Caroline County MD Homes For Sale

Welcome to The Janet Baker House, a one-of-a-kind residence nestled in the heart of Denton’s Artway Cultural District, where creativity, character, and modern comfort com...

TWO HOMES, NEARLY 2.5 ACRES, AND AN IMPRESSIVE 30’ X 60’ DETACHED GARAGE! A truly unique opportunity awaits at 14971 Cherry Lane in Ridgely! Situated on 2.42 acres, this ...

Opportunity Awaits! Situated on over an acre of land on a desirable corner lot, this 3-bedroom, 2-bath home offers space, possibilities, and plenty of potential! The prop...

ONLINE AUCTION: Bidding begins 11/12/2026 @ 10:00 AM. Bidding ends 11/16/2026 @ 11:00 AM. List Price is Suggested Opening Bid. Deposit: $15,000. This auction takes place ...

YOUR OWN PRIVATE RETREAT ON NEARLY 7 ACRES — WHERE COUNTRY CHARM MEETS COMFORT, SPACE, AND ENDLESS POSSIBILITIES! Welcome to 3881 Laurel Grove Road, an inviting Colonial...

Nestled in the serene community of Quail Run, this exquisite Colonial-style residence offers a harmonious blend of comfort and elegance. Spanning 2,664 square feet, this ...

Brand New single wide **TO BE PLACED** on leased ground in Meadow Brook Mobile Park. **Home has been ordered and expected delivery is 4-6 weeks.** Features 2BR, 2BA, gas ...

Brand New doublewide on leased ground in Meadow Brook Mobile Park. Features 3BR, 2BA, gas heat, central air, and an 8x10 shed. Trash is $27.00/month. Monthly metered wate...

Discover this stunning contemporary four bedroom, 2.5 bath home located in a fantastic amenity rich and beautifully maintained community, Mallard Landing . As you step in...

***This property is eligible under the Freddie Mac First Look Initiative through 11/25/2026.*** This home on more than a half acre, backing to woods, is located on a peac...

Don't miss out on this incredible opportunity to own a zoned C1 property in the heart of Ridgely. This completely renovated 3 bed 2 bath rancher has an attached 1 bed 1 b...

Welcome to this charming 3BR/1BA home on a quiet dead end street. Recent upgrades with fresh paint throughout and remodeled bathroom with beautiful hardwood floors.

Nestled on a serene 1.51-acre lot, this exquisite Cape Cod-style residence offers a harmonious blend of comfort and luxury, perfect for those seeking an exclusive lifesty...

Nestled in a partially wooded and private setting, this delightful Cape Cod-style home offers a perfect blend of comfort and community. With 1,704 square feet of living s...

Welcome to 215 Academy in Federalsburg! This beautifully renovated three-bedroom, two-full-bath home has undergone an impressive transformation, combining modern finishes...

Discover the charm of this double-wide home nestled in the serene Harmony countryside, where rural living meets comfort in a picturesque rural setting. Spacious 1,344 squ...

Turn Key Restaurant Opportunity in the rapidly growing town of Preston MD!! Don't miss your opportunity to be a part of Main street Preston dining. With established clien...

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Enjoy the space and character of this 4 Bedroom, 3.5 Bath log home, built in 1999 and set on 11.13 acres. The property also features a detached barn/garage/workshop with...

This charming ranch-style home, conveniently located outside of Denton, offers a perfect blend of comfort and functionality. Set on a partially wooded 1-acre lot, the pro...

Welcome to 103 Parkland Road, the beautifully appointed Sullivan model home in Kinnamon Meadows, Greensboro, MD, where thoughtful design meets effortless one-level living...

Nestled in a serene setting, this charming ranch style home offers a perfect blend of comfort and convenience. Built in 2001, this well maintained residence boasts 1,554 ...

Discover the charm of this Colonial-style home at 207 Maple Avenue in Federalsburg, Maryland. Featuring 3 bedrooms, 1.5 bathrooms, and a spacious town lot, this property ...

Nestled in the charming TOWN OF GREENSBORO, this beautifully renovated residence offers a perfect blend of classic elegance and modern luxury. Originally built in 1910, t...

Completely Renovated from Top to Bottom and No HOA or Community Restrictions! Enjoy the best of country living in this beautiful 3 bedroom, 2 bath rancher, tucked away o...

Coming Soon! More Photos Coming Soon! Take advantage of this wonderful opportunity to own a spacious, beautifully updated home in Tidewater Farms! The sellers are downsiz...

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Beautiful new construction in a charming, up-and-coming community! This 3-bedroom, 2-bath home features an open-concept layout with luxury vinyl plank flooring throughout...

Welcome to 11502 Greensboro Rd, a spacious fully renovated ranch-style home offering 3 bedrooms, 2 full baths and a generous 0.68-acre lot in Greensboro. The main level f...

Don't miss out on this incredible opportunity to own a zoned C1 property in the heart of Ridgely. This completely renovated 3 bed 2 bath rancher has an attached 1 bed 1 b...

Enjoy the charm of country living in this well-maintained and nicely renovated 3 bedroom rancher! Offering over 1,300 square feet of comfortable living space with a spaci...

Enjoying a quiet cul-de-sac setting and a private wooded backdrop, this spacious 4-bedroom, 2.5-bath home offers approximately 3,117 square feet of comfortable, well-plan...

Welcome to Caroline Farms. This 3 bedroom, 2 full bath, 1 half bath contemporary/Colonial-style home features a 1-car attached garage, asphalt driveway, open front porch...

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Rare Opportunity. Mixed use! In-Town Lot. Public Water & Sewer Available! Zoned TR with IRD Overlay. 4.52 Acres! Check with Town for any questions on zoning! Conv...

INVESTOR ALERT! Duplex in Denton. Comprised of one 3 Bedroom, 1 bath unit and one 3 bedroom, 2 bath unit. Separately metered and all electric. Laundry in both units. Uni...

Coming soon to 105 Parkland Road, one of the final opportunities in Greensboro’s sought-after Kinnamon Meadows community. The Helena is an inviting 1,460-square-foot cott...

Investment opportunity! This two-unit duplex offers a functional layout with two separate residences, each featuring 2 bedrooms, 1 full bathroom, a kitchen, and in-unit l...

Welcome to 402 Maryland Avenue, a renovated two-bedroom, one-bath rancher on a generous one-third-acre corner lot in Ridgely. With approximately 1,351 square feet of livi...

Freshly renovated and move-in ready home on an acre! This 3-bedroom, 2-bath home offers a refreshed interior in a convenient Preston location. The renovation work is alre...

Be sure to schedule a tour of this beautiful home in the heart of Denton, small town living at it's best! Built in 1916 and lovingly updated and maintained throughout th...

Welcome to 3325 Sharon Court, a well-maintained home offering comfortable living spaces, thoughtful updates, and an inviting outdoor setup in Federalsburg, Maryland. The ...

Welcome to Tuckahoe Springs, a peaceful waterfront-oriented community nestled along the scenic Tuckahoe River. This well-maintained 3-bedroom, 2-bath home offers over 1,8...

Looking for one-level living, a first-floor primary suite, acreage, and a truly move-in ready home? Welcome to 24020 Carolyn Drive, where nearly every inch of this 3-bedr...

Nestled on a charming corner lot, this delightful ranch-style home offers a perfect blend of comfort and community. Built in 1955, this residence boasts a spacious layout...

Welcome to S Quail Ct in Greensboro! The model home is located across the street and can be toured 13926 S Quail Ct. This to-be-built home offers just over 1,800 square f...

Welcome to this charming 3BR/2BA classic Craftsman. Pull into the driveway and make your way to the covered front porch and the door to your forever home. Step inside to ...

Why rent when you can own and start building equity and an asset of your own? Priced at just $250,000, this charming home in the heart of downtown Denton offers an afford...

🏡 BRAND-NEW CONSTRUCTION | MOVE-IN READY | MODERN COMFORT! Your next chapter starts at 155 Wright St, Preston, MD 21655! This beautifully completed 3-bedroom, 2-bath hom...

SELLERS OFFERING 7K IN CLOSING HELP OR TOWARDS RATE BUY DOWN W/ ACCEPTABLE OFFER. Step into a charming piece of history with this beautiful Colonial home in the desirabl...

SELLER INCENTIVE! Sellers are offering up to $6,300 toward a rate buydown with an acceptable offer, giving a qualified buyer the opportunity to enjoy a lower interest rat...

Back on the market and updated photos to come! Sellers are offering up to $6,300 toward a rate buydown with an acceptable offer, giving a qualified buyer the opportunity ...

Rural wooded 7 acre lot, possible home site or hunting get away, Owner will have property perked at owners expense with acceptable contingent contract. From Greensboro no...

Welcome to 107 Sunset Blvd in Preston, MD! This spacious 3-bedroom, 2.5-bath brick home offers comfortable living, thoughtful updates, and everyday convenience. The invit...

Welcome to 117 Sunset, a spacious one-level ranch offering 1,890 square feet, three bedrooms, two and a half baths, and plenty of character inside and out. The standout l...

Welcome to 320 N Main St in the charming town of Greensboro! Step inside and discover a home that immediately invites you to kick off your shoes and stay awhile. Situated...

These parcels are being sold to settle an estate. Three contiguous parcels totaling 18.5+/- acres. Parcel 2 received a preliminary perc approval April 2015.

Spacious, versatile, and made for both everyday living and entertaining, this 4-bedroom, 4.5-bath home offers an incredible amount of space inside and out. The heart of t...

A truly unique property offering multiple dwellings, abundant storage, and exceptional flexibility! The property features multiple residential structures, providing a var...

Historic Home + Separate Buildable Parcel with Investment Potential! Step back in time while enjoying the flexibility and possibilities this unique Main Street property ...

Set on 8.22 acres in Caroline County, this custom-built home offers distinctive features, versatile living spaces, and a natural setting backing to Maryland state land. B...

Peaceful 5.62 acre wooded lot located on the outskirts of Greensboro. Perc approved for a conventional tile septic system for up to a 4-bedroom home. Discover the perfect...

Almost new and absolutely gorgeous! Built in 2023, this beautiful 4-bedroom, 2.5-bath home offers a fabulous floor plan designed for comfortable everyday living and easy ...

SELLER INCENTIVE! Seller is offering a $5,000 credit toward buyer closing costs or an interest rate buydown! Take advantage of this opportunity to reduce your upfront exp...

REDUCED $15,000! Nestled in the charming Town of Denton, this Adorable Cottage exudes warmth and character! Lots of Upgrades and Updates are all sure to please! This be...

Welcome to 4 N Maryland Ave in Ridgely! This spacious 4-bedroom, 2.5-bath home offers 2,552 square feet of living space on approximately 0.21 acres. The home features a t...

105 Noble Ave is proof that you don't have to sacrifice space to stay within budget! This massive home offers 3 bedrooms, 2 full bathrooms, and an incredibly flexible flo...

Secluded 4 Acre lot bordering the Idylwild Nature Preserve offering excellent hunting, biking, hiking and fishing. According to the county there is a well on site. Zoned ...

RENOVATED RANCH ON 0.73 ACRE WITH IN-GROUND POOL & 3 GARAGES! Seller is offering $5000 towards settlement help! Welcome to this charming ranch-style home, where classic ...

Affordable 2-Bedroom Home in the Heart of Ridgely. Welcome to 305 Caroline Avenue, a charming and budget-friendly two bedroom, one bath that's conveniently located. It's ...

Tucked away on a private lot, this spacious property offers a combination of privacy and convenience. The main level features LVP flooring, a large updated kitchen with c...

The home is located in between Easton and Preston, very close to Easton major shopping centers. This home offers 3 bedroom 2 full baths, and a large living room, Very pri...

This great home is tucked in a cozy cul de sac just out side of town and boasts an open floor plan on the first floor. The kitchen is open and spacious with plenty of ca...

$378,500! Looking for a little more house, a little more land and a lot more room to enjoy life? Welcome to 5716 Bethlehem Road, where Mid-Shore living comes with 4 bedro...

This spacious two-story home offers three bedrooms, two-and-a-half bathrooms, and plenty of room to spread out. The main level features a generously sized living room and...

BACK TO ACTIVE DUE TO NO FAILT IF THE SELLERS. This purchase includes two lots totaling 3.73 acres on the corner of Miles branch Rd and Meadowbrook Rd. Lot #1 is buildabl...

*Major Price Improvement* **Thoughtfully Renovated & Move-In Ready** Welcome to a beautifully renovated home offering 3 bedrooms plus a flexible bonus space with potenti...

5 BEDROOMS — 2,250 SQ FT — MOVE-IN READY — 2-CAR GARAGE — ESTABLISHED LISTER ESTATES Looking for the space of a larger home without the wait, construction process, or unc...

Welcome to this spacious ranch-style home situated on approximately 1.98 private, wooded acres, offering an exceptional combination of space, privacy, and versatility. W...

Offered for the first time, this custom-built home is nestled on 2 private acres in the highly sought-after water access community of Forest Landing, conveniently located...

Welcome to 11509 Reed Cir, a charming 3-bedroom, 2-bathroom rancher nestled on 1.10 acres in Ridgely, Maryland. Set against a peaceful, tree-lined backdrop, this home off...

New Price, Move In Ready & Closing Cost Help! Welcome home to this beautifully designed new construction interior townhome, ideally situated in an established community i...

Welcome to 1210 Market Street. Located just minutes from shopping and downtown. This charming bungalow is charming and has been well maintained. Adjoining bedrooms or ...

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....

Across from the boat ramp and water view of 3 ponds on the property! Outdoor enthusiasts, nature lovers, and adventure seekers — welcome to your dream retreat. This one‑o...

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 sc...

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 ...

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...

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 o...

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 o...

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 upd...

You'll love this custom home nestled on 2.13 private acres, offering over 2,854 square feet of thoughtfully designed living space with 4 bedrooms and 2.5 baths. The open ...

PRICE REDUCTION PRIVATE 1-ACRE WOODED LOT – PERC APPROVED– DEEDED ACCESS! Looking for a peaceful, secluded setting to build your dream home? Discover this mostly wooded...

Exceptional owner-user or investment opportunity in the heart of Federalsburg's primary retail corridor. This ±6,375 SF Class A end-cap commercial unit is located within ...

Remarkable Move in Ready Townhome! Beautifully designed new construction interior townhome located in an established community in the heart of Denton, Maryland! Offerin...

This charming cape cod home is waiting for your creative touches! Lots of room on three floors. The main floor boasts a large living room with new vinyl flooring. A se...

Vacant lot, check with the county about putting a new house on this lot. There was previously a house on this lot.

Seller is offering a $4,500 credit for new carpet in all 3 bedrooms! Welcome home to this charming 3-bedroom, 2-bath rancher offering the perfect blend of comfort and con...

Unimproved bulding lot . Did you know that there is a Brooklyn in Federalsburg.

Privacy, space, and endless possibilities — this 5.06-acre retreat offers the lifestyle you've been looking for. Tucked into a partially wooded setting at the end of a qu...

HUGE PRICE REDUCTION. READY FOR A QUICK SALE. Excellent investment opportunity! Over 1/4 acre lot. Home needs TLC. Partial owner financing available. Call for more i...

This exceptional commercial property, constructed in 2007, presents a prime investment opportunity with significant potential for returns. The 8,000 square foot building ...

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 t...

Excellent office opportunity! The former Choptank Community Health facility is a modern medical office building that can be easily repurposed for any business use. Just s...

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 re...

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. Offerin...

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...

Ready to own without the stress? This fully renovated home is one your friends will be drooling over. Move in and start your life, not your renovation. The kitchen stea...

Enjoy 129 ± acres of recreational land in Caroline County, Maryland. The property includes approximately 80 ± acres of timberland protected by easement (see attached Rest...

This is the one! Approx. 16.77 acres with an owner built 3 bedroom home. One acre with home plus additional acreage. Some acreage is wooded with wild life including, but ...

Charming updated Farmhouse style home with hardwood floors throughout and tiled bathrooms. The open kitchen features quartz countertops, a center island for extra prep sp...

An exceptional offering, beautifully situated along the deep, protected waters of Tuckahoe Creek. This beautifully appointed waterfront residence has undergone an extensi...

Updated + Upgraded - Turn-key 4BR/2.5BA contemporary 2-story home on a culdesac lot backing to trees, near historic downtown Denton - a true gem of an Eastern Shore town,...

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, ...

With LAND becoming less and less available, here is your opportunity to own 3 PARCELS in the Town of Greensboro!! At least one of which has a hooked up Water/Sewer accou...

NEW PRICE FOR A NEW SEASON! Now offered with a $20,000 price improvement, 312 Market Street combines approximately 2,300 square feet of living space with significant upda...

Nestled in a quiet setting, 3894 Old Denton Rd is a charming rancher that offers the ease of true single-level living. The home features an inviting, open layout where a ...

This 178,000-square-foot industrial facility sits on 15.40 acres within an Opportunity Zone. The building features clear heights of 31 feet at the center and 24 feet at t...

Absolutely beautiful rancher, priced below appraised value! Why wait for new construction? Completed in 2025, this custom-built, move-in ready rancher offers 1,436 squa...

Beautiful to be built new construction on 1.8 acres just outside Denton. This home offers 4 bedrooms, 2 full baths, great open kitchen with island, pantry, separate laun...