Talbot County Public Schools Homes with Panoramic View

8410 Bozman Neavitt Rd, Bozman

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283

First Time Offered! This meticulously maintained, custom-quality stick-built Cape Cod is beautifully situated in an idyllic country setting. Thoughtfully designed with three bedrooms and two-and-a-half baths, the home offers generous, light-filled living spaces, recessed lighting throughout and high-speed internet. A dramatic vaulted ceiling enhances the living room, while the gourmet kitchen, formal dining room and adjoining sunroom create an inviting setting for everyday living and entertaining. An oversized recreation room provides exceptional flexibility for gatherings, hobbies or a media room. The spacious primary suite features a vaulted ceiling, direct access to the hot tub and a spa-like bath with dual vanities, a walk-in shower and soaking tub. Two additional bedrooms and a full bath provide comfortable accommodations for family and guests. Significant improvements include a new roof and gutters in 2025, numerous replacement Andersen windows and updated porch windows with retractable screens. Outside, the private grounds are designed for relaxation and entertaining with an in-ground pool, hot tub and generous outdoor living space surrounded by peaceful country views. A substantial 30-by-40-foot outbuilding offers exceptional space for a workshop, storage, vehicles or recreational equipment. Lovingly cared for by its original owners, this special property combines quality construction, thoughtful updates, privacy and relaxed Eastern Shore living.

30108 Deep Branch Ln, Trappe

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

$9,950,000

4 Beds ⋅ 6 Baths

Set on the coveted shores of the Tred Avon River, this extraordinary waterfront estate is a rare offering, combining deep-water boating, a private sandy beach, a substantial main residence, separate guest accommodations, and an exceptional collection of lifestyle amenities. From the first approach, the property unfolds as a private Eastern Shore compound, where elegant architecture, sweeping river views, and resort-caliber amenities are seamlessly integrated into a singular waterfront setting. The four-bedroom, five-and-a-half-bath main residence is both impressive and inviting. A dramatic two-story living room features hardwood floors, a fireplace, custom millwork, and abundant natural light, while the waterside den offers a more intimate retreat with a gas fireplace, custom bookshelves, and a wall of glass framing views across the Tred Avon. A spacious screened porch and expansive Ipe decking extend the living spaces outdoors and provide direct access to the waterfront. At the heart of the home, the kitchen is equipped with a Sub-Zero refrigerator, gas cooktop, double ovens, stainless steel dishwasher, granite countertops, and white cabinetry, along with generous space for casual dining. A first-floor office and laundry room add everyday convenience, while dual staircases provide easy access throughout the home. The first-floor waterfront primary suite is a private sanctuary with its own fireplace, sitting room with custom bookshelves, two walk-in closets with custom shelving, and a beautifully appointed bath featuring a waterside soaking tub, dual vanity, and walk-in steam shower. Each additional bedroom is en suite, creating comfortable and private accommodations for family and guests. Outside, the property transforms into a private waterfront retreat. A heated lap pool, hot tub, and sandy beach create distinct places to relax along the river, while a scenic walking path winds through wildflower gardens and open space, reinforcing the estate’s remarkable sense of privacy and scale. The pool house makes outdoor entertaining effortless, with a full kitchen, stainless steel appliances, gas range, laundry facilities, and an outdoor shower. A separate three-bedroom, two-bath guest residence provides exceptional additional accommodations with hardwood floors, a full kitchen, laundry, garage, and a large deck overlooking the Tred Avon—ideal for extended family, guests, or multi-generational living while preserving the privacy of the main residence. For those drawn to the water, the property delivers. A private pier offers 6+ feet of water at mean low water, three slips, two boat lifts, water and electric—providing exceptional deep-water access for a wide range of vessels. From here, spend the day cruising the Tred Avon and exploring the waterways of the Chesapeake Bay. A rip-rapped shoreline provides protection while preserving the property’s connection to the river. With a three-car garage, irrigation system, extensive custom millwork, guest and pool houses, heated pool, sandy beach, and substantial boating infrastructure, this is far more than a waterfront home. It is a complete Eastern Shore estate—a private compound where the residences, grounds, and waterfront amenities come together to create an exceptional lifestyle on the Tred Avon.

6920 Travelers Rest Cir, Easton

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

$13,750,000

5 Beds ⋅ 9 Baths

Stock Range Farm spans 350 acres of prime waterfront and is available for purchase in its entirety OR with reduced acreage including the main residence, if the buyer so chooses. Options include selling main residence with 20+ acres, 40+ acres, and 100+ acres. **CALL listing agent for more information! The property is free of easements and includes development rights, subject to all applicable Talbot County zoning regulations. With vast working farmland and resort-style amenities, this rare gem truly combines luxury and sophistication with seclusion and tranquility. The 12,000+ sq. ft. primary residence showcases the breathtaking stylings of acclaimed architect Peter Jay Zweig and exemplifies the pinnacle of luxury living. Built by Ilex Construction, striking architectural details and unparalleled craftsmanship are demonstrated throughout, seamlessly integrating with the breathtaking beauty of the landscape. This magnificent home is filled with an abundance of natural light and boasts panoramic views, thanks to soaring glass walls that overlook the tranquil waters of Pickering Creek, expansive fields, and picturesque vineyards. The thoughtfully curated interior includes spacious living areas, a stunning owner's wing that offers privacy and comfort, and a separate guest wing that features a full kitchen, providing ideal accommodations for family and visitors. High-end features abound, including a gourmet kitchen, recreation room complete with kitchen and bar for entertaining, full exercise room, 5 car garages, elevator, heated limestone floors, Venetian plaster walls, and multiple outdoor decks. At every turn, this property exudes the loving care it has received. Outside, the resort-style amenities include a large, heated infinity pool, complete with waterfall and hot tub, stunning pool pavilion with full outdoor kitchen, stone fireplace, and two TV’s and AV system. Along with the waterside tennis/pickleball court, tranquil koi pond, and private pier with 4-5’MLW, the opportunities for outdoor fun and relaxation are boundless. In addition is the beautifully renovated 4-bedroom guesthouse with views of the vineyards, providing comfortable accommodations for family and friends. A well-equipped 9-stall barn includes a tack room/office, kitchenette, and a riding ring, complemented by 20 acres of fenced pastures. There is also a 3-4 BR caretaker's home, a fully outfitted greenhouse, large equipment barn complete with an office and full workshop, and hay barn for storage. The property also offers excellent hunting opportunities, making it a versatile retreat for outdoor enthusiasts. The highlights of this extraordinary property continue through every acre, including sweeping landscapes and hardscapes, 200 acres of working farmland, 5 acres of vineyards, and a 6-acre stocked pond with private island. Unparalleled in its mix of tranquility and luxury, the opportunity to experience the very best of the Eastern Shore’s refined lifestyle and natural beauty is only possible at Stock Range Farm. Please don't drive in driveway as there are security cameras and alarm. All appointments must be made with listing agent and additional information and details are available upon request.

27772 Sharp Rd, Easton

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

$3,295,000

5 Beds ⋅ 5 Baths

Welcome to this exceptional 4/5 BR/4.5BA waterfront residence overlooking picturesque Town Creek in the historic waterfront town of Oxford. Built in 2023, this home is privately set on 1.71 acres (very rare for Oxford) surrounded by mature trees, extensive landscaping and thoughtfully designed hardscaping that complement the natural beauty of its serene waterfront setting. Designed with extraordinary attention to detail, the home showcases soaring vaulted ceilings, expansive windows, and multiple decks and balconies that capture tranquil water views from nearly every room. The grand living room, anchored by a gas fireplace, flows effortlessly into the dining area and an extraordinary chef’s kitchen featuring a large center island, separate casual dining space, a well-appointed butler’s pantry, and a screened porch just off the kitchen - perfect for outdoor dining and enjoying the peaceful waterfront setting. A private office with an adjacent full bath offers flexibility as a guest suite. The desirable main-level primary suite is a luxurious retreat, complete with a spa-inspired bath, private sitting room, and sliding doors opening to a peaceful screened waterside porch. The second floor offers three additional guest bedrooms, including one with an ensuite bath and two connected by a Jack & Jill bath, providing comfortable accommodation for family and guests. Outdoor living is equally impressive, featuring a waterside slate patio with expansive views, ideal for relaxing or entertaining while enjoying the serene waterfront setting. A new pier with two slips and 4’ MLW provides convenient boating access, while a thoughtfully integrated rainwater harvesting and management system was incorporated as part of the property’s environmental site design. Located just a short stroll from downtown Oxford, this beautiful waterfront home offers the perfect blend of luxury, comfort, and small-town coastal living. *Home built out of flood zone: Elevation certificate available *Room for pool; plans available for pool and pool house.

104 East St, Oxford

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

$2,295,000

3 Beds ⋅ 6 Baths

With its central Talbot County location and effortless one‑story layout, this move‑in ready waterfront retreat offers a rare blend of convenience, comfort, and stunning natural beauty. Set on more than two acres on Trippe Creek with 185' of water frontage—directly across from Talbot Country Club—the property enjoys an elevated vantage point with broad water views, a private pier, and a heated pool and hot tub all just minutes from the amenities of both Oxford and Easton. The 3,100‑plus square‑foot home is designed for easy living, with sweeping waterside views and a newly renovated primary suite featuring a luxurious private bath with a steam shower. Two additional bedrooms, a bunkroom plus three full baths provide ample space for guests. The gourmet eat‑in kitchen, formal dining room, large living room with fireplace, separate family room create a warm, flexible layout for everyday living and entertaining. A screened porch offers the perfect spot to enjoy the breeze off the creek. Thoughtful updates throughout the home preserve its beautiful hardwood floors, moldings, and character while introducing a fresh coastal palette, contemporary kitchen and baths, new roof and Hardie board siding, and numerous additional improvements. The grounds are exceptional—one of the most beautiful settings in the county—with mature specimen trees, curated landscaping, full yard and garden sprinkler system, invisible dog fence and uncommon topography that enhances both privacy and views. The dedicated nature preserve directly across the street ensures no future building. A waterfront property of this quality, setting, and convenience with no flood insurance required is a rare find. Added bonus--enjoy a front row seat without leaving your own property to enjoy TCC's incredible 4th of July fireworks! Don’t miss the opportunity to make 5920 Oxford Road your own.

5920 Oxford Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$3,495,000

4 Beds ⋅ 5 Baths

Located at the end of a private, gated, park-like lane, mid-way between Easton and Oxford: This gracious home is situated on one of the premier sites in Talbot County, MD...2.3-acre point of land, providing Westerly (SUNSET) views looking directly down Trippe Creek toward the Tred Avon River. The recently updated brick home provides exceptional water views from most rooms, especially from the living room, dining room and brick-floored glassed "River Room." The floor plan (see downstairs and upstairs plans in the attached photos) features 2-bedrooms down stairs (including a "Primary" Bedroom) and 2 bedrooms upstairs (Including another "Primary" - take your pick!). A total of four large bedrooms, four bathrooms and one half-bath. Lots of living and entertaining spaces downstairs, including a spacious living room, family room, library and River Room. Recent updates include a new BAT septic system; encapsulated crawl space; refinished wood floors throughout; fresh paint inside and out; new kitchen countertops; new kitchen appliances; updated bathrooms and more. This is a true "turn-key" home. For boating, there is a substantial private pier (6' x 135') which provides 6+ ft of depth at low tide (MLW). By boat, the town of Oxford and the open waters of the Choptank River are just a short, scenic 5-mile boat ride downstream. By car, this prime location is conveniently located approx. 5-miles to Easton or 5-miles to Oxford.

28161 Harleigh Ln, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$985,000

4 Beds ⋅ 3 Baths

Beautiful views of Harris Creek and the Choptank River beyond provide a stunning backdrop for this beautifully maintained home in the established community of Tilghman on Chesapeake. A welcoming front porch framed by mature landscaping and colorful gardens leads into a bright, light-filled interior featuring soaring two-story ceilings, hardwood floors, crown moldings, and abundant natural light. Designed for both everyday living and entertaining, the gourmet kitchen opens to a spacious family room with a gas fireplace, breakfast area, and inviting sunroom. The adjoining rear deck, complete with a hot tub, provides a wonderful setting for outdoor entertaining while overlooking the beautifully landscaped grounds and tranquil water views. The main level also includes gracious formal living and dining rooms, as well as a private office. The upper level overlooks the family room below and features a spacious primary suite with a private balcony and luxurious ensuite bath with a jetted tub and walk-in shower. Three additional bedrooms—one currently used as a library—share a full hall bath. An attached two-car garage provides convenient parking and storage. Residents of Tilghman on Chesapeake enjoy an exceptional array of amenities, including a waterfront clubhouse, swimming pool, picnic area, community pier, and private boat slips available for lease, offering residents an ideal opportunity to enjoy the waterfront lifestyle of Maryland’s Eastern Shore.

21477 Island Club Rd, Tilghman

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

$2,195,000

3 Beds ⋅ 3 Baths

Set on 3.3 private acres in the established community of Travelers Rest, this beautifully restored brick residence enjoys sweeping views of the Tred Avon River from nearly every room. Thoughtfully designed for one-level living, the home combines classic architectural character with extensive updates by the current owners and a floor plan that is both comfortable and highly functional. The interior has been carefully updated while retaining the character of the original home. Improvements include beautiful hardwood flooring, a renovated kitchen, new HVAC system, Rinnai tankless water heater, new roof (2017), new deck, and numerous additional enhancements. A complete list of improvements is available from the listing agent. The three-bedroom, three-bath residence includes a spacious waterside primary suite with a generous ensuite bath, ample closet space, and additional storage. Two additional bedrooms share a full bath and are privately positioned for family or guests. The main living spaces take full advantage of the river setting. The generously proportioned living room features a wood-burning fireplace framed by custom built-in bookshelves, while the formal dining room provides a gracious setting for entertaining. The renovated kitchen features a large center island and premium appliances and opens directly to the family room, where a wood stove, breakfast area, and wall of built-in bookshelves create a comfortable gathering space. An adjoining bonus room offers exceptional flexibility and could serve as a walk-in butler’s pantry, hobby or craft room. The enclosed sunroom, with its attached full bath, is a particularly appealing space from which to enjoy the expansive water views. An oversized attached two-car garage provides convenient access to extensive attic storage that runs the full length of the house. A detached climate-controlled studio adds valuable additional space for an art studio, home office, workshop, or other uses. Outside, the property is equally well appointed. A gunite pool, added in 2020, is surrounded by extensive hardscape and fencing, offering a private setting for outdoor enjoyment. The new dock, completed in 2024, includes two slips, a floating dock, and approximately 6'MLW, providing excellent access to the Tred Avon River for boating and fishing. With its coveted location, private acreage, substantial improvements, exceptional water access, and panoramic Tred Avon River views, this is a distinctive Eastern Shore waterfront property that offers both privacy and a relaxed, livable setting.

27476 Travelers Rest Ct, Easton

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

$7,900,000

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

Talbot County Public Schools Homes with Panoramic View

Newest Talbot County Public Schools Homes with Panoramic View