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Set on 20 private waterfront acres with over 800 feet of shoreline along the Chesapeake Bay, this extraordinary estate offers a rare opportunity to own one of Maryland’s most impressive legacy properties. Behind a gated entrance and winding tree-lined drive, the residence combines timeless architecture, exceptional craftsmanship, and resort-inspired amenities designed for both grand entertaining and everyday enjoyment.

The shoreline is simply remarkable, featuring riprap protection, a private pier with lifts, sandy beach areas, water and electric service, and panoramic Bay views that deliver spectacular sunsets year-round. Whether enjoying a quiet morning by the water, setting out for a day on the Bay, or gathering with family and friends for an evening by the fire, every aspect of the property has been thoughtfully designed to embrace the waterfront lifestyle.

Inside, over 15,000 square feet of finished living space showcases Brazilian cherry flooring, handcrafted millwork, coffered ceilings, custom paneling, seven fireplaces, and beautifully curated living spaces throughout. The gourmet kitchen serves as the heart of the home, featuring premium appliances, an oversized island, sunlit breakfast room, and a fully equipped butler’s pantry designed for seamless entertaining.

The residence offers two luxurious primary suites, including a main-level retreat with fireplace, spa-inspired bath, private office, and direct access to the waterfront. Multiple ensuite guest bedrooms, a theater room, game room, exercise suite, expansive third-floor recreation space, and a private apartment above the garage provide exceptional flexibility for hosting family and guests.

Outdoor amenities rival those of a private resort. Enjoy a saltwater pool and spa, covered poolside entertaining pavilion with outdoor kitchen and fireplace, regulation tennis and pickleball court, expansive patios and terraces, fire pit, pond with fountain, playground, and extensive professional landscaping that creates a setting of complete privacy and tranquility.

This is more than a home—it is a Chesapeake Bay estate designed for generations to gather, celebrate, and create lasting memories. A rare offering where luxury, privacy, recreation, and waterfront living come together on an extraordinary scale.

STEVENSVILLE

7328 KENT POINT ROAD

8 Beds

9 Baths

14,893 Sq.Ft.

$7,995,000

MLS#: MDQA2017482

MCLEAN

6811 WEMBERLY WAY

6 Beds

7 Baths

11,600 Sq.Ft.

$7,995,000

MLS#: VAFX2292340

OXFORD

26570 OXFORD ROAD

6 Beds

4 Baths

8,667 Sq.Ft.

$7,975,000

MLS#: MDTA140036

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. Mid-morning calls for a stroll, tram or ATV ride down to your private beach, toes in the sand, as the water laps gently at the shore. Perhaps it’s time for a boat ride. Your commercial-sized pier, equipped with multiple lifts and slips, makes it effortless to set out for an afternoon on the water. The land lovers can take an easy walk into Annapolis or stay closer to home and lounge by the heated saltwater pool, where the sound of the waves blends with the laughter of loved ones. A distinguished home office showcases exquisite woodwork, built-ins, and a double-sided fireplace; a great place to catch up on some work if you can take your eyes off the mesmerizing views. As the day winds down, retreat to one of the many cozy sitting rooms including the stunning sitting room with walls of windows, a perfect hideaway overlooking the pool and river, ideal for a quiet moment with a book or a glass of wine. In the cooler months, the home's fireplaces—found in the living room, family room, office, and even the primary bath—offer warmth and ambiance. Evening entertainment takes shape in the lower-level London pub bar, where friends gather for a game of billiards or a lively conversation. A family movie night in the spacious den, a midnight swim under the stars. The possibilities are endless in a home designed for both grand entertaining and peaceful retreat. As night falls, retreat to the primary suite, a true sanctuary with a private balcony, a fireplace flickering in the background, and a spa-like bath where a deep soaking tub and towel-warming drawers create the perfect end to a perfect day. At 1900 Carrollton Road, every day feels like a dream—a life immersed in luxury, comfort, and the beauty of the Severn River. This is more than a home; it’s a legacy. Welcome Home!

ANNAPOLIS

1900 CARROLLTON ROAD

7 Beds

6 Baths

12,200 Sq.Ft.

$7,950,000

MLS#: MDAA2132676

Stoney Springs Farm is unique, recreational, and extraordinary - 315+/- acres crafted for car collectors, hunters, equestrians, and agritourism visionaries alike. Just 30 miles from Washington, DC, the property commands breathtaking panoramic views stretching from Sugarloaf Mountain to downtown Bethesda. For car enthusiasts or large-scale entertaining, the centerpiece is a masterfully BOWA built, timber-framed bank barn. Spanning 8,200 square feet on three secure and climate-controlled levels, it features Douglas Fir beams and flooring, commercial-grade capability including a chain hoist and hydraulic lift, a full kitchen with high-end appliances, 1.5 baths, and the infrastructure to showcase and care for a collection of up to 20 exotic cars. This estate also caters to the huntsman, offering mature woods, open fields, and strategically placed stands and food plots creating exceptional habitat and trophy opportunities. The custom built, 4-bedroom, 3.5 bath colonial farmhouse is comprised of 4,800 finished square feet and features a coveted main level primary bedroom suite, a gourmet quintessential country kitchen with top-of-line appliances, gorgeous reclaimed oak floors, custom millwork, an oversized and versatile upper bonus room with rear staircase, inviting front and rear covered porches offering tranquil vista and spectacular sunsets, and is equipped with Geothermal HVAC. Completing this unparalleled property is a detached three-car garage with workroom and covered porch, and a substantial and functional four-bay agricultural building. There are two high-producing wells, multiple productive crop fields and cultivable land, and is perc approved for an additional 6-bedroom house. Nationally acclaimed magnet Poolesville High School and an array of restaurants are located less than three miles away. Thoughtfully designed and built from the finest materials, with two distinct visions, this incredible and vast property now invites a new owner to write the next chapter. This is more than real estate – it’s an opportunity to curate your own recreational oasis and enduring legacy!

*NOTE: There is no sign on property, and please do not walk or drive on property without permission from listing agent.

POOLESVILLE

21100 W OFFUTT ROAD

4 Beds

3 Baths

4,878 Sq.Ft.

$7,950,000

MLS#: MDMC2156274

CHARLOTTESVILLE

2575 RIDGE ROAD

6 Beds

5 Baths

N/A

$7,950,000

MLS#: 1002549958

Presquile Manor House, originally built by the Lloyd Family circa 1800 as one of their three Plantation Houses, sits up high on the Wye River with due West Exposure. The Main House has recently gone through a two-year renovation process from top to bottom by West & Callahan Construction and Peter Zimmerman Architects Inc, with much thought and care to keep all of the historic attributes that this property deserves. The grounds are improved by a pool, tennis court, covered boat house with deep water, formal gardens, magnificent mature trees and a detached 1,670 sq ft caretaker's house. The main parcel is 10.48 acres with an additional 7.1-acre tree lined drive with a perpetual easement. This is a one-of-a-kind property and a true Talbot County piece of History. Furniture is negotiable.

EASTON

26546 PRESQUILE DRIVE

7 Beds

6 Baths

8,001 Sq.Ft.

$7,950,000

MLS#: MDTA2012904

This charming, sun drenched Colonial was originally built in 1921 and completely renovated with modern conveniences throughout in 2014. Perfectly sited on one of the highest points in McLean with panoramic views and 4.34 picturesque acres on tranquil Pine Hill Road. This charming estate is surrounded by mature landscaping and gardens providing unsurpassed privacy and a walking path to Downtown McLean. The comfortable interior, with beautiful spaces, has a welcoming Foyer that opens to the elegant Formal Living and Dining Rooms that have French doors leading to side porches. The Family Room features coffered ceilings, fireplace, a wall of windows and French doors allowing for seamless indoor/outdoor living. The Family Room opens to the chef's Kitchen that has custom cabinets, large center island, farmhouse sink and top-of-the line appliances. A cozy Breakfast Room is surrounded by windows with bench seating and French doors to the Patio. The Main Level also includes a Butler's Pantry with a beverage fridge, Office with built in desk, Mud Room, Laundry Room and screened-in-porch with a stunning stone fireplace and vaulted ceilings. The Upper Level has a wonderful Owner's Suite with vaulted ceilings, two walk-in Closets, a gorgeous spa Bath featuring separate vanities, a stand-alone tub and shower.There are 2 En-suite Bedrooms and a Sitting Room on the Upper Level and 2 more Bedrooms with a full Bath on the 3rd Level. Relax in the Basement that boasts a Media Room, Game Room,Bedroom and full Bath. The Carriage House offers a 2-car Garage and upper level space for all your hobbies or workshop needs as well a detached shed. This amazing property with its character and charm will exceed your expectations!

MCLEAN

1031 PINE HILL ROAD

6 Beds

5 Baths

8,055 Sq.Ft.

$7,950,000

MLS#: VAFX2071026

#MDTA2000142

EASTON

9380 GREGORY ROAD

6 Beds

6 Baths

8,526 Sq.Ft.

$7,900,000

MLS#: MDTA2000142

Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen with vaulted ceiling and excellent light, stainless steel commercial grade appliances, granite countertops. Beautiful draperies throughout the house, and gilded valances in LR. Old wing can serve as caretaker's quarters or home office/conference area or additional BR space. 17 x 16 second story deck off old wing, with outside staircase as well as interior access. Poolside screened porch 17 x 17 with adjacent brick terrace 12 x 26. Front brick floored open porch 12 x 48 with open porch of same size above.
Elevator accesses all three stories and is designed for a wheelchair use.
Primary bedroom suite has walk-in closets, two large bathrooms, and dressing room with fireplace.
Bar off FR has built-ins, two wine refrigerators and an ice machine.
Pool 22 x 44 plus apron and brick wall. Pool is long enough for lap swimming. Loop-lock cover is almost new.
HIGH SPEED FIBEROPTIC INTERNET SERVICE is available from Easton Velocity. The line has just been run. Owner has not yet connected.
Close to the amenities of St. Michaels, with shopping, restaurants and Chesapeake Bay Maritime Museum.
Talbot County has an airport on the northwest edge of Easton.

2700 sq ft caretaker's/guest house remodeled 2004/2005. 9.5 ft ceilings; 15 x 6 foyer; 17x 12 eat-in K;
23' x 19' LR with f/p and built in bookcases; 16 ft sq screened porch with great water view;; half bath.; first floor BR 19 x 13 with f/p and en-suite bath; 2d story has 17x 13 BR with fireplace and en-suite bath, 15 x 13 sitting room, 15 x 14 BR. full bath. "B.A.T" (best available technology) septic system new in 2025. Guest house roof less than two years old. Flower cutting beds, vegetable garden and orchard.
Art studio (16 ft square) on high ground close to Tilghman Creek.
Extensive barns and sheds, including a barn with 5 stalls, tack room and hayloft.
Horse caretaker's apartment near barns.
Incredible camellias, flowering trees, Spring bulbs.

Rich Neck Manor is Talbot County's earliest land grant (1649/1651), The main block of the house was built for Samuel Harrison ca. 1824, Original pine floors, late Federal paneled doors and surrounds, elegant three-story staircase, mantelpieces, etc. The brick dairy (12 x 22) is an architectural "folly" built by Harrison, now used as a chapel. Attached to the Harrison house is a ca. 1740 gambrel-roofed brick kitchen (16 x 36) dating to the days of Matthew Tilghman Ward, while the brick smokehouse (20 x 20), and caretaker/guest house date to ca 1790. Rich Neck Manor was also the home of Revolutionary War patriot Matthew Tilghman. See attachments for history.
This property is protected by a land conservation easement and by a MHT historical easement (see documents attached to this listing). The easement holders are helpful with advice and share their knowledge and experience.
Hunting is outstanding on this property and the hunting rights are available to buyer. Fishing is unsurpassed, and the Miles River crabs are said to be the largest, heaviest crabs on the Shore.
WATER DEPTH: the deepwater harbor is on Tilghman Creek. The "dock" is next to the art studio and consists of a bulkheaded and backfilled area with pilings and slips. It is believed that this area was dredged, but the current depth is uncertain. There is an electronic boat lift here. It has been suggested that the new owner should construct a pier perpendicular to the shore, thereby securing very deep water. The mooring belongs to this property
Available partly furnished.

CLAIBORNE

10770 RICH NECK ROAD

8 Beds

5 Baths

10,240 Sq.Ft.

$7,900,000

MLS#: MDTA2010384

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 115-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees.

The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor.

Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage.

The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath.

The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy.

The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds.

An adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house.

With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

WITTMAN

8612 TILGHMAN ISLAND ROAD

8 Beds

5 Baths

9,051 Sq.Ft.

$7,900,000

MLS#: MDTA2012146

ROSE HILL ESTATE — 352 ACRES OF HISTORIC ELEGANCE AND AN ELEVATED COUNTRY LIFESTYLE
Featured in Architectural Digest, this Amelia T. Handegan–designed residence anchors one of Virginia’s most distinguished country estates. Encompassing 352.24 acres, the property offers timeless elegance, masterful restoration, and unparalleled privacy. Designed for those who value both heritage and luxury, every detail reflects refined craftsmanship and enduring beauty. The estate’s remarkable grounds and gardens were further recognized with the 2016 ASLA Virginia Chapter Merit Award, honoring the property’s exceptional landscape architecture and stewardship.

Protected under conservation easement, the estate’s rolling landscape unfolds through two gated entrances across open fields, century-old hardwoods, formal gardens, and a stocked pond—offering a rare balance of seclusion, scale, and natural beauty.

Originally built in 1799, the residence was comprehensively restored in 2011 by Tidewater Preservation, Inc., under the direction of acclaimed Charleston designer Amelia T. Handegan. The result is a seamless blend of historic integrity and modern sophistication, enhanced by geothermal climate control and radiant floor heating.

The 5,431-square-foot main residence features 4 bedrooms, each with an ensuite bath, and a collection of gracious living spaces defined by hardwood floors, intricate crown molding, chair railing, and custom French wallpaper. Formal rooms include a dining room with fireplace, an elegant living room with built-ins, and a distinctive octagonal music room with English windows and hand-painted geometric floors.

The chef’s eat-in kitchen pairs historic character with professional-grade function, offering custom wood cabinetry, a wood-burning fireplace, marble-topped island, Wolf range, paneled appliances, wine refrigerator, and ice machine. A well-appointed mudroom with built-ins and laundry provides convenient access to the gardens.

The main-level primary suite is a private retreat, featuring a fireplace, sitting room with built-ins, walk-in closet, and direct access to the outdoors, along with a marble-clad bath complete with dual vanities, soaking tub, and walk-in shower. Additional bedroom suites offer fireplaces, built-ins, and beautifully appointed baths, each capturing sweeping views of the rolling countryside, pond, or historic gardens.

Beyond the main residence, a guest cottage with exposed beams, marble finishes, and a fireplace offers refined accommodations for visitors. A Pennsylvania bank barn, relocated in 2009, has been thoughtfully reimagined to include a gym, office with full bath, and loft. Distinctive architectural elements include a Thomas Jefferson–inspired dovecote with Birmingham Rollers and a newly constructed folly overlooking the pond.

Outdoor amenities are equally exceptional, featuring a tennis court with pavilion, croquet lawn, riding trails, and formal gardens that have been showcased in Garden Club tours, filled with hydrangeas, peonies, fruit trees, and rose of Sharon. A working barn supports a herd of Belted Galloway cattle, further enhancing the estate’s pastoral character.

Utilities include well water, septic, geothermal HVAC, propane heat (two owned tanks: 500 and 1,000 gallons), radiant floor heating, and four hot water tanks.

A rare and significant offering, Rose Hill Estate embodies a legacy property—where history, land, and lifestyle converge in extraordinary form.

RAPPAHANNOCK ACADEMY

23348 TIDEWATER TRAIL

4 Beds

4 Baths

5,431 Sq.Ft.

$7,900,000

MLS#: VACV2008326

Welcome to this fabulous waterfront estate historically known as The POD. Set behind the gates of an extraordinary 7+ acre waterfront compound, The POD offers a rare blend of privacy, scale, and resort-caliber living along Forked Creek and the Severn River. Beautifully constructed and thoughtfully curated, the property unfolds as a true lifestyle destination, where every detail has been designed to elevate both everyday living and grand entertaining.

A long, illuminated drive framed by mature crape myrtles leads to expansive, meticulously landscaped grounds. Outdoor living takes center stage with sweeping wraparound decks, multiple gathering spaces, and a heated saltwater pool surrounded by travertine stone, gazebo, and fire features. An outdoor kitchen, complete with EVO grill, gas burners, refrigeration, and bar seating, creates the perfect setting for waterfront entertaining, while the year-round spa and low-maintenance turf with putting green enhance the ease of ownership.

The private pier is a standout, offering multiple slips, lifts, floating dock access, and approximately 10 feet of water depth. An exceptional experience that is ideal for boating enthusiasts seeking effortless access to the Severn River and beyond.

Inside, the main residence spans approximately 8,000 square feet, where refined finishes and architectural details are complemented by a light-filled, flowing layout. A grand foyer introduces the home, leading to elegant living and dining spaces, a chef’s kitchen equipped with premium appliances, and a welcoming sunroom overlooking the pool and waterfront. The main level Primary suite with private balcony, fireplace and spa-like bath is the perfect retreat after a day in the pool or on the water. A conveniently located elevator provides seamless access to all 3 levels.

Designed for both relaxation and recreation, the lower level transforms into a true entertainment hub, featuring a nightclub-inspired lounge with full bar, a state-of-the-art theater, and dedicated fitness and recreation spaces. Head upstairs where an additional 3 bedrooms, 2 baths and an awe-inspiring office with wrap around deck offer comfort and flexibility for family and guests. A separate guest house offers additional accommodations with its own kitchen, living spaces, 3 bedrooms 2 baths and private comforts, an ideal retreat for extended stays or hosting with ease.

Advanced infrastructure and smart home technology, including whole-house automation, security, generator, and climate systems, ensure modern convenience is fully integrated into this exceptional offering.

The POD is more than a home, it is a private waterfront retreat designed for those who value space, privacy, and a seamless connection to the water. A truly resort-inspired setting, this property offers an unparalleled opportunity to experience the waterfront lifestyle in its most complete and effortless form. Welcome Home!

SEVERNA PARK

423 BENFIELD ROAD

4 Beds

4 Baths

7,964 Sq.Ft.

$7,900,000

MLS#: MDAA2135920

CATLETT

ELK RUN ROAD

None Beds

None Baths

N/A

$7,900,000

MLS#: VAFQ2012698

WARRENTON

4333 LONGWOOD LANE

3 Beds

2 Baths

3,448 Sq.Ft.

$7,900,000

MLS#: VAFQ2014516

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