Talbot County Public Schools Homes with Panoramic View

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "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 76+-acre waterfront estate 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. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$7,900,000

8 Beds ⋅ 6 Baths

"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 114+-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.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$5,995,000

8 Beds ⋅ 6 Baths

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "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 76+-acre waterfront estate 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. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$7,800,000

4 Beds ⋅ 5 Baths

Grafton Manour Estate—A Rare Chesapeake Waterfront Legacy. Embrace the quiet grandeur of Grafton Manour Estate, an 86±-acre peninsula wrapped by approximately 1.5± miles of shoreline with panoramic water views in every direction. Bordered by Briary Cove to the east, Harris Creek to the southeast, and Waterhole Cove to the west, this extraordinary property blends pastoral elegance with true Chesapeake Bay access. Property Highlights: 86± acres with sweeping water vistas, open fields, and meticulously manicured lawns. Varied shoreline: riprap, sandy beaches, and natural grasses. Deep-water pier with 7' MLW, suitable for larger boats and sailboats; direct access to the Chesapeake Bay. Two subdivided, waterfront lots included: Lot 2: 6± acres on Briary Cove (east side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Lot 3: 5.5± acres is located on Waterhole Cove (west side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Historic Lowes Family Cemetery on the west side, dating to the 1700s. Land mix: approximately 60± acres tillable; balance in timber and lawns along the eastern shoreline. Main Residence: Custom-built in 2004, approx. 7,400 sq ft, four en suite bedrooms. Primary suite in the main-floor north wing with private laundry, library, office/workout room, and sunroom. Dramatic great room and dining room with vaulted ceiling, chestnut beams, cedar ceiling, and a raised-hearth stone fireplace. Signature silo feature: 1st and 2nd floors: full baths serving two bedrooms. 3rd floor: window-lined observatory with 360° views across the estate. Wide-plank wood floors milled from the same chestnut as the great room beams. Exceptional craftsmanship throughout; a must-see for discerning buyers. Guest/Farmhouse: Approx. 2,000 sq ft with three bedrooms and one bath. Two wood-burning fireplaces (living room and dining room). Charming and versatile for guests, caretakers, or rental income. Barns and Outbuildings: Large heated barn with concrete floors, three overhead doors, expansive workbench, and open-loft recreation room. Attached a conditioned office/hunters’ lodge with full bath and hookups for laundry and kitchenette. Adjacent irrigated, fenced raised-bed garden; nearby small apple orchard. Additional smaller barn for equipment or livestock. Lifestyle and Possibilities: Ideal for a family compound, equestrian pursuits, or an exclusive retreat. Premier sporting opportunities: shoreline waterfowl, whitetail deer, and turkey. Ample acreage and infrastructure for hobby farming, vineyards, or conservation. A once-in-a-generation opportunity to own an iconic waterfront estate where open water, open sky, and open fields meet. Follow the country road home to the place you belong—Grafton Manour Estate. By appointment only. Do not enter the property by water or land without the listing agent. The property is monitored by camera surveillance 24/7.

22101 Grafton Manour Ln, Wittman

Listing courtesy of Meredith Fine Properties. Contact: 4107458060

$1,700,000

3 Beds ⋅ 3 Baths

Western sunsets and timeless waterfront living define this beautifully restored home on Town Creek in Oxford. A waterside pool, expansive entertaining deck, gazebo and private pier create an exceptional setting for relaxing, entertaining and enjoying life on the water. Inside, a gourmet kitchen and inviting family room with a custom built-in bar anchor the home, while warm pine floors add warmth and character throughout. Three bedrooms and three full baths include a spacious waterfront primary suite with a private second-story deck overlooking Town Creek—the perfect place to unwind while taking in spectacular western sunsets. Just moments from Oxford's waterfront park, marina, restaurants and the Oxford-Bellevue Ferry, this distinctive property is privately sited outside the Historic District and features a private pier with approximately 4 feet of mean low water, providing easy access for boating, kayaking and paddleboarding. Property is offered as part of an estate and is being sold as is.

104 Myrtle St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$3,100,000

4 Beds ⋅ 4 Baths

Set on 28 private acres overlooking Plaindealing Creek along the desirable Easton–St. Michaels corridor, this beautifully remodeled waterfront home offers 4 bedrooms, 4 full baths, and breathtaking panoramic views stretching across to Oxford, the Choptank River, and beyond. Positioned on an exceptional point of land, the property enjoys a rare combination of expansive water vistas, privacy, and direct access to some of the Eastern Shore’s finest boating and sporting waters. A scenic, tree-lined drive leads to the residence, where the water immediately takes center stage. Thoughtfully renovated in 2019, with numerous additional upgrades completed in subsequent years, the home is designed for both relaxed everyday living and effortless entertaining. The main level features a waterside primary suite with an exquisite ensuite bath, along with an additional guest bedroom and adjacent full bath(with sauna). The spacious living room is anchored by a brick fireplace with pellet stove insert, custom built-ins, and sliding doors opening to the waterside patio, creating a seamless connection to the remarkable setting. A well-appointed kitchen with stainless steel appliances and granite countertops adjoins the separate dining room, where spectacular water views provide a memorable backdrop for gatherings. Two other main-level rooms offer flexibility for an office, family room, exercise room, or other living needs, while a generous laundry room with built-ins and a secondary staircase adds everyday convenience. Upstairs are two additional guest bedrooms and two en-suite baths along with an adjoining bonus room ideal for guests or hobbies, and a second staircase. A true sportsman’s paradise, the property offers deep water, excellent fishing, private hunting, and endless opportunities for boating and recreation. The private pier, completed in 2023, features three slips, a boat lift, and a jet ski lift. With approximately 7' MLW, a newly riprapped shoreline, sandy beach, new BAT septic system installed in 2019, and a new roof completed in 2026, this exceptional waterfront retreat is perfectly suited for those seeking the very best of Eastern Shore living. *Approximately 24 acres are enrolled in a Forest Stewardship Plan. * Please do not drive in without an appointment-security monitoring.

26279 Deep Water Harbor Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$1,795,000

3 Beds ⋅ 2 Baths

A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of great restaurants, museums and boutiques but no town taxes! You will love the upgraded gourmet kitchen with granite countertops, large center island, soft close cabinetry, broad water views with Samsung stainless steel appliances where you can make your favorite dishes to enjoy. Besides the kitchen, the large Sunroom is my other favorite room of the home with large windows on three sides for panoramic water views to enjoy nature, sunsets and waterfowl along with great access to the wrap around waterside deck through sliding glass doors. I think you will agree when you see it! You will find a bonus of lovely hardwood floors throughout the home and 2 full upgraded bathrooms as well as a double sided wood burning fireplace for the cooler nights on the Shore and we all know that last winter was colder than most so it was very much enjoyed! The property includes a heated workshop for hobbies as well as 2 other sheds for extra storage should you need it but also a screened waterside Gazebo for entertainment, wraparound deck, partially covered front porch and a deeded private dock on Broad Creek with 3+ MLW with multiple slips, a boat lift and a great place to catch some fresh crabs for dinner! What are you waiting for? This could be the one you have been waiting to come on the market!

23776 Mount Pleasant Landing, Saint Michaels

Listing courtesy of Shore Living Real Estate. Contact: 4102515291

$2,475,000

7 Beds ⋅ 6 Baths

"Tranquil Waters" is a rare Chesapeake Bay waterfront retreat on Tilghman Island, comprehensively renovated to the highest standard and designed to capture panoramic water views from nearly every room. This extraordinary residence blends refined coastal architecture with the relaxed elegance of Eastern Shore living. Dramatic walls of glass, soaring ceilings, and open living spaces flood the home with natural light while framing endless Bay views, spectacular sunrises, and unforgettable sunsets. The fully renovated interior includes a redesigned chef's kitchen, spa-inspired baths, new windows and sliding doors, updated trim and fireplace features, and extensive system upgrades throughout. Exceptional waterfront amenities include expansive Trex decking, deep-water dockage, a heated indoor pool and spa pavilion, and seamless indoor-outdoor living designed for entertaining and year-round enjoyment. Major capital improvements include new HVAC systems, roof replacement, hot water heater, air purification system, decking, windows, doors, and more, offering true turnkey peace of mind. Beyond its appeal as a private waterfront retreat, "Tranquil Waters" has enjoyed a successful luxury vacation rental history, creating an appealing opportunity for buyers seeking both lifestyle and investment potential. Equally suited as a luxury primary residence, waterfront getaway, or private retreat, "Tranquil Waters" delivers the ultimate Eastern Shore lifestyle: water, light, privacy, and complete escape.

21642 Chicken Point Rd, Tilghman

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$6,995,000

7 Beds ⋅ 6 Baths

Welcome to Deep Neck Farm Lane, a stately waterfront farm overlooking Broad Creek with sweeping west and southwest views that stretch over the Choptank River to the Western Shore. This extraordinary estate captures dramatic sunsets, summer breezes, and shelter from northern winds, all from an unrivaled vantage point. Built in 2006 by a builder for their family, the 8,500± square foot residence provides thoughtful design and enduring craftsmanship. The home was built for hosting and gathering. Seven ensuite bedrooms welcome family and friends, while soaring ceilings, three fireplaces, and a cozy morning room with a wood stove set the tone for gracious living. The turret, perched to catch the last rays of daylight, reminds one that every detail was designed around the water. The accessory structures and outdoor areas for entertaining are well-positioned to capture broad views and an immense water presence. From the waterside deck of the residence to the pool house with bathroom, loft, kitchenette, and outdoor grill, to the riverfront fire pit, the focal point is Broad Creek. The broad water portion of the shoreline is protected with 1,900 feet of stone revetment, and the remaining 2,500 feet of shoreline along Bridge Creek provides a natural setting. The farm has 13 acres under cultivation, with 3.5 acres in pasture. In addition, a 40 x 60 pole barn, featuring a second-floor caretaker apartment, provides ample space for the hobby enthusiast, complete with a workshop and off-season storage.

24390 Deep Neck Farm Ln, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$2,495,000

4 Beds ⋅ 4 Baths

Timeless Tidewater Colonial-inspired waterfront estate set on 3.5± private acres with 870± feet of shoreline and panoramic water views. A rare offering combining classic architecture, thoughtful upgrades and exceptional outdoor living in one of Talbot County’s most desirable waterfront settings, with a seamless indoor-outdoor flow and water views from nearly every room. Featured in Coastal Living, the residence reflects exceptional design and offers gracious living spaces, including four bedrooms with three updated en-suite baths and three fireplaces. A custom great room with wood-burning fireplace, built-ins and fine wood cabinetry anchors the home, complemented by formal living and dining rooms each with fireplaces. The gourmet custom kitchen includes custom cabinetry, quartz countertops, KitchenAid appliances and dual pantries. Outdoor amenities include a 30,000-gallon pool, expansive lawns, mature trees, irrigation system, partial rip-rapped shoreline and private pier with electric and water. Ideal for boating, kayaking, paddleboarding and waterfront entertaining, this exceptional property offers privacy, comfort and enduring Eastern Shore appeal. Two Osprey nesting platforms convery with the property. Some furniture available under separate contract. Boat Lift sold As Is. Do not come down driveway without an appointment.

3770 Leonard Cove Lane Ln, Trappe

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$5,995,000

6 Beds ⋅ 6 Baths

Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47± acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that was at one time, the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite.

27293 Southside Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$6,250,000

5 Beds ⋅ 6 Baths

Set on 31 private acres along the peaceful waters of Hunting Creek, this exceptional Eastern Shore estate combines timeless architecture with modern sophistication. With over 1,000 feet of waterfront and approximately 6 feet of mean low water, the property offers deep-water access, stunning views, and an unmatched sense of privacy. The five-bedroom, five-and-a-half-bath residence has been completely renovated from top to bottom, showcasing impeccable finishes, custom millwork, and thoughtfully designed spaces throughout. Sunlight pours through large windows that frame panoramic views of the creek and surrounding landscape. The home features two luxurious primary suites, each offering a private retreat with refined finishes, spa-inspired baths, and generous closets. Two additional bedrooms share a beautifully designed ensuite bathroom, while a first-floor bunk room with its own bath provides the perfect space for guests. Outside, the saltwater pool overlooks the water, surrounded by manicured lawns and mature trees that extend to the shoreline. A long, tree-lined driveway creates an impressive approach to the home, setting the tone for the peaceful retreat that awaits. Located just minutes by car to Easton and St. Michaels—and even closer by boat—this Hunting Creek estate captures the very best of the Chesapeake Bay lifestyle: elegance, tranquility, and effortless connection to the water.

9170 Hunting Creek Ln, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

Talbot County Public Schools Homes with Panoramic View

Newest Talbot County Public Schools Homes with Panoramic View