Old Greenwich, CT Homes

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  /61

  $4,995,000

  • 4 Beds
  • 6 Baths
  • 5,244 Sq Ft

  34 Edgewood Dr, Greenwich, CT 06831

  Tucked discreetly at the end of a long, private drive in coveted mid-country Greenwich, masterfully renovated in 2025 this Colonial offers a harmonious blend of heritage architecture and sophisticated modernity. Designed to accommodate both grand-scale entertaining and intimate daily living, the residence unfolds across three levels and over 7,000 square feet of meticulously curated

  

  Danielle Malloy

  Serhant Connecticut LLC

  (203) 769-9185

  34 Edgewood Dr, Greenwich, CT 06831
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  /18

  $2,300 total monthly price

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

  215 Stillwater Ave Unit 416, Stamford, CT 06902

  Exceptionally bright & airy, this newer 1 bed/1-bath corner apartment features: extra windows, contemporary design, open floor plan, southwest skyline views & a variety of amenities to complement your life! Located on the brim of exciting downtown Stamford in a secure, well managed community, residents will enjoy an open kitchen, fully equipped with granite & stainless, living spaces lined with

  

  Melanie Healey

  Coldwell Banker Realty

  (475) 260-3681

  215 Stillwater Ave Unit 416, Stamford, CT 06902
• 

  $650,000 Sold Oct 17, 2025

  • 1,926 Sq Ft
  • $337/SF
  • 12 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1925

  72 Maher Rd, Stamford, CT 06902

  Welcome to this meticulously maintained 4-bedroom, 2-bathroom Colonial offering 1,926 square feet of living space. Set on a quiet side street in the desirable R-75 single-family zone, this classic home has had only two owners in its 96-year history and exudes timeless character throughout. The main level features a spacious living room, a comfortable dining room, and two generously sized bedrooms

  Ahdehroh Lambert Mortimore Premier Properties of CT

  72 Maher Rd, Stamford, CT 06902
• 

  Est $441,662 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,151 Sq Ft

  35 W Broad St Unit 105, Stamford, CT 06902

  35 W Broad St Unit 105, Stamford, CT 06902
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  /40

  $1,750,000 Open Sat 12PM - 2PM

  • 6 Beds
  • 5 Baths
  • 3,461 Sq Ft

  47 Hollow Tree Ridge Rd, Darien, CT 06820

  PRICE ADJUSTMENT. A Rare Darien Gem and opportunity to own this historic Federal Colonial 2-family home, one of Darien's few multi-family properties. Spanning over 3,460 SF on .47 acres, this turn-key furnished residence blends timeless elegance with modern versatility, ideal for investors, families, multi-generational households, or those seeking rental income. Historic Charm, Modern Comfort: *

  

  Karen Finn

  Gatehouse Realty Inc

  (475) 325-5924

  47 Hollow Tree Ridge Rd, Darien, CT 06820
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  /26

  $5,250 total monthly price

  • 4 Beds
  • 3 Baths
  • 1,967 Sq Ft
  • House for Rent

  259 Bruce Park Ave, Greenwich, CT 06830

  Classic colonial with a charming front porch in a convenient downtown location. This 4-bedroom home features updated baths, a finished lower level, and a spacious, private backyard perfect for outdoor living. Enjoy the convenience of being close to the train, parks, ferry, restaurants, and all that downtown Greenwich has to offer—move right in and make it home.

  

  Linna Yuen

  Coldwell Banker Realty

  (203) 457-6107

  259 Bruce Park Ave, Greenwich, CT 06830
• 

  $1,975,000 Sold Oct 17, 2025

  • 2,329 Sq Ft
  • $848/SF
  • 8 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1962

  11 Pond Place, Cos Cob, CT 06807

  Welcome to 11 Pond Place-a delightful 4 bedroom, 2 bathroom home located in the heart of Cos Cob. Offering 2,329 square feet of thoughtfully designed living space, this residence combines comfort, charm, and modern style. The spacious living room features a cozy fireplace, creating the perfect setting for relaxing or entertaining. A beautifully updated kitchen is ready for your culinary

  Lindsay Clauss Sheehy Compass Connecticut, LLC

  11 Pond Place, Cos Cob, CT 06807
• 

  Est $912,677 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,884 Sq Ft

  58 Lantern Cir, Stamford, CT 06905

  58 Lantern Cir, Stamford, CT 06905
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  /36

  $5,100,000

  • 6 Beds
  • 8 Baths
  • 7,930 Sq Ft

  20 Sherwood Farm Ln, Greenwich, CT 06831

  Step into luxury with this newly staged custom built home in one of Greenwich's prestigious associations. Perfectly situated near downtown, this elegant property offers a blend of sophistication and convenience- now at an improved price! A stunning custom built white Georgian Colonial in the coveted mid country Sherwood Farm Association is sited on a picturesque level acre lot. This six bedroom

  

  Richard Higgins

  Higgins Group Bedford Square

  (203) 433-0559

  20 Sherwood Farm Ln, Greenwich, CT 06831
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  /21

  $2,855 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft
  • House for Rent

  215 Stillwater Ave Unit 319, Stamford, CT 06902

  Exceptionally newer, bright & airy, this 2 bed/2-bath corner apartment features contemporary design, open floor plan, southwest skyline views & a variety of amenities to complement your life! Located on the brim of exciting downtown Stamford in a secure, well managed community, residents will enjoy an open kitchen, fully equipped with granite & stainless, living spaces lined with big windows, a

  

  Melanie Healey

  Coldwell Banker Realty

  (475) 473-9405

  215 Stillwater Ave Unit 319, Stamford, CT 06902
• 

  $958,000 Sold Oct 17, 2025

  • 1,825 Sq Ft
  • $525/SF
  • 14 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2009

  1 Broad St Unit 15A, Stamford, CT 06901

  Experience luxury living at its finest in the heart of Stamford, with breathtaking views of downtown, Mill River Park & the Long Island Sound. This exquisite 3 bedroom, 3 1/2 bath home offers an expansive open floor plan with floor-to-ceiling windows designed to maximize light & showcase the stunning scenery. Thoughtfully designed with attention to every detail, the home features custom electric

  Casey Lange Compass Connecticut, LLC

  1 Broad St Unit 15A, Stamford, CT 06901
• 

  Est $2,347,270 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 5,735 Sq Ft

  25 Wallacks Dr, Stamford, CT 06902

  25 Wallacks Dr, Stamford, CT 06902
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  /36

  $1,410,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,552 Sq Ft

  17 Lynn Ct, Darien, CT 06820

  This is the one you've been waiting for! Spacious 4 BR, 3 BA home in coveted, friendly neighborhood conveniently located within walking distance to Holmes School. Recent 2-story addition includes dreamy new primary suite with 10' ceiling, large new primary bath with jacuzzi tub, walk-in closet, upper-level laundry and walk-up attic-one of TWO attics! Three more bedrooms and two full baths, formal

  

  Karen Finn

  Gatehouse Realty Inc

  (203) 780-0811

  17 Lynn Ct, Darien, CT 06820
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  /16

  $2,200 total monthly price

  • 1 Bed
  • 1 Bath
  • 674 Sq Ft
  • House for Rent

  215 Stillwater Ave Unit 415, Stamford, CT 06902

  Charming & Newer 4th Floor Apartment in Modern Mid-Rise Building offers flexible floor plan with stylish details! This newer, pet friendly apartment features contemporary design & a variety of amenities to complement your life! Located on the brim of exciting downtown Stamford, close to UCONN + public golf course, in a secure, well managed community, residents will enjoy a gourmet kitchen, fully

  

  Melanie Healey

  Coldwell Banker Realty

  (475) 260-8620

  215 Stillwater Ave Unit 415, Stamford, CT 06902
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  /27

  $4,780,000 Sold Oct 17, 2025

  • 5,970 Sq Ft
  • $801/SF
  • 111 Days On Market

  • 6 Beds
  • 6.5 Baths
  • Built 2007

  52 Breezemont Ave, Riverside, CT 06878

  Renovated in 2025 this exquisite home features a grand triple-height foyer and stunning hardwood floors throughout. A bright living room flows seamlessly onto a wraparound porch. Inviting eat- in kitchen includes Viking appliances, a center island, a wine refrigerator and elegant marble countertops. Family room has a wet bar and fireplace while the dining room is adorned with wainscoting and

  Jennifer Danzi-glenn Jennifer M Danzi, Broker

  52 Breezemont Ave, Riverside, CT 06878
• 

  Est $514,925 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,126 Sq Ft

  13 Willowbrook Place, Stamford, CT 06902

  13 Willowbrook Place, Stamford, CT 06902
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  /36

  $1,300,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,120 Sq Ft

  20 Denhurst Place, Darien, CT 06820

  Welcome to 20 Denhurst Place - a lovingly maintained Colonial proudly owned by the same family since it was built. Perfectly situated on a quiet private street in highly sought-after Darien, this inviting home combines comfort, convenience, and timeless charm. Enjoy a premier location just a short walk to Holmes Elementary School and the Glenbrook Train Station, with easy access to I-95, the

  

  Len Schwartz

  Keller Williams Prestige Prop.

  (203) 344-7572

  20 Denhurst Place, Darien, CT 06820
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  /26

  $4,250 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • House for Rent

  19 Valley Rd, Cos Cob, CT 06807

  Easy living in central Cos Cob. Gracious 3 bedroom 2bathroom townhouse. Hardwood floors and air-conditioning. Large master with dressing. Just a few minutes walk to coffee and pastry or 14 minute walk to the train. Large beautiful deck, covered front porch and small garden . Off and on street parking. Gas heating and cooking. Only a couple blocks to school, playground and park.

  

  Scott Kadison

  Scott Kadison Real Estate

  (203) 344-8881

  19 Valley Rd, Cos Cob, CT 06807
• 

  $9,750,000 Sold Oct 17, 2025

  • 8,896 Sq Ft
  • $1,096/SF
  • 106 Days On Market

  • 6 Beds
  • 8 Baths
  • Built 2008

  35 Club Rd, Riverside, CT 06878

  Sought after Riverside location showcases a stunning six-bedroom Colonial built by Sound Beach Partners with pool, porches, outdoor fireplace and grill on beautifully manicured .71 acres with private yard dotted with sequentially flowering trees. Offers easy access to trains, schools, water and Yacht Club. This pristine home exudes classic elegance with superb architectural details, wood floors,

  Andrew Smith Houlihan Lawrence

  35 Club Rd, Riverside, CT 06878
• 

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,318 Sq Ft

  20 Church St Unit B22, Greenwich, CT 06830

  20 Church St Unit B22, Greenwich, CT 06830
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  /22

  $445,000

  • 1 Bed
  • 1 Bath
  • 673 Sq Ft

  351 Pemberwick Rd Unit 111, Greenwich, CT 06831

  Located in the desirable Hawthorne Condominium complex, this 1-bedroom, 1-bath unit offers a comfortable and convenient living space. The bright and airy layout features a kitchen with quartz countertops and newer stainless steel appliances. Adjacent to the kitchen is a versatile utility/laundry room (newer washer/dryer) that provides extra storage. The open floorplan seamlessly connects the

  

  Ellen Garcia

  Brown Harris Stevens

  (475) 260-8762

  351 Pemberwick Rd Unit 111, Greenwich, CT 06831
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  /29

  $4,800 total monthly price

  • 2 Beds
  • 2 Baths
  • House for Rent

  13 High St, Greenwich, CT 06830

  Perfect Package. Single family gem with Large Fenced Yard, approx. 50X50. Grounds maintenance, trash and snow removal included. Nicely updated. Two car garage (Auto Open) with large driveway. Attic and basement storage. Family room with an-suit full bathroom can be a 3rd bedroom, Low gas heat and utility costs with 4 zones. Near Beach, Pool , supermarkets and down town area

  

  Scott Kadison

  Scott Kadison Real Estate

  (203) 580-6926

  13 High St, Greenwich, CT 06830
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  /26

  $7,000,000 Sold Oct 17, 2025

  • 14,149 Sq Ft
  • $495/SF
  • 544 Days On Market

  • 12 Beds
  • 12 Baths
  • Built 1909

  140 Wallacks Dr, Stamford, CT 06902

  Private 3.5-acre ''Caritas Island'' on Long Island Sound with 300-degree cinematic waterfront views. Accessed by a gated causeway, the expansive compound includes: a c1909 stone main house with 12 bedrooms and 10 baths, stunning waterside terraces and a lap pool; a c1870 3-bedroom stone guest cottage and a 6-car detached garage with 2 staff apartments above. Protected by a stone breakwater, the

  Joseph Barbieri Sotheby's International Realty

  140 Wallacks Dr, Stamford, CT 06902
• 

  Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 5,627 Sq Ft

  48 Glenville Rd, Greenwich, CT 06831

  48 Glenville Rd, Greenwich, CT 06831
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  /17

  $646,000

  • 2 Beds
  • 2 Baths
  • 1,199 Sq Ft

  2289 Bedford St Unit G17, Stamford, CT 06905

  Don't miss the opportunity to own this first-floor unit in Chesterfield, one of Stamford's most sought-after-gated communities. This 2-bedroom, 2-bathroom unit is situated in a very desirable section of the complex. It also includes a garage conveniently located outside your back door, which is rarely found in Chesterfield. The living room is bright and spacious, complete with a fireplace and

  

  Glenn Marr

  Marr Caruso Realty Group

  (475) 260-9100

  2289 Bedford St Unit G17, Stamford, CT 06905
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  /25

  $5,950 total monthly price

  • 4 Beds
  • 2 Baths
  • 2,204 Sq Ft
  • House for Rent

  83 Linden Ave, Darien, CT 06820

  A charming, cozy historic home with modern amenities and close to everything, including Darien Commons, Heights Crossing and Noroton Heights train station. Country kitchen renovated by Deane Inc. with Viking gas cooktop. 4 bedrooms, 2 full baths plus dining room, den and family room. In addition, there is a 1st floor sun room/gym/office, oversized walk in pantry, laundry area and 2nd floor office

  

  Robert Marchesi

  Compass Connecticut, LLC

  (203) 666-4120

  83 Linden Ave, Darien, CT 06820
• 

  $600,000 Sold Oct 16, 2025

  • 1,700 Sq Ft
  • $353/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  1 Strawberry Hill Ave Unit 16B, Stamford, CT 06902

  Rare opportunity to own a 3-bedroom mid city penthouse. This expansive 1,700 sq ft residence offers a seamless single-level floor plan. Enjoy breathtaking sunsets as well as city and water views from the privacy of your freshly painted home. The screened-in balcony is a natural extension of the living space, making it easy to step outside for a breath of fresh air. A combination of great closets

  Randy Musiker Compass Connecticut, LLC

  1 Strawberry Hill Ave Unit 16B, Stamford, CT 06902
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  /25

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 673 Sq Ft

  351 Pemberwick Rd Unit 206, Greenwich, CT 06831

  351 Pemberwick Rd Unit 206, Greenwich, CT 06831
• 

  

  /26

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,610 Sq Ft

  143 Hoyt St Unit 3B, Stamford, CT 06905

  Spacious, sun-filled, and FULLY UPDATED 2-bedroom, 2-full bath condo in the highly sought-after Buckingham Association offers 1,600+ sq ft of stylish, turnkey living. Enjoy a beautifully remodeled kitchen featuring pristine white cabinetry, gleaming granite countertops, granite tile backsplash, stainless steel appliances -- including a beverage refrigerator -- and an open layout ideal for

  

  Len Schwartz

  Keller Williams Prestige Prop.

  (475) 303-5771

  143 Hoyt St Unit 3B, Stamford, CT 06905
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  /13

  $4,900 total monthly price

  • 3 Beds
  • 2.5 Baths
  • Condo for Rent

  82 Cos Cob Ave, Greenwich, CT 06807

  Quality recent renovated from Top to Bottom.Primary bedroom with vaulted ceiling and en-suite bathroom.Central AirFull clean dry basement with large washer/dryer.Recessed LED lighting. Hardwood floors.Brick wood burning Fireplace. Private Deck.Close to all the amenities Greenwich has to offer.

  

  Scott Kadison

  Scott Kadison Real Estate

  (475) 338-3609

  82 Cos Cob Ave, Greenwich, CT 06807
• 

  $899,000 Sold Oct 15, 2025

  • 1,723 Sq Ft
  • $522/SF
  • 37 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1946

  170 Woodbury Ave, Stamford, CT 06907

  Beautifully maintained and thoughtfully updated Cape Cod in sought-after Springdale, just minutes from parks, the train station, shopping, and dining. Step inside to a welcoming living room with a cozy fireplace, leading to a sun-filled eat-in kitchen with dining area and seamless access to the back deck and private level yard. The main floor features two spacious bedrooms, a renovated full bath,

  Jennifer Leahy Compass Connecticut, LLC

  170 Woodbury Ave, Stamford, CT 06907
• 

  Est $6,116,370 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 5,124 Sq Ft

  2 Baywater Dr, Darien, CT 06820

  2 Baywater Dr, Darien, CT 06820
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  /11

  $235,000

  • 1 Bath
  • 491 Sq Ft

  1856 Summer St Unit 1856, Stamford, CT 06905

  INVEST IMMEDIATELY OR LIVE IN LATER! LEASE IN PLACE UNTIL MARCH 2026. This Bright, open and well presented studio is tucked away in the heart of mid-city and features your own private entrance & reserved parking - this fabulous studio has a newer white kitchen that leads to a sunny open floor plan, featuring great lighting, private storage and a little patio space to enjoy the outdoors. Your

  

  Melanie Healey

  Coldwell Banker Realty

  (203) 816-6362

  1856 Summer St Unit 1856, Stamford, CT 06905
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  /15

  $3,200 total monthly price

  • 2 Beds
  • 1 Bath
  • Apartment for Rent

  15 Scofield St Unit 1F, Greenwich, CT 06807

  Simple , Clean , Bright.FREE HEAT and HOT WATER!BRAND NEW KITCHEN!Total new paint job.WASHER/DRYER in UnitSmall pet okay.Walk to Pizza. One mile to train.

  

  Scott Kadison

  Scott Kadison Real Estate

  (475) 251-4720

  15 Scofield St Unit 1F, Greenwich, CT 06807
• 

  $497,000 Sold Oct 15, 2025

  • 1,384 Sq Ft
  • $359/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1975

  135 Courtland Ave Unit 22, Stamford, CT 06902

  Welcome to Anderson Ridge, Unit 22. A bright and spacious three-level townhome located in Stamford's desirable Glenbrook neighborhood. Offering approximately 1,384 square feet of living space, this well-maintained home combines comfort, functionality, and community amenities in a prime location walkable to the water! Property Highlights * 3 bedrooms | 2 full baths | 1 half bath - plenty of space

  Mike McGill Compass Connecticut, LLC

  135 Courtland Ave Unit 22, Stamford, CT 06902
• 

  Est $3,505,513 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 5,229 Sq Ft

  141 Downs Ave, Stamford, CT 06902

  141 Downs Ave, Stamford, CT 06902
• 

  

  /13

  $1,995,000

  • 4 Beds
  • 4.5 Baths
  • 3,363 Sq Ft

  282 Bruce Park Ave Unit 2, Greenwich, CT 06830

  Close to Metro North train station! 4BR, 4.5 Bath Luxury Four-story Living-Top floor - 1b/1b with sky windows full of nature lights. plus an extra office space or gym room; 2nd floor - 2b/2b, Primary bedroom suite has custom designed walk-in closet/dressing room and jacuzzi bath with gas fireplace; Guest room also has full bath with dress room. 1st fl - open floor plan, Gourmet kitchen has

  

  Glenn Marr

  Marr and Caruso Realty Group

  (203) 601-7427

  282 Bruce Park Ave Unit 2, Greenwich, CT 06830
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  /25

  $4,995 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,905 Sq Ft
  • House for Rent

  189 Turner Rd, Stamford, CT 06905

  Come see this beautifully renovated home in desirable Newfield ~ unpack and enjoy this immaculate cheerful space!! Some furnishings can remain. Sparkling new kitchen with entertainer's island opens to an easy flow of sunny, spacious rooms lined with rich & pretty hardwood flooring. Formal living room with fireplace leads to a window-lined den, ideal for your home office! First floor primary suite

  

  Melanie Healey

  Coldwell Banker Realty

  (203) 457-6551

  189 Turner Rd, Stamford, CT 06905
• 

  $465,000 Sold Oct 15, 2025

  • 1,534 Sq Ft
  • $303/SF
  • 22 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1971

  40 Lindstrom Rd, Stamford, CT 06902

  Welcome to Harbor View Court at the gateway to Shippan Point in Stamford. This 2-bedroom 1.5 bath end unit home is a rare find in one of the most sought-after water front neighborhoods in Stamford. This tri level home has more than 1,500 square feet, including the lower level. As the result of being an end unit the living area is very bright, and features wonderful open living. Both bedrooms are

  Howard Dubman Century 21 AllPoints Realty

  40 Lindstrom Rd, Stamford, CT 06902
• 

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 1,940 Sq Ft

  115 Colonial Rd Unit 48, Stamford, CT 06906

  115 Colonial Rd Unit 48, Stamford, CT 06906

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