luxury house with pool for sale Chester, United States

This is a true coastal retreat, from its stunning exterior to its thoughtfully designed living spaces. A one-of-a-kind waterfront estate, the property offers more than 2,000 feet of shoreline and sits on 5.4 private acres at the end of Kilby Point. Surrounded by water on both the Wye River and Eastern Bay, this exceptional home captures endless panoramic views in every direction. And yes-how many people can say they own a lighthouse? The home has been completely renovated down to the studs, blending timeless coastal charm with modern convenience. Interior features include shiplap walls, beamed ceilings, new flooring, and beautifully reimagined living spaces throughout. The new kitchen is a showpiece, featuring quartz countertops, a large island, and Caf appliances. A sprinkler system has also been added for peace of mind. Designed to maximize its breathtaking setting, the home offers multiple living and entertaining spaces, including a game room, office, and dramatic 360-degree rooms with incredible views of the surrounding water and wildlife. There are four bedrooms, five full baths, and two half baths, all fully renovated with walk-in showers, elegant tile work, and stylish vanities. The primary suite is especially luxurious, featuring separate his-and-hers bathrooms. Outdoor features are just as impressive, with a sand beach, rip-rapped shoreline, private pier with lift and electric, new pool decks, and a private setting that feels both peaceful and extraordinary. Additional upgrades include new siding, rails, septic, and a redesigned garage that has been incorporated into the home's layout with glass doors, creating even more functional living space. If you are searching for a waterfront property that feels truly special-distinctive, private, and unforgettable-this is it.

Enjoy resort-style waterfront living with harbor and Chesapeake Bay views in the gated community of Chesapeake Harbour. This beautifully updated two-level residence offers the ideal blend of comfort, natural light, and low-maintenance coastal living. Freshly painted throughout with new carpet, the home features a thoughtfully designed floor plan with over 1,900 square feet of living space, an attached 2 car garage with interior access and additional parking out front, a rare and coveted amenity in the neighborhood. The entry level features an eat-in kitchen with white cabinets and counters, powder room and laundry room with a few steps up to the living room. The thoughtfully designed split-level layout creates a natural separation between the home’s functional spaces and its main entertaining areas, allowing gatherings to flow effortlessly while keeping day-to-day tasks discreetly tucked away. The dramatic living area where soaring ceilings, gas fireplace with custom built-ins, and walls of windows fill the space with natural light while framing the harbor views. Step outside to the expansive full-width waterside deck, the perfect setting for morning coffee, evening cocktails, or simply enjoying the marina activity and views stretching toward the Chesapeake Bay. Upstairs, the spacious primary suite offers a balcony, an ensuite bath with new cabinet and drawer fronts, and a peaceful retreat for relaxing after a long day. A loft-style flex space overlooks the living room below and can easily function as a second bedroom, home office, or additional lounge area, complemented by a full hall bath. Life in Chesapeake Harbour feels like a year-round vacation with an unmatched collection of resort-style amenities, including two waterfront pools, a private sandy beach, exclusive fitness center for a small enclave of residents, tennis and pickleball courts, fishing piers, walking and jogging paths, picnic areas with grills, scenic Chase Pond, and the security of a 24-hour attended gatehouse. The newly opened waterfront marina restaurant adds to the vibrant atmosphere with outdoor dining and live music on weekends. Ideally located just minutes from Downtown Annapolis, Eastport, the United States Naval Academy, waterfront dining, shopping, and historic attractions, this exceptional residence also offers easy access to Washington, DC, Baltimore, and Baltimore/Washington International Thurgood Marshall Airport. Whether you are searching for a full-time residence or a lock-and-leave waterfront retreat, this home offers the very best of the Annapolis waterfront lifestyle. Welcome Home!

Previous Buyers move from California fell through. Home is back on the market and ready for you! Wake up to panoramic views of the Magothy River from this beautifully updated home in the sought-after waterfront community of Cape St. Claire. Expansive windows fill the home with natural light while showcasing breathtaking water views from many of the primary living spaces. The stunning remodeled kitchen features quartz countertops, stainless steel appliances, custom cabinetry, a dry bar, and an open layout that flows seamlessly into the dining and living areas. Hardwood flooring, beautifully renovated bathrooms, updated stair railings, fresh paint, and designer finishes create a home that is both elegant and inviting. Offering a highly desirable layout with two main-level bedrooms and a private upper-level primary suite, the home provides exceptional flexibility for guests, multigenerational living, or a dedicated home office. The spacious primary retreat features a sitting area, custom walk-in closet, spa-inspired bath, and private balcony overlooking the Magothy River. The finished lower level provides additional flexible living space, abundant storage, and walk-out access to the backyard. Outdoor living shines with an expansive Ipe wood deck with glass railings, a hot tub, beautifully landscaped grounds, and stairs leading toward the shoreline—perfect for entertaining or simply enjoying the ever-changing waterfront scenery. With more than $250,000 invested in improvements over the past four years, this home combines timeless design with modern efficiency. Major updates include a complete kitchen renovation, three remodeled bathrooms, hardwood flooring, dual high-efficiency Carrier HVAC systems, updated electrical service with a Level 2 EV charger, reverse osmosis and whole-house water filtration systems, well pump replacement, waterproofing improvements, custom primary closet, backyard fencing, and much more. Conveniently located just minutes from downtown Annapolis, Broadneck schools, shopping, dining, commuter routes, and the Chesapeake Bay Bridge, this is a rare opportunity to own an extensively updated home with spectacular water views in one of Anne Arundel County's most beloved waterfront communities.

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, with the current living room serving as a billiards room. 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!

***PLEASE READ FOR OPEN HOUSE ON 7/11*** PARK EITHER PAST 182 SEVERN WAY ON THE RIGHT FOR PUBLIC STREET PARKING OR AT THE COMMUNITY BEACH TO WALK ALONG THE COAST TO REACH THE PROPERTY. *** Nestled along Chase Creek in the sought-after Pines on the Severn community, this utterly charming waterfront cottage is the definition of storybook living. Overflowing with character, warmth, and thoughtful updates, 1448 Westway offers the rare combination of cozy cottage appeal and exceptional outdoor-lifestyle amenities, just minutes from Downtown Annapolis and Route 50. Inside, knotty pine walls create a timeless cottage feel, while the exquisitely lit enclosed porch provides the perfect setting for morning coffee, reading, or entertaining year-round. The updated kitchen features granite countertops, upgraded wood cabinetry, recently installed refrigerator, and quality finishes. Additional recent improvements include double-paned, energy-efficient windows, top rated Mitsubishi AC units, and all recently updated lower level doors. Upstairs you will find updated ceilings, carpeting and the addition of a spacious walk-in closet. Bathrooms include updated toilets, charming checkerboard tile flooring, and a recently installed upstairs shower. Step outside to enjoy an exceptional waterfront setting with approximately 75 feet non-riparian waterfront along Chase Creek, one of the highest quality bodies of water in all of the Severn River. The beautifully crafted ipe wooden rear stairway and deck overlook the water and lead down to a stunning stone patio ideal for outdoor entertaining. The outdoor breezeway connects to a large freshly painted basement offering abundant storage, gardening space, and a dedicated kayak/canoe rack. After boating, paddleboarding, or beach days, unwind in the convenient outdoor shower. Property offers BRAND NEW roof and kitchen skylight, refinished kitchen flooring, newly built/stained front deck, repainted enclosed porch flooring, and freshly painted upper level spaces as well as the spacious basement. The basement presents an excellent opportunity for future finishing. Its side and rear entrances, along with an elongated window, add convenience and versatility to the space. Pines on the Severn offers an unmatched lifestyle with community amenities including a sandy beach, boat slips, floating dock, boat ramp, canoe/kayak storage, playground, ball fields, tennis and basketball courts, community pool, and easy access to the B&A Trail. A truly special property blending waterfront charm, community lifestyle, and modern updates in one unforgettable cottage retreat. Deeded 9'x18' parking space on neighboring pad plus readily available on‑street parking around the corner on Severn Way and at the level community beach parking area a short flat walk from the cottage. Special Notes: This property is part of a Special Community Benefits District (SCBD) that transfers $589 annually from paid local taxes to the Pines Community Improvement Association (PCIA) instead of HOA fees.

MOTIVATED SELLER. BRING ALL OFFERS. Two houses for the price of one! 704 Caleb Lane includes an amazing garden apartment, perfect for an in-law or au pair! It is beautifully maintained and loaded with recent updates in the highly sought-after, amenity-rich Kingsport community of Annapolis. The spacious, open floor plan is enhanced by the many value-added updates in the home, including the renovated kitchen, roof (2022), HVAC systems (2025 and 2022), and water heater (2022). The light-filled walk-out lower level is a complete in-law/au pair suite that includes a kitchen, both a full AND a half bath, a 2nd laundry, and not one but two bedrooms! A huge bonus and sheer perfection for guests, multigenerational living, a theater room, or an extended entertaining space. The stunning main-level kitchen is designed to impress, featuring sparkling granite countertops, a massive center island, custom cabinetry, and convenient access via a fun and functional secondary staircase. The kitchen opens seamlessly to the dramatic two-story Great Room, highlighted by a cozy gas fireplace, soaring windows, and elegant custom wood blinds that run throughout the main level. Beautifully maintained hardwood floors run throughout the home, adding warmth and timeless appeal. Outside, the pristine driveway with ample parking and an oversized two-car garage with built-in cabinets and fantastic storage space for gardening, landscaping, and recreational needs. Situated on nearly a quarter-acre lot, the property is the best location in the neighborhood, just two short blocks from the community pool, clubhouse, playgrounds, water access for kayaking and fishing, and scenic walking and biking trails. This exceptional property offers the perfect blend of comfort, elegance, and convenience. Located only 10 minutes from Downtown Annapolis, this home provides the tranquility of private community living without sacrificing easy access to shopping, dining, and waterfront attractions. This elegant home truly checks every box — offering exceptional space, thoughtful upgrades, outstanding community amenities, and an unbeatable Annapolis location.

Perched above the Severn River in the gated waterfront community of Epping Forest, this exceptional property captures sweeping water views and effortless indoor/outdoor living just minutes from downtown Annapolis. Thoughtfully designed with an open floor plan and walls of windows, the home is filled with natural light, high ceilings, custom millwork and seamless sightlines to the Severn river from nearly every vantage point. Expansive ipe decks with sleek cable railing extend the living space outdoors, creating the perfect setting for sunset entertaining or quiet mornings overlooking the water. The primary suite is a true retreat, complete with a private balcony overlooking the Severn; an idyllic perch for enjoying elevated river views and summer breezes. On the lower level, a covered flagstone patio offers an additional outdoor haven, ideal for relaxed evenings, gathering with friends or stepping directly out toward the waterfront. Inside, beautifully appointed gathering spaces flow easily from the gourmet kitchen to the dining and living areas, offering both comfortable everyday living and gracious entertaining. Three spacious bedrooms, three full baths and two half baths are thoughtfully distributed across four finished levels, providing flexibility for guests, work from home needs or additional recreation space. The private pier with deep water and two lifts, including a dedicated jet ski lift, invites endless days on the Severn, with quick access to Annapolis waterways and beyond. Ideally positioned close to Epping Forest’s renowned amenities, residents enjoy a clubhouse with waterside dining, marina, sandy beach, boat ramp, tennis courts, walking trails and a vibrant calendar of social events. An additional 0.115-acre parcel on Sherwood Trail (Tax ID: 224010114205) conveys with the sale and offers convenient supplemental parking, providing easy access for the many guests who will be sure to come visit. A rare opportunity to embrace panoramic river views, exceptional community amenities and the quintessential Annapolitan waterfront lifestyle. Epping Forest is a Special Tax District ($3,059.47 annually) with binding Rules and Regulations. Welcome Home!

Waterfront home with almost an acre tucked along Church Creek, just off the South River, 26 Wilelinor Drive offers a rare blend of convenience, privacy, space, and meaningful waterfront living. Set on nearly an acre (.8642 acres), this property pairs a thoughtfully renovated home with a deeded dock featuring two slips, with the pier resurfaced, one slip offering a floating dock for easy water access and the other recently dredged. Originally built in 1960 and extensively renovated in 2013 and 2015, the home spans four levels with four bedrooms and two and a half bathrooms. Three bedrooms are located on the top floor, with the fourth bedroom and a dedicated office space on the lowest level. The entryway opens into the level featuring a family room and game area, along with access to the back patio. From there, the main living level features an open concept layout centered on a bright kitchen with updated granite countertops, an oversized 62 x 80 island, built-ins, pot filler, gas cooking, and stainless steel appliances. The main living room offers extensive natural light, access to the back patio, and water views. Two fireplaces, one wood stove and one gas, provide additional heat. The backyard is a true extension of the home, with newer hardscaping and extensive landscaping completed over the years, creating a setting that feels more like a private park. The property includes a surround sound system, new drain field (2025), updated gutters and drainage systems, and major mechanical updates including HVAC, water heater (2024), and a whole-house generator with an automatic transfer switch. An oversized two-car garage with a third door for drive-through access to the backyard, a circular driveway, side driveway for additional parking, and a 12' x 18' shed provide storage and parking flexibility. The backyard also includes a compost station and a large kayak rack. The shoreline has been reinforced with new pilings and deadheads. Additional features include smart home hubs (two hubs and a dot) and a programmable thermostat. Wilelinor Estates is one of Edgewater’s most distinctive waterfront communities, quietly set apart, yet minutes to Annapolis. Known for its wide streets, mature trees, and access to Church Creek, the South River, and beyond, the neighborhood offers a waterfront clubhouse, boat slips, a kayak and paddleboard launch and racks, and trails along several ponds. Life here centers around the water, the outdoors, and a sense of space that’s increasingly hard to find.

1486 Downham Market is the ultimate Annapolis deep-water estate-designed for those who demand luxury, security, and boating excellence. Perfectly positioned at the mouth of Clements Creek-one of the safest hurricane holes on the Severn River-this home pairs architectural brilliance with one of the region's most coveted waterfront settings. A commanding 180' pier with three boat slips, 50-amp power, and 11' MLW welcomes yachts and sport boats alike-Hinckley, Viking, Boston Whaler, Pursuit, or Chris-Craft-this property can handle them all. Reinforced pilings are ready for lifts, making this a boater's dream with full riparian rights. From here, you'll be on the Severn and Chesapeake Bay in minutes. Inside, walls of glass frame sweeping water views from nearly every room. Across three levels, the transitional design blends clean lines with warmth: hardwood floors, designer lighting, and soaring ceilings. The chef's kitchen is fully outfitted with commercial-grade appliances, granite counters, and gas cooking, flowing into multiple living and dining areas anchored by a dramatic two-sided stone fireplace. The primary suite is a true retreat-private sitting room and fireplace, a spa bath with skylight, soaking tub, glass shower, and custom walk-in closet. Additional ensuite and Jack-and-Jill bedrooms provide comfort and privacy for family or guests. The walkout lower level is built for entertaining with a rec room, wet bar, wine storage, gym, fifth bedroom, full bath, and a glass-wrapped sunroom ready for a hot tub retreat. Outdoor living is extraordinary: multi-level decks, panoramic views, and serene waters that stretch toward the Severn and Bay. A brand-new septic system and advanced water treatment with reverse osmosis and UV protection offer peace of mind. Set in the prestigious Downs on the Severn, residents enjoy two marinas, clubhouse, pool, tennis and pickleball, and a close-in location to Annapolis, D.C., and Baltimore. Waterfront estates of this caliber almost never hit the market. 1486 Downham Market is ready now-bring your yacht, bring your lifestyle, and claim your place on the Severn.

This extraordinary gated 20-acre waterfront estate, featuring a French-inspired stone residence, sits prominently along the banks of the Severn River just minutes from downtown Annapolis and under an hour from Washington, DC. With coveted western exposure, the property offers breathtaking, year-round sunsets and over 23,000 square feet of combined living space across the main house, guest house, and carriage house-all set amid rolling lawns, formal gardens, mature trees, and natural surroundings. The main residence is designed for both grand entertaining and comfortable living, with ten sets of French doors opening to terraces and gardens. A dramatic two-story foyer with limestone and marble inlays leads to a soaring great room anchored by an 18th-century French carved limestone mantel. Additional main-level spaces include a formal dining room, library, and music room-each with its own fireplace-and a gourmet kitchen featuring dual marble-topped islands. Upstairs, an open gallery overlooks the great room and grounds, while the expansive primary suite offers a fireplace, private sitting room, and waterside balcony with sweeping river views. The lower level is equally impressive, with a family room, billiards room and bar, a striking stone wine cellar with tasting room, media room, full gym with bath and sauna, and an additional bedroom suite. A separate wing provides a dedicated art studio or craft space, complemented by a motor court and two three-car garages. Outdoor living is equally refined, with manicured lawns and gardens, an expansive patio, outdoor kitchen, hot tub, and charming details including a gardening shed, chicken coop, and raised beds. The approximately 6,000-square-foot guest house is ideal for hosting, centered around a pool with a covered veranda, outdoor fireplace, bar, and gazebo-all with water views. Inside, it offers spacious living and dining areas with a shared stone fireplace, three bedrooms, two full and two half baths, and a full catering kitchen with Viking appliances. A breezeway connects to the carriage house with an additional three-car garage. The estate's 900 feet of shoreline is complemented by a 350-foot deep-water pier (8-9' MLW) with four slips, including two accommodating 60-foot vessels, and two boat lifts-perfect for boating, sailing, and enjoying life on the Severn River and Chesapeake Bay.

Set on nearly three private acres overlooking the fifth hole of South River Golf Course, 17 Perder Lane is a stately oversized all-brick manor, offering nearly 10,000 square feet of finished living space in one of Edgewater’s most private and picturesque settings. Designed for a life centered on comfort, recreation, wellness, and entertaining, the residence brings exceptional scale and thoughtful detail together with remarkable ease. Beyond a private automated gate, a circular paver drive winds past lanterns, mature landscaping, and professional landscape lighting. The approach creates a memorable sense of arrival, while the home’s timeless brick architecture conveys understated presence. Inside, the two-story foyer introduces the craftsmanship found throughout. A sweeping curved staircase, multiple Schonbek crystal chandeliers, distressed maple flooring, and custom millwork establish an elegant yet welcoming atmosphere. The main level is beautifully arranged for both formal occasions and relaxed daily living. A fireside parlor, custom-paneled executive office, and private dining room framed by a custom iron-and-glass wall offer refined spaces for work and entertaining. The expansive family room features a marble fireplace, surround sound, and direct access to stone balconies overlooking the fairway. At the heart of the home, the chef’s kitchen is appointed with Sub-Zero, Viking, and Bosch appliances, granite countertops, a generous center island, warming drawer, and two walk-in pantries. The adjoining sunroom, with cathedral ceilings, a spectacular linear 72 inch raw metal fireplace, and sweeping golf course views, offers an inviting setting for quiet mornings, casual gatherings, and evenings at home. The upper level includes four bedrooms and three full baths. The primary suite is a private retreat with a sitting room, double-sided fireplace, large walk-in closets with separate shoe closet, and a spa-inspired bath with steam shower. Two additional bedrooms share a full bath, while the fourth bedroom has a private en suite with a jacuzzi tub. The walk-out lower level has been designed with the amenities of a private club. A family room with fireplace, second executive office, en-suite bedroom, fitness room with sauna and red-light therapy, and mahogany bar with wine storage, tap system, and kitchenette create an exceptional setting for entertaining and wellness. A covered stone patio extends the living space outdoors. The property’s garage capacity is equally impressive. In addition to the attached three-car garage, a 2,000-square-foot two-level detached stone garage, completed in 2023, features oversized doors, EV charging, epoxy and tile flooring, climate control, security and audio systems, and a cargo lift accessing second-level storage. The space offers remarkable flexibility for a car collection, golf simulator, workshop, studio, or other customized use. Across the grounds, a waterfall pond, herb garden, and 750-foot wooded walking trail create a peaceful retreat. Benches and seating areas are thoughtfully placed for quiet reflection, birdwatching, and time outdoors. A three-level elevator serves the entire residence, providing convenient access from the lower level through the upper level. Since 2019, the home has undergone extensive improvements, including a new well with a 3 HP pump, large capacity water treatment system, lawn irrigation system, plumbing, electrical systems, multiple HVAC systems, integrated smart-home technology for audio throughout the interior extending seamlessly to the exterior, lighting, security, and a home network system. The home also features dual generators, tankless hot water heater, and a certified Presidential roof. Located within South River Colony, the property offers convenient access to Routes 50, 301, and 97, with Annapolis only a short drive away. Rarely does a property offer this level of privacy, scale, craftsmanship, and versatility in one complete setting.