Winchendon Homes for Sale

Welcome to Winchendon, Massachusetts – a charming town nestled in Worcester County that beautifully blends small-town charm with modern conveniences. Known for its rich history and picturesque landscapes, Winchendon offers a serene escape with a vibrant community spirit. With a population of just over 10,000 residents, this tight-knit town is perfect for families, retirees, and anyone seeking a tranquil lifestyle amidst nature’s beauty.

Winchendon is renowned for its stunning natural surroundings, including the breathtaking Lake Monomonac, where residents can enjoy boating, fishing, and picnicking. The town boasts a variety of recreational activities, including hiking trails and parks that cater to outdoor enthusiasts. For those who appreciate arts and culture, Winchendon also features historical landmarks and community events that celebrate its heritage.

When it comes to homes for sale, Winchendon has something for everyone. Whether you’re seeking a cozy cottage, a spacious family home, or a charming Victorian, the real estate market here offers a diverse array of options to fit your lifestyle and budget. Homes in Winchendon often feature beautiful yards, modern amenities, and easy access to local shops and schools, making it an attractive choice for prospective buyers.

With its welcoming atmosphere and a strong sense of community, Winchendon is not just a place to live; it’s a place to call home. Explore the current listings and discover the perfect property to start your next chapter in this delightful town. Your dream home awaits in Winchendon!

Newest Winchendon Homes for Sale

$239,900

3 Beds ⋅ 2 Baths ⋅ 73567741 MLS

This antique Colonial offers a unique opportunity for buyers looking to restore a classic New England home with character and potential. Tucked away at the end of a dead-end street and located near a walking trail and pond, the property offers a peaceful setting with added privacy. The home features 3 bedrooms, 2 full bathrooms, vaulted ceilings on the second floor, and a flexible first-floor layout including a kitchen with dining area, living room, dining room, family room, laundry room, and full bath. There is a 7 day minimum offer hold period for all buyer types.

58 Emerald St, Winchendon

Listing courtesy of Listing Agent: The Ponte Group from Listing Office: Keller Williams South Watuppa.

$79,900

3 Beds ⋅ 4 Baths ⋅ 73566794 MLS

Investors & Contractors take notice! Listed below the assessed value, this unique early-1900s property in Winchendon offers an opportunity to bring your vision and creativity to a property in need of a complete rehabilitation. Restore and reimagine this distinctive property overlooking Tannery Pond and abutting Tannery Pond Dam, a historic masonry dam completed in 1936. Zoned PD (Planned Development), the property offers potential for a variety of residential and/or commercial uses, subject to buyer verification with the Town of Winchendon. Possibilities may include a business or commercial use on the first floor with residential space above, a multi-family conversion, or a single-family residence. Conveniently located just minutes from the Ware River Rail Trail and area amenities. Electricity is currently on; due to the property's condition, showings are recommended during daylight hours.

4 Front Street, Winchendon

Listing courtesy of Listing Agent: Kellie McElhinney from Listing Office: Central Mass Real Estate.

$249,900

3 Beds ⋅ 1 Baths ⋅ 73566543 MLS

CLASSIC NEW ENGLAND VILLAGE COLONIAL - NEW TO THE MARKET & PRICED TO SELL!! LOVELY COVERED PORCH LEADING TO THE SPACIOUS LIVING ROOM WITH GAS STOVE, DINING ROOM, KITCHEN WITH REFRIGERATOR AND STOVE AND FULL BATH ON THE FIRST FLOOR. 3 BEDROOMS ON THE 2ND LEVEL. MUNICIPAL WATER AND SEWER. CONVENIENT ACCESS TO SCHOOLS, PARK, AND DOWNTOWN. QUICK CLOSING POSSIBLE. THIS PROPERTY IS BEING SOLD AS-IS. OFFER DEADLINE SUNDAY 8/23 @ 6 P.M.

160 Mill Street, Winchendon

Listing courtesy of Listing Agent: Gail Bergeron from Listing Office: Keller Williams Realty North Central.

$250,000

2 Beds ⋅ 1 Baths ⋅ 73563755 MLS

Whether you're a contractor looking for your next project or a home buyer searching for affordable one-level living, this adorable 2-bedroom ranch is packed with potential...subdivision potential! Enter through the enclosed porch, filled with natural light, and into an open kitchen featuring a walk-in pantry with plenty of storage. The spacious living room offers room to relax, while both bedrooms include closets. The full bath features a charming cast iron clawfoot tub, and main-floor laundry makes everyday living easy. The home is also serviced by town water and sewer! Outside, a large shed provides additional storage. What really sets this property apart is the land - with frontage on two streets and potential for future subdivision, with approximately 2-4 additional lots potentially possible. Bring your ideas and see just how much opportunity this property has to offer!

21 Munroe St, Winchendon

Listing courtesy of Listing Agent: Olivia Paras from Listing Office: LAER Realty Partners.

$390,000

4 Beds ⋅ 1 Baths ⋅ 73563203 MLS

OPEN HOUSE Saturday 8/15 NOON to 2pm!! Welcome home to this sun-filled, open-concept home! The bright first-floor living space features hardwood floors and a picturesque window that flows seamlessly into the eat-in kitchen with ample cabinet storage. Head right into the family room featuring a vaulted ceiling and a stunning picture window overlooking your serene backyard. Down the hallway, you’ll find two comfortable bedrooms and a full bath. The fully finished lower level adds incredible living space, offering two additional bedrooms and a versatile bonus room—perfect for a home office, gym, or playroom! Head outside to your private, wooded backyard complete with a patio, convenient storage shed, and an inground pool perfect for summer fun. Whether relaxing in your private backyard sanctuary or exploring nature at the nearby Monomonac Hill Conservation Area, this property offers the perfect mix of comfort and outdoor adventure! Peace of mind comes with a brand new roof and brand new 4 bedroom septic system! Your private backyard paradise awaits—schedule your showing today and start making memories!

114 Glenallen Street, Winchendon

Listing courtesy of Listing Agent: Edwin Ahearn from Listing Office: Lamacchia Realty, Inc..

$359,000

3 Beds ⋅ 1 Baths ⋅ 73562470 MLS

Welcome to this beautifully renovated 3-bedroom, 1-bath ranch offering the perfect blend of modern updates and comfortable single-level living. Set on three parcels totaling over an acre, this property provides plenty of space and privacy while offering a move-in-ready home.Inside, you'll find refinished hardwood floors throughout and fresh paint creating a bright, inviting feel. The brand-new kitchen features quartz countertops, new cabinetry, stainless steel appliances, and stylish new tile flooring. The updated bathroom includes a double vanity and modern finishes.Major improvements include a newer roof, brand-new septic system, and completely updated plumbing and electrical systems, providing peace of mind for years to come. The large, open basement offers excellent storage and future potential, along with new laundry hookups.With extensive renovations already completed, this home is ready for its next owner to simply move in and enjoy. A rare opportunity to own a fully updated ranch with over an acre of land! OPEN HOUSES CANCELED for the weekend!

399 Maple St, Winchendon

Listing courtesy of Listing Agent: Sara Garcia from Listing Office: Coldwell Banker Realty - Leominster.

$325,000

4 Beds ⋅ 2 Baths ⋅ 73559752 MLS

Tucked into the heart of Winchendon, this inviting 2-bathroom, possible 4-bedroom home offers 1,465 square feet of warm, character-filled living space. Your first impression starts before you even step inside—the classic farmer's porch is the kind of spot made for enjoying morning and evening porch-sitting. Cross the threshold, and you're greeted by beautiful hardwood floors that make the home feel warm and inviting. The first-floor bathroom has been beautifully remodeled with a fresh, modern touch and features heated floors for added comfort. The first floor has high ceilings and tile flooring, making it perfect for a playroom.Upstairs, you will find a clawfoot tub and three rooms with wall-to-wall carpeting. One of the rooms does not have a closet, making it perfect for a home office.Outside, enjoy a small, level, fenced-in yard that's perfect for relaxing. Three off-street parking spots add everyday convenience that's hard to find in town. Did I mention the generator hookup, providing essential power when the electricity goes out?

10 Jackson Ave., Winchendon

Listing courtesy of Listing Agent: Kenton Jacobs from Listing Office: Real Estate Exchange.

$429,000

3 Beds ⋅ 3 Baths ⋅ 73554607 MLS

Newer constriction with DEEDED BEACH RIGHTS to Sunset Lake. Rear boundary borders thousands of conservation acres with endless ATV and snowmobile trails. Seasonal views of the lake. Town water! 3 BD + office, 2 ½ baths house with DEEDED BEACH RIGHTS to Sunset Lake. Master BD with master bath. Good size kitchen and dinning room. Washer/dryer (hook up) on the 1st floor. Ashburnham mailing address but Winchendon public schools. Use Ashnburnham for GPS

33 W Shore Drive, Winchendon

Listing courtesy of Listing Agent: Roman Deych from Listing Office: Roman Deych.

$599,900

3 Beds ⋅ 3 Baths ⋅ 73544803 MLS

Immaculate, like new 1,828 sq. ft. colonial set on a private 4.13 acres. Welcome to 90 Royalston Road. Step inside to an inviting open-concept floor plan featuring a spacious kitchen with granite countertops, stainless steel appliances, an island, and cabinets with crown molding, a formal dining room, a front-to-back living room and a half bath with laundry. A slider off the kitchen leads to a private deck overlooking the above-ground pool and beautiful backyard. Upstairs, the front-to-back primary suite features a walk-in closet, linen closet and a private full bath. Two additional generously sized bedrooms and a full bath complete the second floor. Additional features include a two-car attached garage and central air. Enjoy peaceful country living just minutes from downtown, shopping, and restaurants. Welcome Home!

90 Royalston Rd N, Winchendon

Listing courtesy of Listing Agent: Tessa Parziale Rigattieri from Listing Office: Tessa Parziale Real Estate.

$444,000

5 Beds ⋅ 3 Baths ⋅ 73530513 MLS

Step into a piece of Winchendon's rich history at 155 River St, a distinguished single-family residence built in 1890. With over 2000 square feet of thoughtfully designed living space, this home offers a unique blend of classic charm and contemporary comfort, perfect for those seeking a vibrant lifestyle. This expansive home features five well-proportioned bedrooms, providing ample private space for residents and guests alike. The three full bathrooms are placed for convenience and comfort. Set on a generous 16,335 square foot lot, the property offers an outdoor area for relaxation, recreation, or gardening pursuits. A single-car garage provides practical storage and parking solutions. Discover the unique character and endless possibilities of this remarkable Winchendon address.

155 River St, Winchendon

Listing courtesy of Listing Agent: Tina Keith from Listing Office: Leading Edge Real Estate.

$539,000

3 Beds ⋅ 3 Baths ⋅ 73520335 MLS

BUYER OPPORTUNITY! Seller is offering up to $5,000 toward buyer closing costs! Move-in ready Colonial - privately set on 1.28 acres in one of Winchendon's desirable neighborhoods. Located on a cul-de-sac with just 3 homes, this property offers privacy, mature landscaping, perennial gardens and great curb appeal. A welcoming wraparound farmer's porch leads into a sun-filled interior with hardwood floors throughout. The living room features a gas fireplace, plus there is a separate front-to-back family room that provides plenty of additional space to relax or entertain. The eat-in kitchen offers granite countertops, a center island, breakfast bar and newer stainless steel appliances. This area has access to the back deck overlooking the private yard and a small fenced-in area. Upstairs you'll find 3 bedrooms, including a spacious primary suite entered through French doors and featuring a walk-in closet & private full bathroom. Convenient 2nd-floor laundry completes the upper level. The lower level includes a partially finished craft/flex room. Other highlights include an attached 2-car garage, a shed, Buderus heating system, 2021 roof and town water & sewer. Seller relocating for work and quick closing is available. Seller will contribute up to $5,000 toward buyer closing costs with an acceptable offer closing by September 30, 2026. Easy to show!

6 Loon Road, Winchendon

Listing courtesy of Listing Agent: Cory Gracie from Listing Office: LAER Realty Partners.

$309,900

3 Beds ⋅ 1 Baths ⋅ 73461917 MLS

Well maintained 3-bedroom home in a great location. Bright and sunny 1st floor with a large living room. Spacious kitchen. Extra room for office space or den. 3 full-sized bedrooms. Beautiful full bath. New septic. Move right in and start the new year in your new home. Seller willing to buydown the mortgage rate of this home. One-year American Home Shield Warranty included. PLEASE SET UP APPTS THRU SHOWINGTIME.

16 Maple Place B, Winchendon

Listing courtesy of Listing Agent: Bob DeVito from Listing Office: Cameron Real Estate Group.

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