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$5,950,000
5 Beds 5 Baths
Osprey Point is a one-of-a kind, highly crafted composition of nature, architecture and art. Private and serene, authentic Eastern Shore retreat or family compound with spectacular sunsets, deep-water pier and approximately 1500 feet of shoreline. The 6.69+/-acre park-like setting features west and southwest exposure of Island Creek with prevailing, cooling summer breeze, exceptional panoramic water views, a multitude of beautiful, specimen trees and gardens, sweeping lawns, protective living-shoreline, and small, stone revetment jetties. The sale includes an additional 2.32+/-acre waterfront lot with high elevation. Designed by Pamela Gardner and built by Peter Hanlon in 1996, this architecturally distinctive yet elegant and classic 5,828 square foot home with two turrets, gorgeous exposed-beams, and stunning woodwork offers light-filled, water views from every room. The warm, open and inviting interior spaces lend to relaxation and enjoyment of the outdoors from within. The waterside pool, patios and porches are wonderful for entertaining guests and the stately entrance and vast, manicured lawns are welcoming. Grand entry within the front turret showcases its beauty with up-lighting. Rear turret includes a scenic third floor overlook with kitchenette for an additional private space to unwind. The first floor includes a large open kitchen featuring hand-painted, ceramic tiles depicting the wonderful wildlife of Chesapeake Bay, a walk-in wine cellar/ larder and separate pantry, the primary bedroom suite with two walk-in closets, a very large office or additional 5th bedroom, great room with wood burning fireplace, cathedral ceiling and large bar area, the family room with gas fireplace and dining area. The formal dining room is located across the hall from the kitchen. There are many hand-crafted built-ins throughout and additional level attic storage on the second floor. Oversized three car garage has fourth bay for boat and outdoor toy storage. Osprey Point is the ideal location between Oxford and Easton. By water, this address also provides quick access to some nearby, locally known beaches, restaurant and ice cream establishments of Oxford as well as the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina.

28080 Brick Row Dr, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$19,995,000
6 Beds 12 Baths
Nestled along the picturesque Tred Avon River, this extraordinary estate comprises two expansive waterfront parcels totaling 11 acres. A masterpiece of luxury living, the centerpiece is a magnificent 3-level palatial brick home with 6 bedrooms, 7 full baths, 5 half baths, and 7 gas fireplaces set on nearly 7 acres, complemented by an adjoining 4-acre vacant lot. Enjoy the private dock boasting approximately 3 feet of mean low water (MLW), complete with 2 boat lifts, 4 jet ski lifts, and a floating pier to launch your kayaks. The residence is a grand architectural marvel featuring a 2,300+ square foot primary suite with sitting room, breakfast bar, two bathrooms, two walk-in closets, and a spacious, private terrace. Revel in the epitome of entertainment with tons of outdoor terrace space, a built-in barbecue, an indoor pool, spa, and sauna, and a finished, daylight lower level equipped with a wine cellar, second kitchen, and built-in bar. The property is adorned with a pavered driveway, offering a stately approach to this waterfront oasis. Conveniently located between Easton and Oxford and just minutes from a country club, jet airport, theatres, fine dining, shopping, and healthcare, this property is approximately 2 hours from Philadelphia and 1.5 hours from DC and Baltimore. **Click on the Movie Camera for Video Tour**

5369 Morgans Point Dr, Oxford

Listing courtesy of Meredith Fine Properties. Contact: (410) 822-6272

$4,995,000
3 Beds 4 Baths
Location, Location, Location. "RiversMeet" is located in one of Talbot County's finest waterfront sites, at the confluence of the Tred Avon and Choptank Rivers. The 12 mile view down the length of the Choptank River and across the Chesapeake Bay is unrivaled. The home was constructed in 2006 of superior materials on a raised site. It includes a a culinary trophy kitchen, a great room evoking a ship on its back during construction, classic media room, and a river room adjacent to side grotto pool. There is an elevator providing access to two en-suite bedrooms and a massive primary suite with a balcony surveying the entire view beyond Dorchester County. A 65' deeded boat slip with floating dock is conveyed with the property and is conveniently adjacent to the private driveway. There is 8' MLW in the slip and through Bachelors Harbor Marina and to the Tred Avon River. Enjoy frequent sightings of an Eagle nesting pair and Osprey in season.

26025 Bachelors Harbor Dr, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 673-3344

$9,850,000
7 Beds 8 Baths
Explore the allure of this hidden jewel in Oxford where refined luxury merges effortlessly with coastal charm. Nestled across 20+ elevated acres, spend your days meander through covered walkways, cobblestone paths, ornamental trees, scenic gardens, and panoramic point-of-land views that captivate the senses. Originally constructed in 1938, Widgeon Point has undergone a complete transformation by skilled artisans and architects, resulting in a stunning residence with guest house, pool house and detached garage with apartment above. Upon entering the main home, the attention to detail is on full display through the intricate millwork, meticulously laid hardwoods, heated Tennessee stone floors, and finely crafted fireplaces. Whether you're working, unwinding, dining or entertaining, this thoughtfully designed home accommodates your needs with unparalleled ease. The provincial kitchen offers professional-grade appliances, a farmhouse sink, and plentiful custom cabinets with granite-topped counters, all chef approved for facilitating the creation of cherished meals. The adjacent dining room, with wet bar, sets the stage for celebrations big and small, while enclosed gazebos and expansive outdoor patios offer perfect settings for gatherings with views of yachts and unforgettable sunsets. At the end of the day, retreat to four bedrooms, each offering perfect accommodations with privacy, and bathrooms adorned with hand-selected stone. The primary bedroom suite boasts, cozy fireplace, spa-like bath and tranquil sunroom overlooking the estate with panoramic views of Trippe Creek. The secondary Primary bedroom suite offers over 1000 sqft of comfy respite, fireplace, and bay window. Guests will appreciate the added option of the two-bedroom guest house and fully independent over-garage apartment. Embrace the outdoors by lounging around the saltwater pool and the pool house with conveniently located kitchen and bathroom, perfect for summer relaxation. And don't forget to explore the 2 private ponds including one with serene island only accessible by a charming footbridge , the caretaker cottage, boathouse, three-car garage, and two barns. The deep-water dock beckons you to launch cruises to discover endless watershed adventures in the surrounding coves, rivers, and sanctuaries that cater to the boating enthusiast or spend the day exploring nearby historic townships like Oxford and Easton, with their plethora of restaurants, golf courses, artful shops, and annual festivals. This exceptional property invites you to experience a lifestyle where refined living seamlessly merges with coastal tranquility. Welcome Home!

5808 Widgeon Point Ln, Oxford

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

$2,595,000
3 Beds 4 Baths
Originally built in the late 1800s, this home was totally and beautifully renovated in the 1990s. With amazing sunset views over the Tred Avon River, this beautiful 3 bedroom home has 4 fireplaces, elevator, carport, swimming pool, and garage. The custom moldings and attention to detail in design are incredible. The architectural elements are reminiscent of a London Row house with very high ceilings, tall windows, significant moldings, and wide plank floors. A butternut paneled study with a hidden room, stenciled wood floors, and a hand painted mural in the entryway present images of the Eastern Shore to visitors. Large windows in all rooms allow a bright and happy feeling, yet all very sophisticated. This home truly has to be seen to be appreciated.

212 S Morris St, Oxford

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

$4,250,000
Talbot County Farm For Sale – Over 200 acres located between Easton and Oxford at the headwaters of Trippe Creek. ‘Piney Point’s Advantage’ provides 214 acres with agricultural fields, mature woodland, extensive habitat for waterfowl, and upland game along with a recorded four-lot subdivision and eight remaining development rights. Habitat and wetlands restoration began in 2011 with a Soil Conservation and Water Quality Plan. The CRP contracts were renewed in 2020 to help with the sustainable use and sound management of soil, water, and habitat resources. Of the 214 acres of the farm, 58 acres are enrolled in the CRP program, 93 acres are under cultivation and the remainder is woodland, field edges, and waterfront. The farm provides an opportunity for residential use with a recorded four-lot division and eight remaining development rights. Development activity is subject to a re-evaluation by the County Health Department for the four existing perc sites. There is an existing private road built to county standards and governing documents in place satisfying county requirements when development activity begins. Located between Easton and Oxford, Piney Point’s Advantage is impeccably well-kept and maintained to maximize wildlife habitat. This farm provides a rare opportunity for a family compound in a natural setting with substantial infrastructure. Waterfowl impoundments, a private road, and approvals that generate value through a myriad of uses are in place and represent value for the buyer with a vision in mind. Set among large estates, Piney Point’s Advantage is sure to please the discerning buyer, nature lover, and outdoors enthusiast. Farm current farming lease and CRP contracts. Documents are available upon request. Assumption of CRP Contracts by Buyer at Settlement.

Almshouse Rd, Oxford

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