Winchendon Homes for Sale

Welcome to Winchendon, Massachusetts—a charming town nestled in the heart of Worcester County, where small-town charm meets modern convenience. Known for its picturesque landscapes and rich history, Winchendon offers a delightful blend of rural tranquility and vibrant community life. With its beautiful lakes, lush forests, and scenic views, outdoor enthusiasts will find plenty of opportunities for hiking, fishing, and exploring nature.

Winchendon boasts a welcoming atmosphere, highlighted by its friendly residents and strong community spirit. The town is home to various local events and festivals throughout the year, where neighbors come together to celebrate and enjoy the vibrant culture. Families will appreciate the excellent school system and the abundance of recreational activities available for children and adults alike.

For those considering a move to this idyllic town, there are a variety of homes for sale that cater to different lifestyles and budgets. From charming historic homes that exude character to modern new builds equipped with the latest amenities, Winchendon has something for everyone. Whether you’re looking for a cozy cottage or a spacious family home, you’ll find properties that meet your needs while allowing you to enjoy the beauty of the surrounding area.

With its unique blend of history, community, and natural beauty, Winchendon is not just a place to live; it's a place to thrive. Explore the homes for sale in this delightful town and discover the perfect setting for your next chapter. Your dream home in Winchendon awaits!

Newest Winchendon Homes for Sale

$307,000

2 Beds ⋅ 2 Baths ⋅ 73595357 MLS

Just in time for Halloween! Welcome to 23 Webster Street in Winchendon, MA. This Colonial-style home offers a practical layout, inviting living spaces, and plenty of opportunity to make it your own. The first floor features a spacious kitchen, comfortable living room, full bathroom, and versatile bonus room suitable for a home office, dining room, or additional living area. Upstairs are two bedrooms, including a primary bedroom with its own bathroom. Hardwood flooring adds character to the first-floor living areas, while the full unfinished basement provides additional storage and potential for future projects. Solar panels offer an alternative energy feature. Be sure to look for the pumpkin-head appearances throughout the listing photos! They add a touch of Halloween fun, but this home is the real treat.OPEN HOUSE — HALLOWEEN!Saturday, October 31 | 11 AM–1 PMStop by, explore the property, and see whether this home is the treat you’ve been searching for!

23 Webster St, Winchendon

$2,700

3 Beds ⋅ 2 Baths ⋅ 73594331 MLS

This beautifully renovated property in Winchendon is available for rent! 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! Seller will negotiate a Rent to Buy option.

16 Winter Pl, Winchendon

$350,000

3 Beds ⋅ 3 Baths ⋅ 73592554 MLS

Charming colonial with all the character that reflect it's 1920's origin. Entering the front door into the spacious living room with hardwood floor, fireplace, pellet stove insert and an office area tucked into an alcove. The dining room features french doors and hardwood floor, with a pantry/butler passthrough to the kitchen. A sunny dining nook and breakfast bar are part of it's functional layout. A half bath is just off the kitchen. A home office with separate entrance and half bath encompasses the addition. On the second floor, you will find four bedrooms, with the master featuring a large walk-in closet, and a full bath. The walkup attic offers plentiful storage. In the walkout basement, there is the second fireplace, storage, utilities and laundry. A large backyard and convenient location round out the many features of this unique property!

59 Beech St., Winchendon

$415,000

4 Beds ⋅ 1 Baths ⋅ 73592195 MLS

Do not miss out on the opportunity to own this well kept, and recently updated raised ranch style house. Over 1300 SQ FT featuring 4 generously sized bedrooms and 1 full bath. Recent tasteful updates throughout house include kitchen, bathroom, flooring and more! New septic in 2025! Nestled on a beautiful level lot that is over 2 ACRES offering a great space for recreational activities or hosting gatherings!

706 Brown St, Winchendon

$329,900

3 Beds ⋅ 2 Baths ⋅ 73591508 MLS

Welcome to 179 Glenallen Street! This spacious 3-bedroom home offers plenty of room to spread out, including an additional bonus room perfect for a home office, playroom, or hobby space. Thoughtfully maintained over the years, the home is clean, move-in ready, and full of potential for buyers to add their own finishing touches. A brand-new furnace will be installed, offering peace of mind for the next owners. Inside, you'll appreciate the generous living spaces and classic charm, while outside, the scenic half-acre lot provides room to relax, garden, or entertain. A garage adds convenience and extra storage. With solid features, comfortable living spaces, and opportunities to make it your own, this home is ready for its next chapter!

179 Glenallen St, Winchendon

$899,000

3 Beds ⋅ 3 Baths ⋅ 73591486 MLS

Lakefront living with room to enjoy it! Set on Lake Monomonac, 66 Lakeview Drive in Winchendon offers beautiful views, a generous yard, and comfortable spaces for both everyday living and weekends with a houseful of guests, all less than 90 minutes from Boston.Inside, beautiful hardwood floors and a propane stove add warmth to the home, while stunning lake views draw you into the living room and dining area. Whether you're sitting down to dinner or taking a quiet afternoon to yourself, the water is always part of the setting. The deck is a natural extension of these spaces, with room to enjoy morning coffee, share a meal outdoors, or watch the boats go by.Downstairs, a family room provides a second gathering space for watching movies, playing games, or unwinding after a day outside. This level also includes a bedroom, bathroom, and laundry area, plus a bunk room for even more guests that can transform to storage in the winter. It's a practical setup for hosting family and friends, with places to gather and room to spread out when everyone comes to stay. Step directly outside from the lower level to additional patios and decks.The waterfront is the best of both worlds, tucked into a quiet no-wake zone with quick access to the main body of the lake. The spacious yard stretches toward the lake, bringing together a sandy beach, a fire pit, and plenty of room for lawn games and cookouts. Spend the afternoon swimming or relaxing along the shore, then pull up a chair around the fire as evening settles in. A private boat ramp makes launching and retrieving your boat convenient, whether you're heading out to fish, cruise, or explore the lake.As if that wasnt enough, your very own outdoor bar adds a casual gathering spot for summer afternoons, evenings with friends and doubles as extra storage space. The attached garage provides convenient parking and storage for tools and recreational gear.With inviting spaces inside and out, this home offers more than a view of the lake. It gives you the beach, boating access, and room to share the experience, all right at home. Open House Saturday October 24 th from 10am -12pm

66 Lakeview Dr, Winchendon

$199,000

1 Beds ⋅ 1 Baths ⋅ 73590247 MLS

Small Home, Big Opportunity! Welcome to 111 Franklin Street in Winchendon! This charming 1-bedroom, 1-bath detached home offers an opportunity for those seeking simplicity, affordability, and the benefits of having a place to call their own. Featuring convenient single-level living, a vinyl-sided exterior, gravel driveway, and yard surrounded by mature trees, this property offers plenty of possibilities. Whether you’re a first-time homebuyer, looking to downsize, or considering an investment property, this home provides a manageable alternative to traditional housing. Bring your vision and discover the possibilities of making this property your own. An opportunity to own a detached home at an approachable price point. Schedule your showing today!

111 Franklin St, Winchendon

$750,000

4 Beds ⋅ 3 Baths ⋅ 73589552 MLS

Historic character meets country living at “The Corners,” a distinctive Federal-style residence known as the Stearns House, set on 3.03 acres of wooded and open land in Winchendon. With nearly 3,000 sq. ft., 4 bedrooms, 2.5 baths and 5 fireplaces, this property offers generous spaces for everyday living and entertaining.The home features an eat-in kitchen, dining room, spacious living room, office, den and an oversized sunroom with a fireplace. Two covered porches invite you to relax outdoors, while a large mudroom, storage room and attached 5-bay garage add convenience.A 30’ x 34’ post-and-beam barn includes horse stalls, a storage room, animal pen and full loft, complemented by a 12’ x 12’ former icehouse. A small pasture with electric fencing offers space for horses or goats. Enjoy a large fenced dog area and a 32’ x 54’ fenced garden with berry bushes; both fences are removable.The land offers potential to subdivide and create 2 additional ANR lots. Buyer is responsible for verifying feasibility, applying for and obtaining all required Town approvals or endorsements, and completing the Town’s required process. Additional lots are not currently approved.Recent improvements include 37 new double-pane windows (August 2025), additional rear gutters (September 2025), a remodeled main bath with shower, fresh interior paint, refinished wood and painted floors, and new concrete floors in the garage bays. Additional features include an architectural-shingle house roof, metal barn roof, house and barn exterior painting (June 2022), a furnace installed in November 2021, updated 200-amp electrical service, oil heat, town water and sewer, and a stone-wall basement with a concrete floor.Convenient access to Routes 12, 140 and 2, with commuter rail available in Fitchburg. Historic charm, versatile outbuildings and room to cultivate your own country lifestyle!

202 Ash St, Winchendon

$435,000

3 Beds ⋅ 2 Baths ⋅ 73588567 MLS

Known as “La Casa Azul,” this lovingly maintained ranch-style home welcomes you with an open-concept design that is perfect for family gatherings. The kitchen is a baker’s dream, featuring an oversized island which overlooks the dining and living room, granite countertops, and stainless-steel appliances. The primary bedroom offers its own private retreat, complete with a walk-in closet, a generously sized bathroom with a soaking tub and a separate stand-up shower, and also its own door that leads onto the back deck, to enjoy a quiet evening before retreating to bed. Two additional bedrooms, a full bathroom, and a convenient laundry area complete the first floor. The daylight basement offers an office, work area, and a large partially finished room ready for the new owners to make their own while building sweat equity. Outside, the property features a two-car garage, storage shed, and an expansive back deck that provides plenty of space for entertaining. The yard is beautifully adorned with established perennials, adding charm and color throughout the seasons.

260 Ash St., Winchendon

$579,999

3 Beds ⋅ 3 Baths ⋅ 73588068 MLS

Beautiful, like-new, 4-year-old traditional Asher Colonial offering 1,828 sq. ft. on 4.13 private acres. This home boasts an upgraded brick walkway and large granite entry steps. The open-concept floor plan features a spacious kitchen with upgraded cabinets to the ceiling with crown molding, granite countertops, a granite island, and stainless steel appliances. The formal dining room is stunning! A front-to-back living room and half bath with laundry complete the first floor.A slider off the kitchen leads to a private deck overlooking the new above-ground pool and magnificent scenic views. The huge front-to-back primary suite features a walk-in closet, linen closet, and private full bath. Two generously sized bedrooms and a full bath complete the second floor. There is a large walk-out basement with French doors and high ceilings, perfect for a future finished space. Additional features include a 2-car attached garage, central air, Generac generator, and pool with equipment. Make this gorgeous Country Colonial, just minutes from downtown, shopping, and restaurants, your home today!

90 Royalston Rd N, Winchendon

$599,900

4 Beds ⋅ 4 Baths ⋅ 73587925 MLS

Looking to be away from it all, yet still convenient enough for commuting--just 4 miles from NH and 11 low-traffic miles to Route 2? This historical former country club sits on 18.6 wooded acres across two parcels. The interior offers approximately 3,400 square feet of living space with 4 bedrooms and 4 bathrooms. The great hall measures 48 feet by 25 feet and has beamed ceilings, wood paneled walls, hardwood floors, and a center brick fireplace with a wood stove, and the dining area shares the same room. Dining room furniture original to the home is included as a gift to buyers. The kitchen opens to the deck through French doors, with a center island, granite counters, a Sub-Zero refrigerator and freezer, two full size Miele ovens, and an espresso station. A butler’s pantry connects to the kitchen and to the great hall through a swinging door, and it keeps its original glass front cabinets alongside granite counters, a sink, and a dishwasher. The second floor primary suite has wood paneled ceilings, a skylight, and a bathroom. The first floor residential wing has two additional bedrooms, each with a dedicated bathroom. A fourth bedroom would make a great library and has exclusive use of a large three season porch. The washer, dryer, dishwasher, and hybrid electric water heater date from 2023 to 2026. Heat is oil fired hot water baseboard with Nest thermostats, along with 200 amp electric service and a 30 amp outlet for recreational vehicles. Some air sealing and weatherization was completed in 2023. The home is served by town water and town sewer. It’s set at the end of a dead-end street, with access through stone columns that align with the craftsman bungalow style of the home and the impressive front entrance has a covered front porch with a full width stone base. There’s also a back deck and a storage shed. The sellers have catalogued more than 70 species of birds on the property, along with fireflies and other wildlife. The driveway parks 12 or more vehicles. Buyers may want to explore allowed uses other than residential. Winchendon offers a vibrant main street, golf, tennis, a new outdoor amphitheater, trails, a 9+ mile paved bike path, and public and private schools. This wonderful and unique property is being listed as-is, with many projects completed, however the sellers are not able to make further repairs.

25 Fairbank Street, Winchendon

$290,000

2 Beds ⋅ 1 Baths ⋅ 73586262 MLS

This is a well-kept neat and clean cottage with expected irregularities. Many recent updates. The house has five rooms and one full bath, all on the first-floor level. It has three heating options, electric, Propane gas, or a pellet stove which is included in the price. The Propane gas heaters are new. The house only has a partial cellar with access through a floor hatch. The house is serviced by a recently installed septic system. The roof shingles are about 7 years old. The property is located at the end of a low traffic st. Great location. The lot is mostly cleared with lawn in the front and back.

123 Franklin St, Winchendon

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Winchendon Homes for Sale

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