35

Homes for Sale near Windham High School

Section Image Section Image
  • /40

    $650,000

    • 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

    Agent Photo

    Stephen Daly

    LPT Realty

    (860) 750-8672

    156 Ballamahack Rd, Windham, CT 06280
  • /9

    $84,900

    • Land
    • 1.10 Acres
    • $77,182 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,

    Agent Photo

    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,

    Agent Photo

    Jason Kemp

    Five Stars Realty

    (860) 419-7674

    57 Chapman St, Willimantic, CT 06226
  • /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,

    Agent Photo

    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

    Agent Photo

    Amber Jones

    KW Legacy Partners

    (860) 791-3791

    96 South St, Willimantic, CT 06226
  • /2

    $335,000 Coming Soon

    • 6 Beds
    • 3.5 Baths
    • 3,274 Sq Ft

    384 Prospect St, Willimantic, CT 06226

    Charming Victorian Home in the Heart of the Hill Section - Just Steps from ECSU This beautifully crafted Victorian residence offers over 3,000 sq ft of living space and is conveniently located near the entrance of Eastern Connecticut State University. Featuring a spacious chef's kitchen, an inviting front porch, and a covered back porch perfect for relaxing or entertaining. Inside, you'll find a

    Agent Photo

    Heather Meehan

    Meehan & Daughters Real Estate

    (860) 321-1528

    384 Prospect St, Willimantic, CT 06226
  • /15

    $385,000

    • 3 Beds
    • 1.5 Baths
    • 1,712 Sq Ft

    41 Jennings Ln, Windham, CT 06280

    Welcome to this beautifully maintained raised ranch nestled on a meticulously landscaped lot-offering exceptional curb appeal and plenty of space for outdoor entertaining. The oversized front, side, and backyard areas, along with the long, wide paved driveway and ample parking, provide the perfect setting for hosting family and friends. Inside, enjoy a bright and open floor plan featuring 3

    Sheri Shvonski List N Show LLC

    41 Jennings Ln, Windham, CT 06280
  • /39

    $339,900 Open Sun 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 1,190 Sq Ft

    157 Scotland Rd, Windham, CT 06280

    Scenic and spacious, this charming 3-bedroom, 2.5-bath home sits on just under an acre along a country road-offering the perfect blend of privacy and convenience. Inside, you'll find a well-designed living space, featuring a functional layout and thoughtful upgrades including brand-new PEX plumbing and an energy-efficient heat pump for year-round comfort. The heart of the property is the

    Josh Bodian Evermark Property Group

    157 Scotland Rd, Windham, CT 06280
  • /36

    $335,000

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft

    122 Lovers Ln, Windham, CT 06280

    Nestled on a just under 2 acre lot in Windham, this refreshed home offers a tranquil retreat surrounded by nature. Step inside to discover a welcoming interior, spanning 1,736 square feet, with 4 bedrooms and 2 full bathrooms. The property boasts modern comforts while retaining its charming character. Beyond the thoughtfully placed living spaces, the true highlight of this property is its

    Michael Hernandez Signature Realty LLC

    122 Lovers Ln, Windham, CT 06280
  • /39

    $349,999

    • 5 Beds
    • 2.5 Baths
    • 1,952 Sq Ft

    240 Walnut St, Willimantic, CT 06226

    Hill Section of Willimantic, this beautifully well maintained Victorian Home at top of the hill offers rest and relaxing in quiet classic neighborhood. Many original features including pocket doors, moldings and stained glass window. Hardwood and tile throughout. 5 bedrooms, 2.5 baths, finished attic and finished basement with kitchenette and bath for in-law unit for potential rental income. 2

    Kathy Dubay I.M.A. Realty LLC

    240 Walnut St, Willimantic, CT 06226
  • /33

    $249,000

    • 3 Beds
    • 1 Bath
    • 1,076 Sq Ft

    222 Southridge Dr, Willimantic, CT 06226

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

    Taylor Gildein Re/Max Results

    222 Southridge Dr, Willimantic, CT 06226
  • /37

    $299,000 Open Sat 11AM - 12:30PM

    • 4 Beds
    • 3.5 Baths
    • 2,257 Sq Ft

    19 Impala Dr, Willimantic, CT 06226

    WELCOME to 19 Impala Drive, the IDEAL home for multiple generational living. This delightful colonial offers newly finished hardwood floors, New Furnace (less than 5 years old) and a well maintained opportunity to create your forever dream home!!! Location within a few minutes of shopping, minutes to Uconn & ECSU, near public transit and with convenient highway access. Featuring beautiful wood

    Robyn Letourneau Berkshire Hathaway NE Prop.

    19 Impala Dr, Willimantic, CT 06226
  • /40

    $279,000

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

    98 Windham St, Willimantic, CT 06226

    Step into timeless elegance at 98 Windham Street, a circa 1893 Victorian gem set on a rare double lot stretching from Windham St to Tingley St. Brimming with historic character, this home showcases beautifully preserved woodwork, rich hardwood floors, breathtaking stained glass windows, and period fixtures that echo its storied past. This home is in process of being lovingly renovated and

    Sue Esposito Home Selling Team

    98 Windham St, Willimantic, CT 06226
  • /34

    $599,000 Open House 8/10

    • 4 Beds
    • 3.5 Baths
    • 4,476 Sq Ft

    104 Windham Center Rd, Windham, CT 06280

    Elegant, Greek Revival Colonial home in historic Windham Center completely remodeled in 2005 by New England Design. This four bedroom, 3 full and one half bath features the charm and craftsmanship of bygone days with all of the convenience of modern day living. Three fireplaces, granite and marble flooring, graceful touches such as mahogany paneling in the study, bookcases, built ins, moldings,

    Lawrence Ross Weichert,REALTORS-Four Corners

    104 Windham Center Rd, Windham, CT 06280
  • /19

    $239,000

    • 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
  • /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
  • /40

    $449,900

    • 3 Beds
    • 3.5 Baths
    • 2,389 Sq Ft

    80 Tuckie Rd, Windham, CT 06280

    Beautiful Contemporary on 2.06 acres of professionally landscaped grounds. Home is set back off the road allowing for privacy and space. Walk thru the front door and there is a first floor bedroom and full bath for single floor living if that is what you need. As you continue on it opens up to an open floor plan with soaring vaulted ceilings, skylights and large windows which bring in amazing

    Lisa Pekala Century 21 Clemens Group

    80 Tuckie Rd, Windham, CT 06280
  • /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
  • /26

    $115,000

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

    49 Haley Ln, Windham, CT 06256

    Spacious 3-bedroom, 2-bath home in Stonegate Manor! This 1,296 sq ft 2004 mobile home offers a functional layout with large rooms and solid construction. Convenient Windham location, close to shopping, dining, and highways. Great potential to make it your own!

    Dillon Cass eRealty Advisors, Inc.

    49 Haley Ln, Windham, CT 06256
  • /36

    $484,999

    • 8 Beds
    • 4 Baths
    • 4,808 Sq Ft

    40 Elm St, Willimantic, CT 06226

    ATTENTION INVESTORS!!! This incredible 10 CAP investment Opportunity for 4 units across 2 2-family properties may be exactly what you're looking for!!! Discover the potential in this centrally located low overhead property. With strong rental demand from nearby ECSU, Uconn and in the general market, vacancy will not be a problem. Tenant amenities include large backyards, with privacy and gardens.

    Robyn Letourneau Berkshire Hathaway NE Prop.

    40 Elm St, Willimantic, CT 06226
  • /32

    $489,999

    • 8 Beds
    • 4 Baths
    • 3,828 Sq Ft

    389 Pleasant St, Windham, CT 06226

    Prime Investment Opportunity in Willimantic! Excellent potential in a high-demand, low vacancy location. With strong bones, proximity to ECSU, public transit and downtown this property is perfect for investors or house hackers looking to build equity fast. NEW ELECTRIC PANELS, NEW HEAT AND HOT WATER FURNACES. Combine with other listed Willimantic properties: Elm st., Jackson St., and Chapman St.

    Robyn Letourneau Berkshire Hathaway NE Prop.

    389 Pleasant St, Windham, CT 06226
  • /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
  • /40

    $485,000

    • 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
  • /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
  • /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
  • /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
  • /18

    $127,500

    • 2 Beds
    • 1 Bath
    • 790 Sq Ft

    270 S Windham Rd Unit 63, Willimantic, CT 06226

    Welcome to 270 S Windham Road in Willimantic, CT! This beautifully updated first-level condo offers the perfect blend of comfort and convenience. Ideal for first-time buyers, downsizers, or investors, this well-maintained unit features modern finishes and a thoughtfully designed layout. Step inside to discover a bright, freshly painted living space with newer flooring and stylish updated

    Mary Mercer Executive Real Estate Inc.

    270 S Windham Rd Unit 63, Willimantic, CT 06226
  • /30

    $150,000

    • 2 Beds
    • 1 Bath
    • 1,035 Sq Ft

    29 Kathleen Dr Unit 9D, Willimantic, CT 06226

    **Multiple offers** Seller is requesting final offers be submitted by Wednesday, April 30, 2025 at 5:00pm. Welcome to Elm Tree Village, located in the heart of Willimantic, CT. If you're looking for a cozy & comfortable living space, this 1st floor, 2-bedroom ranch-style condo is perfect for you. With 1035 square feet of living space, this unit offers an open floor plan, a cozy corner fireplace,

    The Bowes Team RE/MAX on the Bay

    29 Kathleen Dr Unit 9D, Willimantic, CT 06226
  • /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
  • /2

    $120,200

    • 3 Beds
    • 2 Baths
    • 1,141 Sq Ft

    5 Woods Way Unit WOOD005, Windham, CT 06256

    Welcome to Stonegate Manor, an all-age active and vibrant community, where you can find yourself in your dream home. We have a stunning, brand new, beautiful, 2025 3 bed, 2 bath home for sale featuring 1141.52 sq ft of beautifully designed living space. Located in North Windham. Step inside to find an open-concept floor plan, hardwood floors, high ceilings and natural light. The kitchen boasts

    Jude Gray Stonegate Manor

    5 Woods Way Unit WOOD005, Windham, CT 06256
  • /2

    $124,800

    • 3 Beds
    • 2 Baths
    • 1,141 Sq Ft

    22 Pond Way Unit POND022, Windham, CT 06256

    Welcome to Stonegate Manor an active and vibrant community, where you can find yourself in your dream home. We have a stunning, brand new, beautiful, 2025 3 bed, 2 bath home for sale featuring 1141.52 sq ft of beautifully designed living space. Located in North Windham. Step inside to find an open-concept floor plan, hardwood floors, high ceilings and natural light. The kitchen boasts stainless

    Jude Gray Stonegate Manor

    22 Pond Way Unit POND022, Windham, CT 06256
  • /2

    $139,500

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

    33 Woods Way Unit WOOD033, Windham, CT 06256

    Welcome to Stonegate Manor an active and vibrant community, where you can find yourself in your dream home. We have a stunning, brand new, beautiful, 2025 3 bed, 2 bath home for sale featuring 1356 sq ft of beautifully designed living space. Located in North Windham. Step inside to find an open-concept floor plan, hardwood floors, high ceilings and natural light. The kitchen boasts stainless

    Jude Gray Stonegate Manor

    33 Woods Way Unit WOOD033, Windham, CT 06256
  • /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
  • /26

    $283,900 Coming Soon

    • 2 Beds
    • 1 Bath
    • 1,178 Sq Ft

    188 Oxbow Dr, Willimantic, CT 06226

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

    Peter Baker RE/MAX Bell Park Realty

    188 Oxbow Dr, Willimantic, CT 06226
How to Buy a Home How to Finance a Home How to Sell a Home