Windham & Willi

136 Chapman Street Windham CT 06226

MLS Number 24101734

  • Multi Family Multi-Family For Sale
  • Square Feet 4,466
  • Acreage 0.37
  • Bedrooms 12
  • Bathroom 5

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 17 unit portfolio. Combine with other listed Willimantic properties: Elm st., Jackson St., and Pleasant St. as a 17 unit portfolio. GOI:63,000 Expenses: 10,868 NOI: 52,132 10CAP PRO Forma NOI: 77,932!!! floor plans available**

Listed by Robyn Letourneau of Berkshire Hathaway NE Prop.

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$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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389 Pleasant Street Windham CT 06226

MLS Number 24101718

  • Multi Family Multi-Family For Sale
  • Square Feet 3,828
  • Acreage 0.32
  • Bedrooms 8
  • Bathroom 4

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. as a 17 unit portfolio. GOI:63,000 Expenses: 10,868 NOI: 52,132 10CAP PRO Forma NOI: 77,932!!! floor plans available**

Listed by Robyn Letourneau of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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4 Main Street Windham CT 06226

MLS Number 24099416

  • Multi Family Multi-Family For Sale
  • Square Feet 5,134
  • Acreage 1.54
  • Bedrooms 9
  • Bathroom 5

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 charming ranch-style 2-bedroom apartment located above a detached 3-car garage. Key features include: Whole-house generator for the main home. Newer boiler and hot water heater. New roof. Plenty of off-street parking. Whether you're a seasoned investor or just getting started, this property is a fantastic opportunity to build wealth through real estate. Schedule your showing today!

Listed by Tammy J. Arute of Arute Realty Group LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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4 Main Street Windham CT 06226

MLS Number 24104813

  • Single Family
  • Square Feet 5,134
  • Bedrooms 8
  • Bathroom 4
  • Year Built 1830

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 charming ranch-style 2-bedroom apartment located above a detached 3-car garage. Key features include: Whole-house generator for the main home. Newer boiler and hot water heater. New roof. Plenty of off-street parking. Whether you're a seasoned investor or just getting started, this property is a fantastic opportunity to build wealth through real estate. Schedule your showing today!

Listed by Tammy J. Arute of Arute Realty Group LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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40 Elm Street Windham CT 06226

Windham, CT40 Elm Street

Price$484,999

Est. Mortgage: $/month

MLS Number 24100884

  • Multi Family Multi-Family For Sale
  • Square Feet 4,808
  • Acreage 0.23
  • Bedrooms 8
  • Bathroom 4

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. Conveniently walkable to downtown, near bus lines and ideal for investors or renovation-minded buyers looking to restore charm and build equity. Off street parking, long term tenants, and under market rents make this a Value-add asset. Add 2 more bedrooms to the top floor units and consider pro-forma rents. These are stable in place, but the sky is the limit. Combine with other listed Willimantic properties: Pleasant St., Jackson St., and Chapman St. as a 17 unit portfolio. GOI:63,000 Expenses: 10,868 NOI: 52,132 10CAP PRO Forma NOI: 77,932!!! floor plans available**

Listed by Robyn Letourneau of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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80 Tuckie Road Windham CT 06280

Windham, CT80 Tuckie Road

Price$479,900

Est. Mortgage: $/month

MLS Number 24109298

  • Single Family
  • Square Feet 2,389
  • Bedrooms 3
  • Bathroom 4
  • Year Built 1982

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 light and views of the fenced in backyard from all angles. The spacious living room, dining room(playroom) and informal dining area make up this open floor plan. The Kitchen with Stainless Steel appliances, new flooring, access to the half bath, laundry room, two car garage and the backyard. Make your way upstairs to the primary bedroom with walk-in closet, full bath and vaulted ceilings. The natural light pours in thru the large windows. There is another full bath at the end of the hallway. A third bedroom with new wall to wall carpeting and another room which is used as a 4th bedroom or can be used as an office if needed also has new carpeting. A new water heater was installed 7/2025. The property contains a large shed which has electricity, AC and heat. Presently used as a gym, it makes a great workshop, garden shed, studio or she shed/man cave. The backyard is completely fenced with additional shed including a separate fenced area with a playscape and patio close to the house. The property extends past the fence in the back. This property has something for everyone.

Listed by Lisa Pekala of Century 21 Clemens Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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1145 Windham Road Windham CT 06266

MLS Number 24059899

  • Single Family
  • Square Feet 1,900
  • Bedrooms 3
  • Bathroom 3
  • Year Built 2025

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 a convenient laundry room, and walk-in storage/attic space over the garage. See floor plans on listing photos, 3D walk through, click camera below listing photo All Financing types considered

Listed by Timothy Morse of Home Selling Team

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$
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$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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1157 Windham Road Windham CT 06266

MLS Number 24059900

  • Single Family
  • Square Feet 1,400
  • Bedrooms 3
  • Bathroom 2
  • Year Built 2025

New Raised Ranch Close to completion and available to view. 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 two car under house garage, and the potential to finish the other half to add living space. All financing types considered

Listed by Timothy Morse of Home Selling Team

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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337 South Windham Road Windham CT 06226

Windham, CT337 South Windham Road

Price$437,000

Est. Mortgage: $/month

MLS Number 24072329

  • Single Family
  • Square Feet 2,905
  • Bedrooms 4
  • Bathroom 3
  • Year Built 1850

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 and bathrooms thoughtfully designed with contemporary finishes while preserving the home's classic character. Gleaming hardwood floors flow throughout, adding warmth and sophistication to every room. Whether you're entertaining in the bright, open living areas or enjoying quiet moments on the picturesque property, this home is truly a rare find. Don't miss this upgraded opportunity make 337 S. Windham Rd your new home today! Sold As-IS

Listed by Alexia Andrade of US Asset Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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240 Walnut Street Windham CT 06226

MLS Number 24109416

  • Single Family
  • Square Feet 1,952
  • Bedrooms 5
  • Bathroom 3
  • Year Built 1911

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 car detached garage with storage shed. secluded fenced in yard with above ground pool to spend time in during a heatwave. English perennial gardens with spring/summer perennials, ground cover and shrubs. Walk to ECSU and bus line to Uconn. Move right in to this well-loved home for you and your extended family. see agent remarks.

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

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$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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9 Ann Street Windham CT 06226

Windham, CT9 Ann Street

Price$330,000

Est. Mortgage: $/month

MLS Number 24091298

  • Multi Family Multi-Family For Sale
  • Square Feet 2,200
  • Acreage 0.12
  • Bedrooms 5
  • Bathroom 2

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 with hardwood floors. Both units have front and rear entrances, 2 driveways, fenced in backyard, one car garage. Basement has separate entrances for each unit, laundry hookups in basement on both sides. Newer roof, newer windows throughout, freshly painted.

Listed by David Breau of eXp Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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87 North Street Windham CT 06226

MLS Number 24100204

  • Multi Family Multi-Family For Sale
  • Square Feet 2,981
  • Acreage 0.21
  • Bedrooms 6
  • Bathroom 2

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, currently offers two bedrooms, a spacious kitchen, dining room, a laundry area, and a full bathroom. Its existing condition presents a stable rental income stream, mitigating risk during the renovation of the front house. The front house, approximately 1,757 square feet, has been completely stripped to the studs, providing a blank canvas for a renovation. New roof was put on in 2023. The size and layout allow for the creation of a four-bedroom residence, significantly increasing potential rental income or providing expansive living space for an owner-occupant. Rehabilitation plans could incorporate features to maximize rental appeal and profitability. The location is another key advantage. The property's proximity to Main Street places it within easy walking distance and bus lines to shopping mall, restaurants, and Eastern Connecticut State University, only a 15-minute drive to UCONN, and steps away from the bus line, serving Mansfield, Storrs, and Willimantic. Providing a strong pool of potential renters.

Listed by Toni A. Iandoli of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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106 Oxbow Drive Windham CT 06226

MLS Number 24104775

  • Single Family
  • Square Feet 1,784
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1978

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 bedrooms complete the main level. The lower level has a 11 x 20 bedroom which could be used for multiple purposes if needed. Newer half bath and laundry room are also included on the lower level. An office, utility room and storage room gives you room to grow. Large one car garage with shelves will help with storage, and if you need more room the shed will convey. A must see and priced to sell!

Listed by Sondra A. Reid of Home Selling Team

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$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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100 South Street Windham CT 06226

MLS Number 24099579

  • Multi Family Multi-Family For Sale
  • Square Feet 1,932
  • Acreage 0.12
  • Bedrooms 6
  • Bathroom 2

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, this property offers instant cash flow and ease of ownership. Conveniently located near downtown Willimantic, it's close to shopping, restaurants, and public transit-making it highly desirable for renters. Add this dependable asset to your portfolio-schedule your showing today!

Listed by Amber Jones of KW Legacy Partners

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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Windham CT 06280

Windham, CT

Price$295,000

Est. Mortgage: $/month

MLS Number 24108641

  • Single Family
  • Square Feet 2,248
  • Bedrooms 3
  • Bathroom 3
  • Year Built 1969

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!

Listed by Valerie Yankus of Property Shoppe,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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96 South Street Windham CT 06226

MLS Number 24099165

  • Multi Family Multi-Family For Sale
  • Square Feet 1,736
  • Acreage 0.12
  • Bedrooms 6
  • Bathroom 2

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 costs. With stable tenants and fair market rents, this property is perfect for investors seeking a low-hassle addition to their portfolio. Located near downtown Willimantic, shopping, dining, and public transportation are easily accessible.

Listed by Amber Jones of KW Legacy Partners

$
$
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$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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20 Greystone Street Windham CT 06226

MLS Number 24109506

  • Single Family
  • Square Feet 1,344
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1910

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 !

Listed by Frank Fonteyn of Prestige Realty Group

$
$
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$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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77 Plains Road Windham CT 06280

Windham, CT77 Plains Road

Price$259,000

Est. Mortgage: $/month

MLS Number 24110091

  • Single Family
  • Square Feet 1,624
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1984

BEST AND FINAL TUESDAY 7/15 5PM. Investors Take Notice! Endless potential awaits in this 3-bedroom, 1.5-bath home with an attached 2-car garage. Whether you're looking to renovate, flip, or hold as a rental, this property offers unlimited possibilities. Bring your vision and transform this space into something truly special! Estate is subject to probate approval, and property just came out of foreclosure. AS-IS, some contents may be removed prior to closing.

Listed by Lisa A. Barstow of Simply Sold Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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34 S Windham Road Windham CT 06226

Windham, CT34 S Windham Road

Price$244,900

Est. Mortgage: $/month

Coming Soon

MLS Number 24111511

  • Single Family
  • Square Feet 1,156
  • Bedrooms 3
  • Bathroom 1
  • Year Built 1915

Welcome to 34 South Windham Road! Whether you're a first-time homebuyer or looking to downsize, this charming, well-maintained home is move-in ready and full of thoughtful updates. Step inside to find new flooring in the living room and bedrooms, a fresh coat of paint throughout, a new roof and boiler, and a recently updated rug in the spacious downstairs extra room. The lower level features a fully finished family/rec room with a closet-ideal for relaxing, entertaining, or even a guest space. Outside, enjoy your morning coffee or evening unwind on the cozy front patio. Every detail has been handled with care and pride, making this home truly turn-key. Be sure to check out the photos and virtual tour-this is one you don't want to miss!

Listed by Stephen Girouard of CENTURY 21 Shutters & Sails

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$
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$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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 24109877

  • Multi Family Multi-Family For Sale
  • Square Feet 2,548
  • Acreage 0.42
  • Bedrooms 5
  • Bathroom 1

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 side-by-side duplex or be converted to a single-family residence. Each unit features its own living space, making it suitable for an owner-occupant with rental plans or a full investment property. The basement offers additional storage or workshop options. The versatile layout also includes covered side porches for each unit, a shared back deck providing additional outdoor living space, a practical storage shed, and an oversized one-car garage that could easily accommodate two vehicles. Property sold AS IS.

Listed by Franchesca M. Pescatello of Prue Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.72% last updated on Jul 10, 2025
* 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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The data relating to real estate for sale on this website appears in part through the SmartMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SmartMLS through a licensing agreement. Listing information is from various brokers who participate in the SmartMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2025 SmartMLS, Inc.