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Homes for Sale near Windham Middle School

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  • /40

    $519,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,142 Sq Ft

    56 Sundale Dr, Windham, CT 06280

    Welcome home to your own private retreat! Set on 1.09 beautifully landscaped acres in a quiet neighborhood, this well built and thoughtfully maintained home offers 4 bedrooms, 2.5 bathrooms, an attached 2 car garage, an inground pool and a private tennis court. Lovingly maintained and ready for your own personal touches, this home offers an incredible opportunity to make it truly your own. The

    Agent Photo

    Melissa DiPiazza

    RE/MAX One

    56 Sundale Dr, Windham, CT 06280
  • /39

    $199,900

    • 2 Beds
    • 1.5 Baths
    • 1,492 Sq Ft

    29 Kathleen Dr Unit 3B, Willimantic, CT 06226

    Wake up with the sunrise and end your day with sunsets in this easy-living light-filled condo in a fantastic location! Welcome to Elm Tree Village, where this well-kept two-bedroom, 1.5-bath townhouse offers comfortable, low-maintenance living in a convenient Windham location. The main level features a bright, inviting living space with an easy-flowing layout for everyday living and entertaining.

    Agent Photo

    Stephanie Rush

    RE/MAX Legends

    29 Kathleen Dr Unit 3B, Willimantic, CT 06226
  • /4

    $49,000

    • Land
    • 12,632 Sq Ft
    • $168,966 per Acre

    90 Serwan Ave, Windham, CT 06226

    This nice residential lot sits on the edge of Mansfield and Windham. This property offers an opportunity to secure residential land in an established neighborhood with essential utilities accessible. Zoning: R-4 (Residential) Utilities: Public water and public sewer are available in the street; electricity and cable are also accessible at the site. Taxes are $109 (2025). Situated in a residential

    Agent Photo

    Sharon Watson Stokland

    List N Show LLC

    90 Serwan Ave, Windham, CT 06226
  • /10

    $249,900

    • Land
    • 25.7 Acres
    • $9,724 per Acre

    220 Plains Rd, Windham, CT 06280

    Wonderful potential development opportunity. Road frontage on 2 roads, approximately 1350' of frontage on Plains Rd., and approximately 450' of frontage on Anna Maria Ln., and existing cul-du-sac subdivision. Possible 7-8 lots subdivision to be created.

    Agent Photo

    Rick Nassiff

    KW Legacy Partners

    220 Plains Rd, Windham, CT 06280
  • /7

    $39,900

    • Land
    • 4.2 Acres
    • $9,500 per Acre

    46 North Rd, Windham, CT 06280

    Great opportunity to own a lot of record at a great price, approx. 3.9-4.2 acres. Offered as raw land. No formal survey available, all soil testing and surveying to be done by the potential owner. Great location, North Rd. is Route 14, across from the Windham Center School.

    Agent Photo

    Rick Nassiff

    KW Legacy Partners

    46 North Rd, Windham, CT 06280
  • /2

    $299,900

    • 6 Beds
    • 3 Baths
    • 2,700 Sq Ft

    14 Carey St, Willimantic, CT 06226

    Excellent opportunity to own a spacious 2-family home with great flexibility for investors or owner-occupants. The first unit offers 2 bedrooms and 1 full bath, while the second unit features a generous 4-bedroom, 2-bath layout, providing plenty of space for larger households or strong rental potential. A 2-car garage adds valuable parking and storage, making this property even more attractive.

    Agent Photo

    Amy Rio

    Better Homes and Gardens Real Estate Executive Real Estate

    14 Carey St, Willimantic, CT 06226
  • /40

    $319,900

    $15K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,379 Sq Ft

    130 Windham Rd, Willimantic, CT 06226

    If you're looking for a spacious investment property or a home where you can add your own personal touches, this could be the one! Ideally located close to Eastern Connecticut State University, this 4-bedroom Colonial offers excellent potential as a housing investment, especially with a separate in-law apartment. The home features generously sized rooms, beautiful wood floors, some updated

    Lisa Perry CR Premier Properties

    130 Windham Rd, Willimantic, CT 06226
  • /25

    $464,997

    Open Sun 11AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 1,472 Sq Ft

    21 Jack Henry Dr, Windham, CT 06280

    Welcome to this beautiful Colonial home, offering the perfect blend of classic charm, comfort, and space. Step inside to find gleaming hardwood floors and generously sized living areas filled with warmth and character. Spacious bedrooms provide plenty of room to relax and unwind, while the expansive living spaces offer a versatile layout ideal for both everyday living and entertaining. At the

    Terence Dominick Exceptional Real Estate LLC

    21 Jack Henry Dr, Windham, CT 06280
  • /30

    $549,900

    • 4 Beds
    • 3.5 Baths
    • 2,548 Sq Ft

    33 MacHine Shop Hill Rd, South Windham, CT 06266

    Historic 1850 Charm with Modern Updates & In-Law Living! Step inside this beautifully remodeled 1850 home, thoughtfully updated for today's lifestyle while maintaining the character and charm that makes an older home so special. The main living portion of the home offers 3 spacious bedrooms, 2.5 baths, and a dedicated office space. The heart of the home features a bright and inviting open-concept

    Michele Geragotelis RE/MAX Bell Park Realty

    33 MacHine Shop Hill Rd, South Windham, CT 06266
  • /40

    $489,900

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,856 Sq Ft

    415 Jerusalem Rd, Windham, CT 06280

    Pristine property with one floor living and enough room for all! Beautiful updated kitchen with breakfast bar, granite counters and access to the back deck perfect for all your gatherings by the pool or firepit. Amazing primary bedroom suite with hardwood floors, cathedral ceiling, sitting area, walk-in closet, full bath with whirlpool tub and access to your own private office. The remaining

    Rick Loranger Coldwell Banker Realty

    415 Jerusalem Rd, Windham, CT 06280
  • /39

    $309,900

    Open Sun 12PM - 2PM
    • 3 Beds
    • 1 Bath
    • 1,336 Sq Ft

    349 Mansfield Ave, Willimantic, CT 06226

    A delightful gem of a home, this Cape is set in the heart of Willimantic. This home offers easy access to town, shopping, and commuting routes. A charming, move-in-ready opportunity is updated and ready for its next owner, with an open-air plan and unique, tasteful finishing touches throughout. Fresh, modern updates within the last 4 years include: kitchen with granite counters and new stainless

    Paul Cutler Keller Williams Realty Gr.Worc

    349 Mansfield Ave, Willimantic, CT 06226
  • /21

    $199,000

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft

    28 Lovers Ln, Windham, CT 06280

    Welcome to 28 Lovers Ln in Windham! This inviting home offers comfortable living spaces and plenty of potential to make it your own. Enjoy a functional layout with bright rooms, generous living areas, and a setting that provides both convenience and privacy. The property offers outdoor space for relaxing, entertaining, or enjoying the changing New England seasons. Conveniently located near local

    Thomas Mele Social & Co Realty

    28 Lovers Ln, Windham, CT 06280
  • /19

    $189,000

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

    38 Wilson St, Willimantic, CT 06226

    Welcome to 38 Wilson Street in Willimantic, offering a spacious 7-bedroom, 2-bathroom layout on approximately 0.17 acres. Built in 1910, this property provides ample room for comfortable living, guests, or flexible use. The home's established character and convenient, easy access to local shopping, dining, schools, parks, and everyday amenities. A versatile opportunity for buyers seeking generous

    Thomas Mele Social & Co Realty

    38 Wilson St, Willimantic, CT 06226
  • /7

    $9,400

    $21K PRICE DROP
    • Land
    • 7,405 Sq Ft
    • $55,294 per Acre

    28 Cloran St, Windham, CT 06226

    Corner vacant lot opportunity in Windham, CT! This 0.17-acre (7,405 sq ft) parcel is located at the intersection of Cloran St and Alice St, offering dual road frontage and easy access. The property features level terrain with light wooded coverage and is situated in a residential setting near Route 32 and local amenities. Buyer to perform all due diligence regarding zoning, utilities, and

    Derek Greene Derek Greene

    28 Cloran St, Windham, CT 06226
  • /31

    $489,000

    • 5 Beds
    • 3 Baths
    • 2,674 Sq Ft

    28 Pleasant St, Willimantic, CT 06226

    3 Family well maintained for sale in Willimantic with extra large lot size, .53 ac. and extra large out building for garage, storage and workbench area with power. 2 units on first floor with one unit on second floor. close and convenient to Main Street and bus line. Historical home been in family for generations. see agent remarks

    Kathy Dubay I.M.A. Realty LLC

    28 Pleasant St, Willimantic, CT 06226
  • /30

    $70,000

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    30 Haley Ln, Windham, CT 06256

    One level living in this mobile home located in Stone Gate Manor. Home offers large, covered deck, nice shed for storage and backs up to woods. Home has a nice open floor plan with a large living room open into the eat in kitchen with lots of good cabinet space. Laundry off kitchen, Primary bedroom has private full bath with shower stall and garden tub, walk in closet. On the other side of Mobile

    Jeanne Crum Home Selling Team

    30 Haley Ln, Windham, CT 06256
  • /40

    $365,000

    • 3 Beds
    • 2 Baths
    • 2,318 Sq Ft

    207 Summit St, Willimantic, CT 06226

    Step into a truly one-of-a-kind home where history, character, and creativity come together. Originally built circa 1892 as the historic Hilltop Hose Company No. 3 Firehouse, this remarkable property has been thoughtfully transformed into an eclectic single-family residence while honoring its architectural roots. The 1,000-square-foot first floor offers an expansive open layout with soaring

    Sue Esposito Home Selling Team

    207 Summit St, Willimantic, CT 06226
  • /18

    $160,000

    $6K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    28 Circle Dr, Windham, CT 06256

    *** Highest and Best due 12pm Monday 8/10/2026 Completely remodeled 3-bedroom, 2-bath mobile home in North Windham! This move-in-ready home has been thoughtfully updated throughout and features a brand-new roof, new appliances, and modern finishes from top to bottom. The interior offers a bright and functional layout with updated flooring, refreshed kitchen and bathrooms, and comfortable living

    Arielle Ruffin Choice Realty

    28 Circle Dr, Windham, CT 06256
  • /21

    $145,000

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

    57 Circle Dr, Windham, CT 06256

    This Cute, Clean and Spacious, 3-bedroom, 2 bath home in the Stonegate Manor has 1152 Square Feet of Living Space. Appliances convey. There is an 8x10 Shed that conveys as well. Updates are as follows.... Roof is only 2 years old, and hot water heater only 3-4 years old. New flooring and subflooring in primary bedroom/bath. 2 pets are allowed per park regulations. Park has No age requirement!

    Ginny Dunbar RE/MAX One

    57 Circle Dr, Windham, CT 06256
  • /17

    $479,000

    $1K PRICE DROP
    • 9 Beds
    • 4 Baths
    • 2,939 Sq Ft

    260 Summit St, Windham, CT 06226

    Opportunity awaits with this multi-family property in Willimantic. Featuring multiple residential units with a mix of layouts, this property offers flexibility for both investors and owner-occupants seeking rental income. Conveniently located near Eastern Connecticut State University, shopping, restaurants, parks, public transportation, and major commuter routes. Separate living spaces provide

    Michelle Mandel Carl Guild & Associates

    260 Summit St, Windham, CT 06226
  • /34

    $289,000

    Open Sun 10:30AM - 12PM
    • 3 Beds
    • 1.5 Baths
    • 1,535 Sq Ft

    143 Southridge Dr, Willimantic, CT 06226

    Pride of ownership shines throughout this beautifully updated 3-bedroom, 1.1 bath ranch, ideally situated in a convenient neighborhood setting. The bright, freshly painted interior features gleaming hardwood floors, newer carpeting in all three bedrooms, freshly painted doors with updated hardware, custom window treatments, and stylish new lighting throughout. The updated kitchen offers newer

    Doreen Amata Coldwell Banker Realty

    143 Southridge Dr, Willimantic, CT 06226
  • /14

    $324,900

    Open Sun 2AM - 4PM
    • 3 Beds
    • 1 Bath
    • 804 Sq Ft

    14 Tunxis Ln, Willimantic, CT 06226

    Welcome to 14 Tunxis Lane! This well-maintained 3-bedroom, 1-bathroom home is move-in ready and offers a wonderful opportunity for its next owner. Recent improvements include newer windows, a new front entry door, and refreshed landscaping, enhancing both curb appeal and functionality. Situated near a quiet cul-de-sac, the property offers a peaceful and private setting with a spacious back and

    Justin Marino Marino Realty LLC

    14 Tunxis Ln, Willimantic, CT 06226
  • /17

    $290,000

    • 4 Beds
    • 2 Baths
    • 1,560 Sq Ft

    86 Chestnut St, Willimantic, CT 06226

    INVESTOR OPPORTUNITY IN WILLIMANTIC! Bring your vision to 86 Chestnut Street, an approximately 1,560 SF multifamily property. Originally built in 1887, the property offers timeless architectural character and charm rarely found in newer construction. Conveniently located near downtown Willimantic, Eastern Connecticut State University, shops, restaurants, services, and major area routes. Offered

    Marcus Hamilton CENTURY 21 Shutters & Sails

    86 Chestnut St, Willimantic, CT 06226
  • /22

    $84,900

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    29 James Dr, North Windham, CT 06256

    Welcome to this well-maintained 2-bedroom, 2-full-bath mobile home located in Stonegate Manor, offering a comfortable and functional floor plan. The primary bedroom features a private full bath and walk-in closet, while the two bedrooms are thoughtfully situated at opposite ends of the home for added privacy. The fully applianced kitchen includes a convenient snack bar, with a dedicated laundry

    Shawn Chaplin Weichert,REALTORS-Four Corners

    29 James Dr, North Windham, CT 06256
  • /34

    $634,900

    • 10 Beds
    • 5 Baths
    • 3,389 Sq Ft

    120 North St, Willimantic, CT 06226

    Income producing multi family property offering a strong opportunity for investors or owner occupants alike. One unit is currently not leased, providing immediate leasing potential or flexibility for owner occupancy. Property presents the opportunity to generate rental income with additional upside potential over time. Detached garage offers added utility with potential for storage, workshop

    Michelle Mandel Carl Guild & Associates

    120 North St, Willimantic, CT 06226
  • /6

    $157,900

    • Land
    • 7,405 Sq Ft
    • $928,824 per Acre

    760 Main St, Willimantic, CT 06226

    Highly visible main street location in the middle of Willimantic's dining, retail, historic district, and municipal office area. Public water, sewer & gas, 57 ft road frontage, 12,500 traffic count with .17 of an acre in the B1 zone.

    Maxwell Lyman Lyman Real Estate

    760 Main St, Willimantic, CT 06226
  • /30

    $375,000

    • 6 Beds
    • 3 Baths
    • 3,300 Sq Ft

    115 Chapman St, Willimantic, CT 06226

    Very well maintained 3 family in vibrant Willimantic. 3 Units plus a 3-car garage (extra cash flow) and 2 building lots (lots of space for parking outdoor activities). Roof replaced in 2023 and the property needs nothing. Unit 1 is a 1-bedroom. Tenant pays all utilities and rent is $1100. Unit 2 is vacant and is a 2 (maybe 3) bedroom. Owner pays gas heat. The unit has electric hot water heater

    Carol Wanat Rockoff Realty

    115 Chapman St, Willimantic, CT 06226
  • /34

    $350,000

    $25K PRICE INCREASE
    • 3 Beds
    • 2 Baths
    • 1,228 Sq Ft

    15 Cracow Ave, Windham, CT 06280

    Move-in ready, single-level living meets your own private backyard retreat at 15 Cracow Avenue. This well-maintained 3-bedroom, 2-full-bath ranch offers the convenience buyers are searching for, with all three bedrooms and both full bathrooms located on the main living level. Inside, an open and inviting layout is highlighted by hardwood flooring, a wood-burning fireplace, and an updated kitchen

    AJ Davis Better Homes and Gardens Real Estate Executive Real Estate

    15 Cracow Ave, Windham, CT 06280
  • /32

    $260,000

    $115K PRICE DROP
    • 7 Beds
    • 4 Baths
    • 3,963 Sq Ft

    129 Valley St, Windham, CT 06226

    Mixed-use investment property with multiple income streams and strong value-add potential. The property is zoned B-1A and currently configured with two occupied residential units generating income, plus two additional gutted residential units with plumbing in place, ready for build-out. The property also includes a commercial storefront with a separate entrance, offering flexibility for a variety

    Kyle West eXp Realty

    129 Valley St, Windham, CT 06226
  • /37

    $152,000

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft

    6 Circle Dr, North Windham, CT 06256

    Welcome to 6 Circle Drive, a spacious 3-bedroom, 2-full-bath mobile home located in North Windham's Stonegate Manor mobile home park. Situated on a corner lot, this home features a large kitchen, generously sized bedrooms, and decent closet space throughout. The primary bedroom includes an en-suite bath with a relaxing jacuzzi soaking tub. Enjoy approximately 340 sq. ft. of side decking, perfect

    Franchesca Pescatello Prue Realty LLC

    6 Circle Dr, North Windham, CT 06256
  • /40

    $310,000

    • 5 Beds
    • 2 Baths
    • 1,488 Sq Ft

    134 Lauter Ave, Willimantic, CT 06226

    Charming One-Level Living Ranch Welcome to this delightful ranch-style home, perfectly situated on a serene, private lot adorned with beautiful fruit trees and a garden area. This residence offers the convenience of one-level living with a host of appealing updates. The main level features a modernized kitchen that flows seamlessly into a bright and airy living room, accentuated by abundant

    Jeanne Crum Home Selling Team

    134 Lauter Ave, Willimantic, CT 06226
  • /28

    $380,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,158 Sq Ft

    187 Tuckie Rd, North Windham, CT 06256

    Welcome to your own retreat! Perfectly positioned on a gorgeous, level 1 acre lot surrounded by mature trees, this beautifully maintained Cape offers the peaceful lifestyle you've been dreaming of. From the moment you arrive, you'll picture slow mornings spent on the charming front porch w/a cup of coffee and your favorite book, soaking in the quiet beauty that surrounds you. Out back, you'll

    Meghan Wininger Real Broker CT, LLC

    187 Tuckie Rd, North Windham, CT 06256
  • /15

    $215,000

    • 2 Beds
    • 1.5 Baths
    • 998 Sq Ft

    29 Kathleen Dr Unit 7E, Willimantic, CT 06226

    Welcome to this well maintained 2 bedroom, 1.5 bathroom condo in the peaceful Elm Tree Village community. With a living room that flows into the dining area, this home features a functional layout designed for easy living. The private deck is perfect for relaxing and enjoying the weather. There is also an attached garage and a basement offering ample storage space. Come add your touches and make

    Shacara Cook KW Legacy Partners

    29 Kathleen Dr Unit 7E, Willimantic, CT 06226
  • /19

    $219,000

    $19K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,078 Sq Ft

    129 Walnut St, Willimantic, CT 06226

    Charming Antique Colonial - Prime Windham Location Step back in time and experience the warmth and character of this classic 1915 Antique Colonial, beautifully situated on a desirable corner lot in Windham. This inviting home offers four spacious bedrooms and one full bath, along with a generously sized living room perfect for relaxing or entertaining. The bright eat-in kitchen provides a

    Lisa Therecka Therecka & Associates LLC

    129 Walnut St, Willimantic, CT 06226
  • /2

    $225,000

    • Land
    • 6.52 Acres
    • $34,509 per Acre

    0 Commerce Dr, Columbia, CT 06237

    6+ acres of commercial land, ideally situated at the end of the cul-de-sac in an established manufacturing/commercial area. This large parcel offers opportunity for a wide variety of commercial uses, subject to local zoning regulations. Don't miss this rare opportunity to own the last remaining lots in this desirable location!

    Tracy Doherty Countryside Realty

    0 Commerce Dr, Columbia, CT 06237
  • /32

    $194,000

    $5K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,807 Sq Ft

    15 Bellevue St, Willimantic, CT 06226

    Bring your vision to this four-bedroom home in Willimantic's Hill Section. With approximately 1,807 square feet of living space, the property features generously sized rooms, tall windows, original woodwork, and period details throughout. With thoughtful updates, this home has the potential to showcase its original character while being tailored to its next owner. Conveniently located near

    Michelle Mandel Carl Guild & Associates

    15 Bellevue St, Willimantic, CT 06226
  • /32

    $170,000

    $5K PRICE DROP
    • 6 Beds
    • 2 Baths
    • 1,948 Sq Ft

    11 Bellevue St, Willimantic, CT 06226

    Bring your vision to this six-bedroom home in Willimantic's Hill Section. With approximately 1,948 square feet of living space, the property features generously sized rooms, hardwood flooring, tall windows, original woodwork, and period details throughout. A brand-new roof has already been installed, providing a great start for future improvements. With thoughtful updates, this home has the

    Michelle Mandel Carl Guild & Associates

    11 Bellevue St, Willimantic, CT 06226
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