2,619

Homes for Sale near Winsor School

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  • /14

    $699,000

    • 4 Beds
    • 1.5 Baths
    • 1,453 Sq Ft

    14 Temple St Unit 14, Boston, MA 02114

    This is the one you’ve been waiting for! Sun-filled 4 bedroom townhome with private outdoor space, and garage parking, it’s a true city oasis. Conveniently located in Lower Mills, the neighborhood boasts great restaurants, shops, Neponset Riverwalk, public transportation and easy highway access. This end unit, tri-level home features an open living/dining area, crisp white kitchen with stainless

    Julie Holenport Coldwell Banker Realty - Boston

    14 Temple St Unit 14, Boston, MA 02114
  • /39

    $1,395,000

    • 5 Beds
    • 3 Baths
    • 2,948 Sq Ft

    278 Cabot St, Newtonville, MA 02460

    Outstanding investment opportunity in a very convenient Newton location! This updated 2-family features two 2 bedroom-1 bath apartments + an in-law apartment in the attic. Both units feature classic layouts with a spacious living room, formal dining room, & a large kitchen. The attic has 1 bedroom, a good sized living room, and a kitchen+full bath. The property has separately metered gas boilers

    Jackson Wells Harvard Real Estate

    278 Cabot St, Newtonville, MA 02460
  • /31

    $1,030,000

    • 6 Beds
    • 3 Baths
    • 3,972 Sq Ft

    36 Brookford St, Dorchester, MA 02125

    Calling all house hackers and owner-occupants!!! Now's the time to get into this turn-key home and start building equity and cash flow. There is very little available in this price range and condition. Unit #1 (now vacant) is a 1 bedroom with a great rental history with updates made consistently throughout the years. Unit #2 has 2 bedrooms, a separate living room & eat-in kitchen. The most

    David Cahill Century 21 Cityside

    36 Brookford St, Dorchester, MA 02125
  • /42

    $2,999,999

    • 6 Beds
    • 4.5 Baths
    • 3,796 Sq Ft

    24 Central St, Somerville, MA 02143

    Houses like this do not come to market often! Former Woosley style mansion converted into 3 extremely perfect sized units. The master unit has 4 bedrooms, 3 fireplaces, an eat-in kitchen, dining room and living room with fireplace nook. Full of fine woodworking detail this house was built in 1895 and has the craftsmanship you only find from that era. There are three private outdoor spaces and a

    William Hartford Redfin Corp.

    24 Central St, Somerville, MA 02143
  • /24

    $519,000

    • 2 Beds
    • 1 Bath
    • 885 Sq Ft

    574 Ashmont St Unit 1, Dorchester, MA 02122

    Conveniently located in the desirable Neponset neighborhood, this delightful condo provides quick access to all the local amenities you could hope for! The tranquil main bedroom is tucked away for privacy and boasts a large closet. The second bedroom also has a large walk-in closet – perfect for home office or guest room. Airy living room-dining room combo is perfect for entertaining. Enjoy

    Tara O'Riordan Coldwell Banker Realty - Dorchester

    574 Ashmont St Unit 1, Dorchester, MA 02122
  • /34

    $995,000 Open Sun 12PM - 2PM

    • 6 Beds
    • 3 Baths
    • 4,291 Sq Ft

    151 Blue Hill Ave, Roxbury, MA 02119

    Step into this tastefully renovated grandeur of this massive Victorian brimming with architectual details. Nestled on an oversized lot this gem offers 4291 SF of living space. Upon entering this 6 BR 3 bath home you are greeted by french doors that open to a spacious hallway. To the right, a lovely parlor w/ fireplace awaits. To the left you will find a versatile room perfect for a family room

    David White OwnerEntry.com

    151 Blue Hill Ave, Roxbury, MA 02119
  • /19

    $699,000

    • 2 Beds
    • 1 Bath
    • 790 Sq Ft

    45 1st Ave Unit 301, Boston, MA 02129

    Corner 2 bed/1 bath at the coveted Starboard! This most desirable unit provides an idyllic floorplan with 9' ceilings, oversized windows, and great natural light. Large and dimensional living space is the ideal space to relax or entertain. Generous kitchen with oversized cabinetry, gas cooking, center island, and dedicated dining area. Primary bedroom features space for a king-size and custom

    Adam Geragosian Compass

    45 1st Ave Unit 301, Boston, MA 02129
  • /24

    $1,500,000

    • 3 Beds
    • 4 Baths
    • 2,400 Sq Ft

    17 Atlantic St, Boston, MA 02127

    Stunning Victorian single family perched upon the top of a quiet Thomas Park side street. As you enter you are greeted with an open concept living and kitchen space, complete with custom built-ins surrounding the gas fireplace making this level the perfect space to entertain or enjoy quiet nights at home. A half bath and large deck off of the rear round out the main level. The 2nd floor boasts a

    Aranson Maguire Group Compass

    17 Atlantic St, Boston, MA 02127
  • /24

    $589,000

    • 1 Bed
    • 1 Bath
    • 723 Sq Ft

    42 8th St Unit 2312, Boston, MA 02129

    Inquire about potential 5.25% 30-year fixed financing! Experience elevated city living at Parris Landing, nestled in the historic Charlestown Navy Yard. This beautifully designed bi-level 1-bedroom, 1-bathroom home offers modern comfort, complete with valet parking in a lively, pet-friendly community. Ideally located in the main building, the home features a contemporary custom kitchen with

    Burbs To Boston Compass

    42 8th St Unit 2312, Boston, MA 02129
  • /21

    $3,300,000

    • 17 Beds
    • 6 Baths
    • 6,576 Sq Ft

    65 Brookline St, Cambridge, MA 02139

    Rare offering of this 6 Unit Investment property located in desirable Cambridgeport location. 65 Brookline Street is a three story building that contains a total of 6 units comprised of five 3 bedroom/1 bath units and one 2 bedroom/1 bath unit. Many recent updates to some units including new upgraded kitchen cabinets, stone counters, SS appliances and in-unit washer/dryers. Each unit is

    Brendan Noonan III C. Brendan Noonan & Co.

    65 Brookline St, Cambridge, MA 02139
  • /30

    $2,600,000

    • 4 Beds
    • 2.5 Baths
    • 2,956 Sq Ft

    100 Summit Ave, Brookline, MA 02446

    WELCOME TO THE NEW 100 SUMMIT!! Atop Corey Hill, this spacious urban residential home with four bedrooms, 2.5 baths is set back from the street with many upgrades including an updated kitchen and a newer master bath renovation, Central air, refinished hardwood floors, crown molding, and a recently constructed two-car garage with storage plus ample driveway. Large eat-in kitchen with attached

    Bob Ley Coldwell Banker Realty - Brookline

    100 Summit Ave, Brookline, MA 02446
  • /10

    $1,155,000

    • 9 Beds
    • 3 Baths
    • 2,600 Sq Ft

    5 Sutton St, Mattapan, MA 02126

    PACKAGE DEAL! 3 condo units in a 6 unit Mattapan building available now & being delivered vacant. Each unit features 3 beds 1 bath & are identical units. There is one unit on each floor being sold. Perfect opportunity to acquire this 3 unit package deal & cash flow in a bustling market. With annual gross rent potential upwards of $122K this makes for a great acquisition hold or your perfect

    Markese Daise Stony Brook & Lennox Realty Advisors

    5 Sutton St, Mattapan, MA 02126
  • /25

    $1,049,900

    • 2 Beds
    • 2 Baths
    • 1,106 Sq Ft

    20 Second St Unit 222, Cambridge, MA 02141

    Experience modern urban living in this 2-bed, 2-bath condo at One First, East Cambridge. This well maintained unit, from the original owner, offers convenient city living. Enjoy 24-hour concierge, a resident library, fitness center, and a common roof deck with city views. This quiet, interior-facing unit boasts Brazilian cherry flooring, an open concept, and high ceilings. Both bathrooms are

    Kevin Cleary RE/MAX Select Realty

    20 Second St Unit 222, Cambridge, MA 02141
  • /33

    $829,000

    • 2 Beds
    • 1.5 Baths
    • 1,088 Sq Ft

    533 Cambridge St Unit 309, Allston, MA 02134

    Rarely available duplex penthouse in vibrant Allston! This stunning home features an exclusive private roof deck with breathtaking panoramic views of the Boston skyline—perfect for relaxing or entertaining. Two garage parking spaces included. Inside, enjoy a spacious layout with generously sized bedrooms, central AC, and modern comforts throughout. Located in an elevator building for added

    Ryan Wilson Keller Williams Realty

    533 Cambridge St Unit 309, Allston, MA 02134
  • /19

    $1,099,000

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

    180 Telford St Unit 614, Boston, MA 02135

    This Sun-Bathed, South-Facing corner Penthouse 2BR/2BA features wood floors, an open kitchen with quartz counters, custom cabinets, and stainless-steel appliances. Floor-to-ceiling windows showcase spectacular sunsets and Charles River views. The primary suite unfolds through a custom oversized closet to an en-suite bathroom with a double vanity. A bright second bedroom sits beside its own full

    Frank Celeste Gibson Sotheby's International Realty

    180 Telford St Unit 614, Boston, MA 02135
  • /42

    $985,000

    • 6 Beds
    • 2 Baths
    • 1,938 Sq Ft

    24 Parker St Unit 24, Arlington, MA 02474

    Perfectly situated in the heart of vibrant East Arlington this thoughtfully updated, two-story condo unit offers an abundance of space and versatility in a family-friendly community only steps from shopping, dining, the Minuteman Bike Path, Spy Pond, public transportation, Hardy ES, bus routes, 3 playgrounds, and a 10-minute walk to Alewife Station. As an added bonus, the home is deleaded with a

    Danielle Fleming MA Properties

    24 Parker St Unit 24, Arlington, MA 02474
  • /30

    $1,699,000

    • 4 Beds
    • 3.5 Baths
    • 2,235 Sq Ft

    14 Essex St, Charlestown, MA 02129

    This sunny, 4+BR/3.5BA, 2235sf, SF home is located on a quaint gas-lit street near town center and features an open layout and recent renovation. A spacious living room, with tall ceilings, plantation shutters, and gas FP flows to an elegant dining area - perfect for entertaining. The chef’s kitchen features Thomasville cabinetry, granite countertops, tiled backsplash, stainless appliances,

    Nancy Roth Gibson Sotheby's International Realty

    14 Essex St, Charlestown, MA 02129
  • /17

    $3,100,000

    • 9 Beds
    • 4 Baths
    • 3,421 Sq Ft

    179 Massachusetts Ave, Boston, MA 02115

    Package sale of two condo units in a boutique building just steps from Berklee College of Music. The residential unit 2 (2nd floor) is leased through 8/31/2025 at $6,500/month and features approximately 1,695 sq ft with 5 bedrooms, 2 full bathrooms, and a spacious open-concept kitchen. Unit 3 is leased through 8/31/2025 at $7,500/month and offers approximately 1,726 sq ft with 4 bedrooms and 2

    KoKo Kwan Kwan Realty Inc.

    179 Massachusetts Ave, Boston, MA 02115
  • /37

    $2,998,000

    • 4 Beds
    • 4.5 Baths
    • 3,419 Sq Ft

    131 Charles St, Cambridge, MA 02141

    Stunning Contemporary home with a Detached Carriage House! Discover your dream home in this newly built, modern townhouse with a unique below-grade connection to a separate modern carriage house. This exceptional property offers 4 Spacious Bedrooms w/ ample natural light & modern finishes. Impressive top fl prime suite w/ en suite bath, wic, & deck. 4.5 luxurious bathrooms. Lower level has 2nd

    Ann Hogstadius RE/MAX Real Estate Center

    131 Charles St, Cambridge, MA 02141
  • /18

    $1,049,000

    • 4 Beds
    • 2.5 Baths
    • 1,795 Sq Ft

    110 Reed St, Cambridge, MA 02140

    Prime location! This carefully detailed two-family home presents a rare opportunity to enjoy spacious living within the preferred Cambridge/Davis Square neighborhood. Originally built as a single-family residence, this home offers many options across two levels of living on a favored street. Natural light generously pours through the windows of this sun-filled home. The property is convenient to

    Christopher Griffin Griffin Properties, Inc.

    110 Reed St, Cambridge, MA 02140
  • /34

    $699,500

    • 3 Beds
    • 1 Bath
    • 1,542 Sq Ft

    18 Dighton St Unit 20, Brighton, MA 02135

    Brighton Center – Spacious Condo with Parking & Expansion Potential Just steps from Brighton Center. This upper-level condo in a stately two-family offers 3 bedrooms, a 3-season porch, and over 1,500 sq. ft. of sun-filled living space. Features include high ceilings, bay windows, hardwood floors throughout (including kitchen), and in-unit laundry. Deeded attic offers great potential for future

    Norman O'Grady RE/MAX On the Charles

    18 Dighton St Unit 20, Brighton, MA 02135
  • /30

    $2,495,000

    • 4 Beds
    • 3.5 Baths
    • 3,247 Sq Ft

    89 Oliver Rd, Belmont, MA 02478

    Breathtaking views of Little Pond grace this rare waterfront 10 room retreat, with 3 levels of thoughtfully designed living space, it is a rare opportunity to live on the water’s edge. The 1st level features a spacious living room with gas fireplace and built-ins which flows into the dining room with slider opening to an expansive deck and sweeping views, a well-equipped gleaming kitchen and

    Barbara Nolan Coldwell Banker Realty - Belmont

    89 Oliver Rd, Belmont, MA 02478
  • /40

    $949,999

    • 2 Beds
    • 2.5 Baths
    • 2,201 Sq Ft

    583 Baker St Unit 583, Boston, MA 02132

    Welcome to this stunning 2-bedroom, 2.5-bathroom condo, built in 2020 and thoughtfully designed for comfort and style. Located in desirable West Roxbury, this home offers a perfect blend of modern amenities and timeless charm.Step inside to discover gleaming hardwood floors that flow throughout the open-concept living space. The spacious kitchen is a chef’s dream, featuring ample cabinet storage

    Andrew Casserly South End Realty Group

    583 Baker St Unit 583, Boston, MA 02132
  • /19

    $1,395,000

    • 2 Beds
    • 1.5 Baths
    • 936 Sq Ft

    1395 Washington St Unit PH2, Boston, MA 02118

    Introducing The EL, a collection of 33 new construction residences in the Union Park neighborhood of Boston’s dynamic South End!! 2 bed, 1 bed & studio homes w/one floor living & elevator access are defined by urban elegance & historic soul. The latest creation by award winning team of Boston developer Peter Georgantas, EMBARC architecture & Markel Interiors. South facing PH2 is sun-splashed and

    The Biega + Kilgore Team Compass

    1395 Washington St Unit PH2, Boston, MA 02118
  • /30

    $999,000

    • 5 Beds
    • 2.5 Baths
    • 3,179 Sq Ft

    23 Gordon St, Allston, MA 02134

    Welcome to 23 Gordon, where classic charm meets modern convenience in this stunning 5-bedroom, 2.5-bathroom residence. Step inside to a spacious layout, enhanced by high ceilings that create an airy, welcoming atmosphere. The modern kitchen boasts sleek stainless steel appliances and a breakfast bar, flowing into an inviting dining room ideal for hosting guests. Unwind in the light-filled living

    Matt Gorman EDGE Realty Advisors

    23 Gordon St, Allston, MA 02134
  • /18

    $565,000

    • 1 Bed
    • 1 Bath
    • 585 Sq Ft

    11 Cogswell Ave Unit 16, Cambridge, MA 02140

    Discover this exceptionally located condo, offering easy access to Davis and Porter Squares, the Red Line T, and a vibrant array of restaurants and shops. Inside, you'll find an excellent floor plan with a modern kitchen featuring stainless steel appliances and a completely renovated bathroom with modern finishes. Beyond these, the condo boasts beautiful hardwood flooring throughout, fresh wall

    Aditi Jain Redfin Corp.

    11 Cogswell Ave Unit 16, Cambridge, MA 02140
  • /9

    $415,000

    • 1 Bed
    • 1 Bath
    • 570 Sq Ft

    1691 Commonwealth Ave Unit 32, Brighton, MA 02135

    Top-floor condo at 1691 Commonwealth Ave in Brighton, featuring sweeping city views, tons of natural light, and beautiful hardwood floors throughout. Ideally located with the Sutherland Rd. Green Line MBTA stop right across the street for easy access to downtown Boston, Beacon Hill, and Back Bay. Less than half a mile from Boston College and convenient to Boston University, Harvard, and

    Michael Eustace NextGen Realty, Inc.

    1691 Commonwealth Ave Unit 32, Brighton, MA 02135
  • /18

    $429,000

    • 3 Beds
    • 1.5 Baths
    • 984 Sq Ft

    32 Saint Marks Rd Unit 1, Dorchester Center, MA 02124

    Set on a quiet, tree-lined street in Dorchester’s historic St. Marks neighborhood, this 3-bedroom, 1.5-bath condo delivers the space, function, and location that make everyday living seamless. The layout offers a smooth flow, from a fireplaced living room and dining area to a granite kitchen with plenty of counter space making it easy to cook & connect. Two of the bedrooms are generously sized,

    Erika Tarlow Coldwell Banker Realty - Boston

    32 Saint Marks Rd Unit 1, Dorchester Center, MA 02124
  • /14

    $565,000

    • 1 Bed
    • 1 Bath
    • 406 Sq Ft

    227 Marlborough St Unit 4, Boston, MA 02116

    Location! Style! Character! Beautifully updated first-floor studio on one of the most sought-after streets in the Back Bay checks all the boxes! Classic turn-of-the-century curb appeal w/a cobble-stone sidewalk and lovely wrought iron fenced gardens, setting the stage for entry to the impressive grand foyer of this impeccably kept building. The unit makes exceptional use of space, its 11’+

    The Gillach Group William Raveis R. E. & Home Services

    227 Marlborough St Unit 4, Boston, MA 02116
  • /25

    $795,000

    • 1 Bed
    • 1 Bath
    • 748 Sq Ft

    150 Cambridge St Unit A403, Cambridge, MA 02141

    Welcome to One First – a highly desirable, full-service concierge building in an unbeatable Cambridge location. Enjoy unparalleled convenience with easy access to the Charles River, North End, Beacon Hill, Mass General Hospital, Kendall Square, and just steps to the Lechmere T station. This beautifully maintained unit features soaring ceilings, oversized windows that flood the space with natural

    Ryan Wilson Keller Williams Realty

    150 Cambridge St Unit A403, Cambridge, MA 02141
  • /33

    $637,000

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft

    115 Highland Ave Unit 11, Somerville, MA 02143

    !!1 Prime Location !!!. This beautifully renovated, largest 2-bedroom unit in the complex, with one full bathroom, offers the perfect blend of modern design and functional space. The expansive open-concept living area (approximately 32' x 25') provides an abundance of room for both relaxation and entertainment. A custom-built kitchen features exquisite millwork with sleek stone countertops.

    Zahra Zoglauer Berkshire Hathaway HomeServices Commonwealth Real Estate

    115 Highland Ave Unit 11, Somerville, MA 02143
  • /38

    $1,599,999

    • 2 Beds
    • 2.5 Baths
    • 1,511 Sq Ft

    1 Charles St S Unit 604, Boston, MA 02116

    Located on the 6th floor of Boston’s coveted One Charles, Unit 604 is a modern 2 bed, 2.5 bath residence with a spacious, open-concept layout designed for contemporary living. This sunlit home has been lovingly maintained by a single family for 20 years and is now ready for its next owner. A desirable split-bedroom floor plan places bedrooms on opposite sides of the home for maximum privacy,

    ONecia Simpson Advisors Living - Boston

    1 Charles St S Unit 604, Boston, MA 02116
  • /37

    $1,039,000

    • 4 Beds
    • 3 Baths
    • 2,142 Sq Ft

    172 Orchard St, Watertown, MA 02472

    Don’t miss this rare opportunity to own a move-in-ready luxury home in one of Watertown’s most sought-after communities. No detail has been overlooked in this perfect blend of upscale living and everyday comfort. The main level features a bright, open-concept layout with a designer kitchen, stainless steel appliances, quartz countertops, and stylish cabinetry flowing into the dining and living

    Eric Walbridge Gibson Sotheby's International Realty

    172 Orchard St, Watertown, MA 02472
  • /16

    $490,000

    • 1 Bed
    • 1 Bath
    • 420 Sq Ft

    26 Unity St Unit 2, Boston, MA 02113

    Live in the heart of Boston’s historic North End! This charming parlor-level 1 bed, 1 bath condo is perfectly situated on picturesque Unity Street—steps from the Old North Church and the Prado. Inside, an open-concept kitchen and living area offers a warm, inviting space for entertaining. The bedroom is nicely sized and has a generous closet with overhead storage. Recently renovated bath! The

    Ron Ventresca Greater Metropolitan R. E.

    26 Unity St Unit 2, Boston, MA 02113
  • /16

    $699,000

    • 2 Beds
    • 1 Bath
    • 640 Sq Ft

    81 E Brookline St Unit 3, Boston, MA 02118

    Stunning 2-bed, 1-bath condo in a classic South End brownstone blends historic charm with modern updates. Just one flight up, this light-filled upper-level unit features soaring ceilings, exposed brick, restored original floors, and a spacious open layout. Renovated throughout with a sleek new kitchen, stainless steel appliances, spa-like bath, and leveled flooring. The large primary bedroom

    Steven Cohen Team Keller Williams Realty Boston-Metro | Back Bay

    81 E Brookline St Unit 3, Boston, MA 02118
  • /16

    $779,000

    • 3 Beds
    • 2.5 Baths
    • 2,054 Sq Ft

    857 Adams St Unit 857, Boston, MA 02124

    Welcome to this 11-year-young Cedar Grove townhome. Lovingly maintained by the original owner, the home features updated gleaming hardwood floors (2024) and a sunny, open-concept main level. The kitchen offers new appliances and new granite countertops flowing into a dining area. Downstairs, enjoy a fully finished basement with walk-out bulkhead. The second floor has two spacious bedrooms with

    Marcia Riddick William Raveis R.E. & Home Services

    857 Adams St Unit 857, Boston, MA 02124
  • /22

    $1,099,000

    • 3 Beds
    • 2 Baths
    • 1,398 Sq Ft

    1948 Washington St Unit 3E, Boston, MA 02118

    Built in 2020, this stylish and spacious condo feels like new and offers nearly 1,400 square feet of flexible living space. With 3 bedrooms (or 2 plus an office) this home features 2 full bathrooms, including a luxurious en-suite in the primary bedroom, complete with a walk-in closet and private deck. Enjoy an open-concept layout with high-end finishes throughout, including Fisher & Paykel

    Scott Nelson Coldwell Banker Realty - Westwood

    1948 Washington St Unit 3E, Boston, MA 02118
  • /26

    $580,000

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft

    95 Child St Unit 2, Jamaica Plain, MA 02130

    Charming second floor, 2 bed condo in central JP is full of style and natural light. Lovely front living room has bay windows, decorative mantle & ornamental trim. Tucked away off the living space is a unique Victorian turret room with curved windows, creating an ideal dining nook or home office retreat. The sleek, white bathroom was refreshed in ’21, showcasing subway tile, rainfall shower head

    Christian Iantosca Team Arborview Realty Inc.

    95 Child St Unit 2, Jamaica Plain, MA 02130
  • /29

    $650,000 Open Wed 5:30PM - 7:30PM

    • 2 Beds
    • 2 Baths
    • 907 Sq Ft

    301 Border St Unit 409, Boston, MA 02128

    NO CONDO FEES 1ST YEAR! Rare opportunity to own a one-of-a-kind 2 bed, 2 bath corner residence at MIRA with beautiful water views! This thoughtfully designed new construction home features an open-concept layout flooded with natural light from oversized windows—perfect for both everyday living and entertaining.Enjoy stylish finishes throughout, including Metropolitan cabinetry, quartz

    Charlesgate New Development Team Charlesgate Realty Group, llc

    301 Border St Unit 409, Boston, MA 02128
  • /21

    $619,000 Open Thu 6:30PM - 7:30PM

    • 2 Beds
    • 1.5 Baths
    • 1,283 Sq Ft

    602 Canterbury St Unit 14, Roslindale, MA 02131

    Welcome to The Canterbury, a collection of 14 new construction townhomes built with modern style, nestled in Roslindale! The Canterbury offers the perfect blend of contemporary elegance and exceptional functionality. Each home features 2 bedrooms and 1.5 bathrooms with open-concept layouts, oversized windows for abundant natural light, and stylish finishes throughout. The modern kitchens boast

    Charlesgate New Development Team Charlesgate Realty Group, llc

    602 Canterbury St Unit 14, Roslindale, MA 02131

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