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Homes for Sale near Pawling Middle School

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  • /38

    $649,000

    $16K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,546 Sq Ft

    45 Willow Lake Dr, Holmes, NY 12531

    **Lakefront Living at Its Finest on Private Sunset Lake Just over an HOUR to NYC***Newly priced at $650,000, this beautifully maintained 3-bedroom, 2.5-bath lakefront home offers four-season living on private Sunset Lake. Located in Holmes, a hamlet of Pawling, this waterfront retreat combines peaceful surroundings, inviting indoor and outdoor spaces, and convenient access to everything the

    Agent Photo

    Heather Bragg

    River to Ridge Rlty Associates

    45 Willow Lake Dr, Holmes, NY 12531
  • /41

    $725,000

    Open Sat 12PM - 2PM $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,166 Sq Ft

    1564 Route 292, Holmes, NY 12531

    1564 Route 292 offers a rare opportunity to own a true lakefront retreat on Whaley Lake in the heart of the Hudson Valley. Set on an oversized parcel with adjacent open space that will never be built on, the property enjoys an uncommon sense of privacy and breathing room rarely found on the lake. The home underwent a major renovation and expansion in 2007, including the addition of a second-floor

    Agent Photo

    Mark Friedman

    McGrath Realty Inc

    1564 Route 292, Holmes, NY 12531
  • /50

    $1,350,000

    • 11 Beds
    • 8 Baths

    750 Route 292, Holmes, NY 12531

    Multi-generational housing opportunity with 3 distinctly different homes on one property providing 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 abundant light,

    Agent Photo

    Judith 'Judy' Albert

    BHHS Hudson Valley Properties

    750 Route 292, Holmes, NY 12531
  • /24

    $590,000

    $1K PRICE INCREASE
    • 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

    Agent Photo

    Philip Bisesto

    HomeSmart Homes & Estates

    489 Grape Hollow Rd, East Fishkill, NY 12531
  • /10

    $79,000

    $9K PRICE DROP
    • Land
    • 20,037 Sq Ft
    • $171,739 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,

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    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

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    Lot 25 Brady Brook Farm Rd, Pawling, NY 12564
  • /41

    $1,235,000

    $65K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 4,248 Sq Ft

    64 S Quaker Hill Rd, Pawling, NY 12564

    Welcome to country living at its finest. Set on 24.5 scenic acres, this classic 1910 farmhouse offers endless potential and timeless charm. A long tree-lined driveway leads to the 4 bedroom, 4 bathroom home surrounded by open fields, mature trees, and peaceful countryside views. The property includes a spacious 5-car garage (3 in front and additional 2 car tandum in back) with finished living

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    64 S Quaker Hill Rd, Pawling, NY 12564
  • /47

    $699,000

    • 3 Beds
    • 2.5 Baths
    • 1,460 Sq Ft

    21 Overlook Dr, Pawling, NY 12564

    A rare Pawling hilltop retreat with panoramic views & endless potential! Opportunities like this are extraordinarily hard to come by. Perched high to capture breathtaking, miles-long panoramic vistas, this true "sunset house" offers an idyllic Hudson Valley lifestyle centered around big skies, rolling hills, and complete tranquility. Imagine sitting on the expansive covered patio with your

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    21 Overlook Dr, Pawling, NY 12564
  • /22

    $1,350,000

    $50K PRICE INCREASE
    • 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

    Agent Photo

    Vince Buccieri

    Today Realty Corp.

    178 Charles Colman Blvd, Pawling, NY 12564
  • /40

    $375,000

    • 2 Beds
    • 1 Bath
    • 816 Sq Ft

    28 Birch Terrace, Pawling, NY 12564

    Welcome to 28 Birch Terrace, a charming 2-bedroom, 1-bath Ranch nestled on a private 0.79-acre cul-de-sac lot in the sought-after Pawling Lake Estates community. This move-in ready home features beautifully refinished hardwood floors throughout the Living Room, Dining Area, and bedrooms. The bright Kitchen offers new quartz countertops (2026), tiled floors, and a convenient washer and dryer.

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    28 Birch Terrace, 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

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    Lot 21 Cox Rd, Pawling, NY 12564
  • /43

    $575,000

    $24K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,202 Sq Ft

    17 Spring St, Pawling, NY 12564

    Welcome to 17 Spring Street, a beautifully maintained 1890 Victorian in the heart of the Village of Pawling. Rich in character and timeless charm, this inviting home features hardwood floors, crown molding, and a classic rocking chair front porch. The bright Living Room opens to an elegant Dining Room with bow windows, hardwood floors, chair rail, and a chandelier, creating the perfect setting

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    17 Spring St, Pawling, NY 12564
  • /40

    $360,000

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

    16 Evergreen Way, Pawling, NY 12564

    This immaculate, 1,413 SF 2 bedroom, 2 1/2 bath townhome sits in the highly sought-after Cedar Valley development, less than a mile from the charming Village of Pawling. Residents here enjoy a wonderful array of amenities, including a clubhouse, inground pool, and four brand-new pickleball courts, all within a community that perfectly balances privacy and convenience. Step inside to a welcoming

    Claudia Jiskra McGrath Realty Inc

    16 Evergreen Way, Pawling, NY 12564
  • /43

    $629,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,768 Sq Ft

    57 Buhleir Rd, Pawling, NY 12564

    Super Charming Cape On An Ultra Private 2.92 Acres At The Very End Of The Dead End Street! Close To Everything -- Shopping, Schools, Train Station/Commuting, Restaurants And Still Be Tucked Into Your Own Private Haven. Flexible Floor Plan To Create Rooms For You --- Big Dining Room Off The Kitchen W/ An Eat-In or a Quick Bite At The Island and a Family Room OR Living Room On The Other Side.

    Carolyn Ridenour Berkshire Hathaway HS NE Prop.

    57 Buhleir Rd, Pawling, NY 12564
  • /19

    $1,150,000

    • 5 Beds
    • 3.5 Baths
    • 3,400 Sq Ft

    Lot 5 S White Rock Rd, Holmes, NY 12531

    Introducing a stunning to-be-built farmhouse by respected local builders known for exceptional craftsmanship, thoughtful design, and quality construction. Perfectly positioned on more than 11 private acres, this custom home blends timeless farmhouse charm with modern comfort, offering a peaceful retreat in one of the Hudson Valley's most desirable settings.Designed with today's lifestyle in

    Stacey Cronin Houlihan Lawrence Inc.

    Lot 5 S White Rock Rd, Holmes, NY 12531
  • /45

    $600,000

    Open Sun 1PM - 3PM
    • 4 Beds
    • 2.5 Baths
    • 2,924 Sq Ft

    5 Red Tail Ct, Pawling, NY 12564

    Space, style, and convenience come together in this beautiful Squire Green home. Featuring a brand-new kitchen with granite countertops, gas stove and stainless steel appliances, spacious living areas, a cozy fireplace, and oversized bedrooms. Need space? This home delivers. The home continues to impress with a large unfinished basement offering endless potential for additional living space.

    Susan Salamone Houlihan Lawrence Inc.

    5 Red Tail Ct, Pawling, NY 12564
  • /50

    $729,999

    Open House 8/15
    • 3 Beds
    • 3 Baths
    • 2,659 Sq Ft

    6 Overlook Rd, Pawling, NY 12564

    Experience comfort, convenience, and accessibility in this beautifully designed 3-bedroom, 2,659 square foot home situated on 1.3 private acres. Thoughtfully equipped with accessible features throughout, this home offers both functionality and luxury. The primary living space is conveniently located on the main floor with a partially finished full basement, with a pellet stove, which connects to

    Jarrod Lecceardone Listing by Village Realty

    6 Overlook Rd, Pawling, NY 12564
  • /16

    $216,000

    $109K PRICE DROP
    • 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
  • /46

    $469,900

    $30K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,560 Sq Ft

    23 Lakeview Dr, Holmes, NY 12531

    Well maintained raised ranch offering 4 bedrooms and 2 bathrooms. This inviting home features spacious bedrooms, hardwood floors, and a bright living room filled with natural light. The finished lower level provides additional living space and laundry room, perfect for guests, a home office, or recreation. Sliding doors from the dining room lead to a deck overlooking a spacious backyard, ideal

    Silvia Delgado Keller Williams Realty Partner

    23 Lakeview Dr, Holmes, NY 12531
  • /33

    $749,900

    • 4 Beds
    • 3.5 Baths
    • 3,236 Sq Ft

    26 E Forest Trail, Holmes, NY 12531

    Nestled on 2.01 private acres, this beautifully maintained Colonial offers the perfect blend of timeless elegance, modern comfort, and exceptional convenience, just minutes from the Putnam County border, Interstate 84, and the Metro-North Railroad for an easy commute. Built in 2001, this move-in ready home features four spacious bedrooms, three full bathrooms, and one half bathroom, highlighted

    John Oliveira Douglas Elliman Real Estate

    26 E Forest Trail, Holmes, NY 12531
  • /31

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft

    358 Route 292, Holmes, NY 12531

    Pure perfection!This beautifully and fully renovated 3-bedroom, 2-full-bath home offers modern luxury and total peace of mind. Step inside to an open, sun-drenched living space featuring high ceilings and gleaming hardwood floors throughout. The stunning kitchen boasts sleek quartz countertops, stainless steel appliances, and a spacious pantry for all your storage needs. Convenience is key

    LUCIANA BENNETT McGrath Realty Inc

    358 Route 292, Holmes, NY 12531
  • /45

    $1,475,000

    • 4 Beds
    • 4.5 Baths
    • 7,210 Sq Ft

    7 Herd and Tanner Rd, Holmes, NY 12531

    **Do not walk or go to the property without an agent**Set privately on more than 22 acres just minutes from the quaint Village of Pawling, this exceptional country estate captures the essence of Hudson Valley living with breathtaking mountain views, extraordinary privacy, and timeless elegance. Designed for both sophisticated entertaining and comfortable everyday living, this exquisite Colonial

    Stacey Cronin Houlihan Lawrence Inc.

    7 Herd and Tanner Rd, Holmes, NY 12531
  • /8

    $1,250,000

    • 5 Beds
    • 4.5 Baths
    • 3,920 Sq Ft

    120 Harmony Rd, Pawling, NY 12564

    New construction 4 bedroom, 4.5 bathroom home on 5 acres. Don't miss this opportunity to customize your dream home. This home features a open floor plan with large kitchen, perfect for entertaining. The main living area has exposed beams and high ceilings. The primary bedroom has large walk in closet and ensuite. There is also a junior suite with ensuite. See attached floor plans for full detail.

    Bliss Voutsinas Hillside Realty & Development

    120 Harmony Rd, Pawling, NY 12564
  • /50

    $725,000

    • 2 Beds
    • 2 Baths
    • 1,722 Sq Ft

    1080 Route 292, Holmes, NY 12531

    Step into this charming lakefront cottage and immediately feel at home. The foyer leads to the primary bedroom, featuring a full bath and breathtaking views of Whaley Lake. A second bedroom and a full hallway bath complete the main level. Upstairs, a loft offers another perspective of the serene lake, perfect for reading, relaxing, or watching the sunset. The open-concept kitchen flows into the

    Peggy MacLeay-Generoso McGrath Realty Inc

    1080 Route 292, Holmes, NY 12531
  • /50

    $2,790,000

    • 4 Beds
    • 3.5 Baths

    5 Mccarthy Rd, Holmes, NY 12531

    Nestled in a tranquil and picturesque setting, this exceptional equestrian facility offers everything a rider could desire, along with a beautiful home to live in. Spanning 21 acres of mostly open land, the property features expansive pastures enclosed by charming 3-board post and rail fencing. Equestrian amenities include a main barn with 8 spacious 12x12 stalls, each with individual water, a

    Shaylene Neumann Houlihan Lawrence Inc.

    5 Mccarthy Rd, Holmes, NY 12531
  • /4

    $260,000

    • Land
    • 11.49 Acres
    • $22,628 per Acre

    Lot 5 S White Rock Rd, Holmes, NY 12531

    Build Your Dream Estate in the Heart of the Hudson Valley-Lot 5Set amidst the natural beauty of the Hudson Valley, this exceptional 11+ acre residential parcel offers a rare opportunity to create a private luxury retreat just 75 minutes from New York City. Ideally situated between the village of Pawling and Sherman, CT, the property combines peaceful country living with convenient access to

    Stacey Cronin Houlihan Lawrence Inc.

    Lot 5 S White Rock Rd, Holmes, NY 12531
  • /17

    $364,900

    $54K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    11 Park Ln, Holmes, NY 12531

    Town of Pawling! Looking for a great starter home with privacy? This 3 Bedroom, 1 Bath Raised Ranch located on .58 acres at end of a private road is for you! Commuter's Dream! Close to I-84! Open floor plan with hardwood flooring in living room & dining room, large kitchen with plenty of counter & cabinet space. Large family room on lower level with sliding door to yard. Sold as-is. Buyer to pay

    Ernie Acampora River Realty Services, Inc.

    11 Park Ln, Holmes, NY 12531
  • /6

    $17,995

    • Land
    • 10,890 Sq Ft
    • $71,980 per Acre

    0 New York 292, Holmes, NY 12531

    Opportunity awaits on Route 292 in Holmes, NY. This .25-acre vacant lot is located in an established area of Pawling with convenient access to local roads, schools, and nearby amenities. Property is being sold as-is, and buyers should perform their own due diligence regarding BOHA approval, utilities, zoning, permits, and intended use. A great entry-level land opportunity in Dutchess County at an

    Ocie Collins KW MidHudson

    0 New York 292, Holmes, NY 12531
  • /8

    $619,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,652 Sq Ft

    0 Prospect St Unit KEY1024161, Pawling, NY 12564

    TO BE BUILT – Build your dream home in the charming Village of Pawling! Ideally located just minutes from downtown Pawling, you'll enjoy convenient access to local shops, restaurants, schools, parks, and the Metro-North train station, making commuting and everyday living a breeze. The homesite is serviced by municipal water and sewer, offering added convenience and peace of mind. Pricing and

    Molly Roche eXp Realty

    0 Prospect St Unit KEY1024161, Pawling, NY 12564
  • /7

    $249,000

    Coming Soon
    • 1 Bed
    • 1 Bath
    • 733 Sq Ft

    1555 Route 292, Holmes, NY 12531

    Attention investors, contractors, and DIYers looking for affordable lake living - this one may be just what you are looking for! Welcome to this charming 1-bedroom, 1-bath cottage-style home in Holmes, offering a unique opportunity to enjoy lake access and views of Whaley Lake. Located directly across the street from the lake, this 733 sq ft home provides lake rights and convenient access to the

    Virginia Corbett eXp Realty

    1555 Route 292, Holmes, NY 12531
  • /46

    $1,799,000

    Open Sun 12PM - 2PM
    • 5 Beds
    • 5.5 Baths
    • 5,390 Sq Ft

    41 and 43 Meeting House Rd, Pawling, NY 12564

    Rare 5-Acre Quaker Hill Estate with Guest Cottage: Discover the ultimate sanctuary at the crest of Quaker Hill, where 43 Meeting House Road stands as a testament to refined country living. Situated on a lush 5-acre parcel and set well back from a scenic country road, this estate offers a rare degree of privacy and tranquility, surrounded by sweeping meadows, historic horse farms and prestigious

    Richard Esman Douglas Elliman Real Estate

    41 and 43 Meeting House Rd, Pawling, NY 12564
  • /56

    $3,100,000

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

    809 N Quaker Hill Rd, Pawling, NY 12564

    Farm Nord is a meticulously restored country estate, originally established in the 1700s as a dairy farm by the renowned Taber family of Rhode Island. The Tabers were stewards of the estate for five generations and two centuries, with only a few families since carrying on its legacy. The property's idyllic 12 acres are peppered with endless stone walls, several-hundred-year-old trees, and rolling

    Raj Kumar Four Seasons Sotheby's Int.

    809 N Quaker Hill Rd, Pawling, NY 12564
  • /50

    $525,000

    $74K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 900 Sq Ft

    1616 Route 292 Unit Cottage 12, Holmes, NY 12531

    $74K PRICE IMPROVEMENT!! Welcome to one of the Hudson Valley's most extraordinary hidden treasures—a private island retreat nestled in the heart of Whaley Lake, where every day feels like a vacation and every arrival feels like an escape from the ordinary. Accessible only by boat, this remarkable waterfront residence offers an exceptionally rare opportunity to own a piece of paradise within an

    Julie Conner eXp Realty

    1616 Route 292 Unit Cottage 12, Holmes, NY 12531
  • /17

    $990,000

    New Construction
    • 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
  • /44

    $879,800

    • 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 is 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

    $5,000,000

    • 8 Beds
    • 13 Baths
    • 15,000 Sq Ft

    618 Quaker Hill Rd, Pawling, NY 12564

    Set high atop the storied crest of Quaker Hill, Elmwood Farm is a legacy estate where Hudson Valley history, architectural grandeur, and pastoral beauty converge. Approached by a long, winding gated drive, the property reveals itself gradually across 25.5 rolling acres before arriving at a striking Elizabethan style manor that has stood watch over the surrounding countryside for generations.

    Jake Garay Serhant LLC

    618 Quaker Hill Rd, 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
  • /12

    $300,000

    $25K PRICE DROP
    • Land
    • 4.36 Acres
    • $68,792 per Acre

    576 Holmes Rd, Holmes, NY 12531

    Positioned at the intersection of Route 52 and Holmes Road, directly across from Milltown Road, this exceptional offering presents two commercial parcels totaling 4.361 acres, comprised of 3.19 acres and 1.171 acres. With a NYS DOT annual average daily traffic count of 5,415 on Route 52, the property benefits from steady visibility and strong exposure, making it an ideal setting for a wide range

    Claudia Jiskra McGrath Realty Inc

    576 Holmes Rd, Holmes, NY 12531
  • /33

    $9,750,000

    $7M PRICE DROP
    • 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

    Shaylene Neumann Houlihan Lawrence Inc.

    225 Route 22, Pawling, NY 12564
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