luxury house with terrace for sale Owings, United States

Historic Portland Manor – Allendale is privately set on 4.5 acres off sought-after Brooks Woods Road, surrounded by mature trees, neighboring acreage, and pastoral surroundings. A heritage tree-lined drive leads to the residence, framed by established landscaping, gorgeous brick walkways surrounding the home, landscape lighting, covered porches, and a renovated in-ground pool. Dating back to the late 1700s, with additions completed in the early 1800s, the home has been thoughtfully restored and updated while preserving its historic integrity and original craftsmanship. Offering an estimated 5,060 square feet, the property includes six bedrooms and four and a half baths across the main residence and separate in-law suite. Interior features include original heart pine flooring, restored historic windows, six fireplaces, a traditional central hall layout, three staircases, multiple gathering spaces, and extensive custom built-ins and storage throughout. The main level includes a formal dining room with marble fireplace and adjoining butler’s pantry, family room with restored marble fireplace, living room with fireplace and custom built-ins, greenhouse room, powder room, and multiple access points to the home’s covered porches and outdoor living spaces. The custom kitchen features extensive handmade cabinetry and tile work, custom shelving and pantry storage, soapstone and butcher block countertops, commercial-grade gas cooking with a double gas range, vent hood, griddle, separate service sink, and generous preparation space designed for entertaining and everyday functionality. A storage closet beneath the main staircase and extensive built-in cabinetry throughout the connecting gallery to the in-law suite provide exceptional functional storage rarely found in historic homes. The second level includes the primary suite with a large walk-in closet, private kitchenette, fireplace, and ensuite bath. Two additional bedrooms are located on this level, each featuring fireplaces, with one offering an ensuite bathroom. The third floor offers two additional bedrooms, a full bathroom, a large finished storage closet, and expansive attic storage space. The separate in-law suite, originally constructed in 1785, includes a living and dining area, kitchenette, full bathroom with private laundry, and an upper-level bedroom with vaulted A-frame ceiling. The residence includes eight exterior doors leading to approximately 1,000 square feet of covered brick porches, landscaped walkways, pool areas, and outdoor gathering spaces, creating a seamless connection between the home and grounds. Additional upgrades include fresh exterior paint on the entire home (2026), high-efficiency foam insulation in the attic, roof space, and crawlspace, and a comprehensive exterior restoration. The siding was removed and rebuilt with new Rockwool sidewall insulation, plywood sheathing, and infiltration fabric. Outdoor features include a fully renovated 20’ x 40’ pool (2025), pool house, custom fire pit patio with built-in seating, large deck with new decking (2025), fenced areas, extensive landscape lighting, and a custom Williamsburg-style chicken coop. Major system updates include two high-efficiency HVAC systems, plumbing system replaced in 2013, electrical systems and new 400-amp electric service was redone (2025). The exterior was fully repainted in 2026. A rare offering combining historic character, extensive restoration, privacy, acreage, and modern livability, conveniently located near The Cannon Club, local farmers markets, waterfront dining, and commuter routes. Two Tax IDs convey.

A true Chesapeake treasure! Set within the historic Camp Roosevelt community, once home to one of the nation’s earliest permanent Boy Scout camps, this extraordinary 20-acre estate offers approximately 500 feet of private Chesapeake Bay shoreline - and a beach where fossilized shark teeth and other prehistoric treasures are routinely discovered. It is a rare opportunity to own a property where history, nature, and exceptional waterfront living converge. As you approach the home, you are greeted by a spectacular tree-lined private drive culminating in a grand circular arrival court. The stately Georgian Colonial residence is as welcoming as it is impressive. Built in 1999 and thoughtfully designed for a large family, the home offers 5 bedrooms, 5 full and 1 half baths, with an effortless flow between grand entertaining spaces and comfortable everyday living. A dramatic foyer with sweeping circular staircase opens to a gallery and handsome library with two gas fireplaces, billiards, and views toward the water. Above, the second-level library is open to the room below, creating an extraordinary architectural focal point. The two-story great room anchors the rear of the home, where soaring ceilings, a magnificent chandelier, and walls of windows frame expansive views of the grounds and Chesapeake Bay. Four fireplaces throughout the residence add warmth and character to its gracious living spaces. The heart of the home is its exceptional kitchen, designed for gathering and entertaining with a substantial island, Sub-Zero refrigerator, professional propane range, two dishwashers, walk-in pantry, and adjoining wet bar. The adjacent family room/dining area features vaulted, beamed ceilings and remarkable details that pay homage to the property's storied past, including a historic canoe and a one-of-a-kind custom fireplace hearth carved with the Maryland State Seal. The main-level primary suite is a private retreat, complete with two large walk-in closets and two separate spa-like bathrooms, each with its own vanity, shower, soaking tub, and private water closet. Upstairs are three additional bedrooms, including a private waterside ensuite, two bedrooms connected by a shared bath, a gym, generous storage, and access to the open second-level library. An additional bedroom and full bath above the garage provide exceptional flexibility for guests or extended family. Outside, established gardens, extensive hardscape, custom landscape lighting, built-in firepit, spa and a heated in-ground pool with auto-cover create an extraordinary setting for Chesapeake summers and year-round gatherings. From the pool and grounds, hardscape steps with continuous railing lead down to the private beach and 500 feet of shoreline. The unfinished lower level, with bath rough-in, offers additional potential for the next generation to make their own. More than a grand waterfront estate, this is a home designed for living - gathering family, entertaining friends, celebrating milestones, and creating a lifetime of memories. A truly singular Chesapeake Bay property where timeless architecture, remarkable acreage, living history, and one of Maryland's most extraordinary natural settings come together. Yet remarkably convenient, the property is approximately 45 minutes from Washington, DC and just minutes from the restaurants, shops, and waterfront amenities of Chesapeake Beach. Welcome Home!

Build your own piece of the Chesapeake Bay lifestyle in Turkey Point. This lot offers water views across the Chesapeake Bay, South River, and Ramsey Bay, creating a beautiful setting for a future home. Surrounded by water, Turkey Point offers multiple community beach access points, a community pier, and Cloud Field, a large community play and recreation area. Boating, fishing, crabbing, kayaking, paddleboarding, and days along the shoreline are all part of what makes this peninsula such a special place. This lot is being offered for sale with the adjacent lot at 3727 Ramsey Drive, providing the opportunity to own two neighboring parcels and create a larger footprint.

For the first time in decades, this one of a kind property on Turkey Point Island is being offered for sale by the original owners. With exceptional water views and access to the community’s many waterfront amenities, the home has been meticulously maintained and offers just over 2,900 square feet of finished living space across three levels. The main level offers a kitchen equipped with Bosch stainless steel appliances, dining room, bonus sitting room, an expansive living room with custom built ins, surround sound system, and a gas fireplace. Andersen windows are found throughout most of the home, along with hardwood flooring in many of the main living areas. Just off the living room is an incredible screened in porch with water views and opens to the rear deck.  The deck (with fiberon composite deck boards) connects directly to the 24 foot round, 52 inch deep above ground pool, with additional water views from the deck and pool area. Additional storage can be found under the deck as well. Upstairs, you’ll find three bedrooms and two full baths. The primary suite includes an enhanced en suite bathroom and additional closet space. The finished walkout lower level provides another spacious gathering area with a family room and propane fireplace, along with a bedroom, full bath with stand up shower, and laundry. Direct walkout access leads to a private patio and backyard.  An oversized attached two-car garage with roughly 9' wide x 8' high garage doors provides significant and surprising additional storage and has been meticulously maintained. The property also includes a covered front porch, backyard shed and rear fenced in yard. The roof was replaced in 2016, the water heater in 2017, and the home is heated by a heat pump with oil backup. Life in Turkey Point is centered around the water. The community offers multiple beaches and water access points, a pier, walking paths, and Cloud Field with its playground and open green space. Boating, kayaking, paddleboarding, fishing, and crabbing are all part of the lifestyle here, with several marinas nearby and additional access to the Chesapeake Bay at Mayo Beach Park and Beverly Triton Nature Park. And while Turkey Point feels tucked away at the end of the peninsula, everyday shopping, restaurants, and the conveniences of Edgewater are still within easy reach, with Annapolis just beyond.  With water views, four bedrooms, three full and one half bathrooms, a finished walkout lower level, pool, and oversized two-car garage, 1117 Wilson Drive offers substantial living space and storage space with access to everything that makes Turkey Point such a distinctive Chesapeake Bay community. Island living at its best!

Price reduced SIGNIFICANTLY!! 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.

Price Improvement! Motivated sellers. Amazing opportunity to be on the water in Talbot County. Waterfront home situated on Back Creek in Sherwood. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed lighting. The kitchen is equipped with stainless steel appliances, a built-in pantry, and granite countertops. The open floor plan incorporates a gas fireplace and a formal dining room. The primary suite has a walk-in shower, soaking tub, and walk-in closet. An attached three-car garage provides additional space with an upstairs bonus game/theatre room. The backyard is built for fun with a swimming pool, an outdoor kitchen with bar area, gas fire features, a hot tub, and a pool house for storage and a half bath. The property also includes a 30x30 pole building with concrete floors, as well as a dock. New septic installed in 2025!

This over 5000 finished sq. ft. (public records is incorrect in Sq. Ft. listed) Dutch Craftsman with gorgeous front porch (10x43) welcomes you to this private 2 acre lot that is an entertainers dream. It has so many custom features and amenities you will be blown away. The main level is very open concept with bright kitchen with new leather granite and black stainless appliances, soaring ceilings in the huge great room with fireplace and oversized windows and the formal dining room is perfect for those huge dinner parties. The main level also offers a large owners suite and large private deck. New hardwood floors throughout kitchen, great room, foyer and dining room. The upper level has a very cool loft area overlooking great room, three large bedrooms and 2 full baths and a very large 2nd family room over the garage that is perfect for a huge home office or extra living space. But just wait until you see this lower level. Only one word describes it, WOW! It has tons of entertaining space with a custom wet bar, billiards area, theater room, cozy sitting area with pellet stove, guest room, full bath and workout/storage room. This lower level leads to my absolute favorite part, a custom patio/hot tub/ sauna and party space. This area even has its own full bath. It's really quite spectacular. Freshly painted throughout most of the home it is so fresh and ready for its new owners. The private lot at the end of a long driveway is rolling and beautiful with several flowering weeping willows, magnolias, dogwoods, rose bushes and more. This home also features a 2 car side entry garage and oversized driveway for many cars. Easy access to Rt. 50 but feels like you are in the country. 25min to BWI, DCA and 10 min to Annapolis.

Set on a spectacular point of land where the South River meets the Chesapeake Bay, this extraordinary waterfront estate captures some of the most breathtaking views in Annapolis. With coveted southern exposure, the property is immersed in sunlight from dawn to dusk, creating an ever-changing backdrop of sparkling water, passing sailboats, and panoramic Chesapeake vistas. Completely reimagined in 2017 by renowned architect Cathy Purple Cherry, this residence was rebuilt and renovated to an exceptional standard, blending timeless coastal architecture with modern luxury and uncompromising construction quality. Spray-foam insulated walls and roof, steel reinforcement, double plywood construction, four-zone HVAC with humidifiers, gas backup heat, tankless propane water heaters, water treatment systems, generator backup, Sonos audio, and Lutron lighting create a home that is as efficient and functional as it is beautiful. Designed for both grand-scale entertaining and comfortable everyday living, the interior offers over-the-top craftsmanship and thoughtful details throughout. Maple hardwood flooring flows through elegant yet inviting spaces including a dramatic waterfront living room with a custom wet bar, an informal gathering room with built-in bookshelves, a private office with custom cabinetry, wet bar, balcony, and commanding views stretching down the Chesapeake Bay, and a state-of-the-art theater room complete with its own wet bar, refrigerator, and ice maker. The chef’s kitchen is a masterpiece featuring double Wolf ovens, Wolf cooktop, Sub-Zero refrigerator, three dishwashers, wine cooler, ice maker, built-in microwave, instant hot water, walk-in pantry with custom built-ins, and a sun-filled breakfast nook overlooking the water. The luxurious primary suite serves as a private waterfront retreat, highlighted by a stunning spa bath finished with Italian water-cut marble. Three additional bedrooms feature ensuite baths, while a full bath on the main level conveniently serves the pool and outdoor entertaining areas. Outdoor living rivals the finest resorts. Expansive Ipe decking surrounds a heated PebbleTec pool and spa, complemented by an outdoor kitchen, fire pit, integrated sound system, and extensive landscape lighting. The private pier is equipped with water, electric, approximately 4 feet of MLW, a 12,000-pound boat lift, an 8,500-pound boat lift, and a 1,500-pound personal watercraft lift, providing immediate access to the Chesapeake Bay and beyond. Offering 4 bedrooms, 5 full baths, 1 half bath, a dedicated office, and a deep four-car garage, this is a rare opportunity to own one of Annapolis’ premier waterfront properties in a setting where extraordinary architecture, unmatched craftsmanship, and world-class outdoor living come together on the shores of the Chesapeake.

An extraordinary expression of waterfront luxury, this architecturally significant estate represents a rare convergence of world class design, craftsmanship, and lifestyle. Located within the prestigious enclave of Wimbledon Farms, surrounded by grand estates and moments from local vineyards and equestrian facilities, the residence was masterfully conceived by acclaimed architect Scarlett Breeding and flawlessly built by Pyramid Builders. A complete refit elevated the home to an uncompromising standard where timeless architecture and modern sophistication exist in perfect harmony. An enchanting winding crushed gravel driveway framed by Belgian block curbing sets the tone for the remarkable experience that awaits. Perfectly positioned with western exposure, the property captures breathtaking sunsets as golden light melts into the horizon across the river and the surrounding landscape. Professionally designed landscaping creates a lush resort like setting that enhances the home’s striking architectural presence. Inside, high lacquered woodwork, bespoke millwork, hidden passage doors, attention to detail, and coffered ceilings create an atmosphere of refined sophistication. Ultra luxe Chesneys fireplace surrounds anchor multiple living spaces with warmth and elegance, while expansive walls of glass frame sweeping water views and seamlessly connect the indoors with the surrounding waterfront setting. A richly appointed wood-clad office with custom built ins offers an executive retreat designed for both privacy and inspiration. At the heart of the residence, the extraordinary St. Charles kitchen rivals those found in internationally celebrated estates, featuring Premier custom cabinetry, a statement Le Cornue range and island, exquisite fixtures, and an artisan-crafted focal point range hood, all designed for elevated entertaining and effortless daily living. Outdoor living reaches resort caliber with an elevated spa and a spectacular four sided overflow vanishing edge pool, where the waterline sits flush with the pool edge, creating a seamless visual connection to the river beyond. Exotic Ipe hardwood decking surrounds the pool and expansive rear terrace, while pergolas and a screened porch provide beautifully designed spaces for entertaining and relaxation. A new private pier, private beach, and panoramic river and pond views complete this extraordinary waterfront lifestyle. The upper level offers four luxurious ensuite bedrooms, including a phenomenal primary suite with sweeping water views, barrel ceiling, a fireside sitting room, a boutique inspired dressing gallery, and a spa quality bath with a soaking tub overlooking the water. Integrated Control4 home automation delivers effortless comfort and convenience throughout. Tucked away on the coveted Annapolis Neck peninsula, Wimbledon Farms offers a rare blend of tranquility, exclusivity, and convenience. Just moments from Downtown Annapolis and major commuter routes, the setting feels worlds away, defined by peaceful surroundings and an unmistakable sense of retreat. Encompassing only 19 estate homesites, this intimate waterfront enclave is gracefully bordered by Harness Creek and the South River, creating a breathtaking backdrop for both sunrise and sunset vistas. Residents enjoy a warm yet private community atmosphere, highlighted by occasional neighborhood gatherings and an expansive marina on protected Harness Creek, a prized deep water haven known for its calm, sheltered waters and exceptional boating access. Welcome Home!

Highest and best offers are due Tuesday 11/3 at 4pm. Investor Opportunity in White Oak Village. Set toward the end of the street, this Colonial offers three bedrooms, two and a half baths and offers a fenced in backyard currently backing to woods. Offering plenty of room to enjoy the outdoors. The Waldorf location offers quick access to Route 301 and Route 5, plus nearby shopping and dining. The original two car garage was converted to finished space by a prior tenant. Buyer to verify permits and condition. The home has been rented for about 10 years, with lease history available to qualified buyers. Sold as is.

Coastal charm and thoughtful craftsmanship come together in this beautifully renovated cottage in the sought-after Edgewater Beach community. Surrounded by mature trees, perfectly sited on a double lot and filled with natural light, the home offers a peaceful, private setting with seasonal glimpses of Beards Creek and conveniently located access path leading to the water’s edge. Inside, an open floor plan creates an inviting sense of space, enhanced by skylights and a classic brick fireplace with glass doors that adds warmth and character to the main living area. The beautifully renovated kitchen is both stylish and exceptionally functional, showcasing quality craftsmanship and thoughtful details throughout. A distinctive 12' long Bubinga wood live-edge countertop anchors the generous island with abundant seating, while two wall ovens, a built-in pantry, microwave, and ample storage make the space equally suited for everyday living and entertaining. Just outside the main living space, an expansive deck extends the home outdoors, creating a natural setting for dining, entertaining, or simply relaxing beneath the surrounding tree canopy. The seamless connection between indoors and out adds to the home’s relaxed feel and provides a peaceful backdrop throughout the seasons. Two bedrooms are located on the main level, one currently styled as an office, and share a beautifully renovated hall bath. Upstairs, the entire level is dedicated to a spacious and private primary suite. Tucked away from the main living spaces, this serene retreat features a walk-in closet and spa-like ensuite bath with a freestanding jetted tub and separate walk-in shower, creating a wonderful sense of privacy and escape. Located right at the edge of the property a serene path winds through the trees to the shoreline providing a wonderful spot to sit at the water's edge or launch a kayak. The Edgewater Beach community offers a boat ramp, boat slips, kayak storage, pavilion, playground, and additional amenities that make enjoying the South River lifestyle easy. Charming, beautifully updated, and rich with character, this special cottage combines thoughtful renovations, inviting indoor/outdoor living, privacy, and community water access in a peaceful coastal setting. Welcome Home!

Experience the best of Annapolis living in the sought-after, amenities-rich community of Fishing Creek Farm. Perfectly positioned to capture beautiful water views and surrounded by lush lawns and mature landscaping, this handsome brick-front Colonial offers a rare combination of timeless architecture, flexible living spaces, and an exceptional neighborhood lifestyle. A gracious foyer welcomes you into formal living and dining rooms designed for entertaining. At the heart of the home, the bright white kitchen features quartz countertops, abundant cabinetry, and a sunny breakfast nook that flows seamlessly into the impressive family room with soaring vaulted ceilings, a fireplace, and easy access to the patio and expansive backyard. Whether hosting summer gatherings or enjoying a quiet evening outdoors, the spacious front and rear yards provide room to relax, play, and take in the peaceful surroundings. Designed for both convenience and versatility, the main level includes a spacious primary suite, while a second upper-level primary suite enjoys sweeping water views and creates an ideal retreat for owners or guests. Two additional bedrooms share a well-appointed hall bath, providing ample space for family and friends. The partially finished lower level offers additional living space, generous storage, and easily accessible crawl spaces. Life in Fishing Creek Farm extends far beyond the property itself. Residents enjoy one of Annapolis' most coveted waterfront communities, complete with a community marina, swimming pool, sandy beach, tennis and pickleball courts, and year-round social activities. Located on the Annapolis Neck peninsula between the South River and the Chesapeake Bay, this special neighborhood offers a peaceful waterfront setting just minutes from downtown Annapolis, Eastport, and major commuting routes to Baltimore, BWI Airport, Fort Meade/NSA, Washington, D.C., and the Eastern Shore. A wonderful opportunity to enjoy the Chesapeake lifestyle in one of Annapolis' most desirable communities. Welcome Home!

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.

"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. The 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.

"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.

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.

Welcome to 9604 Weshire Drive, a stunning brand-new townhome tucked away in the sought-after Westphalia Row community. Built in 2023 as part of the community’s most recent delivery phase, this meticulously maintained residence offers three bedrooms, three and a half bathrooms, an attached two-car garage, and over 2,000 square feet of thoughtfully designed living space across four levels. The heart of the home is the main level’s open-concept layout, anchored by a gourmet kitchen featuring quartz countertops, shaker cabinetry, a stainless steel appliance package, and an oversized island perfect for entertaining. The adjacent dining area flows seamlessly into a generous living room with a built-in gas fireplace and direct access to a serene walk-out balcony. A convenient powder room completes this level. Upstairs, the spacious primary suite serves as a true retreat, complete with a spa-inspired en-suite bath featuring a double vanity and soaking tub. A third-floor family room provides additional flexible living space alongside a private guest suite with its own en-suite bathroom and walk-in closet. The third level exits to a private rooftop terrace, where sweeping views of the Maryland hills and lush tree canopies await, an ideal setting for morning coffee or evening entertaining. Ownership in the Westphalia Row community provides access to the Westphalia Clubhouse with a fully outfitted fitness center, entertainment spaces, children’s playground, and a dog park. This community is conveniently located within easy access to major commuter thoroughfares including I-495 and is only an 8-minute drive to Downtown Largo Metro Station (Blue/Silver). Kettering Plaza with all your essentials including Giant, Target, Lowes, Staples and a number of dining options is just a 7-minute drive. Step into your new home today! ***This property qualifies for $10,000 welcome home grant or a 0% down payment program with additional $5,000 grant for qualified buyers***

South River Waterfront! Discover an exceptional waterfront lifestyle in Port Isle, where beautiful water views, a private pier, and thoughtfully designed indoor and outdoor spaces come together in a setting made for boating, entertaining, and relaxed everyday living. A cart path through the backyard leads to the private pier, complete with low-maintenance composite decking, a 24,000-lb. boat lift, and floating dock offering effortless access for kayaks and paddleboards. A long driveway creates a sense of arrival and leads to the two-car garage. Inside, the light-filled foyer with vaulted ceiling opens to a comfortable living area before flowing into the heart of the home. The expansive kitchen is designed for gathering, with two generous islands, abundant cabinetry, and extensive counter space providing exceptional room for cooking and entertaining. An adjoining dining area connects seamlessly to the family room, where a fireplace anchors the space and doors open to the waterfront deck. Here, elevated views across the backyard toward the South River create a natural extension of the living space and an inviting backdrop for dining, entertaining, or simply unwinding at the end of the day. Upstairs, all three bedrooms feature vaulted ceilings and water views. The primary suite is a peaceful retreat with a private waterfront balcony and ensuite bath featuring dual sinks and a spacious walk-in shower with bench. Two additional bedrooms share a well-appointed hall bath with dual sinks. A conveniently located laundry room completes this level. The walk-out lower level expands the home's versatility with a spacious recreation room, fourth bedroom, full bath, and generous storage. The living area opens to an extensive screened porch overlooking the backyard and water, creating another exceptional space for entertaining and relaxing. Seasonal coverings allow the porch to be enjoyed well into the cooler months. With multiple outdoor living spaces, a private pier, boat lift, kayak launch, and direct access to the South River, every element invites you to embrace life on the water. A golf cart conveys with the property, making it easy to travel through the neighborhood and down to the water's edge. Whether heading out for a day of boating, launching a kayak, entertaining on the deck, or relaxing on the private balcony, this Port Isle waterfront retreat captures the ease and beauty of the waterfront lifestyle. Welcome Home!

Experience the Annapolis waterfront lifestyle from this charming A-frame cottage, where days on the water begin just steps from your door. Designed for relaxed coastal living, the 2-bedroom, 2-bath home features a light-filled, open interior with soaring vaulted ceilings and an inviting sense of space. Outside, the property becomes your private gateway to the South River. A private pier offers two deep-water slips, including one with a boat lift, while a dedicated kayak launch makes it effortless to explore the surrounding waterways. Bulkheaded shoreline, a storage shed, and ample outdoor space complete a setting designed for life along the Annapolis waterfront. Spend mornings enjoying coffee overlooking the water, afternoons boating, kayaking, or paddleboarding, and evenings unwinding on the South River as the sun sets across the waterfront. Whether you're searching for a full-time residence, weekend retreat, or Annapolis boating getaway, this is an opportunity to embrace a lifestyle centered around the Chesapeake Bay

Just 12 miles from St Michaels, this house is in a quiet community of 60+ homes at the end of a lovely peninsula. A public landing is at the end of Bozman Neavitt Road, and a community center and park are in the heart of the village. This historic home was built by members of the Neavitt family, for who the village was named. The present owner bought it in 1999 and renovated and updated it from the studs out. Features now include 2-3 Bedrooms 2 Full baths Living room with built-ins Light-filled kitchen with cathedral ceiling Large landscaped lot with patio Some furniture conveys

Unbelievable price reduction! Located about 12 miles from St Michaels, Neavitt is a charming village of 60+ houses at the end of a peninsula. The village has a park and playground, public landing with a launch for canoes, and an active community association that stages events and operates its own lending library. 6403 was renovated and expanded in 2011 and the layout adapted for modern living, with light-filled rooms, a cleverly updated floor plan, and direct views of Balls Creek. Features include a skylit first floor primary suite, spacious great room, an eat-in kitchen with Kraftmaid cabinets...but no St Michaels taxes! The two adjacent properties are being renovated. Each will be valued at over $900,000 when completed!

Why wait to build when you can move right in? Welcome to 126 Stilly Way, a beautifully finished, nearly new home in Annapolis’ Parkside Preserve. Built in 2024 and offering more than 4,400 square feet of finished living space across three levels, this home combines the appeal of newer construction with the convenience of having the finishing touches already in place. The bright, open main level features a beautifully appointed kitchen with white cabinetry, quartz countertops, stainless steel appliances, gas cooking, double wall ovens, tiled backsplash, and an oversized center island. The kitchen flows seamlessly into the spacious family room, anchored by a gas fireplace with custom built-ins. A separate dining room provides additional space for entertaining. Upstairs, the primary suite features a tray ceiling, walk-in closets, and private bath with dual vanities, soaking tub, and oversized glass-enclosed shower. Three additional bedrooms each with their own walk-in closets and well-appointed baths complete the upper level. The finished lower level adds exceptional flexibility, with an expansive recreation area, wet bar with beverage refrigerator, full bath, and the potential to create a true fifth bedroom while still maintaining plenty of additional living and entertaining space. What truly sets this home apart is how much has already been done. Window treatments are installed, the lower level is finished, the yard is established, and the home is ready to enjoy from day one. Enjoy the benefits of a newer home without waiting on a construction timeline or tackling the many finishing touches that often come after settlement. A covered front porch, HardiePlank and brick exterior, level backyard, and attached two-car garage complete the property. Located just moments from Quiet Waters Park and convenient to Downtown Annapolis, shopping, dining, and major commuter routes, 126 Stilly Way offers the opportunity to enjoy newer construction with the added benefit of a home that is already finished, established, and truly move-in ready.

Welcome to 2820 Pennypond Lane, an end-of-row townhome ideally positioned within the sought-after community of Riva Trace. Backing to a peaceful wooded setting, this special home offers a wonderful sense of privacy and tranquility while providing all the conveniences of a vibrant Annapolis community. With three levels of thoughtfully designed living space, this home has been freshly painted throughout and features brand-new flooring on all three levels, creating a fresh, inviting feel from the moment you step inside.The main level welcomes you with an open, light-filled layout enhanced by vaulted ceilings, recessed lighting, and a spacious living and dining area. A wood-burning fireplace creates a cozy focal point, perfect for relaxing on cooler evenings. The kitchen features updated cabinetry, stainless steel appliances, and skylights that bring in an abundance of natural light. Both the kitchen and living room offer direct access to the expansive rear deck, an ideal setting for morning coffee, outdoor dining, or entertaining while enjoying the peaceful wooded backdrop. Designed with convenience in mind, the main level also features a spacious primary suite with vaulted ceilings, large windows, a walk-in closet, and an ensuite bath complete with double vanity and walk-in shower. A convenient powder room completes this level. Upstairs, two additional generously sized bedrooms share a full bath, providing comfortable accommodations for family, guests, or a home office. The lower level offers even more versatile living space, complete with a wet bar and half bath, making it a wonderful spot for entertaining, relaxing, or creating a separate recreation area. Additionally, an unfinished area provides excellent storage and room for hobbies or workspace. An attached garage with an EV charger adds another layer of convenience to this thoughtfully appointed home. Riva Trace offers a lifestyle that blends outdoor recreation with everyday convenience. Residents enjoy access to a private pier perfect for kayaking and paddle boarding, along with tennis and basketball courts and scenic walking trails. Conveniently located just minutes from Annapolis Towne Centre, local restaurants, shopping, and major commuter routes including I-97 and Route 50, this location makes it easy to enjoy everything the area has to offer.

Life along Broad Creek unfolds at a different pace, where peaceful waters, wooded surroundings, and the ever-changing beauty of the seasons create an extraordinary setting for a truly distinctive home. This remarkable Acorn Deck home has been comprehensively transformed with over $875,000 in improvements by renowned builder GYC Group. Thoughtfully enhanced and updated throughout for effortless modern living, the home beautifully preserves its architectural character while introducing sophisticated finishes and modern conveniences. Soaring wood ceilings, exposed beams, dramatic walls of glass, and sweeping water views create an unforgettable connection to the surrounding landscape. Adding to its appeal is the rare trifecta of public water, public sewer, and natural gas, providing an added measure of peace of mind and ease to everyday living. At the heart of the residence, a spectacular two-story glass solarium brings the outdoors in, offering a stunning setting to appreciate the changing seasons. Warm wood finishes and abundant natural light carry throughout the inviting living spaces, including a beautifully appointed family room with a striking fireplace and custom built-ins. The completely redesigned kitchen features quartz countertops, an expansive island, custom cabinetry, and a welcoming breakfast area, creating an effortless flow for everyday living and entertaining. An elegant dining room provides another inviting gathering space. The upper-level primary suite is a peaceful sanctuary featuring vaulted wood ceilings, expansive windows framing the water, a private balcony, and a beautifully renovated spa-inspired bath with a freestanding soaking tub and walk-in shower. Additional bedrooms offer comfortable accommodations for family and guests, while the lower-level recreation room with wet bar opens to a private patio. Outside, multiple decks and patios invite you to experience waterfront living from every perspective. Morning coffee overlooking the creek, afternoon gatherings surrounded by nature, and evenings watching the sunset become part of the everyday experience. A private tram provides convenient access to approximately 60 feet of shoreline and a 70-foot long deep-water pier with approximately 10 feet MLW, two boat slips, two boat lifts, two jet ski lifts and waterfront shed, an exceptional setting for boating enthusiasts. Extensive improvements to the home's interior, exterior, and landscaping complement its remarkable transformation. Offering four bedrooms, three full baths, a powder room, and 2 car garage, this extraordinary property captures the essence of waterfront living, where architectural beauty, thoughtful enhancements, and endless adventures on the water come together. Conveniently located in the coveted Broadview Estates community with easy access to Riva Road quickly leading to shopping, restaurants and commuter roads. Welcome Home!