146

Caroline County MD Homes for Sale

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  • /19

    $435,000

    • 3 Beds
    • 2 Baths
    • 2,408 Sq Ft

    13166 Oakland Rd, Ridgely, MD 21660

    Possibilities! This Caroline County 3-bedroom 2 bath Victorian sitting on almost 4 acres with fencing and plenty of usable buildings in a country setting. Nearby points of interest include Tuckahoe state park with equestrian trails, hiking trails, even a lake to paddle or fish. Gooden Airpark is just down the road along with a few boat ramps to the Choptank River. The property offers several

    BRIAN MORRIS The Land Group

    13166 Oakland Rd, Ridgely, MD 21660
  • /8

    $130,000

    • Land
    • 1.01 Acres
    • $128,713 per Acre

    707 W Sunset Ave, Greensboro, MD 21639

    Several individual parcels on Sunset, Cosden and Harold Streets. One parcel has a large 50' x 70' Morton style building, town water is on site and sewer is available. Any interested buyer should perform their own suitable level of due diligence.

    BRIAN MORRIS The Land Group

    707 W Sunset Ave, Greensboro, MD 21639
  • /15

    $299,000

    $16K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    506 Pintail St, Greensboro, MD 21639

    Nearly new ranch style home with large front porch. Three bedrooms and two full baths plus spacious laundry room enhance this home. Large kitchen with center island with stainless appliances and granite countertops are a focal point of this open floor plan. Move in ready and waiting for a new family!

    Bonnie Johnson Keller Williams Realty

    506 Pintail St, Greensboro, MD 21639
  • /75

    $1,150,000

    • 4,368 Sq Ft

    6354 Statum Rd, Preston, MD 21655

    This wonderful 20 acre property is a horse person’s dream facility. Located in a rural setting, northeast of Preston Maryland. The farm is highlighted by a well-constructed and maintained 75’ x 225’ indoor riding arena, and an 8 stall concrete center aisle horse barn. The barn includes a heated tack room, wash stall with hot water, grooming stall, loft, and overhangs for great ventilation.

    A. John Price Patterson-Schwartz-Middletown

    6354 Statum Rd, Preston, MD 21655
  • /62

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    1010 S 2nd St, Denton, MD 21629

    Nestled on the edge of town, 1010 S 2nd Street delivers the convenience of in-town living without in-town taxes. Situated on 1.06 beautifully landscaped acres with mature plantings, this 3-bedroom, 2-bath home offers a spacious feel inside and out. Interior features include hardwood, LVP, and tile flooring, along with a cozy pellet stove fireplace insert for efficient heating, complemented by hot

    Roger Boyce Chesapeake Real Estate Associates, LLC

    1010 S 2nd St, Denton, MD 21629
  • /30

    $259,900

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    325 Carter Ave, Denton, MD 21629

    The joy of one level living!! This home is in Move-in ready condition. Nice size 2 Bedroom 1 Full Bath. Level lot with Patio for enetertaining. Conveniently located within town limits. Shop, parks, restuarants, Brewery.Public Boat ramp to the Choptank River less than a mile.

    Kathleen Brenton Brenton Realty Group

    325 Carter Ave, Denton, MD 21629
  • /15

    $450,000

    • 4 Beds
    • 2 Baths
    • 2,111 Sq Ft

    27329 Jenny Hye Ln, Marydel, MD 21649

    Situated on a 1.51 acre lot, backing to woods, this four Bedroom, 2 full bath home's interior has been completely renovated! Kitchen with eat -in area has been updated with new cabinetry, granite countertops & s/s appliances, Separate dining room for those wanting a more formalized area or can be used as a den, Living room with wood burning fireplace leads to expansive family room with access to

    Kathleen May Synergy Realty

    27329 Jenny Hye Ln, Marydel, MD 21649
  • /30

    $239,900

    $35K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    205 N Academy St, Greensboro, MD 21639

    Welcome to this fully remodeled ranch, perfectly situated on a level lot on a quiet street. The showstopper kitchen features white shaker cabinets with dovetailed soft-close drawers, white quartz countertops, tile backsplash, and stainless steel appliances. Every inch of this home has been thoughtfully updated with new LVP flooring, plush carpet, fresh paint, and new lighting throughout. The

    Lee Wolff FSBO Broker

    205 N Academy St, Greensboro, MD 21639
  • /37

    $299,000

    • 3 Beds
    • 1 Bath
    • 1,222 Sq Ft

    7192 American Corner Rd, Denton, MD 21629

    Come make this updated and move in ready rancher your new home. Considerable improvements have been made over the last two years to include the following. This home has a new deep well, new septic system, new tankless propane water heater, new washer/dryer. new range and refrigerator, new roof, new siding, new hvac, renovated bathroom, new flooring, fresh paint, new privacy and chain link fencing

    Andrew Beaven Wright Real Estate

    7192 American Corner Rd, Denton, MD 21629
  • /4

    $155,000

    • 1 Bed
    • 1 Bath
    • 512 Sq Ft

    26355 Marydel Rd, Marydel, MD 21649

    House is of little to no value, existing well and septic. This house includes an additional parcel of 7 acres, tax id, 0601012428 for a total of 7.27 acres. Property being SOLD AS IS.

    George Thompson Long & Foster Real Estate, Inc.

    26355 Marydel Rd, Marydel, MD 21649
  • /11

    $3,700,000

    8019 Patten Rd, Denton, MD 21629

    Poultry farm features a total of 60.57 acres (40 acres tillable, 8.5 acres wooded, 1.5-acre retention pond) and a 40x72 shop that has garage parking and a separate space that could be finished for permanent living. Located approx. 5 miles from the DE line. Expired site evaluation-no septic on property.

    Tambra Reagan CALLAWAY FARNELL AND MOORE

    8019 Patten Rd, Denton, MD 21629
  • /50

    $595,000

    • 5 Beds
    • 2.5 Baths
    • 2,920 Sq Ft

    24276 Asbury Dr, Denton, MD 21629

    Nestled in the shadows of the Choptank River is a meticulously maintained home in the water-privileged neighborhood of Asbury. Beautiful Expansive lot size gives you the privacy needed within a walkable neighborhood. The flat level lot opens up future pool and other amenity possibilities. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    24276 Asbury Dr, Denton, MD 21629
  • /94

    $380,000

    • 3 Beds
    • 2 Baths
    • 1,904 Sq Ft

    28440 Bloomery Rd, Federalsburg, MD 21632

    If you've been searching for a property that offers acreage, privacy, and plenty of room to grow, this is the one you've been waiting for! Nestled on 3.80 wooded acres, this ranch-style home offers approximately 1,904 square feet of comfortable living space, featuring 3 bedrooms, 2 full baths, and two versatile bonus rooms that can easily serve as a home office, hobby room, playroom, guest space,

    Sean Steward Century 21 Home Team Realty

    28440 Bloomery Rd, Federalsburg, MD 21632
  • /40

    $285,000

    Open Sat 10AM - 12PM
    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft

    103 Williamson St, Preston, MD 21655

    Welcome home to this beautifully remodeled 3-bedroom, 2-bath home situated on nearly a half-acre lot in the charming town of Preston. This move-in ready property features beautiful hardwood floors, a spacious kitchen with abundant cabinetry, granite countertops, new appliances, and new carpet throughout. The inviting living room showcases gleaming hardwood floors and a cozy gas fireplace,

    Dawn Hubbard Keller Williams Select Realtors of Cambridge

    103 Williamson St, Preston, MD 21655
  • /20

    $205,000

    $5K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 812 Sq Ft

    310 Park Ave, Federalsburg, MD 21632

    This charming farmhouse-style home, built in 1904 has undergone a major renovation in 2026. With 812 square feet of thoughtfully designed living space, this delightful residence features two cozy bedrooms and one and a half bathrooms, making it an ideal retreat for those seeking comfort and style. Step inside to discover a beautifully updated interior adorned with luxury vinyl plank flooring,

    Cheryl Knotts Chesapeake Real Estate Associates, LLC

    310 Park Ave, Federalsburg, MD 21632
  • /6

    $360,000

    $40K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,128 Sq Ft

    26784 Bilbrough Rd, Goldsboro, MD 21636

    Welcome to your private slice of Eastern Shore living in Goldsboro. Set on 4.7 secluded acres, this 2022-built home offers the space, comfort, and modern features today's market demands. With over 2,100 square feet, 4 bedrooms, and 2 full baths, the layout is open, bright, and designed for seamless everyday living. Step inside to a spacious floor plan that flows effortlessly from room to

    Sandra Bradley Keller Williams Select Realtors of Easton

    26784 Bilbrough Rd, Goldsboro, MD 21636
  • /2

    $32,500

    • Land
    • 30,056 Sq Ft
    • $47,101 per Acre

    0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660

    Just next to the quaint town of Ridgely, this .69 acre lot also comes with a bonus lot highlighted in photos. Buy and hold as an investment or see if you can perc.

    Michael Rosendale Rosendale Realty

    0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660
  • /4

    $21,000

    $14K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,024 Sq Ft

    204 Academy Ave, Federalsburg, MD 21632

    Investor special! This property is being sold AS-IS and is priced for land value or a full renovation. The existing structure requires extensive repairs or complete tear-down—ideal for experienced builders, contractors, or savvy investors looking for a project. Buyer to verify zoning, permits, potential use. Buyer Broker/Agent and/or Buyer must do their own due diligence to verify if the existing

    Mike Dunn Keller Williams Realty Delmarva

    204 Academy Ave, Federalsburg, MD 21632
  • /2

    $60,000

    • Land
    • 1 Acre
    • $60,000 per Acre

    27286 Willin Ln, Federalsburg, MD 21632

    Private 1-acre wooded lot with deeded access via a dirt road. Enjoy a secluded setting surrounded by nature, perfect for those looking to get away from it all. Great opportunity for a future homesite or recreational use (subject to county approvals). Motivated seller—bring all reasonable offers!

    Janet Todd Harlan C. Williams Co.

    27286 Willin Ln, Federalsburg, MD 21632
  • /13

    $109,000

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    4471 Harmony Rd, Preston, MD 21655

    Discover the potential in this ranch-style home situated on a spacious lot in Caroline County. This property is ready for renovation and offers a great opportunity to update and customize to your vision. Major improvements have already been completed, including a newer roof and updated windows, providing a solid starting point for your renovation plans. The home is served by a private well and

    Norman Domingo XRealty.NET LLC

    4471 Harmony Rd, Preston, MD 21655
  • /47

    $755,000

    • 3 Beds
    • 2 Baths
    • 2,504 Sq Ft

    3769 Bradley Rd, Federalsburg, MD 21632

    This is your farmette dream come true! This beautiful 3 bed, 2 full bath home is situated on 6+ acres of partially fenced in land, has a barn with a tack room, a large screened-in back porch, a 2 car garage and an in-ground saltwater pool. The barn features 3 stalls, a hay loft with elevator, washroom, a tack room with a closet and shelves for storage. The water to the barn is sourced from a 290

    Sarah Robins Coldwell Banker Realty

    3769 Bradley Rd, Federalsburg, MD 21632
  • /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
  • /50

    $465,000

    • 3 Beds
    • 2 Baths
    • 2,240 Sq Ft

    23118 Tuckahoe Springs Dr, Denton, MD 21629

    Eastern Shore living at its finest! Nestled in the desirable Tuckahoe Springs subdivision, this beautifully maintained home offers the perfect blend of comfort, style, and serene outdoor living.Step inside to an inviting foyer that leads to a dedicated laundry area and an expansive, well‑appointed kitchen featuring cabinetry galore, upgraded stainless‑steel appliances, and quartz

    Amanda Morgan Brenton Realty Group

    23118 Tuckahoe Springs Dr, Denton, MD 21629
  • /25

    $334,900

    $5K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,440 Sq Ft

    147 Mill St, Preston, MD 21655

    Well Maintained 4 Bed 2 Full Bath Cape Cod. Large Eat-in Kitchen w/ Stainless Steel Appliances, Granite Countertops and Center Island!Nice Size Family Room. Outdoors feature a Large Shed with Heat and Air (currently used as a very nice office) , Separate Shed for storage at the back of Spacious level Lot. Patio for entertaining and more... Home is less than 1 Mile to Choptank River Landing!

    Kathleen Brenton Brenton Realty Group

    147 Mill St, Preston, MD 21655
  • /17

    $414,499

    $15K PRICE DROP
    • 6 Beds
    • 2.5 Baths
    • 2,934 Sq Ft

    304 Tidewater Cir, Preston, MD 21655

    LOVELY Tidewater Farms home with a light, open layout and plenty of space to enjoy. The main level features a spacious breakfast room, open kitchen and great room with a center island, eat-at bar, and gas fireplace. There is also a 19' x 15' bonus room and convenient upstairs laundry.The primary suite offers walk-in closets, a soaking tub, separate shower, and double sink vanity. Outside,

    Judah Fashe Samson Properties

    304 Tidewater Cir, Preston, MD 21655
  • /35

    $265,000

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

    530 Vaughn Ave, Greensboro, MD 21639

    **Seller is offering $7,500 towards buyers closing costs with an acceptable offer** Welcome home to this beautifully updated 3-bedroom, 2.5-bath home built by Gemcraft Homes in 2002. Freshly painted throughout in 2026, this move-in-ready home also features brand-new luxury vinyl plank flooring on the main level and new carpet throughout the second floor, offering a fresh, modern feel from the

    Hunter Geary Hyatt & Company Real Estate, LLC

    530 Vaughn Ave, Greensboro, MD 21639
  • /14

    $282,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft

    Curtis Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms and two bathrooms. As you enter the home through the front porch, this thoughtfully designed home has a grand open concept living area that leads into the spacious kitchen. To the right, a long, main hallway allows for the two guest bedrooms and guest bathroom to be separate from the living areas of the home. Along

    D.R. Horton Builder
    103 Park Ave Unit 36203276, Greensboro, MD 21639
  • /24

    $229,000

    $6K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    122 Julie Ln, Federalsburg, MD 21632

    Welcome to this beautifully maintained newer town home that has been virtually staged was built in late 2025, in the charming Riverwalk community of Federalsburg. Offering 3 bedrooms, 2.5 bathrooms, and modern construction, this home combines today's sought-after finishes with the warmth and small-town charm that make Maryland's Eastern Shore such a desirable place to call home. Close to

    Donna Hollifield Remax Vision

    122 Julie Ln, Federalsburg, MD 21632
  • /67

    $659,000

    $20K PRICE DROP
    • 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

    Roger Boyce Chesapeake Real Estate Associates, LLC

    132 Deep Shore Rd, Denton, MD 21629
  • /25

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    113 Chamber St, Preston, MD 21655

    Welcome to 113 Chamber Street in the heart of Preston! This well-maintained single-story home offers comfortable living on a spacious 0.42-acre lot within town limits. Featuring 2 full bathrooms, a practical floor plan, and a large detached garage with approximately 880 square feet of space, this property provides plenty of room for parking, storage, hobbies, or a workshop. Enjoy outdoor living

    Heather Brummell Keller Williams Realty

    113 Chamber St, Preston, MD 21655
  • /27

    $330,000

    • 3 Beds
    • 2.5 Baths
    • 1,212 Sq Ft

    104 Chambers St, Federalsburg, MD 21632

    Ready to own without the stress? Move in and start your life, not your renovation. This fully renovated home is one your friends will be drooling over. The kitchen steals the show: soft-close navy cabinets with gold hardware and quartz countertops, stainless steel appliances, a deep kitchen sink, stylish floating shelves, and a crisp white tile backsplash. It's the kind of space that makes

    Kaitlyn Collins Benson & Mangold, LLC

    104 Chambers St, Federalsburg, MD 21632
  • /44

    $575,000

    • 4 Beds
    • 2.5 Baths
    • 2,426 Sq Ft

    22733 Squire Ln, Queen Anne, MD 21657

    You'll love this custom home nestled on 2.13 private acres, offering over 2,500 square feet of thoughtfully designed living space with 4 bedrooms and 2.5 baths. The open floor plan is highlighted by rich Brazilian hardwood floors, cathedral ceiling, and a welcoming great room anchored by a dramatic floor-to-ceiling brick fireplace.The spacious kitchen opens seamlessly to the great room

    Jimmy White Long & Foster Real Estate, Inc.

    22733 Squire Ln, Queen Anne, MD 21657
  • /74

    $600,000

    Coming Soon
    • 6 Beds
    • 3.5 Baths
    • 3,592 Sq Ft

    11592 Holly Rd, Ridgely, MD 21660

    Welcome to 11592 Holly Road in Ridgely, MD! This spacious 6-bedroom, 3.5-bath home offers plenty of room inside and out, with a flexible layout to fit a variety of needs.Inside, you'll find a bright kitchen with premium appliances, a comfortable living room with a gas fireplace, and a primary suite featuring a separate sitting area and attached office. The home also includes an in-law

    Jarnell Foster Samson Properties

    11592 Holly Rd, Ridgely, MD 21660
  • /59

    $1,350,000

    $150K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,358 Sq Ft

    23071 Tuckahoe Springs Dr, Denton, MD 21629

    Price Improvement Beautifully positioned along the deep protected waters of the Tuckahoe, this exceptional residence has been transformed through an extensive renovation that blends timeless design with comfortable waterfront living. Every improvement was carefully planned, resulting in a home that feels as inviting as it is impressive. The heart of the home is the custom kitchen, where blue

    Sydney Johnson Cohee Sharon Real Estate P.C.

    23071 Tuckahoe Springs Dr, Denton, MD 21629
  • /29

    $700,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 4,580 Sq Ft

    14236 Drapers Mill Rd, Greensboro, MD 21639

    STOP, LOOK, and READ...this may be exactly the property you’ve been searching for!! RESIDENTIAL / COMMERCIAL OPPORTUNITY – Zoned C-2, this versatile multi-use property offers endless possibilities! Relocate your business, expand to a second location, or launch your next venture while enjoying the convenience of living and working side by side on this incredible 2+ acre property. This unique

    Karen Clark Clark & Co Realty, LLC

    14236 Drapers Mill Rd, Greensboro, MD 21639
  • /74

    $599,900

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,938 Sq Ft

    23130 Sparks Rd, Ridgely, MD 21660

    Robert Walker McClain-Williamson Realty, LLC

    23130 Sparks Rd, Ridgely, MD 21660
  • /60

    $525,000

    • 3 Beds
    • 3 Baths
    • 3,088 Sq Ft

    22005 Main St, Hillsboro, MD 21641

    PLEASE NOTE that the Owner has listened to the current market, Price has been reduced to $525,000. It is a property of beautifully preserved quality on ¾ of an acre in an urban setting. Most unusual! When compared to equivalent historic properties it is now very competitively priced!This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful

    Nancy McGuire Maryland Heritage Properties

    22005 Main St, Hillsboro, MD 21641
  • /9

    $79,000

    • Land
    • 3.05 Acres
    • $25,902 per Acre

    10440 Burrsville Branch Rd, Denton, MD 21629

    Rare opportunity to own over 3 acres in a peaceful rural setting just outside of Denton and approximately one mile from the Maryland/Delaware state line. Close to Delaware Beaches and Tax Free Shopping. This partially wooded homesite backs to open farmland, offering privacy and picturesque country views. The property provides an ideal setting for a custom home, subject to the installation of a

    Deborah Callahan Benson & Mangold, LLC

    10440 Burrsville Branch Rd, Denton, MD 21629
  • /20

    $170,000

    • 2 Beds
    • 1 Bath
    • 744 Sq Ft

    6140 Laurel Grove Rd, Denton, MD 21629

    Escape the noise and reconnect with what matters most. Nestled on a peaceful 1-acre country setting surrounded by mature trees and open skies, this charming cottage offers the perfect opportunity to embrace the simplicity and serenity of tiny home living. Whether you’re searching for a full-time residence, a weekend retreat, or a place to slow down and enjoy nature, this property delivers a

    Andrea Harrington Compass

    6140 Laurel Grove Rd, Denton, MD 21629
  • /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

Showing Results 81 - 120, Page 3 of 4

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