15,758

Caroline, MD Homes

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  • /31

    $250,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,344 Sq Ft

    21344 Tanyard Rd, Preston, MD 21655

    Classic Charm Meets Modern Comfort on the Eastern ShoreWelcome to 21344 Tanyard Road—a spacious 4-bedroom, 2-bath single-family home nestled on a private, tree-lined 1⁄2-acre lot in Preston, MD. Just 5 miles from Easton and Route 50, this inviting property offers the perfect blend of peace, privacy, and proximity to everyday conveniences.Step inside to find gleaming hardwood

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (667) 771-3387

    21344 Tanyard Rd, Preston, MD 21655
  • /24

    $2,500 per month

    • 3 Beds
    • 2 Baths
    • 1,176 Sq Ft
    • House for Rent

    318 S 4th St, Denton, MD 21629

    Charming newly renovated home in the heart of Denton, Md. for rent. This 3 br 2 full bath home boasts upgraded appliances, privacy fenced back yard with shed. Lease terms are for 1 or 24 months. First month rent and deposit with signed lease. No Pets No Smoking. Complete application through Rent Spree. Applicant pays 49.99. Go to the following link to access application

    Agent Photo

    Darrel Reel

    Corner House Realty

    (410) 541-1263

    318 S 4th St, Denton, MD 21629
  • /30

    $1,275,000 Sold Aug 01, 2025

    • 1,872 Sq Ft
    • $681/SF
    • 4 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1900

    21171 Wood Wharf Ln, Preston, MD 21655

    Located off Tanyard Road, this 81-acre waterfront farm offers a rare blend of charm, seclusion, and natural beauty. The property features a delightful cottage, circa 1900, renovated in 2014 with additional upgrades including new HVAC in 2019. Set among mature trees and outside the floodplain, the home includes two bedrooms, two and a half baths, a waterside living room with wood stove, a

    Coard Benson Benson & Mangold, LLC

    21171 Wood Wharf Ln, Preston, MD 21655
    • /10

      Est $596,534 Not Listed For Sale

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

      Unlisted Address

      Unlisted Address
  • /30

    $439,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft

    4808 Frazier Neck Rd, Preston, MD 21655

    Owner says SELL & has relocated! Home Warranty Included. Hard to find 9+ acres with updated 3/4BR home, 4-5 acres cleared & the rest wooded just a few miles from Easton, hospitals, shopping, doctors, boat ramps/river, airport and parks but in beautiful private setting. Low AG taxes as local farmer has been planting the front field. Bring the animals, 4 wheelers, home based business, hunt and

    Agent Photo

    Brenda Fornos

    Taylor Properties

    (667) 326-9080

    4808 Frazier Neck Rd, Preston, MD 21655
  • /16

    $465 - $1,290 per month

    Riverwoods at Denton

    1 - 3 Beds

    101 Quinn Cir, Denton, MD 21629

    Riverwoods at Denton is an affordable housing community featuring newly renovated existing apartments and 36 apartment homes. All of the apartments offer the latest Green energy-saving and conserving features and include a modern kitchen, with abundant cabinetry as well as dishwasher, disposal and microwave. Handicap accessible apartments are also available.Riverwoods at Denton features a 1,500

    101 Quinn Cir, Denton, MD 21629
  • /16

    $265,000 Sold Jul 31, 2025

    • 1,136 Sq Ft
    • $233/SF
    • 7 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1991

    17 Greenridge Ave, Ridgely, MD 21660

    Move in Ready! Well Maintained Rancher with Public Water & Sewer offers 3 bedrooms, 1 bath, spacious rear yard with deck, Newly remodeled Bath with tile shower, floor and blue tooth ceiling feature. Central Heat & A/c installed in 2023 with less than 2 yrs old appliances: Refrigerator, Dishwasher and Washer & Dryer. Verizon FISO on premises. Don't miss out on this opportunity - schedule your

    Mary Mabry Keller Williams Select Realtors of Cambridge

    17 Greenridge Ave, Ridgely, MD 21660
    • /23

      Est $321,580 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,632 Sq Ft

      323 Mallard Dr, Greensboro, MD 21639

      323 Mallard Dr, Greensboro, MD 21639
  • /93

    $520,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 1,372 Sq Ft

    13800 Cedar Ln, Greensboro, MD 21639

    Discover Your Dream Farm! This incredible 18-acre property, currently perfect for horses, offers endless possibilities for your agricultural pursuits, hobby farm or a serene country lifestyle. This lovely home features a fireplace and gorgeous honey-toned hardwood floors throughout and an abundance of natural light. The 2BR/1BA cottage is self-sufficient and quaint with an open concept floor

    Agent Photo

    Lona Todd

    Taylor Properties

    (410) 698-4178

    13800 Cedar Ln, Greensboro, MD 21639
  • /38

    $2,650 per month

    • 3 Beds
    • 3 Baths
    • 3,316 Sq Ft
    • House for Rent

    25369 Harpers Branch Dr, Denton, MD 21629

    Privacy abounds at this rustic 3 bed 3 bath waterfront home. Home features cathedral ceiling in the living room, wood laminate floors, large bedrooms 1 with fireplace , 1 with woodstove and kitchenette. A 3 season room with hot-tub and water views ad to the relaxing experience of living at this home. Tenant has access and use of shed and 1 bay garage on the left of the main garage.

    Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    25369 Harpers Branch Dr, Denton, MD 21629
  • /44

    $390,000 Sold Jul 31, 2025

    • 1,228 Sq Ft
    • $318/SF
    • 13 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2014

    10803 Greensboro Rd, Denton, MD 21629

    Pride in Ownership! Amazingly maintained rancher offering one-level living with open floor plan. Chill on your front porch looking out on the fields that make this area so special. Or relax on the new huge back deck while you grill or pick crabs with family and friends. This quiet setting is removed from the hustle and bustle of daily life, yet close to highway access points to DE and the Bay

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    10803 Greensboro Rd, Denton, MD 21629
    • /30

      Est $310,242 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,468 Sq Ft

      319 Mallard Dr, Greensboro, MD 21639

      319 Mallard Dr, Greensboro, MD 21639
  • /44

    $370,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,476 Sq Ft

    3590 Choptank Rd, Preston, MD 21655

    The ULTIMATE DREAM HOME ALERT! Are you tired of feeling like you're stuck in a never-ending cycle of home repairs and renovations? Well, buckle up, friend, because this stunning three-bedroom, two-bath rancher is about to become your happy place!Imagine waking up every morning in a beautiful, meticulously cared-for home, surrounded by lush greenery on a half-acre lot that's just begging

    Agent Photo

    Dawn O'Day

    Samson Properties

    (410) 291-1022

    3590 Choptank Rd, Preston, MD 21655
  • /3

    $1,165 - $1,415 per month

    Sunset Hargraves Ridgely

    1 - 3 Beds

    502 Sunset Blvd, Ridgely, MD 21660

    Welcome to Sunset Hargraves Ridgely, where newly renovated affordable apartment homes meet the charm of Maryland’s Eastern Shore. Located in the heart of Ridgely, our spacious 1, 2, and 3-bedroom apartments feature brand-new kitchens, energy-efficient appliances, luxury vinyl plank flooring, new windows, and more. Community-wide upgrades include new roofing, gutters, and refreshed breezeways,

    502 Sunset Blvd, Ridgely, MD 21660
  • /58

    $345,000 Sold Jul 30, 2025

    • 1,984 Sq Ft
    • $174/SF
    • 91 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 2005

    510 Pintail St, Greensboro, MD 21639

    Do not miss your chance to own this 5-bedroom, 2.5 bath Colonial home with attached garage located in the "Small-Town, Big Heart" city of Greensboro! The gourmet kitchen includes stainless steel appliances, a stylish backsplash, granite countertops, and a pantry. The kitchen/dining room opens to the family room, giving you a great open space to entertain and enjoy family time! The back deck is

    Jon Fleming Weichert Realtors - Blue Ribbon

    510 Pintail St, Greensboro, MD 21639
    • /10

      Est $408,024 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,300 Sq Ft

      1101 Trice Meadows Cir, Denton, MD 21629

      1101 Trice Meadows Cir, Denton, MD 21629
  • /54

    $595,000

    • 4 Beds
    • 2.5 Baths
    • 3,168 Sq Ft

    24766 Tribbett Cir, Ridgely, MD 21660

    Why wait months to build when you can start enjoying this meticulously built, and finely crafted contemporary farmhouse home right now? Situated on an .85 acre lot in the established community of Ashworth, this 2023 built, 3,168 square foot, 4 bedroom, 2.5 bath home contemporary farmhouse-style home blends rustic charm with contemporary elegance. The exterior features classic white siding,

    Barbara McCaffrey Redfin Corp

    24766 Tribbett Cir, Ridgely, MD 21660
  • /21

    $2,250 per month

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Townhouse for Rent

    139 Riverwalk Terrace, Federalsburg, MD 21632

    Brand New Endunit 3 Bedroom 2.5 bath townhome in the heart of Federalsburg. The lower level is bright and spacious with a dining area, kitchen with stainless steel appliances and great room that leads to Deck overlooking the river. The upper levels features 3 bedrooms, 2 full baths and in unit washer and dryer. This Riverside community features nature trails along Marshyhope Creek and over the

    Theresa Deminne O'Brien Realty ERA Powered

    139 Riverwalk Terrace, Federalsburg, MD 21632
  • /31

    $225,000 Sold Jul 25, 2025

    • 1,091 Sq Ft
    • $206/SF
    • 2 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1994

    3427 Holland Dr, Federalsburg, MD 21632

    Welcome to 3427 Holland Dr, a cute home at the end of a cul-de-sac. This 3-bedroom 1-bathroom home is priced to sell! Highlights include a recently installed water heater (2021), a new dishwasher, stove, and refrigerator (2023-24), hardwood floors, and a spacious fenced-in backyard. The home needs carpet in 2 bedrooms and minor drywall repairs. A fresh coat of paint would go a long way. The

    Matthew Olson EXP Realty, LLC

    3427 Holland Dr, Federalsburg, MD 21632
    • /15

      Est $386,523 Not Listed For Sale

      • 3 Beds
      • 2 Baths

      204 Briarwood Cir, Denton, MD 21629

      204 Briarwood Cir, Denton, MD 21629
  • /22

    $369,900

    • 3 Beds
    • 2 Baths
    • 1,746 Sq Ft

    25432 Piney Branch Ln, Denton, MD 21629

    Beautiful country rancher sitting on private 1.16 +- acre lot with mature landscaping. The property features 3 bedrooms, 2 bathrooms, large kitchen, family room, and attached 2 car garage. A bright screened in porch off the back of the home leads to a spacious yard and additional storage shed. Single level with modern amenities, just minutes to downtown Denton shopping and restaurants!

    Brian Gearhart Benson & Mangold, LLC

    25432 Piney Branch Ln, Denton, MD 21629
  • /2

    $670 - $1,109 per month

    Riverview Gardens

    1 - 4 Beds

    500 High St, Denton, MD 21629

    500 High St, Denton, MD 21629
  • /57

    $405,000 Sold Jul 25, 2025

    • 2,994 Sq Ft
    • $135/SF
    • 20 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2006

    1208 Painted Fern Rd, Denton, MD 21629

    BEST VALUE IN THE SOUGHT AFTER COMMUNITY OF SAVANNAH OVERLOOK! This pristine 2006 built, 4 bedroom, 2.5 bath updated colonial is situated on a .25 lot and offers newly installed privacy fence, pemium 50-year architectural roofing system installed 2022 (transferable warranty included), brand new laundry appliances, 2024, new carpeting throughout, 2024, contemporary lighting upgrades interior

    Barbara McCaffrey Redfin Corp

    1208 Painted Fern Rd, Denton, MD 21629
    • /23

      Not Listed For Sale

      • Studio
      • 3,200 Sq Ft

      5 Park Ave, Ridgely, MD 21660

      5 Park Ave, Ridgely, MD 21660
  • /102

    $1,450,000

    • 4 Beds
    • 3.5 Baths
    • 3,356 Sq Ft

    23296 Wilder Way, Denton, MD 21629

    Right out of HGTV! Custom Built in 2020, this 3,350+/- sq ft one-level home offers an abundance of amenities including high ceilings, 4 bedrooms, 3.5 Baths, large open floorplan with huge gourmet kitchen with quartz/ss appliances, separate pantry, family room with stacked stone gas fireplace. The Primary Bedroom is located at one end of the house and includes a large bath with double vanity,

    Brian Gearhart Benson & Mangold, LLC

    23296 Wilder Way, Denton, MD 21629
  • /12

    $1,500 per month

    • 2 - 3 Beds
    • 2 Baths
    • 100 Sq Ft
    • Condo for Rent

    810 Market St, Denton, MD 21629

    AVAILABLE 9/1 second, floor, 2 Br 1 bath duplex. Electric heat,W/D hookup in unit, Walking distance to heart of Denton, short drive to shopping and medical services. 1300 month plus electric and water and sewer (100.00) Non smoking, No pets, Application required for showings, first months rent security deposit to move in.

    810 Market St, Denton, MD 21629
  • /56

    $400,000 Sold Jul 25, 2025

    • 2,500 Sq Ft
    • $160/SF
    • 73 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1984

    18089 Templeville Rd, Marydel, MD 21649

    Welcome to 18089 Templeville Road, a 4-bedroom, 2-bath rancher set on nearly half an acre of wide-open land, with pond and pole barn to max it all out—offering the space you want and the flexibility you need.This home delivers a classic layout with a large living room, separate dining space, and a generously sized kitchen ready for your vision. With a split-bedroom floor plan, the primary

    Phil Gerdes Real Broker, LLC - Annapolis

    18089 Templeville Rd, Marydel, MD 21649
    • /37

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,140 Sq Ft

      18610 Taraila Rd, Marydel, MD 21649

      18610 Taraila Rd, Marydel, MD 21649
  • /53

    $524,225 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,960 Sq Ft

    25833 Spring Branch Dr, Greensboro, MD 21639

    Don't miss this great opportunity to own this beautiful home located in "Spring Branch" that has been totally renovated. The home features 4 bedrooms, 2.5 bathrooms, numerous upgrades including new kitchen cabinets and quartz countertops with a separate island. There is plenty of space to entertain with the 1st floor having a living room, family room, dining room, office and a 1/2 bathroom

    Daniel Foster Long & Foster Real Estate, Inc.

    25833 Spring Branch Dr, Greensboro, MD 21639
  • /5

    $1,300 per month

    • 2 - 3 Beds
    • 1 Bath
    • 100 Sq Ft
    • Condo for Rent

    810 Market St Unit B, Denton, MD 21629

    AVAILABLE 9/1 second, floor, 2 Br 1 bath duplex. Electric heat,W/D hookup in unit, Walking distance to heart of Denton, short drive to shopping and medical services. 1300 month plus electric and water and sewer (100.00) Non smoking, No pets, Application required for showings, first months rent security deposit to move in.

    810 Market St Unit B, Denton, MD 21629
  • /31

    $290,000 Sold Jul 25, 2025

    • 1,265 Sq Ft
    • $229/SF
    • 102 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2024

    278 Wood Duck Dr, Greensboro, MD 21639

    NEW PRICE and THE SELLER IS OFFERING A 1% INTEREST RATE BUY DOWN which could save you $200 a month on your mortgage! No HOA restrictions or monthly fees or extra community closing costs. This stunning newly built home is completed and a must see brought to you by Lomaxx Custom Homes! 278 Wood Duck Drive features 3 bedrooms and 2 beautifully designed bathrooms. From the moment you step inside,

    Crystal Smith RE/MAX Executive

    278 Wood Duck Dr, Greensboro, MD 21639
    • /21

      Est $211,535 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft

      613 Denton Rd, Federalsburg, MD 21632

      613 Denton Rd, Federalsburg, MD 21632
  • /7

    Call for Price

    • Land
    • 39 Acres

    26442 Bee Tree Rd, Henderson, MD 21640

    1,620 sq.ft home on 39.16 acres in Caroline County, Maryland. Home was built in 1993 and has 3 bedrooms and 2 bathrooms. Land is non-contiguous (see overhead mapping pictures).Address:26442 Bee Tree RoadHenderson, MD 21640 Account No.: 01-001485Please see auction page to view this property and place your bids! This residential real estate auction is

    GovDeals GovDeals

    26442 Bee Tree Rd, Henderson, MD 21640
  • /31

    $280,000 Sold Jul 24, 2025

    • 1,456 Sq Ft
    • $192/SF
    • 120 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1981

    5059 Gina Ln, Federalsburg, MD 21632

    PRICE IMPROVEMENT! Three bedroom and two bath rancher in a quiet rural setting on over 1 acre. New roof, appliances, flooring, and paint. Nice family room with a stone fireplace off the eat-in kitchen. Call to schedule your showing today.

    Andrew Beaven Wright Real Estate

    5059 Gina Ln, Federalsburg, MD 21632
    • /3

      Est $64,000 Not Listed For Sale

      510 Lincoln St, Denton, MD 21629

      510 Lincoln St, Denton, MD 21629
  • /3

    $130,000

    • Land
    • 1.00 Acre
    • $130,000 per Acre

    0 Holly Rd Unit 24208711, Ridgely, MD 21660

    Own 1 Acre of Vacant Land in Caroline County, Maryland. This property offers 1 acre of vacant residential and agricultural land, featuring 250 feet of road frontage and access via the peaceful Holly Road. With a tranquil rural setting, this versatile property provides privacy, space, and zoning that supports both farming and single-family development. Property Highlights:Location:

    Community Lands

    0 Holly Rd Unit 24208711, Ridgely, MD 21660
  • /24

    $349,900 Sold Jul 23, 2025

    • 1,200 Sq Ft
    • $292/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2025

    5540 American Corner Rd, Federalsburg, MD 21632

    Escape to your own slice of paradise with this stunning new construction country home, set on 3.279 acres of serene land just outside Denton in rural Federalsburg, Maryland. Step inside the spacious 1,200-square-foot haven and discover a bright, open main level, where a sleek, modern kitchen with quartz countertops, white Kraftmaid cabinetry, and Frigidaire Gallery appliances makes cooking a joy

    David Moore RE/MAX Executive

    5540 American Corner Rd, Federalsburg, MD 21632
    • /16

      Est $152,444 Not Listed For Sale

      4845 Houston Branch Rd, Federalsburg, MD 21632

      4845 Houston Branch Rd, Federalsburg, MD 21632
  • /144

    $1,449,000

    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    24512 Marblehead Rd, Ridgely, MD 21660

    This 99-acre wooded farm offers a well-rounded mix of equestrian, hunting, and homesteading features. Lovely 2 bedroom, 3 bath home, built in 2004, includes vaulted ceilings, a brick hearth propane fireplace with remote, hardwood flooring, and a fully conditioned crawlspace. A wrap-around front porch overlooks the horse pasture and garden, and the rear enclosed screen porch opens to a large brick

    Mike Arajakis

    24512 Marblehead Rd, Ridgely, MD 21660
  • /18

    $425,000 Sold Jul 23, 2025

    • 3,482 Sq Ft
    • $122/SF
    • 78 Days On Market
    • Studio
    • Built 1890

    8 N 2nd St, Denton, MD 21629

    Price Improvement! Historic District in Downtown Denton. The Downes House consists of four apartments and a commercial office. Fourth unit was most recently occupied by Caroline County Chamber of Commerce but contains a kitchen with full bath and can be utilized as a commercial office or an apartment ( flex space ). Most recent fully occupied yearly gross income was $57,000.Replacement windows

    Andrew Beaven Wright Real Estate

    8 N 2nd St, Denton, MD 21629

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