth and character. Rich hardwood floors run throughout, and energy-efficient

  Jennifer Mahr RE/MAX Bell Park Realty

  143 Prospect St, Moosup, CT 06354
• 

  

  /40

  $360,000

  • 3 Beds
  • 2 Baths
  • 2,244 Sq Ft

  379 Christian Hill Rd, Brooklyn, CT 06234

  Set back from the road, this charming Cape-style home offers 3 bedrooms, 2 full bathrooms, and 1,428 square feet of living space on 0.69 acres. Built in 2003, the home features a welcoming farmers porch, an easy-flow layout, and a fenced backyard with space to enjoy the outdoors. With a comfortable interior and peaceful setting, this property offers the best of country living while still being

  Tara Sepe HERE Realty

  379 Christian Hill Rd, Brooklyn, CT 06234
• 

  

  /23

  $359,900

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

  123 Ashford Rd Unit 1, Eastford, CT 06242

  Step into effortless modern living with this beautifully appointed 2-bedroom, 2-bath condo offering 1,500sqft of bright, open space. Built in 2019, this home blends contemporary style with everyday comfort, featuring rich hardwood floors, crisp finishes, and an inviting layout. The spacious kitchen is the heart of the home, complete with sleek cabinetry, stainless steel appliances, generous

  Benjamin Carbone Lamacchia Realty

  123 Ashford Rd Unit 1, Eastford, CT 06242
• 

  

  /20

  $350,000

  • 5 Beds
  • 2 Baths
  • 1,998 Sq Ft

  70 Walnut St, Putnam, CT 06260

  Charming Victorian 2-family set up high and framed by a classic stone wall, situated on a spacious .45-acre lot and fully occupied with strong cash flow from day one. Both tenants are in yearly leases, providing stability and consistent income, and each unit features separate utilities with individual boilers, with tenants paying their own heat and electric to help maximize returns. The

  Tyrone Murphy REMAX Revolution

  70 Walnut St, Putnam, CT 06260
• 

  

  /34

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,815 Sq Ft

  22 Westford Rd, Eastford, CT 06242

  A rare opportunity to own a piece of early New England history, this circa 1780 antique Cape is set in Eastford's quiet village setting, surrounded by open fields and timeless charm. Sited on nearly an acre with classic stone walls, this 3-bedroom, 2-bath home offers over 1800 square feet of character-filled living space. Original details include wide plank floors, exposed masonry, and multiple

  Robin Delaney Robin Delaney Real Estate

  22 Westford Rd, Eastford, CT 06242
• 

  

  /30

  $334,900

  • 2 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  74 Perry St Unit 183, Putnam, CT 06260

  Welcome to easy, low-maintenance condo living in the heart of Putnam! This well-appointed 2-bedroom, 1.5-bath home offers a bright and inviting main level featuring a sun-filled living room with beautiful hardwood floors and direct access to a private wood deck-perfect for seamless indoor/outdoor living. The kitchen is designed for both function and comfort, complete with a dining area, pantry

  Genevieve Botelho Lamacchia Realty

  74 Perry St Unit 183, Putnam, CT 06260
• 

  /2

  $400,000

  • Land
  • 3.2 Acres
  • $125,000 per Acre

  0 Putnam Rd Unit 24147722, Plainfield, CT 06332

  3.2 corner lot located at the Wauregan four corners. Currently zoned residential but has commercial potential. Buyer's and buyers agent to do all of your own due diligence with the town.

  Cary Marcoux RE/MAX Bell Park Realty

  0 Putnam Rd Unit 24147722, Plainfield, CT 06332
• 

  

  /6

  $309,900

  • Land
  • 45 Acres
  • $6,887 per Acre

  0 Cook Hill Rd Unit 24135933, Killingly, CT 06239

  Do not miss out on the opportunity to own 45 acres in Killingly! Nestled along rural Cook Hill Rd, this stunning lot offers privacy and convenience. This raw classic New England land offers beautiful mature trees, stone walls, and a small stream. Convenient location just minutes away from i395, Route 6, shopping plazas, restaurants, and convenience stores. Come explore the endless opportunities

  Joseph Bonneau eXp Realty

  0 Cook Hill Rd Unit 24135933, Killingly, CT 06239
• 

  

  /40

  $305,000

  • 3 Beds
  • 1.5 Baths
  • 1,640 Sq Ft

  1250 Route 171, Woodstock, CT 06281

  Welcome to this charming colonial with stenciled details that add character & style! This delightful antique property is the perfect fixer upper and features 3 bedrooms, 1 and a 1/2 bathrooms, and a clapboard exterior. Situated on a 0.9 acre lot, this home boasts a garden in the side yard and a large backyard, perfect for outdoor enjoyment. Additionally, a shed provides convenient storage for

  Kara Mazzola First Choice Realty

  1250 Route 171, Woodstock, CT 06281
• 

  

  /15

  $349,000

  • 4 Beds
  • 2 Baths
  • 2,219 Sq Ft

  24 Day St, Brooklyn, CT 06234

  Desirable Brooklyn Location...Cape Style home with 2169sqft, 4 bed, 2 Full Baths on 2.78 Ac of land. NEW ROOF will be done next week. Spacious Open floor plan with NEWER GRANITE KITCHEN and Living rm completely open. Granite countertops w/ Built in sink & soft close cabinets w/ all SS appliances. HUGE GRANITE ISLAND w/built in Gas stove. Slider to your oversized porch over looking your private

  Irene Adams Signature Properties of N.E.

  24 Day St, Brooklyn, CT 06234
• 

  

  /18

  $329,000

  • 3 Beds
  • 1.5 Baths
  • 1,606 Sq Ft

  279 River Rd, Putnam, CT 06260

  Opportunity and character come together in this 1840 home set on 2.03 acres in Putnam. Rich with charm, the home features wide board flooring, built-ins in both the living and dining rooms, and butcher block countertops that bring warmth to the space. The layout includes a quarter bath on the main level and three bedrooms with a full bath upstairs. A spacious enclosed breezeway creates a flexible

  Scott Pempek Berkshire Hathaway NE Prop.

  279 River Rd, Putnam, CT 06260
• 

  /2

  $335,000

  • Land
  • 62.27 Acres
  • $5,380 per Acre

  0 Scotland Rd Unit 24160798, Chaplin, CT 06235

  **Builders Take Notice** This is a beautiful 62.273 acres with subdivision opportunities. A-2 Survey is available. Owner financing is available.

  Sherry Borgeson Berkshire Hathaway NE Prop.

  0 Scotland Rd Unit 24160798, Chaplin, CT 06235
• 

  /2

  $335,000

  • Land
  • 34.6 Acres
  • $9,682 per Acre

  0 Route 171, Woodstock, CT 06281

  Spanning just over 37 acres this raw land parcel offers a picturesque pond and a wooded landscape, creating a versatile setting with a variety of potential uses. A rare opportunity to own a large tract of land in a lovely location.

  Nicole Gleason CR Premier Properties

  0 Route 171, Woodstock, CT 06281
• 

  

  /40

  $325,000

  • 5 Beds
  • 2.5 Baths
  • 2,781 Sq Ft

  125 Mountain St, Willimantic, CT 06226

  Investors take notice! This home is a money maker. Whether you decide to owner-occupy this spacious home while rental income helps with the mortgage, or rent out both units, you can't go wrong. The living areas provide warm spaces perfect for relaxing or gathering with friends and family. The kitchens offer ample cabinet and counter space, making everyday cooking convenient and enjoyable. The

  Lisa Antrum KW Legacy Partners

  125 Mountain St, Willimantic, CT 06226
• 

  

  /35

  $384,900

  • 3 Beds
  • 2.5 Baths
  • 1,470 Sq Ft

  49 Fremont St, Putnam, CT 06260

  Nothing to do but move in to this fully turnkey young Colonial in a highly convenient Putnam location! Offering 1470 SF, 3 bedrooms & 2.5 baths, this home stands out for its incredible condition and thoughtful updates. The inviting farmer's porch adds charm, while inside you'll find fresh carpet, a fully repainted interior, new vinyl kitchen flooring, hardwood throughout the remainder of the 1st

  Jared Meehan RE/MAX Bell Park Realty

  49 Fremont St, Putnam, CT 06260
• 

  /2

  $300,000

  • Land
  • 8.8 Acres
  • $34,091 per Acre

  100 Hubbard Hill Rd, Killingly, CT 06239

  Experience the quintessential beauty of this New England countryside on this breathtaking 8.8 acres. This property offers a rare sense of pastoral peace without sacrificing convenience. Located less than a quarter-mile from I-395, you can enjoy a quiet, rural lifestyle with seamless transit to Boston, Providence, and NYC right at your doorstep. This is also listed as part of 4 properties which

  Jill Pilgrim William Pitt Sotheby's Int'l

  100 Hubbard Hill Rd, Killingly, CT 06239
• 

  /2

  $399,900

  • Land
  • 8.29 Acres
  • $48,239 per Acre

  0 West Pkwy, Plainfield, CT 06374

  Positioned within a well-established industrial park, this 8+ acre parcel offers a prime opportunity for industrial development just 1/2 mile from Interstate 395, providing excellent regional access for transportation, logistics, and distribution operations. The property's location allows for efficient connectivity to major Northeast markets, making it ideal for manufacturing, warehousing,

  Androula Kazantzis KAZANTZIS ANDROULA

  0 West Pkwy, Plainfield, CT 06374
• 

  /2

  $400,000 New Construction

  • 1 Bed
  • 1 Bath
  • 644 Sq Ft

  6 Indian Run Dr, Thompson, CT 06277

  Similar to be built. Charming Craftsman-style home offering efficient, low-maintenance living! This thoughtfully designed 644 sq. ft. home features 1 bedroom and 1 full bathroom with a bright, open floor plan. Large windows fill the space with natural sunlight, creating a warm and inviting atmosphere. The kitchen and living areas flow seamlessly, perfect for comfortable everyday living. Enjoy

  Cary Marcoux RE/MAX Bell Park Realty

  6 Indian Run Dr, Thompson, CT 06277
• 

  

  /40

  $375,000

  • 6 Beds
  • 2 Baths
  • 2,727 Sq Ft

  5 8th St, Plainfield, CT 06374

  Owner-occupied duplex ready for its next chapter! This well-maintained property features two spacious units, each offering 3 bedrooms and 1 full bath. Ideal for both owner-occupants and investors, with strong income potential or the option to live in one unit while renting the other. Conveniently located close to town and a nearby park, providing easy access to everyday amenities. A solid

  Cary Marcoux RE/MAX Bell Park Realty

  5 8th St, Plainfield, CT 06374
• 

  

  /30

  $350,000

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  490 Kate Downing Rd, Plainfield, CT 06374

  *HIGHEST AND BEST DEADLINE MONDAY 4/27 at 5PM!* Well-loved and thoughtfully maintained raised ranch set in a desirable location, offering comfort, space, and a beautiful setting. This 3-bedroom, 1 full bath home features an open-concept layout with a seamless flow between the kitchen, dining, and living areas-ideal for everyday living and entertaining. The spacious kitchen offers ample cabinetry

  Skyla Gagnon RE/MAX Bell Park Realty

  490 Kate Downing Rd, Plainfield, CT 06374
• 

  

  /39

  $399,900

  • 3 Beds
  • 2.5 Baths
  • 2,123 Sq Ft

  1 Library Rd, Canterbury, CT 06331

  Welcome to 1 Library Road, a beautifully updated antique Colonial nestled in the heart of Canterbury's Historic District. Built circa 1807, this classic home combines historic charm with modern improvements on a generous 1.15-acre corner lot just steps from the Canterbury Center Historic District and village green, which features fine 18th- and early 19th-century architecture and cultural

  Kristopher Tramont Real Broker CT, LLC

  1 Library Rd, Canterbury, CT 06331
• 

  

  /37

  $325,000

  • 3 Beds
  • 2.5 Baths
  • 1,228 Sq Ft

  15 Cracow Ave, Windham, CT 06280

  Welcome to this inviting 3-bedroom, 2-bath ranch featuring a 1-car garage and a fantastic layout perfect for comfortable everyday living. Placed right along side the Natchaug River used for fishing and kayaking! Step inside to find a bright, open floor plan with warm natural light and easy flow throughout. Outside, the property truly shines. Enjoy summer days in your beautiful inground pool (with

  Julienne Jaber KW Legacy Partners

  15 Cracow Ave, Windham, CT 06280
• 

  

  /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
• 

  

  /10

  $330,000

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

  Unlisted Address

  Multi family opportunity! Updates made. Walk out basement storage and off street parking. Separate utilities. Conveniently located to major routes and shopping!

  Amy Brunet Brunet and Company Real Estate

  Unlisted Address
• 

  

  /40

  $389,900

  • 3 Beds
  • 2.5 Baths
  • 2,820 Sq Ft

  609 Norwich Rd, Plainfield, CT 06374

  Welcome to 609 Norwich Road in Plainfield-a well-maintained and move-in ready home offering comfort, space, and convenience. This property features a bright and functional layout with generously sized rooms, updated flooring, and plenty of natural light throughout. The kitchen offers ample cabinet and counter space, perfect for everyday living and entertaining alike. Upstairs and living areas

  Victor Santana Santana Realty Group LLC

  609 Norwich Rd, Plainfield, CT 06374
• 

  

  /32

  $309,999

  • 3 Beds
  • 1 Bath
  • 924 Sq Ft

  20 Toleration Rd, Baltic, CT 06330

  Welcome to beautiful Scotland-where peace, tranquility, and small-town living are both cherished and preserved. This small yet mighty Cape-style home offers surprising space and comfort. The main floor features an updated eat-in kitchen and a cozy living room complete with a fireplace. Down the hall, you'll find the primary bedroom, a full bath, and a charming library with built-ins that can

  Daniele Killen Remax Host of Homes

  20 Toleration Rd, Baltic, CT 06330
• 

  

  /3

  $339,900 Open Thu 5PM - 6:30PM

  • 5 Beds
  • 2 Baths
  • 1,602 Sq Ft

  59-61 Gallup St, Plainfield, CT 06374

  Spacious multi-family duplex located in the desirable Plainfield Village area! This well-maintained property features two units-one side offers 3 bedrooms and 1 full bathroom, while the other includes 2 bedrooms and 1 full bathroom-perfect for owner-occupants or investors. Both units come equipped with laundry hookups and separate driveways, providing added convenience and privacy for tenants.

  Nicole Cournoyer RE/MAX Bell Park Realty

  59-61 Gallup St, Plainfield, CT 06374
• 

  

  /28

  $324,900

  • 4 Beds
  • 1 Bath
  • 1,152 Sq Ft

  21 Russ Rd, Willimantic, CT 06226

  Welcome to this beautifully presented 4bedroom Cape-style home on a generous lot - an entertainer's dream and a peaceful everyday retreat. Inside, gleaming hardwood floors and abundant natural light flow through an open, thoughtfully updated interior. The kitchen shines with stunning new cabinetry, granite countertops, a stylish backsplash and stainless steel appliances - perfect for casual meals

  Ryan Newport Social & Co Realty

  21 Russ Rd, Willimantic, CT 06226
• 

  

  /20

  $335,000

  • 2 Beds
  • 1.5 Baths
  • 1,348 Sq Ft

  297 Sabin St Unit 1, Putnam, CT 06260

  Desirable end unit Townhouse in the lovely Sabin Landing. This unit offers 2 generous size bedrooms, 1.5 baths a full basement plus one car garage. This updated unit has a great open Kitchen/Living Room /Dining Area on the main level. Gas Heat, Central A/C and a cozy gas fireplace in the living room. Slider to your rear deck and plenty of guest parking.

  Amy Brunet Brunet and Company Real Estate

  297 Sabin St Unit 1, Putnam, CT 06260
• 

  

  /27

  $369,000 Coming Soon

  • 5 Beds
  • 2 Baths
  • 2,284 Sq Ft

  14 Spring St, Danielson, CT 06239

  Killingly...Beautiful 2 Family With Side By Side TownHouse Style large Units. 1st unit is 1184sqft, 6rms, 3bedrms, full Bath. Spacious unit with open living & dining rm w/ lots of windows for plenty of sunlight & hardwd floors.Gorgeous kitchen w/soft close cabinets, GRANTIE counters, built in sink, SS appliances including a dishwasher & water resistant flooring. Large Master suite w/walkin closet

  Irene Adams Signature Properties of N.E.

  14 Spring St, Danielson, CT 06239

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