Luxury homes for sale & real estate in 21666, MD

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COMING SOON

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
This gorgeous home is COMING SOON! Exceptional home in an exceptional community. Move in and enjoy the view. Every detail has been acknowledged and updated or replaced. Updated kitchen cabinets and counters, induction stove, tankless water heater, salt water pool, master bath upgrade, new carpet and it goes on and on! Large rooms can accommodate family and friends and the owned solar panels provide no electric bill! From the outside in, every inch has been touched from the beautiful landscaping to the interior window treatments. Value in every corner!! I can't wait to show it to you!!!

$1,025,000

5 beds2.5 baths3,300 sq ft

201 Mallard Dr, Stevensville, MD 21666

Induction stove • Master bath upgrade • Salt water pool

(410) 643-2244

OPEN TODAY, 12PM TO 3PM

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
105 Night Heron is a substantially expanded and renovated home offering more than 4400 square feet of finished living space plus an additional 850 square feet of finished, conditioned, multi-purpose garage space. The property features expansive water views and numerous high end finishes including custom Omega cabinetry, granite and black walnut countertops, extensive built-ins, premium Miele, Viking and Sharp appliances, hardwood and limestone flooring, Kohler fixtures, a custom coffered bar-room ceiling, a 500-bottle wine storage room, and extensive recess lighting. The main floor boasts a dream kitchen with breakfast area and fireplace and a formal dining room off the foyer with designer

$1,675,000

3 beds3 baths4,419 sq ft

105 Night Heron Ct, Stevensville, MD 21666

0.85 acre lot • 3 garage spots • Built 1999

(410) 643-2244

OPEN AUG 29, 11AM TO 1PM

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
Tucked between the tranquil waters of Long Creek and Shipping Creek, this approximately 2,100 square-foot waterfront retreat offers a rare blend of mid-century charm and modern comfort. With three bedrooms and three full bathrooms, there's plenty of space to live, relax, and host with ease. Originally built in 1977 and thoughtfully renovated in 2019, the home showcases timeless mid-century design — clean lines, an inviting flow, and character you can't replicate in new construction. A brand-new well pump (2025) adds peace of mind, ensuring reliable, efficient water service for years to come. The primary bedroom offers a true private retreat, while the additional bedrooms and full bath

$1,250,000

3 beds3 baths1,950 sq ft

408 Butlers Lndg, Stevensville, MD 21666

Private dock • Mature landscaping • Waterfront retreat

(410) 263-8686

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
Welcome to 92 Long Creek Drive, an extraordinary Kent Island waterfront estate where luxury living meets exceptional investment potential. Perfectly positioned on more than 2.5 private acres with approximately 250 feet of shoreline, this remarkable property offers the opportunity to enjoy a waterfront retreat while benefiting from an established, successful short-term vacation rental with proven income history. Profit and loss statements are available upon request, and the home is available fully furnished for a truly turnkey experience. Spanning nearly 4,000 square feet across four finished levels, the home features five bedrooms, four full baths, multiple living and entertaining spaces, a

$1,995,000

5 beds4.5 baths4,056 sq ft

92 Long Creek Dr, Stevensville, MD 21666

Private acres • In-ground pool • Waterfront estate

(410) 822-6665

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
Nestled within the prestigious Wolf Farm community, this exquisite residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. This property is one of few on Kent Island that has unobstructed views of Annapolis, Baltimore and the Chesapeake Bay Bridge. Guests are welcomed with a gated circular drive adorn with stone pillars, lush flower beds and a professionally manicured lawn. The neoclassical architectural style mimics that of Thomas Jeffersons home Monticello. Spanning an impressive 10,152 square feet, the kitchen has been meticulously renovated in 2026, ensuring convenience of use while gazing at the Bay. Step inside to discover an open fl

$4,158,000

9 beds8 baths10,152 sq ft

319 Blue Bay Rd, Stevensville, MD 21666

2.78 acre lot • 2 garage spots • Pool

(410) 643-2244

Property at 414 Bay Dr, Stevensville, MD 21666, 5 beds, 7 baths

$2,888,000

5 beds7 baths6,148 sq ft

414 Bay Dr, Stevensville, MD 21666

(410) 823-0033

Property at 225 Batts Neck Rd, Stevensville, MD 21666, 3 beds, 2.5 baths

$899,000

3 beds2.5 baths2,353 sq ft

225 Batts Neck Rd, Stevensville, MD 21666

(855) 450-0442

Property at 1130 Old Love Point Rd, Stevensville, MD 21666, 3 beds, 2 baths

$1,900,000

3 beds2 baths1,536 sq ft

1130 Old Love Point Rd, Stevensville, MD 21666

(443) 746-2090

Property at 410 Wallman Way, Stevensville, MD 21666, 9 beds, 3.5 baths

$1,750,000

9 beds3.5 baths4,025 sq ft

410 Wallman Way, Stevensville, MD 21666

(443) 249-7653

Property at 206 Queen Anne Club Dr, Stevensville, MD 21666, 6 beds, 5 baths

$1,990,000

6 beds5 baths4,535 sq ft

206 Queen Anne Club Dr, Stevensville, MD 21666

(410) 643-2244

Property at 121 Eareckson Ln, Stevensville, MD 21666, 4 beds, 2.5 baths

$850,000

4 beds2.5 baths2,141 sq ft

121 Eareckson Ln, Stevensville, MD 21666

(410) 643-2244

Property at 123 Petrie Way, Stevensville, MD 21666, 4 beds, 4 baths

$2,375,000

4 beds4 baths3,280 sq ft

123 Petrie Way, Stevensville, MD 21666

(410) 280-5600

Property at 410 5 Farms Dr, Stevensville, MD 21666, 4 beds, 2.5 baths

$949,000

4 beds2.5 baths2,047 sq ft

410 5 Farms Dr, Stevensville, MD 21666

(410) 263-8686

Property at 107 Petrie Way, Stevensville, MD 21666, 4 beds, 4 baths

$2,375,000

4 beds4 baths3,280 sq ft

107 Petrie Way, Stevensville, MD 21666

(410) 280-5600

Property at 313 Columbia Ln, Stevensville, MD 21666, 3 beds, 3 baths

$875,990

3 beds3 baths2,230 sq ft

313 Columbia Ln, Stevensville, MD 21666

(301) 702-4200

Property at 119 Petrie Way, Stevensville, MD 21666, 4 beds, 4 baths

$2,375,000

4 beds4 baths3,280 sq ft

119 Petrie Way, Stevensville, MD 21666

(410) 280-5600

Property at 115 Petrie Way, Stevensville, MD 21666, 4 beds, 4 baths

$2,375,000

4 beds4 baths3,280 sq ft

115 Petrie Way, Stevensville, MD 21666

(410) 280-5600

Property at 416 5 Farms Dr, Stevensville, MD 21666, 4 beds, 2.5 baths

$969,000

4 beds2.5 baths2,656 sq ft

416 5 Farms Dr, Stevensville, MD 21666

(410) 263-8686

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ABOUT THIS HOME
Luxury Home for sale in 21666, 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 21666, 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 21666, 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 21666, 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

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio that extends your living space outdoors. Thoughtful design details—such as barn doors, crown molding, and a custom feature wall—add character and craftsmanship throughout. As an added bonus, all model home furniture is included, offering a seamless move-in-ready experience. The be

$1,200,000

3 beds3.5 baths2,930 sq ft

117 Flycatcher Way, Chester, MD 21619

Screened patio • Barn doors • Cozy fireplace

(410) 208-3500

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
The Tuscaloosa Model Home offers an exceptional open-concept design enriched with high-end finishes and thoughtful upgrades throughout. Available for immediate settlement with a rent-back opportunity, this expansive home features 5 bedrooms, 4.5 baths, and a 3-car garage, delivering both space and sophistication. Standout features include a dedicated home office, an inviting fireplace, and a screened patio perfect for indoor–outdoor living. Custom design elements—such as barn doors, ceiling beams, and a striking feature wall—bring warmth, character, and craftsmanship to every corner. As a premium bonus, all model home furniture is included, providing a fully move-in-ready

$1,200,000

5 beds4.5 baths3,225 sq ft

111 Flycatcher Way, Chester, MD 21619

Open-concept design • Screened patio • Inviting fireplace

(410) 208-3500

Property at 113 Bentons Pleasure Rd, Chester, MD 21619, 4 beds, 2.5 baths

$868,000

4 beds2.5 baths3,168 sq ft

113 Bentons Pleasure Rd, Chester, MD 21619

(410) 823-0033

Property at 2702 Sherman Dr, Chester, MD 21619, 5 beds, 3 baths

$989,000

5 beds3 baths2,752 sq ft

2702 Sherman Dr, Chester, MD 21619

(703) 378-8810

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 203 Riverside Dr, Chester, MD 21619, 5 beds, 3.5 baths

$989,800

5 beds3.5 baths3,036 sq ft

203 Riverside Dr, Chester, MD 21619

(301) 945-9010

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 300 Woods Point Rd, Chester, MD 21619, 3 beds, 2 baths

$2,840,000

3 beds2 baths1,704 sq ft

300 Woods Point Rd, Chester, MD 21619

(410) 827-8877

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 330 Serenity Ln, Chester, MD 21619, 7 beds, 8 baths

$5,400,000

7 beds8 baths10,667 sq ft

330 Serenity Ln, Chester, MD 21619

(410) 280-5600

Property at 2855 Cox Neck Rd, Chester, MD 21619, 4 beds, 4.5 baths

$1,195,000

4 beds4.5 baths4,413 sq ft

2855 Cox Neck Rd, Chester, MD 21619

(410) 304-2250

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 1757 Harbor Dr, Chester, MD 21619, 4 beds, 3.5 baths

$1,294,800

4 beds3.5 baths— sq ft

1757 Harbor Dr, Chester, MD 21619

(410) 729-7700

Luxury Homes for Sale in 21666

There are currently 18 luxury homes for sale in 21666 at a median listing price of $597K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 21666 stay on the market for 65 days and receive 1 offers. This map is refreshed with the newest listings in 21666 every 15 minutes.

In the past month, 26 homes have been sold in 21666. In addition to houses in 21666, there were also 2 condos, 31 townhouses, and 0 multi-family units for sale in 21666 last month. Find your dream home in 21666 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 21666 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 21666. If you're looking to sell your home in the 21666 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 21666 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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