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$730,000

Nestled on over 4.5 acres, this charming Cape home offers a serene retreat surrounded by nature. The property is adorned with lush fruit trees, enhancing its picturesque landscape. A circular driveway welcomes you, leading to a spacious three-car garage and an inviting outdoor fire pit, perfect for cozy gatherings under the stars. Inside, the home’s thoughtful layout begins with a convenient first-floor bedroom, ideal for guests or family. The beautifully appointed kitchen stands out with ample storage, making it both functional and stylish for culinary enthusiasts. Adjacent to the kitchen, the living and dining area exudes a relaxed atmosphere, highlighted by a stunning rock fireplace equipped with a pellet stove, creating warmth and ambiance during colder months. This space flows seamlessly into a gorgeous three-season porch, where you can enjoy the beauty of the outdoors year-round, also featuring a pellet stove for additional comfort. Venturing to the second floor, you’ll find two spacious bedrooms that share a well-designed Jack and Jill bathroom, complete with a luxurious soaking tub—perfect for unwinding after a long day. The basement is a versatile space, serving as an ideal media area for movie nights or family gatherings. Additionally, a second room features striking barn doors, adding a rustic touch and ensuring privacy when needed. This home beautifully blends comfort with charm, making it a perfect sanctuary for both relaxation and entertaining.

3 Beds ⋅ 2 Baths ⋅ 5104529 MLS

Nestled on over 4.5 acres, this charming Cape home offers a serene retreat surrounded by nature. The property is adorned with lush fruit trees, enhancing its picturesque landscape. A circular driveway welcomes you, leading to a spacious three-car garage and an inviting outdoor fire pit, perfect for cozy gatherings under the stars. Inside, the home’s thoughtful layout begins with a convenient first-floor bedroom, ideal for guests or family. The beautifully appointed kitchen stands out with ample storage, making it both functional and stylish for culinary enthusiasts. Adjacent to the kitchen, the living and dining area exudes a relaxed atmosphere, highlighted by a stunning rock fireplace equipped with a pellet stove, creating warmth and ambiance during colder months. This space flows seamlessly into a gorgeous three-season porch, where you can enjoy the beauty of the outdoors year-round, also featuring a pellet stove for additional comfort. Venturing to the second floor, you’ll find two spacious bedrooms that share a well-designed Jack and Jill bathroom, complete with a luxurious soaking tub—perfect for unwinding after a long day. The basement is a versatile space, serving as an ideal media area for movie nights or family gatherings. Additionally, a second room features striking barn doors, adding a rustic touch and ensuring privacy when needed. This home beautifully blends comfort with charm, making it a perfect sanctuary for both relaxation and entertaining.

54b Oak Hill Rd, Brookline

$314,900

A HISTORIC BROOKLINE NEW ENGLANDER TO MAKE YOUR OWN! Welcome to this charming New England home where timeless character meets everyday comfort. Built in 1894, this 3-bedroom, 1.5-bath home offers approximately 1,487 square feet of inviting living space on a beautifully sized 0.40-acre lot in the heart of picturesque Brookline. Step inside to discover the warmth and personality only a historic home can offer, with comfortable living spaces ready for your personal touch and care. There's so much opportunity here. The flexible floor plan provides room for gathering, working from home, or simply relaxing, while the spacious bedrooms offer comfortable accommodations for family and guests alike. Outside, the level yard provides plenty of space for gardening, entertaining, pets, or outdoor recreation. An attached breezeway and garage adds convenience and additional storage, while the home's classic New England architecture creates timeless curb appeal. Ideally located just minutes from the MA border, this property offers the perfect balance of small-town charm and commuter convenience, with easy access to Nashua, Milford, and surrounding communities. Enjoy nearby conservation land, local farms, walking trails, and the highly regarded Hollis-Brookline school district, all while experiencing the peaceful lifestyle Brookline is known for. Investment opportunities don't come like this every day, especially in Brookline. Whether you're searching for your first home, looking to downsize, or seeking a property filled with character and potential, this classic New England gem is ready to be brought to life with your personal touch. Bring your vision and make this historic Brookline home your own.

3 Beds ⋅ 2 Baths ⋅ 5099507 MLS

A HISTORIC BROOKLINE NEW ENGLANDER TO MAKE YOUR OWN! Welcome to this charming New England home where timeless character meets everyday comfort. Built in 1894, this 3-bedroom, 1.5-bath home offers approximately 1,487 square feet of inviting living space on a beautifully sized 0.40-acre lot in the heart of picturesque Brookline. Step inside to discover the warmth and personality only a historic home can offer, with comfortable living spaces ready for your personal touch and care. There's so much opportunity here. The flexible floor plan provides room for gathering, working from home, or simply relaxing, while the spacious bedrooms offer comfortable accommodations for family and guests alike. Outside, the level yard provides plenty of space for gardening, entertaining, pets, or outdoor recreation. An attached breezeway and garage adds convenience and additional storage, while the home's classic New England architecture creates timeless curb appeal. Ideally located just minutes from the MA border, this property offers the perfect balance of small-town charm and commuter convenience, with easy access to Nashua, Milford, and surrounding communities. Enjoy nearby conservation land, local farms, walking trails, and the highly regarded Hollis-Brookline school district, all while experiencing the peaceful lifestyle Brookline is known for. Investment opportunities don't come like this every day, especially in Brookline. Whether you're searching for your first home, looking to downsize, or seeking a property filled with character and potential, this classic New England gem is ready to be brought to life with your personal touch. Bring your vision and make this historic Brookline home your own.

42 S Main St, Brookline

$980,000

Privately set on 2.38 acres in one of Brookline's most desirable neighborhoods, this beautifully maintained Craftsman-influenced home offers 5,223 square feet of thoughtfully designed living space, blending comfort, versatility, and everyday elegance. With primary suites on each level, the layout is ideal for multi-generational living, an in-home business, or accommodating long term guests. The heart of the home is a standout feature: a striking wood-burning fireplace with a cast-iron cooktop and dual pizza ovens, recently rebuilt and relined to preserve its character and ensure years of reliable performance. Cathedral ceilings, hardwood floors, and a granite appointed kitchen with double ovens create a warm, inviting atmosphere that's equally suited for everyday living and entertaining. A finished walkout lower level provides additional flexible living space with direct access to the outdoors. The home has been thoughtfully updated with a newer heating system, central air conditioning, and an updated leach field. Generator-ready electrical service and two wood-burning fireplaces add both practicality and charm. Outside, the property transforms into a private retreat. A heated Gunite in-ground pool with a waterfall serves as the centerpiece of the backyard, complemented by a granite patio and mature landscaping. The grounds feature Macintosh and Cortland apple trees, blueberry bushes, and quince bushes, offering seasonal beauty and the enjoyment of homegrown fruit. These established plantings complement the existing flowering shrubs and lend the property a subtle New England orchard feel. Located just minutes from Lake Potanipo, the Brookline Rail Trail, and the Andres Institute of Art, the home offers a peaceful balance of privacy and convenience, with access to the highly regarded Hollis-Brookline schools and nearby commuting routes. A welcoming, thoughtfully appointed home offering exceptional flexibility, quality updates, and a truly special outdoor setting.

4 Beds ⋅ 5 Baths ⋅ 5087216 MLS

Privately set on 2.38 acres in one of Brookline's most desirable neighborhoods, this beautifully maintained Craftsman-influenced home offers 5,223 square feet of thoughtfully designed living space, blending comfort, versatility, and everyday elegance. With primary suites on each level, the layout is ideal for multi-generational living, an in-home business, or accommodating long term guests. The heart of the home is a standout feature: a striking wood-burning fireplace with a cast-iron cooktop and dual pizza ovens, recently rebuilt and relined to preserve its character and ensure years of reliable performance. Cathedral ceilings, hardwood floors, and a granite appointed kitchen with double ovens create a warm, inviting atmosphere that's equally suited for everyday living and entertaining. A finished walkout lower level provides additional flexible living space with direct access to the outdoors. The home has been thoughtfully updated with a newer heating system, central air conditioning, and an updated leach field. Generator-ready electrical service and two wood-burning fireplaces add both practicality and charm. Outside, the property transforms into a private retreat. A heated Gunite in-ground pool with a waterfall serves as the centerpiece of the backyard, complemented by a granite patio and mature landscaping. The grounds feature Macintosh and Cortland apple trees, blueberry bushes, and quince bushes, offering seasonal beauty and the enjoyment of homegrown fruit. These established plantings complement the existing flowering shrubs and lend the property a subtle New England orchard feel. Located just minutes from Lake Potanipo, the Brookline Rail Trail, and the Andres Institute of Art, the home offers a peaceful balance of privacy and convenience, with access to the highly regarded Hollis-Brookline schools and nearby commuting routes. A welcoming, thoughtfully appointed home offering exceptional flexibility, quality updates, and a truly special outdoor setting.

107 Fresh Pond Ln, Brookline

$1,075,000

PRICE IMPROVEMENT 8/4/26! A rare multigenerational opportunity in Brookline, this thoughtfully rebuilt property offers exceptional space, flexibility, and income-producing potential. The main residence features three bedrooms, a finished attic, a private guest suite with a kitchenette and bathroom, and a spacious chef’s kitchen with abundant counter space, storage, and a beautiful copper sink. The legal two-bedroom ADU includes its own kitchen, living room, and bathroom, making it ideal for extended family, guests, or potential rental income to help offset monthly mortgage expenses. With its unique layout and numerous private living spaces, the property may also offer exciting potential for a bed-and-breakfast or similar hospitality use, subject to applicable town approvals and permitting. Additional highlights include two separate parking areas, a large deck and patio with a firepit, and a two-story barn offering space for storage, hobbies, a workshop, or a potential office. Loved by the same family for years, this home is filled with natural light, inviting gathering spaces, and room to grow. Located in desirable Brookline, the property offers the charm of a small New Hampshire town with convenient access to local amenities, conservation land, and Brookline’s extensive network of trails. SELLERS ARE OFFERING A $25,000 CLOSING CREDIT toward painting, carpeting, an interest-rate buy-down, or other allowable buyer closing costs!

5084928 MLS

PRICE IMPROVEMENT 8/4/26! A rare multigenerational opportunity in Brookline, this thoughtfully rebuilt property offers exceptional space, flexibility, and income-producing potential. The main residence features three bedrooms, a finished attic, a private guest suite with a kitchenette and bathroom, and a spacious chef’s kitchen with abundant counter space, storage, and a beautiful copper sink. The legal two-bedroom ADU includes its own kitchen, living room, and bathroom, making it ideal for extended family, guests, or potential rental income to help offset monthly mortgage expenses. With its unique layout and numerous private living spaces, the property may also offer exciting potential for a bed-and-breakfast or similar hospitality use, subject to applicable town approvals and permitting. Additional highlights include two separate parking areas, a large deck and patio with a firepit, and a two-story barn offering space for storage, hobbies, a workshop, or a potential office. Loved by the same family for years, this home is filled with natural light, inviting gathering spaces, and room to grow. Located in desirable Brookline, the property offers the charm of a small New Hampshire town with convenient access to local amenities, conservation land, and Brookline’s extensive network of trails. SELLERS ARE OFFERING A $25,000 CLOSING CREDIT toward painting, carpeting, an interest-rate buy-down, or other allowable buyer closing costs!

15 Pepperell Rd, Brookline

$1,075,000

PRICE IMPROVEMENT 8/4/26! A rare multigenerational opportunity in Brookline, this thoughtfully rebuilt property offers exceptional space, flexibility, and income-producing potential. The main residence features three bedrooms, a finished attic, a private guest suite with a kitchenette and bathroom, and a spacious chef’s kitchen with abundant counter space, storage, and a beautiful copper sink. The legal two-bedroom ADU includes its own kitchen, living room, and bathroom, making it ideal for extended family, guests, or potential rental income to help offset monthly mortgage expenses. With its unique layout and numerous private living spaces, the property may also offer exciting potential for a bed-and-breakfast or similar hospitality use, subject to applicable town approvals and permitting. Additional highlights include two separate parking areas, a large deck and patio with a firepit, and a two-story barn offering space for storage, hobbies, a workshop, or a potential office. Loved by the same family for years, this home is filled with natural light, inviting gathering spaces, and room to grow. Located in desirable Brookline, the property offers the charm of a small New Hampshire town with convenient access to local amenities, conservation land, and Brookline’s extensive network of trails. SELLERS ARE OFFERING A $25,000 CLOSING CREDIT toward painting, carpeting, an interest-rate buy-down, or other allowable buyer closing costs!

5 Beds ⋅ 7 Baths ⋅ 5084927 MLS

PRICE IMPROVEMENT 8/4/26! A rare multigenerational opportunity in Brookline, this thoughtfully rebuilt property offers exceptional space, flexibility, and income-producing potential. The main residence features three bedrooms, a finished attic, a private guest suite with a kitchenette and bathroom, and a spacious chef’s kitchen with abundant counter space, storage, and a beautiful copper sink. The legal two-bedroom ADU includes its own kitchen, living room, and bathroom, making it ideal for extended family, guests, or potential rental income to help offset monthly mortgage expenses. With its unique layout and numerous private living spaces, the property may also offer exciting potential for a bed-and-breakfast or similar hospitality use, subject to applicable town approvals and permitting. Additional highlights include two separate parking areas, a large deck and patio with a firepit, and a two-story barn offering space for storage, hobbies, a workshop, or a potential office. Loved by the same family for years, this home is filled with natural light, inviting gathering spaces, and room to grow. Located in desirable Brookline, the property offers the charm of a small New Hampshire town with convenient access to local amenities, conservation land, and Brookline’s extensive network of trails. SELLERS ARE OFFERING A $25,000 CLOSING CREDIT toward painting, carpeting, an interest-rate buy-down, or other allowable buyer closing costs!

15 Pepperell Rd, Brookline