Caroline County MD Homes For Sale

Opportunity awaits on this peaceful 1.46± acre wooded parcel in Preston. Tucked among mature trees, this property offers a private country setting with endless potential ...

This valuable commercial property consists of 10.4 level acres that fronts two roads. It is located on the corner of Blades Farm Rd and Sharp Rd. Blades Farm Rd runs par...

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 f...

Photos Coming Soon. You'll love this custom home nestled on 2.13 private acres, offering nearly 2,500 square feet of thoughtfully designed living space with 4 bedrooms a...

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 withi...

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 oppo...

Investors! Subject to current month-to-month leases this duplex is located in the heart of Preston and close proximity to the school.

Eastern Shore living at its finest! Nestled in the desirable Tuckahoe Springs subdivision, this beautifully maintained home offers the perfect blend of comfort, style, an...

Welcome to your own private retreat! Situated on 4 peaceful acres, this well-maintained 4-bedroom, 2.5-bath home offers the perfect combination of comfort, privacy, and f...

Welcome to 11139 Central Avenue, where the tranquility of country living meets the convenience of a prime Caroline County location. Nestled on one acre outside Ridgely, t...

OFFER DEADLINE- please submit all highest and best offers by 5:30 pm on 8/4. Welcome to this stunning Victorian gem built in 1900, gracefully resting on three combined lo...

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 ...

Discover a hidden gem in this charming 2-bedroom, 1-bathroom ranch-style home, built in 1950 and brimming with potential. Nestled on a generous 0.48-acre lot, this proper...

Beautifully designed new construction interior townhome located in an established community in the heart of Denton, Maryland! Offering 4 spacious bedrooms, 2.5 baths, and...

OPEN House this Saturday Aug. 1, 3:30-5:30pm! Welcome home to your own private country paradise. Nestled on 2.43 peaceful acres, this beautifully renovated log cabin blen...

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.

TBB....This beautifully designed rancher offers 3 bedrooms and 2 full baths with an open-concept floor plan and cathedral ceilings in the main living area. . Enclosed Sun...

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...

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 mo...

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 l...

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-construc...

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-cl...

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 bat...

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 Idlewi...

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 whi...

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!...

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...

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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 f...

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...

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 D...

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 fi...

WHAT A DEAL!!!! New construction. Welcome to 210 W. 2nd Street in Ridgely, where modern construction meets small-town charm. Built in 2026 with a Builder 10 year struct...

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 c...

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...

**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 Ho...

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...

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

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. Fe...

Ranch style home situated on a 1.18 acre lot. There is no access to the interior of the home. Priced below assessed value, home to be transferred occupied, as-is. Please ...

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...

Beautifully positioned along the deep protected waters of the Tuckahoe, this exceptional residence has been transformed through an extensive renovation that blends timele...

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, ...

***Price Improvement *** This delightful 3-bedroom bungalow offers a perfect blend of comfort and community. Built in 1940, this home exudes character with its sturdy blo...

3 Parcels in the Town of Greensboro!! One of which has a hooked up Water/Sewer account, so instant savings on no tap fee!! Parcels are believed to total approximately 0...

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, t...

Approximately 27.16 acres of development land located within the Town of Denton. The property is currently zoned UR (Urban Residential). Public water and sewer are availa...

Step back in time while enjoying the comforts of modern living in this beautifully maintained 1900s historic home nestled in the heart of Denton. Rich with character and ...

Welcome home to this beautifully updated 3-bedroom, 2-bath ranch offering over 2,000 square feet of comfortable living space. Thoughtfully improved throughout, this home ...

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...

Price to purchase has been lowered to help you afford top quality at a fantastic price. Come see this beautiful home. Pride of ownership is shown from top to bottom in ...

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...

Nestled at the end of a quiet street in the quaint town of Ridgely, you will find this beautifully maintained Rancher. The current owner has completed about everything i...

Exceptional opportunity to own a well-established 2,400-square-foot retail business featuring three revenue streams under one roof: a fully operational deli, liquor store...

This is 222 S. 2nd Street, a recently renovated home with historic charm. Original wood flooring, and architectural details such as moldings and antique door knobs highl...

Lovely two bedroom one bath rancher with spacious living room and dining room plus kitchen **1 car garage plus 30 x 30 storage area ** Heating is oil furnace 3 years old...

Opportunity awaits in Federalsburg! This residential lot offers the convenience of public water and sewer connections, making it a great option for your next build or inv...

Opportunity awaits in Federalsburg! This residential lot offers the convenience of public water and sewer connections, making it a great option for your next build or inv...

If you’ve been searching for a private, wooded homesite without feeling too far removed from everyday conveniences, this is it. Offering over 2.5 acres, this property pro...

Ready for Development! 43 lots within the Town limits of Federalsburg, Maryland. Total lot space as currently platted is 478,596 sq ft or 11 acres, according to public re...

Introducing an exceptional opportunity for retail and street retail investors in the bustling Ridgely area. Boasting approximately 3,321 SF, this prime property is perfec...

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 a...

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...

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...larg...

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 ...

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 su...

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 wil...

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.

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

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 charmin...

Don’t miss this exceptional 20+/- acre working horse farm thoughtfully designed for both functionality and country living. This well-equipped equestrian property offers e...

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-design...

**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 pur...

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 ...

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 outbuil...

SELLER WILL CONSIDER CONTRIBUTING TOWARD THE BUYER’S ALLOWABLE CLOSING COSTS WITH AN ACCEPTABLE OFFER! Welcome to 25485 Hignutt Road—a completely renovated 3-bedroom, 2....

This charming 2-story colonial home in Denton offers a perfect blend of classic character and modern updates. Featuring 3 bedrooms and 1½ bathrooms, this well-maintained ...

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, t...

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 o...

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 o...

14.71± acre perc-approved parcel on Trunk Line Rd in Henderson, MD! This beautiful wooded lot offers a conventional perc approved for 4+ bedrooms and provides an excellen...

Full Re-Hab 2023! Home shows well. The best of Downtown Living! This refurbished Farmhouse, has all the feels of intown country living with all the new modern ammenties! ...

Charming 3-bedroom, 2-bath rancher located in Ridgely! Inside, you’ll find comfortable one-level living with a functional open layout connecting the living room and kitch...

116,800+/- sq. ft. Industrial Complex on 7.93+/- acres in Federalsburg, MD This is a prime opportunity to acquire a three-building complex zoned ID-2, offering a mix of ...

Come discover 121 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 cott...

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...

Move-in ready and thoughtfully updated—this is one you won’t want to miss. Step inside this newly renovated 2,200 sq. ft. townhome located in the heart of Denton, MD. Fe...

Central Commercial Zoning in the town of Greensboro. 880 sq/ft block building with a brick front. Parcel is 6480 sq/ft. Central air with oil fired heat. Front yard could...

This inviting Victorian offers 4 bedrooms and 1.5 baths, that’s perfect for unwinding at the end of the day. Inside, natural light fills the main level, highlighting war...

**Don't Miss This Rare Opportunity** Pride of ownership shines throughout this beautifully appointed home, featuring 3 bedrooms, a bonus room, 3 full bathrooms, a dedicat...

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...

Located in the heart of Preston, this classic 1900-built home offers a solid opportunity for both homeowners and investors alike. Inside, the home features 3 bedrooms a...

Investor Alert! 100% occupied duplex with a 1 bedroom, 1 bath downstairs and a 1 bedroom 1 bath upstairs. Situated in the heart of Preston and close proximity to the sc...

This very comfortable rancher has ramps at rear of home for accessibility for those not able to walk up steps very well. Roomy kitchen and open floor plan allows large...

Excellent investment opportunity. 4-unit residential apartments fully rented with long-term tenants. Additional office space available. 5 units total. Current income ...

The Melville Rd Farm is located on the east side of Melville Road and is bordered to the north by Trunk Line Road. The property includes approximately 51± acres of tillab...

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 feat...

Charming Colonial-style farmhouse set on 9 scenic acres, offering a rare blend of historic character, pastoral beauty, and endless potential. Ideal for animal lovers or t...

Excellent investment opportunity. Also perfect for a homeowner, live in one unit and let the other units pay your mortgage. 4-unit residential apartments fully rented w...

Brand‑new construction in a peaceful country setting! Enjoy effortless one‑level living in this bright, open‑concept rancher designed for comfort and convenience. The spa...

Welcome to 1709 Cattail Commons Way, located in the highly desirable Savannah Overlook community in Denton, MD. This beautifully maintained 4-bedroom, 2.5-bath home offer...

Tenant-occupied property offering an excellent investment opportunity with immediate rental income. Current lease in place through July 31st. Tenants have expressed inter...

Discover the perfect blend of tranquility and convenience with this perc-approved 1.88-acre homesite, ready for your dream build. Overlooking a scenic tributary of the Up...

Move-In Ready & Beautifully Remodeled! This charming 3-bedroom, 1.5-bath home offers the perfect blend of comfort and convenience. Enjoy a spacious living room, separate ...

Welcome to this charming, Cape-Cod with a Full Unfinished basement—perfectly nestled on a spacious 1/2 Acre! This property gives you that “welcome home” feeling the mome...

Welcome to this meticulously crafted 2023 contemporary farmhouse, perfectly positioned on a spacious .85-acre lot in the established community of Ashworth. Offering 3,168...

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...

Hurry before it’s gone! This is an opportunity to buy in the sold out community of Riverwalk Terrace. The owner stayed at the home a few times some of the appliances neve...

2 Acre cleared lot. Great opportunity for a fixer upper. Home needs a fair amount of work but it has a great layout. Main level primary, office/den separate dining room...

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 ...

Turn-key and ready for your business! This beautifully renovated commercial building offers the perfect blend of professional office space and future growth potential. Po...