Head Of The Harbor, NY Homes

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  /19

  $2,900,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 5,340 Sq Ft

  17 Barn Ln, Saint James, NY 11780

  A Stunning home, nestled on 2 acres, offering incredible attention to detail. The open floor plan offers in excess of 5000 ft. with five bedrooms and 4 1/2 baths. Upon arrival, you are greeted by a gracious two-story entryway leading to a dramatic great room with gas fireplace and double-height coffered ceiling. The formal living room and dining room have 9 foot ceilings and an abundance of

  

  Deborah Pirro

  Daniel Gale Sothebys Intl Rlty

  (844) 310-9311

  17 Barn Ln, Saint James, NY 11780
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  Explore Head Of The Harbor

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  /7

  $5,500 per month

  • 5 Beds
  • 3 Baths
  • 3,600 Sq Ft
  • House for Rent

  26 Branglebrink Rd, Saint James, NY 11780

  This is a charming and spacious 5 BR 2.5 bath Colonial with 2 car garage in the prestigious Meadow Gate East private community. This home is set back on a woodsy shy 3 acre property w/ lawn maint incl.. There are no interior pix yet as the long term Tenant there is packing. The home is 3600 sq ft, , Formal Living Room + Dining Room, EIK, Den, wood burning fireplace, King Master BR suite w/full

  26 Branglebrink Rd, Saint James, NY 11780
• 

  $780,000 Sold Aug 27, 2025

  • Land
  • 2.4 Acres
  • $325,000 per Acre

  • 49 Days On Market

  Lot 1 Timothy Ln, Head of the Harbor, NY 11780

  Rare opportunity for flat parcel of cleared land on a cul-de-sac in the Incorporated village of Head of the Harbor. Surrounded by 4000-6000 sqft homes. This is an ideal location to build your dream home or a spec house. Water, electric at the property. Road paved in front of property. Located within 10 miles of major highways as well as private beaches.

  Alexia Poulos Douglas Elliman Real Estate

  Lot 1 Timothy Ln, Head of the Harbor, NY 11780
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  Est $790,468 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  40 Hitherbrook Rd, Saint James, NY 11780

  40 Hitherbrook Rd, Saint James, NY 11780
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  /23

  $1,699,000

  • 6 Beds
  • 3 Baths
  • 4,403 Sq Ft

  18 Watercrest Ct, Saint James, NY 11780

  Classic charm meets modern living! Set high on a beautiful two-acre property, this timeless cedar Colonial sits proudly on a cul-de-sac in the village of Head of Harbor. The grand two-story foyer leads to spacious living and dining rooms, a chef’s kitchen with Viking gas range and granite countertops, and a cozy family room with fireplace. A sunroom provides year-round views of the sparkling

  Filomena Tortorella Signature Premier Properties

  18 Watercrest Ct, Saint James, NY 11780
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  /50

  $20,000 per month

  • 6 Beds
  • 9.5 Baths
  • 6,500 Sq Ft
  • House for Rent

  2 Sunset Dr, Saint James, NY 11780

  Welcome to 2 Sunset Lane – a stunning 6-bedroom, 10-bath estate set on 3.9 beautifully landscaped acres, complete with a private tennis court and herb garden.Main Floor - Step into a grand foyer featuring a sweeping staircase and chandelier. The main level offers a formal dining room, a spacious open kitchen with breakfast nook, large island, and top-of-the-line Wolf range with double

  carol hurnyak Long Island Homes & Horse Prop

  2 Sunset Dr, Saint James, NY 11780
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  $2,300,000 Sold Aug 07, 2025

  • 5,130 Sq Ft
  • $448/SF
  • 113 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 1987

  1 Meadow Gate E, Saint James, NY 11780

  Welcome to 1 Meadow Gate East....A Stunning Estate with endless possibilities, set on 2 beautiful acres in the desirable Incorporated Village of Head of the Harbor! As you step through the elegant front doors, you’re welcomed by a bright and inviting atmosphere, w/ natural light pouring in and peaceful views of the natatorium w/ Resort style Indoor Premium PebbleTec Pool, offering a perfect mix

  Deborah Lettieri Signature Premier Properties

  1 Meadow Gate E, Saint James, NY 11780
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  Est $1,271,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,254 Sq Ft

  36 Harbor Rd, Saint James, NY 11780

  36 Harbor Rd, Saint James, NY 11780
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  /48

  $2,750,000

  • 6 Beds
  • 5.5 Baths
  • 4,900 Sq Ft

  33 Bacon Rd, Saint James, NY 11780

  Set On 3.5 Private Acres In The Prestigious Village Of Head Of The Harbor, 33 Bacon Road Is A Masterpiece Of Design, Craftmanship And Luxury. Built In 2012, This 4900 Square Foot Georgian Colonial Combines Timeless Architectural Elegance With Modern Conveniences, Offering An Unmatched Lifestyle In One Of Long Island's Most Sought-After Enclaves. The Approach To The Property Is Framed By Lush,

  Maria Orlandi Compass Greater NY LLC

  33 Bacon Rd, Saint James, NY 11780
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  /9

  $2,700 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  174 Mills Pond Rd Unit 2D, Saint James, NY 11780

  RARE FIND! Pristine and Lovely second floor 2-bedroom apartment in a prime location just minutes from shopping, dining, Stony Brook University, and Stony Brook Hospital. Perfect combination of convenience and comfort — an ideal opportunity you won’t want to miss. Rental includes 2 Bedrooms, Full Kitchen, nice size Living Room, Full Bathroom, and is a Second Floor Unit. Plenty of Parking. Great

  Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  174 Mills Pond Rd Unit 2D, Saint James, NY 11780
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  $2,600,000 Sold Aug 06, 2025

  • 8,000 Sq Ft
  • $325/SF
  • 22 Days On Market

  • 5 Beds
  • 8 Baths
  • Built 1985

  15 Armand Ct, Saint James, NY 11780

  A truly one-of-a-kind gated compound set on 2.4 lush meticulously manicured acres. This remarkable estate exudes a sense of serenity combined with a modern, open concept. Designed for those who appreciate high-end custom features and the finest in craftsmanship, this property offers an extraordinary living experience. This entertainer's paradise boasts an open and sophisticated living space

  Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  15 Armand Ct, Saint James, NY 11780
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  Est $1,151,797 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,689 Sq Ft

  1 Friends Way, Saint James, NY 11780

  1 Friends Way, Saint James, NY 11780
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  /37

  $1,199,000

  • 4 Beds
  • 3 Baths
  • 2,583 Sq Ft

  118 Harbor Rd, Saint James, NY 11780

  Welcome to 118 Harbor Road in the Beautiful Village of Head of The Harbor, NY. This Lovely Home is Nestled on 2 Acres of Serene and Rustic Property that backs to Multiple Acres of Wooded Land. The Generous-Sized Country Kitchen has a Breakfast Island with a Granite Counter, Built-in Wall Grill, Large Picturesque Window with View of Yard, The Living Room is a Generous Size with a 2-Sided

  Christine Stevens Daniel Gale Sothebys Intl Rlty

  118 Harbor Rd, Saint James, NY 11780
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  $1,450,000 Sold Jul 30, 2025

  • 3,600 Sq Ft
  • $403/SF
  • 85 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1999

  3 The Hunt, Saint James, NY 11780

  Spectacular and stately contemporary colonial style home boasting 5 bedrooms, 3 full bathrooms, a powder room off the fantastically open eat – in – kitchen with center island, a den with the warmth of a beautiful fireplace, , exceptional layout, full basement with high ceilings, and a parcel to die for. This tucked away ruby offers all the tranquility and serenity of the Head of the Harbor and

  Todd Yovino Island Advantage Realty LLC

  3 The Hunt, Saint James, NY 11780
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  Est $1,127,499 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths

  6 Buckingham Ct, Saint James, NY 11780

  6 Buckingham Ct, Saint James, NY 11780
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  /50

  $1,399,999 Open Fri 5PM - 7PM

  • 5 Beds
  • 5 Baths
  • 5,393 Sq Ft

  23 Bacon Rd, Saint James, NY 11780

  Welcome to 23 Bacon Road - The Best Value in the coveted Head of the Harbor ! This Elegant & expansive Ranch-Style home is nestled on 2.38 beautifully landscaped acres in the heart of Head of the Harbor. Built in 1960 & designed by renowned builder Yablonski - This home offers over 5,300 square feet of exquisite living space, This one-of-a-kind gem features a first floor master bedroom,

  James Szollosi Signature Premier Properties

  23 Bacon Rd, Saint James, NY 11780
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  $1,248,000 Sold Apr 07, 2025

  • 139 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1923

  17 Timothy Ln, Saint James, NY 11780

  Absolutely STUNNING only begins to describe this 5 bedroom, 3.5 Bath totally renovated colonial in the Village of Head of the Harbor. Gleaming hardwood floors and board and batten accents greet you as you enter into the foyer which then leads to the living room w/ fireplace. The living room has an entrance into the 4 seasons sun room/den as well as the formal dining room/sitting room. This brings

  Zachary Scher Signature Premier Properties

  17 Timothy Ln, Saint James, NY 11780
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  Est $1,584,390 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 5,253 Sq Ft

  21 Buckingham Ct, Saint James, NY 11780

  21 Buckingham Ct, Saint James, NY 11780
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  /27

  $1,439,000

  • 3 Beds
  • 3.5 Baths
  • 3,210 Sq Ft

  91 Harbor Rd, Saint James, NY 11780

  Dropped price!! This Diamond Pristine home is tucked away in a charming and highly desirable country setting. There are many updates throughout this sprawling ranch-style residence - including an abundance of New Hi Hat Lighting in every room, Gleaming hardwood floors, and Fully finished basement level, with a bedroom and customized closets, and a huge storage area. The home offers a rare

  Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  91 Harbor Rd, Saint James, NY 11780
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  $1,200,000 Sold Mar 27, 2025

  • 3,384 Sq Ft
  • $355/SF
  • 74 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1978

  30 Hitherbrook Rd, Saint James, NY 11780

  This home is fully available- deal on the table died- Welcome to 30 Hitherbrook Road in the beautiful Village of Head of the Harbor NY. Impeccably maintained traditional center hall cedar colonial nestled on a beautifully wooded two acre parcel. The home affords a formal living room, formal dining room, an office or sitting room, a spacious eat in kitchen with granite counters, new stainless

  John Sanders Shea & Sanders Real Estate Inc

  30 Hitherbrook Rd, Saint James, NY 11780
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  Est $1,440,960 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,200 Sq Ft

  19 the Chase, Saint James, NY 11780

  19 the Chase, Saint James, NY 11780
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  /6

  $800,000

  • Land
  • 2.33 Acres
  • $343,348 per Acre

  adj #552 Moriches Rd, Head of the Harbor, NY 11780

  Welcome to one of the most coveted and rare land offerings in the exclusive Village of Head of the Harbor. This extraordinary 2.33 acre lot presents a once-in-a-lifetime opportunity to build your dream estate in one of Long Island’s most desirable and picturesque communities.Situated on a serene and private parcel, this property comes permitted and ready to accommodate a spectacular

  Karyn Flores Compass Greater NY LLC

  adj #552 Moriches Rd, Head of the Harbor, NY 11780
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  $635,000 Sold Mar 13, 2025

  • 99 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1890

  1251 N Country Rd, Stony Brook, NY 11790

  As you come up the private road and into the driveway you will immediately fall in love with this charming home. Upon Entry, you will be invited into the formal living room with a beautiful mantle & fireplace, custom built-in shelving & archways. The formal dining room can become your home office. The Kitchen is open to a dining area and den with vaulted ceilings and French Doors leading to a

  David Guzzetta American Way Real Estate Inc

  1251 N Country Rd, Stony Brook, NY 11790
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  Est $1,836,422 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,394 Sq Ft

  4 Wicks Ln, Saint James, NY 11780

  4 Wicks Ln, Saint James, NY 11780
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  /44

  $4,000,000

  • 11 Beds
  • 7 Baths
  • 9,411 Sq Ft

  15 Emmet Dr, Stony Brook, NY 11790

  Step into a world of timeless elegance and unparalleled prestige at The Mallows — the crown jewel of the North Shore and one of the most exclusive waterfront estates in Head of the Harbor Village. Originally commissioned by the illustrious Astor family and masterfully designed by acclaimed architect Charles Platt, this historic masterpiece sprawls across 4+ acres of exquisitely landscaped grounds

  Michael Foley Frontline Realty Group LLC

  15 Emmet Dr, Stony Brook, NY 11790
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  $975,000 Sold Jan 08, 2025

  • 3,598 Sq Ft
  • $271/SF
  • 10 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1969

  30 Cordwood Path, Saint James, NY 11780

  House being Sold As Is. Located in Historic Village of Head of The Harbor this 4 Bedroom 3.5 Bathroom Ranch with Stunning views of Stony Brooke Harbor. Easy to show, Property being sold with an additional 2-acre plot next door.

  Shawn Rogol Compass Greater NY LLC

  30 Cordwood Path, Saint James, NY 11780
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  Est $1,230,450 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 4,355 Sq Ft

  29 Deepwells Ln, Saint James, NY 11780

  29 Deepwells Ln, Saint James, NY 11780
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  /37

  $899,000 Pending

  • 5 Beds
  • 2 Baths
  • 2,500 Sq Ft

  3 Nadia Ct, Saint James, NY 11780

  Welcome to 3 Nadia Court, a timeless New England-style Cape nestled on nearly 2.5 wooded acres in the exquisite village of Head of the Harbor. Tucked away on a quiet cul-de-sac, this 5-bedroom, 2-bathroom home offers the perfect blend of classic charm and serene privacy.Step through the front door into a large, welcoming foyer with original millwork that sets the tone for this warm and

  Monica Balsan Daniel Gale Sothebys Intl Rlty

  3 Nadia Ct, Saint James, NY 11780
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  $870,000 Sold Dec 17, 2024

  • 1,417 Sq Ft
  • $614/SF
  • 14 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1930

  178 Harbor Rd, Stony Brook, NY 11790

  Welcome to this charming 1930s Colonial nestled on a serene 0.5-acre lot, offering both timeless character and modern convenience. This adorable home features 3 bedrooms, 1.5 baths, and has been beautifully updated throughout. The property backs up to Avalon Nature Preserve, providing an abundance of peace and privacy. As you step inside, you'll be greeted by classic Colonial details like

  Michael O Dwyer Daniel Gale Sothebys Intl Rlty

  178 Harbor Rd, Stony Brook, NY 11790
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  Est $964,182 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,950 Sq Ft

  46 Harbor Hill Rd, Saint James, NY 11780

  46 Harbor Hill Rd, Saint James, NY 11780
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  /33

  $1,249,000 Pending

  • 5 Beds
  • 2.5 Baths
  • 2,541 Sq Ft

  537 Moriches Rd, Saint James, NY 11780

  A Rare Country Retreat on 3.5 Level Acres in Head of the HarborWelcome to a truly special property that captures the charm and serenity of a classic country estate—gracious, private, and full of old-world appeal. Set on an incredibly rare and completely level 3.5-acre parcel, this beautiful setting offers a sense of space and tranquility that’s hard to find. Located just minutes from Long

  Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  537 Moriches Rd, Saint James, NY 11780
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  $890,000 Sold Dec 06, 2024

  • 8 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1963

  32 Farm Rd, Saint James, NY 11780

  Discover a hidden gem nestled in the picturesque Incorporated Village of Head of the Harbor. This sprawling ranch-style home, set on a generous wide two-acre lot, offers the perfect blend of country living and convenience. Surrounded by lush greenery, this property provides a serene retreat while remaining just minutes away from town, shopping, Stony Brook University, restaurants, and

  Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  32 Farm Rd, Saint James, NY 11780
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  Est $764,525 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,485 Sq Ft

  29 Three Sisters Rd, Saint James, NY 11780

  29 Three Sisters Rd, Saint James, NY 11780
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  /7

  $445,000 Pending

  • Land
  • 2.64 Acres
  • $168,561 per Acre

  Lot 1.6 Brackenwoods Path, Head of the Harbor, NY 11780

  Wooded 2.64 Acre Lot on a Cul De Sac in Prestigious Head Of Harbor-Buy The Land Or Builders Can Be Provided-Stones Throw From The Water, Wineries, Horse Properties Private Location Custom Build Your Dream Home! Surveys Are Available

  Joseph Bartone Coldwell Banker American Homes

  Lot 1.6 Brackenwoods Path, Head of the Harbor, NY 11780
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  $1,725,000 Sold Nov 22, 2024

  • 48 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1997

  10 Buckingham Ct, Saint James, NY 11780

  This stunning all brick expansive colonial is nestled in a sought after location within the private Village of Head of the Harbor. Comprising of 5 Bedrooms and 3 full Bathrooms, this home exudes timeless elegance with its classic brick exterior and stately presence. Set on a lush 2-acre lot, this property is surrounded by other beautiful homes, creating an ambience of sophistication. Upon

  Bonnie Glenn Daniel Gale Sothebys Intl Rlty

  10 Buckingham Ct, Saint James, NY 11780
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  Est $1,166,824 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 3,173 Sq Ft

  6 Farm Rd, Saint James, NY 11780

  6 Farm Rd, Saint James, NY 11780
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  $900,000 Sold Oct 28, 2024

  • 3,565 Sq Ft
  • $252/SF
  • 89 Days On Market

  • 5 Beds
  • 3.5 Baths

  49 Harbor Hill Rd, Saint James, NY 11780

  Stunning Colonial Featuring 5 Bedrooms, 3.5 Bathrooms, 2-Car Garage Featuring Spacious Guest Quarters With Full Bathroom. High Ceilings, Crown Molding, And Hardwood Floors Throughout. A Large Gourmet Kitchen And Ample Cabinet Space. The Formal Dining Room Provides An Elegant Setting. Large Living Room W/ Fireplace, Main Floor Office. Upstairs, The Luxurious Master Suite Awaits, Boasting A

  Eduardo Ramirez Fresh Start Properties LLC

  49 Harbor Hill Rd, Saint James, NY 11780
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  Est $1,610,543 Not Listed For Sale

  • 10 Beds
  • 7 Baths
  • 6,250 Sq Ft

  10 Muffins Meadows, Saint James, NY 11780

  10 Muffins Meadows, Saint James, NY 11780
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  $1,450,000 Sold Oct 07, 2024

  • 3,086 Sq Ft
  • $470/SF
  • 21 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1979

  3 Cordwood Path, Saint James, NY 11780

  Welcome to 3 Cordwood Path, a rare gem nestled in the prestigious Head of Harbor section of Saint James, NY. Once part of the historic Stanford White estate, this property spans 2.61 acres of serene, partially wooded land, offering unparalleled privacy and a deep connection to nature. At the heart of this home is a stunning atrium adorned with natural plantings, a tranquil koi fish pond, and a

  Ricardo Pena The Agency Northshore NY

  3 Cordwood Path, Saint James, NY 11780
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  Est $1,117,565 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft

  25 Pinoak Ln, Saint James, NY 11780

  25 Pinoak Ln, Saint James, NY 11780

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