169

Caroline County MD Homes for Sale

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  • /40

    $305,000

    • 5 Beds
    • 2 Baths
    • 1,884 Sq Ft

    407 W Sunset Ave, Greensboro, MD 21639

    Charming 5BR detached home, located in a quiet neighborhood in Greensboro. Experience the great outdoors in your own backyard on a nearly 1/2 acre lot, adjacent to 140 acres of farmland. Enjoy the 'Sunset' from the 320 sf sunroom with sliding glass doors, or sit outside to watch the sunrise on the new 230 sf wooden front porch. Several updates include replacement windows, upgraded plumbing &

    Raphael Szendro R&R Executive Realty

    407 W Sunset Ave, Greensboro, MD 21639
  • /11

    $750,000

    • 4 Beds
    • 3 Baths
    • 2,432 Sq Ft

    12136 Holly Rd, Ridgely, MD 21660

    Set in a peaceful pastural setting , this impeccably maintained horse farm offers the perfect blend of country living and thoughtfully designed equestrian amenities. The beautifully cared-for 4-bedroom, 3-bath home , offering generous living spaces and a warm atmosphere, welcomes you with custom touches and serene views from all angles. Hardwood floors flow throughout the lower level making the

    Donna Harrington Coldwell Banker Realty

    12136 Holly Rd, Ridgely, MD 21660
  • /30

    $335,000

    Open Sat 1PM - 3PM Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,360 Sq Ft

    1309 Fairfield Ct, Denton, MD 21629

    Welcome home to this charming and well maintained 3 bedroom, 2.5 bath home tucked away on a quiet cut-de-sac in a desirable neighborhood. After entering through the inviting front porch, inside you will find a home that has been lovingly cared for and beautifully decorated creating a warm atmosphere throughout. The spacious layout offers comfortable living spaces for everyday and entertaining.

    Ashley Yost Douglas Realty, LLC

    1309 Fairfield Ct, Denton, MD 21629
  • /66

    $374,990

    Coming Soon
    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft

    23116 Gilpin Point Rd, Preston, MD 21655

    Welcome to 23116 Gilpin Point Road in Preston, an updated Eastern Shore rancher offering the perfect blend of one floor living, privacy, history, and water oriented lifestyle. Beautifully situated on a spacious setting in the historic Gilpin Point area, this inviting home provides a peaceful country backdrop while still offering convenient access to nearby towns, commuter routes, and the gorgeous

    Angela Demattia Berkshire Hathaway HomeServices PenFed Realty

    23116 Gilpin Point Rd, Preston, MD 21655
  • /28

    $595,000

    • 3 Beds
    • 3.5 Baths
    • 3,276 Sq Ft

    23730 Henry Rd, Ridgely, MD 21660

    Beautiful Craftsman Cape Cod on quiet country road in Caroline County. This 3,200 sq ft home was built in 2023 and offers an open floor plan with all the amenities...large family room with vaulted ceilings, private office, large kitchen with white cabinets, farm sink, SS appliances, separate butler's pantry, and separate laundry room, first floor primary with walk-in closet, high-end primary

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 406-6991

    23730 Henry Rd, Ridgely, MD 21660
  • /5

    $89,900

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft

    305 Old Denton Rd, Federalsburg, MD 21632

    Investor Alert!! This rancher, situated on over half an acre, is packed with value-add potential! With some TLC and the right vision, this property could be transformed into a strong income-producing asset or profitable flip in no time. Whether you’re looking to renovate and rent or resell, the opportunity here is undeniable—especially with a motivated seller ready to make a deal. Located in

    Aubrey Campbell Keller Williams Realty Delmarva

    305 Old Denton Rd, Federalsburg, MD 21632
  • /2

    $379,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 2,618 Sq Ft

    410 Wood Duck Dr, Greensboro, MD 21639

    Welcome to this spacious three-level home offering flexible living space and a functional floor plan! The main level features a bright living room that flows in the open kitchen. Separate dining room for those family gatherings. Also, on this level is a half bath and a small guest bedroom or turn into your reading area or an office space. Upstairs, you'll find three additional bedrooms and the

    Pamela Geib Long & Foster Real Estate, Inc.

    410 Wood Duck Dr, Greensboro, MD 21639
  • /38

    $479,000

    • 4 Beds
    • 2.5 Baths
    • 2,747 Sq Ft

    8605 Hickory Place, Denton, MD 21629

    Beautiful Colonial Farmhouse nestled on a wooded lot at the end of a cul-de-sac private lane. This 4 bedroom, 2.5 bath home has been meticulously maintained and features a traditional floor plan with a large kitchen/breakfast area, large family room with vaulted ceilings and a gas fireplace, separate dining room, living room/office. Second floor includes a primary suite with large bathroom with a

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 998-8840

    8605 Hickory Place, Denton, MD 21629
  • /63

    $1,500,000

    • 3 Beds
    • 3.5 Baths
    • 3,958 Sq Ft

    7347 Harmony Rd, Preston, MD 21655

    Income-producing poultry farm situated on approximately 38.17 acres in desirable Caroline County, featuring four state-of-the-art “Tier 3” tunnel poultry houses with a combined capacity of approximately 110,000 broiler chickens. Built in 1993, the four 40’ x 500’ houses are equipped with Rotem Platinum+ controllers, Shore Time computerized controls, alarm systems, recirculation cooling pads, 6”

    Agent Photo

    Damon Brockenberry

    Keller Williams Preferred Properties

    (667) 249-7301

    7347 Harmony Rd, Preston, MD 21655
  • /44

    $464,000

    • 5 Beds
    • 3.5 Baths
    • 3,040 Sq Ft

    7 Lister Ln, Ridgely, MD 21660

    Welcome to this Grand Colonial! One of the Largest homes in the neighborhood with a fully finished basement! New Roof 2025 & New HVAC 2024!!!Main level Features an open concept -great room, massive kitchen with sunroon. 10ft ceilings in the main level give this home an amazing flow with bright sunshine from all the windows. Large Kitchen with Lots of storage, 2 pantries, and a Huge Island

    Kathleen Brenton Brenton Realty Group

    7 Lister Ln, Ridgely, MD 21660
  • /16

    $415,000

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,628 Sq Ft

    5 Sunrise Ave, Ridgely, MD 21660

    Colors, materials, and finishes are subject to change New Construction Home built by the reputable Lomaxx Custom Homes! The final home in Sunrise Village, this is your opportunity to get in early and make your personal selections. This one story home will offer 4 bedrooms, 2 full bathrooms and an open concept layout with stylish and on trend finishes throughout. Home to be completed Summer of

    Amy Betts Coldwell Banker Realty

    5 Sunrise Ave, Ridgely, MD 21660
  • /62

    $519,900

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,805 Sq Ft

    8047 Laurel Ln, Denton, MD 21629

    Welcome to 8047 Laurel Lane in Denton, Md. First time ever offered on the market! Tucked away on 1.4 private, wooded acres in Denton’s sought-after Forest Landing community, this custom-built 3BR/2BA home features a pristine inground pool, a brand-new roof, and water-privileged community access just minutes from the Tuckahoe Creek, leading into the Choptank River. Property Highlights:Move-In

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    8047 Laurel Ln, Denton, MD 21629
  • /16

    $340,000

    • 3 Beds
    • 2 Baths
    • 1,892 Sq Ft

    11502 Greensboro Rd, Greensboro, MD 21639

    This is an auction property.This property has been placed in an upcoming event. Please reach out to the listing agent on where the bids are to be submitted. Please submit any pre-auction offer received through the property details page, please reach out to the listing agent. Any post-auction offers will need to be submitted directly to the listing agent. Response within 3 business days. All

    Pamela Geib Long & Foster Real Estate, Inc.

    11502 Greensboro Rd, Greensboro, MD 21639
  • /2

    $350,000

    • 3 Beds
    • 2 Baths
    • 2,412 Sq Ft

    1302 Trice Meadows Cir, Denton, MD 21629

    Welcome home to this warm and inviting Rancher situated on a 0.1950-acre lot, offering plenty of space for everyday living, relaxing, and entertaining. This charming home features three bedrooms, an office/den perfect for working from home or a guest space, and two full baths. The kitchen opens to the dining area and family room, creating a wonderful flow for gatherings with family and friends.

    Lori Guimond Keller Williams Select Realtors of Easton

    1302 Trice Meadows Cir, Denton, MD 21629
  • /2

    $95,000

    • 1 Bed
    • 1 Bath
    • 692 Sq Ft

    316 Liberty Rd, Federalsburg, MD 21632

    Nestled in the charming TOWN OF FEDERALSBURG, this exquisite bungalow, built in 1930, seamlessly blends timeless elegance with modern comforts. This delightful residence invites you to experience a lifestyle of warmth and sophistication, perfect for those seeking a serene retreat. As you approach the property, the classic vinyl siding and inviting front entry beckon you inside. Step into a cozy

    Barton Johnson/not int Marshy Hope Realty LLC

    316 Liberty Rd, Federalsburg, MD 21632
  • /20

    $225,000

    • 4 Beds
    • 1 Bath
    • 1,350 Sq Ft

    5258 Preston Rd, Federalsburg, MD 21632

    4 bedrooms 1 bathroom bungalow being sold "AS IS". 16,700 sq. ft. lot with detached garage. Priced to Sell.Updated 200. amp electric service.

    Barton Johnson/not int Marshy Hope Realty LLC

    5258 Preston Rd, Federalsburg, MD 21632
  • /87

    $1,550,000

    • 5 Beds
    • 4.5 Baths
    • 4,853 Sq Ft

    322 S 2nd St, Denton, MD 21629

    Wake up to sunrise on the Choptank River and wind down with some of the most stunning sunsets on the Eastern Shore — with Ospreys, Eagles, Herons, and an abundance of wildlife as your daily backdrop. This stunning 4,853 sq ft waterfront estate sits on 2.44 acres with 268 feet of private river frontage, putting you right on the water and just steps from the best of historic downtown Denton. Built

    Agent Photo

    Elizabeth Osborn

    Coldwell Banker Realty

    (410) 970-3374

    322 S 2nd St, Denton, MD 21629
  • /34

    $799,000

    New Construction $26K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    16960 Lentz Rd, Henderson, MD 21640

    Discover the charm of this newly constructed Cape Cod home, completed in 2026, where modern elegance meets timeless design. Nestled on a generous 19.16-acre lot, this detached residence offers a serene retreat while providing ample space for outdoor activities and future possibilities. Step inside to find a thoughtfully designed layout featuring three spacious bedrooms and two and a half

    Taylor Leaverton Benson & Mangold, LLC

    16960 Lentz Rd, Henderson, MD 21640
  • /2

    $25,000

    • Land
    • 12,196 Sq Ft
    • $89,286 per Acre

    12087 Wayman St, Ridgely, MD 21660

    Double lot . There are the remains of a house on the property; please leave the remains "as is". Well and septic unknown.

    Bev Langley Coldwell Banker Realty

    12087 Wayman St, Ridgely, MD 21660
  • /2

    $27,500

    • Land
    • 12,196 Sq Ft
    • $98,214 per Acre

    0 Charlotte Ave, Federalsburg, MD 21632

    Build your dream home in the heart of Federalsburg! This approximately 0.28-acre residential lot is located within town limits and is zoned R-1 Single Family Residential. Public water and public sewer are available, offering a great opportunity for new construction in an established community. Conveniently located near local parks, schools, shopping, dining, and major commuter routes. Whether

    Heather Brummell Keller Williams Realty

    0 Charlotte Ave, Federalsburg, MD 21632
  • /28

    $369,900

    • 3 Beds
    • 2 Baths
    • 1,538 Sq Ft

    5 Seward Rd, Ridgely, MD 21660

    Welcome to this beautifully updated 3-bedroom, 2-bath contemporary home offering the perfect blend of modern style and everyday comfort. From the moment you step inside, you'll appreciate the open-concept layout,, abundant natural light, and thoughtfully renovated finishes throughout. The spacious living areas flow seamlessly into the updated kitchen featuring nice cabinetry, modern countertops,

    James DiPietro Keller Williams Select Realtors of Annapolis

    5 Seward Rd, Ridgely, MD 21660
  • /36

    $239,900

    • 3 Beds
    • 1 Bath
    • 1,252 Sq Ft

    302 Vernon Ave, Federalsburg, MD 21632

    Fully Updated & Move-In Ready: Charming Corner-Lot Bungalow Near Downtown!Property OverviewWelcome to 302 Vernon Ave, a charming and beautifully refreshed 3-bedroom one bath bungalow that is completely move-in ready! Situated on a desirable corner lot close to downtown Federalsburg, this home perfectly blends classic bungalow character with extensive modern updates. The property boasts a

    Eddie Matthews Benson & Mangold, LLC

    302 Vernon Ave, Federalsburg, MD 21632
  • /23

    $304,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft

    109 Hobbs St, Greensboro, MD 21639

    Welcome to 109 Hobbs Street where a new home can be yours in Kinnamon Meadows in Greensboro, MD. This home is not currently under construction. The Sullivan is a charming 1,219-square-foot, cottage-style ranch home featuring three bedrooms, two bathrooms, and a one-car garage. Just off the foyer, two spacious guest bedrooms and a shared full bathroom offer comfort and privacy for family or

    D.R. Horton Builder
    109 Hobbs St, Greensboro, MD 21639
  • /2

    $225,000

    Coming Soon
    • Land
    • 11.5 Acres
    • $19,565 per Acre

    13006 Oakland Rd, Ridgely, MD 21660

    Approximately 10 acres just outside Ridgely, Md. This property is a subdivide off a larger parcel. Sale cannot be completed until new tax ID is issued and exact acreage known. Surveys are complete and paperwork in progress according to seller. Existing well and septic, condition unknown. Old house on property is a teardown, DO NOT ENTER! This is a land sale. Farmer currently has crops in the

    Michael Shipley Benson & Mangold, LLC.

    13006 Oakland Rd, Ridgely, MD 21660
  • /4

    $426,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 3,372 Sq Ft

    109 Briarwood Cir, Denton, MD 21629

    Welcome to 109 Briarwood Cir in the sought-after Sandy Meadows community of Denton, offering an impressive blend of space, comfort, and flexibility with over 3,300 finished square feet plus an additional 1,525 sq ft unfinished walkout basement ready for your future vision. With its stately two-story presence, beautiful architectural windows, mature landscaping, and inviting curb appeal, this home

    Anissa Hastings Keller Williams Flagship

    109 Briarwood Cir, Denton, MD 21629
  • /23

    $309,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    505 Maryland Ave, Ridgely, MD 21660

    Welcome to 505 Maryland Ave in the heart of charming Ridgely! This beautifully remodeled 3-bedroom, 2-bath rancher is truly move-in ready and offers the perfect blend of modern updates and everyday comfort. Renovated just a few years ago, the home features luxury vinyl plank flooring throughout, stylish soft-close cabinetry, granite countertops, stainless steel appliances, and a bright,

    Heather Brummell Keller Williams Realty

    505 Maryland Ave, Ridgely, MD 21660
  • /30

    $355,000

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

    8140 Haven St, Denton, MD 21629

    This charming ranch-style home, built in 1986, offers a perfect blend of comfort and functionality. Minutes to Tuckahoe Creek boat ramp! With 1,300 sq. ft. of well-designed space, it features three inviting bedrooms and two full bathrooms, including a primary suite with a walk-in closet and a tub/shower. The traditional floor plan is enhanced by built-ins and ceiling fans, creating a cozy

    Mary Haddaway Benson & Mangold, LLC

    8140 Haven St, Denton, MD 21629
  • /67

    $679,000

    • 4 Beds
    • 2.5 Baths
    • 2,744 Sq Ft

    132 Deep Shore Rd, Denton, MD 21629

    Welcome to 132 Deep Shore Rd—an inviting homestead set on more than 3 acres of beautifully maintained gardens, thoughtfully designed outdoor spaces, and versatile outbuildings. From greenhouse and herb beds to a dedicated drying room and casual nooks for lounging, every corner invites you to savor the seasons. Inside, this spacious home offers over 2,700 sq ft with 4 bedrooms and 2.5 baths. An

    Roger Boyce Chesapeake Real Estate Associates, LLC

    132 Deep Shore Rd, Denton, MD 21629
  • /53

    $525,000

    • 2 Beds
    • 1 Bath
    • 1,292 Sq Ft

    5820 Bell Creek Rd, Preston, MD 21655

    Don’t miss this exceptional 20+/- acre working horse farm thoughtfully designed for both functionality and country living. This well-equipped equestrian property offers everything needed for training, boarding, riding, and daily farm operations. The property features a 36’ x 40’ center-aisle barn with 9 stalls, water, electric, and an insulated tack room, along with a 77’ x 36’ metal barn

    Colleen Smith EXP Realty, LLC

    5820 Bell Creek Rd, Preston, MD 21655
  • /40

    $235,000

    • 5 Beds
    • 3 Baths
    • 2,122 Sq Ft

    212 Main St, Preston, MD 21655

    Welcome to this spacious and beautifully maintained property nestled in the peaceful town of Preston. The main residence features 5 generously sized bedrooms and 3 full bathrooms, offering plenty of space for comfortable family living, guests, or multi-generational arrangements. At the heart of the home, you’ll find a large eat-in kitchen, perfect for gathering with family, hosting friends, or

    Ross Muir EXP Realty, LLC

    212 Main St, Preston, MD 21655
  • /8

    $239,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    205 Park Ave, Federalsburg, MD 21632

    **Construction has not yet began, please feel free to drive by the lot. Completion will be for this August 2026!!*** The photos provided in the MLS are for reference purposes only and are intended to reflect the style and quality of similar fixtures, finishes, and features. Actual materials, fixtures, finishes, and selections may vary based on builder availability and final specifications.

    Erene Katris Coldwell Banker Realty

    205 Park Ave, Federalsburg, MD 21632
  • /41

    $259,000

    • 3 Beds
    • 2 Baths
    • 1,787 Sq Ft

    3675 Seaman Rd, Preston, MD 21655

    3 bedroom, 2 bath rancher. Quiet, rural setting that's approximately 15 minutes from Easton and less than 1 hour from MD/DE beaches. Please call with any questions or to schedule your showing.

    Andrew Beaven Wright Real Estate

    3675 Seaman Rd, Preston, MD 21655
  • /78

    $429,000

    Open Sat 11AM - 2PM
    • 4 Beds
    • 2.5 Baths
    • 2,424 Sq Ft

    114 Lister Ln, Ridgely, MD 21660

    Sellers are very motivated and are under contract for their next home. Beautiful colonial nestled in Lister Estates Community! Built in 2006, this detached home features 2,424 square feet above grade, with a new roof installed two years ago, plus a full unfinished basement ideal for storage or future expansion. The main level includes comfortable living spaces, a sunroom, large family room

    Agent Photo

    Dustin Oldfather

    Compass

    (410) 705-7496

    114 Lister Ln, Ridgely, MD 21660
  • /46

    $320,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,250 Sq Ft

    209 W Sunset Ave, Greensboro, MD 21639

    *THE HIGHLIGHTS: 4BR | 2.5BA | True primary suite | Bedroom-level laundry | Original hardwood floors | Pre-blight American Chestnut woodwork & details | Stained glass | Grand staircase | Updated kitchen with chestnut island | Walk-up attic with 2 finished flex rooms | Updated electrical | Newer main-level windows | Owned solar panels | Pellet stove conveys | Wraparound porch | Screened rear porch

    Teal Clise EXP Realty, LLC

    209 W Sunset Ave, Greensboro, MD 21639
  • /52

    $455,000

    • 3 Beds
    • 2.5 Baths
    • 1,720 Sq Ft

    25485 Hignutt Rd, Denton, MD 21629

    Welcome to 25485 Hignutt Rd. in Denton, MD — a completely renovated 3-bedroom, 2.5-bath home situated on nearly a half acre in a peaceful country setting, while still being just minutes from all the shopping, dining, and conveniences Denton has to offer. This beautifully updated and meticulously maintained home is truly move-in ready. Inside, you’ll find durable luxury vinyl plank flooring

    Justin Pokrywka Taylor Properties

    25485 Hignutt Rd, Denton, MD 21629
  • /19

    $260,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,224 Sq Ft

    200 S 2nd St, Denton, MD 21629

    Welcome to this Lovey Cape Cod situated on a corner lot surrounded by a vinyl picket fence. It boasts hardwood flooring through out the main rooms and has strong bones and it is noted for being very easy to heat. You can make your self comfortable while enjoying your favorite beverage on the front screened in porch. Inside a wood burning fireplace enhances the Living Room. This home offers ample

    Barbara Beaudet Brenton Realty Group

    200 S 2nd St, Denton, MD 21629
  • /2

    $459,900

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,839 Sq Ft

    128 Main St, Preston, MD 21655

    Blending warmth, character, and thoughtful updates, this beautifully maintained post-and-beam home offers a truly inviting living experience both inside and out. The spacious main level features all tile flooring, a huge living room anchored by a cozy wood stove, a flexible study/sitting room, and a charming 3-season room. The kitchen and dining combination creates an ideal gathering space with

    Jessica Clark Wilson Realty & Staging LLC

    128 Main St, Preston, MD 21655
  • /2

    $369,000

    Coming Soon
    • 3 Beds
    • 1.5 Baths
    • 1,560 Sq Ft

    401 S 2nd St, Denton, MD 21629

    PICTURES WILL BE POSTED SOON. This charming 2-story colonial home in Denton offers a perfect blend of classic character and modern updates. Featuring 3 bedrooms and 11⁄2 bathrooms, this well-maintained home is conveniently located close to downtown, giving you easy access to local restaurants, shopping, and community events. Inside, you’ll find beautiful hardwood floors that add warmth and

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    401 S 2nd St, Denton, MD 21629
  • /31

    $310,000

    • 3 Beds
    • 1.5 Baths
    • 1,234 Sq Ft

    106 Main St, Preston, MD 21655

    Welcome to this charming and spacious home in Preston offering 3 bedrooms, 1.5 bathrooms, and 2,050 square feet of comfortable living space. Freshly painted throughout, this home features beautiful hardwood flooring that adds warmth and timeless character. With generous living areas and a move-in-ready feel, this property blends comfort and style while providing plenty of space for everyday

    Shay Prattis Keller Williams Realty

    106 Main St, Preston, MD 21655
  • /41

    $249,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    311 Maple Ave, Federalsburg, MD 21632

    Coming Soon! Prepare to be impressed by this stunning, top-to-bottom transformation. This home has been thoughtfully expanded with a brand-new second floor featuring a private primary suite, a dedicated laundry room, and a total of 3 spacious bedrooms and 2 modern baths. The main level shines with all-new LVP flooring, a modern kitchen boasting sleek new cabinetry, granite countertops, and

    Valerie Brown Coldwell Banker Realty

    311 Maple Ave, Federalsburg, MD 21632

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