Southwind Homes for Sale

3 Beds ⋅ 3 Baths ⋅ MDQA2017934 MLS ⋅ ACTIVE Status

Welcome to Southwind, one of Kent Island's most desirable waterfront communities, where peaceful surroundings and an exceptional lifestyle come together. Perfectly positioned on 1.22 beautifully landscaped acres with water views, this inviting single-level home offers the comfort, space, and amenities you've been searching for. Inside, you'll find three spacious bedrooms and three beautifully updated full baths, creating a home that is both stylish and comfortable. Freshly painted throughout, with newly refinished hardwood floors and plush new carpeting in the bedrooms, every room feels bright, fresh, and move-in ready. The heart of the home is the welcoming kitchen, featuring gleaming granite countertops, crisp white cabinetry, a generous pantry with charming French doors, peninsula seating for casual meals and conversation, a vaulted breakfast area with a dramatic palladium window showcasing beautiful water views, and brand-new stainless steel range and refrigerator. Whether you're preparing dinner or gathering with family and friends, this space is designed to bring everyone together. The adjoining family room is warm and inviting, centered around a cozy propane fireplace and accented by custom built-in bookshelves that add both charm and functionality. A sliding glass door opens directly to the slate patio, creating an effortless connection between indoor and outdoor living. Just off the main living area, the light-filled dining room is surrounded by large windows that frame lovely water views, creating the perfect backdrop for everyday meals and special occasions. A versatile bonus sunroom offers even more living space and can easily serve as a cozy den, home office, or additional bedroom to fit your needs. Step outside to enjoy the fenced backyard and slate patio, where a remote-operated awning provides welcome shade at the touch of a button, making it the perfect spot for morning coffee, evening sunsets, or weekend barbecues. Car enthusiasts, hobbyists, and those needing extra space will appreciate the oversized four-car garage. Above, an expansive unfinished area offers endless possibilities. Already plumbed for a future bath, it's ready to become a guest suite, home office, recreation room, or whatever your imagination inspires. Energy efficiency is another standout feature, with owned solar panels and two Tesla Powerwall storage batteries helping to keep utility costs remarkably low while providing added peace of mind. Living in Southwind means more than owning a beautiful home—it's embracing a waterfront lifestyle. Residents enjoy access to the community boat launch, waterfront clubhouse, boat storage lot, pickleball and tennis courts, and scenic nature trail along the water. Whether you're launching your boat for a day on the Chesapeake Bay, enjoying an evening stroll by the shoreline, or simply relaxing at home while taking in the tranquil water views, this property offers the perfect blend of comfort, community, and coastal living.

2810 Harvest Ct, Chester

$2,400,000

4 Beds ⋅ 4 Baths ⋅ MDQA2017652 MLS ⋅ ACTIVE Status

Discover an exquisite Mediterranean-style residence nestled in the prestigious Southwind community, where luxury meets comfort while enjoying breathtaking sunset views. This stunning 4-bedroom, 3.5-bathroom home boasts 4,331 sq. ft. The gourmet kitchen features high-end stainless steel appliances, including a built-in microwave, wall oven, and a sleek cooktop, ensuring culinary excellence. Step outside to your private oasis, where a concrete pool invites relaxation amidst lush landscaping on a generous 1.2-acre lot that includes a covered built in Lynx grill and bar seating. Enjoy direct access to Cox Creek, complete with a private dock for fishing, kayaking, or simply soaking in the serene water views. With a double sided fireplace and three tankless water heater, this home combines elegance with modern convenience, making it a true sanctuary. The main living room features sky high ceilings and a wet bar making hosting a snap and flows into the added sunroom that features heated tile flooring. And the three season room off the back is the perfect gathering space with a wall of sliders to maximize the view. Meticulously maintained and thoroughy enjoyed by the original owners. The expansive rear yard and rip-rap shoreline enhance the outdoor experience, while the community amenities, including a beach, tennis/basketball courts, and fishing pier and boat launch, offer an exclusive lifestyle on Maryland's Eastern Shore.

2882 Cox Neck Rd, Chester

$1,100,000

4 Beds ⋅ 3 Baths ⋅ MDQA2017366 MLS ⋅ PENDING Status

Welcome to this pristine contemporary ranch in the coveted waterfront community of South Wind on Kent Island, where luxury, comfort, and resort-style living come together on 1.21 beautifully landscaped acres. From the moment you arrive, the home’s lush green lawn, vibrant gardens, and custom walkways create a picture-perfect setting worthy of a magazine cover. Inside, the open-concept floor plan is filled with natural light and highlighted by gleaming hardwood floors and exceptional upgrades throughout this 4 bedroom, 3 full bath estate. The stunning designer kitchen is truly the heart of the home, featuring crisp white cabinetry, granite countertops, an oversized center island, a premium Wolf 5-burner gas cooktop flanked by custom spice cabinets, a wall convection oven, and built-in microwave...crafted for both everyday living and effortless entertaining. Just beyond the main living areas, the inviting three-season sun porch with white tile flooring overlooks your own private backyard retreat. Step outside onto the expansive maintenance-free decking and new patio surrounding the spectacular heated gunite pool, complete with a waterfall feature and dual stair entrances, creating the ultimate outdoor oasis. The professionally designed landscaping continues throughout the property, accented with colorful plantings, mature greenery, and thoughtfully designed outdoor spaces. A custom-built shed, designed to perfectly complement the home, offers electric service and a gated outdoor storage area. Additional premium features include an oversized two-car garage with air conditioning, two-zone gas heat and central air, a whole-house generator, tankless water heater, updated crawlspace with dehumidifier, and energy-saving foil-wrapped attic insulation. The roof is only two years young, offering peace of mind for years to come. Perfectly positioned to capture serene open-space and water views, this exceptional property also includes access to South Wind’s sought-after amenities, including a community beach, boat ramp, pier, tennis courts, dry dock, and more. This is more than a home...it’s a private Kent Island retreat designed for exceptional living.

2812 Harvest Ct, Chester

$2,450,000

4 Beds ⋅ 5 Baths ⋅ MDQA2017210 MLS ⋅ ACTIVE UNDER CONTRACT Status

Sited on Cox Creek with 369 feet of waterfront, this elegant contemporary residence offers 2.3 private acres, spectacular western exposure, and breathtaking sunset views. Thoughtfully designed to maximize water vistas from nearly every room, the home features 4 bedrooms, 3 full baths and 2 half baths, and approximately 4,717 square feet of refined living space. The gourmet kitchen is appointed with rich custom cabinetry, granite countertops, upgraded stainless steel appliances, and a gas cooktop, creating an ideal setting for both everyday living and entertaining. Custom hardwood flooring spans the main level, complemented by two fireplaces and timeless architectural details throughout. The luxurious main-level primary suite offers serene water views, multiple walk-in closets, and a recently renovated spa-inspired bath. A beautiful three-season room overlooks the creek, providing the perfect space to relax and enjoy the tranquil setting. There is also ample room to add a pool. Upstairs, three additional bedrooms and two full baths provide comfortable accommodations for family and guests, with three of the four bedrooms enjoying water views. The upper level has been recently updated with luxury vinyl plank flooring in place of carpet. Additional highlights include mature professional landscaping, a temperature-controlled wine room, a 3-car garage, a new roof, private pier with electric and water, boat lift, jet ski lifts, and riprap shoreline protection. Located in the desirable Southwind community, residents enjoy amenities including a boat launch, boat storage area, tennis courts, walking trails, and a clubhouse — all conveniently located near shopping, dining, and more.

2832 Cox Neck Rd, Chester

$1,195,000

4 Beds ⋅ 5 Baths ⋅ MDQA2016942 MLS ⋅ ACTIVE Status

Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring upgraded countertops and a spacious island, flows seamlessly into the family room, perfect for entertaining. Relax in the primary suite with a lavish bath or unwind in the inviting family room by the fireplace with views out to Crab Alley. Three additional bedrooms (or two bedrooms and an office) and two baths round out the main level that offers sweeping scenic views from every vantage point. Step outside to discover a private oasis on 1.25 acres, complete with extensive hardscaping, a heated in-ground pool, and a soothing hot tub. Enjoy picturesque water views out the front and back, with access for kayaking and boating. The community amenities, including a beach, clubhouse, and tennis courts, elevate your living experience. This home is not just a residence; it's a lifestyle waiting to be embraced and enjoyed. Start living your best 'Shore Life' at 2855 Cox Neck Rd.

2855 Cox Neck Rd, Chester

$1,825,000

4 Beds ⋅ 6 Baths ⋅ MDQA2015546 MLS ⋅ CLOSED Status

Set within Southwind, one of Kent Island’s most sought-after waterfront communities, this exceptional residence offers an elegant blend of craftsmanship and comfort with 10 foot ceilings and beautiful crown molding. Perfectly sited on an acre overlooking Crab Alley Bay and Eastern Bay, the home’s peaceful setting is enhanced by sweeping water views, mature landscaping, and a private waterside pool that invites year-round enjoyment. Inside, timeless design meets modern refinement. The first-floor primary suite provides a serene retreat, joined by two additional guest suites on the main level—each with its own ensuite bath for privacy and comfort. Upstairs, a fourth bedroom and full bath accompany a spacious living area, ideal for extended family or guests. The heart of the home is a stunning, renovated kitchen featuring rich finishes, premium appliances, and an open layout perfect for gathering. Gleaming hardwood floors flow throughout, leading to a mahogany-lined library that exudes warmth and sophistication—a true sanctuary for work or quiet reflection. Outdoor living takes center stage with a screened porch that captures cooling Bay breezes and views of the pool and shimmering water beyond. Whether entertaining or simply savoring the stillness of the shoreline, every space in this home celebrates the beauty of the Chesapeake Bay lifestyle.

2907 Cox Neck E Road E, Chester

$1,850,000

6 Beds ⋅ 6 Baths ⋅ MDQA2009014 MLS ⋅ CLOSED Status

This stunning waterfront, custom built home sits ideally on a little over an acre fronting Crab Alley Bay in the prestigious Southwind community. Home boast almost 10,000 square feet, between finished living space and additional expansion space. An already large home offers so much more room to grow the perfect, waterfront retreat. This gem features 6 large bedrooms and of those 4 have private baths, and walk-in closets. Original owners designed this home to highlight 8' solid wood doors, Brazilian cherry hardwood floors, high ceilings through-out the first floor, two focal point fireplaces, second floor balcony, come see it all and in vison the possibilities this property offers. This is truly a must-see property. Not to mention its LOCATION. Nestled in the Southwind community that features a clubhouse, basketball court, pickle ball court, tennis court, boat ramp, and plenty of ways to enjoy the nature.

2817 Cox Neck Road, Chester

$1,700,000

4 Beds ⋅ 3 Baths ⋅ MDQA2012964 MLS ⋅ CLOSED Status

Welcome to waterfront living at its finest in the highly sought-after Southwind community on Kent Island, where this stunning home offers one of the most breathtaking views of Crab Alley Bay. Perfectly positioned with an east-facing orientation, you'll enjoy spectacular sunrises that paint the sky and reflect off the water each morning. This beautifully designed 4-bedroom, 2.5-bath residence blends comfort and elegance with panoramic bayfront vistas from nearly every room, including the living room, dining room, sun-drenched sunroom, and family room with a warm and inviting stone fireplace. The main level features three well-appointed bedrooms and 1.5 bathrooms, while the upper level is home to a serene, newly carpeted bayfront primary suite complete with an ensuite bathroom, walk-in closet, and a versatile loft space ideal for a home office or reading nook. The kitchen is as functional as it is stylish, boasting granite countertops and a suite of new and newer stainless-steel appliances. Additional recent upgrades include a new washer and dryer, newer windows (majority) and marine grade sliding glass doors (2024), a 2024 gas furnace, and an on-demand gas water heater—ensuring year-round efficiency and comfort. Step outside to your private waterfront paradise, where a spacious deck invites family gatherings and summer barbecues, and a cozy hardscape feature with a space for your crab feast table and a custom firepit sets the scene for relaxing evenings under the stars. The pier has been thoughtfully updated with new decking and a brand-new boat lift, ready to launch your next adventure on the bay. An oversized two-car garage provides ample space for vehicles and storage. Whether you're entertaining outdoors, soaking in the views from the sunroom, or heading out for a day on the water, this home captures the very best of Chesapeake Bay living.

2921 Cox Neck E Road E, Chester

$2,250,000

3 Beds ⋅ 3 Baths ⋅ MDQA2010736 MLS ⋅ CLOSED Status

*Cancelled Open House for Sunday Sept 29th. * Landscaped for privacy, this elegant waterfront home is sited on 2.6 acres and located in the Lovely community of Southwind. Filled with light and incredible views of Crab Alley Bay, this home offers a fabulous floor plan with architectural accents that define charming living spaces. Walls of glass along the waterside provide most rooms with broad water views. Taupe Engineered Hardwood Floors installed in 2022. Inspiring great room with 12 ft ceiling and high efficiency gas fireplace opens into the dining area with 10 ft ceiling. There is a custom crafted library offering lighted floor to ceiling built-in bookshelves (or display areas) with a rolling ladder to allow full access. In 2022 this home's floor plan was improved with the addition of a magnificent and spacious gourmet kitchen which is complimented with vaulted ceilings and fabulous seating around the gorgeous Blue Calcite Marble island countertop. Top shelf appliances include Wolf double wall ovens, 36-in Wolf cooktop with six burners plus a Sub-Zero double door refrigerator. The cabinet and counter space seem endless and are further enhanced with an artful backsplash. There is a 2nd Sub-Zero double door refrigerator in the user-friendly butler's pantry which offers additional storage and counter space. Thoughtful placement of a full bath off the pantry allows easy access to the pool. The waterside primary bedroom suite has a private balcony, walk-in closet and gorgeous bath with walk-in shower and Bubbler jetted tub. The roof was replaced in March of 2024 with a 50-year GAF architectural shingle with a 50-year transferable warranty. Did I mention the waterside screened gazebo, waterside office and two car attached garage that opens to the mudroom and the dedicated laundry room with built-in cabinets, sink and a lighted folding table? In 2022, this home was completed with a 15x40' Gunite Pool that is 7' deep and surrounded by Afyon Cloud Marble Tile. It is simply stunning! There is plenty of room for entertainment or to just rest and relax to the sounds of nature and the bay on the sandy beach. The sandy beach is a perfect spot for launching kayaks and water toys and is adjacent to the 160 ft dock that extends into Crab Alley Bay. Beyond the beach is a gorgeous rip wrapped shoreline. The water views and sunrises over the Crab Alley Bay are simply spectacular! The Upscale Southwind Community amenities include a Clubhouse, waterfront walking trails, Tennis/Pickle Ball Court, Basketball Court, Boat Launch, Boat storage.

2801 Cox Neck Road, Chester

$2,100,000

4 Beds ⋅ 5 Baths ⋅ MDQA2010612 MLS ⋅ CLOSED Status

This superb custom Southern Living plan boasts impressive deep, intricate trim and multiple custom windows/transoms and is designed to take advantage of the expansive water views. The two-sided soaring brick fireplace can be used as a gas or a woodburning unit. A volume 2-story Great Room offers a wet bar for easy entertaining and access to a sizable deck along with extraordinary panoramic water views for miles! The sumptuous Gourmand Kitchen houses a commercial-style gas stove and a vast center island. The Breakfast Nook overlooks a sparkling 20X40 heated Inground Pool, generous stone patios and an absolutely breathtaking and truly exceptional Gazebo built with an outdoor kitchen that includes a grill, burners, a sink and multiple appliances, combined with a large mounted TV and plentiful seating for the ultimate outdoor living experience! A fourth wonderful full bath is found just off the garage and an outdoor pool shower is also provided for your boating and swimming enthusiasts. The well-lit 300 ft private pier houses a lift for your power boat plus additional space for a smaller watercraft to emphasize what a true waterfront lifestyle can offer. You will find a very generous main level Primary Suite featuring abundant closest space, a luxury bath and access to the deck in this gracious waterfront residence. A second rear staircase off the first floor Laundry and Pantry takes you to an additional lovely large Family Room and Office space which adjoin three Guest Bedrooms and two additional baths. Prepare to serve and entertain family and friends in the Formal Living Room and Romantic Formal Dining Room. Perhaps you will want to idle away the hours on the extensive front porch in the Southern Living style as you watch the sun set or bring that coffee cup out to your deck or Gazebo to see mesmerizing sunrises and your wine glass or drink out to face East to see memorable horizons where the moon comes majestically up to meet you. Community amenities include a Clubhouse, waterfront walking trails, Tennis Court, Boat Ramp and a small Playground. Lots of community events are held there if you want to join! Owner unsure of water frontage...believed to be wider that 210 ft. shown.

2869 Cox Neck Road, Chester

$942,000

4 Beds ⋅ 4 Baths ⋅ MDQA2008712 MLS ⋅ CLOSED Status

Price adjustment. Welcome to 2802 Cox Neck Road, nestled in the coveted Southwind community. This meticulously maintained home sits on over an acre of well-manicured land and offers picturesque views of the Crab Alley and the Chesapeake Bay. Step inside to discover over 3,600 square feet of bright, comfortable living space. The main level features an open layout with a welcoming great room, formal living and dining areas, a bright sunroom, and two versatile offices. The well-designed kitchen and dining space also has access to a peaceful patio and the backyard. Upstairs, the spacious primary bedroom boasts a full bathroom, walk-in closet, and dual vanities. In addition to the primary suite, the home offers three additional bedrooms and two full baths and ample closet space. The upstairs landing offers beautiful views of the entryway and great room. The unfinished walkout basement provides an additional 1,810 square feet of potential storage or expansion space. The two-car attached garage offers plenty of room for vehicles and a work area. Southwind is a waterfront community with gorgeous views and access to the surrounding waters of Cox Neck Creek, Eastern Bay and Crab Alley Bay. Southwind offers residents access to a clubhouse, a small craft boat ramp, tennis courts, a nature trail and a boat storage area. The clubhouse is used for community events and celebrations. This community is conveniently located near Route 50, with easy access to Annapolis, Easton, Washington DC, Baltimore, and Saint Michaels. Experience the perfect blend of luxury and convenience at 2802 Cox Neck Road!

2802 Cox Neck Road, Chester

$925,000

4 Beds ⋅ 5 Baths ⋅ MDQA2007998 MLS ⋅ CLOSED Status

Welcome home to 2904 Cox Neck Rd E perfectly nestled in the peaceful and scenic water privileged community of Southwind located on a point of land completely surrounded by water. Feel like you are on VACATION EVERY DAY!! This beautiful 4 bedroom home offers a delightful blend of leisure and lifestyle and is absolutely a MUST SEE!!! As you walk in through the elegant front entry you will immediately note the stacked crown molding, high ceilings, a ton of natural light, and gorgeous wood flooring that has been meticulously maintained by the owners. Located off the entry is a large and inviting living room that spans the entire side of the home and opens to a large back deck. The living room also opens to the spacious gourmet kitchen and dining area with large windows and doors that look out to the home's picturesque surroundings. Before heading upstairs be sure to take a look at the large walk-in pantry as well as the huge 3 car garage with a ton of storage and 11-foot ceilings which can be accessed via a side door off the kitchen. Upstairs you'll find a beautiful primary bedroom complete with its own private balcony and a custom designed bathroom with two walk-in closets and a ton of organization throughout. Two bedrooms with a Jack-n-Jill bathroom are also located upstairs. On the other side of the home, the upstairs offers a large open concept room with cathedral ceilings that is perfect for a rec room as well as a study area as it offers office built-ins. Off this room is ANOTHER primary bedroom and full bathroom perfect for an au pair suite, in-law suite or just someone who is very lucky. A second set of stairs will take you back down to the kitchen area/garage entry making for perfect flow throughout the home! Before you head outside make sure you take the steps off the entry to the huge finished basement complete with a full bathroom -- so many possibilities! Heading outside you'll see that the house is truly framed by nature’s beauty on all sides with serene and peaceful seasonal water views! The community of Southwind offers a boat launch, boat storage, waterside tennis/pickleball courts, basketball court, waterfront clubhouse, and scenic walking trails. Close to prime shopping and dining as well as Route 50 and yet privacy abounds in Southwind! Truly a sanctuary of peace away from the hustle of daily life -- do not miss this opportunity!

2904 Cox Neck E Road E, Chester

$1,800,000

5 Beds ⋅ 3 Baths ⋅ MDQA2007534 MLS ⋅ CLOSED Status

This is the waterfront dream home you’ve been waiting for! Are you looking for expansive bay views from your forever home or second home on the Eastern Shore? This 5 BR, 2.5 BA property with 110 feet of rip rapped waterfront delivers with 2.9 manicured acres (one of the largest lots in the community!) in the serene upscale community of Southwind. You will enjoy this secluded setting with wide sweeping water views surrounded by Crab Alley and Eastern Bay. Just steps down the back yard is the six-foot wide pier with both boat and jet ski lifts and a gorgeous custom salt-water pool surrounded by a pristine paver patio and walkways. Enjoy boating, jet skiing, fishing, crabbing or just relax on the pier and enjoy your morning coffee as you soak in the sunrise! The backyard oasis includes screened porch, two-level Timber Tech decks and waterside fire pits set up for bay view entertaining and fun, fun, fun! This gem has been lovingly cared for every step of the way and is in pristine condition with a major remodel in 2015. This is a rare opportunity and the first time this property has been on the market. Marvel as you enter into gleaming blonde hardwoods throughout the first floor and upstairs hallway of this 3,718 finished square foot home. Seven rooms on the water side have wide open views of the bay! The foyer features an 18-foot ceiling and 9-foot ceilings throughout the first floor including living, dining, breakfast room, kitchen, bathroom, and office/bedroom. There is a wood burning masonry fireplace flanked by custom built-in bookshelves to enjoy in the chilly winter months. First floor also has a office that could be converted to a first floor bedroom or sixth bedroom if needed. The 1.6-acre communal easement immediately adjacent to the left of the home insures you will have no neighbor to the left adding to the secluded setting. The community of Southwind also offers a boat launch, boat storage, waterside tennis or pickle ball courts, basketball court, waterfront club house for events and year round activity calendar, walking trail with a pair of nesting bald eagles and much more! Close to prime shopping and dining, yet privacy abounds in this upscale neighborhood. Want to go to restaurants by boat? This location is a short boat ride to the Narrows and St. Michaels! Kent Island’s expansive Cross Island Trail with miles of biking, running, and walking trails provides endless opportunities for locals to enjoy all the island has to offer! This is a MUST SEE!

2861 Cox Neck Road, Chester

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