Homes for Sale near Winsor School

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  /10

  $799,500 Open Sun 12PM - 1PM

  • 1 Bed
  • 1 Bath
  • 625 Sq Ft

  354 Beacon St Unit 5, Boston, MA 02116

  Fantastic, Beacon St., Front Facing, 1 bed/1 bath, in well managed Back Bay Brownstone. Elegantly appointed second floor, front facing 1bed/1 bath, with renovated kitchen, spacious living room, generous sized bedroom and plenty of common closets. Enjoy your breakfast in the dining nook or work from home and enjoy the beautiful tree line views of Beacon st. Have friends over and watch a game in

  Danny Allen Coldwell Banker Realty - Boston

  354 Beacon St Unit 5, Boston, MA 02116
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  /20

  $475,000

  • 2 Beds
  • 1 Bath
  • 971 Sq Ft

  7 Bailey St Unit 2, Dorchester Center, MA 02124

  Amazing opportunity for first time home buyer or savvy investor. Conveniently located in the Ashmont neighborhood, this spacious condo awaits your personal touch - nothing but upside! The primary bedroom is tucked away for peace & quiet and has two closets. The second bedroom has a large walk-in closet – perfect for home office or guest room. Open concept living room-dining room combo offers

  Tara O'Riordan Coldwell Banker Realty - Dorchester

  7 Bailey St Unit 2, Dorchester Center, MA 02124
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  /11

  $689,900

  • 4 Beds
  • 2 Baths
  • 1,200 Sq Ft

  30 Glenville Ave Unit 1, Boston, MA 02134

  Cash Cow! Rare opportunity to own this well-maintained unit in the heart of Allston. It has had a very strong cash flow for the past 10 years. The unit currently has a lease of $4,300 until August 2026! You can collect rent from day 1. Spacious 4-bedroom in the heart of Allston. It is all FURNISHED!!! Heat and Hot water included. Farirly new kitchen and bathroom. Tons of restaurants nearby. 3 min

  Zhou Chen Blue Ocean Realty, LLC

  30 Glenville Ave Unit 1, Boston, MA 02134
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  /39

  $6,900,000

  • 4 Beds
  • 4 Baths
  • 4,093 Sq Ft

  190 Marlborough St Unit C, Boston, MA 02116

  Beautifully maintained 4-bed, 4-bath upper triplex offering over 4,000 sq ft in a historic Marlborough St home. The main level includes a formal living room with floor-to-ceiling windows, custom kitchen with Wolf & Thermador appliances, dining banquette, and family room with fireplace. The full-floor primary suite features a luxurious bath with soaking tub, steam shower, dual vanities, walk-in

  david sampson Real Broker MA, LLC

  190 Marlborough St Unit C, Boston, MA 02116
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  /24

  $724,000

  • 2 Beds
  • 2.5 Baths
  • 1,129 Sq Ft

  216 Havre St Unit 4, Boston, MA 02128

  Stunning Duplex Penthouse in East Boston! Built in 2021 by one of the area’s top builders, this home feels better than new. The main level offers an open layout with a two-toned kitchen, large quartz peninsula, hardwood floors, designer lighting, and a private deck with a half bath nearby — perfect for entertaining. Upstairs features two spacious bedrooms, including a serene primary suite with

  Stone Prum Corcoran Property Advisors

  216 Havre St Unit 4, Boston, MA 02128
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  /13

  $485,000

  • 4 Beds
  • 1 Bath
  • 1,190 Sq Ft

  305R Lexington St, East Boston, MA 02128

  ***DEAL ALERT*** Welcome to 305-R Lexington St! Super desirable Eagle Hill location. This 4 bed, 1 bath, single family home has been owned and loved by the same family for over 70 years! It's time for the next generation to take the reins and bring this property into the 21st century. House is set back from the road on a unique L shaped lot giving you your own gated entry and fenced in yard!

  Joseph Gindi Realty One Group Next Level

  305R Lexington St, East Boston, MA 02128
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  /27

  $599,000

  • 1 Bed
  • 1.5 Baths
  • 899 Sq Ft

  250 Hammond Pond Pkwy Unit 1604N, Chestnut Hill, MA 02467

  This sprawling condominium with 16th floor awe-inspiring views is truly a rare find at the Towers of Chestnut Hill. This corner unit showcases wonderful space, light and well-proportioned rooms and expands nearly 1000 sq. ft. and feels even larger. Truly panoramic unobstructed views from every room allow the perfect backdrop for entertaining. From the moment you drive up to the circular drive,

  Richard C. Dore Hammond Residential Real Estate

  250 Hammond Pond Pkwy Unit 1604N, Chestnut Hill, MA 02467
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  /37

  $1,169,000

  • 2 Beds
  • 2 Baths
  • 1,349 Sq Ft

  309 E St Unit 46, Boston, MA 02127

  HOLIDAY SPECIAL up to 12/31: 20K Cash Back at Closing . Stunning penthouse corner 2 bed/2 bath unit at The Residences at Dahlgren Hall. Rare unit offers city views, luxury finishes, exceptional amenities, and 1 garage parking space. Formerly owned by a musician from The Voice, this unit includes a custom acoustic wall feature that elevates both style and sound. Enjoy an open layout, marbled

  Drew Boujoulian Coldwell Banker Realty - Boston

  309 E St Unit 46, Boston, MA 02127
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  /40

  $9,450,000

  • 4 Beds
  • 7 Baths
  • 4,754 Sq Ft

  352 Marlborough St, Boston, MA 02115

  Nestled on picturesque Marlborough Street, this renovated 4-bedroom, 4-full, and 3-half-bathroom single-family home seamlessly blends modern luxury with Back Bay’s timeless charm. Designed to the highest standards, it offers both contemporary comfort and historic grandeur. An elevator serves all levels, culminating in a family/media room with a rooftop terrace. The entire third floor is dedicated

  Michael Carucci Gibson Sotheby's International Realty

  352 Marlborough St, Boston, MA 02115
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  /16

  $639,000 Open Sun 2PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,159 Sq Ft

  60 Stanley St Unit 303, Boston, MA 02125

  **On select remaining units, take home $20,000 in closing credits!** A new expression of modern luxury awaits at Dorchester’s newest boutique eight-unit residence, where modern luxury meets thoughtful, design-driven craftsmanship. This exclusive new construction showcases soaring nine-foot ceilings and walls of oversized windows that bathe the home in natural light while offering breathtaking

  Brandon Fisher Coldwell Banker Realty - Brookline

  60 Stanley St Unit 303, Boston, MA 02125
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  /13

  $634,900

  • 2 Beds
  • 1 Bath
  • 590 Sq Ft

  260 Sidney St Unit 3R, Cambridge, MA 02139

  Discover the allure of this sunlit penthouse with two spacious bedrooms in a charming brick building near Central Square. The kitchen combines style and functionality with granite countertops, stainless steel appliances, and a convenient desk nook. Enjoy your private deck, ideal for outdoor dining and relaxation. The L-shaped living area offers a distinct dining space, complemented by warm maple

  Aranson Maguire Group Compass

  260 Sidney St Unit 3R, Cambridge, MA 02139
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  /26

  $499,000

  • 3 Beds
  • 1 Bath
  • 1,062 Sq Ft

  17 Greendale Rd Unit 2F, Boston, MA 02126

  Second floor unit in a six-unit, building, unit has three bedrooms and 1 bathroom, hardwood floors throughout, tiles in the kitchen and bathroom, unit has been renovated. Laundry in unit. Building exterior was renovated in 2024, updates include, windows, roof, siding, fence, front doors in common areas, paved driveway. Each unit has a storage area in the basement, off street parking for one

  Velenor Walker Stratton Coldwell Banker Realty - Milton

  17 Greendale Rd Unit 2F, Boston, MA 02126
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  /15

  $875,000

  • 2 Beds
  • 1.5 Baths
  • 994 Sq Ft

  30 2nd St Unit 2, Cambridge, MA 02141

  Welcome to the ultimate urban living experience w/ flexibility to suit your personal needs. Spanning 2 levels, this home features 2 spacious bedrooms, 2 full baths and 2 dedicated off-street parking spaces. In vibrant East Cambridge, the home overlooks a curated garden park and is a short stroll to the Charles River’s scenic paths. The new Lechmere Green Line station, Cambridge Crossing shops,

  Lisa Drapkin Compass

  30 2nd St Unit 2, Cambridge, MA 02141
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  /21

  $995,000

  • 2 Beds
  • 1 Bath
  • 940 Sq Ft

  249 Corey Rd Unit 306, Boston, MA 02135

  Welcome to The Jordan, Brighton’s newest boutique condominium ideally located on the Brookline town line. This well-designed complex features 34 modern units, just steps from Whole Foods and public transportation, offering unparalleled convenience for urban living. Residents enjoy premium amenities, including a landscaped private courtyard with grill, a spacious rooftop terrace with 360 views, a

  Dean Poritzky Engel & Völkers Wellesley

  249 Corey Rd Unit 306, Boston, MA 02135
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  /9

  $1,249,000

  • 10 Beds
  • 3 Baths
  • 3,321 Sq Ft

  42 Monadnock St, Dorchester, MA 02125

  We are excited to offer this 3-unit multifamily property. The property is made up of one 4-bedroom / 1-bathroom apartment and two 3-bedroom / 1-bathroom apartments. Located in the heart of Dorchester, the building enjoys direct access to area amenities and excellent connectivity with multiple bus lines for access to downtown Boston. With 3 units in place, and two units currently vacant, the asset

  Kevin Benzinger Boston Realty Advisors

  42 Monadnock St, Dorchester, MA 02125
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  /27

  $1,299,000

  • 3 Beds
  • 2 Baths
  • 1,390 Sq Ft

  560 E 5th St Unit 2, Boston, MA 02127

  Introducing 560 East 5th Street, Southie, a stunning 2021 new construction offering roughly 1400 sq. ft. of luxury living, featuring 3 bedrooms, 2 bathrooms, private direct-access deck, and garage parking. Blazing south-facing exposure floods the home with natural light throughout the day. Set within an impeccably restored Victorian residence and carriage house, this exceptional property blends

  Alex Mackenzie Compass

  560 E 5th St Unit 2, Boston, MA 02127
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  /15

  $2,650,000

  • 6 Beds
  • 3 Baths
  • 3,294 Sq Ft

  153 Bowen St, Boston, MA 02127

  Built from the ground up in 2021, contemporary 3 unit building features 2 bedroom, 1 bathroom apartments, all with a private balcony, common roof deck and garage parking. Modern kitchens with breakfast bar, shaker style cabinetry and stainless steel appliances. Hardwood floors throughout, large bathrooms with stackable washer and dryer. Equal size bedrooms, great for roommates. Property includes

  Patti Donovan Keliher Real Estate

  153 Bowen St, Boston, MA 02127
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  /24

  $3,199,000 Open Sun 12PM - 1:30PM

  • 16 Beds
  • 8 Baths
  • 6,700 Sq Ft

  83-85 Surrey St, Boston, MA 02135

  Beautiful Brighton Center Four family. 218K Annual Income. This magnificent beauty boasts high ceilings with large windows that allow a ton of natural sunlight. Fully renovated units with Stainless Steel appliances and Eat-in-Kitchens with Granite Countertops and Gleaming hardwood floors throughout. Outdoor deck overlooks large, private, fenced-in backyard. All units have In-Unit Laundry and are

  Jerome Bibuld Red Tree Real Estate

  83-85 Surrey St, Boston, MA 02135
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  /18

  $799,000

  • 1 Bed
  • 1 Bath
  • 777 Sq Ft

  580 Washington St Unit 304, Boston, MA 02111

  An ideal pied-à-terre with an attractive price and low monthly HOA fees for top-notch services and resident amenity spaces. Not to be missed - this one-bedroom condo provides a thoughtful layout with well-distributed living spaces. The open-concept kitchen has solid wood cabinetry, granite countertops, top-grade integrated and paneled appliances, and ample storage space. The marble-appointed

  Brett DeRocker First Boston Realty International

  580 Washington St Unit 304, Boston, MA 02111
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  /41

  $1,225,000

  • 2 Beds
  • 2.5 Baths
  • 1,527 Sq Ft

  321 Hammond Pond Pkwy Unit 301, Chestnut Hill, MA 02467

  Perfectly situated third floor corner unit at Hammond Pond Place Condominium, a 12-year young 27-unit luxury building located just steps from Route 9 / Chestnut Hill shopping, dining, movie and outdoor recreation / activity...This 3rd floor corner unit has abundant windows on two sides and sliders from master bedroom to 350+ sq ft private terrace, allowing natural light to stream in...the terrace

  Mark Linsky At Home Realty, Inc.

  321 Hammond Pond Pkwy Unit 301, Chestnut Hill, MA 02467
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  /15

  $6,600,000

  • 4 Beds
  • 6 Baths
  • 4,720 Sq Ft

  15 W Cedar St, Boston, MA 02108

  This prestigious residence boasts almost 5k sq ft of meticulously designed living space, offering an exquisite blend of classic charm and modern sophistication.Upon entering, you are greeted by an inviting ambiance that flows seamlessly throughout the home. The formal dining room sets the stage for memorable gatherings, while the spacious living areas provide a perfect canvas for relaxation and

  Aranson Maguire Group Compass

  15 W Cedar St, Boston, MA 02108
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  /31

  $6,800,000

  • 6 Beds
  • 3.5 Baths
  • 5,605 Sq Ft

  48 Hubbard Park Rd, Cambridge, MA 02138

  Sited far back from Brattle Street on nearly 1/2 an acre of landscaped grounds, this grandly scaled residence was constructed during the Gilded Age and later enhanced in the 1950s by a sharp mid-century modern addition. The expansive first floor is ideal for indoor/outdoor entertaining, enveloped by a curved wraparound porch surveying the back gardens. On the 2nd floor, the tranquil primary suite

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

  48 Hubbard Park Rd, Cambridge, MA 02138
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  /42

  $864,900

  • 3 Beds
  • 1.5 Baths
  • 1,489 Sq Ft

  159 Washington St Unit 4, Newton, MA 02458

  Entire Top Floor 3-Bed 1.5-Bath Newton Condo in Victorian-style building. Step into a charming, sunny, spacious living room with large vaulted ceilings, a fireplace, + custom window seating surrounded by 5 south-facing windows. 1/2 bath conveniently located between Living Area and the Breathtaking High-end Chef's Kitchen, ft.: Sub-Zero Refrigerator, 6-burner Wolf Gas Range, Custom-built

  Caio Simao Prestige Property Solutions, Inc.

  159 Washington St Unit 4, Newton, MA 02458
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  /26

  $1,100,000

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  61 Prince St Unit 1C, Boston, MA 02113

  Experience luxurious urban living in the heart of Boston’s historic North End. This modern 2+ bedroom, 2-bathroom residence offers over 1,400 square feet of well-designed living space, perfect for multiple uses and wonderful for entertaining. With generously sized bedrooms and flexible spaces, there's room for a home office, gym, or playroom to suit your needs. High ceilings, an open layout and

  Rebecca Marston Marston Beacon Hill, Inc.

  61 Prince St Unit 1C, Boston, MA 02113
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  /22

  $528,000

  • 2 Beds
  • 1 Bath
  • 782 Sq Ft

  8 Kinross Rd Unit 2, Brighton, MA 02135

  Delightful and rarely available two-bedroom condominium on a quiet one-way street in the heart of Cleveland Circle near the Brookline line. Beautifully refreshed with extensive interior painting, refinished kitchen cabinets, new lighting, and an updated bathroom with refinished tile and new mirror. Bright and spacious with high ceilings, big windows, and beautiful hardwood floors throughout. The

  Batya & Alex Team William Raveis R.E. & Home Services

  8 Kinross Rd Unit 2, Brighton, MA 02135
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  /22

  $769,000

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

  4 Crossman St Unit 4, Boston, MA 02126

  Experience modern living at its finest in this stunning 4-bedroom, 3-bath townhouse at 4 Crossman St, Boston, MA. Built in 2020, this spacious 2,430 sq. ft. home offers a sleek, contemporary design with high-end finishes throughout. The open-concept layout features a custom chef’s kitchen with stylish quartz countertops, perfect for entertaining and everyday living. Enjoy the luxury of three

  Jignesh Bhakta Baystate/Sunstate Realty

  4 Crossman St Unit 4, Boston, MA 02126
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  /35

  $5,995,000

  • 3 Beds
  • 3.5 Baths
  • 2,974 Sq Ft

  5 Joy St Unit 1, Boston, MA 02108

  Behind a discreet Beacon Hill façade lies one of the neighborhood’s most extraordinary private gardens, over 1,750 square feet of lush, professionally landscaped outdoor space, designed for both quiet retreat and grand entertaining. Home to the Appalachian Mountain Club for nearly a century, the property underwent a full renovation in 2019, restored to its residential roots and reimagined with

  Georgia Balafas Corcoran Property Advisors

  5 Joy St Unit 1, Boston, MA 02108
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  /18

  $1,399,000

  • 4 Beds
  • 1.5 Baths
  • 2,467 Sq Ft

  1 Washington Place, Boston, MA 02129

  Unlock the potential of a truly special offering in one of Boston’s most treasured neighborhoods—Charlestown’s iconic Gas Light District. Rarely available free-standing single-family house with potential for 3-unit conversion. This once-in-a-generation opportunity invites developers, builders, and investors to reimagine a long-loved home on a large, flat 4,296 sq/ft lot. Zoned 3F per the BBD;

  Nancy Pallotta Gibson Sotheby's International Realty

  1 Washington Place, Boston, MA 02129
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  /27

  $2,695,000

  • 2 Beds
  • 2.5 Baths
  • 1,825 Sq Ft

  76 Wareham St Unit 5D, Boston, MA 02118

  Experience dramatic Back Bay skyline views, sun-filled interiors, and modern luxury finishes at The Factory, a boutique building in SoWa’s Arts & Design District. Unit 5D is one of the largest floor plans, offering 2 bedrooms plus an oversized 3rd bedroom/den/home office and 2.5 baths. The open layout, wrapped in glass and steel, features a family room with double-sided fireplace, separate dining

  Joseph DeAngelo Coldwell Banker Realty - Boston

  76 Wareham St Unit 5D, Boston, MA 02118
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  /21

  $3,395,000

  • 3 Beds
  • 3 Baths
  • 2,370 Sq Ft

  251 Shawmut Ave Unit 2, Boston, MA 02118

  Exceptional South End corner penthouse with a wall of sunny west-facing windows & an incredible private roof deck. This three-bedroom plus office, three-bath home sits in the coveted Eight Streets neighborhood & blends timeless charm with modern luxury. Originally built by Kennedy Design Build & recently professionally re-designed, the unit spans two bright, spacious floors with seamless flow for

  Kopman Adler Team Compass

  251 Shawmut Ave Unit 2, Boston, MA 02118
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  /16

  $540,000

  • 2 Beds
  • 1.5 Baths
  • 782 Sq Ft

  15 N Beacon St Unit 328, Boston, MA 02134

  Discover the perfect blend of comfort and city living in this beautiful 2-bedroom, 1.5-bath condo in the heart of Allston. This home welcomes you with an airy, open layout filled with natural light and newly installed vinyl floors. The updated kitchen is a chef’s dream, featuring granite countertops, stainless steel appliances, and plenty of storage. Both bedrooms are spacious and thoughtfully

  Mike McKay Concept Properties

  15 N Beacon St Unit 328, Boston, MA 02134
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  /2

  $8,888,888

  • Land
  • 0.42 Acre
  • $21,164,019 per Acre

  1 Highgate St, Allston, MA 02134

  NEWMARK HAS BEEN EXCLUSIVELY RETAINED TO MARKET 1 HIGHGATE STREET, A 82-UNIT CLASS A APARTMENT/MIXED USE DEVELOPMENT. COMPLEMENTED BY 6,250 SQUARE FEET OF PRIME RETAIL COMMERCIAL SPACE IN THE RAPIDLY EXPANDING ALLSTON NEIGHBORHOOD OF BOSTON. INQUIRE FOR MORE INFORMATION.

  Casey Valente Newmark Grubb Knight Frank

  1 Highgate St, Allston, MA 02134
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  $719,900 New Construction

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft

  Unit 4 Plan at 421 Saratoga, East Boston, MA 02149

  Kinvarra Capital Builder

  421 Saratoga St Unit 38788771, East Boston, MA 02149
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  /24

  $587,000

  • 2 Beds
  • 1 Bath
  • 908 Sq Ft

  3 Kenney St Unit 2, Jamaica Plain, MA 02130

  Set in the vibrant Hyde Square neighborhood of Jamaica Plain, this warm and welcoming 2+ bedroom residence offers a comfortable layout and tranquil atmosphere. The flexible bonus room makes for a great home office, guest room or creative space. The eat-in kitchen delivers stainless steel appliances, granite countertops, and modern functionality, while the bathroom—thoughtfully renovated in

  Matthew Slowik Compass

  3 Kenney St Unit 2, Jamaica Plain, MA 02130
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  /14

  $543,400

  • 1 Bed
  • 1 Bath
  • 860 Sq Ft

  77 Pond Ave Unit 1103, Brookline, MA 02445

  Welcome to The Brook House! This bright and spacious one-bedroom, one-bath residence offers incredible potential for customization. Perched on the 11th floor, the unit features a balcony with sweeping city and treetop views! The open living and dining area is filled with natural light through large sliding glass doors, while the bedroom provides generous closet space. Though the unit would

  Joyce Crowe Crowe Properties

  77 Pond Ave Unit 1103, Brookline, MA 02445
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  /38

  $3,699,000

  • 4 Beds
  • 4.5 Baths
  • 3,700 Sq Ft

  216 Aspinwall Ave, Brookline, MA 02446

  Complete renovation to the studs of a distinctive Carriage House in a prime Brookline location that offers the perfect blend of urban and suburban living. This 4-bedroom, 4.5-bath home spans three floors and features a first-floor guest suite, an open layout ideal for entertaining, Designer kitchen with a stunning quartz island & Thermador appliances. The elegant, fireplaced family room opens to

  Leslie Zelada Grover Group Realty LLC

  216 Aspinwall Ave, Brookline, MA 02446
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  /31

  $9,500,000

  • 40 Beds
  • 26 Baths
  • 26,000 Sq Ft

  400-412 Neponset Ave, Boston, MA 02122

  proud to present 400-412 Neponset Avenue and 10-12 Redfield Street - a rare chance to acquire three adjacent properties totaling 26,000 SF in Dorchester’s Neponset/Port Norfolk neighborhood. The portfolio includes a corner mixed-use building and two triple-deckers with six spacious 3-bed units. Nearly 75% of the residential units have been recently renovated, providing strong in-place income with

  John Maggio

  400-412 Neponset Ave, Boston, MA 02122
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  /30

  $1,975,000

  • 2 Beds
  • 2.5 Baths
  • 1,571 Sq Ft

  40 Traveler St Unit 710, Boston, MA 02118

  Discover refined city living in this sophisticated 2-bed plus den, 2.5-bath home with TWO garage spaces at Siena Condominiums in Boston’s South End. Unit 710 offers 1,571 sq ft of beautifully designed space, featuring expansive floor-to-ceiling windows and two private balconies with sweeping city views. The spacious living area seamlessly flows into a chef-inspired kitchen, equipped with quartz

  Eric Dellovo Campion & Company Fine Homes Real Estate

  40 Traveler St Unit 710, Boston, MA 02118
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  /41

  $1,895,000

  • 4 Beds
  • 4.5 Baths
  • 4,469 Sq Ft

  172 Westminster Ave Unit 1, Watertown, MA 02472

  Discover this stunning, architecturally unique townhouse, blending luxury and functionality. The first floor features a gourmet kitchen with custom cabinetry, a large quartz island, w/Thermador high-end appliances, including a 6-burner stove and wine cooler, The spacious living room boasts a fireplace set in an Italian porcelain tile wall. Rich 5-inch oak floors run throughout, complemented by a

  Mike DelRose Coldwell Banker Realty - Belmont

  172 Westminster Ave Unit 1, Watertown, MA 02472
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  /18

  $649,000 Open Sun 10:30AM - 12PM

  • 4 Beds
  • 2 Baths
  • 1,704 Sq Ft

  40 Linden St Unit C, Dorchester, MA 02122

  Welcome to 40 Linden Street Unit C — a rare opportunity to own a spacious, thoughtfully updated four-bedroom home in the city. With over 1,700 SqFt of living area, multiple outdoor retreats, and convenient access to public transit, beaches, parks, and downtown, this property provides exceptional value and versatility. The open-concept main level features a bright living area and eat-in kitchen,

  Danielle Dimond Senne

  40 Linden St Unit C, Dorchester, MA 02122

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