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$12,500,000
7 Beds ⋅ 13 Baths
THE FRIARY a Trophy property in a league of its own! Set on 23 private acres overlooking a gracious bend of the Severn River with 1,500ft of prime waterfrontage, just minutes from downtown Annapolis and less than an hour from the nation's capital, lies one of the most distinctive estates offered for sale on the East Coast. A true architectural masterpiece, this exquisite 35,000+ sqft residence, is the result of a mammoth and complex renovation that brought it back to its classic Georgian style yet with an acknowledgment of the owner's contemporary tastes and interests. Formerly a Capuchin monastery, this stately brick structure offers modern amenities for comfortable family living yet easily accommodates elegant grand scale entertainment and private events. The attention to detail and emphasis on proportions and craftsmanship are unparalleled. The exterior features spectacular 270 degree river views, nine car garage, roof garden, pool pavilion, 60 feet infinity edge pool, tennis court and direct access by funicular to a 6 slip private dock with 10' MLW and boat lift. Step into the main core of the home, where 18th-century elements, like original heart pine floors & foyer arch moldings, have been flawlessly preserved. A cleverly designed limestone rotunda containing a conservatory & atrium lead to either of the house’s wings: the impeccably appointed guest wing with spacious common room, or the chapel-turned-ballroom with sweeping limestone fireplace, herringbone teak floors, & arched double doors with a picturesque terrace beyond. The extraordinary estate contains a total of seven bedrooms, eight bathrooms and eighteen fireplaces, formal dining room and formal parlor, commercial size gourmet kitchen, over sized ballroom, conservatory, family room, library, music room, indoor spa, game room, wine cellar, catering kitchen, work shop, and a secret vault. Additional structures on the property include a three bedroom, two bath-guest/staff house, an Asian tea house and mechanical facilities. Only minutes from Washington D.C. and multiple international airports, this elegant and opulent property is worlds away from the hustle and bustle of everyday life yet offers an easy commute to several major metropolitan cities. Unmatched opulence and privacy awaits on the Severn River!

1604 Winchester Rd, Annapolis

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

Selling Office: Unrepresented Buyer Office.

$1,415,000
4 Beds ⋅ 5 Baths
Welcome to 42 Ridgeview Way, a beautifully maintained Tyler model set on 3.32 acres in one of Upper Freehold’s most sought‑after neighborhoods, backing to peaceful preserved farmland. This home delivers the space, charm, and lifestyle we all love, all just minutes from historic Allentown, scenic walking trails, and a neighborhood pathway that leads directly to the highly rated school campus. A soaring two‑story foyer with wrought‑iron balusters opens to sun-filled rooms designed for both everyday living and effortless entertaining, including formal living and dining rooms and a cathedral family room with a gas fireplace and views of the backyard oasis. A private first-floor office adds the flexibility today’s lifestyle demands. The renovated kitchen features upgraded granite countertops, stainless steel appliances, subway tile backsplash, center‑island seating, and a seamless connection to the mudroom with custom cubbies. Upstairs, the spacious primary suite offers vaulted ceilings, dual walk‑in closets, brand-new carpeting, and a well-appointed bath with a soaking tub, an oversized shower, and dual vanities; two additional bedrooms share a full bath, while the princess suite enjoys its own ensuite. The finished walk‑out lower level expands your living space with areas for recreation, work, fitness, and storage. Outside, your private retreat includes a heated, custom-saltwater Gunite pool, a covered gazebo, multiple patio areas, and a maintenance‑free Trex deck overlooking serene, preserved views. With a three-car garage and a 10 kW generator, this home offers comfort and style in one of Upper Freehold’s most admired communities, conveniently located near major roadways, shopping, and Historic Allentown Borough. A must see!

42 Ridgeview Way, Allentown

Listing courtesy of Keller Williams Premier. Contact:

Selling Office: Smires & Associates.

$1,139,400
5 Beds ⋅ 4 Baths
A Rare Exceptional Retreat in Winchester Estates — Annapolis, MD Welcome to an extraordinary custom-built residence where timeless elegance meets unparalleled serenity. Set on a magnificently landscaped, park-like acre, this 5-bedroom, 4-bath estate offers a level of privacy and tranquility seldom found so close to the heart of downtown Annapolis. Nestled within the prestigious Winchester Estates, this property grants private water-access creating a lifestyle that blends luxury living with the best Annapolis has to offer. Inside, unique design and exceptional craftsmanship define every space. The chef’s kitchen, outfitted for the culinary enthusiast, anchors the main level and opens seamlessly to a grand, light-filled living area—an ideal setting for refined entertaining or intimate gatherings. Expansive windows invite the lush landscape indoors, enhancing the home’s natural harmony and sense of calm. The elegant lower level offers a rare level of versatility, featuring a full private suite with its own bedroom, bathroom, kitchen, dining room, and living room—perfect for multigenerational living, distinguished guest accommodations, or an au pair residence. Outside, the estate’s grounds unfold like a private sanctuary. Mature trees, newly developing gardens, and verdant open spaces create an atmosphere of effortless peace—a truly restorative environment just minutes from world-class dining, boutique shopping, and the historic charm of Annapolis. Highlights Include: * Custom-built architecture on a serene 1+ acre park-like lot * Extensive cutting-edge electronic pet fence system * Exclusive neighborhood water-access privileges * Right next door to the beautiful Baltimore Annapolis Trail Park * Gourmet chef’s kitchen with Blue Star 8 Burner Stove and expansive entertaining areas * Full private lower-level suite with separate living quarters * A Total of Five spacious bedrooms and four well-appointed bathrooms * Two upper level bedrooms have self-contained climate control * Exceptional privacy in one of Annapolis’ most coveted communities * Full Premium Warranty Offered This is more than a home—it is a private retreat offering refined luxury, natural beauty, and an unmatched Annapolis lifestyle.

1635 Winchester Rd, Annapolis

Listing courtesy of Equity Property Investments. Contact:

Selling Office: CENTURY 21 New Millennium.

$390,000
3 Beds ⋅ 2 Baths
Welcome to 113 Collier Road in Grasonville, Maryland—an action-packed rancher situated on an oversized corner lot. This well-maintained home features a fully fenced backyard and clearly reflects pride of ownership inside and out. Offering 3 bedrooms, 2 full baths, and an open floor plan designed for comfortable family living. Enjoy the freedom of NO HOA, with convenient access to shopping, schools, medical facilities, and entertainment. Come experience the Land of Pleasant Living in beautiful Queen Anne’s County.

113 Collier Rd, Grasonville

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

Selling Office: Long & Foster Real Estate, Inc..

$320,000
3 Beds ⋅ 2 Baths
Welcome to this well-kept home on a quiet cul-de-sac, just minutes from Route 50 and about 10 minutes from the Bay Bridge. This freshly painted single-level home offers 3 bedrooms and 2 full baths on nearly a quarter-acre lot. The bathrooms have been recently renovated, and the kitchen features updated cabinets, giving the home a fresh and ready move-in feel. The property also includes a detached 1-car garage. The previous owner began working on it but left it unfinished. Buyers should confirm intended use with local county for permits. With the right vision, there is a lot of potential, or it can be turned back to its original purpose as a garage. A great location, updated features, and future potential make this home one you don’t want to miss!

116 Pine, Grasonville

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

Selling Office: Unrepresented Buyer Office.