160

Caroline County MD Homes for Sale

Section Image Section Image Section Image
  • /49

    $315,000

    • 4 Beds
    • 2 Baths
    • 2,774 Sq Ft

    111 Maple Ave, Greensboro, MD 21639

    Step into the timeless charm of this beautifully maintained circa-1880 home, where historic elegance meets thoughtful modern updates. Offering over 2,774 square feet of living space, this exceptional residence features 4 spacious bedrooms, 2 full bathrooms, and an abundance of original architectural character that has been lovingly preserved while incorporating today's modern conveniences. From

    Barbara McCaffrey Redfin Corp

    111 Maple Ave, Greensboro, MD 21639
  • /23

    $224,900

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    304 Academy Ave, Denton, MD 21629

    Why rent when you can own for less?? This home has 3 bedrooms and one bath. Eat-in Kitchen, Large Family Room, nicely landscaped and fenced back yard. Off Street parking Newer HVAC, Kitchen with lots of cabinets, Laundry Room with Washer and Dryer and lots of extra space- Public Water and Sewer. Within walking distance to Resaturants, Parks and Shopping. Come Check this Out! Wont Last.

    Kathleen Brenton Brenton Realty Group

    304 Academy Ave, Denton, MD 21629
  • /48

    $374,900

    Open Sat 2PM - 4PM
    • 4 Beds
    • 2.5 Baths
    • 2,176 Sq Ft

    8548 Dogwood Blossom Ln, Denton, MD 21629

    Nestled along a private road in a peaceful, tucked-away setting, this well-maintained Colonial offers the perfect blend of privacy, space, and convenience. Situated on more than 1.2 acres, the property backs to mature woods, providing beautiful wooded views and a serene backdrop to everyday living. The home needs only minor cosmetic updates, making it an excellent opportunity to add your own

    Barbara McCaffrey Redfin Corp

    8548 Dogwood Blossom Ln, Denton, MD 21629
  • /75

    $1,150,000

    • 4,368 Sq Ft

    6354 Statum Rd, Preston, MD 21655

    A. John Price Patterson-Schwartz Real Estate

    6354 Statum Rd, Preston, MD 21655
  • /23

    $288,990

    New Construction $16K PRICE DROP
    • 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
  • /29

    $409,500

    New Construction Open Sun 12PM - 2PM
    • 4 Beds
    • 2 Baths
    • 1,628 Sq Ft

    5 Sunrise Ave, Ridgely, MD 21660

    OPEN HOUSE | Sunday, July 19 | 12:00–2:00 PM Welcome to 5 Sunrise Avenue, a beautifully crafted Lomaxx Custom Homes rancher that’s complete and move in ready! This thoughtfully designed home offers 4 bedrooms, 2 bathrooms, and a spacious 2-car garage, blending modern style with everyday comfort. Inside, you’ll find an open layout featuring luxury vinyl plank flooring, quartz countertops,

    Crystal Smith RE/MAX Executive

    5 Sunrise Ave, Ridgely, MD 21660
  • /30

    $274,900

    • 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
  • /2

    $274,990

    New Construction $12K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft

    125 Hobbs St, Greensboro, MD 21639

    Discover 125 Hobbs Street, a new home under-construction in the quaint Kinnamon Meadows community of Greensboro, MD. The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms, two bathrooms, and a two-car driveway. 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

    D.R. Horton Builder
    125 Hobbs St, Greensboro, MD 21639
  • /83

    $779,000

    Coming Soon
    • 5 Beds
    • 5 Baths
    • 3,816 Sq Ft

    8821 Dorothy Ln, Denton, MD 21629

    " Diamond in the Rough" This property is being sold to settle an estate and no repairs will be made. Offering considerable upside potential, this private 5 bedroom, 5 bath home is tucked away on the Choptank River in the community of Asbury.

    Andrew Beaven Wright Real Estate

    8821 Dorothy Ln, Denton, MD 21629
  • /28

    $405,000

    • 3 Beds
    • 2 Baths
    • 1,740 Sq Ft

    25214 Smith Landing Rd, Denton, MD 21629

    Waterfront parcel on the Choptank River! 3 (possibly 4) bedroom, 2 full bath 2-story home on a 3.15 +/- acre fee simple parcel. Numerous shade trees and perennial plantings surround the home. Two (2) outbuildings await your vision. Located approximately 15 miles from the Harrington Raceway & Casino, 30 miles from the Bay Bridge and 50 miles from local beach resorts. Owner say to bring

    John Fifer Brokers Realty Group, LLC

    25214 Smith Landing Rd, Denton, MD 21629
  • /40

    $285,000

    • 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
  • /2

    $95,000

    • 3 Beds
    • 1.5 Baths
    • 1,408 Sq Ft

    310 E Central Ave, Federalsburg, MD 21632

    Excellent investment opportunity! Over 1/4 acre lot. Home needs TLC. Partial owner financing available. Call for more info. This deal will not last long. Grab it while you have the chance!

    Raphael Szendro R&R Executive Realty

    310 E Central Ave, Federalsburg, MD 21632
  • /8

    $390,000

    Coming Soon
    • 3 Beds
    • 1 Bath
    • 936 Sq Ft

    4455 Smithville Rd, Federalsburg, MD 21632

    This charming ranch-style home, built in 2004, offers a cozy retreat on over 11 acres of serene land, adjoining the picturesque Marshyhope Creek with 3800 acres of Idlewild WMA just across the creek. Inside, discover a traditional floor plan featuring three inviting bedrooms and a country-style kitchen perfect for gatherings. Enjoy the warmth of luxury vinyl plank and carpet flooring throughout.

    Nathan Murray RE/MAX Executive

    4455 Smithville Rd, Federalsburg, MD 21632
  • /47

    $425,000

    • 3 Beds
    • 1.5 Baths
    • 1,356 Sq Ft

    21370 Skeleton Creek Rd, Preston, MD 21655

    Very rustic and private 3 bedroom, 1 and a 1/2 bath log cabin on 15 private wooded acres. There is a large building and a sun porch overlooking a stream running through the property. Excellent hunting property for whitetail deer and turkey!

    Henry Gibbons-Neff Meredith Fine Properties

    21370 Skeleton Creek Rd, Preston, MD 21655
  • /74

    $479,000

    • 3 Beds
    • 3 Baths
    • 2,506 Sq Ft

    104 Charlotte Ave, Federalsburg, MD 21632

    Custom Brick Rancher with 2500 sq ft of living space sitting on over half an acre just outside of downtown Federalsburg overlooking Chambers Park is waiting for you to come see to appreciate. Owners have done many improvements and upgrades to the property, but left some of it's timeless charm. New carpet has been installed on the porch, breakfast nook, and family room July 2026, new windows 2026,

    Shelby Roney Benson & Mangold, LLC

    104 Charlotte Ave, Federalsburg, MD 21632
  • /14

    $279,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    25399 Golt Farm Ln, Goldsboro, MD 21636

    Well maintained Rancher on 2.76 Acres. 2 Bedrooms, 1 Bath, Kitchen with dining room, living room with brick chimney and hearth, 24x30 Delmarva Pole Building with water, 220 &110 electric and 6in. concrete floor. There are 2 additional parcels for sale that adjoin this property potentially adding another 10.75 acres for a combined total of 13.5+/- acres.

    Diane Wenk Wright Real Estate

    25399 Golt Farm Ln, Goldsboro, MD 21636
  • /2

    $25,000

    • Land
    • 22,651 Sq Ft
    • $48,077 per Acre

    10291 Bridge St, Denton, MD 21629

    1/2 ACRE LOT IN DENTON. THIS PROPERTY WAS PURCHASED THROUGH TAX SALE, SELLER IS BRYNN, LLC.

    Henry Gibbons-Neff Meredith Fine Properties

    10291 Bridge St, Denton, MD 21629
  • /2

    $325,000

    Coming Soon
    • 4 Beds
    • 2 Baths
    • 1,539 Sq Ft

    306 Sunrise Ave, Ridgely, MD 21660

    Charming & Move-In Ready in Ridgely! This 4-bedroom, 2-full-bath home is priced to sell and ready for its next owner. New $25,000 roof with 50-year transferable warranty! Situated on a spacious corner lot in the friendly town of Ridgely, MD, the property includes 2 utility sheds for extra storage and plenty of parking with off-street spaces in both the front and rear, plus additional on-street

    Vincent De Lorenzo Samson Properties

    306 Sunrise Ave, Ridgely, MD 21660
  • /28

    $699,000

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

    14540 Drapers Mill Rd, Goldsboro, MD 21636

    Searching for your own private oasis with endless possibilities? Welcome to a rare 16.29-acre offering made up of four separate parcels, thoughtfully improved and ready for whatever vision you bring. Whether you dream of a hobby farm, a multi-use homestead, or a private retreat, this property delivers space, versatility, and infrastructure you won’t find anywhere else. Across the acreage you’ll

    Amanda Morgan Brenton Realty Group

    14540 Drapers Mill Rd, Goldsboro, MD 21636
  • /74

    $624,900

    • 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
  • /22

    $467,900

    • 3 Beds
    • 4 Baths
    • 2,713 Sq Ft

    202 N Central Ave, Ridgely, MD 21660

    Charming Victorian home in the heart of Ridgely, ideally situated on a picturesque, tree-shaded corner lot. This timeless property offers classic character, curb appeal, and a prime location close to local amenities. An expansive wraparound front porch sets the stage for this beautiful home, featuring a gracious entryway, stunning columned foyer, and gleaming hardwood floors that enhance its

    Marcia Rostien Long & Foster Real Estate, Inc.

    202 N Central Ave, Ridgely, MD 21660
  • /2

    $299,990

    New Construction $8K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    111 Hobbs St, Greensboro, MD 21639

    Explore 111 Hobbs Street, a new home under construction in the quaint Kinnamon Meadows community of Greensboro, MD. The Helena is an inviting 1,460 square foot cottage-style ranch home that offers four bedrooms, two bathrooms, and a one-car garage. The long, welcoming foyer of this home allows for the three guest bedrooms and guest bathroom to be separate from the living areas of the home. The

    D.R. Horton Builder
    111 Hobbs St, Greensboro, MD 21639
  • /4

    $225,000

    • Land
    • 8.7 Acres
    • $25,862 per Acre

    12191 Knife Box Rd, Greensboro, MD 21639

    Large wooded homesite with existing home and barn on property. Existing home was built in 1987, 2,476sq feet 4 bedroom rancher with in ground pool to rear. Large barn was used as a horse stable. Home has been vacant for over a decade and become dilapidated. Major remodel or tear down needed. Septic system and well located on property, unknown if operational. Property is located down long

    Todd McGill ExecuHome Realty

    12191 Knife Box Rd, Greensboro, MD 21639
  • /55

    $355,000

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    306 Caroline Ave, Ridgely, MD 21660

    Charming updated Farmhouse style home with hardwood floors throughout and tiled bathrooms. The open kitchen features quartz countertops, a center island for extra prep space and casual dining, stainless steel appliances, and a tile backsplash. The first floor includes a full bath with a tiled walk-in stall shower, plus a separate laundry/mud room. Dual-zone heating and air for year-round comfort.

    Roger Boyce Chesapeake Real Estate Associates, LLC

    306 Caroline Ave, Ridgely, MD 21660
  • /20

    $309,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    510 Lincoln St, Denton, MD 21629

    Discover effortless one‐level living in this newly constructed three-bedroom, two-bathroom rancher, completed in 2024 and perfectly positioned in the center of downtown Denton. Modern design, thoughtful upgrades, and an open, airy layout make this home stand out from the moment you step inside. The open-concept living, dining, and kitchen area creates a warm and welcoming flow—ideal for everyday

    Amanda Morgan Brenton Realty Group

    510 Lincoln St, Denton, MD 21629
  • /43

    $424,900

    • 3 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    509 S 2nd St, Denton, MD 21629

    Welcome to one of Denton’s most enchanting hidden retreats — a beautifully restored and thoughtfully updated 1941 Cape Cod tucked among towering trees, lush gardens, and comfortable living spaces in the heart of town.Lovingly renovated while preserving its original charm and architectural character, the main residence offers timeless warmth and understated elegance throughout. Rich hardwood

    Judith Germain Benson & Mangold, LLC

    509 S 2nd St, Denton, MD 21629
  • /35

    $265,000

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

    530 Vaughn Ave, Greensboro, MD 21639

    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 moment you step inside. The main level offers a bright and inviting living room that

    Hunter Geary Hyatt & Company Real Estate, LLC

    530 Vaughn Ave, Greensboro, MD 21639
  • /20

    $210,000

    • 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
  • /59

    $1,500,000

    • 4 Beds
    • 3 Baths
    • 3,358 Sq Ft

    23071 Tuckahoe Springs Dr, Denton, MD 21629

    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 marble countertops,

    Sydney Johnson Cohee Sharon Real Estate P.C.

    23071 Tuckahoe Springs Dr, Denton, MD 21629
  • /50

    $469,900

    • 4 Beds
    • 2.5 Baths
    • 2,488 Sq Ft

    9472 Quail Run Rd, Denton, MD 21629

    Denton - 4 bedroom home! This property offers an incredible opportunity to own a home with fantastic features, major mechanical updates, and no HOA! Inside, you will find a traditional layout highlighted by a large country kitchen featuring new countertops and an island. The formal dining room, den (with woodstove) and living room give ample opportunities for flex space. The primary bedroom

    Valerie Brown Coldwell Banker Realty

    9472 Quail Run Rd, Denton, MD 21629
  • /23

    $215,000

    • Studio
    • 2,532 Sq Ft

    1 Central Ave, Ridgely, MD 21660

    Welcome to 1 Central Ave, perfectly positioned in the heart of downtown Ridgely! This versatile mixed‐use building offers endless potential with both commercial and residential spaces under one roof. The first‐floor commercial unit features an inviting open foyer/reception area, four private office spaces, a half bathroom, and a spacious office/conference room toward the rear—ideal for

    Amanda Morgan Brenton Realty Group

    1 Central Ave, Ridgely, MD 21660
  • /36

    $299,000

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,800 Sq Ft

    210 W 2nd St, Ridgely, MD 21660

    Welcome to 210 W. 2nd Street in Ridgely, where modern construction meets small-town charm. Built in 2026, this beautifully designed 4-bedroom, 2-bath home offers approximately 1,800 square feet of thoughtfully designed living space, perfect for today's lifestyle.Step inside to discover bright, open living areas ideal for everyday living and entertaining. The functional floor plan provides

    Kat Thompson Benson & Mangold, LLC.

    210 W 2nd St, Ridgely, MD 21660
  • /17

    $295,000

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

    1043 Camp Rd, Denton, MD 21629

    NICE COUNTRY RANCHER IN A WOODED PARADISE CLOSE TO ALL OF THE TOWN AMENITIES. LARGE FAMILY ROOM WITH VAULTED CEILING AND SURROUND SOUND WITH A WOOD BURNING BRICK FIREPLACE. AN ENCLOSED PATIO WITH PRIVACY. LARGE YARD SURROUNDED BY TREES. BOTH AN ATTACHED GARAGE AND A DETACHED GARAGE. REAR DECK FOR ENTERTAINING. PLENTY OF ROOM FOR YOUR FAMILY ACTIVITIES. THIS IS A MUST-SEE PROPERTY. ESTATE PROPERTY

    James Patrick Century 21 Harbor Realty

    1043 Camp Rd, Denton, MD 21629
  • /24

    $235,000

    • 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
  • /39

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,414 Sq Ft

    504 Main St, Goldsboro, MD 21636

    Welcome to this turn-key, eco-friendly rancher offering single-level living and a modern, open layout. Step inside to a fluid floor plan featuring striking dark wood-look laminate flooring throughout. The spacious living room features a designer green accent wall and flows seamlessly into the country kitchen and dining combination. The kitchen boasts sleek white cabinetry, stainless steel

    Dustin Parker The Parker Group

    504 Main St, Goldsboro, MD 21636
  • /2

    $330,000

    Coming Soon
    • 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
  • /30

    $52,000

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

    American Corner Rd, Denton, MD 21629

    5.20 Acres Wooded Land on Paved American Corner Road in Caroline County, MarylandCash Price: $52,000Reservation Fee: $900 non-refundable reservation fee secures this property. Reservation fee will be counted toward purchase price or down payment.With your Purchase You Get:1. A Deed in Your Own Name2. 4. NO Closing Fees if you Close Directly In-House with our BBB A+

    Elegment Land Elegment.com

    American Corner Rd, Denton, MD 21629
  • /22

    $399,000

    $10K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,624 Sq Ft

    13790 Drapers Mill Rd, Greensboro, MD 21639

    4 bedroom 2 bath rancher on 3.6 spacious acres on the headwaters of the Choptank.

    Scott Judy Coldwell Banker Waterman Realty

    13790 Drapers Mill Rd, Greensboro, MD 21639
  • /22

    $339,500

    $5K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft

    2691 Lorraine Ave, Federalsburg, MD 21632

    Discover 2691 Lorraine Ave, Federalsburg, MD 21632. This Cape Cod residence offers a spacious layout situated on over an acre of land at the end of a quiet cul-de-sac. The property features 4 beds, 2 baths, and a welcoming kitchen where all built in appliances stay. Enjoy a large living area with a fireplace and an entry-level bedroom for convenience. Step out onto the back deck to appreciate the

    Norman Domingo XRealty.NET LLC

    2691 Lorraine Ave, Federalsburg, MD 21632
  • /16

    $234,900

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

    163 Riverwalk Terrace, Federalsburg, MD 21632

    This end unit has units on the left side but no units on the right side, offering more quietness and privacy. This beauty has comfort and "home" written all over. Featuring 3 nice-sized bedrooms; a convenient half-bath is located on first level. The kitchen is very well designed with lots of beautiful cabinets and countertops. Bright open floor plan offering nice flow for the kitchen, living

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    163 Riverwalk Terrace, Federalsburg, MD 21632

Showing Results 1 - 40, Page 1 of 4

How to Buy a Home How to Finance a Home How to Sell a Home