20 houses for sale in Winter Harbor Haven

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Welcome to this cozy waterfront farmhouse on 20 peaceful acres along Pepper Creek. With two bedrooms and one and a half baths, the home offers privacy, country charm, and room to enjoy coastal living. Spend your days kayaking, paddleboarding, or simply watching the wildlife along the creek. The property also offers space for crabbing, oyster growing, and gardening, with a greenhouse and a detached workshop for your projects. Inside, you’ll find new LVP flooring throughout, new hurricane-rated replacement windows, five mini-split units for heating and cooling, and a woodstove. Approximately three miles from the New Point Comfort Lighthouse observation deck, this property could be your quiet retreat, homestead, or waterfront getaway. Some photos have been virtually staged to showcase the home potential

Looking for a renovation project? This two Bedroom one bath home is awaiting your creativity. Located on a half acre on an hard service road in the historic Mathews County. House has a huge covered front porch and a detached Shed. Remodeling was started on the home and then stopped. Property sells'as is'. Cash or rehab loan only. House next door is also for sale

Diamond in the rough. This house and the one next door (244 Red Mens Hall Rd) are both for sale for $80,000 each. Renovations were started on both but then halted. Both need considerable work. Adjacent. 16 Acre lot is also for sale. Property sells as is, where is. Owner has never occupied the property so has no information on systems etc. This house is a standard Ranch with replacement windows. Bathroom has been gutted, waiting on a new look. Hardwood floor in most of the house

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Gorgeous waterfront home! Meticulously renovated waterfront home with lots of character! Gorgeous views of the West Landing creek from this 2 story colonial boasting a large foyer, formal dining and living rooms with an open concept and gas fireplace, custom kitchen with quartz counters, new appliances, and soft close cabinets throughout. First floor offers a downstairs en-suite primary while second floor offers an oversized private primary suite with access to the rear balcony. 3 additional upstairs bedrooms and full hall bathroom with double vanity. Whole home generator, new trex style decking on both rear decks, custom functional shutters. Call today to schedule your showing!

Escape to peaceful Mathews County! Situated on 7.96 acres along a private road, this charming 1,326-square-foot farmhouse offers the perfect blend of country living, privacy, and coastal convenience. Inside, you’ll find 2 bedrooms, 2 full bathrooms, and a spacious, inviting floor plan. The home features a large living room, dedicated dining room, and roomy kitchen, along with a separate laundry room and sunroom that offers additional space to unwind and enjoy the peaceful surroundings. Outside, the possibilities are endless! The property features a barn with multiple stalls, two large pastures, and a chicken coop, making it ideal for horses, hobby farming, or anyone dreaming of their own homestead. Enjoy the peace and quiet of rural living while being just minutes from Haven Beach and the beautiful waters of the Chesapeake Bay. This could be the family farm your kids tell their kids about!

Why wish upon a star when you can come home to Moon? This almost-new home, custom built in 2024, offers three bedrooms and two full baths. Make your home base for life in Mathews County, whether you're settling in year-round or creating a getaway of your own. Your next chapter starts here! No flood insurance required, completely encapsulated crawl space. Bring your pets to a fenced in backyard

Property features 8.59 semi cleared acres. Water views of Pepper Creek. Well, Septic, and power at existing dwelling. Multiple sheds, and a 3 bay pole barn with workshop and electric convey with sale. Property will require a renovation loan or tear down and use the land for a construction loan. Buyer to do due diligence regarding permitting, zoning, and all other components. Seller makes no guarantees. See shared disclosures on addendum. Property STRICTLY conveyed as is where is, and with all faults. Seller will make NO repairs. HVAC not currently functional. Do not access the property without a confirmed appointment. Property is occupied

Where timeless character meets modern comfort—and water surrounds you from both directions. Tucked away on 2.45 beautiful acres, this one-of-a-kind property offers the rare opportunity to enjoy waterfront on both the front and rear. Launch your next adventure from your private dock on Miles Creek or wander to the peaceful wooded shoreline along the East River beside Zimmerman Marine. Best of all, the home is located in Flood Zone X. From the street, the classic brick Cape offers timeless curb appeal. Inside, the home unfolds into something entirely unexpected. The soaring rear elevation, walls of windows, and vaulted ceilings create a bright, airy atmosphere where traditional architecture blends effortlessly with modern and mid-century influences. Designed for everyday living and entertaining, the home offers 9 versatile rooms that easily adapt to your lifestyle. Hardwood floors, Brazilian cherry flooring upstairs, recessed LED lighting, and custom built-ins add warmth and character th

Enjoy the privacy and beauty of waterfront living on historic Winter Harbor, a peaceful haven for fishermen and boaters since colonial times. Set on 5 wooded acres, this 3-bedroom, 3-bath home offers a rare blend of natural beauty, abundant wildlife, and seclusion. The spacious family room features a cathedral ceiling, while the eat-in kitchen includes a pantry and opens to a large mudroom with a washer/dryer and full bath. The primary suite offers an ensuite bath with a double vanity, jetted tub, and separate shower. Two additional bedrooms share a hall bath. Relax on the front porch while taking in peaceful views of the water and surrounding woodlands. Fresh paint and new flooring make this home move-in ready. 2 Million approved for dredging the entrance of Winter Harbor. A wonderful opportunity to enjoy privacy, nature, and waterfront living in a truly special setting

Creekside Retreat in Mathews County Just 2 Miles from Bethel Beach. Enjoy fishing, kayaking & relaxing by the shore! Welcome to this opportunity to own a private home in scenic Mathews County Nestled on 1.4 acres. This 1860 sq ft living space, Freshly Painted charming 2-bed 2-bath home offers peaceful seclusion & sits atop spacious 4-car garage for adventure seekers with room for all your favorite recreational gear & vehicles. Primary bedroom features walk-in closet & Bath. Open living space is enhanced by large French doors in both the living room & kitchen flooding the home with natural light & leading out to a private setting balcony. Wonderful for nature lovers! Whether you are seeking a full-time residence or a weekend getaway!

Gorgeous waterfront home! Meticulously renovated waterfront home with lots of character! Gorgeous views of the West Landing creek from this 2 story colonial boasting a large foyer, formal dining and living rooms with an open concept and gas fireplace, custom kitchen with quartz counters, new appliances, and soft close cabinets throughout. First floor offers a downstairs en-suite primary while second floor offers an oversized private primary suite with access to the rear balcony. 3 additional upstairs bedrooms and full hall bathroom with double vanity. Whole home generator, new trex style decking on both rear decks, custom functional shutters. Call today to schedule your showing!

Coastal Living Near Haven Beach on Chesapeake Bay! Located in the sought-after Haven Beach area of Mathews County, this 3-bedroom, 2-bath home sits on approximately 4.85 acres and offers the opportunity to enjoy the relaxed lifestyle of Virginia's Chesapeake Bay region. Just minutes from a public sandy beach on the Chesapeake Bay and a nearby public boat ramp, this property is perfectly positioned for boating, fishing, kayaking, and enjoying the outdoors. The home features a comfortable floor plan with a living room, sunroom, utility room, and stainless steel appliances. Multiple mini-split heating and cooling units provide efficient year-round comfort throughout the home. A detached storage building offers additional space for equipment, tools, and recreational gear. The home is elevated, providing added peace of mind during coastal storms. While the property could benefit from some TLC and updating, it presents an excellent opportunity to make it your own and enjoy all that this desi

Just 3 miles from the quaint town of Mathews, this beautifully updated 1910 farmhouse blends timeless character with modern comfort. Featuring 3 bedrooms and 2 full baths, this 1,690 sq ft two-story home offers the perfect balance of history, warmth, and functionality. Inside, you’ll find gleaming wood floors, a cozy wood stove, and flexible living spaces that make it easy to feel right at home. Set on a peaceful rural property with a barn, front porch, and rear deck, this home is ideal for a family, a relaxing weekend getaway, a charming starter home, or for those looking to downsize while enjoy the serenity of the country. Ready to move in with brand new siding and exterior trim, metal roof freshly painted, newly painted interior, porch and deck

An 1800s farmhouse on two tree-surrounded acres, tucked away in privacy—yet right in the heart of historic Mathews. This remarkable 1800s farmhouse feels worlds away, yet restaurants, shops & everyday conveniences are just beyond the trees. Set on 1.99 beautifully landscaped, park-like acres, a long crape-myrtle-lined drive welcomes you home. Inside, 3680sf offers 4 bds & 3 full baths, thoughtfully updated while preserving the character that makes this home so special; original windows, stairwell & wood beams, solid maple & pine floors, custom kitchen cabinetry, updated kitchen & baths. A second rear staircase leads to 2 spacious bds, full bath & walk-thru closet, creating a versatile private wing. Enjoy the large, screened porch, aggregate patio, expansive fenced area, 4-bay pole barn, 2-car garage, storage bldg & finished cottage/studio. White Dog Bistro, Southwind Pizza & historic courthouse square are about a block away, with an East River public boat landing just 2 miles away. Ask

Welcome to this lovely cape that has been beautifully maintained and updated. All major items replaced in the last 5 yrs to include the roof, HVAC, hot water heater, plumbing, kitchen, baths, flooring, electrical. The list goes on. Sit on the back screened porch and enjoy watching nature in the large back yard. The fire pit and the 2-car detached garage offer add'l options to really create an entertaining back yard. Home is wired for a generator. This home is currently being used as a successful airbnb. Whether you are looking for a wonderful place to call home or an immediate investment, this home offers what you need. Within minutes to Mathews downtown historic district and all community shopping yet still offering a peaceful and quiet setting. Call for your private tour today

Welcome to this beautiful new construction home offering 3 bedrooms, 2.5 baths, and the perfect blend of modern comfort and small-town charm in the heart of Mathews. Enjoy peaceful country living from the inviting front porch before stepping inside to an open, light-filled floor plan designed for everyday living and entertaining. The spacious kitchen features an air fryer stove, abundant cabinetry, and plenty of workspace for the home chef. A versatile 15x20 bonus room provides endless possibilities for a home office, playroom, or media room. Energy-efficient split HVAC systems offer year-round comfort, while the rear deck overlooks the generous 0.61-acre lot—ideal for relaxing, gardening, or outdoor gatherings. Don't miss this opportunity to own a brand-new home in a desirable country setting with all the conveniences of town just minutes away

This listing includes a main 4 bedroom waterfront'estate style' home and a large waterfront 2 bedroom guesthome. This includes an attached 2 car garage and a separate large garage and a separate large storage building and also a 3 bedroom house with attached garage. And a (2) two bedroom rental homes plus a 5 acres (used to be business property) with a office and a pole barn/greenhouse also is leased. There is room to build more dwellings there or makes a great horse property with a possible horse barn conversion. This unique 10+ acre waterfront property has a renovated Farmhouse style four bedroom main home plus BRAND NEWLY RENOVATED 2 Bedroom WATERFRONT Guesthouse, and includes 3 income producing rental homes, and a rented 32'x100 pole barn. Five (5) Homes convey total. This property features beautiful views on 3 sides with 475' of shoreline, a deep water pier and boat lift with quick access to the Eastriver. Great fishing and crabbing. Gazebo, two waterside patios, and fire pit. Thi

Discover serene waterfront living at its finest in this beautifully maintained 4BR, 3BA ranch home. Nestled along the peaceful Stutts creek w/water views from multiple rooms, this single-level gem offers effortless one-level living and an inviting open-concept floor plan perfect for everyday comfort & effortless entertaining. Step inside to expansive living spaces bathed in natural light, where the open layout seamlessly connects the kitchen, dining area, & family room. The sunroom is the highlight—a tranquil oasis overlooking the creek, ideal for morning coffee, quiet reading, or hosting sunset gatherings. With 4 generously sized BR and 3 full bathrooms, there’s plenty of room for family, guests, or a home office. Outside, the private pier invites you to cast a line, launch a kayak, or simply relax by the water’s edge. Enjoy direct creek access & panoramic views that bring the beauty of nature right to your doorstep

Lovely home, no flood zone. Living room, den, formal dining room with bar and open kitchen with eat at bar, utility room, large master suite with garden tub, laminate wood flooring and carpet in master bedroom, large front and rear decks, front paver patio, detached 4 car carport with partially finished room above has duct work and electrical, double width driveway on private road. Approved reverse mortgage short sale. Built in Equity

Nestled along Rowes Creek, this waterfront home offers the perfect blend of comfort, functionality, and waterfront living. Built in 2017, the home features 3 bedrooms, 2.5 baths, beautiful hardwood flooring, granite countertops, and a spacious open-concept layout designed for everyday living and entertaining. The living room features a gas fireplace and opens to a large covered back porch overlooking the water, complete with low-maintenance composite decking. The primary suite also offers direct access to the porch, creating a private retreat with peaceful waterfront views. Upstairs, a large loft with water views provides additional living space. Boaters will appreciate the private pier with pilings already in place for a future boat lift. The fenced backyard offers added privacy, while the conditioned 3+ car attached garage is equipped with a mini-split system and provides ample space for vehicles, storage, hobbies, or a workshop. Conveniently located on Rowes Creek with easy access t

Come see this fabulous completed new construction 4 bed/3 full bath home on more than 6 acres! Built by a reputable Class A builder, with a focus on quality and modern convenience, it includes many features normally skipped by builders: plentiful recessed lighting, garage door opener, ceiling fans, a backsplash, and ceiling-height tile showers in all baths. There are 3 bedrooms on the first floor, including the primary suite. The open floor plan features a custom kitchen with all wood shaker cabinetry, granite counters, under cabinet lighting, and stainless steel appliances. The upstairs loft includes another bedroom and full bath, and a loft area for working from home. Imagine entertaining on the spacious composite deck overlooking the large, level lot. Less than 10 minute from downtown Gloucester. Eligible for up to 1% closing cost assistance with use of builder's preferred lender

Come see this fabulous completed new construction 4 bed/3 full bath home on more than 6 acres! Built by a reputable Class A builder, with a focus on quality and modern convenience, it includes many features normally skipped by builders: plentiful recessed lighting, garage door opener, ceiling fans, a backsplash, and ceiling-height tile showers in all baths. There are 3 bedrooms on the first floor, including the primary suite. The open floor plan features a custom kitchen with all wood shaker cabinetry, granite counters, under cabinet lighting, and stainless steel appliances. The upstairs loft includes another bedroom and full bath, and a loft area for working from home. Imagine entertaining on the spacious composite deck overlooking the large, level lot. Less than 10 minute from downtown Gloucester. Eligible for up to 1% closing cost assistance with use of builder's preferred lender

Welcome home to 3070 Friends Road! Situated in a quiet, established Hayes neighborhood just 10 minutes from the Coleman Bridge, this 3-bedroom, 1-bathroom residence blends coastal proximity with exceptional value. Inside, you'll find a bright, welcoming living area flowing into a spacious eat-in kitchen complete with ample cabinetry and storage. Outside, relax and catch the fresh breeze or take in the nearby water views

Rare waterfront opportunity in Mathews County! Situated on 2.23 acres at the tip of a peninsula between the Piankatank River and Queens Creek, this property offers approximately 400 feet of shoreline and sweeping views across Hills Bay toward the Chesapeake Bay, with Milford Haven and Gwynns Island nearby. This custom Cape-style home offers a thoughtfully designed layout featuring a main-level primary suite, formal living and dining rooms, a spacious family room, and an eat-in kitchen. A private office with a full bath provides flexible living options. Enjoy multiple covered porches that capture beautiful water views, plus an unfinished basement with direct garage access—offering excellent storage

Beautifully remodeled home in Gloucester! New! New! New! Hardwood and tile flooring throughout. Kitchen is bright & open. You will love the white cabinets, granite countertops and ss appliances. 2 bedrooms plus a flex room for office, study or overnight guests. New hvac w/nest thermostat. New windows. Primary bedroom is spacious with walk-in closet, private bath with shower/tub and double vanity. A definite plus is the huge floored attic heated and cooled. Great for storage and more. Enjoy time outdoors with a front and back deck. Double detached outbuilding (18x20) has power and space for workshop. You still have 15x15 addition for yard equipment and extra storage. A ton of possibilities! Minutes from public boat landings. Make your plans to see this one today!

Classic 1953 bungalow charm meets a complete renovation! Set on 1.03 open acres just 6 miles from the heart of Mathews, this 2-bedroom, 2-bath home has been thoughtfully renewed while retaining touches of its original character, including beautifully refinished hardwood floors and original doors. Improvements include a new roof, vinyl siding, windows, septic system, 4 mini-splits, updated electrical, new lighting and a completely renovated kitchen with white Shaker cabinetry and stainless steel appliances. The original bath was completely remodeled and a second full bath added to create a private primary suite, complete with two walk-in closets. A spacious dining room opens to the kitchen, while a concealed laundry closet accommodates a full-size stackable washer/dryer. Outside, enjoy a new side deck, large rear concrete patio, circular double-width gravel driveway, fresh landscaping, mature trees and fruit trees. Move in and start enjoying coastal life of Mathews!

Seller concessions available with an acceptable offer! New Septic System. POV: I’m the back deck at 9509 Line Fence Road, & I might have the best seat on the property. From here, mornings begin with coffee while sunlight stretches across the open land, & evenings end surrounded by mature trees and the kind of privacy that lets you finally exhale. I sit just outside both the kitchen & primary suite, ready for weeknight dinners, slow weekends, & gatherings that last longer than planned. Inside you’ll find a home that has been given a fresh start. The kitchen is bright and open, with new cabinetry, quartz countertops, stainless steel appliances, & an oversized island made for cooking, conversation, & everything in between. The living and dining areas flow together easily, while the primary suite offers its own peaceful escape with a beautifully renovated bath & oversized tiled shower. Out front, new board-and-batten siding, black windows, a new roof, & new HVAC bring modern style & peace

Welcome to your private fifteen acre sanctuary at 9632 Rowes Point Road. Originally built in 1900, this classic single family home has been completely remodeled from top to bottom, seamlessly marrying historic character with pristine, contemporary updates. Step inside to a bright, open interior featuring over 2,000 square feet of updated living space. The gourmet kitchen comes equipped with brand new stainless steel appliances, premium cabinets, and elegant quartz countertops. Infrastructure updates include a brand new roof on all buildings, new vinyl windows, a new water heater, and a water treatment system. The acreage features freshly cleared forestry mulched trails winding through the wooded portion of the property. The exterior also includes a large, detached two car garage with mechanic's pit and a workshop. Enjoy a quiet, rural escape just minutes from public boat landings. This stunning remodel is ready for you. Some pictures are virtually staged (AI generated)