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$649,900

Welcome home to 38 Windsor Street! This beautifully rebuilt two-story Colonial offers the look, feel, and quality of new construction, blending clean contemporary finishes with timeless curb appeal. Completely renovated from top to bottom, this turn-key home is ready for its first new owner. Featuring 5 bedrooms, 4 full bathrooms, and approximately 2,200 square feet of thoughtfully designed living space, every detail has been updated, including a new roof, siding, hardwood flooring throughout, a stunning new kitchen with new appliances and countertops, beautifully remodeled bathrooms, and much more. The bright, open main level flows seamlessly from the living area into the spacious central kitchen, creating the perfect space for everyday living and entertaining. The first-floor primary suite offers privacy with a luxurious en-suite bath featuring double vanities and a tiled walk-in shower. A partially finished lower level provides flexible space for a family room, guest bedroom, home office, or recreation area, along with a dedicated laundry area. Upstairs offers three additional bedrooms and two full bathrooms. Outside, enjoy a low-maintenance yard, detached one-car garage, and additional off-street driveway parking. Conveniently located in a desirable Cumberland neighborhood, this move-in-ready home offers modern style, quality craftsmanship, and exceptional value.

5 Beds ⋅ 4 Baths

Welcome home to 38 Windsor Street! This beautifully rebuilt two-story Colonial offers the look, feel, and quality of new construction, blending clean contemporary finishes with timeless curb appeal. Completely renovated from top to bottom, this turn-key home is ready for its first new owner. Featuring 5 bedrooms, 4 full bathrooms, and approximately 2,200 square feet of thoughtfully designed living space, every detail has been updated, including a new roof, siding, hardwood flooring throughout, a stunning new kitchen with new appliances and countertops, beautifully remodeled bathrooms, and much more. The bright, open main level flows seamlessly from the living area into the spacious central kitchen, creating the perfect space for everyday living and entertaining. The first-floor primary suite offers privacy with a luxurious en-suite bath featuring double vanities and a tiled walk-in shower. A partially finished lower level provides flexible space for a family room, guest bedroom, home office, or recreation area, along with a dedicated laundry area. Upstairs offers three additional bedrooms and two full bathrooms. Outside, enjoy a low-maintenance yard, detached one-car garage, and additional off-street driveway parking. Conveniently located in a desirable Cumberland neighborhood, this move-in-ready home offers modern style, quality craftsmanship, and exceptional value.

38 Winsor Street, Cumberland

Listing courtesy of Chatterton R/E Alliance. Contact:

$964,900

Architectural details and thoughtfully designed living spaces define this impressive Contemporary Colonial in Cumberland's desirable Great Woods neighborhood. From the moment you step inside, soaring ceilings, rich hardwood floors, and an open, light-filled layout create an immediate sense of space. The heart of the home is the two-story great room, where a granite gas fireplace serves as the focal point and opens to the kitchen, complete with upscale appliances, counter seating, and a casual dining nook. Formal living and dining rooms provide additional gathering spaces, with sliding barn doors, plantation shutters, and detailed millwork adding warmth & character. Central AC and a three-car garage further enhance the home's comfort and functionality. Privately tucked away on the main level, the primary suite offers a relaxing escape featuring a soaking tub, tiled shower, and double vanity, while the nearby dedicated home office accommodates today's flexible lifestyle. Upstairs, a striking catwalk and balcony overlook the great room below, connecting two wings, each offering two bedrooms and a full bath, including a junior suite that provides added comfort for guests or extended family. Set on 1.18 acres, the outdoor spaces are equally inviting, with a spacious deck, stone patio, fire pit, and beautiful grounds, extending your living space well beyond the home's walls. With distinctive architecture and a peaceful setting, this home simply stands apart.

5 Beds ⋅ 4 Baths

Architectural details and thoughtfully designed living spaces define this impressive Contemporary Colonial in Cumberland's desirable Great Woods neighborhood. From the moment you step inside, soaring ceilings, rich hardwood floors, and an open, light-filled layout create an immediate sense of space. The heart of the home is the two-story great room, where a granite gas fireplace serves as the focal point and opens to the kitchen, complete with upscale appliances, counter seating, and a casual dining nook. Formal living and dining rooms provide additional gathering spaces, with sliding barn doors, plantation shutters, and detailed millwork adding warmth & character. Central AC and a three-car garage further enhance the home's comfort and functionality. Privately tucked away on the main level, the primary suite offers a relaxing escape featuring a soaking tub, tiled shower, and double vanity, while the nearby dedicated home office accommodates today's flexible lifestyle. Upstairs, a striking catwalk and balcony overlook the great room below, connecting two wings, each offering two bedrooms and a full bath, including a junior suite that provides added comfort for guests or extended family. Set on 1.18 acres, the outdoor spaces are equally inviting, with a spacious deck, stone patio, fire pit, and beautiful grounds, extending your living space well beyond the home's walls. With distinctive architecture and a peaceful setting, this home simply stands apart.

31 Bourque Road, Cumberland

Listing courtesy of Williams & Stuart Real Estate. Contact:

$725,000

Fantastic opportunity to own a well-maintained two-family home in Cumberland! This versatile property features a 1-bedroom, 1-bathroom first-floor unit and a spacious second unit offering 4 bedrooms, providing an ideal setup for owner-occupants, multi-generational living, or investors seeking strong rental potential. Both units offer comfortable layouts with abundant natural light, while off-street parking adds everyday convenience for residents and guests. Situated along Mendon Road, this property enjoys a prime location close to local restaurants, grocery stores, retail centers, and neighborhood businesses. Minutes to the shopping, dining, and entertainment destinations along the Diamond Hill Road and Mendon Road commercial corridors. Enjoy nearby Diamond Hill Park and Monastery Park for walking trails and year-round outdoor recreation. Convenient access to Route 146, Interstate 295, and Interstate 95 provides an easy commute to Providence, Worcester, and surrounding communities. Close to schools, healthcare, golf courses, and just minutes from the Massachusetts border.

5 Beds ⋅ 3 Baths

Fantastic opportunity to own a well-maintained two-family home in Cumberland! This versatile property features a 1-bedroom, 1-bathroom first-floor unit and a spacious second unit offering 4 bedrooms, providing an ideal setup for owner-occupants, multi-generational living, or investors seeking strong rental potential. Both units offer comfortable layouts with abundant natural light, while off-street parking adds everyday convenience for residents and guests. Situated along Mendon Road, this property enjoys a prime location close to local restaurants, grocery stores, retail centers, and neighborhood businesses. Minutes to the shopping, dining, and entertainment destinations along the Diamond Hill Road and Mendon Road commercial corridors. Enjoy nearby Diamond Hill Park and Monastery Park for walking trails and year-round outdoor recreation. Convenient access to Route 146, Interstate 295, and Interstate 95 provides an easy commute to Providence, Worcester, and surrounding communities. Close to schools, healthcare, golf courses, and just minutes from the Massachusetts border.

1251 Mendon Road, Cumberland

Listing courtesy of Century 21 Limitless. Contact:

$1,260,000

Experience perfect blend of timeless farmhouse charm & modern comfort in this exceptional custom-built home nestled on nearly two private acres in desirable North Cumberland. Enjoy peaceful surroundings from the welcoming wraparound farmer's porch, two spacious decks, sunroom, beautiful in-ground pool perfect for entertaining. Inside, the thoughtfully designed floor plan features a spacious eat-in kitchen with a walk-in pantry, peninsula, breakfast area, and an open layout overlooking the cozy family den with one of three gas fireplaces. The main level also offers a formal dining room, living room with French doors ideal for a home office, full bath, laundry room, mudroom Upstairs, the cathedral-ceiling primary suite boasts a private balcony, gas fireplace, oversized walk-in closet, and luxurious spa-inspired bath. Additional bedrooms, full bath with double vanity and impressive 27' x 24' vaulted great room designed for entertaining complete the second floor. The finished walkout lower level offers even more living space with a fireplaced family room, wet bar/kitchenette, full bath, and flexible bonus rooms perfect for a home office, guest suite, gym, or hobby space, all with direct access to the sunroom and pool area. A detached two-story barn provides endless possibilities for a workshop or studio. Bonus -solar panels help offset electricity costs, providing increased energy efficiency and long-term savings while reducing monthly utility expenses. Must see to appreciate!

5 Beds ⋅ 4 Baths

Experience perfect blend of timeless farmhouse charm & modern comfort in this exceptional custom-built home nestled on nearly two private acres in desirable North Cumberland. Enjoy peaceful surroundings from the welcoming wraparound farmer's porch, two spacious decks, sunroom, beautiful in-ground pool perfect for entertaining. Inside, the thoughtfully designed floor plan features a spacious eat-in kitchen with a walk-in pantry, peninsula, breakfast area, and an open layout overlooking the cozy family den with one of three gas fireplaces. The main level also offers a formal dining room, living room with French doors ideal for a home office, full bath, laundry room, mudroom Upstairs, the cathedral-ceiling primary suite boasts a private balcony, gas fireplace, oversized walk-in closet, and luxurious spa-inspired bath. Additional bedrooms, full bath with double vanity and impressive 27' x 24' vaulted great room designed for entertaining complete the second floor. The finished walkout lower level offers even more living space with a fireplaced family room, wet bar/kitchenette, full bath, and flexible bonus rooms perfect for a home office, guest suite, gym, or hobby space, all with direct access to the sunroom and pool area. A detached two-story barn provides endless possibilities for a workshop or studio. Bonus -solar panels help offset electricity costs, providing increased energy efficiency and long-term savings while reducing monthly utility expenses. Must see to appreciate!

45 Pine Swamp Road, Cumberland

Listing courtesy of RE/MAX Properties. Contact: christinecorriveau@hotmail.com

$1,599,000

Exceptional value for this legal 2-unit compound on 7.84 private, gated acres in Cumberland. Comprising 3 parcels, this estate features two distinct residences with separate utilities and mailing addresses ideal for multi-generational living, owner-occupants, or premium rental income. The primary 4BR, 5BA Colonial offers 2,900+ SF of sun-filled space plus a 1,300 SF finished walkout lower level. Pride of ownership is evident throughout; recent updates include new roofs on all structures, a modern granite kitchen, new flooring, fresh paint, new Harvey Elite triple-pane windows and skylights and much more. The open layout flows beautifully, leading to a second level with a primary suite, 3 additional bedrooms with hardwoods, a den, and a generous full bath. The second legal residence is an immaculate 1,260 SF permitted apartment above the barn, offering total autonomy and privacy for tenants or guests. Property infrastructure is unmatched, featuring a separate 1,200 SF heated garage, workshop, shed, and chicken coop. The grounds are a private oasis boasting a dreamy open pasture, natural freshwater spring-fed pond, irrigation, invisible fencing, and a custom patio with a fire pit. This rare, versatile offering perfectly combines classic New England charm with modern income potential. Spectacular location is a short drive to either Boston or Providence. Close to everything with secluded privacy-must see! View the video tour to experience the scale of this unique estate.

5 Beds ⋅ 7 Baths

Exceptional value for this legal 2-unit compound on 7.84 private, gated acres in Cumberland. Comprising 3 parcels, this estate features two distinct residences with separate utilities and mailing addresses ideal for multi-generational living, owner-occupants, or premium rental income. The primary 4BR, 5BA Colonial offers 2,900+ SF of sun-filled space plus a 1,300 SF finished walkout lower level. Pride of ownership is evident throughout; recent updates include new roofs on all structures, a modern granite kitchen, new flooring, fresh paint, new Harvey Elite triple-pane windows and skylights and much more. The open layout flows beautifully, leading to a second level with a primary suite, 3 additional bedrooms with hardwoods, a den, and a generous full bath. The second legal residence is an immaculate 1,260 SF permitted apartment above the barn, offering total autonomy and privacy for tenants or guests. Property infrastructure is unmatched, featuring a separate 1,200 SF heated garage, workshop, shed, and chicken coop. The grounds are a private oasis boasting a dreamy open pasture, natural freshwater spring-fed pond, irrigation, invisible fencing, and a custom patio with a fire pit. This rare, versatile offering perfectly combines classic New England charm with modern income potential. Spectacular location is a short drive to either Boston or Providence. Close to everything with secluded privacy-must see! View the video tour to experience the scale of this unique estate.

365 West Wrentham Road 367, Cumberland

Listing courtesy of Lila Delman Compass. Contact: 401-835-1616

$569,900

Rare investment opportunity in highly desirable Cumberland! This versatile multi-family property is currently configured as a spacious two-family home. Featuring 5 generously sized bedrooms, 3 full bathrooms, granite countertops, beautiful hardwood floors, expansive basement storage, and a stunning three-season room, this property blends charm, functionality, and opportunity. Multiple driveways provide ample parking, while the large room sizes create comfortable living spaces for both owners and tenants. Active Lead Certs in hand! Nestled on a peaceful dead-end street, this home offers the perfect balance of quiet residential living with unbeatable convenience just a short walk to local restaurants, breweries, and scenic bike paths. Located in one of the nation's most sought-after communities, Cumberland was recognized as one of the best places to live in 2025, making this property an even smarter investment. With only minor cosmetic updates needed to unlock its full potential, this property is competitively priced and presents an exceptional opportunity for investors or owner-occupants looking to maximize value. Whether you're seeking strong rental income, multi-generational living, or a smart long-term investment, this is the kind of property that rarely hits the market.

5 Beds ⋅ 3 Baths

Rare investment opportunity in highly desirable Cumberland! This versatile multi-family property is currently configured as a spacious two-family home. Featuring 5 generously sized bedrooms, 3 full bathrooms, granite countertops, beautiful hardwood floors, expansive basement storage, and a stunning three-season room, this property blends charm, functionality, and opportunity. Multiple driveways provide ample parking, while the large room sizes create comfortable living spaces for both owners and tenants. Active Lead Certs in hand! Nestled on a peaceful dead-end street, this home offers the perfect balance of quiet residential living with unbeatable convenience just a short walk to local restaurants, breweries, and scenic bike paths. Located in one of the nation's most sought-after communities, Cumberland was recognized as one of the best places to live in 2025, making this property an even smarter investment. With only minor cosmetic updates needed to unlock its full potential, this property is competitively priced and presents an exceptional opportunity for investors or owner-occupants looking to maximize value. Whether you're seeking strong rental income, multi-generational living, or a smart long-term investment, this is the kind of property that rarely hits the market.

17 Victory Street, Cumberland

Listing courtesy of Strive Realty. Contact:

$995,000

Welcome to 12 Howard Road a twelve-acre bucolic retreat minutes from everything, yet feeling worlds away. Set along the serene shores of Howard Pond and the Abbott Run across four parcels sold together, this extraordinary Cumberland estate was lovingly cultivated by a Master Gardener of Rhode Island. Giant oaks and pines span the property on all sides, wild native plants emerge in glorious succession along the shoreline each spring and summer, and spectacular sunsets reflect across the water each evening. Magnificent blooming Dogwood trees, Japanese maples, and established gardens complete a setting of breathtaking, ever-changing beauty. The classic Colonial delivers five bedrooms and three-and-a-half baths with hardwood floors throughout, stone countertops throughout, and all bathrooms retiled within the last five years. A wood-paneled living room with exposed beams flows into an unexpectedly oversized eat-in kitchen, while a distinguished cherry office with built-in bookshelves and cherry floors adds a rare finishing touch. The fully self-contained in-law suite features a private entrance, full kitchen, bedroom, full bath, and a three-season porch with panoramic pond and backyard views. Outside, large bluestone patios, ample off-street parking across two driveways, and a four-car garage round out this truly rare Cumberland offering.

5 Beds ⋅ 4 Baths

Welcome to 12 Howard Road a twelve-acre bucolic retreat minutes from everything, yet feeling worlds away. Set along the serene shores of Howard Pond and the Abbott Run across four parcels sold together, this extraordinary Cumberland estate was lovingly cultivated by a Master Gardener of Rhode Island. Giant oaks and pines span the property on all sides, wild native plants emerge in glorious succession along the shoreline each spring and summer, and spectacular sunsets reflect across the water each evening. Magnificent blooming Dogwood trees, Japanese maples, and established gardens complete a setting of breathtaking, ever-changing beauty. The classic Colonial delivers five bedrooms and three-and-a-half baths with hardwood floors throughout, stone countertops throughout, and all bathrooms retiled within the last five years. A wood-paneled living room with exposed beams flows into an unexpectedly oversized eat-in kitchen, while a distinguished cherry office with built-in bookshelves and cherry floors adds a rare finishing touch. The fully self-contained in-law suite features a private entrance, full kitchen, bedroom, full bath, and a three-season porch with panoramic pond and backyard views. Outside, large bluestone patios, ample off-street parking across two driveways, and a four-car garage round out this truly rare Cumberland offering.

12 Howard Road, Cumberland

Listing courtesy of Mott & Chace Sotheby's Intl.. Contact:

$549,900

Spacious and well-maintained 2-family property offering excellent owner-occupant or investment potential! The first-floor unit features 3 generous bedrooms, while the second-floor unit offers 2 bedrooms with comfortable living space. A large walk-up third floor provides tremendous opportunity for expansion convert it into an additional unit, combine it with the second floor to dramatically increase living space and rental income potential, or simply utilize it for storage. This property also features separate utilities, a low-maintenance exterior with vinyl siding and replacement windows, a 2-car garage, fenced yard, and plenty of off-street parking. A versatile multi-family property with endless possibilities!

5 Beds ⋅ 2 Baths

Spacious and well-maintained 2-family property offering excellent owner-occupant or investment potential! The first-floor unit features 3 generous bedrooms, while the second-floor unit offers 2 bedrooms with comfortable living space. A large walk-up third floor provides tremendous opportunity for expansion convert it into an additional unit, combine it with the second floor to dramatically increase living space and rental income potential, or simply utilize it for storage. This property also features separate utilities, a low-maintenance exterior with vinyl siding and replacement windows, a 2-car garage, fenced yard, and plenty of off-street parking. A versatile multi-family property with endless possibilities!

19 Elm Street, Cumberland

Listing courtesy of The Mello Group, Inc.. Contact: