Southwind Homes for Sale

5 Beds ⋅ 3 Baths ⋅ MDQA2007534 MLS ⋅ ACTIVE 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. 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 Rd, Chester

$1,725,000

4 Beds ⋅ 5 Baths ⋅ MDQA2006102 MLS ⋅ CLOSED Status

OFFERS DUE 12noon, Monday, 4/3. ** Beautiful 4 BR, 4.5 BA, 4,033 sf waterfront home on 2.1 professionally maintained acres (one of the largest lots in the community). Welcome to your dream home in the serene Southwind community in Cox Neck between Cox Creek and Crab Alley Bay on the Chesapeake Bay!! All the fun by day taking the boat and kayaks out from your private dock (with lift), swimming in the low maintenance salt water pool (new liner and cover 2022) and hot tub. In the evening, take in the breathtaking sunset views on the back deck. Enjoy making quiet dinners or entertaining in the new kitchen (2022) with stunning quartz counters and all new stainless appliances. Have your morning coffee and breakfast looking out over the calm waters of Cox Creek. New plantation shutters and beadboard (2017). Relax by the fireplace in the open floorplan living room with high ceilings and lots of light from the large palladian windows. Formal dining room for entertaining. Main level primary bedroom with water views, luxurious bathroom with jetted tub, separate shower with two shower heads, and large walk-in closet. Laundry room with newer high efficiency washer and dryer (2019) is on the same level as the primary bedroom. 2 bedrooms and two bathrooms plus an office upstairs, including a large finished room over the garage with a private bath. 3 car garage plus extra parking on the large drive. New roof (2017). 3 HVAC zones. 2 water heaters. Large 1200gal underground propane tank. New well water treatment system (2 years). Encapsulated, dehumidified crawl space with sump pump. Landscape lighting highlights mature hydrangea and rhododendron plantings as well as river birch, sycamore, sugar maple, cherry and ornamental plumb trees. Southwind community features a beautiful waterfront clubhouse with year round activities calendar, new (2021) sports courts for basketball / pickle ball / tennis and community nature walk with a pair of nesting bald eagles.

2856 Cox Neck Road, Chester

$1,750,000

3 Beds ⋅ 4 Baths ⋅ MDQA2003830 MLS ⋅ CLOSED Status

DREAM HOME ALERT! Situated perfectly on Crab Alley Bay looking out over Eastern Bay. This meticulously maintained home has it all. A contemporary floor plan, maximizing the water views with floor to ceiling windows. Relax by the pool overlooking the newly renovated dock, equipped for your power boat and jet skis. Call today for your private tour!

2909 Cox Neck E Road E, Chester

$1,640,000

3 Beds ⋅ 3 Baths ⋅ MDQA2004354 MLS ⋅ CLOSED Status

Professional Picture Coming Soon. Beautiful Coastal two story WATERFRONT with expansive, broad views! 97 custom home community on a stunning peninsula surrounded by water everywhere you look! Estimated water frontage is unknown (120-175 ft). Private pier with lift (not used by owner so AS IS). Fish and crab off your own dock! Breathtaking water views add to the fabulous outdoor living spaces including a sizable screened porch, a large deck, barbecue section and small fish pond. The main level is spectacular with walls of windows to take advantage of the extensive water views, a lovely family room with a fireplace, a generous dining area and a nearly brand new luxurious Kitchen boasting impressive white cabinetry, superb upgrade designer lighting, pendants, countertops and backsplash with an adjacent Morning/Breakfast room featuring a climate-controlled Wine Closet! There is a two-story entry foyer and a Guest BR with full bath on the main level as well. Upstairs you will find the Primary MBR suite and a second Guest BR and bath along with a cozy lofted sitting area or second family room. Don't miss this rare opportunity to see a much-loved waterfront residence in Southwind at one of the very lowest waterfront prices!

2863 Cox Neck Road, Chester

$1,635,000

5 Beds ⋅ 3 Baths ⋅ MDQA2001298 MLS ⋅ CLOSED Status

Expansive views of the Eastern Bay with sunsets for days. Welcome to the most idyllic spot you will ever imagine. Pristine landscape on just over an acre of waterfront luxury with stone accents, a private pier, complete with boat and jet ski lifts, and water and power. The entry to this unique residence is reminiscent of a southern plantation with its sweeping front steps leading to the porch. Peering through the full glass front door, your eyes will be drawn straight to the amazing water views from the western facing side of the home. The high ceilings and open concept flow of the interior make moving about this home free-flowing. With water views and views of verdant landscape catching your eye from every angle of this home, you won't need artwork as the light-filled windows capture nature at its finest. The veranda overlooking the water is perfect for your morning coffee or even better the evening glass of wine as you breathe in the beauty and let the stress of the day fade away. Lounging on the balcony outside the primary bedroom will quickly become your favorite pastime, where you can relax with a good book or just gaze at the wildlife habitats that surround you. The main level of the home features 3 bedrooms and 2 full baths, a dining room, a separate office as well as a family room, and a chef's style kitchen. Stone accentuates the fireplace and is the focal point of your entertaining space. Moving to the lower level with soaring high ceilings, there is even more entertaining space with a custom bar, 2 additional bedrooms and full bath, and walk-out sliders to the patio area complete with a dry bar and built-in hot tub. Additional features include barn doors, steam shower, outdoor shower, spiral stairs from the outside to the upper balcony, firepit, private stone beach area, a completely rip-rap shoreline, and an oversized 2 car side load garage. Community amenities, convenience for commuting, wide neighborhood streets for walking and riding bikes, it just doesn't get any better. Come live the wonderful Eastern Shore lifestyle, you won't regret it!

2842 Cox Neck Road, Chester

$865,000

4 Beds ⋅ 5 Baths ⋅ MDQA2001034 MLS ⋅ CLOSED Status

Beautiful four/five bedroom home in Southwind community with Bay views from almost every room. The home offers stacked crown molding and high celings, new carpet and maple flooring. The kitchen has stainless appliances, a large pantry and lots of space for entertainment. The family room is off the kitchen with a propane fireplace and opens to a large deck with beautiful scenic views. The master suite has a large private deck, vaulted ceilings, a custom- designed bathroom with two large closets and lots of space. The home also has a spacious guest suite and two more bedrooms with a Jack-and-Jill bathroom. A large office separated from the living space with cathedral ceiling and office built-ins is the ideal place to work from home. The basement is finished with new flooring and a bathroom and could be used as an additional bedroom suite, game room, media room, playroom or gym. Endless possibilities. The three car super-sized garage offers lots of storage with built-ins and eleven foot ceilings. Ultra efficient Geothermal HVAC system will save you in heating and cooling costs plus there is new LED lighting throughout the home. This private waterfront community on Kent Island offers a clubhouse, boat ramp, tennis, basketball, nature trail and a private boat storage area. All this just minutes to Route 50 and the Chesapeake Bay Bridge. Vacation where you Live!

2904 Cox Neck E Road E, Chester

$825,000

3 Beds ⋅ 3 Baths ⋅ MDQA147374 MLS ⋅ CLOSED Status

This amazing 3.07-acre property is the second largest lot in Southwind with stunning water views to the East and West. The large and private front porch entrance brings you inside this home to the foyer where your eyes are drawn to the stunning views of the eastern bay! Connected to the front porch is another porch that is screened-in for relaxing and catching both stunning sunrises and colorful sunsets! Sitting at the dining room table you have both east and west views of the water! The massive kitchen with eat-in table space is perfect for entertaining. This home features soaring 22’ beamed ceilings with a massive palladium window in the family room looking out to the Eastern Bay! Nothing better than the Zen life-style of amazing water views. Nestled among beautiful crape myrtle trees on a massive lot, you have privacy, ambiance, and room to expand. This home is a perfect match for a discerning buyer who is looking to put their touch on this amazing property and bring it too to a Million Plus home.

2851 Cox Neck Road, Chester

$1,100,000

5 Beds ⋅ 5 Baths ⋅ MDQA146170 MLS ⋅ CLOSED Status

Casual elegance in the water privileged community of Southwind. Water views of both Eastern Bay and Crab Alley Bay from almost every room in the house. Two story foyer, high ceilings on the first floor and vaulted ceilings on the second floor. Brand new windows throughout. Crown molding, custom trim, pocket doors, all hardwood floors plus a large basement for a gym, art studio and recreational space- tons of potential. Beautiful updated kitchen. Main level guestroom with full bath. Entertaining is easy with a large screened porch, multiple decks and a private inground pool with fence. Formal dining room, family room with cozy wood fireplace and individual quiet spaces. Multi room master suite with dual spacious closets, master bath and deck overlooking the water. Ensuite bedrooms and two office spaces perfect for telecommuting. Ample storage with large closets and an oversized garage. The private waterfront community on Kent Island in Chester, Maryland offers a clubhouse, boat ramp, tennis, basketball, nature trail and a boat storage area. All this just minutes to Route 50 and the Chesapeake Bay Bridge. Vacation where you Live!

2902 Cox Neck E Road E, Chester

$1,900,000

4 Beds ⋅ 4 Baths ⋅ MDQA147842 MLS ⋅ CLOSED Status

TAKING BACK-UP OFFERS. Sellers will accept back-up offers, but will not have showings. WARNING!! You may never want to leave this home ! With views of the sparking bay through floor to ceiling windows in most rooms, the sun will soak into your skin and soothe your soul. This is one-level living at it's finest.

2909 Cox Neck E Road E, Chester

$1,421,003

4 Beds ⋅ 4 Baths ⋅ MDQA147578 MLS ⋅ CLOSED Status

New construction home.

2923 Cox Neck E Road E, Chester

$1,200,000

4 Beds ⋅ 6 Baths ⋅ MDQA146446 MLS ⋅ CLOSED Status

Waterfront in the desirable Southwind community minutes to the Bay Bridge. Four bedrooms and six bathrooms. Waterfront - elevated- lot with open views. Large FIRST FLOOR masterbedroom. Hardwood floors and carpet. Cherry floors in the separate dining room and in the study/office. Basketball/pickleball waterfront court. Inground concrete pool (pool is being sold as is). Second floor has a full bath, separate bedroom and living space with waterviews. Two wood fireplaces, one in the family room and one in the large master bedroom. Screened in porch off the master bedroom and study. 2 car garage with additional storage space. Large attic space for storage or future living space. This property has all the potential needed to become your DREAM home.

2907 Cox Neck E Road E, Chester

$1,097,000

3 Beds ⋅ 4 Baths ⋅ MDQA140280 MLS ⋅ CLOSED Status

TRUSTEE SALE ! MUST SELL! One level living at it's finest. Breathtaking water views of Eastern Bay. large open living concept. Screened porch over looks private in ground pool, and flat yard leading to your own private dock. Located in Southwinds, this home will not disappoint!

2867 Cox Neck Road, Chester

$1,360,000

3 Beds ⋅ 3 Baths ⋅ MDQA146426 MLS ⋅ CLOSED Status

Beautiful Southwind waterfront home! Incredible broad water views! Custom inlaid hardwood floors throughout! Super 2 story entry foyer with extended views! Huge white eat in kitchen with dining area! Gorgeous living room featuring gas log fireplace, decorative mantle, slate hearth + built-ins. Adjacent waterfront den w/ floor to ceiling collection display shelves, brick floor & recessed lighting. Main level home office! Huge screen porch w/brick floor, ceiling fans, recessed lighting + 60 foot brick patio. Upper level primary bedroom & primary bath both with stunning water view, plus 2 more bedrooms. Giant upper level game room featuring wet bar, pool table, decorative flooring, built-ins & custom lighting. Extras include: fire pit, retractable awning, generator, pool table, custom draperies, moldings, third bay garage storage, martin houses, and pier with new decking and boat lift!

2911 Cox Neck E Road E, Chester

$2,050,000

6 Beds ⋅ 7 Baths ⋅ MDQA146042 MLS ⋅ CLOSED Status

2821 Cox Neck Road, Chester

$1,375,000

4 Beds ⋅ 3 Baths ⋅ MDQA145724 MLS ⋅ CLOSED Status

Welcome to 2842 Cox Neck Rd. located in prestigious Southwind on the Eastern Bay. This elegant 4 bedroom 3 bath home is situated on just over an acre of finely manicured landscape with UNBELIEVABLE water views! The impressive front entry will lead you to an open concept and window filled kitchen, dining, and living area with expansive water views on the upper level. The updated kitchen is a chef's dream, boasting granite counter tops, double wall ovens, six burner gas stove, deep stainless steel sink and walk in pantry; not to mention, an outdoor grilling station! Down the hall you will find the owner suite with an upgraded bathroom featuring double vanity, Jacuzzi tub and steam shower, two walk in closets and access to the balcony with relaxing views and spiral staircase. This level also includes two large bedrooms, full hallway bath, oversized laundry room and home office. On the ground level is an additional bedroom, full bath, home gym, storage and a great room with breathtaking views leading to extended outdoor living. A spacious patio with built in seating, fire pit, bar, hot tub, shower & private pier with three lifts make this the ideal spot for enjoyment and entertaining! Fall in love with all that this home has to offer by scheduling your showing today!

2842 Cox Neck Road, Chester

$1,100,000

4 Beds ⋅ 4 Baths ⋅ MDQA145400 MLS ⋅ CLOSED Status

2871 Cox Neck Road, Chester

$1,278,000

5 Beds ⋅ 4 Baths ⋅ MDQA142750 MLS ⋅ CLOSED Status

Great, Custom Colonial on Crab Alley Bay, located in the community of Southwind. Home features large open spaces on first and third floor, custom kitchen, new master bath, freshly painted throughout, Tile & Hardwood, 5 bedrooms & 3.5 baths. Use your flex space on the third floor for exercise room, home theater, run a home business or much more. Watch the beautiful sunrises, kayak and take your boat out for a spin from your pier. Set up for outdoor living with a beautiful built in pool, large screened porch.Virtual Tour Link https://thru-the-lens-ivuf.view.property/1277650?idx=1

2903 Cox Neck E Road E, Chester

$1,365,000

4 Beds ⋅ 4 Baths ⋅ MDQA145408 MLS ⋅ CLOSED Status

Beautiful waterfront home in the waterfront community of Southwind. Sweeping views of Crab Alley Bay from almost every room in the house. Random plank red oak floors, new kitchen with quartz counters, formal dining room or office, family room with cozy fireplace, large enclosed porch/sun room with water views and so much more. Master bedroom on the main level with an adjoining sitting area, modern master bath with radiant heat, tub, large shower and lots of light. Three extra bedrooms and two baths on the second level. Lots of character and upgrades in this Cape Cod. The landscaping is a work of art and the front porch will be ideal to watch the sunsets. Two hundred feet of water frontage for your enjoyment and your own pier. New duct work in crawl space and an Air Scrubber installed for a healthy environment. The private waterfront community on Kent Island in Chester, Maryland offers a clubhouse, boat ramp, tennis, nature trail and a boat storage area. All this just minutes to Route 50 and the Chesapeake Bay Bridge. The perfect place to telecommute. Vacation where you Live!

2803 Cox Neck Road, Chester

$1,440,000

4 Beds ⋅ 4 Baths ⋅ MDQA142834 MLS ⋅ CLOSED Status

Broad water views and light fill this elegant contemporary located in the desirable community of Southwind. This custom built home has an outstanding floor plan offering 3539' of living space. Walls of glass surround the waterside 2 story family room which is open to the gourmet kitchen with Granite counter tops, stainless appliances and island. The kitchen is large enough for a comfy table and chairs. There is a separate dining room too. Upstairs are 4 bedrooms and 3 full baths. Two bedrooms are connected with Jack and Jill bath. The third bedroom has an attached bath with hallway entrance. Lovely master suite is spacious with sitting room, huge bath, his and her walk in closets and waterside 32 x 14 private deck. Hardwoods and water views throughout. Exterior shower enclosure and 3 car garage. Located at end of community in cul de sac for more privacy and steps from clubhouse, tennis cts and community water features.

2888 Cox Neck Road, Chester

$1,370,000

4 Beds ⋅ 4 Baths ⋅ MDQA144822 MLS ⋅ CLOSED Status

The Perfect 10! Nestled in the Private Southwind Community, this Contemporary Style 4400sq ft home sits on 1.20 acres and BOASTS 180' of unobstructed views of the mouth of the Eastern Bay where Novel Eastern Shore Sunsets can be seen nightly! Whether working, learning or just spending more time at home, this home offers an expansive amount of space with impeccable water views from nearly EVERY window - VACATION WHERE YOU LIVE! The first floor features an OPEN floor plan with Gleaming Hardwood floors throughout the Sunken Living room, Dining room, Hallways and Gourmet Kitchen. Soaring Ceilings and a WALL of windows with breathtaking Eastern Bay Water views are the highlights of the Great Room off the Kitchen & also features a wood burning fireplace & ceramic tiled floors. Take the party outside to an entertainers PARADISE complete w/ a 14x18 Deck, Custom Fire Pit & Patio by the Waterfront, 150ft Commercial Grade Pier w/ 2 boat lifts, electric, water, & secured Bench to take in the scenery the Bay has to offer! Upstairs features a Master Suite w/ sitting area, balcony overlooking the waterfront, en suite full bath w/ soaking tub & HUGE walk in closet, & down the hall you'll find the 2nd & 3rd bedrooms w/ Jack&Jill bath & the Laundry Room w/ Pull down Attic Stairs for additional storage. The "West Wing" of the home boasts a 1st floor bedroom & full Bath, an immaculate 2 car oversized garage & and living space above the garage w/ a sitting room, 2 offices, bonus room & 4th full bath which easily could be converted to in-law quarters w/ it's own separate entrance! The list goes on for ALL that this EXTREMELY WELL MAINTAINED home has to offer - check out the YouTube video tour & schedule an in-person showing today!

2838 Cox Neck Road, Chester

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