Homes for Sale near Windham Middle School

• 

  

  

  /40

  $650,000 Open Sat 12PM - 4PM

  • 4 Beds
  • 2 Baths
  • 2,190 Sq Ft

  156 Ballamahack Rd, Windham, CT 06280

  Who says you can't have it all? Do not miss this rare and fully equipped horse property set on over 26 private acres in rural Connecticut. This versatile estate offers everything needed for a working farm, peaceful retreat, or unbeatable event space. Your home is a 2190sqft, 4-bedroom, 2-bath home with a first-floor primary suite, a warm rustic dining room, and a flexible bonus room for an

  

  Stephen Daly

  LPT Realty

  (860) 750-8672

  156 Ballamahack Rd, Windham, CT 06280
• 

  

  

  /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
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  /9

  $99,900

  • Land
  • 1.10 Acres
  • $90,818 per Acre

  38 Elm St, Willimantic, CT 06226

  1.1 Acre Commercial Lot - B3 Zoned - Great Opportunity in Willimantic! Lot Size: 1.1 Acres Zoning: B3 - Business District Access: Deeded easement via Family Dollar and Elm Street. Don't miss this unique opportunity to own a 1.1-acre level commercial lot tucked just off Main Street in Willimantic. Located directly behind Family Dollar, this parcel offers convenient access via a recorded easement,

  

  Tammy Lucier

  eXp Realty

  (860) 979-5391

  38 Elm St, Willimantic, CT 06226
• 

  

  

  /29

  $179,925

  • 7 Beds
  • 3 Baths
  • 2,668 Sq Ft

  57 Chapman St, Willimantic, CT 06226

  Don't miss this exceptional investment opportunity at 57 Chapman Street in Willimantic, CT! This versatile 3-family property features one spacious 3-bedroom, 1-bath unit and two well-proportioned 2-bedroom, 1-bath units, making it an ideal choice for investors or owner-occupants seeking rental income. Each unit offers comfortable layouts with ample potential for updates and customization,

  

  Jason Kemp

  Five Stars Realty

  (860) 419-7674

  57 Chapman St, Willimantic, CT 06226
• 

  

  /24

  $459,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  1145 Windham Rd, Windham, CT 06266

  COMPLETED AND READY TO MOVE IN. Brand new construction!! Wonderful floor plan, with a large and open area encompassing the kitchen, dining and living room areas. Tons of natural light coming from windows, and sliders in dining area. Main level includes a flex room, and a half bath. Upstairs you will find the three bedrooms, including a primary with its own full bath and walk in closet, as well as

  Timothy Morse Home Selling Team

  1145 Windham Rd, Windham, CT 06266
• 

  

  /21

  $318,965 Open Sat 12PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft

  195 Quarry St, Willimantic, CT 06226

  Check out this move-in ready 3 bed, 2 full bath Ranch! This lovingly renovated home features a finished walk-out basement with in-law potential, separate entry, and kitchen water hookups including brand new plumbing w/ toilet and vanity. Highlights include granite countertops, a brand new boiler, new and a like-new (1-year-old) pool pump and filter. The only home on Quarry with a spacious front

  Jasmine Baker RE/MAX One

  195 Quarry St, Willimantic, CT 06226
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  /40

  $389,900 Open Sat 9AM - 11AM

  • 3 Beds
  • 2.5 Baths
  • 1,691 Sq Ft

  65 Anna Maria Ln, Windham, CT 06280

  Welcome to this well-maintained 3-bedroom, 3-bathroom Cape nestled on a peaceful cul-de-sac in a desirable, family-friendly neighborhood. This home offers the perfect blend of comfort and functionality with an open floor plan, spacious rooms, and thoughtful updates throughout. The main level features a sunlit kitchen with granite countertops that flows seamlessly into the dining area and living

  Kristen Merrill Countryside Realty

  65 Anna Maria Ln, Windham, CT 06280
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  /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
• 

  

  /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
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  /38

  $437,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 2.5 Baths
  • 2,905 Sq Ft

  337 S Windham Rd, Willimantic, CT 06226

  Step into timeless elegance with this beautifully renovated 1850 Colonial, now featuring a brand new septic tank and central A/C system installed in April 2025-a perfect blend of historic charm and modern comfort. Nestled in the heart of Windham, this stunning 9-room home has 4 spacious bedrooms and 2.1 bathrooms, providing ample space for today's lifestyle. Inside, you'll find brand-new kitchens

  Alexia Andrade US Asset Realty

  337 S Windham Rd, Willimantic, CT 06226
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  /8

  $430,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,792 Sq Ft

  7 Autumn Ridge, Windham, CT 06280

  Beautiful Custom Colonial To Be Built on 1.81 Acre Level Lot!

  Cathyann Schulte Countryside Realty

  7 Autumn Ridge, Windham, CT 06280
• 

  

  /12

  $441,750 New Construction

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  1157 Windham Rd, Windham, CT 06266

  New Raised Ranch Close to completion. Nice Lay out with 3 bedrooms, including a primary suite with walk in closet, and its own full bath. Main level kitchen, dining, and living room, all flow together as one large open space. This open living area area also separates the the bedrooms, with the primary suite on one side, and the two other bedrooms, and a full bath on the other. Lower level has a

  Timothy Morse Home Selling Team

  1157 Windham Rd, Windham, CT 06266
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  /39

  $315,000 Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,284 Sq Ft

  106 Oxbow Dr, Willimantic, CT 06226

  Need more space..this is the house for you, over 1200 sq ft raised ranch. The main level has a 19x23 Living room with hardwood floor, built ins, a ceiling fan and sliders going out to a 19x20 deck. The dining room also has a ceiling fan and a breakfast bar accessing the Kitchen. Lots of cabinets, counter space and tile floor makes the kitchen very appealing. A full bath with Tub/shower and 2

  Sondra Reid Home Selling Team

  106 Oxbow Dr, Willimantic, CT 06226
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  /2

  $340,000 Coming Soon

  • 4 Beds
  • 1.5 Baths
  • 2,383 Sq Ft

  39 Windham Center Rd, Windham, CT 06280

  Welcome home! Charming colonial located in historic district in Windham County. Main floor consists of four bedrooms, one full bathroom, laundry area, and bonus room/office/den. Large living area with built in shelving. All four bedrooms located on upper level with additional full bathroom. Outside boasts patio area surrounded by young Rose of Sharon. Detached three bay garages with automatic

  Katrina Gulowsen On The Move Realty, LLC

  39 Windham Center Rd, Windham, CT 06280
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  /31

  $263,200 Open Sat 12PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,170 Sq Ft

  65 Hewitt St, Willimantic, CT 06226

  Charming 3 bedroom cape in the hill section of Willimantic. This home has been lovingly maintained and is ready for you to move in. With hardwood floors throughout, a fireplace and a much sought after first floor bedroom, you will be central to many amenities. The one car garage and lovely yard complete the package.

  Ellen Mott Berkshire Hathaway NE Prop.

  65 Hewitt St, Willimantic, CT 06226
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  /34

  $290,000

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft

  44 Woodland Dr, Windham, CT 06280

  Opportunity awaits in this spacious ranch-style home offering the ease of one-level living! Featuring 3 bedrooms and 2 full baths, including one in the partially finished basement, this home is full of potential. Bring your vision and make your custom updates to truly make it your own. Enjoy a bright layout with replacement windows throughout, a level yard perfect for outdoor living, and the

  Kelley Vanacore Century 21 AllPoints Realty

  44 Woodland Dr, Windham, CT 06280
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  /36

  $489,999

  • 12 Beds
  • 4 Baths
  • 2,750 Sq Ft

  251 Jackson St, Willimantic, CT 06226

  INVESTORS take NOTE! Turnkey 4-Unit Investment Property with room for upside. This opportunity to own a well-maintained multi-family in the LOW VACANCY market of Windham wont last long! Updated utilities, separate meters, and reliable long-term tenants. All utilities separately metered. MANY upgrades including a complete remodel making this property suitable for owner occupant or investor. On the

  Robyn Letourneau Berkshire Hathaway NE Prop.

  251 Jackson St, Willimantic, CT 06226
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  /17

  $299,900

  • 4 Beds
  • 2.5 Baths
  • 1,609 Sq Ft

  60 Impala Dr, Willimantic, CT 06226

  WELCOME TO 60 IMPALA DRIVE!! THIS WELL MAINTAINED HOME IN A QUIET NEIGHBORHOOD WITH CLOSENESS TO STORES, RESTAURANTS, SCHOOLS AND PLAYGROUNDS. THIS HOME HAS BEEN UPDATED IN THE LAST 8 YEARS WITH THE MUCH NEEDED FURNACE, OIL TANK, HOT WATER HEATER, ELECTRICAL PANEL, AND PLUMBING. THE HOME WAS ALSO PAINTED IN AND OUT AND ENJOYED BY THE FAMILY FOR THE LAST FEW YEARS. A FULLY APPLIANCED KITCHEN WITH

  Jackie Lovett William Raveis Real Estate

  60 Impala Dr, Willimantic, CT 06226
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  /35

  $599,999

  • 12 Beds
  • 5 Baths
  • 4,466 Sq Ft

  136 Chapman St, Windham, CT 06226

  INVESTORS TAKE NOTE!! LOW VACANCY in Windham county. 5-unit Investment Property with Strong Cash Flow! Located in the heart of Willimantic, this fully occupied property offers easy maintenance, off street parking, and stable tenants. GOI: $82,560 Other income: $2400 Expenses: $71,628 NOI: $71,628 12 CAP Combine with other listed willimantic properties: Elm st., Jackson St., and Pleasant St. as a

  Robyn Letourneau Berkshire Hathaway NE Prop.

  136 Chapman St, Windham, CT 06226
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  /36

  $289,900

  • 2 Beds
  • 1 Bath
  • 1,155 Sq Ft

  86 Whittemore St, Willimantic, CT 06226

  Step into your own slice of paradise with this immaculate and beautifully maintained home, offering comfort, character and convenience. Nestled on a generous lot with a large side yard, this property welcomes you with a charming front porch and a cozy side entry porch-perfect for morning coffee or evening gatherings. Inside, enjoy an open and flowing layout featuring a bright kitchen, inviting

  Sheri Shvonski List N Show LLC

  86 Whittemore St, Willimantic, CT 06226
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  /28

  $269,900

  • 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
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  /40

  $515,000

  • 8 Beds
  • 3.5 Baths
  • 5,134 Sq Ft

  4 Main St, Willimantic, CT 06226

  Terrific Investment Opportunity! Don't miss this rare chance to own a well-maintained multi-unit property with strong income potential. The main house features a spacious layout with 5 bedrooms, ideal for large households or rental flexibility. Behind the main home, you'll find a separate 2-bedroom unit, perfect for extended family or additional rental income. Additionally, there's a third unit-a

  Tammy Arute Arute Realty Group LLC

  4 Main St, Willimantic, CT 06226
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  /32

  $125,000

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

  8 Haley Ln, North Windham, CT 06256

  Spacious 3-Bedroom Home in Stonegate Manor!! This well-maintained 3-bedroom, 2-bath mobile home offers 1,296 square feet of comfortable living in the desirable Stonegate Manor community. Built in 2003, it features a functional layout with generous room sizes, a solid structure, and excellent potential for customization. Conveniently located in Windham, you're just minutes from shopping, dining,

  Jason Boice eXp Realty

  8 Haley Ln, North Windham, CT 06256
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  /29

  $245,000

  • 4 Beds
  • 1.5 Baths
  • 1,621 Sq Ft

  67 North Rd, Windham, CT 06280

  Discover the charm of 67 North Road, a captivating four-bedroom, one-and-a-half-bathroom home full of character. Constructed in the 1850s, this historic gem is nestled in the quaint Historic District of Windham Center. With its prime location just off of Route 203 and Route 14, your daily commute to major highways is effortless. This property presents the opportunity for those with a vision,

  Franchesca Pescatello Prue Realty LLC

  67 North Rd, Windham, CT 06280
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  /29

  $78,000

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  60 Lions Way, North Windham, CT 06256

  Move in ready, clean and beautiful 2 bedroom mobile home.This home boosts a Living room with a celing fan and lots of sunshine. A large eat in kitchen with new lights and lots of cabinets. Primary suite with a full bath and ceiling fan. At the other end is another bedroom with a full bath. Laundry room/mudroom with back door. Outside is a large porch, shed and garden. Very well maintained and a

  Sondra Reid Home Selling Team

  60 Lions Way, North Windham, CT 06256
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  /26

  $59,900

  • 2 Beds
  • 1 Bath
  • 844 Sq Ft

  51 James Dr, North Windham, CT 06256

  Charming 2 bedroom Mobile Home in peaceful Stonegate Manor Windham. Discover comfort and convenience in this well maintained 2 bedroom 1 bath mobile home nestled in the heart of Windham. Perfectly designed for easy living, this home features a cozy living space, a dedicated laundry room and a bright, functional layout. Step outside to enjoy a lovely garden area ideal for relaxing or gardening

  Nancy Bard Bard Real Estate, LLC

  51 James Dr, North Windham, CT 06256
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  /29

  $259,900

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft

  16 Gem Dr, Willimantic, CT 06226

  Well maintained Charming Ranch w/ Oversized-TANDEM 2 CAR GARAGE w/Additional Storage Space with short, convenient commute to both Eastern Connecticut State University and University of Connecticut, * CAIR * Refinished Hardwood Floors & Fresh Paint throughout * Sliders to Deck overlooking nice sized yard w/Shed * Quiet Neighborhood Setting * Walkout Basement can be finished easy for additional

  Kimberly Gates Gateway Real Estate

  16 Gem Dr, Willimantic, CT 06226
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  /14

  $220,000

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft

  78 Lauter Ave, Willimantic, CT 06226

  Welcome to this inviting single-family ranch located in a quiet neighborhood just minutes from downtown Willimantic! This well-maintained 3-bedroom, 1-bath home offers comfort, convenience, and classic New England charm-perfect for first-time buyers, downsizers, or anyone seeking one-level living. Convenient to Eastern Connecticut State University (ECSU) and UConn, Close to local parks,

  Jenny Adamo KW Legacy Partners

  78 Lauter Ave, Willimantic, CT 06226
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  /18

  $69,900

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  26 Jacqueline Ln, North Windham, CT 06256

  Two bed, two full bath, recently remodeled home with large deck in a less traveled area of Stonegate Manor. Great affordable price point in a well maintained community. Laundry hook ups of the kitchen area and plenty of off street parking. Come and view this great unit before it's gone! Closing cost assistance available.

  Derek Greene Derek Greene

  26 Jacqueline Ln, North Windham, CT 06256
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  /15

  $112,000

  • 2 Beds
  • 1 Bath
  • 790 Sq Ft

  270 S Windham Rd Unit 61, Willimantic, CT 06226

  Welcome to this beautifully remodeled 2-bedroom, 1-bath condo nestled in a quiet, well-maintained community in Windham, CT. This turn-key unit offers a perfect blend of modern updates and low-maintenance living-ideal for first-time buyers, downsizers, or investors. Step inside to discover a bright and airy open-concept living and dining area, freshly painted in neutral tones. The spacious primary

  Jenny Adamo KW Legacy Partners

  270 S Windham Rd Unit 61, Willimantic, CT 06226
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  /24

  $66,000

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  31 James Dr, North Windham, CT 06256

  If financing, use appropriate lender, listing agent has more info. Welcome to 31 James Dr, a cute and quaint mobile home nestled in a peaceful community near the Windham Airport. This delightful residence offers 2 comfortable bedrooms and 1 beautifully updated bathroom, all within a cozy 924 sq ft of living space. Step inside to discover a home that has been thoughtfully updated in recent years.

  Brandon Cramer KW Legacy Partners

  31 James Dr, North Windham, CT 06256
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  /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
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  /20

  $55,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  36 Fairway Dr, Windham, CT 06256

  2 Bed, 1 Bath Mobile home located in the Country Club Estates Mobile Home Park. Desirable community close to many recreational, shopping, and dining options. This home is waiting to be loved by its next owner. Home being sold in as is condition. All buyers are subject to park approval.

  Erica Molochnick RbRE, LLC

  36 Fairway Dr, Windham, CT 06256
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  /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
• 

  

  /19

  $245,000

  • 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
• 

  

  /40

  $290,000

  • 3 Beds
  • 3 Baths
  • 2,382 Sq Ft

  269 Jackson St, Willimantic, CT 06226

  Welcome to a rare opportunity for both savvy investors and future owner-occupants alike. This Colonial-style three-family home offers the ideal blend of character, functionality, and strong income potential. Whether you're looking to offset your mortgage with tenant income or expand your investment portfolio, this property is a smart choice. The owner's unit will be delivered vacant and features

  Michael A Tarallo Giner Real Estate

  269 Jackson St, Willimantic, CT 06226
• 

  

  /21

  $79,900

  • 3 Beds
  • 1.5 Baths
  • 924 Sq Ft

  11 Elizabeth Ln, North Windham, CT 06256

  Affordable & Move-In Ready! Welcome to 11 Elizabeth Lane- A beautifully updated 3-bedroom, 1.5-bath home in the quiet Stonegate Manor community. With 924 sq. ft. of easy-living space, it's perfect for first-time buyers, downsizers, or anyone looking for low-maintenance comfort. Enjoy a bright, eat-in kitchen with a skylight, breakfast bar, and all major appliances included. The open living/dining

  Rebecca Zager The Agency

  11 Elizabeth Ln, North Windham, CT 06256
• 

  

  /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
• 

  

  /33

  $89,900

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

  57 Circle Dr, Windham, CT 06256

  Welcome to 57 Circle Drive in North Windham! This charming 1,152 sq ft manufactured home features comfortable living with 3 spacious bedrooms and 2 full bathrooms. The property offers ample outdoor space for relaxation or play. Recent upgrades include a new roof (2024 - $4,000), a new water heater (2024 - $1,500), and repaired skirting (2024 - $500), ensuring peace of mind for the new owner.

  Jessica Boswell LPT Realty

  57 Circle Dr, Windham, CT 06256

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