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$485,000
9 Beds ⋅ 5 Baths ⋅ 24099416 MLS
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!

4 Main St, Windham

$395,000
3 Beds ⋅ 2 Baths ⋅ 24159990 MLS
Charming New England Cape offering the perfect blend of timeless character and modern updates. Set on a nice-sized lot with a private yard, this beautifully maintained home features thoughtful renovations while preserving its original charm. The bright updated kitchen showcases white cabinetry, granite countertops, new stainless steel appliances, and fresh paint, creating a clean and inviting space for everyday living. The home also features fully renovated bathrooms and fresh paint throughout. A standout feature is the spacious family room with vaulted ceilings, built-in window seats, and a cozy wood-burning stove, providing a warm and inviting gathering space. Classic New England character continues throughout the home with a fireplace and charming original details. The layout offers flexibility with a first-floor ensuite bedroom, while the second level features two additional bedrooms and a second full bath. Additional highlights include a newer roof, newer vinyl siding, and a two-car garage. Step outside to enjoy the private backyard with patio and deck, perfect for relaxing or entertaining. This beautifully updated Cape combines historic charm with modern comfort, offering a warm and welcoming home in a peaceful South Windham setting. Interior Photos and floor plans will be available soon -

128 Machine Shop Hill Rd, Windham

$321,600
3 Beds ⋅ 1 Baths ⋅ 24161495 MLS
OFFER DEADLINE MON 5:00PM. Tucked into the countryside of South Windham, this move-in-ready 1,423-square-foot home offers a wonderful blend of country living and modern practical updates. Completely refreshed from top to bottom-including the peace of mind of all new plumbing-the house sits on a beautiful, level lot featuring quiet water views, giving you a sense of rural escape while staying just a short drive from local shopping and restaurants. The heart of the home is the bright, updated kitchen, which features durable granite countertops, all-new appliances, and a cozy breakfast nook framed by an oversized bay window. New, high-quality composite flooring flows throughout the main level for a seamless look that is both stylish and easy to maintain. The comfortable layout includes a convenient main-floor bedroom and a remodeled bathroom that features handy laundry access to simplify your daily routine. The living room has also been fully updated and is anchored by its own large bay window that fills the space with natural light. Upstairs, the primary bedroom feels airy and bright with its vaulted ceiling and classic Palladian window, while a third well-appointed bedroom completes the second floor. From the new roof, fresh finishes, to the tranquil outdoor setting, every part of this property has been handled with care to create a welcoming, turnkey home. This is a fantastic opportunity to own a fully updated sanctuary in a great location-schedule your private tour toda

170 Windham Center Rd, Windham

$249,000
2 Beds ⋅ 2 Baths ⋅ 24128966 MLS
Welcome to 10 North Road in the heart of historic Windham Center! This charming 2-bedroom, 1.5-bath home blends timeless character with tasteful updates, offering both comfort and convenience. Step inside to find a light-filled living space and an additional room on the first floor that's perfect for a home office, den, or guest space. The thoughtfully updated kitchen and fresh paint throughout make the home move-in ready while preserving its classic New England charm. Outside, enjoy a peaceful backyard and the convenience of a detached garage-ideal for a workshop, studio, or extra storage. Situated right in the center of Windham's historic district, you'll love the sense of community and the easy access to local shops, dining, and commuting routes.

10 North Rd, Windham

$190,000
4 Beds ⋅ 2 Baths ⋅ 24164604 MLS
*** Dutch Colonial Style Home Brimming with History and Potential *** This home is the former parsonage for St. Paul's Episcopal Church, with many antique features reminiscent of its time - gambrel style roof, colonial American style woodwork, wide plank floors, field stone foundation and walk ways, and accretive architecture. The home is sprawling with over 2700 Sqft, 4 bedrooms, 1 1/2 baths, large mud/laundry room, spacious eat-in kitchen, and large, lower level workshop area with natural lighting. It is steps away from historic Windham Center and Town Green, and is surrounded by other beautiful antiques homes. Per town record New gas line (2020), new stainless steel chimney liner (2020), new oil hot air furnace (2019), and oil tank (2015). Cash, conventional or rehab loans only. Home is in a historic district, rules and regulations can be found at the Town of Windham website. ***This is an estate sale, subject to probate court approval. Buyer to do due-diligence. Being sold in AS-IS/WHERE-IS including personal property ***

26 Plains Rd, Windham

$160,000
5 Beds ⋅ 1 Baths ⋅ 24109877 MLS
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.

33 Machine Shop Hill Rd, Windham

$115,000
2 Beds ⋅ 1 Baths ⋅ 24128851 MLS ⋅ Cedar Crest BLDG.
Discover affordable living in this charming 1st-floor, 2-bedroom, 1-bath ranch-style condo-own for less than renting! Nestled in a prime location, this home offers easy access to UCONN and Route 6, with Boston just under 2 hours away. The inviting eat-in kitchen features ample storage and generous counterspace, ideal for meal prep and entertaining. The spacious living room boasts modern recessed lighting and elegant bamboo floors, creating a warm and welcoming atmosphere. Two well-sized bedrooms provide excellent closet space for all your storage needs. Step outside to enjoy the convenience of an outdoor storage shed, perfect for seasonal items or extra gear. This low-maintenance condo combines comfort, style and practicality, making it an excellent choice for first-time buyers or those looking to downsize. With its unbeatable location and move-in-ready condition, this home offers the perfect opportunity to enjoy the benefits of homeownership without the high costs of renting. Don't miss out on this fantastic value-schedule a showing today and see why this condo is the ideal place to call home!

270 S Windham Rd Unit APT 53, Windham

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