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Homes for Sale near Pawling Middle School

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  • /25

    $469,000

    • 4 Beds
    • 2.5 Baths
    • 1,608 Sq Ft

    120 South Rd, Holmes, NY 12531

    Welcome to 120 South Rd/40 Great Bear Rd, a charming home at the end of a quiet cul-de-sac, offering peace, privacy, and a stunning lake view from the deck. Set on just under 3 acres, this property features a spacious front yard shaded by mature trees, perfect for outdoor gatherings, gardening, or simply relaxing in your own private oasis. Enjoy the comfort and efficiency of new windows

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    Omar Harper

    Epique Realty

    (845) 552-1998

    120 South Rd, Holmes, NY 12531
  • /42

    $598,500

    • 4 Beds
    • 4.5 Baths
    • 2,361 Sq Ft

    126 Old Route 55, Pawling, NY 12564

    Back on the market, the deal fell through from the buyer side. 9/17/2025 This house is owned by a church and in New York a sale has to be approved by the Attorney Generals office which can take up to six months. This can work to your benefit depending on your own timeline. This can also be set up a s a short term rental as well while waiting for the approvals WITH PORTION OF RENT GOING TOWARDS

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    Philip Bisesto

    HomeSmart Homes & Estates

    (845) 576-1665

    126 Old Route 55, Pawling, NY 12564
  • /32

    $1,400,000

    • 11 Beds
    • 8 Baths

    750 Route 292, Holmes, NY 12531

    Multi-generational housing opportunity with 3 individual homes on one property. 3 distinct home styles with plenty of options. The perfect balance of togetherness and privacy. And investors - you may want to give this property some serious consideration as well.Unit A: Colonial style renovated home. Hardwood floors, crown molding and recessed lighting throughout. Spacious Living Room with

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    Judith 'Judy' Albert

    BHHS Hudson Valley Properties

    (845) 957-9518

    750 Route 292, Holmes, NY 12531
  • /28

    $537,500

    • 3 Beds
    • 3.5 Baths
    • 2,106 Sq Ft

    101 Bundy Hill Rd, Holmes, NY 12531

    Nestled in between trees and rocks, privacy abounds in this Contemporary Colonial style dwelling with numerous upgrades. A down to the studs remodel in 2016, the home boasts generous open concept living, dining and kitchen areas all with recessed lighting. Kitchen includes butcherblock counter tops and stainless-steel appliances. Entry nook convenient for coats, purses, backpacks and shoes. First

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    Judith 'Judy' Albert

    BHHS Hudson Valley Properties

    (845) 299-9362

    101 Bundy Hill Rd, Holmes, NY 12531
  • /6

    $87,500

    • Land
    • 0.46 Acre
    • $190,217 per Acre

    0 Lakeview Dr Unit KEY962482, Pawling, NY 12531

    Build your ideal home on this prime .46-acre lot perfectly situated within the sought-after Pawling Lake Estates community. Offering a rare blend of beauty and value, this property boasts picturesque views of Jones Pond and benefits from the lower property taxes of the Dover Union Free School District. Nature enthusiasts will love being surrounded by the sprawling West Mountain State Forest,

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    Colleen McGrath

    McGrath Realty Inc

    (845) 385-2808

    0 Lakeview Dr Unit KEY962482, Pawling, NY 12531
  • /11

    $229,000

    • Land
    • 6.63 Acres
    • $34,540 per Acre

    Lot 25 Brady Brook Farm Rd, Pawling, NY 12564

    Come build your dream home on this 6.63-acre Board of Health–approved lot in the desirable Brady Brook Falls community of Pawling. Approved for a 5-bedroom home, this property offers the perfect setting for those seeking privacy while remaining just minutes from all the conveniences the Town of Pawling has to offer. Enjoy easy access to Route 22, Route 55, Metro-North, shopping, the charming

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    Shannon Tully

    McGrath Realty Inc

    (845) 378-9417

    Lot 25 Brady Brook Farm Rd, Pawling, NY 12564
  • /6

    $225,000

    • Land
    • 0.76 Acre
    • $296,053 per Acre

    15 Dykeman St, Pawling, NY 12564

    Rare opportunity to build in the heart of the Village of Pawling! Cleared and ready for development, this residential lot at 15 Dykeman Street offers municipal water and sewer available at the street — a major advantage for new construction. The property features a defined driveway lined with item four stone, providing immediate access and a head start on site work. Level and open, the lot offers

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    Joanne Debellis

    Debellis Real Estate LLC

    (845) 660-6758

    15 Dykeman St, Pawling, NY 12564
  • /22

    $1,350,000

    • Land
    • 3.9 Acres
    • $346,154 per Acre

    178 Charles Colman Blvd, Pawling, NY 12564

    Exclusive Mixed-Use Property in Pawling N.Y.! Incredible Investment or Business Opportunity offering a rare blend of Residence, Greenhouse, Floral Shop, & Nursery.This beautiful Sprawling estate boasts a Commercial c & Residential component? with a 2,500 sqft greenhouse fully-equipped floral shop with retail space There is Ample parking & easy accessibility for Commercial

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    Vince Buccieri

    Today Realty Corp.

    (845) 280-5951

    178 Charles Colman Blvd, Pawling, NY 12564
  • /48

    $1,175,000

    • 5 Beds
    • 4 Baths
    • 4,248 Sq Ft

    64 S Quaker Hill Rd, Pawling, NY 12564

    Welcome to Country Living at Its Finest!Nestled on 24.5 scenic acres, this classic 1910 farmhouse offers endless potential for those looking to restore a piece of history. A long, tree-lined driveway leads to this charming 4-bedroom, 4-bath home surrounded by open fields, mature trees, and peaceful country views. The property features a spacious 4-car garage with finished living space with

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    Shannon Tully

    McGrath Realty Inc

    (845) 415-7723

    64 S Quaker Hill Rd, Pawling, NY 12564
  • /37

    $775,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 3,611 Sq Ft

    4 Mane Way, Pawling, NY 12564

    Elegant and Updated Center Hall Colonial, ideally situated in The Highlands—a beautiful and highly sought-after neighborhood in the charming Town of Pawling. This spacious four-bedroom, two-and-a-half-bath home seamlessly blends timeless architectural character with modern luxury, offering comfort, style, and functionality for today’s lifestyle. Gleaming hardwood floors flow throughout the main

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    Sharon Sheil

    Coldwell Banker Realty

    (845) 443-7838

    4 Mane Way, Pawling, NY 12564
  • /33

    $9,750,000

    • Land
    • 558.35 Acres
    • $17,462 per Acre

    225 Route 22, Pawling, NY 12564

    Unparalleled Opportunity Awaits! Discover this breathtaking 558+ acre parcel, just 90 minutes from Manhattan, offering a canvas of endless possibilities for personal and commercial endeavors. Whether you envision a sprawling family compound or a premier commercial facility, this land is primed for your dreams. Featuring level terrain, extensive trails, and vibrant pastures, this property is

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    Shaylene Neumann

    Houlihan Lawrence Inc.

    (845) 377-2512

    225 Route 22, Pawling, NY 12564
  • /8

    $229,000

    • Land
    • 5.57 Acres
    • $41,113 per Acre

    Lot 21 Cox Rd, Pawling, NY 12564

    Come build your dream home on this 5.6-acre Board of Health–approved lot in the highly desirable Brady Brook Falls community of Pawling. Approved for a 5-bedroom residence, this property offers both privacy and convenience—just minutes from Route 22, the Village of Pawling, shopping, Metro-North, Route 55, and even the Appalachian Trail. Nestled within the Oblong Trails, residents of Brady Brook

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    Shannon Tully

    McGrath Realty Inc

    (845) 328-6866

    Lot 21 Cox Rd, Pawling, NY 12564
  • /45

    $499,000

    • 4 Beds
    • 2 Baths
    • 1,210 Sq Ft

    23 Lakeview Dr, Holmes, NY 12531

    You get to enjoy the Lakehouse lifestyle all year round at this newly updated raised ranch. Convenient to the restaurants and shops of downtown Pawling and your pick of the Pawling, Patterson, or Southeast Metro North stations as well as I-84 and the Taconic State Parkway. The current owner has made extensive improvements to the property, including all new baths and a master bedroom with

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    Lisbeth Furke

    World Homes Realty

    (845) 851-0605

    23 Lakeview Dr, Holmes, NY 12531
  • /24

    $590,000

    • Land
    • 63.9 Acres
    • $9,233 per Acre

    489 Grape Hollow Rd, East Fishkill, NY 12531

    Calling out for BUILDERS, HUNTERS, MULTI FAMILY HOMES OR LUXURY home owner desiring total privacy!! 63.9 acres of woodland in the Hudson Valley, undeveloped parcel. Prior approval ( needs to be updated by the buyer and engineer ) by the town for a 4 parcel to a 10 plot subdivision and has 3 wells drilled on parcels already, build less homes as desired with larger land parcels. OR Build a dream

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    Philip Bisesto

    HomeSmart Homes & Estates

    (845) 683-5349

    489 Grape Hollow Rd, East Fishkill, NY 12531
  • /44

    $848,800

    • 3 Beds
    • 2.5 Baths
    • 3,026 Sq Ft

    57 S White Rock Rd, Holmes, NY 12531

    Nestled in the hamlet of Pawling, NY. This rare find in Holmes is a gorgeous Four-SQ. colonial custom & unique property and a must see. Privacy awaits in a pristine area with nearly 5 acres. Enchanting landscapes surround the property, patio and waterfall. Inside this colonial farmhouse is a beautiful blend of comfort and unique craftsmanship that is well-loved. Every single detail of the house

    Patrice Copeland-Ainsworth Epique Realty

    57 S White Rock Rd, Holmes, NY 12531
  • /50

    $619,000

    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft

    322 Old Route 22, Pawling, NY 12564

    Multi-family in Pawling! This spacious, newly remodeled 2-family home is located just a few minutes from the Village of Pawling - a great opportunity for owner-occupants, investors, or extended families! Each unit features 2 bedrooms, a full bath, living room, dining area, kitchen and bright, enclosed sunporches, providing plenty of space and natural light throughout. Inside, both units are

    Susan Stevens BHHS Hudson Valley Properties

    322 Old Route 22, Pawling, NY 12564
  • /29

    $2,500,000

    • 6 Beds
    • 6.5 Baths
    • 6,625 Sq Ft

    3302 Route 55, Pawling, NY 12564

    Welcome to your forever home, serene retreat and mini estate. Enjoy the 88 private acres with breath taking views. Mother Nature is at her best. Exceptional beauty for all four seasons. The unique and exquisite architectural design of this home lends to expansive living space, tucked behind gated entry. This home offers expansive living space, luxury and customize finishes throughout. A true

    STACI MACKIN Dixon Smith Realty

    3302 Route 55, Pawling, NY 12564
  • /42

    $775,000

    • 3 Beds
    • 2.5 Baths
    • 4,627 Sq Ft

    36 Horseshoe Path, Pawling, NY 12564

    Welcome home to the highly sought- after The Highlands in Pawling. This beautifully designed 3 BR, 3 Bath residence is tailored for today's discerning buyers, offering comfort, flexibility and effortless living. The open concept main level features an expansive Living Room, spacious Dining Room and a Chef's Kitchen , ideal for everything from Sunday pancakes to entertaining on a grand scale! The

    Neeta Saraswat Weichert Realtors

    36 Horseshoe Path, Pawling, NY 12564
  • /5

    $399,000

    • Land
    • 61.82 Acres
    • $6,454 per Acre

    0 S White Rock Rd Unit 6015368, Pawling, NY 12531

    Approved 7 lot residential subdivision: Pristine, secluded, quiet area with DCBOH approved residential building lots 3.02-6.41 acres surroundinga 31 acre open space area. All lot sites selected for privacy. Partial physical improvements (over $350K) to include 2 (partially complete) roads and storm water works in place. Tax assessments in appeal. HOA established, shared fees for roads & storm

    John Ravetto Houlihan Lawrence Inc.

    0 S White Rock Rd Unit 6015368, Pawling, NY 12531
  • /17

    $228,000

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    5 Birch Dr, Holmes, NY 12531

    2 bedroom home on Whaley Lake in Shore Haven Civic Association. Access to 3 beaches and dock. Winter (and a little summer) views of the lake.

    James Bergstraser RE/MAX Classic Realty

    5 Birch Dr, Holmes, NY 12531
  • /23

    $425,000

    • 4 Beds
    • 1.5 Baths
    • 1,776 Sq Ft

    40 Walnut St, Pawling, NY 12564

    Spacious 4 BR Home is located in the Village of Pawling. Nice property has a wonderful western view with amazing sunsets! Sunny Living Rm with picture window is open to the Dining Rm. The Kitchen has space for a breakfast table or island. The main floor has been freshly painted and has solid oak hardwood floors. Walking distance to Metro-North Train Station, Library, Medical Offices, Village

    Lisa Liffland McGrath Realty Inc

    40 Walnut St, Pawling, NY 12564
  • /24

    $485,000

    • 3 Beds
    • 3.5 Baths
    • 2,503 Sq Ft

    20 Saratoga St, Pawling, NY 12564

    Welcome to this stunning 3-bedroom, 3.5-bath end-unit townhome in the highly desirable Deerfield Ponds community. Bright, warm, and beautifully maintained, this home offers an ideal blend of comfort, convenience, and modern living. Step inside to an inviting living room that seamlessly flows into the dining area and a charming kitchen with a cozy breakfast nook, all appliances updated within the

    Julia Lear Coldwell Banker Realty

    20 Saratoga St, Pawling, NY 12564
  • /23

    $425,000

    • 2 Beds
    • 1 Bath
    • 1,130 Sq Ft

    4 Beachway Dr, Holmes, NY 12531

    Welcome to 4 Beachway Drive! This charming ranch-style home offers 2 bedrooms and lives like a 3-bedroom, with year-round views of beautiful Whaley Lake and lake access through the HOA. A welcoming front deck invites you inside, where natural light fills the home through abundant windows and skylights. The kitchen features ample cabinets and counter space, and a door leading to the back

    Regan Andrews Coldwell Banker Realty

    4 Beachway Dr, Holmes, NY 12531
  • /20

    $3,900,000

    • Land
    • 108 Acres
    • $36,111 per Acre

    57 S Quaker Hill Rd, Pawling, NY 12564

    Seldom does a property like this become available. Two parcels totaling 108 acres create the most idyllic setting on Quaker Hill. Imagine a pastoral retreat blanketed by farmed fields, well-maintained trails, and productive land. With approximately 56 cleared acres, the possibilities are endless. Build your dream country estate, an extended family compound, or an equestrian paradise with ample

    Brian McGrath McGrath Realty Inc

    57 S Quaker Hill Rd, Pawling, NY 12564
  • /16

    $387,000

    • 2 Beds
    • 2.5 Baths
    • 1,413 Sq Ft

    10 Timberline Trail, Pawling, NY 12564

    ~ Welcome to your spacious and cozy tri-level townhome in the desirable Cedar Valley Community. ~This rare end unit provides you with an abundance of light and additional outdoor space. Featuring 2 spacious bedrooms and 2.5 bathrooms, this home boasts an open and versatile layout ideal for everyday living and entertaining. The dining area and bright living room with its cozy fireplace opens

    Giorgio Palmisano Howard Hanna Rand Realty

    10 Timberline Trail, Pawling, NY 12564
  • /33

    $495,000

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

    17 Townsend Blvd, Pawling, NY 12564

    Fall in Love with this Charming Mediterranean Style Garden Home. A Private Oasis Hidden Away and Nestled among a Grove of Mature Trees. Follow meandering paths that lead to Splashes of Color from the Cultivated Perennial Gardens of a Lifetime and a Gentle Woodland Stream. This Home is Sparkling Clean, Freshly Polished, Newly Painted, Move-In Ready and awaits your Arrival. Tucked in at the end of

    Martha Woodhouse Howard Hanna Rand Realty

    17 Townsend Blvd, Pawling, NY 12564
  • /11

    $125,000

    • Land
    • 0.31 Acre
    • $403,226 per Acre

    3 Pine Dr, Pawling, NY 12564

    This property offers endless possibilities, whether for development, investment, or creating a personalized mobile home environment. Key features include: Expansive Lot: 13,500 sq ft for development, investment, or personal use.Prime Location: Close to town with shops, dining, and community events.Transportation Access: Near major routes and public transit (Dover Plains Metro North

    Brandon Doswell-Stephens Silverside Realty LLC

    3 Pine Dr, Pawling, NY 12564
  • /3

    $149,900

    • Land
    • 4.21 Acres
    • $35,606 per Acre

    0 South Rd Unit KEY853088, Pawling, NY 12531

    Beautiful 4.21-acre lot in Pawling, NY presents a unique opportunity to build your dream home. This secluded property offers the ideal blend of privacy and convenience, situated just minutes from the charming Village of Pawling, Metro-North train station, restaurants, shopping, and all the amenities the historic Hudson Valley has to offer. Only three miles off I-84. Perfect for a year-round

    Michael Knecht Howard Hanna Rand Realty

    0 South Rd Unit KEY853088, Pawling, NY 12531
  • /3

    $189,000

    • Land
    • 11.4 Acres
    • $16,579 per Acre

    0 Kirby Hill Rd, Pawling, NY 12564

    Great 11 acre BOHA property in Quaker Hill area of Pawling. Great views. Located quiet area next to historic library (not active. Shown as museum in warmer weather). Fantastic getaway area or permanent dream house.

    Richard Castro Howard Hanna Rand Realty

    0 Kirby Hill Rd, Pawling, NY 12564
  • /14

    $345,000

    • 2 Beds
    • 2.5 Baths
    • 1,567 Sq Ft

    1 Cushing Green N, Pawling, NY 12564

    This great 2 bedroom 2.5 bath townhome is a must see. Many great amenities including attached garage, formal dining room, fireplace, rear deck and more. This is a Fannie Mae HomePath property.

    Matthew Cave Hudson Property Services, LLC

    1 Cushing Green N, Pawling, NY 12564
  • /29

    $705,000

    • 4 Beds
    • 3 Baths
    • 3,888 Sq Ft

    12 Rebecca Dr, Pawling, NY 12564

    Surrounded by the natural beauty of the Hudson Valley region, this Multi-Family home benefits from a private environment that outdoor enthusiasts will find irresistible. This property's location offers convenient access to the Lakeside Park Disc Golf Course, the nearby Appalachian Trail which provides endless hiking opportunities for nature lovers and the Metro-North Railroad being about a 5

    Kevin Sanabria eRealty Advisors, Inc

    12 Rebecca Dr, Pawling, NY 12564
  • /46

    $39,000,000

    • 9 Beds
    • 15 Baths
    • 55,000 Sq Ft

    104 N Garden Dr, Pawling, NY 12564

    Welcome to Woodland Waters. Offered for the first time, this private estate is a secluded sanctuary where luxury and nature exist in perfect harmony. Over the course of five decades, the same owner has shaped and nurtured the property with remarkable care and attention, creating a setting that embodies both artistry and authenticity. With its vast landholdings, exceptional lifestyle offerings, it

    Amy Smith Sroka Julia B Fee Sothebys Int. Rlty

    104 N Garden Dr, Pawling, NY 12564
  • /19

    $990,000

    • 4 Beds
    • 3.5 Baths
    • 3,768 Sq Ft

    194 South Rd, Holmes, NY 12531

    Currently being crafted by skilled local builders, this distinguished rocking chair porch Colonial sits gracefully on more than nine private acres, offering an exceptional blend of elegance, comfort, and modern design. Once complete, the home will be bathed in natural light, showcasing gleaming hardwood floors, 9 foot ceilings, and a sophisticated chef’s kitchen appointed with recessed lighting,

    Stacey Cronin Houlihan Lawrence Inc.

    194 South Rd, Holmes, NY 12531
  • /42

    $675,000

    • 3 Beds
    • 3 Baths
    • 1,680 Sq Ft

    1098 New York 292, Holmes, NY 12531

    Here's a fantastic opportunity to own a piece of waterfront paradise, perfect for those seeking a tranquil escape without sacrificing convenience! This charming ranch-style home boasts three comfortable bedrooms and three full baths, ensuring ample space and privacy for everyone. You'll love the dedicated office, ideal for remote work, and a cozy den for a quiet reading nook while enjoying the

    John Derevjanik BHHS Hudson Valley Properties

    1098 New York 292, Holmes, NY 12531
  • /49

    $425,000

    • 2 Beds
    • 2.5 Baths
    • 1,567 Sq Ft

    13 Cushing Green S, Pawling, NY 12564

    A rare find and an incredible opportunity awaits in Squire Green with this two-story end-unit townhome featuring the highly sought-after attached garage. Townhomes are seldom available in the Squire Green section of the Deerfield Ponds community, and end units are even more uncommon, making this offering especially desirable. Steps inside reveal a spacious entry foyer leading to an updated

    Claudia Jiskra McGrath Realty Inc

    13 Cushing Green S, Pawling, NY 12564
  • /37

    $14,995,000

    • 4 Beds
    • 3.5 Baths
    • 3,942 Sq Ft

    15 Kirby Hill Rd, Pawling, NY 12564

    Kirby Hill Farm, an exceptional equestrian estate set on 247 acres of Quaker Hill's finest countryside. The turnkey, multi-discipline, equestrian facility offers 4 barns with 81 stalls, 2 indoor riding arenas, 3 outdoor riding rings, 37 paddocks, 7 additional paddocks with winterized waterers, 21 fields, polo field, over 100 acres of fenced property, and 150 acres of riding trails with direct

    Brian McGrath McGrath Realty Inc

    15 Kirby Hill Rd, Pawling, NY 12564
  • /44

    $299,900

    • 5 Beds
    • 4 Baths
    • 2,790 Sq Ft

    6 Laurel Dr, Holmes, NY 12531

    Fantastic 3-Family Opportunity in Holmes, NY!Discover the potential in this unique multifamily property, featuring a single-family home plus an additional 2-family house on one parcel. Whether you're a homeowner looking for a fixer-upper with rental income potential or an investor seeking a high-demand rental property, this is the one you’ve been waiting for. Both homes need repairs and

    Arafat Ibrahim AI Realty Brokerage LLC

    6 Laurel Dr, Holmes, NY 12531
  • /26

    $699,000

    • 3 Beds
    • 2 Baths
    • 1,822 Sq Ft

    379 S White Rock Rd, Holmes, NY 12531

    Welcome to 379 South White Rock Road — a completely renovated country home in the charming town of Pawling, NY, offering a truly distinctive blend of modern luxury and timeless rural character. Rebuilt from the foundation up in 2023, every inch of this home has been meticulously reimagined by a master builder using only premium, top-quality materials and finishes. The result is a living

    Laurence Wallace Coldwell Banker Realty

    379 S White Rock Rd, Holmes, NY 12531
  • /2

    $20,000

    • Land
    • 0.25 Acre
    • $80,000 per Acre

    0 New York 292, Holmes, NY 12531

    Looking to invest in land or future building possibilities? Great opportunity to own a .25-acre vacant lot located in an established residential area. Buyer to perform their own due diligence regarding building approvals, utilities and land use.

    Judy Lancia

    0 New York 292, Holmes, NY 12531
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