Cleveland Circle Homes

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  /15

  $635,000

  $14K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft

  21 Englewood Ave Unit 2, Brookline, MA 02445

  Don't miss this move-in ready 2-bedroom, 1-bath condo in one of Brookline's most convenient locations! This sun-filled home features an updated kitchen with granite countertops and stainless steel appliances, an open living and dining area ideal for everyday living and entertaining, two spacious bedrooms with ample closet space. Heat, hot water, and one assigned parking space are all included in

  

  Alina Wang

  Coldwell Banker Realty - Lexington

  21 Englewood Ave Unit 2, Brookline, MA 02445
• Explore Cleveland Circle

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  /11

  $3,050 Per Month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Apartment for Rent

  1871 Beacon St Unit 5, Brookline, MA 02445

  Renovated 2nd floor 1 bed/1 bath at the corner of Beacon St and Strathmore Rd in Brookline’s Cleveland Circle. Bright corner living room with oversized windows and excellent natural light throughout. Updated kitchen with granite countertops, stainless steel appliances, and ample cabinet space. Hardwood floors throughout and a well-proportioned layout with comfortable living and dining

  

  Adam Aroesty

  Hammond Residential Real Estate

  1871 Beacon St Unit 5, Brookline, MA 02445
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  /12

  $6,700,000

  Sold Jun 24, 2026

  278 Clinton Rd, Brookline, MA 02445

  • 5 Beds
  • 6.5 Baths
  • 6,658 Sq Ft
  • Built 2026

  Last Sold Summary

  • 4% Below List Price
  • $1,006/SF
  • 21 Days On Market

  Current Estimated Value $6,558,035

  Last Listing Agent Jayne Friedberg Coldwell Banker Realty - Brookline

  278 Clinton Rd, Brookline, MA 02445
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  /42

  Est $3,534,653

  Not Listed For Sale

  473 Chestnut Hill Ave, Brookline, MA 02445

  • 6 Beds
  • 4.5 Baths
  • 5,662 Sq Ft
  • Built 1926

  473 Chestnut Hill Ave, Brookline, MA 02445

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Eileen Kibrick O Grady Coldwell Banker Realty - Brookline
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  /15

  $545,000

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft

  1834 Beacon St Unit B1, Brookline, MA 02445

  Turnkey Investor Opportunity in Prime Brookline! Garden-level condo situated in a well-maintained brownstone between Washington Square and Cleveland Circle. Featuring high ceilings and hardwood flooring with spacious bedrooms, a full kitchen, and an inviting living area. Low condo fees include heat and water. Common laundry is on the same floor. Excellent commuting location with quick access to

  Olivia Tjie Redfin Corp.

  1834 Beacon St Unit B1, Brookline, MA 02445
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  /50

  Starting at $2,350 Plus Fees

  • 1 - 3 Beds

  1862-1870 Beacon St, Brookline, MA 02445

  Apartment complex on the Brookline/Brighton town line. Garbage disposal and dishwasher in kitchen. Right on Beacon St, steps to the green line C train. Short walk to Cleveland Circle and Washington Square. Historic and beautiful building with onsite maintenance and coin-op laundry. Tenant controlled temperature! Window AC included. 12 month lease required.

  Reservoir Court

  1862-1870 Beacon St, Brookline, MA 02445
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  /30

  $1,350,000

  Sold Apr 16, 2026

  37 Englewood Ave Unit 3, Brookline, MA 02445

  • 3 Beds
  • 3 Baths
  • 1,814 Sq Ft
  • Built 1930

  Last Sold Summary

  • 9% Above List Price
  • $744/SF
  • 10 Days On Market

  Current Estimated Value $1,313,912

  Last Listing Agent Shad Ghazarian Ghazarian Group LLC

  37 Englewood Ave Unit 3, Brookline, MA 02445
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  /42

  Est $2,499,652

  Not Listed For Sale

  92 Dean Rd, Brookline, MA 02445

  • 6 Beds
  • 3.5 Baths
  • 3,161 Sq Ft
  • Built 1913

  92 Dean Rd, Brookline, MA 02445

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Shahan Missaghian William Raveis R.E. & Home Services
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  /32

  $9,500,000

  • 7 Beds
  • 8 Baths
  • 9,500 Sq Ft

  355 Buckminster Rd, Brookline, MA 02445

  Magnificent estate on one of Brookline’s most beautiful residential streets, blending timeless architecture with modern luxury. Expansive first floor features elegant period details, grand entertaining rooms, an impressive foyer, custom chef’s kitchen, and spacious family room, with a covered porch and large deck extending the living space outdoors. The home offers a palatial primary suite with

  Samantha Stumpo Serhant

  355 Buckminster Rd, Brookline, MA 02445
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  /14

  $3,600 Per Month

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft
  • Apartment for Rent

  1871 Beacon St Unit 4, Brookline, MA 02445

  Spacious and sun-filled 3 bed / 1 bath ideally located on Beacon Street between Cleveland Circle and Englewood Ave. This classic Brookline apartment blends charm with modern updates, featuring hardwood floors, high ceilings, and excellent natural light throughout. Updated kitchen features full-size appliances and stone counters.Enjoy the convenience of in-building laundry and a prime location

  

  Adam Aroesty

  Hammond Residential Real Estate

  1871 Beacon St Unit 4, Brookline, MA 02445
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  /12

  $735,000

  Sold Dec 22, 2025

  8 Strathmore Rd Unit G, Brookline, MA 02445

  • 2 Beds
  • 2 Baths
  • 1,375 Sq Ft
  • Built 1900

  Last Sold Summary

  • 1% Below List Price
  • $535/SF
  • 7 Days On Market

  Current Estimated Value $783,719

  Last Listing Agent Joan Solomont Coldwell Banker Realty - Brookline

  8 Strathmore Rd Unit G, Brookline, MA 02445
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  /40

  Est $3,997,964

  Not Listed For Sale

  96 Dean Rd, Brookline, MA 02445

  • 6 Beds
  • 4.5 Baths
  • 5,106 Sq Ft
  • Built 1893

  96 Dean Rd, Brookline, MA 02445

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Tracy Campion Campion & Company Fine Homes Real Estate
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  /22

  $531,000

  $14K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft

  1 Lanark Rd Unit 7, Brookline, MA 02445

  This bright and updated corner residence offers the perfect blend of comfort, convenience, and location in the heart of Cleveland Circle. Thoughtfully laid out, this 2 bedroom home features an inviting living space filled with natural light, an updated kitchen, full-size windows, tile flooring throughout, and generous closet storage. Additional highlights include upgraded electrical, an off

  The Broadway Group Engel & Volkers Boston

  1 Lanark Rd Unit 7, Brookline, MA 02445
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  /21

  $4,500 - $5,500

  Total Monthly Price

  • 3 - 4 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Condo for Rent

  9 Strathmore Rd, Brookline, MA 02445

  4BR / 2BA in Washington Sq./Cleveland Circle — 1,400 sq ft, Private Balcony, Shared Roof Deck$5,200/month | Available Immediately or September 1, 2026 | No Broker FeeMiddle-floor unit in a well-maintained 4-unit building on Strathmore Road. Move-in ready. Serious space, great light, and one of the shortest walks to the C and D lines you'll find at this price.The unit — 1,400

  9 Strathmore Rd, Brookline, MA 02445
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  /16

  $735,000

  Sold Aug 29, 2025

  1856 Beacon St Unit 2D, Brookline, MA 02445

  • 2 Beds
  • 1.5 Baths
  • 913 Sq Ft
  • Built 1975

  Last Sold Summary

  • 5% Below List Price
  • $805/SF
  • 45 Days On Market

  Current Estimated Value $750,904

  Last Listing Agent Alexander Koziakov Compass

  1856 Beacon St Unit 2D, Brookline, MA 02445
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  /38

  Est $3,106,772

  Not Listed For Sale

  247 Fisher Ave, Brookline, MA 02445

  • 5 Beds
  • 3.5 Baths
  • 5,235 Sq Ft
  • Built 1900

  247 Fisher Ave, Brookline, MA 02445

  Last Sold Summary

  • 68 Days On Market

  Last Listing Agent Bell | Whitman Group Compass
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  /18

  $479,000

  $20K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 474 Sq Ft

  1880 Beacon St Unit 6, Brookline, MA 02445

  Beautifully renovated 1 bedroom in Brownstone. Fantastic Brookline location! Great layout with no wasted space! This condo has many nice features including a Stylish kitchen with quartz countertops and stainless steel appliances. The bathroom has lovely tile and a custom glass shower as well as a heated floor. Additional amenities include great closet space, a fireplace, air conditioning, and

  laura esdale Conway - West Roxbury

  1880 Beacon St Unit 6, Brookline, MA 02445
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  /33

  $5,500 Plus Fees

  • 4 Beds
  • 2 Baths
  • Condo for Rent

  1801 Beacon St Unit 6, Brookline, MA 02445

  1801 Beacon St. #6, Brookline, MA 02445Spacious 4-bedroom, 2-bath apartment available 9/1 in a prime Brookline location along Beacon Street. This professionally maintained unit features hardwood floors throughout, high ceilings, recessed lighting, and a bright, flexible layout ideal for graduate students or young professionals.The apartment offers a modern kitchen with dark

  1801 Beacon St Unit 6, Brookline, MA 02445
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  /15

  $670,000

  Sold Aug 04, 2026

  19 Englewood Ave Unit 2, Brookline, MA 02445

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft
  • Built 1945

  Last Sold Summary

  • 3% Below List Price
  • $846/SF
  • 16 Days On Market

  Current Estimated Value $664,660

  Last Listing Agent Batya & Alex Team William Raveis R.E. & Home Services

  19 Englewood Ave Unit 2, Brookline, MA 02445
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  /29

  Est $3,206,107

  Not Listed For Sale

  285 Clinton Rd, Brookline, MA 02445

  • 6 Beds
  • 3.5 Baths
  • 4,903 Sq Ft
  • Built 1901

  285 Clinton Rd, Brookline, MA 02445

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Bell | Whitman Group Compass
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  /33

  $1,295,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  23 Strathmore Rd Unit 3, Brookline, MA 02445

  Welcome to the best of Brookline brownstone living! This stunning 3 bed penthouse features newly refinished wood floors, kissed by maximum sun exposure and graced by outsized ceiling height. Original wood doors, trim mouldings and historic marble-ensconced fireplace add to the charm. A chef’s kitchen boasts modern 2-toned cabinetry, quartz countertops, tiled backsplash, stainless steel

  Common Ground Collective Team Compass

  23 Strathmore Rd Unit 3, Brookline, MA 02445
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  /35

  $5,150 Plus Fees

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft
  • Condo for Rent

  10 Strathmore Rd Unit 2, Brookline, MA 02445

  NO BROKERAGE FEE OR SECURITY DEPOSIT DUE!AVAILABLE SEPTEMBER 1, 2026!DONT MISS OUT ON THIS FANTASTIC DEAL IN THE HIGHLY DESIRABLE BRIGHTON/BROOKLINE LINE IN BETWEEN THE CLEVELAND CIRCLE AND WASHINGTON SQUARE NEIGHBORHOODS! THIS MASSIVE 4 BED 2 BATH HAS MUCH TO BE DESIRED! FEATURES INCLUDE:- LARGE BEDROOMS WITH TONS OF NATURAL SUNLIGHT- FULLY APPLIANCED EAT-IN-KITCHEN

  10 Strathmore Rd Unit 2, Brookline, MA 02445
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  /23

  $3,285,000

  Sold May 14, 2026

  43 Druce St, Brookline, MA 02445

  • 5 Beds
  • 4.5 Baths
  • 3,658 Sq Ft
  • Built 1900

  Last Sold Summary

  • 12% Below List Price
  • $898/SF
  • 62 Days On Market

  Current Estimated Value $3,335,530

  Last Listing Agent Jayne Friedberg Coldwell Banker Realty - Brookline

  43 Druce St, Brookline, MA 02445
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  /24

  Est $2,540,368

  Not Listed For Sale

  289 Clinton Rd, Brookline, MA 02445

  • 5 Beds
  • 3.5 Baths
  • 2,992 Sq Ft
  • Built 1915

  289 Clinton Rd, Brookline, MA 02445

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Bell | Whitman Group Compass
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  /5

  $5,950,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 4,825 Sq Ft

  9 Willard Rd, Brookline, MA 02445

  Unique opportunity to have your dream home built in the heart of Fisher Hill! 11,338 sf level lot with foundation and plans for a 4 bedroom, 3.5 bath classic brick colonial home with 4,825 square feet of space (on 3 levels) and a 2 car detached garage with shed. Gourmet kitchen opens to the den, dining and living room. First floor covered porch and terrace, perfect for al fresco dining.

  Celine Sellam Coldwell Banker Realty - Brookline

  9 Willard Rd, Brookline, MA 02445
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  /21

  $4,500 - $5,500

  Total Monthly Price

  • 3 - 4 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Condo for Rent

  9 Strathmore Rd, Brookline, MA 02445

  4BR / 2BA in Washington Sq./Cleveland Circle — 1,400 sq ft, Private Balcony, Shared Roof Deck$5,200/month | Available Immediately or September 1, 2026 | No Broker FeeMiddle-floor unit in a well-maintained 4-unit building on Strathmore Road. Move-in ready. Serious space, great light, and one of the shortest walks to the C and D lines you'll find at this price.The unit — 1,400

  9 Strathmore Rd, Brookline, MA 02445
• 

  

  /22

  $735,000

  Sold May 29, 2026

  1874 Beacon St Unit 4, Brookline, MA 02445

  • 2 Beds
  • 1 Bath
  • 955 Sq Ft
  • Built 1905

  Last Sold Summary

  • 1% Above List Price
  • $770/SF
  • 21 Days On Market

  Current Estimated Value $728,884

  Last Listing Agent Luan White Coldwell Banker Realty - Brookline

  1874 Beacon St Unit 4, Brookline, MA 02445
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  /26

  Est $2,313,882

  Not Listed For Sale

  357 Clinton Rd, Brookline, MA 02445

  • 6 Beds
  • 5 Baths
  • 3,577 Sq Ft
  • Built 1929

  357 Clinton Rd, Brookline, MA 02445

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Celine Sellam Coldwell Banker Realty - Brookline
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  /10

  $505,000

  Pending

  • 1 Bed
  • 1 Bath
  • 554 Sq Ft

  38 Kilsyth Rd Unit 23, Brookline, MA 02445

  Ideally situated on a picturesque tree-lined street between vibrant Washington Square and the scenic Chestnut Hill Reservoir. The unit feature a foyer with loads of shelving. The eat in kitchen has a microwave, dishwasher and disposal.Lovely living room with a wall of windows . The bedroom is generously sized .Additional highlights include high ceilings, hardwood floors, a kitchen with gas

  Debby Cohen Gibson Sotheby's International Realty

  38 Kilsyth Rd Unit 23, Brookline, MA 02445
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  /21

  $4,500 - $5,500

  Total Monthly Price

  • 3 - 4 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Condo for Rent

  9 Strathmore Rd, Brookline, MA 02445

  4BR / 2BA in Washington Sq./Cleveland Circle — 1,400 sq ft, Private Balcony, Shared Roof Deck$5,200/month | Available Immediately or September 1, 2026 | No Broker FeeMiddle-floor unit in a well-maintained 4-unit building on Strathmore Road. Move-in ready. Serious space, great light, and one of the shortest walks to the C and D lines you'll find at this price.The unit — 1,400

  9 Strathmore Rd, Brookline, MA 02445
• 

  

  /50

  $2,487,000

  Sold Dec 03, 2025

  333 Clark Rd, Brookline, MA 02445

  • 5 Beds
  • 3.5 Baths
  • 3,100 Sq Ft
  • Built 1915

  Last Sold Summary

  • 6% Below List Price
  • $802/SF
  • 70 Days On Market

  Current Estimated Value $2,574,029

  Last Listing Agent Cathy Sousa SERHANT.

  333 Clark Rd, Brookline, MA 02445
• 

  

  /27

  Est $608,422

  Not Listed For Sale

  1915 Beacon St Unit 1, Brookline, MA 02445

  • 1 Bed
  • 1 Bath
  • 577 Sq Ft
  • Built 1890

  1915 Beacon St Unit 1, Brookline, MA 02445

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Bonnie Lai 1st Knock Realty
• 

  

  /26

  $999,000

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

  1896 Beacon St Unit 3, Brookline, MA 02445

  Seller incentive! Sellers will credit up to $15,000 towards a rate buy-down. Offering both classic charm and detail with a modern touch, this spacious 3 bedroom 2 bathroom home has everything on your wish list. The living room features classic built-ins, bowed windows and a cozy fireplace. Directly off of the living room with french doors is a bedroom that also functions well as a office or flex

  Andrew McKinney Donnelly + Co.

  1896 Beacon St Unit 3, Brookline, MA 02445
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  /20

  $4,995 Plus Fees

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  1871 Beacon St Unit 3, Brookline, MA 02445

  Call today about this beautiful Brookline apartment. Plenty of space, natural light, and a charm all its own greet you every time you come home to this 1-bedroom apartment. Neighborhood amenities include dining, shopping, access to public transit, and more! You will love calling 1871 Beacon St. home. A/C All Utilities Included Cable Internet Included Eat-in Kitchen Fully

  1871 Beacon St Unit 3, Brookline, MA 02445
• 

  

  /19

  $1,220,000

  Sold Aug 03, 2026

  1896 Beacon St Unit 1, Brookline, MA 02445

  • 3 Beds
  • 3 Baths
  • 1,755 Sq Ft
  • Built 1905

  Last Sold Summary

  • 2% Below List Price
  • $695/SF
  • 28 Days On Market

  Current Estimated Value $1,230,339

  Last Listing Agent Claire McClintock Columbus and Over Group, LLC

  1896 Beacon St Unit 1, Brookline, MA 02445
• 

  

  /31

  Est $1,251,266

  Not Listed For Sale

  1891 Beacon St Unit 2, Brookline, MA 02445

  • 3 Beds
  • 2 Baths
  • 1,555 Sq Ft
  • Built 1910

  1891 Beacon St Unit 2, Brookline, MA 02445

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Yifei Wang Dreamega International Realty LLC
• 

  

  /23

  $1,495,000

  Open Sat 11AM - 12:30PM

  • 3 Beds
  • 2 Baths
  • 1,759 Sq Ft

  12 Kilsyth Rd Unit 3, Brookline, MA 02445

  Turnkey elegance in Washington Square! This exceptional, sun-drenched 3-bedroom, 2-full-bath residence spans 1,759 sq. ft. on the quiet 2nd floor of an intimate, professionally managed 4-unit building. Combining classic historic character with premium modern updates, the home features soaring high ceilings, meticulously restored original woodwork, oversized windows, and brand-new hardwood floors

  Michael Lukatsky Dream Home Realty

  12 Kilsyth Rd Unit 3, Brookline, MA 02445
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  /6

  $3,095 Plus Fees

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  1822 Beacon St Unit 7, Brookline, MA 02445

  Gorgeous layout. Huge closets. Equal sized bedrooms. Heat and hot water are included w/ rent. Cats allowed. Laundry availableHeat and hot water are included in the rent. Laundry on site. Cat welcome.Located on a very broad stretch of Beacon Street in Brookline and near Cleveland Circle. Very handy to Brookline parks, Brighton recreation fields, skating and swimming, the Ts Green

  1822 Beacon St Unit 7, Brookline, MA 02445
• 

  

  /30

  $3,085,000

  Sold Apr 29, 2026

  8 Penniman Rd, Brookline, MA 02445

  • 6 Beds
  • 5.5 Baths
  • 3,907 Sq Ft
  • Built 1930

  Last Sold Summary

  • 3% Above List Price
  • $790/SF
  • 6 Days On Market

  Current Estimated Value $3,055,342

  Last Listing Agent Celine Sellam Coldwell Banker Realty - Brookline

  8 Penniman Rd, Brookline, MA 02445
• 

  

  /19

  Est $1,098,119

  Not Listed For Sale

  1857 Beacon St Unit 1, Brookline, MA 02445

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft
  • Built 1900

  1857 Beacon St Unit 1, Brookline, MA 02445

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Stacey Steck Gibson Sotheby's International Realty

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