Caroline Homes with Bungalow Style

Caroline Homes with Bungalow Style

Welcome to Caroline County, Maryland, a hidden gem nestled in the heart of the Eastern Shore. Known for its picturesque landscapes, rich history, and vibrant community, Caroline County offers a unique blend of rural charm and modern convenience. With its lush farmland, serene waterways, and welcoming neighborhoods, it’s no wonder that many are drawn to call this beautiful area home.

One of the most delightful architectural styles you’ll find in Caroline County is the charming bungalow. These homes exude warmth and character, often featuring inviting front porches, open floor plans, and cozy nooks that encourage relaxation and connection. Bungalows are perfect for those who appreciate a blend of historic charm and functional living, making them ideal for families, retirees, or anyone seeking a peaceful retreat.

Living in a bungalow in Caroline County means embracing a lifestyle that celebrates both community and nature. Picture yourself enjoying morning coffee on your porch while listening to the gentle sounds of nature. With nearby parks, walking trails, and access to the Choptank River, outdoor enthusiasts will find plenty of opportunities for recreation and relaxation.

In addition to its natural beauty, Caroline County boasts a strong sense of community, with local events, farmers' markets, and festivals that bring residents together. Whether you're exploring local shops in Denton or enjoying a scenic drive through the countryside, you’ll find that Caroline County is a place where neighbors become friends and memories are made.

If you’re searching for a home that embodies charm and character, consider a bungalow in Caroline County—a place where your dream of serene living can come true.

Newest Caroline Homes with Bungalow Style

$699,000
3 Beds ⋅ 2 Baths
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 find multiple outbuildings and specialized structures, including: 40x80 shop with three overhead doors; 30x40 heated and cooled workshop with two overhead doors and water; 15x48 kennel building with dedicated office space; 24x24x32 barn with four stalls; Poultry and roosting sheds; Established gun range area; Small animal paddocks; Two large fenced pastures; Fenced duck pond; Additional storage sheds throughout the property The main home offers comfortable one-level living with a split-bedroom layout, featuring an open kitchen/dining/living area anchored by a cozy wood stove. With 3 bedrooms, 2 bathrooms, and approximately 1,200 sq. ft., it’s the perfect base for enjoying the land that surrounds you. Bring your animals, your imagination, and your offer — opportunities like this don’t come around often. Your private retreat with unlimited potential is waiting.

14540 Drapers Mill Rd, Goldsboro

Listing courtesy of Brenton Realty Group. Contact: 4104794663
$624,900
3 Beds ⋅ 2 Baths

23130 Sparks Road Rd, Ridgely

Listing courtesy of McClain-Williamson Realty, LLC. Contact:

$699,000
3 Beds ⋅ 2 Baths
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 find multiple outbuildings and specialized structures, including: 40x80 shop with three overhead doors; 30x40 heated and cooled workshop with two overhead doors and water; 15x48 kennel building with dedicated office space; 24x24x32 barn with four stalls; Poultry and roosting sheds; Established gun range area; Small animal paddocks; Two large fenced pastures; Fenced duck pond; Additional storage sheds throughout the property The main home offers comfortable one-level living with a split-bedroom layout, featuring an open kitchen/dining/living area anchored by a cozy wood stove. With 3 bedrooms, 2 bathrooms, and approximately 1,200 sq. ft., it’s the perfect base for enjoying the land that surrounds you. Bring your animals, your imagination, and your offer — opportunities like this don’t come around often. Your private retreat with unlimited potential is waiting.

14540 Drapers Mill Rd, Goldsboro

Listing courtesy of Brenton Realty Group. Contact: 4104794663
$330,000
3 Beds ⋅ 3 Baths
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 cooking and gathering feel effortless. The first-floor primary bedroom is your sanctuary—walk-in closet, walk-in tile shower that feels like a spa, beautiful quartz vanity. Wide plank LVP flooring keeps the whole home feeling fresh and connected. The two-car detached garage is insulated, has electric, and includes a storage room—practical space that actually works. The 0.325-acre lot sits across from Chambers Park, where you can enjoy a ball game, walking path, or tennis courts. Paved driveway, plenty of parking, and a home that's honestly ready for you. This is what move-in ready feels like: fully updated, thoughtfully finished, and zero projects waiting. Just unpack and live.

104 Chambers St, Federalsburg

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$225,000
4 Beds ⋅ 1 Baths
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.

5258 Preston Rd, Federalsburg

Listing courtesy of Marshy Hope Realty LLC. Contact: 410-754-7000
$289,000
4 Beds ⋅ 2 Baths
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 moment you arrive. Inside, you’ll find a bright and inviting living area featuring a cozy electric fireplace insert and beautiful wood‑beam accents. The freshly renovated kitchen is thoughtfully designed and opens seamlessly to the dining area. The main floor also offers two comfortable bedrooms and a full bathroom. Head upstairs and you’ll discover an open foyer leading to two more spacious bedrooms and a convenient half bath. And if you’re craving even more room, the full basement downstairs gives you endless possibilities—storage, hobbies, a workshop, you name it. When you’re ready for a break from reality, step out onto the back deck and soak in the peace and tranquility of the backyard which overlooks looks a farm! It’s the perfect spot to unwind. Plus, enjoy peace of mind with numerous updates throughout the home, including a new HVAC system, water heater, appliances, flooring, complete remodled bathrooms and more. Don't wait... this property will not last long!

115 Boyce Mill Rd, Greensboro

Listing courtesy of Brenton Realty Group. Contact: 4104794663
$110,000
2 Beds ⋅ 2 Baths
**Back Active at no fault of the seller**Opportunity awaits at 26471 Three Bridges Rd in Federalsburg, MD! This partially remodeled 2-bedroom, 2-bath home is ready for your finishing touch. Inside, the property has been taken down to the framing and subflooring, giving you a true blank canvas to bring your vision to life—whether you’re an investor looking for your next project or a buyer ready to customize every detail. Set on nearly a half-acre lot surrounded by trees, the home offers privacy and a peaceful wooded setting while still being just a short drive to town conveniences. With the major groundwork already started, this property presents the perfect chance to create a modern retreat or a profitable investment in a serene location. Bring your creativity and tools—this is a project with endless potential! Property being sold AS-IS WHERE IS

26471 Three Bridges Rd, Federalsburg

Listing courtesy of Keller Williams Realty. Contact: (302) 856-1458
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