Houses for Sale near Winsor School

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  /37

  $9,450,000

  • 4 Beds
  • 5.5 Baths
  • 5,194 Sq Ft

  32 Lime St, Boston, MA 02108

  An exquisite city-center residence in an ambiance seeming like a tranquil garden suburb, this one-of-a-kind circa 1914 townhouse by noted architect Richard Arnold Fisher stands on a tree-canopied, block-long street on the Flat of Beacon Hill. Inspired by English traditions, this beautifully livable jewel with six fireplaces has been tastefully restored and renovated by its long-time current

  The Mazer Group Compass

  32 Lime St, Boston, MA 02108
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  /35

  $1,225,000 Open Sat 2PM - 3:30PM

  • 3 Beds
  • 2.5 Baths
  • 1,514 Sq Ft

  6-8 Watson St Unit 8, Cambridge, MA 02139

  CAMBRIDGEPORT | Townhouse condo that lives like a single family w/ nobody above or below + very low condo fee! Nestled on a quiet residential street yet just moments to Central/Kendall/MIT !Many recent updates throughout. Fully renovated kitchen w/ Quartz counters, Bosch appliances and open layout into large living and dining rooms w/ high ceilings and newly refinished hardwood floors. Second

  Tim McDonald Berkshire Hathaway HomeServices Commonwealth Real Estate

  6-8 Watson St Unit 8, Cambridge, MA 02139
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  /36

  $899,800 Open Sat 1PM - 2:30PM

  • 4 Beds
  • 1.5 Baths
  • 1,546 Sq Ft

  4 Remick Terrace, Newton, MA 02458

  Offers due by 1pm on Tuesday, Nov 11. Fantastic home in a great location on very pretty dead-end street Remick Terrace in a convenient location being only .5 mile from Starbuck's down the street, around the corner from getting on the Mass Pike and only 1.4 miles the the Newtonville T-station! Home shows wonderfully with 2 car garage, 4 bedrooms, gleaming hardwood floors everywhere, fantastic

  John J. Allaire Easton Real Estate, LLC

  4 Remick Terrace, Newton, MA 02458
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  /13

  $690,000

  • 4 Beds
  • 3 Baths
  • 1,818 Sq Ft

  30 Glenhill Rd, Mattapan, MA 02126

  Located minutes to major highways and public transportation, this home feels like Serenity in the City. Not 1 but 2 Master Suites. Open concept living/dining area. Insulated Storage/Shed Move in Ready!!!

  Delfredia Dancy Delfredia J. Dancy

  30 Glenhill Rd, Mattapan, MA 02126
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  /39

  $4,850,000 Open Sat 10AM - 12PM

  • 4 Beds
  • 5 Baths
  • 4,013 Sq Ft

  32 W Cedar St, Boston, MA 02108

  Federal style single family townhome with elevator & large deep private garden on enviable West Cedar St between Mt Vernon and Pinckney only 1 block from Charles Street. Renovated by Payne Bouchier, this property offers over 4000SF across 5 floors. Double parlor at entry level allows for flexible living options, gas fireplace, high ceilings, original detail, coat closet, powder room & office area

  The Biega + Kilgore Team Compass

  32 W Cedar St, Boston, MA 02108
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  /41

  $979,000 Open Sun 11AM - 12:30PM

  • 3 Beds
  • 2.5 Baths
  • 1,824 Sq Ft

  122 Burget Ave, Medford, MA 02155

  On a cul de sac near the new T station, this SF has so much to offer: 3 bdrms, 2.5 baths, 1st floor w/d, lg deck off kitchen, 2 car garage with driveway, and private backyard. From the front dr, you step into the LR. Thru a French dr on the right is a cozy office. A curved arch leads from LR to DR w/lg windows and MCM pendant lt. Off the DR is a laundry and 1/2 bath w/ linen closet and window.

  Thalia Tringo Thalia Tringo & Associates Real Estate, Inc.

  122 Burget Ave, Medford, MA 02155
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  /24

  $1,299,000

  • 3 Beds
  • 2 Baths
  • 1,202 Sq Ft

  607 E 2nd St, Boston, MA 02127

  2-1 rate buy down offered by seller. Own this home with monthly payments of just $4,443.08* with the offered buy down. Welcome to 607 E 2nd Street, a well-maintained single-family home offering two levels of finished living space above a two-car garage, plus an unfinished attic for future expansion. The first floor features a guest bedroom, a full bathroom, and a bright kitchen with beautiful

  Adam Burns Burns Realty & Investments LLC

  607 E 2nd St, Boston, MA 02127
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  /35

  $2,795,000 Open Sun 12PM - 1PM

  • 5 Beds
  • 6 Baths
  • 5,994 Sq Ft

  71 Farina Rd, Newton Center, MA 02459

  Welcome to this stunning, meticulously maintained South Side contemporary home offering nearly 6,000 square feet of luxurious living space! A dramatic two-story, granite foyer welcomes you to a multi-tiered living room with walls of glass, soaring vaulted ceilings and French doors leading to a patio providing picturesque views of your private yard and in-ground pool. The main floor also features

  Janice Lipof Hammond Residential Real Estate

  71 Farina Rd, Newton Center, MA 02459
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  /18

  $649,000

  • 3 Beds
  • 1 Bath
  • 908 Sq Ft

  12-14 Shannon St Unit 3, Boston, MA 02135

  Rarely available 3-bedroom condo in the heart of Brighton Center! This super sunny, top-floor 3-bed condo with garage parking (and 2 additional tandem parking spaces) is just blocks to the shops, cafes and restaurants of bustling Brighton Center. Unit features an open floorplan with hardwood floors throughout, living room with recessed lighting, newer kitchen appliances, in-unit laundry, and

  Dan Keating Coldwell Banker Realty - Brookline

  12-14 Shannon St Unit 3, Boston, MA 02135
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  /42

  $1,475,000 Open Sun 11AM - 12PM

  • 4 Beds
  • 2.5 Baths
  • 1,950 Sq Ft

  81 Winsor Ave, Watertown, MA 02472

  Welcome to your dream home! Gorgeous, fully renovated Colonial on a corner lot in the desirable Oakley Country Club area. With 4 bedrooms, 2.5 baths, this home is bright, spacious, and move-in ready. Experience open concept living that features a cozy fireplace and stunning hardwood floors throughout. The kitchen boasts gorgeous quartz waterfall countertops and stainless-steel appliances. The

  Chris Gentile RTN Realty Advisors LLC.

  81 Winsor Ave, Watertown, MA 02472
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  /42

  $1,099,000 Open Sun 12:30PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 2,025 Sq Ft

  89 Heath St, Somerville, MA 02145

  Welcome to 89 Heath Street! Why go condo when you can own this stunning single-family home, just minutes to Magoun Square, that checks all the boxes! The main level offers an open floor plan with living room, dining room, half bath, family room, and fully appliance kitchen with gas cooking, tiled floor, and breakfast bar. The second floor has 3 large bedrooms and offers a great option for a home

  Bob Bittelari Berkshire Hathaway HomeServices Commonwealth Real Estate

  89 Heath St, Somerville, MA 02145
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  /22

  $1,150,000 Open Sat 11:30AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  44 Newbern St, Jamaica Plain, MA 02130

  Step back in time while enjoying modern comfort in this 1890s Colonial. Full of character and timeless craftsmanship, this home showcases the classic details of the time period. Lovingly cared for by the owners for over 50 years, it blends historic charm with thoughtful infrastructure updates. 44 Newbern features 3 Beds and 2 Full Baths with the opportunity to add another bath to the 2nd floor.

  Timothy Naber Gilmore Murphy Realty LLC

  44 Newbern St, Jamaica Plain, MA 02130
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  /28

  $1,749,000

  • 3 Beds
  • 2.5 Baths
  • 2,185 Sq Ft

  209 W 2nd St, Boston, MA 02127

  Rare free-standing single-family home, custom built, ideally located near the Convention Center and Seaport District. This unique residence offers a perfect blend of privacy, luxury, and convenience, with direct access heated garage parking, tandem driveway space, and three outdoor areas—including two decks and a roof deck with 360 views of the Boston skyline. Inside, enjoy an open fireplaced

  Jin Wang Wang & Associates

  209 W 2nd St, Boston, MA 02127
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  /15

  $1,465,000

  • 3 Beds
  • 2.5 Baths
  • 2,389 Sq Ft

  1 Channing St, Newton, MA 02458

  Nestled at 1 Channing St, Newton, MA, this single-family residence presents a unique opportunity to own a piece of history, exhibiting the charm of its 1874 origins. The property awaits its next chapter, all ready transformed into a modern sanctuary while retaining its period character. With 2389 square feet of living area, this home offers ample space to create distinct living zones. A living

  Tom Lambert Berkshire Hathaway HomeServices Commonwealth Real Estate

  1 Channing St, Newton, MA 02458
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  /25

  $7,250,000

  • 6 Beds
  • 6.5 Baths
  • 6,396 Sq Ft

  3 Berkeley Place, Cambridge, MA 02138

  This Harvard Square residence is sited on a charming private way, offering generously scaled rooms designed for work, play, and relaxation. Through the stunning 2-story foyer, the living room and library each have a gas fireplace and custom built-ins. The dining room also has a fireplace and French doors to the beautiful fenced-in backyard with gardens. The eat-in chef's kitchen is equipped with

  Gail Roberts, Ed Feijo & Team Coldwell Banker Realty - Cambridge

  3 Berkeley Place, Cambridge, MA 02138
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  /39

  $729,000

  • 2 Beds
  • 2.5 Baths
  • 1,336 Sq Ft

  27 Carter St Unit 2, Everett, MA 02149

  Welcome to 27 Carter St, where luxury, convenience & lifestyle converge. This stunning 3-level townhouse offers sun-drenched open spaces, luxury hardwood floors, a chef’s kitchen with natural stone counters & stainless appliances. TWO ensuite bedrooms with spa-inspired baths & custom walk-in closets. A versatile bonus room, private deck/patio & garage elevate your comfort every day. Truly

  Katie Ngan Vien eXp Realty

  27 Carter St Unit 2, Everett, MA 02149
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  /34

  $1,700,000

  • 3 Beds
  • 3.5 Baths
  • 2,426 Sq Ft

  83 Payson Rd, Chestnut Hill, MA 02467

  Turn Key residence blending classic charm and modern upgrades. Added square footage from a 2021 renovation. Major upgrades include new roof and rebuilt garage (2021) with Tesla charging station, furnace and A/C (2023), and on-demand water heater (2024).Features include a renovated kitchen (2018–2020) with dual-fuel stove, open floor plan, and oak hardwoods throughout. The living room boasts a

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  83 Payson Rd, Chestnut Hill, MA 02467
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  /36

  $649,900

  • 4 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  539 Lagrange St, West Roxbury, MA 02132

  Welcome to 539 Lagrange Street! This cozy custom bungalow's next chapter starts with you! There is much to love from the french doors that greet you at the entry foyer to the wood burning fire place as the focal point of the large living room with built-in display cabinetry. Hardwood floors flow throughout the first floor into the 2 generously-sized bedrooms, a full bath plus renovated kitchen

  Brian Clinton Donahue Real Estate Co.

  539 Lagrange St, West Roxbury, MA 02132
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  /27

  $720,000

  • 4 Beds
  • 1.5 Baths
  • 1,424 Sq Ft

  43 Aldrich St, Roslindale, MA 02131

  Antique Colonial Charm in Prime Roslindale Location! Rare opportunity to own a piece of history—this 1884 Colonial is full of character and waiting for your personal touch. Nestled on a quiet street with easy access to major highways, this home offers a small, manageable yard, off-street parking, and endless potential. Original details throughout, with high ceilings and classic period woodwork.

  Christopher Rogers Century 21 The Real Estate Group

  43 Aldrich St, Roslindale, MA 02131
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  /29

  $920,000

  • 4 Beds
  • 1.5 Baths
  • 1,906 Sq Ft

  21 Upcrest Rd, Brighton, MA 02135

  Welcome to this charming four-bedroom Colonial tucked away on a quiet dead-end street, just a short walk to Oak Square and local shops. This beautifully updated home features brand-newhardwood flooring throughout, a newly added half bath, and new windows on the way, offering comfort, style, and energy efficiency. The spacious first floor includes a sun-filled, front-to-back12x23 living

  Sam Zhu Keller Williams Realty

  21 Upcrest Rd, Brighton, MA 02135
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  /42

  $2,090,000

  • 3 Beds
  • 2.5 Baths
  • 2,668 Sq Ft

  31 W Boulevard Rd, Newton Center, MA 02459

  Charming Tudor with great curb appeal in the sought-after Ward School district. Gracious foyer opens to formal living & dining rooms, updated kitchen (granite, Sub-Zero, 5-burner gas), and spacious family & sunrooms—both with fireplaces. Excellent flow for everyday living & entertaining, with access to patio, yard, and garage.Upstairs offers a large primary suite with remodeled bath, custom

  Dan Wu Hooli Homes Boston

  31 W Boulevard Rd, Newton Center, MA 02459
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  /42

  $7,995,000

  • 7 Beds
  • 11 Baths
  • 8,921 Sq Ft

  55 Leicester St, Brookline, MA 02445

  55 Leicester offers a rare opportunity in one of Brookline’s premier, private locations. Behind its grand facade and dramatic floating staircase, this expansive estate awaits its next chapter. While the home showcases soaring ceilings, walls of windows overlooking landscaped grounds, and an open, light-filled floor plan, it is ready for a visionary buyer to reimagine and restore its full

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  55 Leicester St, Brookline, MA 02445
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  /42

  $3,950,000

  • 4 Beds
  • 5 Baths
  • 3,788 Sq Ft

  22 Joy St, Boston, MA 02114

  Exceptionally Renovated Single-Family Townhouse that exudes comfort and warmth. The home features 4 bedrooms, 3 full bathrooms, 2 half bathrooms and beautiful hardwood floors thru-out the home. The open entry level features a lovely living room with completely restored soundproof staircase, custom built-in bookcases, fireplace and 2 large windows that bring in natural Sunlight. The

  Janet Lamb Sterling Beacon Hill

  22 Joy St, Boston, MA 02114
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  /16

  $12,500,000

  • 6 Beds
  • 6 Baths
  • 7,502 Sq Ft

  71 Sears Rd, Brookline, MA 02445

  This is one of Brookline's most exceptional properties to hit the market in over a decade. Located in the prestigious estate area, this stunning 1929 Colonial Revival home offers 14 rooms and is set on two lush acres. The property features an inviting in-ground pool, sweeping lawns, specimen trees, perennial gardens, and a serene, man-made freshwater creek. With approximately 7,000 square feet of

  Michael & Conor Chamberlain Coldwell Banker Realty - Brookline

  71 Sears Rd, Brookline, MA 02445
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  /29

  $9,700,000

  • 5 Beds
  • 6.5 Baths
  • 8,750 Sq Ft

  88 Essex Rd, Chestnut Hill, MA 02467

  Welcome to 88 Essex Road, a breathtaking home located on over an acre of land, on a private road in the heart of Chestnut Hill, Newton. This residence features 5+ spacious bedrooms and an open and airy layout. The first floor includes an expansive chef’s kitchen which is open to a bright breakfast area and family room, while the spacious living and dining rooms flow seamlessly to a patio, perfect

  Maggie Gold Seelig MGS Group Real Estate LTD

  88 Essex Rd, Chestnut Hill, MA 02467
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  /42

  $2,300,000 Open Sun 12:30PM - 2PM

  • 5 Beds
  • 4.5 Baths
  • 2,602 Sq Ft

  30 2nd St Unit 2, Cambridge, MA 02141

  Welcome to the ultimate urban living experience w/ flexibility to suit your personal needs. This beautifully modernized 1840s brick townhouse combines historic details w/ flexibility to suit a variety of lifestyles. Spanning 4 levels, it features 5 spacious bedrooms, 4 full baths, a half-bath, 2 kitchens, and 4 dedicated off-street parking spaces. The two units offer versatility as a

  Lisa Drapkin Compass

  30 2nd St Unit 2, Cambridge, MA 02141
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  /17

  $1,198,000 Open Sat 1PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,240 Sq Ft

  18 Chestnut Place, Brookline, MA 02445

  Welcome to this one-of-a-kind home nestled in a stunning private setting. This condo offers the feel of a single family home, with the perks of an association. Completely separate from the high-rise building of Sargent Estates, this single-story ranch-style property is tucked away with its own driveway and outdoor space. When you walk in, you'll find an open floor plan, kitchen featuring white

  Jeff Groper Coldwell Banker Realty - Newton

  18 Chestnut Place, Brookline, MA 02445
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  /28

  $9,900,000

  • 23 Beds
  • 12 Baths
  • 14,256 Sq Ft

  395 Commonwealth Ave, Boston, MA 02215

  Introducing the Ayer Mansion, widely regarded as one of the most stunning and distinctive addresses on Commonwealth Avenue in Back Bay. A National Historic Landmark, the Ayer Mansion is the last surviving example of a complete residential commission by the famed American artist, designer, and craftsman Louis Comfort Tiffany. Tiffany combined exotic architectural style with masterful design

  Tracy Campion Campion & Company Fine Homes Real Estate

  395 Commonwealth Ave, Boston, MA 02215
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  /22

  $8,750,000

  • 5 Beds
  • 6 Baths
  • 6,082 Sq Ft

  9 Walnut St, Boston, MA 02108

  Grand and wide South Slope single family townhouse with elevator to every floor! This gracious ultra wide Beacon Hill home has been fully renovated and upgraded with many recent capital improvements to systems and structure. Offering 5+ bedrooms, 4 full and 2 half baths, this wonderful home has an excellent scale with enormous floor to ceiling windows, soaring ceiling heights on every floor, a

  Michael Harper Coldwell Banker Realty - Boston

  9 Walnut St, Boston, MA 02108
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  /12

  $2,650,000

  • 5 Beds
  • 2.5 Baths
  • 4,080 Sq Ft

  22 Harvard St, Charlestown, MA 02129

  Steps to downtown Boston - 22 Harvard Street in Charlestown - OVERSIZED Single-Family home presents a unique opportunity to own a piece of history within a vibrant community. Built in 1880, this property offers a glimpse into a historic era, providing a substantial footprint for contemporary living. The residence boasts a generous 4,080 SF of living space, encompassing five bedrooms, creating an

  Sarah Sherrow Alcove Realty

  22 Harvard St, Charlestown, MA 02129
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  /6

  $649,999

  • 3 Beds
  • 2 Baths
  • 1,354 Sq Ft

  192 Walnut Ave Unit 3, Roxbury, MA 02119

  192 Walnut Ave is a luxurious 3-bedroom, 2-bath condo that blends modern design and premium upgrades. Built in 2018, it features a spacious design built for entertainment, two private decks and views of the city skyline.This condo is walking distance to many amenities, including Franklin Park Zoo and White Stadium, which will serve as the new headquarters for the National Women's Soccer League.

  Jessica Thomas MIG

  192 Walnut Ave Unit 3, Roxbury, MA 02119
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  /42

  $1,199,000 Open Sun 11:30AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,679 Sq Ft

  107 Minot St, Dorchester, MA 02122

  PRICE REDUCTION! Rare opportunity to own a beautiful single-family colonial on an enormous 10,000+ sq. ft. lot with exciting development potential in one of Dorchester’s most sought-after neighborhoods. Located in the heart of Adams Village / Neponset, this home features three spacious bedrooms and two full baths, blending classic charm with comfort. The oversized lot provides incredible

  Joseph McEachern Paramount Properties

  107 Minot St, Dorchester, MA 02122
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  /21

  $899,000

  • 3 Beds
  • 3 Baths
  • 1,821 Sq Ft

  66 Farquhar St Unit A, Roslindale, MA 02131

  Discover modern luxury at 66 Farquhar St, Unit A! This like-new 3 bed, 3 bath condo offers over 1,800 SqFt of sun-filled living space with gleaming hardwood floors, a designer kitchen with stainless steel appliances & frameless cabinetry, and three beautifully tiled baths. The flexible layout features three spacious bedrooms, including two lower-level suites with en-suite baths. Enjoy private

  Team Galvin The Galvin Group, LLC

  66 Farquhar St Unit A, Roslindale, MA 02131
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  /23

  $5,500,000

  • 3 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  136 Dudley Rd, Newton Center, MA 02459

  Rarely available 3.25-acre property on Newton's South Side offers an exceptional development opportunity in an estate property area. The site is located on picturesque Dudley Road, surrounded by mature trees and expensive homes. There is currently a 4,200sf antique barn on the property that was converted to a residence 50 years ago. This residence has 4 bedrooms, 3 bathrooms and a 2-car garage.

  Ezra Stillman Hammond Residential Real Estate

  136 Dudley Rd, Newton Center, MA 02459
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  /42

  $1,679,000

  • 7 Beds
  • 3.5 Baths
  • 4,428 Sq Ft

  37 Pomfret St, West Roxbury, MA 02132

  "Spectacular and Spacious" describes this grand Victorian! This wonderful home offers 4 floors of living! On the 1st floor: a welcoming sitting room, living room, formal dining room eat-in kitchen, stunning and comfortable family room and a lavatory! The second floor: 4 large bedrooms, 2 full baths and a very convenient laundry! The 3rd floor boasts a master suite with a full bath and 2

  Stevedoug.com Team LAER Realty Partners

  37 Pomfret St, West Roxbury, MA 02132
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  /37

  $799,999

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  7 French St, Watertown, MA 02472

  Only steps from Main Street, this classic three-bedroom Cape offers timeless charm, solid construction, and a location that puts everyday conveniences close at hand. Restaurants and cafés along Main Street are just 0.3 miles away, with shops, parks, and the Charles River Greenway all within easy reach. Inside, fresh off-white paint in several rooms provides a refreshed look, paired with hardwood

  Mike DelRose Coldwell Banker Realty - Belmont

  7 French St, Watertown, MA 02472
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  /38

  $1,700,000

  • 4 Beds
  • 2.5 Baths
  • 3,188 Sq Ft

  22 Kenilworth St, Roxbury, MA 02119

  Historic charm meets modern living in this 4BR/2.5BA 1860 brick single-family nestled at the foot of Fort Hill. With 2,100 sf of living space, the main level of this home features an open kitchen with Quartzite counters, Samsung white glass appliances, electrified island, tiled backsplash, and four fireplaces. The second floor offers three bedrooms and a stylish bath with double vanity, tile

  Brian Perry Gibson Sotheby's International Realty

  22 Kenilworth St, Roxbury, MA 02119
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  /42

  $2,695,000

  • 4 Beds
  • 4.5 Baths
  • 2,430 Sq Ft

  137 Walden St Unit 137, Cambridge, MA 02140

  This modern townhouse near Raymond and Danehy Parks offers luxurious indoor and outdoor living with refined finishes throughout. The sunlit main floor flows from the living room to the dining area and onto a spacious mahogany deck overlooking a beautifully landscaped perennial garden. The chef’s kitchen features Thermador appliances, an induction cooktop and custom European cabinetry. Wide-plank

  Joseph Pollack Redfin Corp.

  137 Walden St Unit 137, Cambridge, MA 02140
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  /35

  $2,199,000 Open Sun 12PM - 1PM

  • 3 Beds
  • 4 Baths
  • 2,676 Sq Ft

  9 Short St, Charlestown, MA 02129

  Searching for the perfect city oasis to raise a family and entertain? This freestanding single-family home checks every box with a heated two-car garage, oversized fenced yard, and quiet street in the heart of the city. Fully renovated, it blends modern style with comfort. The open layout features a spacious living room with gas cobblestone fireplace and a chef’s kitchen with high-end appliances,

  Chris Tuite Compass

  9 Short St, Charlestown, MA 02129
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  /20

  $550,000

  • 4 Beds
  • 1.5 Baths
  • 1,965 Sq Ft

  14-14R Kennebec St, Boston, MA 02126

  Tucked away on a quiet, private street in the heart of Mattapan, this spacious home offers a rare opportunity at a single-family price—with the flexibility to explore multi-family possibilities. Featuring multiple levels of living space, an enclosed porch, and a fully fenced yard, this property is perfect for investors looking to capitalize on zoning potential or owner-occupants eager to

  Danielle Canty Keller Williams Realty Boston South West

  14-14R Kennebec St, Boston, MA 02126

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