1,525 properties for sale in Winchendon

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

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!

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 ran

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!

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 1/2 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

Completely refinished in 2023, this beautiful 4-bedroom, 2.5-bath home combines modern updates with a functional layout in a fantastic location. Just minutes from downtown shopping, restaurants, schools, and commuter routes, you'll enjoy the convenience of being close to everything while still having a backyard that feels surprisingly private. Step inside to an open-concept first floor where the living room, dining area, and kitchen flow together, making the space perfect for everyday living and entertaining. The living room features a coffered ceiling and a large picture window that fills the home with natural light. The kitchen offers plenty of cabinet space, granite countertops, a beautiful tile backsplash, and a center island overlooking the dining area, making it easy to stay connected with family and guests while preparing meals. The first-floor primary suite is a standout feature, offering a spacious bedroom, walk-in closet, and a beautifully finished private bath complete with

CLASSIC NEW ENGLAND VILLAGE COLONIAL - NEW TO THE MARKET and 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

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 ran

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

This beautifully updated single-family home offers the perfect blend of classic character and modern comfort in this established Winchendon neighborhood. Featuring 4 bedrooms and 1 full bathroom, this home has been thoughtfully refreshed and is ready for its next owners to move right in. The main level offers a welcoming layout with comfortable living spaces, an open kitchen, and convenient access to the rest of the home. Upstairs, you'll find well-appointed bedrooms with space for family, guests, or a home office. Outside, the approximately quarter-acre lot provides a manageable yard with room to enjoy the outdoors, garden, entertain, or simply relax. Located on a quiet, tree-lined street while remaining conveniently close to local schools, shopping, restaurants, recreation, and downtown Winchendon, this property offers an excellent opportunity for a first-time buyer, growing household, or anyone looking for a move-in-ready home. Seller offering a complimentary 1-year home warranty fo

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 1/2 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

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 a

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

CLASSIC NEW ENGLAND VILLAGE COLONIAL - NEW TO THE MARKET and 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

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

This beautifully maintained 5 bedroom, 2 1/2 bath colonial boasts over 3400 sq ft. of living space. Built in 2016, this single-family residence offers spacious comfort and expansive outdoor living. The large open concept fist floor includes a modern kitchen with stainless steel appliances, granite countertops, a dual oven and center island with cooktop. A slider off the kitchen leads to a private deck with a patio fire pit and above ground pool just steps away.The property sits on a generous 5.49 acre lot, offering significant private outdoor space for recreation or quiet enjoyment. A two-car garage provides practical storage and parking solutions. This property offers a connection to nature, while only a 4 minute drive to Winchendon center with amenities such as restaurants and shopping

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

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

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 and private full bathroom. Convenient 2nd-floor laundry completes the upper level. The

This beautifully maintained 5 bedroom, 2 1/2 bath colonial boasts over 3400 sq ft. of living space. Built in 2016, this single-family residence offers spacious comfort and expansive outdoor living. The large open concept fist floor includes a modern kitchen with stainless steel appliances, granite countertops, a dual oven and center island with cooktop. A slider off the kitchen leads to a private deck with a patio fire pit and above ground pool just steps away.The property sits on a generous 5.49 acre lot, offering significant private outdoor space for recreation or quiet enjoyment. A two-car garage provides practical storage and parking solutions. This property offers a connection to nature, while only a 4 minute drive to Winchendon center with amenities such as restaurants and shopping

Investors and 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

The money is in the details! Over $200K in recent upgrades at 101 Royalston Rd N, Winchendon! Beautifully updated 3-bedroom, 1.5-bath home showcasing quality craftsmanship throughout. Remodeled kitchen features a massive center island with seating, oversized sink, tile backsplash, tile flooring, double wall ovens, cooktop with range hood, wine refrigerator, pantry closets, and stainless-steel appliances. Front-to-back living room offers Teak flooring and leads to the composite deck overlooking the private backyard. Heated saltwater in-ground pool with cabana pool house, snow-load-rated gazebo (no seasonal removal needed), mini gazebo over the gas grills, and commercial grade fenced in yard. Spacious primary bedroom with walk-in closet and Brazilian Chestnut hardwood flooring extending into the hallway and additional bedrooms. Custom built-ins create a stellar dressing room or teen dream bedroom. Bath features a tiled walk-in shower and stone-top vanity. Finished lower level with distin

This beautifully updated single-family home offers the perfect blend of classic character and modern comfort in this established Winchendon neighborhood. Featuring 4 bedrooms and 1 full bathroom, this home has been thoughtfully refreshed and is ready for its next owners to move right in. The main level offers a welcoming layout with comfortable living spaces, an open kitchen, and convenient access to the rest of the home. Upstairs, you'll find well-appointed bedrooms with space for family, guests, or a home office. Outside, the approximately quarter-acre lot provides a manageable yard with room to enjoy the outdoors, garden, entertain, or simply relax. Located on a quiet, tree-lined street while remaining conveniently close to local schools, shopping, restaurants, recreation, and downtown Winchendon, this property offers an excellent opportunity for a first-time buyer, growing household, or anyone looking for a move-in-ready home. Seller offering a complimentary 1-year home warranty fo

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

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

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

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

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

This large 4unit house located at center of the town, always fully rented, total monthly income; $6590, each tenant pay their own utilities. each unit has good size room. the house will deliver with all the tenants because seller don't want to lose the rental income. only do showing on weekend. 4 years new roof. rare to find, great property created good cash flow, it won't last long

Experience tranquil waterfront living at its finest in this 3-bedroom, 2-bathroom lakefront retreat on picturesque Lake Monomonac. Nestled on a level lot with mature landscaping, this property offers a private sandy beach and stunning water views in a peaceful cove setting. Tucked away on a quiet dead-end road, you'll enjoy the perfect balance of privacy and convenience, with easy access to Route 202, shopping, dining, and the many recreational amenities the area has to offer. Whether you're seeking a year-round residence or a relaxing waterfront getaway, this exceptional property delivers the ultimate lakeside lifestyle!