Refine Search
Sort by
$320,000
3 Beds 2 Baths
Welcome to your own slice of peace on Paradise Ln! This charming 3-bedroom, 2-bath home has been lovingly maintained by its original owner and is ready for its next chapter. Sitting on a beautiful, level 1.01-acre lot in a quiet Caroline County neighborhood, there’s plenty of room to grow, garden, or just enjoy the view from the classic country front porch. Inside, you’ll find a cozy 1,116 sq. ft. layout with some solid updates over the years, including a newer heat pump and hot water tank. Location is a huge plus here, you’re just about a mile away from the middle and high schools, making those morning drop-offs a breeze. If you’re looking for a well-cared-for home with a bit of elbow room, this is the one!

20100 Paradise Lane, Ruther Glen

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: .

$320,000
4 Beds 3 Baths
There's one thing you almost never find at this price point in Caroline County: a full detached living space that's completely finished and ready to use on day one. This one has it. Set on a quiet stretch in Federalsburg, this four-bedroom, three-bath home has been thoroughly updated from top to bottom. Every major system has been replaced within the last ten years. Roof, HVAC, water heater, windows, electrical, plumbing. You're not buying into a project. You're buying into a home that's already done. New flooring and fresh paint run throughout. The kitchen is completely new, the bathrooms are updated, and the appliances have been replaced. The work is clean, and it shows. At 1,608 square feet above grade, the main house is comfortable and functional. The unfinished 1,072 square foot basement gives you room to grow on your own schedule. But the real story here is the detached living space. Fully finished and completely separate from the main house, it's the kind of bonus that changes how you live. Use it as a home office, a studio, an in-law suite, a rental opportunity, or a guest space. Whatever your situation calls for, this space adapts. In this market, at this price, that kind of flexibility is genuinely rare. Step outside and the backyard tells its own story. There's a deck for warm-weather mornings, a hot tub for the evenings, a fire pit for the nights worth stretching out, and a garden bed already waiting. The yard is open and fenced. Functional, private, and built for real use. Location puts you within easy reach of Easton, Denton, Salisbury, and the Delaware beaches without fighting the Bay Bridge. Federalsburg sits squarely in the heart of Maryland's Eastern Shore. Close to enough, quiet enough, and priced in a way that still makes sense. Buyers will find a move-in ready home with serious long-term value paired with the space and flexibility they've been looking for. Either way, this one is worth seeing in person. Schedule your showing today.

529 Liberty Road, Federalsburg

Listing courtesy of Real Broker, LLC - Annapolis. Contact:

Selling Office: .

$319,000
3 Beds 2 Baths
Welcome home to 14535 Dry Bridge Rd, where thoughtful renovations meet peaceful country living. This fully renovated, one-level ranch sits on a private, flat 1-acre lot with no HOA, offering space, privacy, and flexibility you don’t often find—especially at this price point. Step inside to fresh interior and exterior paint, all-new flooring throughout with durable LVP in the main living areas and plush new carpet in the bedrooms, and a bright, inviting layout designed for everyday comfort. The brand-new kitchen is a true highlight, featuring new cabinetry, quartz countertops, stainless steel appliances (2026), updated hardware, and modern lighting and plumbing fixtures. The home offers three bedrooms and one fully renovated bathroom, complete with a new vanity, toilet, and modern finishes. Major system updates include a new HVAC system (2026), new hot water heater, and a roof replaced in 2017—providing peace of mind for years to come. Just off the kitchen, a versatile bonus room offers the perfect space for a home office, playroom, mudroom, or additional sitting area and leads directly to the screened-in back porch. The porch has been refreshed with new screening, updated trim, and new gutters—an ideal spot to relax and enjoy the peaceful surroundings. Outside, the property continues to shine with a detached oversized two-car garage, an additional one-car carport, and plenty of room for hobbies, storage, or animals. The home also features a brand-new, fully permitted septic system with a new distribution box and drainfield. This is a rare opportunity to own a fully renovated, move-in-ready home on a private lot with exceptional garage space, modern upgrades, and the freedom to live how you choose—an incredible value for everything this property has to offer.

14535 Dry Bridge Road, Ruther Glen

Listing courtesy of Keller Williams Capital Properties. Contact:

Selling Office: .

$315,000
3 Beds 2 Baths
Welcome to this estate sale opportunity offering convenient one-level living in a wonderful, well-established community just minutes from Easton and St. Michaels. Lovingly owned by the original owner, this 3-bedroom, 2-bath home is ready for its next chapter. The home features a functional floor plan with spacious living areas and offers great potential for updates to match your personal style. Enjoy the screened-in rear patio overlooking a generous 1.5-acre lot—perfect for relaxing, entertaining, or outdoor activities. Additional highlights include two well-maintained outbuildings, ideal for storage, workshop space, or hobbies. Whether you are seeking a primary residence, second home, or investment opportunity, this property presents tremendous potential in a desirable Eastern Shore location. Being sold strictly AS-IS as part of an estate sale. The home will require repairs and is best suited for buyers looking to renovate and bring their vision to life. Crawl Space mold remediation has been completed by the sellers.

21611 Everlea Drive, Preston

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: .

$315,000
3 Beds 2 Baths
Tucked away in a peaceful rural setting, this beautifully updated home offers space, privacy, and modern convenience on 1.14 acres. Welcome to 8409 Harmony Road—a truly special property with access from both Harmony Road and the rear of the property via Towers Road, providing added flexibility and convenience. This move-in-ready 3-bedroom, 2-bath home blends thoughtful updates with a functional layout, all surrounded by a tranquil, tree-lined setting. Inside, a bright open floor plan showcases vaulted ceilings, fresh paint, recessed lighting, and a seamless blend of new luxury vinyl plank flooring and carpeting throughout. The spacious eat-in kitchen is enhanced with recessed lighting and a full suite of GE and LG stainless steel appliances, including a built-in microwave, refrigerator, dishwasher, and full-size washer and dryer. The primary suite is privately situated and features a walk-in closet along with an updated en suite bath complete with an accessible walk-in shower and modern fixtures. Well-proportioned secondary bedrooms offer comfortable space for guests, a home office, or everyday living. Recent improvements provide added value and peace of mind, including a newer roof on both the home and detached garage (2019), new ceiling fans, a new hot water heater, and an American Home Shield warranty covering major systems such as appliances, HVAC, septic pump, and well pump. Outdoor spaces are designed for both relaxation and functionality, featuring a rear deck with a porch swing, a picnic area surrounded by mature trees, and plenty of open space to enjoy a serene country setting. The enclosed two-car detached garage/workshop includes a newer garage door (2019), and the property offers ample parking for 6+ vehicles, along with space for boats, RVs, or trailers. With well and septic in place, no city taxes, and no HOA, this property offers flexibility for a variety of lifestyles—whether full-time living, multi-generational use, or investment potential. Conveniently located near shopping and dining while still enjoying the peace and privacy of the countryside, this is a rare opportunity to own a move-in ready home with room to grow. Mortgage savings may be available for buyers of this listing.

8409 Harmony Road, Denton

Listing courtesy of Redfin Corp. Contact:

Selling Office: .

$315,000
3 Beds 2 Baths
Welcome to this beautifully updated 3 bedroom, 2 bath home in Ruther Glen. Inside, you’ll find fresh paint, brand new LVP flooring and carpet, and updated lighting, including recessed lighting in the kitchen. The kitchen features granite countertops, new cabinets, and all new appliances. Both bathrooms include new vanities and updated finishes. Major updates include a brand-new furnace, tankless hot water heater, and HVAC improvements. Outside, enjoy a fully fenced backyard and a fresh gravel driveway. Conveniently located near everyday essentials in Thornburg and Ladysmith, with quick access to Interstate 95 and U.S. Route 1, and an easy drive to Fredericksburg and Richmond.

2409 Quail Oak Drive, Ruther Glen

Listing courtesy of Century 21 Redwood Realty. Contact:

Selling Office: .

$310,000
4 Beds 2 Baths
Welcome home to this spacious and beautifully updated 4-bedroom, 2-bath split-level nestled on a private lot backing to mature trees in the sought-after Lake Land'Or community. Freshly painted with new carpet and additional upgrades throughout, this move-in ready home offers comfortable living space for everyone. Enjoy the peace and privacy of your wooded backyard while taking advantage of the community's exceptional amenities, including a gated entrance, swimming pool, lake access, beaches, playgrounds, and more. Conveniently located between Fredericksburg and Richmond, this home provides an easy commute while offering the perfect balance of recreation and relaxation. Don't miss your opportunity to enjoy lake community living at its best!

255 Manchester Drive, Ruther Glen

Listing courtesy of RE/MAX Cornerstone Realty. Contact:

Selling Office: .

$310,000
3 Beds 2 Baths
ONE LEVEL LIVING at it's finest!! Only a few minutes to I-95 and "civilization", restaurants and shopping, this fantastic "cabinesque" property, in popular Caroline Pines, is VACANT and ready for prime-time... and checks off lots of boxes!! -- 3 Bedrooms (all with brand new quality carpet) and 2 full updated bathrooms, open floor plan with dining area, comfy living room with woodburning stove, large kitchen with island and updated cabinetry, utility room... and a terrific detached BONUS OUTBUILDING/SHED. This XXL "shed" is divided into half as storage/WORKSHOP with electric... and 1/2 as a modern finished STUDIO with mini-split HVAC system, recessed lights and very comfortable interior finishes with a window and a windowed entry door! Fully fenced and level backyard (even some grapevines!), rear deck. NEW ROOF IN 2024! The Caroline Pines subdivision is a "golf cart friendly" community with approximately 700 permanent wooded and open lots, 5 lakes for recreational use and, other amenities such as community pool, fitness center, and more!

26236 Shannon Mill Drive, Ruther Glen

Listing courtesy of Keller Williams Realty/Lee Beaver & Assoc.. Contact:

Selling Office: .

$309,900
2 Beds 2 Baths
Nestled in the serene Lake Caroline community on a rare double lot (with only one HOA fee due to merged lots with County), this charming home offers a perfect blend of comfort and modern updates. The interior features striking cathedral ceilings in both the kitchen and the living room, which is anchored by a wood-burning fireplace currently outfitted with electric logs. The functional layout includes primary bedroom with a full bath, a second spacious bedroom features a large walk-in closet and access to a second full bath with a skylight. For those needing extra space, a spiral staircase leads to a versatile loft/office that could easily be converted into an additional bedroom. Pull down attic stairs with additional storage in the attic as well. The home is designed for brightness and efficiency. Recent exterior improvements include new gutters, while the mechanical systems have been meticulously maintained with bi-annual HVAC service and a newer water heater. The outdoor living space is enhanced by a dining area that leads to a deck and a storage shed. This property is a well-cared-for sanctuary ready for its next chapter. Roof is approx 7 years of age as well as at time of roof install - both skylights along with kitchen and bath windows were replaced.

322 Musket Drive, Ruther Glen

Listing courtesy of Century 21 Redwood Realty. Contact:

Selling Office: .

$306,000
3 Beds 2 Baths
Welcome home to easy one-level living tucked away on a peaceful wooded lot with no HOA! Privately situated down a long driveway, this charming home offers the perfect blend of comfort, convenience, and space—ideal for first-time homebuyers, downsizers, or anyone looking for privacy without sacrificing location. Inside, you’ll find fresh updates throughout including brand new luxury vinyl plank flooring and fresh paint, creating a bright, clean, move-in ready feel from the moment you walk in. Major systems have already been taken care of for added peace of mind, including a brand new roof (2026), HVAC only 4 years old with regular servicing, water heater approximately 5 years old, and septic pumped in 2026. Step outside and enjoy your own private wooded retreat. The large deck offers the perfect space for grilling, entertaining, or simply enjoying your morning coffee while taking in the peaceful surroundings. Just beyond, the fire pit area creates a cozy outdoor gathering space—perfect for evenings with friends and family under the stars. The extra-large shed provides plenty of room for storage, tools, or hobbies, and with no HOA, you’ll appreciate the flexibility and freedom to truly make the property your own. Conveniently located just minutes from I-95 for an easy commute and close to the exciting new Kalahari Waterpark, shopping, dining, and everyday conveniences, this home offers a rare combination of privacy, updates, and accessibility. Move-in ready, thoughtfully maintained, and full of charm—don’t miss your opportunity to own this peaceful wooded retreat!

12490 Us Route 1 Highway, Woodford

Listing courtesy of Coldwell Banker Elite. Contact:

Selling Office: .

$305,000
2 Beds 1 Baths
BACK ON THE MARKET at NO FAULT to the seller. Classic Charm & Expansive Space in Woodford! Welcome to 13859 Farmers Dr., a delightful mid-century home that perfectly balances cozy interior living with an incredible outdoor footprint. Built in 1954, this residence offers a peaceful retreat in the Woodford region with plenty of room to grow. Inside, you'll find 1,268 sq. ft. of inviting, functional living space with 2 comfortable bedrooms, 1 full bathroom, and two separate living rooms that give everyone space to spread out. The large kitchen is made for gathering, and beautiful hardwood flooring runs throughout, adding a touch of timeless warmth and character. There's even a sunroom with real windows, not just screens, so you can enjoy the view in any season. Downstairs, the basement offers excellent versatility, perfect for a home workshop, hobby space, or extra storage. Step outside and the possibilities open right up. Situated on a 0.76-acre lot with mature landscaping, the home features a brand new deck, a charming fire pit area, and a 1-car garage. Whether you dream of a sprawling garden, a private play area, or future additions, there's room to make it happen. Best of all, you're just 10 minutes from historic Bowling Green and less than 30 minutes from Fredericksburg and the VRE. This is the kind of place that makes you want to stay awhile, catch up with friends, and sip your coffee a little slower.

13859 Farmer Drive, Woodford

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: .

$305,000
3 Beds 2 Baths
Beautiful one-level living home situated on a spacious lot in the highly sought-after Lake Land Or community. This home offers a great combination of comfort, updates, and outdoor space, making it truly move-in ready. Major updates include a newer roof (2021), wood flooring throughout the main living areas (2021), and an expansive composite deck (2021) overlooking the backyard. A patio with fire pit (2021) creates the perfect setup for relaxing or entertaining, while the large yard offers plenty of space to enjoy the outdoors. In 2026, the home was refreshed with brand-new carpet and touch-up interior paint, giving it a clean and well-maintained feel. One of the standout features of this home is the incredible Lake Land Or community. Residents enjoy access to two lakes spanning over 87 acres with water skiing, canoeing, and fishing, along with multiple boat launches, beaches, fishing piers, a campground, dog park, fitness center, pavilions, playgrounds, swimming pools, skeet shooting range, and tennis courts. The gated entrance provides an added sense of privacy and security. Conveniently located just minutes from I-95 and Route 1, and within easy driving distance to Fredericksburg and Richmond, this home offers both tranquility and accessibility. This is one you don’t want to miss.

644 Wright Drive, Ruther Glen

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: .

$305,000
3 Beds 3 Baths
Must-see end-unit townhome built just two years ago! This 3 bed, 2.5 bath still feels new and features a bright and open floorplan. It features fresh modern paint throughout, and the builder upgrades. Luxury vinyl plank flooring entirely on the main level. GE stainless steel appliances with a kitchen island makes dinner prep a breeze. It includes smart features such as a smart thermostat and an energy efficient rating which means lower utility bills. Upstairs, you’ll love the convenience of having the laundry room on the bedroom level and a walk-in closet in the owner's bedroom. This low maintenance townhome comes packed with parking with an attached two car parking pad, rear parking, and street parking in the front. Walk right out the back of the townhome and experience the common area which includes a pickleball court, community garden, tot lot, walking trails, and a beautiful view of the sunsets. Take a short walk to the community pool and pool house this summer which features a community grilling area. Just a short drive in the community takes you to the Pendleton Golf Course which offers free golf to its residents, or you can upgrade your membership for additional playing time. This townhome offers the perfect blend of style and function.

7265 Statesman Boulevard, Ruther Glen

Listing courtesy of NetRealtyNow.com, LLC. Contact:

Selling Office: .

$300,000
4 Beds 3 Baths
*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 | Newly fenced yard | Detached 2-bay garage with upper storage | 30-amp RV hookup | Ample parking for RVs, boats & trailers. THE DETAILS: There are houses. And then there are homes that make you feel something the moment you walk in the door. 209 W Sunset Avenue is the second kind. Built in 1910 and restored over the years, this 4-bedroom, 2.5-bath Victorian in Greensboro, Maryland is a true one-of-a-kind find, a property where original craftsmanship and modern practicality coexist in a way that simply doesn't happen by accident. Step inside and the staircase sets the tone immediately. Original hardwood floors run throughout. Stained glass catches the light. Period lighting and intricate woodwork tell the story of an era when homes were built to last a lifetime. Many of those wood details, the doors, the trim, the island in the updated kitchen, are believed to be pre-blight American Chestnut, a wood so rare today it's essentially irreplaceable. You cannot buy this. You can only find it. And unlike so many Victorian-era homes that charm you on the surface but frustrate you in daily life, this one has been thoughtfully upgraded where it counts. The primary suite is a true primary — private bath, double closet, real privacy. That's not a given in a home from 1910. Bedroom-level laundry means no hauling baskets up and down stairs. The kitchen has been updated with a chestnut island that ties the old and new together beautifully. Two finished rooms in the full walk-up attic give you the flexibility that most homes at any price point simply don't offer — a guest suite, a home office, an art studio, a gaming room, a yoga space. You decide. The major-ticket items are already handled: the electrical system has been updated, the main-level windows and the roof are newer, and the home includes owned solar panels. In Maryland — where electric bills can be genuinely painful — those panels are a financial advantage that pays you back month after month. A pellet stove conveys with the home for extra comfort in the colder months. Step outside and the property continues to impress. The wraparound porch is the kind you picture when you imagine slowing down. The screened rear porch overlooks a newly fenced backyard — private, quiet, yours. The detached 2-bay garage features a metal roof, floored upper-level storage, and an upper loading door that makes moving large items a breeze. A 30-amp RV hookup is already in place, and there is room — real room — for RVs, boats, trailers, and multiple vehicles. This is a home with history, heart, and the infrastructure to live comfortably in it for decades. Homes like this come along once, if you're lucky. Come see it before someone else does. (Garage being sold as-is.)

209 W Sunset Avenue, Greensboro

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: .

$300,000
2 Beds 1 Baths
(UPDATED PHOTOS COMING SOON) Gorgeous newer home in the sought after amenity filled gated community.. Lake Land'Or Subdivision, is coming to the market soon! There is so much to say about this adorable home including the large country front porch, tall windows thru-ought, a shed for storage stays and a deck off the back leading to a spacious yard ready for you to make it your own. Inside you immediately feel the warmth and love, makes you want to grab your book and cozy up to the large windows and stay inside as long as possible. The kitchen boasts a granite peninsula/island, LVP flooring, tons of storage with many cabinets to the ceiling, pantry, and a stainless steel full appliance package. The laundry/storage room is perfect for that extra storage that everyone needs. Make your way to the 2 large bedrooms, walk in closets, linen closet, and the perfectly appointed bathroom. The bathroom includes LVP flooring, double vanity sink, and a 5' tile walk in shower!! All of this located in the prime location within 6 minutes of I-95, grocery, shopping and dinning. Lake Land'Or is known for the gorgeous lake, beachy areas, pools, club house many playgrounds, archery, tennis, volleyball, basketball, dog parks, walking paths and so much more. The staff does an amazing job keeping up with the many amentiy and common areas, plus the added benefit of having a gated community and 24 hour security....this all could be yours, we are coming to the market soon!!

902 Jones Drive, Ruther Glen

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

$300,000
3 Beds 3 Baths
Great townhome with detached garage in Ladysmith Village - an amenity-filled community with its own library, sidewalks, pet areas, tot lots, community pool, fitness center, and so much more! This lovely home welcomes you with a large covered front porch perfect for relaxing. As you step inside, you'll notice the neutral colors, bamboo wood flooring and open flow from the dining area through the kitchen into the large light-filled family room. The kitchen highlights include 42-inch cabinets and pull-out shelves in all of the lower cabinets, stainless appliances (new stove and microwave), large refrigerator and pantry. There is also a half bath and laundry closet on the main level. From the family room, step out into your fenced yard and access the detached garage with an additional parking space adjacent to the garage. Back inside, the upper level has a wonderful primary bedroom with cathedral ceiling, huge walk-in closet and LVP flooring, as well an en-suite full bath with beautiful ceramic tile. Two additional bedrooms and full bath with ceramic tile complete the upper level. This home has been well maintained and offers affordability without sacrificing quality - the HVAC is serviced twice per year, and the hot water tank, washer, oven/range, and microwave have all been replaced within the last 2 years, as well as the smoke detectors. Don't miss out!

7124 Azalea, Ruther Glen

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: .

$300,000
3 Beds 2 Baths
Welcome home! You've got to come see this well maintained 3-bedroom, 2-bath home offering comfort, character, and charm. Sitting on just over one acre, this property blends peaceful living with everyday convenience, located only a short drive from grocery stores, restaurants, and is roughly 30 minutes from both Dover and Milford. Step inside to find hardwood floors that add warmth and charm to the main living areas. The main floor offers a nice sized living room, a full bath, 2 bedrooms, a mud room/ enclosed porch that provides the perfect spot to relax with morning coffee or unwind at the end of the day. A dry basement offers excellent storage space. Upstairs is a private primary suite featuring a renovated full bath and an additional flexible space that can easily serve as a nursery, office, game room, craft room, oversized closet, or whatever suits your lifestyle. Outside, the property continues to impress with a 2-car detached garage and an additional outbuilding that's ideal for hobbies, storage, or workshop use. With plenty of room to spread out, garden, entertain, or simply enjoy the outdoors, this property offers the best of suburban living without sacrificing convenience and is a wonderful opportunity for anyone seeking space, comfort, and versatility. New HVAC and primary bath in 2025. Tell your agent that this is the one and have them schedule your showing today!

12739 Greensboro Road, Greensboro

Listing courtesy of Iron Valley Real Estate Ocean City. Contact:

Selling Office: .