Luxury homes for sale & real estate in 21661, MD

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ABOUT THIS HOME
Luxury Home for sale in 21661, MD:
Located along Shipyard Creek just outside Rock Hall, this 113-acre farm offers a strong combination of productive soils, waterfront access, and long-term investment value. The property includes approximately 100 tillable acres with primarily Mattapex soils— moderately well-drained and highly rated for grain and forage production. The balance consists of woodland providing natural buffers between the creek and fields as well as quality wildlife habitat. Improvements include a 3,200 square foot Colonial Revival home and versatile shop. Both lay along 1,500 feet of shoreline steps away from a private dock offering 4'+ MLW. Farms of this size and quality rarely become available in Kent Co

$2,950,000

6 beds1.5 baths3,200 sq ft

Undisclosed address, Rock Hall, MD 21661

Private dock • Waterfront access • Productive soils

(410) 778-3779

ABOUT THIS HOME
Luxury Home for sale in 21661, MD:
Unique opportunity offering two adjoining parcels with exceptional potential in Rock Hall. Parcel 1 consists of approximately 1.4 acres located on Geen Lane and is zoned Critical Area Residential. Improvements include the foundation of a pre-existing structure, an existing well, and a grinder pump connected to public sewer already installed. Buyer to verify well usability and buildability. Parcel 2 is accessed through Parcel 1 and consists of approximately 9 acres with 706 feet of shoreline per survey plat. Zoned Commercial Critical Area (CAR) and Marine (M), this parcel offers a wide range of potential commercial and marine-related uses. Excellent opportunity for investors, marina-related

$850,000

Land10.40 acres (lot)

21190 Green Ln, Rock Hall, MD 21661

Existing well • Listed 100 days

(410) 639-4003

ABOUT THIS HOME
Luxury Home for sale in 21661, MD:
Over half an acre of prime bayfront property! Build a beautiful home on popular Lawton Avenue, the Gratitude neighborhood in Rock Hall. Enjoy sunsets, spectacular views of the bay, and additional views of Swan Creek in back. Spend idyllic afternoons watching the boats sail by! Lawton Ave offers privacy, but is only a short stroll to multiple restaurants, the town beach, and many marinas; there is a private marina just across the street! Town water and sewer is already installed on site. Federal permission has been granted for a 200 ft long, 6 ft wide pier with a T-dock at the end. There would be approx. 5 ft mean low water depth at end of the pier. Buyer to obtain local permits for dock.

$1,125,000

Land0.51 acre (lot)

#2 Lawton Ave, Rock Hall, MD 21661

6 ft wide pier • Views of the bay • Private marina

(410) 639-2118

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ABOUT THIS HOME
Luxury Home for sale in 21661, MD:
Welcome to 148 Elinor Street, where timeless coastal style meets a beautifully reimagined interior in the sought-after waterfront community of Gibson’s Grant. This 3-bedroom, 2.5-bath Hartley model by Koch Homes underwent an extensive renovation in 2025, creating a truly turnkey home filled with thoughtful upgrades, designer finishes, and exceptional attention to detail. Step inside to refinished and newly stained hardwood floors, fresh designer paint, upgraded lighting, new interior doors with Emtek hardware, and a beautifully updated staircase. The dining room was opened to create a more connected, airy flow, while upgraded recessed lighting and Lutron Caséta switches add mod

$899,000

3 beds2.5 baths2,464 sq ft

148 Elinor St, Chester, MD 21619

Updated staircase • Extensive renovation • Upgraded lighting

(703) 378-8810

ABOUT THIS HOME
Luxury Home for sale in 21661, MD:
Be part of the fastest growing 55+ community on Marylands Eastern Shore. Bayberry was the first street in Four Seasons Kent Island where construction in 2021 was superior to those today. 320 Bayberry Drive sits on a Premium Lot which abuts lands owned and maintained by the HOA. The developer is charging a Lot Premium of up to $400,000 for the extra space on remaining lots. The seller just completed $80,000 in renovations. Most of the Furniture can be purchased for below half of what it’s value. The optional sunroom area was completely finished as additional living space. There is a massive 256 square foot rear patio with low V lighting and two raised garden beds. Another HOA area is

$897,750

3 beds2 baths2,331 sq ft

320 Bayberry Dr, Chester, MD 21619

Recent renovations • Raised garden beds • Premium lot

(410) 486-4504

VIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in 21661, MD:
Welcome to Four Seasons at Kent Island, where luxury waterfront living meets the ease of a premier 55+ lifestyle on the shores of the Chester River. Offering breathtaking, unobstructed water views and exceptional community amenities, this beautifully appointed three-bedroom, two-and-a-half-bath condominium is designed for those who appreciate comfort, elegance, and low-maintenance living. The light-filled, open-concept floor plan showcases luxury vinyl plank flooring throughout, recessed lighting, and expansive windows that capture stunning views of the Chester River from nearly every angle. The spacious living room is anchored by a cozy electric fireplace and flows seamlessly into the dini

$859,500

3 beds2.5 baths2,602 sq ft

201 Switchgrass Way #34, Chester, MD 21619

Expansive windows • Gas fireplace • Waterfront living

(410) 280-5600

ABOUT THIS HOME
Luxury Home for sale in 21661, MD:
Bring your water toys and move right in! Located on the Chester River, this beautifully remodeled water front home is ready for a quick sale so you can enjoy the rest of the prime season! Private pier with 10k lb boat lift and 2 jet ski lifts, built in 2021. Open deck with spectacular views of the sunsets! Inside the home has been upgraded with all new hard surface flooring and neutral decor. A modern kitchen with SS appliances including gas stove, painted wood cabinetry, quartz countertop with bar and pantry. Open concept floor plan with water views from all rooms in the rear. Large dining area opens to the living area with gas fireplace. Sliders are on the entire back of the home offering

$899,000

3 beds2 baths1,612 sq ft

942 Chester River Dr, Grasonville, MD 21638

Boat lift • Quartz countertop • Water front home

(240) 456-0016

ABOUT THIS HOME
Luxury Home for sale in 21661, MD:
Welcome to 214 Bayberry at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Killarney model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary suite, guest bedroom, and a private home office - perfect for working from home or hosting visitors in a den setting. The Gourmet Kitchen is special, boasting upgraded appliances, expansive quartz counter tops, custom cabinetry, double wall ovens, stainless steel refrigerator with French doors, and

$924,000

3 beds3 baths2,745 sq ft

214 Bayberry Dr, Chester, MD 21619

Spa style bathroom • Screened-in porch • Gourmet kitchen

(410) 822-6665

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in 21661, MD:
The Kerr Model Home offers a beautifully crafted layout enhanced with elevated designer finishes throughout—available now for immediate settlement with a rent-back opportunity. Thoughtfully designed with 3 bedrooms, 3 baths, and a 3-car garage, this home blends spacious living, refined styling, and everyday functionality. Standout features include a dedicated home office, an inviting fireplace, and professionally designed details such as a feature wall, crown molding, and sliding barn doors that add custom character to each space. As an added benefit, all model home furniture is included, providing a fully move-in-ready experience. The gourmet kitchen is equipped with a Profile range,

$1,100,000

3 beds3 baths2,789 sq ft

123 Flycatcher Way, Chester, MD 21619

Sliding barn doors • Feature wall • Inviting fireplace

(410) 208-3500

Property at 117 Flycatcher Way, Chester, MD 21619, 3 beds, 3.5 baths

$1,200,000

3 beds3.5 baths2,930 sq ft

117 Flycatcher Way, Chester, MD 21619

(410) 208-3500

Property at 111 Flycatcher Way, Chester, MD 21619, 5 beds, 4.5 baths

$1,200,000

5 beds4.5 baths3,225 sq ft

111 Flycatcher Way, Chester, MD 21619

(410) 208-3500

Property at 111 Marshgrass Way #41, Chester, MD 21619, 3 beds, 2.5 baths

$998,000

3 beds2.5 baths— sq ft

111 Marshgrass Way #41, Chester, MD 21619

(410) 770-3600

Property at 102 Boatswain Way #2943, Chester, MD 21619, 2 beds, 2.5 baths

$919,990

2 beds2.5 baths1,900 sq ft

102 Boatswain Way #2943, Chester, MD 21619

(410) 208-3500

Property at 323 Kingfisher Ln, Chester, MD 21619, 5 beds, 4.5 baths

$949,990

5 beds4.5 baths3,225 sq ft

323 Kingfisher Ln, Chester, MD 21619

(410) 208-3500

Property at 532 Warbler Way, Chester, MD 21619, 3 beds, 3 baths

$899,990

3 beds3 baths2,772 sq ft

532 Warbler Way, Chester, MD 21619

(410) 208-3500

Property at 540 Warbler Way, Chester, MD 21619, 3 beds, 3 baths

$929,990

3 beds3 baths2,789 sq ft

540 Warbler Way, Chester, MD 21619

(410) 208-3500

Property at 104 Port Ct, Grasonville, MD 21638, 4 beds, 2.5 baths

$1,275,000

4 beds2.5 baths3,069 sq ft

104 Port Ct, Grasonville, MD 21638

(410) 260-2800

Property at 952 Chester River Dr, Grasonville, MD 21638, 5 beds, 3.5 baths

$1,400,000

5 beds3.5 baths3,500 sq ft

952 Chester River Dr, Grasonville, MD 21638

(703) 378-8810

Property at 109 Starboard Ct, Grasonville, MD 21638, 5 beds, 4.5 baths

$1,470,000

5 beds4.5 baths4,418 sq ft

109 Starboard Ct, Grasonville, MD 21638

(410) 531-0321

Property at 8796 Maryland Pkwy, Chestertown, MD 21620, 9 beds, 6.5 baths

$1,495,000

9 beds6.5 baths4,776 sq ft

8796 Maryland Pkwy, Chestertown, MD 21620

(410) 778-0330

Property at 233 Kingfisher Ln, Chester, MD 21619, 5 beds, 4.5 baths

$999,000

5 beds4.5 baths3,225 sq ft

233 Kingfisher Ln, Chester, MD 21619

(703) 378-8810

Property at 215 Kingfisher Ln, Chester, MD 21619, 5 beds, 4.5 baths

$995,000

5 beds4.5 baths3,225 sq ft

215 Kingfisher Ln, Chester, MD 21619

(443) 274-1900

Property at 350 Narrows Pointe Dr, Grasonville, MD 21638, 3 beds, 3.5 baths

$1,215,000

3 beds3.5 baths2,742 sq ft

350 Narrows Pointe Dr, Grasonville, MD 21638

(410) 295-6579

Luxury Homes for Sale in 21661

There are currently 3 luxury homes for sale in 21661 at a median listing price of $399K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 21661 stay on the market for 70 days. This map is refreshed with the newest listings in 21661 every 15 minutes.

In the past month, 4 homes have been sold in 21661. In addition to houses in 21661, there were also 0 condos, 6 townhouses, and 0 multi-family units for sale in 21661 last month. Find your dream home in 21661 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 21661 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 21661. If you're looking to sell your home in the 21661 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 21661 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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