39

Talbot County MD Houses for Sale with Private Pool

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  • /44

    $1,950,000

    • 3 Beds
    • 4 Baths
    • 2,568 Sq Ft

    6119 Country Club Dr, Easton, MD 21601

    Location, Location, Location!!! This recently renovated waterfront rancher on a 2+ acre, park-like lot is conveniently located next to Talbot Country Club, and off the Oxford Road corridor. This home features 3 bedrooms, 2 full and 2 - 1/2 baths, a large living room with fireplace, kitchen/family room combo with the kitchen featuring quartz counter tops, stainless steel appliances and custom

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 941-0437

    6119 Country Club Dr, Easton, MD 21601
  • /61

    $795,000

    • 4 Beds
    • 2.5 Baths
    • 3,120 Sq Ft

    8445 Gannon Cir, Easton, MD 21601

    Motivated Seller - Price Improvement! 4-Bedroom Beauty on Over an Acre. This freshly painted home offers 3,120 sq. ft. of living space on 1+ acre, boasting 4 spacious bedrooms, an office/bonus room and more than 25 upgrades you’ll have to see to believe. Step inside to find granite countertops, crown molding, and cathedral ceilings that create an airy, upscale feel. Out back, relax under the

    Agent Photo

    Lona Todd

    Taylor Properties

    (410) 873-7389

    8445 Gannon Cir, Easton, MD 21601
  • /31

    $399,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    6135 Summit St, Tilghman, MD 21671

    Welcome to your Eastern Shore getaway, located at 6135 Summit Street, Tilghman, Maryland. This charming property is just a short walk from Tilghman Island's best waterfront attractions, including two marinas and three excellent dining options. This two-bedroom, one-bath home reflects pride of ownership and has been well maintained, making it ready for you to enjoy a slower pace of life on

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 593-3451

    6135 Summit St, Tilghman, MD 21671
  • /80

    $1,350,000

    • 4 Beds
    • 3.5 Baths
    • 4,443 Sq Ft

    28028 Playtor Rd, Easton, MD 21601

    Welcome to this stunning William Poole-designed Tidewater Colonial, nestled on approximately 2.3 acres in the serene neighborhood of Waverly Island Estates, just three miles from the vibrant Town of Easton. This exceptional property blends classic architecture with modern amenities, offering a peaceful retreat on the Eastern Shore of Maryland.Step inside to discover a thoughtfully

    Coard Benson Benson & Mangold, LLC

    28028 Playtor Rd, Easton, MD 21601
  • /41

    $1,695,000 Open Sun 11AM - 1PM

    • 5 Beds
    • 3.5 Baths
    • 4,102 Sq Ft

    9171 Deepwater Point Rd, Saint Michaels, MD 21663

    Welcome to Saint Micheals Retreat, an extraordinary 6+/- acre property overlooking the Links at Perry Cabin Golf Course with direct water access to Long Haul Creek and Miles River. Just moments to downtown Saint Michaels, fine dining, shopping, and entertainment, this stunning makeover offers 4,100 +/- sq. ft. of single-story living designed for endless indoor/outdoor entertainment. This

    Craig Linthicum Benson & Mangold, LLC

    9171 Deepwater Point Rd, Saint Michaels, MD 21663
  • /39

    $3,275,000

    • 7 Beds
    • 10 Baths
    • 7,077 Sq Ft

    28092 Glebe Rd, Easton, MD 21601

    Miles Away on Murphy’s Point – Discover an unparalleled waterfront retreat at 28092 Glebe Rd, Easton, MD, nestled on approximately ±2.7 picturesque acres. Thoughtfully designed for entertaining, relaxation, and convenient living, this luxurious estate offers expansive indoor and outdoor spaces, exceptional waterfront amenities, and easy access to nearby towns, beaches, and metropolitan

    Coard Benson Benson & Mangold, LLC

    28092 Glebe Rd, Easton, MD 21601
  • /91

    $8,750,000

    • 6 Beds
    • 6 Baths
    • 9,566 Sq Ft

    27295 Southside Island Creek Rd, Trappe, MD 21673

    Wilderness Estate- REVISED OFFERING INCLUDES 5 PARCELS 6.27.25- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 234 acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved

    Coard Benson Benson & Mangold, LLC

    27295 Southside Island Creek Rd, Trappe, MD 21673
  • /71

    $9,900,000

    • 5 Beds
    • 6 Baths
    • 14,935 Sq Ft

    6010 Shipyard Ln, Easton, MD 21601

    Situated on one of the finest residential parcels in the country, Ship’s Point, is an estate with few rivals anywhere, at any price. The completely private 13+/- acre estate includes a deep water pier, and 270-degree views at the confluence of Trippe’s Creek and the Tred Avon River. The south-west facing manor house has been meticulously renovated by renowned builder Winchester Construction. A

    Chuck Mangold Benson & Mangold, LLC

    6010 Shipyard Ln, Easton, MD 21601
  • /47

    $549,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 2,226 Sq Ft

    11561 Woodwinds Ct, Cordova, MD 21625

    Mortgage savings may be available for buyers of this listing. Tucked away at the end of a long private driveway, this beautifully maintained 4-bedroom, 3.5-bath contemporary-style home offers rare privacy on over two acres in the sought-after Chapel District of Talbot County, just minutes from Easton and Route 50 for easy commuting. Surrounded by mature trees and landscaped grounds, this

    Barbara McCaffrey Redfin Corp

    11561 Woodwinds Ct, Cordova, MD 21625
  • /53

    $6,450,000

    • 6 Beds
    • 8 Baths
    • 9,595 Sq Ft

    11977 Billys Point Ln, Easton, MD 21601

    Welcome to Henry’s Retreat, an extraordinary 37-acre waterfront estate overlooking Quarter Cove off the Wye River. Offering over 2,700 feet of shoreline, this stunning property ensures ultimate privacy, breathtaking views, and unforgettable sunsets.Built in 2016, the 8,835 sq. ft. main residence is designed for luxurious living and seamless entertaining, featuring five bedrooms, six full

    Laura Carney TTR Sotheby's International Realty

    11977 Billys Point Ln, Easton, MD 21601
  • /133

    $3,650,000

    • 4 Beds
    • 4.5 Baths
    • 3,868 Sq Ft

    4500 Boone Creek Rd, Oxford, MD 21654

    Welcome to your private Eastern Shore retreat! This amazing 4-bedroom, 4.5-bath Cape Cod is perfectly situated on a secluded peninsula, offering unparalleled tranquility and breathtaking waterfront views of Boone Creek located in beautiful Oxford, Maryland. The home offers an incredible blend of traditional elegance and modern luxury. An open and airy floor plan is bathed in natural light, with

    Lisa Lynch Keller Williams Realty

    4500 Boone Creek Rd, Oxford, MD 21654
  • /69

    $3,250,000

    • 5 Beds
    • 5.5 Baths
    • 4,602 Sq Ft

    5440 Ferry Neck Rd, Royal Oak, MD 21662

    Welcome to ‘Drake’s Landing’! Beautifully sited on 20 picturesque acres on the shores of Irish Creek, this 4,602 sq. ft .completely renovated (2021) waterfront estate offers the perfect blend of casual elegance and thoughtful design. The main level welcomes with expansive water views and features a guest bedroom with ensuite bath, a cozy family room (or den/office), and a gracious living room

    Laura Carney TTR Sotheby's International Realty

    5440 Ferry Neck Rd, Royal Oak, MD 21662
  • /45

    $4,750,000

    • 5 Beds
    • 7 Baths
    • 5,554 Sq Ft

    21721 Heavenly Haven Rd, Sherwood, MD 21665

    This remarkable property has it all. Private 15 plus acres. Beautiful views overlooking Dunn's Cove sunrises. A shore sportsman's dream. Partially wooded, fields of crops, hunting blind and a pier for your fishing vessel. This was a large compound with the Main house, in-law wing and a separate 2 BR guest house w/fireplace and large screened porch. Waterside in-ground pool and children's play

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    21721 Heavenly Haven Rd, Sherwood, MD 21665
  • /109

    $8,875,000

    • 7 Beds
    • 7.5 Baths
    • 10,240 Sq Ft

    10770 Rich Neck Rd, Claiborne, MD 21624

    Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen

    Robert G. Shannahan Shoreline Realty

    10770 Rich Neck Rd, Claiborne, MD 21624
  • /57

    $2,295,000

    • 3 Beds
    • 5 Baths
    • 3,099 Sq Ft

    8320 Ingleton Cir, Easton, MD 21601

    Nestled along the Miles River with westerly sunset views, this exceptional house offers a blend of modern comfort and classic Eastern Shore charm. Boasting sweeping views of St. Michaels, this home features an expansive open floor plan designed for seamless indoor-outdoor living. Step inside to find a sun-drenched great room creating the perfect setting for both quiet relaxation and lively

    Jim Corson Benson & Mangold, LLC

    8320 Ingleton Cir, Easton, MD 21601
  • /109

    $2,650,000

    • 4 Beds
    • 5 Baths
    • 5,207 Sq Ft

    26090 Royal Oak Rd, Easton, MD 21601

    This house is a showstopper! A work of art that feels part castle, part cathedral! Pictures don't do it justice! It's a unique, historic, waterfront estate that combines privacy & nature & excellent location on Oak Creek between St. Michaels & Easton. The treelined drive welcomes you to this one of a kind home built in 1890 and situated on 11.59 acres. Featuring stained glass transoms, the

    Kate Koeppen Chesapeake Bay Real Estate Plus, LLC

    26090 Royal Oak Rd, Easton, MD 21601
  • /52

    $2,700,000

    • 3 Beds
    • 3 Baths
    • 7,949 Sq Ft

    6976 Travelers Rest Cir, Easton, MD 21601

    Welcome to Soleil on the Bay! Nestled on nearly 7 acres along the scenic Maxmore Creek—just off the Tred Avon River—this exceptional west-facing waterfront property offers the most gorgeous sunsets providing the perfect blend of privacy, natural beauty, and endless potential. Ideally located between Easton and St. Michaels, it provides easy access to the best of Maryland’s Eastern Shore.Enter

    Clifford Meredith Meredith Fine Properties

    6976 Travelers Rest Cir, Easton, MD 21601
  • /64

    $1,399,000

    • 3 Beds
    • 3 Baths
    • 3,853 Sq Ft

    6670 Tilghman Island Rd, Sherwood, MD 21665

    Waterfront home situated on Back Creek in Sherwood, offering direct access to the Chesapeake Bay and Choptank Rivers. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed lighting.

    Larry Brennan TTR Sotheby's International Realty

    6670 Tilghman Island Rd, Sherwood, MD 21665
  • /45

    $749,900

    • 3 Beds
    • 3 Baths
    • 2,660 Sq Ft

    4957 Bar Neck Rd, Tilghman, MD 21671

    Secure and Secluded Luxury Living with Bay Views & Resort-Style BackyardProperty is located in FEMA Zone X, has never had water on the property and seller is not required to have flood insuranceTucked away at the end of a private Crepe Myrtle-lined drive, this well-maintained luxury retreat offers the perfect blend of tranquility, style, and function—without the constraints of an HOA.

    Danny Martin Keller Williams Flagship

    4957 Bar Neck Rd, Tilghman, MD 21671
  • /86

    $7,500,000

    • 5 Beds
    • 6 Baths
    • 10,000 Sq Ft

    7090 Cooper Point Rd, Bozman, MD 21612

    Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design.The custom brick exterior is crowned

    Laura Carney TTR Sotheby's International Realty

    7090 Cooper Point Rd, Bozman, MD 21612
  • /138

    $8,400,000

    • 7 Beds
    • 8 Baths
    • 8,001 Sq Ft

    26546 Presquile Dr N, Easton, MD 21601

    Presquile Manor House, originally built by the Lloyd Family circa 1800 as one of their three Plantation Houses, sits up high on the Wye River with due West Exposure. The Main House has recently gone through a two-year renovation process from top to bottom by West & Callahan Construction and Peter Zimmerman Architects Inc, with much thought and care to keep all of the historic attributes that

    Henry Gibbons-Neff Meredith Fine Properties

    26546 Presquile Dr N, Easton, MD 21601
  • /50

    $13,750,000

    • 5 Beds
    • 9 Baths
    • 13,228 Sq Ft

    27772 Sharp Rd, Easton, MD 21601

    Stock Range Farm spans 350 acres of prime waterfront and is available for purchase in its entirety or with reduced acreage including the main residence, if the buyer so chooses. The property is free of easements and includes development rights, subject to all applicable Talbot County zoning regulations.With vast working farmland and resort-style amenities, this rare gem truly combines

    Laura Carney TTR Sotheby's International Realty

    27772 Sharp Rd, Easton, MD 21601
  • /39

    $475,000

    • 4 Beds
    • 4 Baths
    • 3,024 Sq Ft

    32115 Park Ave, Queen Anne, MD 21657

    Discover a truly unique opportunity in the picturesque town of Queen Anne with this enchanting Victorian gem. Offering over 3,000 sq. ft. of thoughtfully updated living space on just over an acre, this home combines timeless character with modern functionality. The property includes a spacious detached shop and a 2-car detached garage—providing ample room to grow, create, and savor the charm of

    Amanda Morgan Brenton Realty Group

    32115 Park Ave, Queen Anne, MD 21657
  • /21

    $405,000

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    8535 Colony Cir, Easton, MD 21601

    Exceptional home with many fine features and updates: new roof, encapsulated crawl space, new A/C upstairs, new fence, pool filter and updated master bath. The interior offers living room, separate dining room, family room with fireplace plus 3 beautiful bedrooms, large deck with retractable awning and a refreshing inground pool. The shed with electric completes the package. Light bright and

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    8535 Colony Cir, Easton, MD 21601
  • /61

    $750,000

    • 5 Beds
    • 3.5 Baths
    • 2,306 Sq Ft

    26698 Arcadia Shores Rd, Easton, MD 21601

    Charming 4-Bedroom Cape Cod on 4 Private Acres with Pool & Sunroom!Welcome to your dream retreat! This beautifully maintained Cape Cod offers 4 spacious bedrooms and 3.5 baths, set on a serene 4-acre lot. Enjoy summer days by the in-ground pool, or unwind in the sunny, four-season sunroom. The inviting living room features a cozy wood stove—perfect for cool evenings. The expansive primary

    Becky Wibberley Coldwell Banker Realty

    26698 Arcadia Shores Rd, Easton, MD 21601
  • /56

    $775,000

    • 3 Beds
    • 3 Baths
    • 2,703 Sq Ft

    29414 Andrew Ln, Easton, MD 21601

    NEW **SELLER IS OFFERING A $25,000 BUYER CREDIT TOWARDS UPDATING**PARK LIKE SETTING- MATURE TREES- CREEK- BRIDGE ALL ON 3.064 PRIVATE ACRES*** Meticulously Maintained 3 bedroom, 3 bath home, With Den/Office, Bonus Room or Possible in-law/Au Pair Suite with Wheelchair access doors and a Chairlift for easy upstairs living access. Private in ground Pool with Gazebo. Woods in back half

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    29414 Andrew Ln, Easton, MD 21601
  • /74

    $1,125,000

    • 4 Beds
    • 2.5 Baths
    • 2,553 Sq Ft

    205 S Hanson St, Easton, MD 21601

    Nestled in the heart of Easton’s Historic District, 205 S Hanson Street is a beautifully preserved early-20th-century home that exudes timeless charm and sophistication. Built around 1910, this elegant Colonial Revival offers approximately 2,520 square feet of refined living space with original hardwood floors, detailed millwork, and gracious proportions that reflect its rich architectural

    Derek Blazer Cummings & Co. Realtors

    205 S Hanson St, Easton, MD 21601
  • /130

    $11,500,000

    • 4 Beds
    • 3 Baths
    • 9,833 Sq Ft

    29031 Howell Point Rd, Trappe, MD 21673

    Currently one of the largest Farm/Residential Estates available in the State of Maryland and a once in a lifetime opportunity to own it. This 662+ acres waterfront property with 1.8 miles of shoreline known as "Middleville" circa 1880 is truly a magnificent landholding. Located in Talbot County the property is improved with 5 Residents. A newly renovated Main Home that boasts Tidewater Colonial

    Jay Phillips Holiday Real Estate

    29031 Howell Point Rd, Trappe, MD 21673
  • /81

    $1,295,000

    • 5 Beds
    • 4.5 Baths
    • 7,166 Sq Ft

    13543 Rustling Oaks Dr, Wye Mills, MD 21679

    Five diamond resort living meets the Eastern Shore in a relaxed rural setting. This exquisite one-of-a-kind home is situated on just under an acre enveloped by luscious, manicured landscaping, towering pines and open field. Just minutes away provides boating with Wye River Landing, a large public boat ramp. Add the luxury of marina life just miles away at Kent Narrows, St Michaels, and Oxford.

    Judy Moore Benson & Mangold, LLC

    13543 Rustling Oaks Dr, Wye Mills, MD 21679
  • /48

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft

    719 Elizabeth St, Easton, MD 21601

    First time available in over 40 years, this lovingly maintained residence offers an abundance of features. Step into a welcoming atmosphere that includes both a den and living room, each with its own fireplace—one gas and one wood-burning—perfect for cozy evenings.Enjoy meals in the separate dining room, and benefit from a full bath conveniently located on the main level. The standout feature is

    Mary Haddaway Benson & Mangold, LLC

    719 Elizabeth St, Easton, MD 21601
  • /29

    $799,000

    • 4 Beds
    • 2 Baths
    • 2,208 Sq Ft

    10118 Hiners Ln, Easton, MD 21601

    Beautiful 4-bedroom, 2-bathroom home on a 1+/- acre parcel with an additional 12.45+/- acre lot included—ideal for expansion, equipment storage, or future investment. The 48' x 60' pole barn features three overhead doors, providing ample space for tools, vehicles, and materials. Outside, enjoy an in-ground pool and a fully fenced backyard. The property is currently served by well and septic, but

    Alicia Gannon Dulin Benson & Mangold, LLC

    10118 Hiners Ln, Easton, MD 21601
  • /60

    $8,495,000

    • 6 Beds
    • 11 Baths
    • 17,402 Sq Ft

    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663

    NEW PRICE! Located minutes from downtown St. Michaels, “Aqua Vitae” the waters of life, sits on 8.6 private acres on Harris Creek, a Chesapeake Bay tributary. This custom-built offering w/ over 400’ of direct water frontage is comprised of 3 magnificent structures: a grand main residence, guest cottage, & “party barn” all highlighted by a waterside pool, pier w/ 4’ MLW, pine grove, putting green,

    Doc Keane Washington Fine Properties, LLC

    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
  • /73

    $749,000

    • 4 Beds
    • 2.5 Baths
    • 2,512 Sq Ft

    22 Londonderry Dr, Easton, MD 21601

    Turnkey and ready to go in Thredhaven! 4 Br 2 1/2 Ba with first floor master suite, pool and 2 car attached garage with finished upstairs bonus room. Owners have installed new flagstone pavers, new built ins around the fireplace, remodeled the kitchen, new carpet and added recessed lighting in the entire house. This is an excellent location in downtown Easton!

    Henry Gibbons-Neff Meredith Fine Properties

    22 Londonderry Dr, Easton, MD 21601
  • /45

    $3,500,000

    • 3 Beds
    • 5 Baths
    • 4,305 Sq Ft

    6906 Travelers Rest Cir, Easton, MD 21601

    This expansive 3-bedroom, 5-bathroom contemporary home is nestled on over 4 acres along the picturesque Tred Avon River. Ideally situated between Easton and St. Michaels, this property offers the perfect blend of privacy and convenience. Featuring an open floorplan with soaring cathedral ceilings, it’s designed for both comfort and style. Additional features include a spacious primary suite

    Clifford Meredith Meredith Fine Properties

    6906 Travelers Rest Cir, Easton, MD 21601
  • /40

    $629,000

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    204 E Marengo St, Saint Michaels, MD 21663

    Coastal charm meets small-town living in this beautifully updated cottage, just one block from the Historic District and 1.5 blocks from water access, including a marina and boat ramp, and downtown Saint Michaels! This home exudes a true vacation vibe, offering main-level living with sun-filled spaces designed for relaxation. The completely remodeled full bathroom adds modern comfort, while the

    Jennifer Chino Compass

    204 E Marengo St, Saint Michaels, MD 21663
  • /42

    $4,495,000

    • 4 Beds
    • 5.5 Baths
    • 5,062 Sq Ft

    27029 Miles River Rd, Easton, MD 21601

    Irish Tides offers a quintessential Eastern Shore retreat with luxury and style. This beautifully crafted4-bedroom, 5.5-bath main house provides captivating views of the Miles River from almost every room. The main level has been enhanced with a new HVAC system and ductwork, ensuring comfort andefficiency throughout. Exquisite crown moldings, hardwood floors, and custom built-ins add an

    Chuck Mangold Benson & Mangold, LLC

    27029 Miles River Rd, Easton, MD 21601
  • /20

    $3,495,000 New Construction

    • 4 Beds
    • 4.5 Baths

    25826 Orchard Terrace, Royal Oak, MD 21662

    Buildable 1.6 +/- acre lot ready for your vision and a builder ready to help you make it a reality! Over 500 ft of shoreline on the Tred Avon River. Close to the public park/playground and just a short boat ride or ferry ride to Oxford. Centrally located between Easton and St Michaels. Just minutes to Talbot County's favorite waterfront towns by car, bike, or boat.

    Chuck Mangold Benson & Mangold, LLC

    25826 Orchard Terrace, Royal Oak, MD 21662
  • /11

    $1,235,000 New Construction

    • 4 Beds
    • 2.5 Baths

    25832 Turner Ave, Royal Oak, MD 21662

    Centrally located between Easton and St Michaels and just a stone’s throw from the Oxford Bellevue Ferry on the Tred Avon, one of Talbot County’s premier waterfront communities with 13 half acre to 1.5 acre home sites. The community features its own private beach and kayak launch with nearby public park with playground and marina. Just minutes to Talbot County's favorite waterfront towns by car,

    Chuck Mangold Benson & Mangold, LLC

    25832 Turner Ave, Royal Oak, MD 21662
  • /50

    $8,025,000

    • 6 Beds
    • 12 Baths
    • 24,767 Sq Ft

    5369 Morgans Point Dr, Oxford, MD 21654

    Available for private agreement at auction price. This masterpiece of luxury living is set on nearly 7 acres along the picturesque Tred Avon River. The centerpiece is a magnificent 3-level palatial brick home with 6 bedrooms, 7 full baths, 5 half baths, and 7 gas fireplaces. Enjoy the private dock boasting 4 feet of mean low water (MLW), complete with 2 boat lifts, 4 jet ski lifts, and a

    Clifford Meredith Meredith Fine Properties

    5369 Morgans Point Dr, Oxford, MD 21654
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