Winchendon Real Estate

Welcome to Winchendon, Massachusetts – a charming town nestled in the heart of Worcester County, where small-town charm meets vibrant community spirit. Known as the "Cranberry Capital of the World," Winchendon boasts a rich history and an abundance of natural beauty, making it an ideal place to call home.

With a population of just over 10,000 residents, Winchendon offers a close-knit community atmosphere while still providing easy access to larger urban centers. The town is characterized by its picturesque landscapes, featuring lush forests, serene lakes, and scenic hiking trails. For outdoor enthusiasts, Lake Monomonac is a local gem, perfect for swimming, fishing, and boating during the warm months, while the surrounding woodlands invite exploration year-round.

Winchendon is steeped in history, with charming architecture that tells the story of its past. The town's vibrant downtown area is home to unique shops, delightful eateries, and community events that foster a sense of belonging among residents. The Winchendon School, a prestigious private institution, adds to the town's educational offerings and enhances the cultural landscape.

Families will appreciate the strong emphasis on community and education, with well-regarded schools that prioritize student growth and development. Additionally, Winchendon’s convenient location near major highways makes commuting to nearby cities like Worcester and Fitchburg a breeze.

Whether you're seeking a peaceful retreat or a place to grow your family, Winchendon offers a warm welcome and a wealth of opportunities. Come discover your new home in this delightful Massachusetts town, where every day feels like a breath of fresh air!

Newest Listings in Winchendon

$225,000

73568045 MLS

This .69 Acre lot is located near the center of town and has direct access onto Central Street. Perfect for an investor who would develop it into one of the many allowed uses for the land. Uses include a 5 unit condominium buildng, apartments, retail store, convenience store with gas station, restaurant, wireless communications, solar energy collection to name a few. The GIS map, Property Card and table of uses are attached to the listing for reference.

2 Juniper St, Winchendon

Listing courtesy of Listing Agent: Scott Simpson from Listing Office: Century 21 North East.

$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.

$415,000

6 Beds ⋅ 1 Baths ⋅ 73566413 MLS

Excellent opportunity to own a spacious two-family home with the added benefit of rental income. The 1st unit offers three-bedrooms, full bath, a comfortable living room, dining area, and generously sized kitchen with access to the back porch. The second unit features two bedrooms, a full bath, living and dining areas, and a functional kitchen. Both units have separate heat and electricity, also access to basement storage. Additional it includes a fenced backyard, detached garage, and off-street parking. Conveniently located near the town center and local amenities. A great option for owner-occupants or investors!

19- 21 East St, Winchendon

Listing courtesy of Listing Agent: Barbara Gutierrez from Listing Office: Forsley Real Estate.

$499,000

73564528 MLS

Bring your business vision to this highly visible location along the Route 140 corridor! With approximately 400 feet of road frontage and an estimated 11,000 vehicles passing by each day, according to MassDOT, this property offers excellent exposure and plenty of potential for roadside signage and business identification, subject to Town approval. The property is conveniently located approximately 315 feet from the Route 12/Route 140 junction and less than 13 miles from Route 2, providing easy access to downtown Winchendon, Gardner, northern Worcester County, and southern New Hampshire. Three-phase power and access to municipal water add to the possibilities. Zoned C-1 (Large-Scale Commercial), the property may support many types of commercial uses, including retail, a convenience store, restaurant,, professional offices, financial institution, car wash, movie theater, and more. The Town’s Zoning District Use Table also notes the possibility of residential development. The property contains harvestable timber, and the owner would like to retain the timber rights. Buyers and buyers’ agents should confirm their proposed use, signage plans, utilities, zoning requirements, and all necessary permits and approvals with the Town of Winchendon.

Lot 187 Gardner Rd, Winchendon

Listing courtesy of Listing Agent: Liza M. Melo from Listing Office: Four Columns Realty, LLC.

$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..

$445,000

5 Beds ⋅ 3 Baths ⋅ 73563079 MLS

Welcome to 142 Pleasant St! This spacious two-family home offers 5 bedrooms, 2.5 baths, and a versatile layout. Recent updates include refinished hardwood floors, new interior paint throughout, restored carpentry, updated light fixtures, and major electrical improvements. The kitchen features new quartz countertops and new appliances, while bathroom updates include new vanities and toilets. The third level includes a bonus room and bedroom, providing even more usable space. A two-level garage adds another unique feature, with a second floor, its own egress, and plenty of possibilities. Unit 2 is located on the second floor including 1 bedroom, living room, updated bathroom and updated kitchen with quartz countertops. Conveniently located near the center of Winchendon, with shops, dining, and local amenities nearby, along with the North Central Pathway, Whitney Pond, and Lake Dennison State Recreation Area. This property has character, thoughtful updates, flexible space, and plenty of potential for its next owner.

142 Pleasant St, Winchendon

Listing courtesy of Listing Agent: Noelle Medugno 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.

$418,000

6 Beds ⋅ 2 Baths ⋅ 73558512 MLS

Seller is now offering a $15,000 buyer closing-cost credit! This closing cost credit may be used toward eligible closing costs, prepaid expenses, or an interest-rate buy-down—helping qualified buyers reduce their upfront costs or potentially lower their monthly payment! 263 Front St. is a well-maintained two-family home offering the perfect blend of charm, space, and investment potential. Each expansive unit features 3 bedrooms, bright and inviting living areas, spacious kitchens, and an abundance of natural light, creating comfortable spaces for both owners and tenants alike. Thoughtfully updated over the years, including two brand-new boilers installed in 2026, this property offers the ideal opportunity for an owner-occupant seeking supplemental rental income or an investor looking to add a turnkey duplex to their portfolio. Ideally situated in a convenient in-town location close to shopping, dining, schools, parks, and commuter routes, this versatile property delivers both lifestyle and long-term value. Whether you're starting your investment journey or growing an established portfolio, this is a property you'll want to see.

263 Front St., Winchendon

Listing courtesy of Listing Agent: Leanne Roy from Listing Office: Keller Williams Realty North Central.

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