Winchendon Real Estate

Welcome to Winchendon, Massachusetts – a hidden gem nestled in the heart of Worcester County. Known for its rich history and charming small-town atmosphere, Winchendon offers a unique blend of rural beauty and vibrant community life. With a population of just over 10,000, this picturesque town is perfect for those seeking a peaceful retreat while still being within reach of urban amenities.

Winchendon is steeped in history, with roots dating back to the late 18th century. Stroll through the town’s historic district, where you’ll find beautifully preserved architecture that tells the story of its past. The town is also home to several parks and recreational areas, including the stunning Winchendon State Forest, which offers hiking trails, scenic views, and opportunities for wildlife observation.

For families, Winchendon boasts a strong sense of community, with excellent schools and numerous local events throughout the year, from farmers’ markets to seasonal festivals. The town’s warm and welcoming atmosphere makes it easy to forge lasting connections with neighbors.

In addition to its natural beauty and community spirit, Winchendon is conveniently located near major highways, providing easy access to nearby cities like Worcester and Boston. Whether you’re looking for a cozy starter home, a spacious family residence, or a charming cottage, Winchendon has a diverse array of real estate options to suit your needs.

Discover the charm of Winchendon, where history meets modern living, and find your perfect home in this delightful Massachusetts town.

Newest Listings in Winchendon

$1,050,000

3 Beds ⋅ 3 Baths ⋅ 73576032 MLS

Summer isn’t over yet - and lake life is calling! This one-of-a-kind Lake Monomonac property offers something almost unheard of for waterfront: nearly TWO acres, over 2,000 sq. ft. of living space and FIVE garage stalls, all on one of the area’s most desirable lakes. Inside, enjoy radiant heat throughout - even in the basement - and hardwood floors throughout. A tiled entry with half bath and laundry leads to a first-floor primary retreat with a spacious walk-in closet and full bath. The heart of the home is the open-concept kitchen, living and dining area, featuring brand-new Quartz counters, a custom handmade backsplash and two NEW French doors opening to the wraparound deck with beautiful views of the yard and lake. Entertain, unwind or head to the above-ground pool - the hardest decision may be pool or lake! Upstairs are two generous bedrooms, one with a double closet and the other with a walk-in, and a large full bath. The full basement offers excellent workshop space, while the attached heated 3-car garage and detached 2-car garage, built in 2022, provide an incredible amount of room for vehicles, boats, toys and hobbies. Tesla solar helps keep electric costs down, too, plus there's a generator for added peace of mind! Nearly two peaceful acres, room to spread out and the lake right outside your door - there’s still plenty of summer left to start living the Lake Monomonac life!

36 Monomonac Rd W, Winchendon

$464,900

3 Beds ⋅ 3 Baths ⋅ 73574967 MLS

Newly built and ready to welcome its first residents. This new home offers the promise of modern living within a peaceful setting. The residence features three bedrooms, providing comfortable accommodations for rest and relaxation. Two full bathrooms and one-half bathroom offer convenience and functionality, ensuring that the needs of everyday living are met with ease and style. With a living area of 1400 square feet, the home provides a practical and inviting space for both intimate gatherings and quiet moments of reflection. The ample lot size of 1.05 acres offers a sense of openness and connection with nature. This single-family residence is a fantastic opportunity to create the lifestyle you have always desired.

Lot 1 River St, Winchendon

$425,000

2 Beds ⋅ 2 Baths ⋅ 73574438 MLS

Welcome to this exceptional, updated Ranch with an 19x52 heated garage with space for a workshop, recreational vehicles, & more! This home features a newly finished lower level, offering an inviting and sophisticated extension of the home’s living space. On the main level, everyone will want to gather around the island in this spacious kitchen, with updated cabinets and a granite island countertop. The generous dining area also provides additional space for lingering meals and entertaining. The large living room with the tiled fireplace, provides comfort, as well as space, for everyone to enjoy time together. This bright and cheery home has 2 bedrooms and a full bathroom on the main floor. The entertainment room, in the thoughtfully designed lower level, has a beautifully tiled pellet stove surround, creating a striking focal point to this room. It is complete with a two tiered custom wood slab bar, wet bar & a full fridge. The office/guest room has ample space to accommodate a variety of needs. The stunning bathroom with shower completes this impressive addition. All work is fully permitted! The expansive level backyard provides room to gather, play, garden etc. Two sheds provides storage for yard supplies and outdoor equipment. The garage has a new roof, new epoxy floor, newly painted interior, new heater, and upgraded electrical 100 Amp panel. New exterior garage soffit lights create an outside ambience as well as lighting to the home side door entrance. This home has all new: recessed kitchen lights, 200 AMP Panel, security cameras, flood lights, solar panels, and a whole house water filtration system. The home roof is approx. 5 years old. This property is in a Home Business Zone (town approval required). This meticulously maintained, beautiful home is worry free and ready for you to move in! First showing at OH 9/12/26.

125 Baldwinville State Rd, Winchendon

$399,900

4 Beds ⋅ 2 Baths ⋅ 73571805 MLS

There’s something special about a Village Colonial: the character, the generous rooms and the feeling of being connected to the heart of town. Welcome to 374 Front Street, where you’ll find all of that, plus a floor plan with plenty of room to make it your own. The spacious 15x15 eat-in kitchen, with newer appliances and hardwood floors, is made for morning coffee, weeknight dinners and conversations around the table. A separate dining room gives you great space to celebrate holidays and gatherings, while the oversized 21x15 living room offers plenty of space to gather and relax. Need flexibility? A first-floor bedroom/separate office create options for guests, working from home, a playroom or hobby space, plus additional open space between the dining room and living room. Upstairs are three more generously sized bedrooms, including a 15x14 primary bedroom and a 13x13 bedroom with a walk-in closet. Wood floors (mix of hardwood, Douglas Fir and Pine) run throughout much of the home, and second-floor laundry keeps everyday chores conveniently close to the bedrooms. Outside, enjoy a level backyard with room for gardening, games, summer cookouts or simply relaxing at home. The porch adds another spot to sit back and enjoy the neighborhood, while the newer 2024 roof is an important update already taken care of. Best of all, you’re close to the heart of Winchendon, with local shops, dining, Beals Memorial Library and community activities nearby. Outdoor adventures are easy to find too, from the North Central Pathway and Winchendon Community Park to nearby Lake Dennison and Otter River. If you’ve been waiting for a home with character, space to spread out and the convenience of village living, this one deserves a closer look.

374 Front Street, Winchendon

$385,000

4 Beds ⋅ 2 Baths ⋅ 73571155 MLS

A true diamond in the rough, this home has great bones, great space, and a lot of potential for a variety of prospective buyers. Situated conveniently on Tannery Pond, only a few minutes to downtown Winchendon, this property is zoned for a two family but currently being used as a single family. All systems - heat, hot water, and electric - are in great shape. Worry-free solar panels are owned, not leased. A recent renovation to the kitchen has added value, but there is much more opportunity to live comfortably yet build more equity. This house has amazing possibilities, and as a single home or a duplex allows for a rare vesatility for a new owner. Schedule a showing today!

33-35 Beech St., Winchendon

$489,500

2 Beds ⋅ 3 Baths ⋅ 73570387 MLS

Discover the allure of 736 Central St. in Winchendon, MA, a charming single-family log home built in 1994 offering 1481 square feet on two levels of thoughtfully designed living space and approximately 360 sq/ft of mostly finish living space in basement with 1/2 bath. This property presents an open floor plan with loft living area, a good size heated family/4 season room. The home features a 34x8 farmers porch for your enjoyment and relaxing with a swing, two inviting bedrooms and a loft area providing additional personal space for your needs and imagination, perhaps a home office. Complementing these are a full bathroom and an additional half bathroom, ensuring convenience for both residents and guests. The first floor half bath has hookups for a full size washer and dryer for added convenience. Kitchen boasts a walkin pantry for added storage. Set on an expansive 2.05 acre lot, the property offers generous outdoor possibilities. A newer heated and well-insulated two-car garage provides practical storage and protection for vehicles along with rear garage door opens to service part of basement along with 2 storage sheds. This is more than a house; it's a foundation for your future memories. We invite you to explore the possibilities of making this exceptional property your own. For all you snowmobile and hiking enthusiasts, there is acess to a Rail Trail that goes into New Hampshire and beyond or near by Lake Monomonac. While being situated in a quiet, private spot, you're just a 3 minute drive from the downtown area. This home comes with gas-fiired electric gererater and whole house connection. Some photos are before furniture was removed. It's ready to go and a quick closing is possible.

736 Central St., Winchendon

$325,000

3 Beds ⋅ 1 Baths ⋅ 73562707 MLS

OFFER DEADLINE OF WEDNESDAY, SEPTEMBER 2ND AT 6:00 P.M. Charming single level residence in tranquil setting! This inviting property, built in 1950, consists of three bedrooms, one full bath, family room, living room and eat-in kitchen set on 1.03 acres of land. An enclosed porch provides a relaxing setting with which to enjoy the private backyard. A paved driveway leads to the single car garage, providing storage options for car or "stuff". Most windows are insulated replacement units. Serviced by public water - new septic system being installed right now! Original owners made many happy memories here! Make this house your HOME!

262 West Street, Winchendon

$309,900

3 Beds ⋅ 1 Baths ⋅ 73568813 MLS

Come on out and be the first to see this new to market 3 bedroom ranch with more than 5 private acres. 173 Baldwinville Rd in Winchendon, MA this home was constructed in 1973, offering 1092 square feet of meticulously designed living space. This property represents a unique opportunity for those seeking acreage, privacy and combined with comfortable residential living. The residence provides three well-appointed bedrooms, each designed to offer privacy and comfort. Complementing the living quarters is a full bathroom, thoughtfully integrated to serve the needs of the household. Encompassing an expansive 252,648 square feet, the property's lot offers unparalleled potential for outdoor pursuits, expansion, or simply enjoying vast open spaces. We invite you to schedule a private viewing to fully appreciate the potential and serene setting of this exceptional offering. Seller has been using the 3rd bedroom as a dinning room but can be reverted back to a bedroom with relative ease. The past owner had livestock on the property and with minimal effort the property could be reverted back

173 Baldwinville Rd, Winchendon

$409,900

3 Beds ⋅ 2 Baths ⋅ 73568807 MLS

Welcome home to this beautifully renovated property in Winchendon! Completely transformed with thoughtful updates throughout, this inviting home offers a fresh, modern feel while maintaining plenty of warmth and charm. Soaring ceilings and luxury vinyl flooring create a bright, spacious atmosphere, while the updated kitchen features beautiful quartz countertops and stainless steel appliances.The home offers two beautifully finished full bathrooms—one conveniently located on the first floor and a second adjoining the primary bedroom on the second floor. With stylish finishes, comfortable living spaces, and extensive renovations already complete, all that's left to do is unpack and settle in.Beautifully updated and truly move-in ready—come see all this Winchendon home has to offer!

16 Winter Pl, 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

$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

$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

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