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5-Bedroom Homes for Sale in Old Greenwich, CT

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  • /43

    $3,895,000

    • 6 Beds
    • 5.5 Baths
    • 5,175 Sq Ft

    119 Hendrie Ave, Riverside, CT 06878

    This spacious Riverside Colonial is located on one of the less traveled streets extending from Riverside School to Binney Park. Artfully expanded & renovated from its original 40's design, the main rooms feature high ceilings, wide windows and generous scale. The dramatic three-story entrance hall is flanked by a formal living room & large family room , both w handsome fireplaces, & it extends

    Heather Platt Sotheby's International Realty

    119 Hendrie Ave, Riverside, CT 06878
  • /7

    $8,750,000

    • 6 Beds
    • 7.5 Baths
    • 10,400 Sq Ft

    11 Winterset Rd, Greenwich, CT 06830

    Mid Country New Construction smart home on 2.16 exquisite level acres will be completed by early fall, 2025. 10K+ SF of finished space on 4 floors with extra height ceilings throughout. Primary suite and 4 en-suite bedrooms on 2nd floor and a 6th en-suite bedroom on 3rd floor. Custom kitchen with Subzero/Wolf Appliances, island and breakfast area. Spectacular indoor / outdoor living is designed

    Amanda Bates Houlihan Lawrence Inc.

    11 Winterset Rd, Greenwich, CT 06830
  • /26

    $3,895,000

    • 5 Beds
    • 3.5 Baths
    • 3,647 Sq Ft

    258 Riverside Ave, Riverside, CT 06878

    Tucked away down a private driveway off Riverside Avenue, this stylishly updated, cedar-clad home offers the perfect blend of classic charm and modern farmhouse appeal. Set on over a half an acre of level lawn, this peaceful retreat is just minutes from the train, town and coastline. The sun-filled living room, framed by twin picture windows, sets a warm and welcoming tone. At the center of the

    Tracey Koorbusch Sotheby's International Realty

    258 Riverside Ave, Riverside, CT 06878
  • /19

    $1,399,000

    • 7 Beds
    • 3 Baths
    • 2,760 Sq Ft

    212 Davis Ave, Greenwich, CT 06830

    Renovated 3-Unit Multi-Family - Prime Location in Greenwich, CT! Whether you're looking to generate solid rental income or occupy one unit while renting out the others, this is a rare opportunity in the heart of Greenwich. Conveniently located near Greenwich Avenue, parks, schools, Metro-North, and I-95. Updates include: new roof, siding, insulation, electrical...

    Nico Jackson Corcoran Centric Realty

    212 Davis Ave, Greenwich, CT 06830
  • /35

    $3,275,000

    • 5 Beds
    • 2.5 Baths
    • 3,670 Sq Ft

    14 Highview Ave, Old Greenwich, CT 06870

    RARE OPPORTUNITY AND ENDLESS POSSIBILITIES ON OVERSIZED LOT IN THE HEART OF OLD GREENWICH! Charming, lived in and loved, this 1918 Colonial sits on one of OG's most desirable streets in The Village. The 3,670sf home blends timeless architecture with a welcoming layout and high ceilings. Additional FAR available for expansion. A wide wraparound front porch opens to well-proportioned entry hall,

    Christine McKelvey Corcoran Centric Realty LLC

    14 Highview Ave, Old Greenwich, CT 06870
  • /14

    $1,700,000

    • 7 Beds
    • 5 Baths
    • 3,713 Sq Ft

    47 Lindale St, Stamford, CT 06902

    Great Opportunity to own a beautiful 5 unit that has been totally redone in the heart of mid city Stamford. Two 2BR units and Three 1BR units comprise the house. 3 units have gas heat and 2 units have electric. New (roof, siding and windows). Coin-op laundry in lower level. Off street parking for 7 cars. Long term tenants. Rents are under market value. Month to month.

    Silvana Orsaia BHGRE Shore & Country

    47 Lindale St, Stamford, CT 06902
  • /32

    $2,400,000

    • 6 Beds
    • 8 Baths
    • 3,242 Sq Ft

    26 Homestead Ln, Greenwich, CT 06831

    New Construction Luxury Townhome style 2 Family featuring a total of 6 bedrooms, 6 Full Bathrooms, 2 half baths and 3,242 sq ft with rent potential of 15k-16k per month. Built with the best finishes in mind, flexible open floor plan, hardwood floors throughout and dream kitchens featuring custom cabinetry, large panties stainless steel chefs appliances, white oak island with built-in microwave

    Edward Zislis Higgins Group Real Estate

    26 Homestead Ln, Greenwich, CT 06831
  • /36

    $11,250,000

    • 5 Beds
    • 6 Baths
    • 5,638 Sq Ft

    200 Shore Rd, Old Greenwich, CT 06870

    Spectacular Waterfront Living in Lucas Point!Wake up to breathtaking sunrise views of Long Island Sound from this stunning Nantucket-style coastal retreat, nestled in the heart of sought-after Lucas Point. Just a short stroll to the private association beach, boat dock, and iconic Tod's Point, this home is your gateway to the ultimate Greenwich lifestyle.Thoughtfully designed for

    Robert Johnson Brown Harris Stevens CT, LLC

    200 Shore Rd, Old Greenwich, CT 06870
  • /27

    $2,925,000

    • 5 Beds
    • 4.5 Baths
    • 4,108 Sq Ft

    32 Meyer Place, Riverside, CT 06878

    This attractive and spacious 5-bedroom Colonial on peaceful cul-de-sac in Riverside was rebuilt and expanded in 2006 with a modern floor plan. The interior extends to 4,100 sq ft. with recent upgrades and extra ceiling height in many of the rooms providing generous scale and abundant natural light. The large kitchen with breakfast area flows to the expansive family room with fireplace. French

    Christopher Finlay Brown Harris Stevens CT, LLC

    32 Meyer Place, Riverside, CT 06878
  • /31

    $13,400,000

    • 6 Beds
    • 9 Baths
    • 11,157 Sq Ft

    31 Meadow Ln, Greenwich, CT 06831

    Exceptional Tanner White ultra-luxurious six-bedroom modern residence in the estate area of Greenwich. The open floor plan with 12+ foot ceilings is filled with natural light and allows for versatile use of the dramatic formal and casual rooms, all leading to a captivating outdoor living space complete with a fireplace overlooking the serene pool with spa and verdant lawn. The interior design and

    Leslie McElwreath Sotheby's International Realty

    31 Meadow Ln, Greenwich, CT 06831
  • /23

    $22,000,000

    • 8 Beds
    • 12 Baths
    • 14,071 Sq Ft

    8 Fox Run Ln, Greenwich, CT 06831

    Ultra-stylish 2024 custom-built Contemporary from visionary developer SBP Homes graces nearly 5.5 private, gated acres very close to town with pool, spa, two-bedroom pool house, porches, outdoor kitchen, fireplace and tennis court designed for optimum indoor/outdoor entertaining and relaxed living. Luxurious details elevate the 11,000+ sq. Interior with Bulthaup kitchen, living room bar; walls

    James Hoffman Houlihan Lawrence

    8 Fox Run Ln, Greenwich, CT 06831
  • /16

    $1,199,000

    • 5 Beds
    • 4 Baths
    • 2,775 Sq Ft

    442 Pepper Ridge Rd, Stamford, CT 06905

    JUST REDUCED! Move right in to this fully renovated 5-bed, 4-bath Stamford home blending modern luxury with peace of mind. The brand-new primary suite impresses with tray ceilings, dual walk-in closets, and a spa-inspired bath, while vaulted ceilings and a quartzite chef's kitchen create light-filled living and entertaining spaces. All major systems - roof, HVAC, plumbing, and electrical - have

    Daniel Morris Keller Williams Realty Group

    442 Pepper Ridge Rd, Stamford, CT 06905
  • /35

    $1,950,000

    • 5 Beds
    • 4.5 Baths
    • 3,050 Sq Ft

    22 Maplewood Dr, Cos Cob, CT 06807

    Where lifestyle, livability, and versatility meet... all your family & friends, too. Set in Cos Cob's tight-knit Loughlin Park, this 5 Bed home is in a prime location. Seconds to the train, a food scene, & the Park. With 3000 sqft of livability this home is a neighborhood hub. A garage & breezeway lead to open living, kitchen, & dining with a fireplace. Easy access to a grill, putting green, &

    Mike Parelli Mike Parelli Real Estate LLC

    22 Maplewood Dr, Cos Cob, CT 06807
  • /27

    $4,975,000

    • 6 Beds
    • 6.5 Baths
    • 5,970 Sq Ft

    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
  • /39

    $2,649,999

    • 6 Beds
    • 9 Baths
    • 6,191 Sq Ft

    72 Little Hill Dr, Stamford, CT 06905

    72 Little Hill Drive - Stately Colonial in the Heart of Newfield Privately nestled in one of Newfield's most sought-after neighborhoods, this grand colonial offers over 6,300 sq ft of beautifully finished living space, including 6 bedrooms, 5 full and 4 half baths, and a 4-car garage. Built in 1865 and fully renovated, the home blends timeless charm with modern luxury. The expansive backyard is

    Anthony Gaglio Jr Hathaway, Inc.

    72 Little Hill Dr, Stamford, CT 06905
  • /50

    $13,750,000

    • 6 Beds
    • 8 Baths
    • 9,418 Sq Ft

    52 Carriglea Dr, Riverside, CT 06878

    Experience unparalleled luxury in this extraordinary custom-built Riverside waterfront residence. Nestled on 1.45 acres with 9,418 square feet of living space, this exceptional home, designed by acclaimed architect Cormac Byrne, boasts a seamless open-concept layout that promotes effortless flow throughout. Soaring ceilings and expansive windows flood the interiors with natural light,

    Stephen Archino Sotheby's International Realty

    52 Carriglea Dr, Riverside, CT 06878
  • /52

    $13,995,000

    • 5 Beds
    • 9 Baths
    • 10,431 Sq Ft

    190 North St, Greenwich, CT 06830

    Nor Tor stands as one of Greenwich's finest English Manors, an extraordinary estate spanning nearly 3.5 acres of breathtaking beauty. Meticulously preserved, the manor underwent an extensive three year restoration and expansion, completed in 2010, blending historical integrity with seamless enhancements. This masterful renovation was led by architect Ira Grandberg, resulting in a breathtaking

    Leslie McElwreath Sotheby's International Realty

    190 North St, Greenwich, CT 06830
  • /37

    $18,500,000

    • 6 Beds
    • 9 Baths
    • 10,275 Sq Ft

    41 Meadow Wood Dr, Greenwich, CT 06830

    With breathtaking views of Long Island Sound, this custom-built Mediterranean-style home is nestled in an exclusive gated community known as Quarry Farm in Belle Haven. Featuring a terracotta-tiled roof, this luxurious home boasts 6-bedrooms and 6.3 baths on 4.7 acres of land. The central courtyard, which serves as the heart of the home, is surrounded by common living areas with extra-height

    Jennifer Ho Douglas Elliman of Connecticut

    41 Meadow Wood Dr, Greenwich, CT 06830
  • /51

    $11,400,000

    • 8 Beds
    • 10 Baths
    • 10,935 Sq Ft

    151 Old Church Rd, Greenwich, CT 06830

    ''Oak Castle Farm'', an extraordinary 7-bedroom turn-of-the-century English-style granite and shingle home, masterfully renovated and expanded under the supervision of noted architect, Alisberg Parker. Stunning 2014 transition incorporates relaxed grandeur with all modern-day luxuries. Exquisite detail, quality and scale with high ceilings throughout. Spectacular landscape and manicured grounds

    John McAtee Coldwell Banker Realty

    151 Old Church Rd, Greenwich, CT 06830
  • /40

    $5,495,000

    • 6 Beds
    • 5.5 Baths
    • 6,543 Sq Ft

    86 Wallacks Dr, Stamford, CT 06902

    Prestigious Waterfront Estate at Wallack's Point Experience the pinnacle of coastal luxury with this once-in-a-lifetime opportunity to own 1.46 acres of DIRECT Long Island Sound frontage in the gated enclave of Wallack's Point. With sweeping, unobstructed water views and nightly sunsets that feel like art, this premier waterfront property is among the most coveted on the Connecticut shoreline.

    Carla Kupiec William Raveis Real Estate

    86 Wallacks Dr, Stamford, CT 06902
  • /25

    $2,350,000

    • 5 Beds
    • 3.5 Baths
    • 3,634 Sq Ft

    551 River Rd, Cos Cob, CT 06807

    Bright newer five bedroom Center Hall Colonial near North Mianus school and minutes to Eastern Middle school , Riverside and Cos Cob shopping and RR stations. Third floor separate suite with bedroom, bath and office or sitting room. Hardwood floors , fenced in backyard. Great flow for day-to-day indoor and outdoor living and entertaining. Total Sq. footage includes 535 sq. ft. below grade.

    Maria Arning BHHS New England Properties

    551 River Rd, Cos Cob, CT 06807
  • /42

    $27,950,000

    • 8 Beds
    • 11.5 Baths
    • 13,428 Sq Ft

    45 Binney Ln, Old Greenwich, CT 06870

    This unparalleled custom-built modern waterfront estate, winner of 2021 HOBI-award, is a true oasis with 300'+ water frontage, pool, guest house, boat house, spa, expansive terraces integrated with gardens and deep water pier. Joeb Moore + Partners, Arthur Dunnam for Jed Johnson Studio, Reed Hilderbrand & Prutting Custom Builders collaborated on this spectacular LEED certified 13,428 sf compound

    Ellen Mosher Houlihan Lawrence

    45 Binney Ln, Old Greenwich, CT 06870
  • /18

    $11,000,000

    • 8 Beds
    • 7 Baths
    • 8,751 Sq Ft

    111 Byram Shore Rd, Greenwich, CT 06830

    Experience panoramic views from this 1.5-acre waterfront estate. The views stretch across the Long Island Sound from Greenwich to Oyster Bay, allowing you to enjoy both sunrises and sunsets over the water- all in complete privacy from neighboring properties. This one-of-a-kind distinctive contemporary offers a truly unique blend of cutting-edge modern design and historic charm, complete with

    Julie Church Houlihan Lawrence

    111 Byram Shore Rd, Greenwich, CT 06830
  • /10

    $11,900,000

    • 6 Beds
    • 9 Baths
    • 9,836 Sq Ft

    32 Pheasant Ln, Greenwich, CT 06830

    Welcome to 32 Pheasant Lane, a stunning completely rebuilt and expanded modern Colonial on one of Greenwich's most coveted streets. This exceptional 6 bedroom, 7.2 bath home offers over 9800 square feet of luxurious finished living space on 4 levels. An expansive front porch invites you inside where you will discover an open, airy floor plan with 10ft ceilings and custom details. White oak floors

    Maria Crowley Houlihan Lawrence

    32 Pheasant Ln, Greenwich, CT 06830
  • /75

    $13,750,000

    • 6 Beds
    • 8 Baths
    • 9,418 Sq Ft

    52 Carriglea Dr, Riverside, CT 06878

    Experience unparalleled luxury in this extraordinary custom-built Riverside waterfront residence. Nestled on 1.45 acres with 9,418 square feet of living space, this exceptional home, designed by acclaimed architect Cormac Byrne, boasts a seamless open-concept layout that promotes effortless flow throughout. Soaring ceilings and expansive windows flood the interiors with natural light,

    Stephen Archino Sotheby's International Realty

    52 Carriglea Dr, Riverside, CT 06878
  • /30

    $925,000

    • 5 Beds
    • 3 Baths
    • 2,868 Sq Ft

    340 Locust Ave, Port Chester, NY 10573

    Presenting an upgraded legal three-family residence, offering a blend of classic charm and modern amenities. This property is ideal for investors seeking strong rental income or homeowners looking for an owner-occupant opportunity with supplemental revenue.• Unit 1: Spacious 3-bedroom, 1-bathroom apartment featuring a large eat-in kitchen with stainless steel appliances. This ground-floor

    Carmen Santos Santos Realty Group, LLC

    340 Locust Ave, Port Chester, NY 10573
  • /31

    $8,950,000

    • 6 Beds
    • 5.5 Baths
    • 5,040 Sq Ft

    33 Meadow Wood Dr, Greenwich, CT 06830

    In the gated Quarry Farm neighborhood of the enchanting Belle Haven Association with 24hr security, this property offers a unique opportunity to renovate or build new, 16,000+ sq ft waterfront home. Overlooking Byram Harbor and Long Island Sound, the current 6-bedroom house sits on 2.78 acres with a pool, adjacent to a 1.09-acre protected lot. Once a quarry and later acquired as part of the

    Joseph Barbieri Sotheby's International Realty

    33 Meadow Wood Dr, Greenwich, CT 06830
  • /23

    $33,000,000

    • 8 Beds
    • 14 Baths
    • 18,954 Sq Ft

    555 Lake Ave, Greenwich, CT 06830

    Overlooking 8+park-like acres, this majestic brick Georgian was transformed to blend top of the line appointments with a rich array of custom detailing. Crowned by a 3-story chandelier, the impressive reception hall with Wenge walnut parquetry floor opens to a formal Dining Room with fireplace and elegant Living Room with fireplace and custom bar. Distinguished two-story English mahogany library

    Leslie McElwreath Sotheby's International Realty

    555 Lake Ave, Greenwich, CT 06830
  • /23

    $4,350,000

    • 6 Beds
    • 4.5 Baths
    • 4,958 Sq Ft

    121 Round Hill Rd, Greenwich, CT 06831

    Rare find - property on one of Greenwich' estate roads, Round Hill Rd. Oversized, private property, pool, stable, with a perfect blend of tranquil, manicured and natural landscapes. Enjoy your morning coffee gazing across beautiful east-facing rear vistas.Move right into this 5 bedroom 4 1/2 bath home, featuring upgrades like generator, irrigation, and largely new windows. Create your

    Sabine Schoenberg PrimeSites, Inc.

    121 Round Hill Rd, Greenwich, CT 06831
  • /19

    $2,799,000

    • 5 Beds
    • 5.5 Baths
    • 4,525 Sq Ft

    32 Jeffrey Rd, Greenwich, CT 06830

    A hidden gem close to town, updated and at the end of a cul-de-sac on a great quiet street, this beautiful 4,525-square-ft home on 1 acre offers a perfect blend of tranquility and convenience, located just minutes from town, the property boasts offices, 5 bedrooms, 5.5 baths, creating flexible layout, a perfect lifestyle for today's owner. Perfect for working from home or pursuing your passions.

    Lin Lavery Coldwell Banker Realty

    32 Jeffrey Rd, Greenwich, CT 06830
  • /11

    $4,350,000

    • Land
    • 2.30 Acres
    • $1,891,304 per Acre

    121 Round Hill Rd, Greenwich, CT 06831

    Rare find - property on one of Greenwich' estate roads, Round Hill Rd. Oversized,2.3 acres of private estate level property, pool, stable, with a perfect blend of tranquil, manicured and natural landscapes. Enjoy your morning coffee gazing across beautiful east-facing rear vistas. Property can't be appreciated from the street. This custom-designed 10,000 SF home (plan only)

    Sabine Schoenberg PrimeSites, Inc.

    121 Round Hill Rd, Greenwich, CT 06831
  • /43

    $24,950,000

    • 10 Beds
    • 19 Baths
    • 17,878 Sq Ft

    97 Pecksland Rd, Greenwich, CT 06831

    Truly unique 19 Acre estate in the heart of mid country! Prepared to be captivated by this custom built masterpiece of design and craftsmanship. Completed in 2009, and offered to the market for the first time since completion, 97 Pecksland has an unrivaled combination of lot size, quality and privacy. Enter through the grand gated entrance and dramatic driveway to the elevated main house on the

    Robert Johnson Brown Harris Stevens CT, LLC

    97 Pecksland Rd, Greenwich, CT 06831
  • /29

    $2,499,000

    • 5 Beds
    • 5 Baths
    • 3,598 Sq Ft

    201 Shore Rd, Greenwich, CT 06830

    1st house on Belle Haven peninsula offers bucolic commuter convenience in a most sought-after enclave overlooking Greenwich Harbor. Positioned atop slope with outstanding Harbor views, this 5 bed, 3 full & two half bathroom residence spans 3,598 sqft. Cleverly renovated to maximize water views with upgraded systems & interior improvements, this home marries smart functional privacy with today's

    Meg McAuley Kaicher Coldwell Banker Realty

    201 Shore Rd, Greenwich, CT 06830
  • /28

    $13,950,000

    • 6 Beds
    • 11 Baths
    • 15,171 Sq Ft

    537 North St, Greenwich, CT 06830

    Exquisite six bedroom, 7.4 bathroom stone manor executed to the highest standards sited on 2.97 picturesque acres. Chic and sophisticated interiors by Amy Hirsch throughout three levels of living space with extra high ceilings, oversized custom windows and all modern amenities. Elegant entry hall with a sweeping staircase and 3 stop elevator opens to a floor plan ideal for both formal and casual

    Leslie McElwreath Sotheby's International Realty

    537 North St, Greenwich, CT 06830
  • /34

    $22,000,000

    • 7 Beds
    • 5.5 Baths
    • 6,166 Sq Ft

    36, 38, 0 Game Cock Rd, Greenwich, CT 06830

    36, 38 and 0 Game Cock Road make up this 1.1+ acre island property that has been enjoyed as a multi generational family compound. One of only a few Island properties in Greenwich, let alone the Connecticut shoreline, to have it's own private bridge for access. The property boasts a 7 bedroom, 5 bath 6166 SQ FT main house, 3 en-suite bedroom 3238 SQ FT guest house, boathouse for entertaining,

    Brett Smith Brown Harris Stevens CT, LLC

    36, 38, 0 Game Cock Rd, Greenwich, CT 06830
  • /20

    $3,995,000

    • 5 Beds
    • 6.5 Baths
    • 4,570 Sq Ft

    59 Locust St Unit A, Greenwich, CT 06830

    Unparalleled opportunity to own a luxury condo with elevator right in the heart of downtown Greenwich. This is one of the most sought-after locations in Greenwich. This quiet tree lined one way street is walking distance to everything the downtown area has to offer- train, shops, library and restaurants.

    Nina Frandson Berkshire Hathaway NE Prop.

    59 Locust St Unit A, Greenwich, CT 06830
  • /21

    $1,200,000

    • 8 Beds
    • 5.5 Baths
    • 5,231 Sq Ft

    16 Greenwood Hill St, Stamford, CT 06902

    Ideal opportunity for this recently updated Rare find, large multi family home, bring your in-laws! Each side has 5+ bedrooms and 2.5 baths, gas boilers, updated electrical and much more. 48 hour notice.

    Mitchell Stevenson William Raveis Real Estate

    16 Greenwood Hill St, Stamford, CT 06902
  • /42

    $2,695,000

    • 5 Beds
    • 5.5 Baths
    • 2,885 Sq Ft

    65 Sherwood Place, Greenwich, CT 06830

    Scott Kelland CLS Group

    65 Sherwood Place, Greenwich, CT 06830
  • /42

    $7,600,000 New Construction

    • 8 Beds
    • 11 Baths
    • 8,567 Sq Ft

    148 E Elm St Unit 1&2, Greenwich, CT 06830

    Discover an investment opportunity or the perfect setting for multigenerational living at 148 East Elm St, Unit 1 and 2. These luxurious townhomes, together offering over 8,944 square feet of living space, feature a combined total of 8 bedrooms and 8.3 bathrooms. Each unit is thoughtfully designed with high-end amenities: an elevator, a gourmet kitchen with top-tier appliances, and an expansive

    Jenny Allen Compass Connecticut, LLC

    148 E Elm St Unit 1&2, Greenwich, CT 06830
  • /29

    $3,295,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 3,424 Sq Ft

    1 Sound View Terrace, Greenwich, CT 06830

    Minutes away from all Greenwich has to offer. Charming 5 bedroom home is within close distance to the train, park, shops and restaurants. The sun-filled, open layout features an entry that leads to a living room with a cozy fireplace, and a formal dining room perfect for entertaining. Kitchen with plenty of seating and office nook opens to a bright family room with access to a deck, ideal for

    Julie Church Houlihan Lawrence

    1 Sound View Terrace, Greenwich, CT 06830

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