2025 Water Front Book

life on the WATER

Across The Chesapeake Bay Region

Find a place to drop your anchor

Experience endless water views, private docks, and the unmatched tranquility that only waterfront living can offer. We invite you to explore a curated collection of waterfront homes across Maryland’s Chesapeake Bay region — and discover our full inventory at sothebysrealty.com/ttrsir

1864

Milvale Road

ANNAPOLIS, MARYLAND

A Rare Opportunity on Milvale Road and Mill Creek. This exceptional waterfront property, crafted by renowned builder Lynbrook Homes and thoughtfully designed by architect Vince Green, offers a rare blend of luxury and serenity. The open-concept floor plan is designed to maximize the sweeping, panoramic views of Mill Creek, with western exposure providing breathtaking sunsets year-round. Spanning three beautifully finished levels, the home is connected by an elevator and showcases designer touches throughout. The gourmet kitchen is a chef’s dream—outfitted with top-tier appliances and ideal for both grand entertaining and intimate gatherings. The luxurious primary suite is a private retreat, featuring a spa-like bath with a soaking tub, oversized shower, and dual walk-in closets. Outside, the 250foot shoreline is secured by a new seawall (2021), while the private pier is a true highlight for boaters: four slips, a 12,000-pound boat lift, three jet ski lifts, and an impressive 8 feet of mean low water depth.

Offered at $5,950,000 Glenn Sutton 410.507.4370, gsutton@ttrsir.com

1900 Carrollton Road

ANNAPOLIS, MARYLAND

Rare opportunity for a true legacy property on the Severn River. Built by Pilli Custom Homes, this home is a masterpiece of craftsmanship. Wake up every morning to the everchanging scenery out your windows, step out onto your private balcony with a freshly brewed coffee from your in-room coffee bar, feeling the gentle river breeze as you watch sailboats drift by. Make your way down via the elevator or stairs to the heart of the home – a gourmet kitchen designed for both function and beauty. A commercial-grade stove, oversized island, high end appliances and butler’s pantry set the stage for memorable meals, whether it’s a casual breakfast in the sunlit dining area or a feast prepared for guests. The open floor plan ensures that no moment is spent away from the home’s most stunning feature – its endless panoramic water views. At 1900 Carrollton Road, every day feels like a dream –a life immersed in luxury, comfort, and the beauty of the Severn River.

Offered at $8,995,000

Brad Kappel Team 410.279.9476, bkappel@ttrsir.com

17 Revell Street

ANNAPOLIS, MARYLAND

Welcome to the ultimate Spa Creek waterfront oasis. Enjoy living in the heart of historic Downtown Annapolis with walkability to everything the area has to offer including just steps to restaurants and bars, annual parades/events, Annapolis Yacht club, St. Mary’s school, and water taxi pick up location. Additionally, the property boasts the only gated waterfront residence in Historic Annapolis. Savor the sweeping south-facing views! This exceptional property offers an intimate connection to the vibrant life on Spa Creek, where you can take in the tantalizing sunsets from the elevated vantage point and front row seats to the Blue Angels show, Christmas lights parade, and fireworks. Boasting 260 feet of prime waterfrontage, it features a commercial-grade private pier designed to accommodate a 70-foot yacht, two 40-foot vessels, and provides a convenient boat lift and floating dock for launching additional water toys. This exceptional waterfront residence offers an unparalleled blend of refined luxury and architectural grandeur.

SOLD $11,250,000

Brad Kappel Team 410.279.9476, bkappel@ttrsir.com

East Lake Drive

ANNAPOLIS, MARYLAND

Sophisticated yet relaxed, this Bay Ridge home offers three bedrooms, three-and-a-half bathrooms, and a seamless blend of elegance and coastal living. Walls of glass in the primary suite capture sweeping views of Lake Ogleton, while the chef’s kitchen and open living spaces make entertaining effortless. Enjoy the saltwater pool and spa overlooking the water, or head to your deeded pier for direct access. A fully functional apartment above the detached garage provides the perfect guest house, office, or in-law suite. Truly a staycation destination and an ideal lock-and-leave residence.

Offered at $2,775,000

Betsy Dunigan 443.994.1239, bdunigan@ttrsir.com

2 River Drive

ANNAPOLIS, MARYLAND

Welcome to 2 River Drive, where sweeping views of the Severn River and Chesapeake Bay frame every moment of life. Tucked into the beloved Bay Ridge community, this classic home has been exquisitely renovated to blend timeless character with thoughtful updates. The heart of the home is its breezy three-season porch, perfect for entertaining, lounging, or simply watching the boats drift by. A chef’s kitchen with marble counters and top-of-the-line appliances connects seamlessly to the gardens, while flexible main-level rooms offer space for work or guests. Outside, mature landscaping, stone terraces, and a screened gazebo invite long summer evenings of crabs and laughter. With a guest suite over the garage, geothermal heating, and endless storage, every detail has been carefully considered. Beyond the property, Bay Ridge offers private beaches, marina, waterfront pool, and lively community traditions that make this one of Annapolis’ most cherished neighborhoods.

Exclusive Private Listing – Price Upon Request Alex Tower Sears 443.254.5661, atsears@ttrsir.com

Island Club Road

TILGHMAN ISLAND, MARYLAND

Welcome to waterfront living at its finest on picturesque Tilghman Island. This beautifully maintained 3,040 square foot Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor living. Enjoy your morning coffee while watching boats drift by, or relax in the evening with views that will take your breath away. The home is located in a sought-after waterfront community offering fantastic amenities including a clubhouse, pool, and marina—perfect for boating, entertaining, and leisure. Whether you’re looking for a peaceful fulltime residence or a weekend retreat, this home checks all the boxes. Just bring your boat and your dreams.

Offered at $1,200,000

Cheri Bruce-Phipps 443.994.2164, cbrucephipps@ttrsir.com

7090 Cooper Point Road

BOZMAN, MARYLAND

This extraordinary 6.92-acre estate on Leadenham Creek blends timeless craftsmanship with the natural beauty of Maryland’s Eastern Shore. Designed by Alan Meyers, built by Ilex Construction, and styled by Skip Sroka, the 10,000+ square foot residence showcases refined architecture and exquisite detail throughout. A cedar shake roof with copper accents crowns the custom brick exterior, while mahogany doors with leaded glass open to a foyer framing breathtaking water views. Inside, riff-sawn red oak floors flow through expansive living areas enhanced by vaulted ceilings, curated lighting, and five handcrafted fireplaces. The gourmet kitchen features top-tier appliances, a large island, sitting area with fireplace, and access to a screened porch with octagonal ceiling. The private primary wing offers serene water views, dual closets, a sitting area, and a spa-inspired bath, while additional guest suites are located in separate wings. Outdoor living is elevated with a waterside patio, pool house, heated spa, and over 1,000 feet of riprapped shoreline with a 210-foot dock offering 7’ MLW, two slips, and a floating dock.

Offered at $7,500,000

Laura Carney 410.310.3307, lcarney@ttrsir.com

EASTON, MARYLAND

Laura Carney 410.310.3307, lcarney@ttrsir.com 27772 Sharp Road

Stock Range Farm is an exceptional 350-acre estate in Talbot County that combines natural beauty with luxury living. Designed by architect Peter Jay Zweig and constructed by Ilex Construction, this 12,000+ square foot ‘Farm-Modern’ residence showcases exquisite craftsmanship and architectural details throughout. With stunning panoramic views of Pickering Creek, beautiful vineyards, pastures, and crop fields, the home’s floor-to-ceiling glass walls fill every room with natural light. Thoughtfully curated for comfort and privacy, the residence features spacious living areas, and separate wings for owners and guests, all adorned with luxurious details. The property boasts 3,300+ feet of protected shoreline, a private pier complete with a lift and floating dock, 4’ MLW, and quick access to the Wye River and Chesapeake Bay. Additional amenities include a resort-style heated infinity pool with waterfall, an elaborate pool pavilion, koi pond, and a tennis/ pickleball court, all set within extensive landscaping. Equestrian enthusiasts will appreciate the 9-stall barn, while the estate also features a 4-bedroom guesthouse, 6-acre stocked pond, a fully equipped greenhouse, and both equipment and hay barns.

Offered at $13,750,000

26025 Bachelors Harbor Drive

OXFORD, MARYLAND

Discover unparalleled luxury and breathtaking waterfront living at this stunning estate, perfectly situated at the confluence of the Tred Avon and Choptank rivers, leading to the majestic Chesapeake Bay. This exclusive property boasts spectacular sunset views and offers a rare opportunity for discerning buyers to own a piece of paradise. Enjoy panoramic water views and serene sunsets from this elevated site, offering privacy and tranquility. For yacht owners, the property includes a 65’ deeded boat slip with 8 ft MLW in protected Bachelor Harbor, complete with a floating dock, offering seamless access for your yacht. The private driveway adjacent to the boat slip ensures effortless arrivals and departures. Experience the epitome of waterfront luxury and make this extraordinary estate your new home.

SOLD $3,800,000

Larry Brennan 410.443.3659, lbrennan@ttrsir.com

Kent Point Road

STEVENSVILLE, MARYLAND

Elegant waterfront home resting on the banks of the Chesapeake Bay nestled in a bucolic setting with stunning sunset views just minutes from the Bay Bridge. Experience a rare blend of elegance, privacy, and panoramic Chesapeake Bay views from this extraordinary 19-acre waterfront estate. This stunning residence is designed for both refined living and effortless entertaining, with a thoughtfully curated layout and resort-style amenities throughout. Step outside into your personal paradise. The resort-style pool area is accented by exquisite hardscaping, offering multiple areas for lounging, entertaining, and dining al fresco. A sunken fire pit sets the stage for magical evenings under the stars. The separate pool house is a fully equipped guest retreat with a kitchen, living area, bedroom, and full bath. The private pier is equipped with a boat lift, multiple slips and is a quick 15-mile cruise by boat to St. Michael’s or the Annapolis harbor.

Offered at $5,995,000

Brad Kappel Team 410.279.9476, bkappel@ttrsir.com

ANNAPOLIS, MARYLAND

Welcome to this slick and sleek coastal contemporary designed by renowned architect Chip Bohl and built by Gate One Builders. The 5,500 square foot home (renovated in 2017) features six bedrooms (five ensuites), with unmatched views of the “sweet spot” of the Severn River. Watch the magical and mesmerizing incessant theatre of watercraft and wildlife on the River and Chesapeake Bay from the massive great room with 60’ long wall of 10 ½’ high windows/ sliders, the private, expansive bluestone and concrete patio or within one of several more intimate spaces, all with magnificent and expansive waterfront views. Other features include: two primary suites (one on each level), 5” cherry plank floors, custom lightwell staircases with modern cable handrail system, oversized windows and generous closets in every room.

Offered at $3,850,000

Marcia Zercoe 410.703.3008, mzercoe@ttrsir.com

WEST RIVER, MARYLAND

Completely reimagined in a 2022 down-to-the-studs renovation, this remarkable waterfront home seamlessly blends modern luxury with effortless coastal living. Inside, you’ll find a chef’s kitchen worthy of culinary dreams, a serene owner’s suite with spa-like features, including heated floors, an oversized shower, and soaking tub, and bespoke details throughout. Here, life slows down. Just past horse farms and rolling pastures, the home is perfectly set on the exclusive Chalk Point peninsula, offering an idyllic retreat with breathtaking water views. Complete with a brand-new deep-water pier with 6 MLW ft of deep water, 15k lb. boat lift, and a floating dock on protected waters and quick access to the West River & the Bay, this is a boater’s paradise. Evenings bring postcard-worthy sunsets over your dock, and mornings start with peaceful sunrise strolls. This home checks every box inside and out, from boating, entertaining, or simply unwinding in your Adirondack chair on the shoreline.

SOLD $1,495,000

Michele Deckman 410.353.3703, mdeckman@ttrsir.com

1634

Ridout Road

ANNAPOLIS, MARYLAND

Welcome to Amberley, one of Annapolis’ s most sought-after-water privileged communities along Whitehall and Ridout Creeks. This thoughtfully redesigned four-bedroom, two-anda-half-bath home-crafted by a local architect-blends timeless style with modern coastal living. The light-filled interior features an open floor plan, soaring ceilings, and hardwood floors throughout. The fresh coastal kitchen is the heart of the home, designed for both entertaining and everyday comfort. Residents of Amberley enjoy access to three private community piers, perfect for boating, paddleboarding, or simply soaking in the waterfront lifestyle. All this, just minutes to downtown Annapolis, marinas, and Blue Ribbon Schools.

Offered at $989,000

Betsy Dunigan 443.994.1239, bdunigan@ttrsir.com Gwin Hunt 410.353.4817, ghunt@ttrsir.com

6670 Tilghman Island Road

SHERWOOD, MARYLAND

Waterfront home situated on Back Creek in Sherwood, offering direct access to the Chesapeake Bay and Choptank Rivers. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed lighting. The kitchen is equipped with stainless steel appliances, a built-in pantry, and granite countertops. The open floor plan incorporates a gas fireplace and a formal dining room. The primary suite has a walk-in shower, soaking tub, and walk-in closet. An attached three-car garage provides additional space with an upstairs bonus game/theatre room. The backyard is built for fun with a swimming pool, an outdoor kitchen with bar area, gas fire features, a hot tub, and a pool house for storage.

Offered at $1,299,000

Larry Brennan 410.443.3659, lbrennan@ttrsir.com

11977

Billy’s Point Lane

EASTON, MARYLAND

Henry’s Retreat is an extraordinary 37-acre waterfront estate overlooking Quarter Cove off the Wye River, offering over 2,700 feet of shoreline, ultimate privacy, and breathtaking sunsets. Built in 2016, the 8,835 square foot main residence was designed for luxurious living and seamless entertaining, with five bedrooms, six full baths, and two half baths. The main-level primary suite enjoys sweeping water views, an expansive dressing room, and a spa-inspired bath with soaking tub, walk-in glass shower, and private laundry. A chef’s kitchen with Thermador appliances, granite center island, and barrel-vaulted ceiling is the heart of the home, opening to a sunroom wrapped in 180-degree windows and a great room with soaring ceilings and stone fireplace. The second level provides four guest bedrooms, a fitness room, and a conservatory, while the finished lower level is complete with a theater room, billiards area, wet bar, and full bath. Outdoor amenities include a saltwater pool, hot tub, pavilion with outdoor kitchen, and a 125’ private pier with three slips, three lifts, and 7’–8’ MLW. For equestrians, a five-stall barn offers private paddocks, climate-controlled tack room, heated wash stall, and regulation dressage ring with interlocking pastures.

Offered at $6,450,000

Laura Carney 410.310.3307, lcarney@ttrsir.com

5440 Ferry Neck Road

ROYAL OAK, MARYLAND

Drake’s Landing is a beautifully renovated 20-acre waterfront estate on Irish Creek, offering 4,602 square feet of thoughtfully designed living space and sweeping westerly views. Completely updated in 2021, the home combines casual elegance with modern comfort, beginning with expansive water views that greet you upon entry. The main level includes a guest suite, cozy family room, and a gracious living room highlighted by a large brick hearth and woodburning fireplace. At its center, the gourmet kitchen features upgraded appliances, a breakfast island, and adjoining dining space, with a second kitchen nearby for effortless indooroutdoor entertaining. A formal dining room and a waterside sunroom complete the main living areas, while upstairs, two spacious primary suites anchor opposite ends of the home, joined by two guest bedrooms and additional baths. Outdoor living is elevated with a new dock offering two slips, a stunning waterside pool, firepit, barrel sauna, and screened porch perfect for crab feasts and sunset dining.

Offered at $3,250,000

Laura Carney 410.310.3307, lcarney@ttrsir.com

The Penthouse at South Annapolis Yacht Centre

ANNAPOLIS, MARYLAND

This is the perfect property for those who seek a serene backdrop to an extraordinary life. With exclusivity and serenity, the Penthouse with 2 guest suites at South Annapolis Yacht Centre Residences combines premier waterfront living with spectacular design that is both timeless and modern. Enjoy breathtaking views of Spa Creek, the Annapolis Harbor and the historic skyline of downtown Annapolis from almost every room and the multiple exterior decks. This property encompasses the stunning Penthouse condo with 3 bedrooms, 2.5 baths and includes 2 guest suites with full baths on the ground level. The South Annapolis Yacht Centre provides an elegant boutique lifestyle in a marina village setting comprised of 11 Residences and a full-service marina. SAYC is part of the rich Annapolis maritime heritage with 74 new deep water slips (12ft MLW+) to accommodate boats up to 140ft, extensive electrical supply options, waterfront boardwalk, travel lift & direct access to essential marine services.

Offered at $7,950,000

Brad Kappel Team 410.279.9476, bkappel@ttrsir.com

413

West Joyce Lane

ANNAPOLIS, MARYLAND

Welcome to this time;ess four-bedroom residence, tucked away on one of the most beautiful waterfront lanes in Anne Arundel County. Set on 2.3 acres framed by mature trees, this property offers privacy, serenity, and an unmatched sense of place. The backyard is a true oasis featuring a sparkling pool, outdoor shower, koi pond, and expansive entertaining areas – perfect for summer gatherings or quiet evenings at home. Across the street, an additional deeded 0.6 acre lot provides 15 feet of waterfront on The Severn River with a dock and seating area, offering a front-row seat to the Chesapeake lifestyle. Classic in design and surrounded by top-rated schools, this home blends charm, comfort and outdoor living in one of the county’s most sought-after locations. A true Chesapeake retreat.

Offered at $1,800,000

Betsy Dunigan 443.994.1239, bdunigan@ttrsir.com

820 Mill Creek Road

ARNOLD, MARYLAND

Introducing 820 Mill Creek Road in Magothy Shores, a beautifully updated waterfront cottage blending modern finishes with original character. Just 7 doors down from The Point Crab House and Grill, you can enjoy happy hour with the neighbors or linger over steamed crabs and craft cocktails with your family that just pulled in by boat. The home was originally built by a brick mason as a sturdy summer bungalow and has been added onto over the years with a second story, finished lower level and detached one-car garage with guest quarters above. Inside, renovations include a fully rebuilt kitchen (2016), luxurious primary suite with water views and spa bath (2017), and updated main floor bath (2021). Outdoors, enjoy landscaped gardens, a sunroom opening to a waterside terrace, and a gentle slope to the private pier and kayak launch.

Exclusive Private Listing – Offered at $1,699,000

Michele Deckman 410.353.3703, mdeckman@ttrsir.com

Corsica Point Lane

CENTREVILLE, MARYLAND

A true legacy property, Corsica Point Lane is an offering unlike any other. Situated on the Corsica River on Maryland’s Eastern Shore, the estate boasts 1,200 feet of shoreline, deep water pier with boat lift and spans 14.7 acres. It serves as a serene contrast to urban living, with open expanses, permeated only by the gentle sounds of the river and surrounding wildlife. A long, meandering driveway winds through the open field past the barn and guest house to the stately brick home and pool house. Upon entry the attention to detail, beautiful woodwork and impressive two-story living room is only surpassed by the water views framed by the oversized windows and doors leading out to the brick patio. The patio provides the perfect place to relax and soak in the surroundings or head over to the pool house and pool for a refreshing dip. The pool house boasts a full kitchen, half bath and covered loggia to escape the sun. The ultimate setup for easy entertaining and enjoying the waterfront lifestyle.

Offered at $4,300,000

Joe Bray 410.936.8904, jbray@ttrsir.com 210

Holland Cliffs

HUNTINGTOWN, MARYLAND

Experience waterfront living on the Patuxent River with this exceptional brick-front home featuring 7 bedrooms, 4 full bathrooms, and a 2-bedroom handicap-accessible guest apartment with full kitchen and private access. The residence offers an elevator serving all three levels, a pool with composite decking, oversized 3-car garage, and multiple sheds. Enjoy the private dock and pier with boat lifts, deep-water access, and a paved road to the shoreline. Additional highlights include an all-seasons room, wood-burning fireplace, new roof (2022), new hot water heater (2023), a new septic system with nitrogen removal (2023), new well (2024), new pool liner (2024), and 10,000 pound boat lift and jet ski lift. This property combines modern updates, versatile spaces, and panoramic river views in a private setting convenient to major routes.

Exclusive Private Listing – Offered at $1,600,000

Brooke-Austin McAdam 603.305.0967, Brooke@AustinTeam.com Kathi Austin 410.458.8758, Kathi@AustinTeam.com

948 Melvin Road

ANNAPOLIS, MARYLAND

A winding, tree-canopied drive leads to Silver Maple Manor, a breathtaking waterfront and equestrian estate nestled on nearly eight acres along Little Aberdeen Creek. Designed by the renowned Scarlett Breeding and built with masterful craftsmanship, this European-inspired retreat feels as if it has stood for centuries, its mature landscaping and thoughtful details evoking the grandeur of a bygone era. With five bedrooms, six full bathrooms and two half bathrooms, this home is a masterpiece of custom millwork, rough-sawn oak flooring, and exquisite stonework. Though it feels like a secluded retreat, Silver Maple Manor is just minutes from Historic Annapolis and an easy commute to Washington, D.C., Baltimore, and major airports.

SOLD $10,250,000

Seller represented by Brad Kappel, 410.279.9476, bkappel@ttrsir.com

Buyer represented by Lydia Travelstead, 410.280.5600, ltravelstead@ttrsir.com and Haley Murnane, 410.280.5600, hmurnane@ttrsir.com

ANNAPOLIS, MARYLAND

Wonderful opportunity to create your own waterfront oasis in the heart of Bay Ridge, Annapolis. Enjoy breathtaking views of the Bay Bridge and direct access to one of the area’s most spectacular private beaches.

Nestled in a vibrant coastal community known for its sailing, beach walks, and friendly charm, this property offers a rare blend of lifestyle, location, and flexibility. The highly sought-after Bay Ridge community in Annapolis offers a rare blend of resort-style amenities and vibrant coastal charm. Residents enjoy a scenic community pool and clubhouse overlooking the sparkling waters of the Chesapeake Bay, as well as private community beaches on both the Bay and the River. Boating enthusiasts will appreciate the community marina, complete with a newly renovated clubhouse. Located just minutes from Historic Downtown Annapolis, Eastport, and all major commuter routes, Bay Ridge offers the perfect balance of small-town charm with big-city access.

Offered at $2,300,000

Alex Tower Sears 443.254.5661, atsears@ttrsir.com  Salley Widmayer 202.215.6174, swidmayer@ttrsir.com

200

Metzdorf Lane

QUEENSTOWN, MARYLAND

Set along Queenstown Creek with direct access to the Chester River, 200 Metzdorf is a rare Eastern Shore estate offering 56 feet of private waterfront and sweeping golf course views. Built in 1894 and thoughtfully updated, the home blends historic character with modern comforts, featuring a remodeled kitchen, enhanced baths, and recent system upgrades. A private pier with deep-water slips, two lifts, and a boat ramp, plus outdoor spaces including a deck, pavilion, and gazebo, embrace the Chesapeake lifestyle. With immediate access to preserved lands, world-class marinas, and easy connections to Annapolis, D.C., and Baltimore, this property represents a truly scarce waterfront opportunity.

Offered at $959,900

Erica Baker 410.919.7019, ebaker@ttrsir.com

STEVENSVILLE, MARYLAND

Bridgeview; a prestigious legacy property in a league of its own. Prominently displayed on the banks of the Bay, and aptly named to reflect the unobstructed views of the Chesapeake Bay Bridge, this 18 acre estate is a true masterpiece inside and out. The attention to detail, commercial grade construction, interior design, craftsmanship and quality of materials are unparalleled. The grounds feature spectacular 180 degree Bay views, heated pool/spa with fountains, outdoor kitchen and pavilion, professional landscaping, sandy beach and private pier with boat and jet ski lifts, creating a peaceful haven filled with sculpted gardens, open expanses and the tranquil sounds of waterfowl and wildlife.

Offered at $14,950,000 Brad Kappel Team 410.279.9476, bkappel@ttrsir.com

5135

ROCK HALL, MARYLAND

A true sportsman’s paradise and a family compound, this impressive 212 +/-acre farm offers breathtaking water views and unparalleled outdoor recreation. The solidly built, colonial style home is designed to capture the beauty of Davis Creek from nearly every room. The kitchen and dining area are perfectly positioned for waterfront entertaining, seamlessly flowing into the family room with gas fireplace and the sunroom. Expansive decks overlook the creek and the entrance to Lankford Bay. For more intimate gatherings, a formal dining room provides the perfect setting for cozy celebrations. Boating enthusiasts will appreciate the multi-slip deep-water dock with 5 feet MLW, a 16,000 lb. boat lift and a jet ski lift. The property consists of three parcels. The main parcel is over 72 acres and includes the residence, barn, and outbuildings. There is an 82+ acre buildable parcel featuring a dock and a cleared buildable site with water views. The third buildable parcel is nearly 58-acres with established farmland and prime hunting grounds. The two additional parcels already have paid public sewer hook ups. Approximately 88 acres of woods. The farm is well-equipped for agriculture (111 tillable acres), premier hunting, and endless recreational opportunities.

Offered at $5,900,000

Courtney Chipouras 410.200.1224, cchipouras@ttrsir.com

6780

Cookes Hope Road

EASTON, MARYLAND

Nestled along the Oxford Road corridor, this custom one-level waterfront home blends elegance and comfort with sweeping water views. Designed by Pam Gardner, the open floor plan features a vaulted family room with skylights, wood floors, and a striking catwalk. The waterside primary suite offers a fireplace, steam shower, soaking tub, and walk-in closet, while a separate guest wing and detached one-bedroom apartment provide privacy and comfort. Enjoy the spacious kitchen, private den with fireplace, and light-filled cupola room. Outdoor living shines with a screened porch and waterside deck, plus a leased boat slip available in 2025.

Offered at $1,695,000

Kathy Christensen 410.924.4814, kchristensen@ttrsir.com

ANNAPOLIS, MARYLAND

Welcome to your luxury waterfront sanctuary on the Severn River, located in the highly coveted Downs on the Severn community of Annapolis. This extraordinary estate offers unmatched amenities including a private sport court, heated saltwater pool, and private pier with a tram to easily transport you and your guests to the water’s edge for unforgettable days on the Bay. Inside, the craftsmanship is unparalleled and the curated finishes reflect that no expense was spared to create a home of distinction. The deep water private pier features multiple slips and 40,000lb boat lift; creating an effortless and fun atmosphere while cruising down the Severn River to the Chesapeake Bay and beyond. Experience a life of privacy, resort-style amenities, and timeless beauty in this one-of-a-kind waterfront masterpiece.

SOLD $6,700,000

Brad Kappel Team 410.279.9476, bkappel@ttrsir.com

Piney Neck Road

ROCK HALL, MARYLAND

Discover Kellys Bank, a 31.99-acre waterfront estate with 4,400+ feet of shoreline on Langford Bay and a protected cove. Elevated above the flood zone, this fully renovated home offers 5 bedrooms, 3.5 bathrooms, and sweeping water views from nearly every room. The primary suite includes a luxurious bath, walk-in closet, sitting area, and gas fireplace. A chef’s kitchen with oversized island and pantry anchors the living and dining areas, where original hardwoods, a wood-burning fireplace, and paneled walls add warmth. A sunroom showcases panoramic bay and river views, while four guest bedrooms share Jack and Jill baths. The lower level offers a gas fireplace, wet bar, and plumbing for an additional half bath. Beyond the home: 16 tillable acres, pond, multi-slip dock, abundant wildlife, and detached garage with workshop.

SOLD $3,350,000

Courtney Chipouras 410.200.1224, cchipouras@ttrsir.com

1 Shipwright Harbor

ANNAPOLIS,

MARYLAND

Stately French Villa on Spa Creek in downtown Annapolis. This jewel box of a home was designed and built by renowned local architect as the culmination of an award winning career. The unsurpassed attention to architectural details, exquisitely curated finishes and breathtaking views of Spa Creek places this trophy home in a league of its own. Tucked away at the end of a quiet street in a premier residential enclave on the banks of Spa creek, this 3 bedroom 3.5 bathroom is the perfect weekend getaway or forever home. Relax every morning and evening from the private balcony while enjoying the panoramic views of Spa Creek, Annapolis Harbor, and Eastport. The 2 deep water piers with 9ft MLW can accommodate boats of all sizes and the location provides quick access from Spa Creek out to the Severn River, Chesapeake Bay and beyond. Walkable to everything Annapolis has to offer this truly unique property offers the complete package: convenience, security, beauty and comfort.

Offered at $5,898,000

Brad Kappel Team 410.279.9476, bkappel@ttrsir.com

Stillwater Road

GIBSON ISLAND, MARYLAND

An extraordinary opportunity awaits on beautiful Gibson Island. Designed for both intimate living and large gatherings, this spacious residence includes separate guest quarters that provide privacy and comfort for all. Light-filled living and dining rooms flow seamlessly, anchored by a wood-burning fireplace, while the open kitchen and family room connect effortlessly to a private patio, perfect for outdoor dining, lounging, and entertaining. The updated main-level primary suite offers water views and convenient access from the carport, while additional features include a twocar garage, greenhouse, and generous storage, all connected by a covered walkway. Surrounded by a serene Japanese garden, this property offers countless spots to relax and recharge. A rare chance to experience the best of Gibson Island living.

Offered at $2,295,000

Alex Tower Sears 443.254.5661, atsears@ttrsir.com

EDGEWATER, MARYLAND

Nestled along serene Cadle Creek in Edgewater, 1011 Skiff Cove Rd is a rare waterfront estate with over 135 feet of shoreline, a private pier, and two boat slips. Originally built in the 1800s and thoughtfully renovated in 2016–2017, the home preserves historic character while offering modern comforts, including three bedrooms, two baths, an upgraded kitchen, hardwood floors, and custom details throughout. Set on more than half an acre with sweeping water views, spacious outdoor living areas, and an oversized two-car garage, this property combines legacy, elegance, and the Chesapeake lifestyle just minutes from Annapolis.

SOLD $1,275,000

Erica Baker 410.919.7019, ebaker@ttrsir.com

STEVENSVILLE, MARYLAND

Welcome to Sunset Wharf, an exclusive 28 unit duplex development nestled in the serene Bay Bridge Marina. Embrace waterside living at its finest with stunning views, modern amenities, and the charm of a close-knit community. Each duplex is meticulously designed to offer spacious, open-concept layouts that blend modern elegance with everyday comfort. Enjoy breathtaking views of the Chesapeake Bay through expansive windows that fill your home with natural light. High-end finishes, gourmet kitchens, and luxurious master suites create an ambiance of sophistication and tranquility.

Starting at $2,350,000 – explore sunset-wharf.com

Brad Kappel Team 410.279.9476, bkappel@ttrsir.com

ST. MICHAELS, MARYLAND

This exceptional four-bedroom, three-bath residence boasts 3,300 square feet of meticulously crafted interiors, featuring a gourmet kitchen appointed with a Wolf six-burner range and SubZero refrigeration—perfect for culinary enthusiasts and entertaining on a grand scale. Enjoy a newly constructed dock with water, electric, and a floating kayak launch. With 3+ feet MLW, it accommodates a range of boating pursuits. The property’s thoughtful layout provides two bedrooms and two baths on the main level for effortless living, with two additional bedrooms and a full bath upstairs—ideal for hosting guests or family retreats. Unwind in the evenings on the expansive screened porch while savoring panoramic sunset views over tranquil waters. Perfectly situated between the charming towns of Easton and St. Michaels, this move-in ready estate promises privacy, convenience, and a relaxed Eastern Shore lifestyle.

Contract Pending $1,825,000

Larry Brennan 410.443.3659, lbrennan@ttrsir.com

6970 Kim Lane

FRIENDSHIP, MARYLAND

Discover your exclusive bayfront haven with breathtaking, panoramic Chesapeake Bay views. The heart of this home is its grand sunroom, where a stunning wall of windows captures the bay’s beauty—perfect for daily living or entertaining. Indulge in the tranquil primary suite, a private sanctuary, and offer guests their own comfortable level with a dedicated living room and bath. Just steps from the Chesapeake Bay, enjoy deep-water marinas, a picturesque boardwalk, waterfront dining, and the vibrant “Bay Life” lifestyle. With seamless access to Washington, D.C., Annapolis, Northern Virginia, and nearby cities, this retreat blends serenity with connectivity.

Offered at $1,400,000

Gil Poudrier, Jr. 301.775.1439, gpoudrier@ttrsir.com

CHESTERTOWN, MARYLAND

A waterfront lifestyle like you’ve never experienced before. This mid-century modern home hangs cliffside over the Chesapeake Bay’s Fairlee Creek, the privacy & exclusivity makes you feel as if you’re floating on a boat. The 2-acre parcel includes a second residence, totaling five bedrooms. Enjoy a private beach & dock, with access to the marina, pool, golf course, restaurants, & beach bar at neighboring Safe Harbor Great Oak Landing.

SOLD $1,062,800

Liddy Campbell 410.708.5433, lcampbell@ttrsir.com

OXFORD, MARYLAND

This fully updated 3-bed, 2.5-bath farmhouse offers modern comfort and prime access to Oxford’s marinas, ferry and waterfront parks. Featuring new kitchen, baths, HVAC and custom finishes, plus inviting porches and offstreet parking, it’s the ideal lock-and-leave coastal getaway.

SOLD $695,000

Kathy Christensen 410.924.4814, kchristensen@ttrsir.com  700

EDGEWATER, MARYLAND

Amazing waterfront opportunity with panoramic views over Selby Bay—from the protected shoreline of South River Farms Park to the open waters of the Chesapeake. With 60 feet of water frontage, this property offers the chance to build your dream home and enjoy sunrises, sunsets, and endless Bay views.

Offered at $780,000

Alex Tower Sears 443.254.5661, atsears@ttrsir.com

2512 Lyon Drive

ANNAPOLIS, MARYLAND

Commanding panoramic views of the Chesapeake Bay, Bay Bridge, and Eastern Shore, this exceptional waterfront residence offers an unparalleled waterfront lifestyle. The regions finest team was assembled including Purple Cherry Architects and Gate One Builders to create a custom masterpiece of style, design and tranquility.

Offered at $3,875,000

Brad Kappel Team 410.279.9476, bkappel@ttrsir.com

ANNAPOLIS, MARYLAND

Two 18th-century homes, 40 and 38 Cornhill, sold together in the heart of Downtown Annapolis. Flawlessly renovated across four levels, featuring a chef’s kitchen with conservatory opening to a walled Savannah garden, elevator to a primary suite with fireplace, city-view decks, lower-level gym, and custom finishes throughout. Remarkable views of the State House, Navy Chapel, and Bay, plus downtown parking, just steps to City Dock.

SOLD $2,900,000

Alex Tower Sears 443.254.5661, atsears@ttrsir.com 38 &

QUEENSTOWN, MARYLAND

Experience waterfront living on the Wye River in this immaculate 3-bedroom, 2.5-bathroom rancher on 1.6 acres. Built in 2013 and fully renovated in 2020, the home blends modern luxury with coastal charm. The vaulted living room features a wood-burning fireplace, while the chef’s kitchen offers quartz counters, propane cooktop, double ovens, and an island for entertaining. A custom bar with beverage cooler and ice maker enhances the dining area. The sunroom, with cathedral shiplap ceilings and automated blinds, frames sweeping river views. The primary suite includes a walk-in closet and spa-like bath with heated floors. Two guest bedrooms share a stylish full bath, and the powder room also has heated floors. Additional highlights include designer lighting, finished garage/ office, walk-up attic, and conditioned crawlspace. Outdoor living shines with a patio, riverside fire pit, rip-rapped shoreline, shed, and private dock with boat lift and slip.

SOLD $1,500,000

Courtney Chipouras 410.200.1224, cchipouras@ttrsir.com

Drum Point

ST. MICHAELS, MARYLAND

Your own private resort in St Michael’s Maryland. This one has it all and then some. Dock with boat lift, swimming pool, tennis court, 4 to 5 bedrooms, beautiful baths, hardwood floors. Within the last five years the owners have put on a new roof and dormers, redone the kitchen, encapsulated the crawlspace, installed a boat lift, replaced the boiler and painted the exterior.

SOLD $1,840,000

Larry Brennan 410.443.3659, lbrennan@ttrsir.com

CAMBRIDGE, MARYLAND

Beautifully updated 4-bedroom, 2.5-bathroom waterfront home on nearly an acre along scenic Hurst Creek—just off the Choptank River. This 2,496 sqft retreat offers its own private dock plus access to a community boat ramp and dock. Located less than an hour to the beach and just 90 miles from D.C., this move-in ready home delivers the best of Eastern Shore living—whether full-time or as a weekend escape.

Offered at $614,999

Melissa Tippett 410.241.7409, mtippett@ttrsir.com

NANTICOKE, MARYLAND

Stunning Waterfront Victorian on the Nanticoke River aka Sarah E. Travers House c. 1890-1900 This beautifully updated Victorian estate sits on over an acre along the serene Nanticoke River, complete with a private sandy beach, in-ground pool, and panoramic water views all the way to the Chesapeake Bay.

SOLD $700,000

Melissa Tippett 410.241.7409, mtippett@ttrsir.com

6153

Long Point Road

NEAVITT, MARYLAND

This stunning waterfront retreat sits on over 5 acres just 15 minutes from St. Michaels and is designed with flexibility in mind--perfect for year-round living, hosting guests, or simply spreading out and enjoying the Eastern Shore lifestyle. The property includes both a main residence and a fully renovated guest wing, and each features a ground-floor primary suite. Outside, enjoy over 300 feet of pristine shoreline, a private dock with kayak and paddle board access via private ramp, a saltwater pool with an integrated jacuzzi, and wide-open water views. Thoughtful sustainable features include geothermal heating and cooling and a solar energy system.

SOLD $3,650,000

The 3rd highest sale ever in the Neavitt/Bozman area.

Joe Bray 410.936.8904, jbray@ttrsir.com

202 Mulberry Street

ST. MICHAELS, MARYLAND

Discover this charming historic home in the heart of St. Michaels, built circa 1890, where classic craftsmanship and timeless elegance come together. Starting with the expansive wrap-around porch, you can see this home is a traditional gem. Highlights of the home include 9ft. ceilings , hardwood floors throughout, and original architectural details that define the craftsmanship and charm.

SOLD $1,196,000

Monica Penwell 410.310.0225, mpenwell@ttrsir.com

Dobbins Island

PASADENA, MARYLAND

Discover a once in a lifetime opportunity to own a private island retreat in the heart of the Chesapeake Bay region. The Magothy River’s renowned Dobbins Island is a breathtaking 7.2 acre waterfront sanctuary, offering unmatched seclusion and stunning natural beauty. Accessible only by boat and just minutes from the mainland, this exclusive property is designed for those who seek a truly unique waterfront lifestyle. The newly constructed (2019), 4,000+ sq. ft. custom home features 3 bedrooms and 3 baths, complete with an elevator.

Offered at $1,980,000

Brad Kappel Team 410.279.9476, bkappel@ttrsir.com

Presquile Drive S

EASTON, MARYLAND

Imagine waking up to the sound of water gently wrestling against your shoreline, sunlight glistening across the River, and the day unfolding with endless possibilities - sailing, paddleboarding, or simply savoring the view from your porch. The Eastern Shore has always been a destination for those seeking balance: tranquility without isolation, charm without compromise, and luxury wrapped in natural beauty. This recently sold home embodied all of this - a private retreat with timeless architecture, sweeping waterfront views, and a space to gather with friends and family. The Eastern Shore is where neighbors gather on porches, crab feasts last long in to the evening, and weekends are spent on the water. It’s a reminder of what makes waterfront living here so coveted.

SOLD $1,250,000

Daphne Cawley 410.310.2373, dcawley@ttrsir.com

41710

Dos Santos Way

MECHANICSVILLE, MARYLAND

Discover an exquisite waterfront haven at The Estate on Dos Santos Way, nestled along the tranquil Patuxent River. This all-brick masterpiece, spanning 16,744 square feet, blends unparalleled luxury with serene seclusion, offering breathtaking water views and a private family retreat. Step into a grand foyer crowned by a 27-foot domed ceiling, a sweeping double staircase, and a dazzling Swarovski crystal chandelier. Refined details like ornate moldings and elegant columns define the home’s sophisticated charm. The main level showcases a lavish owner’s suite, a two-story great room with floor-to-ceiling windows, and a gourmet kitchen featuring premium appliances. A 9-foot elevator seamlessly connects all levels. Upstairs, two additional primary suites and four spacious bedrooms, each with en-suite baths, provide ample comfort. The lower level is an entertainer’s dream, boasting a custom movie theater, grand ballroom, game room, gym, and a cozy family room with a fireplace.

Outdoor amenities elevate the experience with a scenic water-view terrace, a 202-foot pier equipped with two boat slips, a boat lift, two jet ski lifts, and electric and freshwater hookups.

Exclusive Private Listing – Offered at $6,995,000

Gil Poudrier, Jr. 301.775.1439, gpoudrier@ttrsir.com

137 Tanners Point

STEVENSVILLE, MARYLAND

Welcome to this stunning 5-bedroom, 3.5-bathroom waterfront estate set perfectly on a spectacular point of land in the prestigious Cove Creek community. Offering 566 feet of pristine, protected waterfrontage where Tanner’s Creek meets Cove Creek--flowing directly into the Eastern Bay--this southern-facing residence captures breathtaking panoramic water views from nearly every room.

Offered at $2,995,000

Joe Bray 410.936.8904, jbray@ttrsir.com

2175 Cherry Tree Lane

ANNAPOLIS, MARYLAND

Exquisite Savannah Style custom-built home in sought after, amenities-rich, Fishing Creek Farm community in Annapolis. This non-riparian waterfront home is nestled between 2 bodies of water providing endless water views from almost every room of the house. Wake up early to watch the wildlife and the sunrise over Cherry Tree Cove from the rear screened porch or enjoy peaceful water views and sunsets over Duvall Creek from the relaxing front porch.

Offered at $2,675,000

Brad Kappel Team 410.279.9476, bkappel@ttrsir.com

14 President Point Drive – Unit

ANNAPOLIS, MARYLAND

Commanding one of Annapolis’ most coveted waterfront addresses, 14 President Point Drive #A1 offers a rare blend of sophistication and exclusivity. Enjoy refined interiors, a chef’s kitchen, and private outdoor living within a community featuring a marina, waterfront pool, and tennis courts, all just moments from downtown Annapolis and the Chesapeake Bay. An extraordinary opportunity to secure a premier residence in Maryland’s capital of sailing, history, and prestige.

Under Contract $749,900

Erica Baker 410.919.7019, ebaker@ttrsir.com

33488 Tuckahoe River Road

EASTON, MARYLAND

Nestled on over two scenic acres along the Tuckahoe River, Twin Peaks is a stunning mid-century modern home designed to capture breathtaking water views from every angle. Thoughtfully renovated, this 4,800+ sq. ft. retreat blends timeless elegance with modern luxury. Step outside to enjoy private dock access with electric service, perfect for boating, fishing, or just unwinding by the water.

SOLD $950,000

Melissa Tippett 410.241.7409, mtippett@ttrsir.com

7930 Church Neck

ST. MICHAELS, MARYLAND

Welcome to “Point of View” offering the perfect blend of elegance and tranquility in this stunning coastal style home nestled on 4+/- acres with 220 feet of riprapped shoreline along picturesque Broad Creek. With its breathtaking southwesterly views and design to capture the essence of serene waterfront living, this property is a rare gem just minutes to the historic waterfront town of St. Michaels.

SOLD $1,833,000

Monica Penwell 410.310.0225, mpenwell@ttrsir.com

48 Poplar Point

EDGEWATER, MARYLAND

Nestled in the heart of Poplar Point on a serene lot with 350 feet of shoreline, this beautifully updated waterfront home offers panoramic views, exceptional privacy, and a lifestyle designed around comfort, nature, and time on the water. Nearly every room faces the water, with full-width views enjoyed from the expansive deck, pool, and light-filled interior spaces.

Offered at $3,750,000

Brad Kappel Team 410.279.9476, bkappel@ttrsir.com

5594 Langford Bay Road

CHESTERTOWN, MARYLAND

Experience the perfect blend of vintage charm and modern updates with this beautifully maintained 1950s craftsman, peacefully tucked along the scenic Chester River. Set on a quiet, tree-lined stretch of the river yet just minutes from the historic shops, restaurants, and cultural events of downtown Chestertown and Rock Hall, MD, this is more than a home—it’s a way of life.

SOLD $750,000

Liddy Campbell 410.708.5433, lcampbell@ttrsir.com

38 Chesapeake Landing

ANNAPOLIS, MARYLAND

Beautiful end-unit townhouse in an incredible location with exceptional natural light, water views, and privacy. Enjoy sweeping vistas of the Severn River, Spa Creek, and the U.S. Naval Academy from the expansive, newly renovated decks on both the main and bedroom levels. The open floor plan is ideal for entertaining, while four finished levels provide plenty of room to spread out and enjoy quiet retreats.

SOLD $1,725,000

Alex Tower Sears 443.254.5661, atsears@ttrsir.com

60

ANNAPOLIS, MARYLAND

Exquisitely renovated in-town residence with parking, just steps from the Maryland State House and City Dock. This three-level home blends historic character with modern comfort, featuring an open kitchen with exceptional storage, custom built-ins, heart pine floors, and fun designer touches. The primary suite includes a renovated bath and walk-in closet, with additional updated baths serving the other bedrooms.

SOLD $1,650,000

Alex Tower Sears 443.254.5661, atsears@ttrsir.com

138 Charles Street

ANNAPOLIS, MARYLAND

This rare detached home in Downtown Annapolis offers a garage, driveway, and timeless charm in the Historic District. Original details such as the staircase, oversized windows, and pocket doors blend seamlessly with updates that include an open kitchen/family room with cherry cabinets, granite countertops, a bar area, and a gas fireplace. Enjoy a sunroom overlooking the landscaped backyard, spacious bedrooms with an en-suite primary, and plenty of natural light throughout. Just blocks from Main Street and the waterfront, this is downtown Annapolis living at its finest.

SOLD $1,400,000

Alex Tower Sears 443.254.5661, atsears@ttrsir.com

11 Southgate Avenue

ANNAPOLIS, MARYLAND

A fully renovated classic home on one of Annapolis’ most coveted streets with its own private dock on Spa Creek. This thoughtfully updated residence features a seamless layout, a timeless designer kitchen and baths, family room addition, and beautiful water views. The fully fenced yard and excellent outdoor entertaining spaces are complemented by an exceptionally hard-to-find detached garage.

Sold for $3,517,500

Alex Tower Sears 443.254.5661, atsears@ttrsir.com

Find a home that fits your lifestyle

With offices conveniently located across Maryland, Virginia, and Washington, D.C., our local experts are always within reach—ready to guide you on your next journey.

Annapolis Brokerage 209 Main Street Annapolis, MD +1 410.280.5600

St. Michaels Brokerage

400 S Talbot Street

St. Michaels, MD +1 410.745.2596

Downtown DC Brokerage 1515 14th Street NW Washington, DC

+1 202.234.3344

Bethesda Brokerage 4809 Bethesda Ave. Bethesda, MD +1 301.516.1212

McLean Brokerage 6723 Whittier Ave, Suite 101 McLean, VA +1 703.319.3344

Alexandria Brokerage 400 South Washington Street Alexandria, VA +1 703.310.6800

Easton Brokerage 17 Goldsborough Street Easton, MD +1 410.673.3344

Georgetown Brokerage 1206 30th Street NW Washington, DC +1 202.333.1212

Chevy Chase Brokerage 5101 Wisconsin Ave NW, Ste 100 Washington, DC +1 301.967.3344

Kentlands Brokerage 345 Main Street North Potomac, MD +1 301.355.0215

Arlington Brokerage 2300 Clarendon Blvd., Ste 200 Arlington, VA +1 703.745.1212

The Plains Brokerage 6474 Main Street The Plains, VA +1 540.212.9993

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