Luxury homes for sale & real estate in 21658, MD

10 homes

Sort:

Recommended

FLOOR PLAN

ABOUT THIS HOME
Luxury Home for sale in 21658, MD:
Wye River Waterfront Living at Its Best! If you love boating, fishing, crabbing, and being on the water, this Cape Cod-style home on the Wye River may be just what you have been waiting for. Situated on 1.46 private acres with more than 250 feet of waterfront, this property offers a peaceful setting surrounded by mature trees, beautiful landscaping, and plenty of privacy. The Wye River is well known for its excellent boating, fishing, and crabbing, along with its deep water that makes it especially appealing to boaters. Whether you are looking for a full-time residence, a second home, or an investment opportunity, this property offers tremendous possibilities. Enjoy the outdoors from the pr

$1,300,000

4 beds2.5 baths2,626 sq ft

117 River Run, Queenstown, MD 21658

Separate game room • New flooring • Wye river waterfront

(410) 224-2200

$1,195,000

4 beds3 baths2,542 sq ft

225 Hickory Ridge Dr, Queenstown, MD 21658

Electric boat lifts • Private dock • Gunite pool

(571) 386-1075

FLOOR PLAN

ABOUT THIS HOME
Luxury Home for sale in 21658, MD:
From the moment you turn onto winding Carmichael Road and cross the bridge onto Wye Island, the pace begins to slow. Of the island’s approximately 2,800 acres, only about 350 are privately owned. The State of Maryland through the Maryland Park Service owns and manages the rest. ‘The Point’ is among the island’s handful of private properties, distinguished by almost six acres and more than 1,200 feet of elevated waterfront, one of the largest private shorelines on Wye Island, with over half riprapped. Set at the end of a private drive, this exceptional estate offers a rare sense of privacy amid the island’s pristine, unspoiled lands. The main residence is distin

$3,850,000

5 beds4 baths3,864 sq ft

491 Wye Island Rd, Queenstown, MD 21658

Guest house • Elevated waterfront • Private duck blind

(301) 967-3344

ABOUT THIS HOME
Luxury Home for sale in 21658, MD:
This is a true coastal retreat, from its stunning exterior to its thoughtfully designed living spaces. A one-of-a-kind waterfront estate, the property offers more than 2,000 feet of shoreline and sits on 5.4 private acres at the end of Kilby Point. Surrounded by water on both the Wye River and Eastern Bay, this exceptional home captures endless panoramic views in every direction. And yes—how many people can say they own a lighthouse? The home has been completely renovated down to the studs, blending timeless coastal charm with modern convenience. Interior features include shiplap walls, beamed ceilings, new flooring, and beautifully reimagined living spaces throughout. The new kitchen

$2,990,000

4 beds6 baths4,903 sq ft

121 Kilby Pt, Queenstown, MD 21658

Waterfront estate • 5.4 private acres • Beamed ceilings

(410) 224-2200

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in 21658, MD:
Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass

$4,695,000

5 beds4.5 baths6,156 sq ft

2800 Bennett Point Rd, Queenstown, MD 21658

17.97 acre lot • 5 garage spots • Pool

(410) 673-3344

Property at 2006 Bennett Point Rd, Queenstown, MD 21658, 4 beds, 3 baths

$1,500,000

4 beds3 baths2,721 sq ft

2006 Bennett Point Rd, Queenstown, MD 21658

(443) 274-1900

Property at 351 Wye Rd, Queenstown, MD 21658, 6 beds, 4 baths

$2,100,000

6 beds4 baths6,340 sq ft

351 Wye Rd, Queenstown, MD 21658

(410) 224-2200

Property at 377 Hemsley Dr, Queenstown, MD 21658, 4 beds, 3.5 baths

$1,895,000

4 beds3.5 baths4,504 sq ft

377 Hemsley Dr, Queenstown, MD 21658

(410) 822-6665

Property at 200 Wye Rd, Queenstown, MD 21658, 6 beds, 5.5 baths

$4,400,000

6 beds5.5 baths8,180 sq ft

200 Wye Rd, Queenstown, MD 21658

(410) 280-5600

Property at 215 Alynn Way, Queenstown, MD 21658, 4 beds, 5 baths

$2,795,000

4 beds5 baths6,338 sq ft

215 Alynn Way, Queenstown, MD 21658

(410) 263-8686

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

VIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in 21658, MD:
PRESQUILE MANOR HOUSE – An extraordinary waterfront estate steeped in history, architectural distinction, and timeless elegance. Magnificently positioned along the Wye River with breathtaking panoramic views and coveted western exposure, this distinguished circa-1800 manor house offers an exceptional combination of historic character, refined luxury, and unparalleled waterfront living. Originally part of the historic Lloyd family holdings, the 10.48-acre estate has been meticulously renovated by renowned Peter Zimmerman Architects and West & Callahan Construction, reflecting an extraordinary commitment to preserving its architectural heritage while incorporating the finest moder

$7,850,000

7 beds7 baths9,322 sq ft

26546 Presquile Farm Dr, Easton, MD 21601

Custom cabinetry • Waterfront estate • Western exposure

(410) 673-3344

OPEN SAT, 2PM TO 4PM3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in 21658, MD:
Some homes are simply places to live. This is a lifestyle. Welcome to 228 Prospect Bay Dr W, an exceptionally maintained and thoughtfully updated home where beautiful water views, resort-style outdoor living, and the coveted Prospect Bay community come together in one unforgettable property. From the moment you arrive, the setting makes an impression. Mature landscaping, a gracious exterior and glimpses of the water create a sense of arrival that feels distinctly Eastern Shore. Step inside and you’ll quickly see that this home has been meticulously cared for and intentionally improved, blending timeless coastal character with sophisticated, modern updates. Hardwood floors extend throu

$1,495,000

5 beds3.5 baths3,707 sq ft

228 Prospect Bay Dr W, Grasonville, MD 21638

Backyard oasis • Guest house • Pool

(443) 274-1900

ABOUT THIS HOME
Luxury Home for sale in 21658, MD:
Enjoy broad water views and spectacular sunsets from this beautifully situated 1.02-acre waterfront property, with water views enjoyed throughout much of the home. Designed for comfortable one-level living, this spacious residence offers 4 bedrooms, 3.5 baths providing 3,137 square feet of living space. The bright kitchen features a skylight, center island with seating, and an open layout connecting seamlessly to the family room with fireplace. The waterfront primary suite takes full advantage of the views and includes a large walk-in closet, private bath with soaking tub, walk-in shower and dual vanities, plus primary has direct access to a semi-private deck. An additional guest bedroom fe

$1,625,000

4 beds3.5 baths3,137 sq ft

251 Prospect Bay Dr W, Grasonville, MD 21638

Bright kitchen • Water views • One-level living

(410) 643-2244

ABOUT THIS HOME
Luxury Home for sale in 21658, MD:
Stock Range Farm spans 350 acres of prime waterfront and is available for purchase in its entirety OR with reduced acreage including the main residence, if the buyer so chooses. Options include selling main residence with 20+ acres, 40+ acres, and 100+ acres. * * CALL listing agent for more information! The property is free of easements and includes development rights, subject to all applicable Talbot County zoning regulations. With vast working farmland and resort-style amenities, this rare gem truly combines luxury and sophistication with seclusion and tranquility. The 12,000+ sq. ft. primary residence showcases the breathtaking stylings of acclaimed architect Peter Jay Zweig and exempli

$13,750,000

5 beds8 baths13,228 sq ft

27772 Sharp Rd, Easton, MD 21601

Development rights • Pool pavilion • Gourmet kitchen

(410) 673-3344

ABOUT THIS HOME
Luxury Home for sale in 21658, MD:
Classic Colonial Overlooking the Golf Course in Prospect Bay. BRAND NEW ROOF! Welcome to this beautifully maintained brick-front Colonial, perfectly positioned with picturesque golf course views in the sought-after Prospect Bay community. Filled with natural light from oversized windows, the open floor plan offers the perfect balance of comfortable everyday living and elegant spaces for entertaining. The home features four spacious bedrooms upstairs, plus a first-floor office or optional fifth bedroom, making it ideal for guests, multi-generational living, or working from home. Hardwood floors, two fireplaces, a formal dining room, and generously sized living spaces create timeless appeal t

$1,199,000

5 beds3 baths3,757 sq ft

4 Prospect Bay Dr W, Grasonville, MD 21638

First floor office • Covered awning • Heated swimming pool

(410) 263-8686

OPEN SAT, 11AM TO 1PMFLOOR PLAN

ABOUT THIS HOME
Luxury Home for sale in 21658, MD:
Come experience the relaxed, resort-style lifestyle of Prospect Bay, one of the Eastern Shore’s most desirable golf course communities. Spend your days enjoying the 18-hole championship golf course, relaxing by the community pool, playing tennis or pickleball, or heading out on the water. Prospect Bay offers a community boat ramp and marina with access to navigable waters leading to Eastern Bay, putting St. Michaels, Kent Narrows, Annapolis, and other Chesapeake Bay destinations within reach by boat. Meet friends for dinner or drinks at the clubhouse restaurant, visit the pro shop, or take part in the community’s active social calendar. Ideally located on Maryland’s Easter

$899,000

5 beds2.5 baths3,073 sq ft

14 Fairway Is, Grasonville, MD 21638

Bright kitchen • One acre lot • Sunny morning room

(410) 643-2244

Property at 13446 Blackberry Ln, Wye Mills, MD 21679, 4 beds, 4.5 baths

$965,000

4 beds4.5 baths6,043 sq ft

13446 Blackberry Ln, Wye Mills, MD 21679

(410) 224-2200

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

$1,299,000

5 beds3.5 baths3,500 sq ft

952 Chester River Dr, Grasonville, MD 21638

(703) 378-8810

Property at 11470 Wye Heights Rd, Easton, MD 21601, 11 beds, 10 baths

$3,495,000

11 beds10 baths10,533 sq ft

11470 Wye Heights Rd, Easton, MD 21601

(410) 822-6665

Property at Vfw Ave, Grasonville, MD 21638

$1,400,000

Land4.41 acres (lot)

Vfw Ave, Grasonville, MD 21638

(410) 643-2244

Luxury Homes for Sale in 21658

There are currently 10 luxury homes for sale in 21658 at a median listing price of $650K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 21658 stay on the market for 74 days and receive 1 offers. This map is refreshed with the newest listings in 21658 every 15 minutes.

In the past month, 2 homes have been sold in 21658. In addition to houses in 21658, there were also 0 condos, 1 townhouse, and 0 multi-family units for sale in 21658 last month. Find your dream home in 21658 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 21658 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 21658. If you're looking to sell your home in the 21658 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 21658 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for 21658, MD

Nearby Zip Codes

Cities

Nearby Zip Codes with Luxury Homes

Nearby Cities with Luxury Homes

More to explore in 21658, MD

How to buy a house in 21658, MD

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Buy the right home at the right price near 21658 with a local Redfin real estate agent.

Popular Markets in Maryland

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.