Chesapeake Estates Real Estate

Chesapeake Estates Real Estate

Welcome to Chesapeake Estates, a hidden gem nestled in the heart of the United States, where suburban charm meets modern living. This picturesque subdivision offers a perfect blend of tranquility and convenience, making it an ideal place for families, young professionals, and retirees alike.

Chesapeake Estates boasts beautifully landscaped streets lined with elegant homes that exude character and warmth. Each residence has been thoughtfully designed, featuring spacious layouts, contemporary finishes, and inviting outdoor spaces that encourage relaxation and connection with nature. Here, you’ll find a variety of architectural styles, ensuring there’s a perfect fit for everyone’s taste.

One of the standout features of Chesapeake Estates is its commitment to community. Residents enjoy access to well-maintained parks, walking trails, and recreational facilities, fostering a sense of togetherness and an active lifestyle. Family-friendly amenities, such as playgrounds and picnic areas, make it easy to spend quality time with loved ones.

Conveniently located, Chesapeake Estates offers easy access to major highways, ensuring that shopping, dining, and entertainment options are just a short drive away. Local schools are highly regarded, providing excellent educational opportunities for children.

Whether you're looking to settle down or invest in a thriving community, Chesapeake Estates is a place where you can truly feel at home. Experience the perfect balance of serene living and vibrant community life in this charming subdivision. Come and discover the welcoming embrace of Chesapeake Estates, where your dream home awaits!

Newest Listings in Chesapeake Estates

$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:

$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 manufactured home in Chesapeake Estates! The entry is handicap accessible with a ramp to the front door. 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. 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:

$70,000
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
$499,900
3 Beds ⋅ 3 Baths
Brand new home ALMOST COMPLETE in Chesapeake Estates! Shorter 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:

$460,000
3 Beds ⋅ 3 Baths
MOTIVATED SELLER - PRICE REDUCED $40,000 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
Start Your Search