Luxury homes for sale & real estate in 21666, MD

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ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
Unobstructed, breathtaking views of the Chesapeake Bay! This stunning and newly remodeled waterfront home sits on a double lot along one of the most picturesque and peaceful streets—just minutes from the Bay Bridge yet worlds away from it all. A new rip rap shoreline and 350 feet of water frontage create a private, protected setting enhanced by mature landscaping and a spacious, level yard with a fire pit, large shed, and plenty of room for a future pool. Enjoy easy access to the water from your private pier with an 8,000 lb boat lift and multiple slips, perfect for boating and exploring the Bay. Inside, walls of floor-to-ceiling windows frame endless views across the water to the sho

$2,495,000

4 beds4.5 baths4,906 sq ft

205 Lighthouse View Dr, Stevensville, MD 21666

2.65 acre lot • 2 garage spots • Car-dependent

(410) 280-5600

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
MATAPEAKE ESTATES NEIGHBORHOOD unrivaled panoramic views across the Bay to Annapolis and Naval Academy, glorious sunset views and southwesterly breezes - every day feels like a vacation. Conveniently located just minutes from the Bay Bridge or Rt 301/50/404 , community beach, boat ramp, Golf Course, marinas , stores and close proximity to daily catch eateries, nature/recreational parks , the Kent Island Trail and the Matapeake beach and Beach Club. This solid brick rancher has been updated in 2018, there is a second story suite , the floorplan was transformed to an open floor plan with gleaming white kitchen cabinets , 2 bricked fireplaces and a wonderful spacious all season sun room. The

$1,198,000

4 beds3 baths2,740 sq ft

96 Annapolis View Rd, Stevensville, MD 21666

0.72 acre lot • 2 parking spots • Built 1979

(410) 745-0283

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
Beautiful contemporary with soaring ceilings, hardwood floors and wall of glass looking out to the waterfront pool and sweeping views of Broad Creek. Protected water, yet a quick trip to the Bay. Home includes the open floorplan everyone wants. New three season sunroom poolside is great for cracking crabs. First floor office can be used as a bedroom, with a full bath just around the corner. The main level flows out effortlessly to extensive decking overlooking the large pool and new gazebo. Pavers take you down to the waterfront firepit and out to a freshly decked dock that includes boat lift, two jet ski lifts and a nice seating area. Large primary bedroom has great water views and a scrum

$1,849,000

4 beds3 baths3,063 sq ft

802 Broadcreek Dr, Stevensville, MD 21666

0.34 acre lot • 2 garage spots • Pool

(410) 263-8686

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
Welcome to your new waterfront home! Nestled on over 2 acres of prime waterfront on Shipping Creek. This property offers so much. Mature landscaping with sprinkler system to keep your lawn and landscaping lush. Beautifully appointed home with gourmet kitchen with open floor plan make this a prime area for entertaining. Did I mention the double-sided fireplace in the living/ dining area, with a wet bar that offers a wine fridge and icemaker. The primary suite offers a gorgeous primary bath with walk in shower and soaking tub with endless views of the creek. The primary suite also has huge walk-in closet and private screened in porch to take in your morning coffee. Two additional bedrooms off

$1,525,000

3 beds2.5 baths2,246 sq ft

124 Eareckson Ln, Stevensville, MD 21666

2.1 acre lot • 3 garage spots • Built 1983

(410) 758-0333

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
Waterfront Living at Its Finest! This beautifully renovated home offers stunning water views from most rooms, creating a serene retreat filled with natural light. The gourmet kitchen with breakfast area flows seamlessly into the dining room and spacious living areas, perfect for both entertaining and everyday living. Inside, you’ll find four bedrooms, two full baths, and two half baths, along with hardwood floors throughout most of the house, vaulted ceilings, and two fireplaces adding warmth and charm. A versatile sunroom/playroom with heat and air opens directly to the outdoor space, extending your living options year-round. Enjoy the outdoors from your private pier on Shipping Cree

$1,275,000

4 beds3 baths3,345 sq ft

100 Eareckson Ln, Stevensville, MD 21666

1.3 acre lot • 2 garage spots • Built 1984

(410) 224-2200

Property at 216 Lighthouse View Dr, Stevensville, MD 21666, 4 beds, 4.5 baths

$2,485,000

4 beds4.5 baths4,138 sq ft

216 Lighthouse View Dr, Stevensville, MD 21666

(410) 280-5600

Property at 200 Bridgeview Ln, Stevensville, MD 21666, 8 beds, 8.5 baths

$14,950,000

8 beds8.5 baths20,013 sq ft

200 Bridgeview Ln, Stevensville, MD 21666

(410) 280-5600

Property at 118 N Lake Dr, Stevensville, MD 21666, 3 beds, 2.5 baths

$929,900

3 beds2.5 baths2,464 sq ft

118 N Lake Dr, Stevensville, MD 21666

(410) 643-5005

Property at 137 Tanners Point Dr, Stevensville, MD 21666, 5 beds, 3.5 baths

$2,995,000

5 beds3.5 baths4,897 sq ft

137 Tanners Point Dr, Stevensville, MD 21666

(410) 280-5600

Property at 200 Mallard Cove Ln, Stevensville, MD 21666, 4 beds, 4 baths

$3,725,000

4 beds4 baths5,900 sq ft

200 Mallard Cove Ln, Stevensville, MD 21666

(410) 770-9255

Property at 231 Lighthouse View Dr, Stevensville, MD 21666, 5 beds, 4.5 baths

$3,950,000

5 beds4.5 baths5,593 sq ft

231 Lighthouse View Dr, Stevensville, MD 21666

(301) 745-5500

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

$899,900

4 beds2.5 baths2,047 sq ft

410 5 Farms Dr, Stevensville, MD 21666

(888) 400-2513

Property at Sunset Wharf Lot D-3, Stevensville, MD 21666, 3 beds, 4 baths

$2,375,000

3 beds4 baths3,280 sq ft

Sunset Wharf Lot D-3, Stevensville, MD 21666

(410) 280-5600

Property at Sunset Wharf Lot D-1, Stevensville, MD 21666, 2 beds, 3.5 baths

$2,350,000

2 beds3.5 baths3,280 sq ft

Sunset Wharf Lot D-1, Stevensville, MD 21666

(410) 280-5600

Property at Sunset Wharf Lot D-2, Stevensville, MD 21666, 4 beds, 4 baths

$2,375,000

4 beds4 baths3,280 sq ft

Sunset Wharf Lot D-2, Stevensville, MD 21666

(410) 280-5600

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OPEN SAT, 10:30AM TO 12:30PM

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
Nestled along the serene banks of Coxes Bay, this contemporary home was thoughtfully designed to blend comfort, luxury and the tranquility of nature. Spend the warmer months crabbing, fishing, boating, jet skiing and kayaking off your private pier with 3+ feet mean low water. Within minutes by boat, Cox Creek meets the Eastern Bay for easy access to the Chesapeake Bay or the Narrows. As you approach the front door the views looking in are breathtaking. You'll find yourself entering the bright and airy kitchen with quartz countertops equipped with a 6 burner gas stove, wall oven and high end advantium oven. The oversized island with farmhouse sink creates a warm and welcoming space. The open

$1,050,000

3 beds2.5 baths1,656 sq ft

318 Old Point Rd, Chester, MD 21619

0.31 acre lot • Car-dependent

(410) 224-2200

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
Discover K. Hovnanian's® Four Seasons at Kent Island, a lively community of new condominiums in Chester, MD. Make your move to this active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new waterfront condos with resort-style amenities. Choose from 3, single-story floorplans of up to 2,602 sq. ft. , 3 beds, 2.5 baths, and a 1-car garage. Select plans feature a balcony or porch, to enjoy your waterfront views. Residents can enjoy the clubhouse, resort-style pool, modern fitness center, spacious dog park, open-air amphitheater, fishing and boating pier, tennis and pickleball courts, and so much more, with a schedule of activities organized by the full-time l

$1,350,000

2 beds2.5 baths1,900 sq ft

132 Wheelhouse Way #43, Chester, MD 21619

Car-dependent

Listing provided by Zillow

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
This beautifully designed Chester Model Home offers sophisticated comfort and modern convenience, ready for immediate move-in with a flexible month-to-month leaseback opportunity. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home blends style and function seamlessly. Thoughtful touches include a fully furnished interior, a dry bar perfect for entertaining, and an electric fireplace that adds warmth and ambiance. A dedicated home office with elegant lited French doors provides the ideal space for work or creativity. The gourmet kitchen is equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and a tile backsplash, all accented by quartz c

$1,350,000

2 beds2.5 baths1,900 sq ft

132 Wheelhouse Way, Chester, MD 21619

$601 HOA • Garage • Community pool

(240) 375-5074

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
This stunning Taylor home offers an inviting open floor plan designed for both comfort and functionality. Featuring 2 bedrooms, 2.5 baths, and a spacious 3-car garage, this home perfectly blends everyday ease with elevated style. Highlights include a dedicated home office, a cozy screened patio for outdoor relaxation, and a dramatic 2-story stone fireplace that serves as the heart of the great room. The gourmet kitchen is equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a stylish tile backsplash. Elegant quartz countertops extend through the kitchen and owner’s bath. Luxury vinyl plank flooring enhances the ma

$899,900

2 beds2.5 baths2,010 sq ft

117 Redstart Dr, Chester, MD 21619

7,000 sq ft lot • $263 HOA • 3 garage spots

(240) 375-5074

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
This stunning Kerr home offers an inviting open floor plan designed for both comfort and functionality. Featuring 3 bedrooms, 3 baths, and a spacious 3-car garage, this home perfectly blends everyday ease with elevated style. Highlights include a dedicated home office, a cozy screened patio for outdoor relaxation, and a dramatic 2-story stone fireplace that serves as the heart of the great room. The gourmet kitchen is equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a stylish tile backsplash. Elegant quartz countertops extend through the kitchen and owner’s bath. Luxury vinyl plank flooring enhances the main l

$889,900

3 beds3 baths2,789 sq ft

527 Warbler Way, Chester, MD 21619

7,000 sq ft lot • $263 HOA • 3 garage spots

(240) 375-5074

ABOUT THIS HOME
Luxury Home for sale in 21666, MD:
An impressive open two-story foyer welcomes you to this custom 4 BR, 3.5BA waterfront residence on 1.9 acres boasting an enchanting open space floorplan. A first floor Ensuite BR has a walk-in closet plus a separate jacuzzi and shower in the updated full bath. The sumptuous approximately 39'X26' Primary Suite with a large sitting room area offers front and rear balconies specifically designed by the Architect to enjoy the breathtaking sunrises, moonrises & sunsets lighting the Bay with bright pink and orange skies and brilliantly lit sparkling water. This second floor Primary Suite has a Cathedral ceiling, a 3-sided gas fireplace and a fully renovated Coastal style bath which includes

$2,259,000

4 beds3.5 baths5,122 sq ft

2865 Cox Neck Rd, Chester, MD 21619

1.9 acre lot • $144 HOA • 3 garage spots

(410) 721-1500

Property at 519 Warbler Way, Chester, MD 21619, 3 beds, 3 baths

$899,900

3 beds3 baths2,789 sq ft

519 Warbler Way, Chester, MD 21619

(240) 375-5074

Property at 132 Kestrel Ln, Chester, MD 21619, 4 beds, 3.5 baths

$1,049,000

4 beds3.5 baths3,634 sq ft

132 Kestrel Ln, Chester, MD 21619

(410) 280-5600

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

$1,125,000

4 beds3.5 baths— sq ft

1757 Harbor Dr, Chester, MD 21619

(410) 729-7700

Property at Munich ESP Plan, Chester, MD 21619, 4 beds, 3.5 baths

$883,900

4 beds3.5 baths3,601 sq ft

Munich ESP Plan, Chester, MD 21619

Listing provided by Zillow

Property at Franklin Plan, Chester, MD 21619, 3 beds, 3.5 baths

$858,900

3 beds3.5 baths2,930 sq ft

Franklin Plan, Chester, MD 21619

Listing provided by Zillow

Property at Mykonos Plan, Chester, MD 21619, 4 beds, 3.5 baths

$886,900

4 beds3.5 baths3,512 sq ft

Mykonos Plan, Chester, MD 21619

Listing provided by Zillow

Luxury Homes for Sale in 21666

There are currently 15 luxury homes for sale in 21666 at a median listing price of $575K. 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 76 days and receive 1 offers. This map is refreshed with the newest listings in 21666 every 15 minutes.

In the past month, 21 homes have been sold in 21666. In addition to houses in 21666, there were also 4 condos, 26 townhouses, and 1 multi-family unit 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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