Chesapeake Estates Real Estate

Chesapeake Estates Real Estate

Welcome to Chesapeake Estates, a hidden gem nestled in the heart of the United States, where charm meets modern living. This picturesque subdivision offers a serene escape from the hustle and bustle of city life while still providing easy access to urban amenities.

Chesapeake Estates is characterized by its beautifully designed homes, each exuding unique architectural styles that blend seamlessly with the natural landscape. Lush green spaces and meticulously maintained gardens create an inviting atmosphere, making it a perfect place for families, retirees, or anyone looking for a peaceful community to call home.

Residents of Chesapeake Estates enjoy a wealth of amenities right at their fingertips. The community features walking trails that meander through scenic parks, perfect for morning jogs or leisurely strolls with family and friends. Children can play safely in well-equipped playgrounds, while adults can gather for community events that foster neighborly connections and friendships.

The location is another highlight, as Chesapeake Estates is conveniently situated near top-rated schools, shopping centers, and dining options. Whether you crave a cozy café or a vibrant restaurant, you’ll find it just a short drive away. For those who love outdoor activities, nearby lakes and parks offer opportunities for fishing, hiking, and picnicking.

Living in Chesapeake Estates means embracing a lifestyle of comfort, community, and convenience. With its charming homes and friendly neighbors, this subdivision is not just a place to live; it’s a place to thrive. Come discover your dream home in Chesapeake Estates, where every day feels like a retreat.

Newest Listings in Chesapeake Estates

$115,000
3 Beds ⋅ 2 Baths
Welcome to your new three bedroom 2 bath home located in Chesapeake Estates. This well maintained with recent added roofs and an additional parking space that makes three paved parking spots. The property presents very well just inside the park on the left as a large lot beautifully maintained and landscaped. Affordable year round living conveniently located near marinas, restaurants, and historic downtown Chesapeake City within minutes to public boat launching, dining & shops. Prospective Buyer must complete an application and approved by Chesapeake Estates.

14 Buddy Blvd, Chesapeake City

Listing courtesy of Real-Trust-Associates, LLC.. Contact: (443) 553-2206
$615,000
4 Beds ⋅ 3 Baths
This is the home for you, if you are ready to experience the Eastern Shore Lifestyle and love coastal vibes!! Welcome to 132 Chesapeake Estates Drive, nestled in the quaint community of Chesapeake Estates. Before pulling into the driveway, you will see a peek-a-boo glimpse of the Chesapeake Bay. If you want to watch the sunset or just enjoy a meal by the water, venture to the waterfront park that is exclusive to the neighborhood. It features a playground and plenty of picnic tables for your enjoyment and convenience. Once you have let your worries melt away by the water, it will be time to head back to your home, to relax and enjoy your brand new construction home! This 4 bedroom, 3 full bath home, has upgrades in every room. It is not your average spec home. One of the highlights of the home, is the open floor plan. The living area, kitchen and dining area are completely open. The living area has a gorgeous, almost 11ft step/trey ceiling with recess lighting throughout, along with crown molding. The kitchen has a classy coastal look, with both white cabinets and a light brown island with room for barstools. The kitchen includes, soft closing cabinets, a farmhouse sink, crown molding, SS Appliances that are Energy Efficient and a subtle, elegant backsplash. If you need extra storage, for food, etc., there is extra space in the pantry, that is conveniently located in the laundry room area, directly off of the garage. Which makes for super easy access after grocery shopping. This lovely home has LVP flooring throughout, making it have a beautiful, seamless flow when touring. Crown molding is included throughout the foyer, dining area, living area, kitchen and hallways. The primary bedroom, includes an ensuite bathroom. The bathroom has a double vanity, a tiled walk in shower with upgraded fixture and a freestanding bathtub. So many other upgrades, that may seem small, but make a huge difference either aesthetically or functionally, some of those include, shiplap tastefully placed throughout the home, cedar shake impressions on the exterior, no wiring shelving in any of the 4 bedroom closets, 2 primary closets, upgraded toilets (to a higher height), etc. The exterior of the home has a nice size front and backyard, landscaping and ample driveway for parking. The attached garage is finished (meaning it has been drywalled and is painted), and includes an electric car charger, remote, keyless entry and a 360 degree camera inside the garage door opener. Which is so convenient when you have a delivery and you will not be home, but want it left in the garage. Of course, the home has a fully conditioned crawlspace (including a sump pump). Lastly, one of my favorite things about this home, is the location! At the beginning of the neighborhood, is access to the South Island Trail (a 7-miled paved trail), that you can enjoy at your convenience, whether you are a walker, runner, biker, etc. You can also be at a beach, park, marina or pier within minutes. (Including the Romancoke Pier and Matapeake Beach). If golf is more your style, you are in luck because again minutes away is the Blue Heron golf course. Don't forget all the amazing restaurants, coffee shops, and other local small businesses that are what make KI special! Call today to schedule your private showing! MHBR: 7172

132 Chesapeake Estates Dr, Stevensville

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$90,000
3 Beds ⋅ 2 Baths
You'll be pleasantly surprised by the space, versatility, and value this well-maintained manufactured home has to offer. A charming paver walkway welcomes you to the front entrance, where you're greeted by a bright, inviting living room filled with natural light. Elegant etched-glass accents lead to the formal dining room, a flexible space that could also serve as a home office or hobby room. The heart of every home is the kitchen and this home is no exception with warm barnwood accents, abundant cabinetry, a center island with an additional prep sink, and an open layout that flows seamlessly into the breakfast nook and comfortable family room—perfect for everyday living and entertaining. A conveniently located laundry room adds everyday practicality, while the family room opens to a relaxing enclosed Florida room, providing even more year-round living space. Situated along the outer edge of the Grantville Commons community, this home enjoys added privacy, making the rear deck an ideal place to unwind or entertain outdoors. The generously sized primary suite offers a relaxing retreat with a spacious en suite bath featuring a deep jetted tub, large vanity, and plenty of space. The two additional bedrooms are amply sized and provide generous closet space and are conveniently located near the updated full hall bath. With its flexible floor plan, thoughtful updates, and desirable location within the community, this affordable home is ready to welcome its next owner. Buyer must be approved by the park.

303 Dallas Dr, Grantville

Listing courtesy of RE/MAX Delta Group, Inc.. Contact: 7176528200
$12,500
ABSOLUTE ONLINE REAL ESTATE AUCTION TO THE HIGHEST BIDDER OVER $12,500! Online Bidding Opens - Wednesday, August 12, 2026. Online Bidding Closes - Thursday, August 13, 2026 at 11:00 AM. List price is opening bid only. Two adjoining unimproved residential lots totaling 0.696 acre, more or less, offered as an entirety in the Chesapeake Estates subdivision of Stevensville, Maryland. Situated on Kent Island in Queen Anne’s County, the property is located within an established residential neighborhood with convenient access to area amenities, waterfront recreation and major commuter routes via U.S. Route 50 and the Chesapeake Bay Bridge. Zoned NC-20 (Neighborhood Conservation), the wooded lots front on Maple Road and Bay Drive, both unimproved paper streets. The auction provides an opportunity to acquire residential land in one of Maryland’s most desirable Eastern Shore communities.

Bay Dr, Stevensville

Listing courtesy of A.J. Billig & Company. Contact:

$67,500
2 Beds ⋅ 2 Baths
Welcome to 157 Linda Dr, New Oxford, PA 17350 — a stunningly renovated 2-bedroom, 1.5-bath mobile home that perfectly blends modern upgrades with warm, inviting charm. Step inside to an expansive open-concept living area featuring handsome exposed beams, a comfortable sectional sofa, and a sleek TV wall that makes entertaining effortless. The kitchen shines with updated stainless steel appliances and is flooded with natural light. Unwind in the spacious bedrooms, complete with generous closet space and soft plush carpeting. The full bathroom offers a beautiful, relaxing shower, while the dedicated laundry room adds everyday convenience. Outside, you’ll enjoy a storage shed, off-street parking, and a dedicated parking pad for two cars. This home is truly move-in ready and packed with character! Water, sewer, and trash are included in the lot rent. Ready for your next chapter? This gem won’t last long — reach out today to make it yours! 🏡✨

157 Linda Dr, New Oxford

Listing courtesy of Coldwell Banker Realty. Contact: (717) 757-2717
$49,900
3 Beds ⋅ 2 Baths
Welcome to 36 Dallas Dr. Grantville in Chesapeake Estates. This 3 bedroom 2 full bath home has a large master suite with vaulted ceilings and it's own full bath. The living space is open and bright. Wood laminate flooring throughout. The front deck measures 20 x 10. Shed stays with the property . New roof installed August 2025. Painted deck and shed in August or 2025. Subject to Park approval. Property sold as is. Water is included in base park fee. Park Base Lot Rent breakdown...$777 ground rent includes water +$65 Sewer +$17.39 Trash, +Storm water $9.63 = total a month $869.02 includes w/s/t /sw. See Bright documents for Park Community Rules and Regulations.

36 Dallas Dr, Grantville

Listing courtesy of RE/MAX Pinnacle. Contact: 7175692222
$90,000
3 Beds ⋅ 2 Baths
Wonderfully landscaped and spacious 3 bedroom 2 bathroom handicap-accessible manufactured home in Chesapeake Estates! Upon entry up the front ramp, you'll notice the lovely spacious front deck. The oversized living room, complete with a ceiling fan, opens to the gorgeous kitchen with stainless steel appliances including the propane-fired cooktop. Just beyond the dining room is the huge primary bedroom complete with access to the primary bath featuring a double sink. Two additional bedrooms and a full bathroom are located at the other end of the home down a wide hallway. Outside, you'll love relaxing on the lovely deck and the storage shed is a great place to store lawn tools! Recently upgraded air conditioner. Property sold as-is.

34 Buddy Blvd, Chesapeake City

Listing courtesy of RE/MAX Chesapeake. Contact:

$67,500
3 Beds ⋅ 2 Baths
53 Sherill Drive, New Oxford, PA 17350 MOTIVATED SELLER! ✅ Welcome home to this charming 3-bedroom, 2-bathroom single-wide manufactured home on a premium corner lot in a friendly, well-maintained community! This beautifully maintained home boasts excellent curb appeal featuring light-colored siding, a covered front porch, and a spacious wooden deck — perfect for morning coffee or evening relaxation. The desirable corner lot provides significantly more outdoor space for entertaining, gardening, or enjoying the fresh air. Seller has also installed electric baseboard heating for the property! Recent Updates: * New metal roof (2020) * Bathroom remodel with new drywall * New flooring throughout * New water heater (2025) Key Features: * 3 generously sized bedrooms * 2 full bathrooms * Open living and kitchen areas filled with natural light * Appliances included: stove, refrigerator, washer, and dryer * Prime corner lot with extra yard space * Driveway for convenient parking * Additional storage shed The home offers a comfortable, open layout with a 100-amp electrical service and circuit breaker panel. Move-in ready and well-cared-for, this property combines comfort, recent improvements, and excellent outdoor space. Water, sewer, and trash are all included in the lot rent! Whether you’re buying your first home, downsizing, or looking for a low-maintenance lifestyle with room to enjoy the outdoors, this one checks all the boxes. Don’t miss your opportunity to own this gem in New Oxford!

53 Sherill Dr, New Oxford

Listing courtesy of Coldwell Banker Realty. Contact: (717) 757-2717
$500,000
3 Beds ⋅ 3 Baths
LEAST EXPENSIVE BRAND NEW HOME ON KENT ISLAND! Ready to move in! Located in Chesapeake Estates! Short drive to Route 50 than most other new construction in Stevensville. House is well appointed with LVP throughout the 1st floor and bathrooms, quartz countertops, full kitchen appliance suite, white shaker cabinets, large window at the kitchen sink, front porch, and more. The home is located on a very quiet, private street with minimal traffic. Energy efficient new home for low maintenance and low energy bills. Can close in 30 days or less!

111 Chestnut Rd, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$459,900
3 Beds ⋅ 2 Baths
*BACK ON THE MARKET - BUYER HOME SALE CONTINGENCY FELL THROUGH! Welcome to this beautifully renovated and remodeled 3-bedroom, 2-bath home offering the perfect blend of modern style, comfort, and location. Designed with today’s lifestyle in mind, this home features a bright open floor plan with spacious living and dining areas that flow seamlessly into the stunning gourmet kitchen. The kitchen is a true showstopper with elegant quartz countertops, a large center island, and ample space for cooking, gathering, and entertaining. Both full bathrooms have been tastefully updated with ceramic tile finishes and brand-new high-end vanities. The spacious primary suite offers a private retreat with its own en-suite bathroom for added comfort and convenience. Step outside to enjoy the level front and backyard spaces, ideal for outdoor entertaining, gardening, play, or simply relaxing. Located just one block from the Chesapeake Bay, you’ll love the nearby neighborhood waterfront park featuring picnic areas and fishing access. Conveniently situated for commuters, this home offers easy access to the Eastern Shore beaches, Washington, DC, and Baltimore—making it the perfect place to enjoy coastal living with city convenience. Don’t miss this exceptional opportunity!

109 Birch Rd, Stevensville

Listing courtesy of Five Star Real Estate. Contact:

$450,000
3 Beds ⋅ 2 Baths
Nestled in a serene setting, this exquisite rambler home, thoughtfully renovated in 2007, offers a perfect blend of comfort and luxury. With three spacious bedrooms and two full bathrooms, this residence is designed for both relaxation and entertaining, making it an ideal retreat for those seeking an elevated lifestyle. Step inside to discover a warm and inviting interior, where traditional floor plans meet modern conveniences. The heart of the home features a beautifully appointed kitchen, complete with upgraded countertops, an island for casual dining, and ample table space for gatherings. Recessed lighting and ceiling fans enhance the ambiance, The bathrooms are designed with luxury in mind, featuring a walk-in shower and a tub shower, providing a spa-like experience at home. 2 of the 3 bedrooms boasts generous walk-in closets, ensuring ample storage and organization. Outside, the property is equally impressive. Set on a spacious 0.38-acre lot, the exterior features include a charming patio, perfect for al fresco dining or morning coffee, and an awning that provides shade on sunny days. The well-maintained landscaping is complemented by an outbuilding, offering additional storage or a workshop for hobbies. An asphalt driveway accommodates up to five vehicles, ensuring convenience for you and your guests. For those who appreciate the tranquility of water, this home is just moments away from the bay, providing opportunities for leisurely strolls along the water's edge or enjoying the soothing sounds of nature. The property is equipped with an electric alarm system, ensuring peace of mind while you enjoy your luxurious surroundings. this home has had many upgrades newer roof, newer HVAC. Crawl space has been incapsulated . New flooring in all bedrooms has just been completed. Home is being sold as-is.

101 Chestnut Rd, Stevensville

Listing courtesy of RE/MAX Realty Group. Contact:

$450,000
3 Beds ⋅ 3 Baths
MOTIVATED SELLER - PRICE REDUCED $50,000 and a NEW 50 YEAR WARRANTY ROOF JUST INSTALLED. Welcome to your new home in one of Stevensville’s water-oriented communities. This 3-bedroom, 3-bath home has much to offer. Additional unfinished space to add up to 2 additional bedrooms. The spacious living areas are perfect for entertaining. Lower-level family room with fireplace and wet bar. Also, an indoor hot tub. Oversized attached garage with room for all your toys. Outdoors, enjoy your own personal oasis with privacy— deck and patio, an above ground pool and fenced backyard, ideal for summer cookouts and relaxation. The property sits in a water-privileged neighborhood with access to neighborhood water front park with tot-lot. Perfect for sunset views over the Chesapeake Bay. Start experiencing Eastern Shore living. Sewer is coming to the neighborhood. Hurry this one will not last.

117 Bay Dr, Stevensville

Listing courtesy of RE/MAX One. Contact: 4102244400
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