Talbot County Public Schools Homes with Rip-Rapped Lot features

Simply Sensational! Sunrise views over Town Creek set the tone for this beautifully designed four-bedroom waterfront home, where contemporary architecture meets the warmth of a waterfront cottage. The main living areas include a formal living room and dining room, each with a fireplace, a bright eat-in kitchen and an inviting family room, where walls of windows frame the water views and fill the home with natural light. Two first-floor bedrooms offer the convenience of main-level living. Upstairs, two ensuite bedrooms open to the second-floor sun deck, including a spacious primary suite with floor-to-ceiling windows overlooking Town Creek.An expansive waterside patio and pool create the perfect setting for relaxing and entertaining. The separate one-bedroom guest house/pool house and detached workshop provide additional space for family, guests, hobbies or a home office. The private pier, complete with a boat lift and floating dock for kayaks and paddleboards, provides easy access to the Tred Avon River and the Chesapeake Bay. Located in the historic waterfront village of Oxford, this exceptional home captures the beauty, charm and relaxed waterfront lifestyle that define Maryland's Eastern Shore. The property is offered with its furniture allowing for an effortless transition.

106 E Division St, Oxford

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

$5,295,000

4 Beds ⋅ 7 Baths

First time offering in Morgans Point. Custom built estate designed by architect Lauren Dianich of Atelier 11, this elegant Georgian-style brick and shingle residence offers over 5,200± square feet of thoughtfully designed living space filled with natural light and panoramic water views of the Tred Avon River. Set on 5± acres, the home is crafted for both refined entertaining and private, relaxed waterfront living. The heart of the home is the River Room, surrounded by windows that frame sweeping views of the Tred Avon River. Hardwood floors by Universal Floors in D.C. feature an inlaid compass medallion that points to magnetic north, creating a distinctive focal point. A fireplace anchors the space, with a screened-in porch with its own fireplace just beyond, perfect for enjoying chilly evenings. The chef’s kitchen is equipped with professional-grade appliances including a Wolf range and double wall ovens, Sub-Zero refrigerator, Asko full-size dishwasher, and Fisher & Paykel dishwasher drawers. A large island offers a wine fridge and illuminated display cabinetry, while the butler’s pantry—complete with an additional refrigerator and charming porthole windows framing water views—enhances the home’s functionality. Additionally, a custom-built oval wet bar with a two-drawer Sub-Zero refrigerator offers substantial cabinetry. This space provides a natural gathering point for entertaining. A large mudroom with powder room provides convenience for busy households. Also on the main level are a library with floor-to-ceiling shelving and a wood-burning fireplace, a fitness room with water vistas, a formal half-bath, and a first-floor en-suite bedroom ideal for guests. A dedicated utility entrance allows for discreet service and maintenance without entering the main living spaces. A 25kW standby generator provides reliable backup power for the main residence, offering peace of mind during outages. Upstairs, the primary suite with a gas fireplace serves as a retreat, with its spacious bathroom offering a shower, jetted soaking tub, and two walk-in closets—one with its own half-bath. Additional bedrooms include an upper-level en-suite and family-friendly accommodations, all supported by a conveniently located laundry room. Completing this floor is a private office with a gas fireplace and panoramic river views, offering an inspiring space for work or study. A generously sized, detached three-car garage includes a second-floor guest quarters with a kitchenette, washer and dryer, and en-suite bedroom, where windows capture tranquil water views. Outdoors, enjoy resort-like amenities including a heated pool with a fully retractable cover and a pool pavilion with its own bathroom and outdoor shower. The grounds are beautifully landscaped and designed for relaxation, with serene river views visible from nearly every room of the property. This rare offering seamlessly blends architectural pedigree, modern luxury, and a spectacular setting on the Tred Avon River—an exceptional opportunity to experience Eastern Shore living at its finest.

5381 Morgans Point Dr, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$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

$7,900,000

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

$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

$1,200,000

3 Beds ⋅ 3 Baths

Unique Tilghman Island Property. Zoned Residential-Commercial. Situated on a 2.74 acre fenced yard. This 2450 sq ft Stone Rancher has many upgrades, new 2 car garage and 24 new commercial slips. The possibilities are endless....... Vacation Rental, 24 brand new slips, typically rent from 175.00-225.00 monthly. Develop a new fishing center, crabbing tours, sunsets cruises. Let's see what you can dream up??

21441 Dogwood Cove Rd, Tilghman

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

$3,495,000

4 Beds ⋅ 5 Baths

Rare opportunity to acquire a well-appointed home with immense views and convenient proximity to St Michaels. Ideally located by land and sea in Chance Hope Farm on the Miles River at the confluence of Eastern Bay, this stunning, classic eastern shore brick colonial has everything the most decerning buyer needs. This Daffin custom-built home features a generous, main-level primary suite featuring a spa-like bath with heated floors, a large soaking tub and separate shower, and two walk-in closets. The kitchen is a chef’s dream, featuring high-end stainless-steel appliances, a wine cooler, a warming drawer, and a massive island. There are also formal living and dining rooms, two office spaces, a recreation room, and a river room that enjoys views of Eastern Bay and beyond. The park-like lot has 220+/- feet of rip-rapped shoreline, a private pier with 3’ of MLW, lush landscaping, and a waterside deck with an outdoor kitchen.

24678 New Post Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$2,175,000

4 Beds ⋅ 4 Baths

Discover a serene retreat in the heart of Waverly Island Estates, where a major renovation in 2025 breathes new life into this charming Cape Cod home. Spanning 2.77 acres, this property offers a perfect blend of comfort and nature, featuring 4 spacious bedrooms and 2 full and 2 half bathrooms, ideal for both comfort and relaxation . Step inside to find a beautifully maintained interior with hardwood and ceramic tile flooring, complemented by a cozy fireplace that invites warmth and gatherings. Outside, the allure continues with a personal pool and a stunning view of the Tred Avon River. Enjoy the tranquility of waterfront living with 200 feet of river frontage, complete with a private dock site, perfect for boating, fishing, or simply soaking in the picturesque surroundings. The lot features rip-rap for added stability and a peaceful, no-thru street setting that enhances privacy. With ample parking, including a side-entry garage and driveway space for guests, convenience is at your fingertips. Embrace the lifestyle of riverfront living, where you can kayak, swim, or enjoy a leisurely day on the water. This home is not just a property; it’s a sanctuary waiting for you to create lasting memories. Experience the perfect blend of comfort, nature, and adventure in this exceptional residence. Only a few short miles to downtown Historic Easton, YMCA, shopping and parks.

7272 Waverly Island Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$2,495,000

3 Beds ⋅ 3 Baths

Tucked away on approximately 3 private acres along Plaindealing Creek just off the Tred Avon River, this striking waterfront retreat offers the perfect blend of Mid-Century Modern style, open-concept living, and exceptional Eastern Shore lifestyle amenities. With approximately 5’ MLW, a private dock with boat lift and floating dock, and sweeping water views from nearly every room, this property is designed for effortless waterfront living. The 3-bedroom residence features a desirable main-level primary suite with expansive creek views and direct access to the rear deck. The updated kitchen is a showpiece, centered around a massive U-shaped island with gas cooktop, abundant seating, and seamless flow into the light-filled living spaces. Hardwood flooring runs throughout most of the main level, while soaring ceilings and expansive windows create an airy, open feel that beautifully captures the surrounding waterfront scenery. Upstairs, two additional bedrooms share a full bath, accompanied by an open loft overlooking the foyer and living room — could be used as an office space or sitting area. Outdoor spaces are equally impressive. A sprawling rear deck stretches across the back of the home with access from the primary suite, living room, and kitchen, creating effortless indoor-outdoor living. The in-ground pool, mature landscaping, attached 2-car garage, and detached garage/workshop/storage building complete this exceptional waterfront offering. A rare opportunity to enjoy privacy, boating, and timeless architectural style in one of Talbot County’s most desirable waterfront settings.

26282 Deep Water Harbor Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

Talbot County Public Schools Homes with Rip-Rapped Lot features

Newest Talbot County Public Schools Homes with Rip-Rapped Lot features