59

Homes for Sale near Sudlersville Middle School

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  • /42

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft

    134 Char Nor Manor Blvd, Chestertown, MD 21620

    Chester River Charm: Your Gateway toEastern Shore LivingCompletely Renovated Cottage with River Views & Endless PossibilitiesDiscover the perfect blend of modern comfort and Eastern Shore tranquility at this beautifullytransformed 3-bedroom, 1-bath cottage just minutes from historic Chestertown and the pristineChester River. Whether you're seeking a weekend escape, investment

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 282-1137

    134 Char Nor Manor Blvd, Chestertown, MD 21620
  • /30

    $1,198,000

    • 5 Beds
    • 3.5 Baths
    • 3,640 Sq Ft

    300 Hickory Ln, Chestertown, MD 21620

    Welcome to Pheasantfield Farm, a 21- acre equestrian estate beautifully nestled on the Chester River. Fantastic location, ample privacy, and yet only a short drive, or boat ride, to historic Chestertown. The main home boasts 4 bedrooms and two and a half baths. The primary bedroom has a lovely view of the river, two walk-in closets and a large attached full bath. The spacious

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 936-6289

    300 Hickory Ln, Chestertown, MD 21620
  • /51

    $465,000

    • 3 Beds
    • 2.5 Baths
    • 2,184 Sq Ft

    218 Lakeside Dr, Millington, MD 21651

    Charming Colonial in the highly desirable community of Springview. A neighborhood with large lots, beautiful homes and properties rarely for sale. Tucked away in Upper Queen Anne's County in Millington, Maryland you're conveniently located to head to Kent County, Kent Island or Delaware. This two story is the perfect blend of traditional meets cozy so you'll feel right at home!! Wood burning

    Crystal Smith RE/MAX Executive

    218 Lakeside Dr, Millington, MD 21651
  • /46

    $449,000

    • 3 Beds
    • 3 Baths
    • 3,096 Sq Ft

    201 Boundary Ave, Chestertown, MD 21620

    Discover this spacious home offering 3,100 sq ft of living space on a 1⁄2 acre lot with deeded access to the Chester River. Generously sized rooms and an inviting floor plan create an ideal setting for both everyday living and entertaining. The main level bedroom features a recently remodeled bath and large walk in closet. Enjoy the natural light and tranquil views from the sunroom, perfect for

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    201 Boundary Ave, Chestertown, MD 21620
  • /59

    $475,000

    • 4 Beds
    • 2.5 Baths
    • 2,258 Sq Ft

    165 Char Nor Manor Blvd, Chestertown, MD 21620

    Chester River Views from Every Angle!Welcome to this stunning Colonial located on the Queen Anne’s County side of Chestertown, offering unmatched views of the Chester River and serene waterfront living.This spacious home features 4 large bedrooms, 2.5 bathrooms, and gorgeous hardwood floors throughout. Enjoy cozy nights by the wood-burning fireplace in the living room and enjoy

    Crystal Smith RE/MAX Executive

    165 Char Nor Manor Blvd, Chestertown, MD 21620
  • /33

    $554,500

    • 3 Beds
    • 1 Bath
    • 1,762 Sq Ft

    251 Rings End Rd, Millington, MD 21651

    Wildlife abounds on this scenic and private upper Chester River Property. Small wharf on the River lends itself to kayaking, small boats and terrific fishing. One story in a sylvan setting. Large storage building. Easy access to shopping in Millington and Middletown DE. One hour commute to Wilmington, 1.5 to Philadelphia with very easy access to MD Route 301. Well maintained by 30-year owner.

    Jo Ann Edwards The Hogans Agency

    251 Rings End Rd, Millington, MD 21651
  • /64

    $659,899

    • 5 Beds
    • 4.5 Baths
    • 4,870 Sq Ft

    113 Stone Ivy Ln, Church Hill, MD 21623

    Welcome to this stunning 4/5-bedroom, 4.5-bath, 4,870 sq ft home, beautifully maintained and thoughtfully upgraded for modern living. Freshly painted throughout in 2022, with new carpet and premium hardwood floors and new ceiling fans. This spacious residence is move-in ready and shines with pride of ownership.Step into a grand two-story foyer that opens to expansive formal and casual living

    Brett Schrader Taylor Properties

    113 Stone Ivy Ln, Church Hill, MD 21623
  • /51

    $549,000

    • 3 Beds
    • 2.5 Baths
    • 1,574 Sq Ft

    405 Chester River Heights Rd, Millington, MD 21651

    CHESTER RIVER WATERFRONT - Affordably priced, tastefully updated waterfront home on the upper Chester River, less than one mile to route 301 for commuting. Private 1 acre lot with scenic water views and a gentle path down to the waters edge with area for relaxation and fishing on small pier. Home sits perched high on the hillside so fabulous birds eye views and no need for flood insurance here!

    John Carroll Village Real Estate Company LLC

    405 Chester River Heights Rd, Millington, MD 21651
  • /35

    $475,000

    • 3 Beds
    • 1.5 Baths
    • 2,767 Sq Ft

    116 Pine Chip Rd, Chestertown, MD 21620

    Don’t let the outside fool you—this beautifully renovated 3-bedroom, 1.5-bathroom home offers three levels of living space, with over 2,200 sq. ft. above ground and an additional 550 sq. ft. below ground! Every inch of this home has been thoughtfully updated to blend modern comfort with timeless charm.Step inside to discover a stunning custom kitchen, a true chef’s dream featuring a gas

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    116 Pine Chip Rd, Chestertown, MD 21620
  • /77

    $614,700 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,850 Sq Ft

    334 ( Lot 22) Eagle Manor Dr, Church Hill, MD 21623

    To be built in the community of Condor Manor in Church Hill! This is Red Oak's most popular model with various options avaiable . This Pin Oak model, built by Red Oak Properties, LLC is a must see home featuring LVP flooring all throughout the home, upgraded kitchen oversized Island, perfect for preparing meals or entertaining. Entertaining can continue outside to the maintenance free deck.

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    334 ( Lot 22) Eagle Manor Dr, Church Hill, MD 21623
  • /18

    $669,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,414 Sq Ft

    326 Eagle Manor Dr, Church Hill, MD 21623

    Don’t miss your opportunity to own this stunning brand new home! This home is located in Condor Manor, there aren’t many homes left in this community so act fast! This home is detailed with beautiful craftsman style trim and a custom built-in in the family room. Each bedroom features a walk in closet, and has a laundry room located on the same floor. Construction is almost complete and ready for

    Cody Weese Weese Properties, LLC

    326 Eagle Manor Dr, Church Hill, MD 21623
  • /56

    $349,500

    • 3 Beds
    • 2 Baths
    • 1,867 Sq Ft

    1631 Barclay Rd, Barclay, MD 21607

    This beautifully updated and move-in ready home has been well-maintained and features extensive recent improvements both inside and out. The primary en suite bathroom was completely renovated in May 2025, showcasing a walk-in shower and an impressive Toto Washlet toilet. The kitchen has received several upgrades, including new flooring (2022), freshly painted cabinets with updated

    Chris Rosendale CR Realty

    1631 Barclay Rd, Barclay, MD 21607
  • /2

    $90,000

    • Land
    • 8.79 Acres
    • $10,239 per Acre

    0 Goldsboro Rd, Barclay, MD 21607

    8.79+/- lot on the west side of Goldsboro Road. Soils are mostly Hurlock Sandy Loam with some longmarsh/indiantown soils(wet bottom) where the head waters of Red Lion Branch run through the property. No perc test. Buyer to perform their own due diligence.

    Benjamin Alder The Land Group

    0 Goldsboro Rd, Barclay, MD 21607
  • /35

    $399,000

    • 3 Beds
    • 2.5 Baths
    • 1,695 Sq Ft

    111 Dell Foxx Rd, Barclay, MD 21607

    Escape to the tranquility of rural living with this delightful 3 bedroom, 2 bath property nestled on a sprawling 1-acre parcel. Located in the heart of the countryside, this inviting home is ideal for a permanent home or as a second home to enjoy everything the Eastern Shore of Maryland has to offer, such as hunting, fishing, boating, or just a peaceful getaway. The vaulted living area is

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    111 Dell Foxx Rd, Barclay, MD 21607
  • /2

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,424 Sq Ft

    119 Darden Rd, Chestertown, MD 21620

    Welcome to 119 Darden Road, a lovely ranch-style home nestled in Chestertown, MD. This charming residence offers 3 cozy bedrooms and 2 bathrooms across 1,424 square feet of living space, perfect for comfortable living. The eat-in kitchen, complete with a handy stove, sets the stage for delightful meals and gatherings. Enjoy the warm ambiance of a fireplace in the spacious living room, enhanced by

    Solomon Zaldivar Compass

    119 Darden Rd, Chestertown, MD 21620
  • /38

    $359,900 Open Sat 1:30PM - 3:30PM

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft

    111 Cee Jay Rd, Chestertown, MD 21620

    Beautiful, like new rancher built in 2021 offers 4 bedrooms and 2 baths. Luxury vinyl tile throughout much of the house including the primary bedroom. Seller has upgraded all plumbing fixtures, added kitchen backsplash, added shiplap, fully fenced rear yard with vinyl fencing, and more. Open kitchen, dining and living area. Freshly painted and landscaped. Located 45 minutes from Bay Bridge

    Michelle Abplanalp Rosendale Realty

    111 Cee Jay Rd, Chestertown, MD 21620
  • /18

    $549,900

    • Land
    • 5.53 Acres
    • $99,439 per Acre

    202 Everett Ln, Church Hill, MD 21623

    Great opportunity for an investor or builder. 24 units in established 55+ community. Sewer allocations are available, and the community is served by its own on site well water system. Located in quiet small Eastern Shore town close to parks, and theater. Just minutes to Centreville or Chestertown. 5 Building sites which could be sold separately. $23,000/Unit

    Jason Dey Kevin Dey Realty

    202 Everett Ln, Church Hill, MD 21623
  • /39

    $949,900

    • 3 Beds
    • 2 Baths
    • 2,600 Sq Ft

    492 Pear Tree Point Rd, Chestertown, MD 21620

    Great opportunity to own a waterfront property on the scenic Chester River! This beautifully landscaped 3 bedroom, 2 bath home with a wraparound porch offers stunning views. There is an additional partially finished 700+/- sq ft space over the garage, filled with natural light and river views, ideal for extra bedrooms with bath, master bedroom or an in-law suite. Tucked away in a peaceful,

    Leo Kuneman Meredith Fine Properties

    492 Pear Tree Point Rd, Chestertown, MD 21620
  • /36

    $424,000

    • 3 Beds
    • 3 Baths
    • 1,300 Sq Ft

    600 Rosin Dr, Chestertown, MD 21620

    Nestled along the peaceful shores of Rosin Creek, this charming 3-bedroom, 2-bathroom waterfront cottage combines classic character with modern updates. Inside, the open floor plan creates a warm, inviting flow—perfect for everyday living or entertaining. The renovated kitchen features stylish finishes and connects seamlessly to the dining and living areas, all enhanced by updated flooring and

    Sarah King Cross Street Realtors LLC

    600 Rosin Dr, Chestertown, MD 21620
  • /56

    $420,000

    • 3 Beds
    • 2.5 Baths
    • 1,484 Sq Ft

    321 Front St, Crumpton, MD 21628

    Welcome to this charming and thoughtfully cared-for home in the heart of Crumpton!The current owners have cherished the past three years here, making lasting memories while enhancing the home with artistic touches and practical upgrades that truly make it Home Sweet Home. Now, as life leads them in a new direction, this beautiful property is ready for its next chapter.Step inside

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    321 Front St, Crumpton, MD 21628
  • /15

    $199,900

    • Land
    • 2 Acres
    • $99,950 per Acre

    3355 Church Hill Rd, Centreville, MD 21617

    Approximately 2 acres zoned Village Center. Currently improved by older 2 story dilapidated house in need of tear down. Do not enter. Property has 580' of road frontage on both Rt. 213 and Clabber Hill Road. Great visibility and traffic count. Located in up and coming crossroad between Centreville and Chestertown. Village Center Zoning allows for residential and some light commercial uses. This

    Jason Dey Kevin Dey Realty

    3355 Church Hill Rd, Centreville, MD 21617
  • /12

    $145,000

    • Land
    • 1 Acre
    • $145,000 per Acre

    435 Eagle Manor Dr, Church Hill, MD 21623

    Guess what! Just released 3 buildable lots with no builder tie-in! Don't wait! Buy your own lot and build new in the community of Condor Manor in Church Hill, Md. Get this why you can, communites like this in Maryland will soon be a thing of the past with the opportunity to build new in a cul-de-sac type community with well and septic. This beautiful community consisting of a total of 23, 1

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    435 Eagle Manor Dr, Church Hill, MD 21623
  • /12

    $135,000

    • Land
    • 1 Acre
    • $135,000 per Acre

    334 Eagle Manor Dr, Church Hill, MD 21623

    Guess what! Just released 3 buildable lots with no builder tie-in! Don't wait! Buy your own lot and build new in the community of Condor Manor in Church Hill, Md. Get this why you can, communites like this in Maryland will soon be a thing of the past with the opportunity to build new in a cul-de-sac type community with well and septic. This beautiful community consisting of a total of 23, 1

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    334 Eagle Manor Dr, Church Hill, MD 21623
  • /12

    $135,000

    • Land
    • 1 Acre
    • $135,000 per Acre

    0 Eagle Manor ( Lot 20) Dr, Church Hill, MD 21623

    Guess what! Just released 3 buildable lots with no builder tie-in! Don't wait! Buy your own lot and build new in the community of Condor Manor in Church Hill, Md. Get this why you can, communites like this in Maryland will soon be a thing of the past with the opportunity to build new in a cul-de-sac type community with well and septic. This beautiful community consisting of a total of 23, 1

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    0 Eagle Manor ( Lot 20) Dr, Church Hill, MD 21623
  • /29

    $399,900

    • 4 Beds
    • 2.5 Baths
    • 1,712 Sq Ft

    2005 Stulltown Rd, Sudlersville, MD 21668

    Awesome renovated sprawling ranch home on a country acre near the Delaware line and close to tax free shopping! NEW NEW NEW - new LVP flooring and carpet, fresh paint, new lighting, and ceiling fans, new kitchen cabinets with granite countertops, new appliances, updated bathrooms, new central heating and air conditioning, new roof, updated windows and doors. BRAND NEW SEPTIC INSTALLED. Full

    John Carroll Village Real Estate Company LLC

    2005 Stulltown Rd, Sudlersville, MD 21668
  • /6

    $149,900

    • Land
    • 5.07 Acres
    • $29,566 per Acre

    0 Trunk Line Rd Unit MDCM2005918, Henderson, MD 21640

    Secluded 5-Acre Perc-Approved Building LotNestled on a quiet country back road, this beautiful 5-acre parcel offers peace, privacy, and great potential. The front section—where the perc test has been approved—is lightly overgrown with small saplings, making for easy clearing and minimal cost to install a driveway and run utilities to your future home site.The rear portion of the property features

    Brett Schrader Taylor Properties

    0 Trunk Line Rd Unit MDCM2005918, Henderson, MD 21640
  • /11

    $103,000

    • Land
    • 0.48 Acre
    • $214,583 per Acre

    0 East St, Chestertown, MD 21620

    Great chance to purchase a corner lot just across the river from Chestertown's Historic District. Sit and listen to the birds by the pond on this peaceful retreat just minutes from the town's shops, galleries, and waterfront. There aren't many more opportunities like this. Please see the documents for the perc approval and site plan.

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    0 East St, Chestertown, MD 21620
  • /3

    $85,000

    • Land
    • 0.95 Acre
    • $89,474 per Acre

    Parcel 104 Pfalzgroff Rd, Millington, MD 21651

    Just Listed! Build your Dream Home! This is a beautiful lot sited on almost 1 acre and is perfect for your home! Mostly cleared and backs to trees. Located just 2 minutes from Route 301 and 5 minutes from the heart of Millington and Crumpton, this home combines tranquility with accessibility.205 Pfalzgroff Rd, the home next door, is also available for sale...ideal for expansion, investment, or

    Darlene Winegardner RE/MAX Executive

    Parcel 104 Pfalzgroff Rd, Millington, MD 21651
  • /13

    $525,000

    • Land
    • 52 Acres
    • $10,096 per Acre

    0 Baxter Rd, Sudlersville, MD 21668

    52+/- acre farm located on the corners of Baxter Rd and Bolton Woods Rd in Sudlersville, MD. The property consists of 34+/- acres of tillable ground and 18+/- acres of timber. Soils are primarily ingleside sandy loam. DO NOT NTER PROPERTY WITHOUT PERMISION OF THE LAND GROUP.

    Benjamin Alder The Land Group

    0 Baxter Rd, Sudlersville, MD 21668
  • /25

    $349,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 1.5 Baths
    • 2,240 Sq Ft

    549 Main St, Church Hill, MD 21623

    Move-In Ready Historic Home in Walkable Church HillWelcome to this beautifully renovated 4-bedroom, 1.5-bath historic home, where timeless character meets modern convenience. Nestled on an oversized lot in the heart of Church Hill. Offerring everything you are searching for —space, style, and small-town charm.Inside, you’ll find gleaming hardwood floors, soaring ceilings, and abundant

    Stacy Kendall Cross Street Realtors LLC

    549 Main St, Church Hill, MD 21623
  • /2

    $39,000

    • Land
    • 0.41 Acre
    • $95,122 per Acre

    3815 Barclay Rd, Marydel, MD 21649

    Lot has been surveyed and septic reserve on plat. Ready for a build.

    Barbara Wallace Long & Foster Real Estate, Inc.

    3815 Barclay Rd, Marydel, MD 21649
  • /150

    $3,750,000

    • 8 Beds
    • 6.5 Baths
    • 7,206 Sq Ft

    148 Vernick Ln, Church Hill, MD 21623

    Experience unparalleled waterfront living in this stunning Coastal Farmhouse situated on 13.2 private acres in the desirable Kennersley Farm community. Custom-built as a former builder’s residence, this home showcases the highest quality materials and exceptional craftsmanship throughout. With 8 bedrooms and 6 full baths in the main house, plus a charming 2-bedroom Carriage House with a full

    Creig Northrop Northrop Realty

    148 Vernick Ln, Church Hill, MD 21623
  • /59

    $415,000

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

    128 Edmore Rd, Chestertown, MD 21620

    Your Dream Eastern Shore Retreat Awaits!Welcome to this meticulously maintained home, where charm and comfort blend seamlessly. Whether you're savoring peaceful nights or hosting lively gatherings, this home offers the perfect setting.Step into the breathtaking four-seasons room, where natural light pours in, highlighting an authentic reclaimed barn wood accent wall—crafted from

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    128 Edmore Rd, Chestertown, MD 21620
  • /16

    $120,000

    • Land
    • 10 Acres
    • $12,000 per Acre

    0 Bear Pond Rd, Marydel, MD 21649

    Beautiful 10 acres wooded lot perfect for hunting or other outdoor activities. Surrounded by woods on both sides. No perc on file all surveys and testing at buyers expense.

    Shontel Wilmer Rosendale Realty

    0 Bear Pond Rd, Marydel, MD 21649
  • /31

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    109 Wilton Rd, Chestertown, MD 21620

    Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience with one-level living in the desirable Chester Harbor community. Set on a spacious .76-acre lot on the Queen Anne's side of the Chester River, this home is ideally situated in a water-oriented neighborhood, perfect for boating enthusiasts and nature lovers alike.The home boasts a

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Wilton Rd, Chestertown, MD 21620
  • /7

    $275,000

    • Land
    • 1.82 Acres
    • $151,099 per Acre

    1511 Barclay Rd, Barclay, MD 21607

    Two parcel lots in Barclay zoned Town Center offers a great opportunity to build a warehouse, business office, or other structure. The seller will pay for a basic sewer hookup! Please call the Town of Barclay with any questions about building restrictions, etc. Must call the Town of Sudlersville with any sewer questions.

    Tina Brown Benson & Mangold, LLC

    1511 Barclay Rd, Barclay, MD 21607
  • /8

    $185,000

    • Land
    • 9.06 Acres
    • $20,419 per Acre

    1420 Barclay Rd, Barclay, MD 21607

    Welcome to the quaint town of Barclay! Get lost on this 9 acre lot and let your dreams of building a beautiful home lead you. Graced with gorgeous shady trees , the country landscape is breathtaking. In city limits, but sits just on the outskirts of the town. This beautiful lot comes with accessible public sewer and cable WiFi that has recently been installed throughout the town. Just a stones

    Myisha Walker Long & Foster Real Estate, Inc.

    1420 Barclay Rd, Barclay, MD 21607
  • /2

    $250,000

    • Land
    • 14 Acres
    • $17,857 per Acre

    231 Ingleside Rd, Ingleside, MD 21644

    VERY MOTIVATED SELLER - BRING YOUR OFFER. Please note the buyer is responsible for conducting all due diligence on lot. Including use, restrictions, and taxes. The parcel is landlocked, with no easement in place.

    Angelita Mosley Taylor Properties

    231 Ingleside Rd, Ingleside, MD 21644
  • /2

    $139,900

    • Land
    • 2 Acres
    • $69,950 per Acre

    0 Busic Church Rd, Marydel, MD 21649

    Alice Stewart Coldwell Banker Realty

    0 Busic Church Rd, Marydel, MD 21649
  • /40

    $374,500 New Construction

    • 3 Beds
    • 2 Baths
    • 1,064 Sq Ft

    550 Bolton Woods Rd, Sudlersville, MD 21668

    Welcome to 550 Bolton Woods Road in Sudlersville, Maryland — a stunning new construction rancher that perfectly blends modern comfort with peaceful country charm. This beautifully built home features 3 spacious bedrooms, 2 full bathrooms, and an attached 1-car garage, offering both functionality and style.Step inside to an open floor plan filled with natural light and luxury vinyl plank

    Crystal Smith RE/MAX Executive

    550 Bolton Woods Rd, Sudlersville, MD 21668

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