Windham CT Real Estate

120 North Street Windham CT 06226

MLS Number 24204552

  • Multi Family Multi-Family For Sale
  • Square Feet 3,389
  • Acreage 0.26
  • Bedrooms 10
  • Bathroom 5

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 space, or future supplemental income opportunities. Conveniently located near Eastern Connecticut State University, downtown Willimantic, shopping, dining, and major commuter routes. Great opportunity to add a multifamily asset to an investment portfolio.

Listed by Michelle Mandel of Carl Guild & Associates

$
$
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$/month over payments
Federal 30-year interest rate: 7.03% last updated on Sep 24, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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33 Machine Shop Hill Road Windham CT 06266

MLS Number 24200058

  • Single Family
  • Square Feet 2,548
  • Bedrooms 4
  • Bathroom 4
  • Year Built 1850

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 kitchen, dining room, and living room, providing a comfortable layout for everyday living and entertaining. Main-level laundry adds even more convenience. The separate in-law living area offers first-floor living with 1 bedroom, 1 full bath, its own laundry area, and comfortable living space-ideal for extended family, guests, or multigenerational living. Major improvements include a new roof and new furnace, along with extensive interior renovations throughout. Outside, enjoy a large deck perfect for relaxing, entertaining, or summer gatherings. The property also features 2 detached garages, one that is oversized with heat, providing plenty of room for vehicles, storage, a workshop, or hobbies. It's a must see!!!

Listed by Michele Geragotelis of RE/MAX Bell Park Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Sep 24, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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56 Sundale Drive Windham CT 06280

Windham, CT56 Sundale Drive

Price$519,000

Est. Mortgage: $/month

MLS Number 24200078

  • Single Family
  • Square Feet 2,142
  • Bedrooms 4
  • Bathroom 3
  • Year Built 1971

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 main level features a streamlined kitchen with Corian countertops and a cozy dining area overlooking the patio and pool. Enjoy your morning coffee in the inviting den, complete with a fireplace, custom paneling and built in bookcases. A main level bedroom, half bathroom, formal dining room and spacious living room provide plenty of flexibility for everyday living and entertaining. Upstairs, you will find two additional bedrooms, a full bathroom and a spacious primary suite with its own private bathroom. The finished lower level offers even more living space with a large entertainment area, bar, office, utility area and cedar lined walk in closet. Major updates include a new roof in 2022, windows and driveway in 2020, chimney liner in 2023, pool pump in 2023, resurfaced tennis court in 2022 and sump pump in 2020. Additional features include 200 amp electrical service, a Buderus furnace, attic fan and well expansion tank. Conveniently located approximately 18 minutes from UConn, 17 miles from Norwich and 34 miles from Hartford, this peaceful property offers space, privacy and amenitie

Listed by Melissa DiPiazza of RE/MAX One

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Sep 24, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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415 Jerusalem Road Windham CT 06280

Windham, CT415 Jerusalem Road

Price$489,900

Est. Mortgage: $/month

MLS Number 24195334

  • Single Family
  • Square Feet 2,856
  • Bedrooms 4
  • Bathroom 3
  • Year Built 1968

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 three bedrooms share a bathroom. A cozy den connects the primary bedroom to the large living room with fireplace and pellet stove insert. Bring your ideas to the lower level with its finished space with a half bath. The three car garage is heated and offers plenty of space for any projects. Close to an acre this beautifully landscaped lot offers vibrant colors and a peaceful setting.

Listed by Rick J. Loranger of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Sep 24, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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28 Pleasant Street Windham CT 06226

MLS Number 24204645

  • Multi Family Multi-Family For Sale
  • Square Feet 2,674
  • Acreage 0.53
  • Bedrooms 5
  • Bathroom 3

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

Listed by Kathy Dubay of I.M.A. Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Sep 24, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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260 Summit Street Windham CT 06226

MLS Number 24185574

  • Multi Family Multi-Family For Sale
  • Square Feet 2,939
  • Acreage 0.13
  • Bedrooms 9
  • Bathroom 4

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 privacy for occupants while the property's central location adds to its long-term appeal. Whether you're looking to expand your investment portfolio or offset your housing costs with rental income, this property presents a versatile opportunity in a convenient location.

Listed by Michelle Mandel of Carl Guild & Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Sep 24, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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187 Tuckie Road Windham CT 06256

Windham, CT187 Tuckie Road

Price$380,000

Est. Mortgage: $/month

MLS Number 24192900

  • Single Family
  • Square Feet 2,158
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1967

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 fall in love w/the expansive backyard. An incredible space for entertaining, backyard bbq's, gatherings, gardening or simply enjoying the serenity of your own private oasis. Inside, you'll find over 2,100 square feet of warm, inviting living space featuring 3 spacious bedrooms + 2 full bathrooms designed for comfortable everyday living. The open concept layout seamlessly connects the kitchen, complete with stainless steel appliances, a center island and ample seating, to the dining area and cozy family room with a beautiful brick fireplace, creating the perfect space for gathering with family and friends. The flexible floor plan includes a convenient 1st floor bedroom w/sliders that lead to your back deck + gleaming hardwood floors flow throughout much of the home. A 2nd fireplace creates an add'l cozy living space, perfect for relaxing after a long day. The partially finished LL is where the possibilities truly come to life. Whether you've been dreaming of a home office, media room, fitness studio or playroom, this versatile space is is a blank canvas ready to fit your lifestyle.

Listed by Meghan Wininger of Real Broker CT,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Sep 24, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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207 Summit Street Windham CT 06226

MLS Number 24195071

  • Single Family
  • Square Feet 2,318
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1892

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 ceilings, creating an impressive space for everyday living and entertaining. Nearly as spacious, the versatile third-floor retreat includes a full bathroom, extensive built-in storage, counter space, and a private balcony-making it ideal as a generous primary suite, guest room, living area, home office, creative studio, or flexible multigenerational living space. Distinctive Art Deco-inspired design elements add personality throughout, creating a home unlike any other. The composite and stone patio, landscaped yard, and the refreshing shade of mature trees make it an ideal spot to enjoy your morning coffee or unwind at the end of the day. The impressive stone foundation basement boasts high ceilings, a laundry area with utility sink, and clean storage space. Conveniently located near Eastern Connecticut State University, downtown Willimantic's restaurants, shops, entertainment, and local events, with easy access to Route 6 and a short drive to UConn. A rare opportunity to own a distinctive property where historic charm and modern comfort blend into an unforgettable place to call home.

Listed by Sue Esposito of Home Selling Team

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Sep 24, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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15 Cracow Avenue Windham CT 06280

Windham, CT15 Cracow Avenue

Price$350,000

Est. Mortgage: $/month

MLS Number 24181488

  • Single Family
  • Square Feet 1,228
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1972

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 featuring quartz countertops and newer cabinetry. Replacement windows throughout add to the home's comfort and efficiency, while several major improvements have already been taken care of-including a brand-new roof, upgraded electrical panel, and brand-new whole-house water filtration system. Outside, the fully fenced backyard is designed to be enjoyed. The in-ground pool creates the perfect setting for summer afternoons, weekend gatherings, or simply relaxing at home, and buyers can enjoy added peace of mind with a brand-new pool pump and filter already installed.

Listed by AJ Davis of Better Homes and Gardens Real Estate Executive Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Sep 24, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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19 Bellevue Street Windham CT 06226

MLS Number 24210038

  • Multi Family Multi-Family For Sale
  • Square Feet 2,678
  • Acreage 0.14
  • Bedrooms 5
  • Bathroom 2

Spacious two-family home offering 5 bedrooms, 2 baths, a large basement, detached garage, covered front porch, and flexible space throughout. Great opportunity for an owner-occupant or investor. Unit 1 offers approximately 1,453 sq. ft. with 3 bedrooms and 1 full bath. The first floor features a large bedroom, spacious living room, kitchen, and full bath, with two additional bedrooms upstairs. The unit also has access to an approximately 1,201 sq. ft. unfinished basement with washer and dryer and plenty of storage space. Unit 2 offers approximately 1,026 sq. ft. with 2 bedrooms and a 3/4 bath. It includes a living room, kitchen, large bedroom with balcony, second bedroom, and approximately 216 sq. ft. of additional attic/storage space on the third floor. The property also includes a 462 sq. ft. detached garage and off-street parking. Convenient opportunity to live in one unit while renting the other, or add a two-family property to your investment portfolio. Furniture shown in the photos can be included with the sale at no additional cost.

Listed by Kris J. Lippi of Get Listed Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Sep 24, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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11 Type Road Windham CT 06266

MLS Number 24207636

  • Multi Family Multi-Family For Sale
  • Square Feet 1,890
  • Co List Office Name Home Selling Team
  • Acreage 0.42
  • Bedrooms 4

Investors and owner-occupants, take notice! This well-maintained two-family home is ideally situated on a quiet dead-end street and offers an excellent opportunity for both rental income and owner occupancy. One unit is currently unoccupied, providing flexibility for a buyer looking to move in while generating rental income from the second unit. Each spacious unit features 2 bedrooms, 1 full bath, and approximately 1,000 square feet of living space, with comfortable layouts and strong rental appeal. Separate utilities simplify ownership and management, while basement laundry hookups provide added convenience for tenants. Set on nearly half an acre, the property offers plenty of outdoor space, a welcoming front porch, and an abundance of off-street parking. Conveniently located near shopping, dining, schools, and major routes, this property combines a peaceful setting with easy access to everyday amenities. Whether you're looking to expand your investment portfolio or take advantage of an owner-occupied opportunity, this versatile two-family property is ready to deliver flexibility, space, and potential.

Listed by Stephen Galinat and John F. Fulton of Home Selling Team

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Sep 24, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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134 Lauter Avenue Windham CT 06226

MLS Number 24203882

  • Single Family
  • Square Feet 1,488
  • Bedrooms 5
  • Bathroom 2
  • Year Built 1956

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 natural light. Three comfortable bedrooms and a full bath complete this level, providing ample space for comfortable living. Descend to the lower level, where you'll find a fully equipped in-law suite. This versatile space includes a full bath, kitchen, two additional bedrooms, and a cozy living area, all accessible via a private entrance - The roof has been updated just five years ago, ensuring peace of mind for years to come. Enjoy the convenience of walking to nearby restaurants, parks, and Eastern Connecticut State University, with UCONN only a short drive away. Don't miss the opportunity to make this welcoming home your own!

Listed by Jeanne L. Crum of Home Selling Team

$
$
%
$/month over payments
Federal 30-year interest rate: 7.03% last updated on Sep 24, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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