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Eastern Shore of Virginia Real Estate – Chesapeake Properties Listings

Following is a list of the real estate listings being offered by Chesapeake Properties real estate agents. You may also find the following pages helpful:

If you have questions about Eastern Shore real estate, please do not hesitate to reach out to one of our Chesapeake Properties team members and we would be happy to help you!

MT. PLEASANT CIRCA 1759 a 175 +/- ACRE LEGACY WATERFRONT ESTATE ON VA'S EASTERN SHORE. THIS PRIVATE SEASIDE PROPERTY WITH APROX. 1342 FT OF SHORELINE ON THE PRISTINE WATERS OF HOLT CREEK HAS A TNC CONSERVATION EASEMENT FOR SECLUSION AMIDST FIELD, FORREST, TIDAL MARSH, WETLANDS AND WILDLIFE. PREMIERE SETTING FOR SPORTSMAN LOOKING FOR OUTSTANDING HUNTING, HORSE FARM, VINEYARD & OR OYSTER FARM(AQUACULTURE). HOLT CREEK LEADS TO THE ATLANTIC OCEAN AND THE BARRIER ISLANDS. THE PROPERTY HAS A 2800 X 60 FEET GRASS AIRSTRIP WITH AIRCRAFT HANGER GARAGE. UNIQUE OPPORTUNITY TO RESORE ONE OF THE LAST EASTERN SHORE HISTORIC ESTATES. TRULY A SPLENDOR OF A BYGONE ERA. LOCATED ONLY 15 MINUTES FROM CAPE CHARLES AND 1 HOUR FROM NORFOLK INTERNATIONAL AIRPORT.

$1,500,000 Active

14121 Seaside Rd 38 Machipongo, Virginia

This 3 bedroom 2 bath Cape Charles classic is nestled in the heart of the historic district as the personal home of one of the country's leading fine leisure living designer.With successful experience feature on the national stage & prominent publication like Architectural Digest, the owner brought his expertise & sensibilities to the gem of a home. Finely finished with an expertly crafted garden patio, this property is everything you would want to add to your life to be comfortable putting your feet up or entertaining special guests. Costume build kitchen with Italian imported glass doors, soap stone countertops, high end appliances, original hardwood floors, handcrafted build-ins, relaxing screened in back porch, a separated cottage with a golf cart garage & FULLY FURNISHED.

$795,000 Active

548 Madison Ave 257 Cape Charles, Virginia

3 Beds 2 Baths 1,720 SqFt

Cape Charles circa1930 Four Square in historic district. This spacious 4 bedroom home has handsome pine floors, original moldings & stately double staircase. Southern style front porch overlooks Marina Village ponds. Lovely views of Chesapeake Bay & stunning sunsets are viewable from front porch & upstairs bedroom! This beautifully appointed 4 bedroom home is currently a lucrative vacation rental. New roof & HVAC in 2021. Located on full size lot w/ plenty of mature plantings.The extra wide sidewalks on Washington Ave feature old fashioned street lights & are perfect for strolling..just a short walk or bike ride to the beach. Cape Charles is a golf cart friendly town,shopping, restaurants, galleries, beach, marinas, and central park w/Saturday night summer concerts & playground close by.

$750,000 Active

618 Washington Ave 17 Cape Charles, Virginia

4 Beds 2 Baths 1,472 SqFt

Location..location..location..2 Blocks to BEACH on treelined Tazewell Ave. This Duplex used to be a grand single family home. Property is in need of some TLC.. Great opportunity to restore this home to it"s former Glory. Ample alley access in the back for off street parking and accessory dwelling unit. Lovely shaded backyard. Live in one side while working on the other.. Great income potential for vacation rentals. Homes in this coveted location do not come on the market very often.. Short walk to downtown restaurants, shops, galleries and Strawberry Plaza with live outdoor music in the summer. Central Park is just around the corner.

$575,000 Active

215 Tazewell Ave 412 Cape Charles, Virginia

4 Beds 3 Baths 2,456 SqFt

3 bedroom waterfront home located in Vaucluse Shores a beautiful and established waterfront community, with community pool, tennis, boat ramp and beach. This home has a private dock with great boating depth leading to the Chesapeake Bay. The dock has water and electricty. The house has a spacious living room with open floor plan and lots of natural light. The sunroom and deck overlooks the private boat dock located on Hungers Creek. The kitchen has lots of cabinet space. Attached garage. The roof is about 7 years old. The HVAC system is about 6 years old. Great opportunity to own a waterfront home for a good price! Located about 20 minutes from Cape Charles.

$479,000 Active

3197 Black Drum Ln 189 Machipongo, Virginia

3 Beds 2 Baths 1,800 SqFt

Fantastic opportunity to own this 3 bedroom/2bath condo just steps from the community pool. This condo comes with many extras!!! Fully furnished including TV's, stereo, grill, artwork, linens, bedding & much more. GOLF CART INCLUDED WITH MANY EXTRAS!!! Open floor plan living with a balcony. Granite countertops & oak cabinets in the kitchen. Spacious 2 car garage currently set up for entertaining. Bay Creek is a master planned, gated community situated on Virginia's Eastern Shore. Amenities include: 2 signature golf courses, private beaches, pools/tennis courts and restaurant. Walking/biking paths throughout community and pool is within steps of condo. Historic Cape Charles and nearby Kings Creek Marina. Golf Cart friendly community! 40 Minutes from the Norfolk International airport.

$435,000 Active

721 Prestwick Turn 721BO Cape Charles, Virginia

3 Beds 2 Baths 1,538 SqFt

Cape Charles luxury condo w/ designer touch, has open concept living. Condo is in a 4 unit building which was completely rehabbed in 2021. Professionally decorated & completely furnished this home is already used as a vacation rental. This condo has reclaimed wood floors, clean lines & plenty of light. Kitchen has quartz countertops, attractive tile backsplash w/ shaker cabinets & stainless steel appliances. This 2 bedroom, 2 bath unit has an expansive living area & a bonus study/office. Common area includes large storage closet for Amazon deliveries, bike & beach gear storage, outdoor enclosed shower, private patio, 2 parking spaces & a charging area for golf cart. Cape Shore Condos is a 4 unit association. Vacation Rentals are permitted! Close to beach, shopping, restaurants and marina.

$420,000 Active

730 D Randolph Ave Cape Charles, Virginia

2 Beds 2 Baths 1,184 SqFt

BEAUTIFUL SECOND FLOOR MODEL CONDO. PERFECT SETUP FOR RENTAL PROPERTY. LUXURY LIVING ALL ON ONE FLOOR. PRIVATE AND SPACIOUS AT THE SAME TIME. FEATURES 1538 SQ FT. OF LIVING SPACE WITH 3 BEDROOMS AND 2 FULL BATHROOMS. CLOSE TO FAIRWAYS POOL. BAY CREEK IS A MASTER PLANNED, GATED COMMUNITY SITUATED ON VIRGINIA'S EASTERN SHORE. BAY CREEK OFFERS GOLF, 2 MILES OF PRIVATE BEACH,TENNIS COURTS,COMMUNITY POOL. GOLF CART FRIENDLY! SHORT RIDE TO HISTORIC CAPE CHARLES AND NEARBY KINGS CREEK MARINA. GOLF CART FRIENDLY! BEACH CLUB SPORTS MEMBERSHIP INCLUDED!!! Mandatory membership attached to deed. 10K value.

$399,000 Active

704 Prestwick Turn 704BO Cape Charles, Virginia

3 Beds 2 Baths 1,538 SqFt

Cape Charles FIXER UPPER with a GOOD ROOF! This Victorian beach cottage has been gutted and taken down to the studs. Perfect opportunity to make this charming cottage your own. Plenty of space in the back for addition. New electric service was installed a few years ago. Original pine floors are intact. Lovely location on treelined street where many of the homes have been impeccably renovated. Water and sewer tap fee is intact. Spacious backyard. Close to beach, restaurants, shopping and marinas.

$217,000 Active

624 Jefferson Ave 124A Cape Charles, Virginia

2 Beds 1,378 SqFt

This exquisite waterfront farm has been preserved and is the definition of Tranquility. The farm boasts approximately 2500 feet of water frontage on Craddock Creek with 54.61 acres of land. 48 acres are tillable with Bojack soil currently used for farming and brings in $4900 per year. If you have been looking for the perfect place for your family retreat or home, a recreational property for horses then this is it! This is a once in a lifetime opportunity to own your piece of heaven on earth! Enjoy complete privacy, beautiful views and abundant wildlife. Great kayaking & boating right in your backyard! This is a once in a lifetime opportunity to own your piece of heaven on earth! Located about 1.15 hour from Norfolk international airport 3.5 hours from DC, Baltimore area. 2.5 to Richmond

$769,000 Active

Scarboroughs Neck Rd 57 Belle Haven, Virginia

54.610 Acres

BEST VIEW IN CAPE CHARLES!! Waterview building site with colorful sunset views & Views of Kings Creek Marina in Bay Creek's Marina Village East. Great investment opportunity.. there is no time frame requirement to build but if you are interested in building, please contact listing agent for information on Builder's Guild and Architectural Guidelines. Community amenities include 1 Signature Golf Course-27 holes. Pro Shop, Restaurant, 2 mile Private Beach and Community Pool/Tennis Courts. Bay Creek also offers a members only, Beach Club and Fitness Center. Historic Cape Charles and Kings Creek Marina are within walking distance of this homesite. Golf cart friendly community!

$299,000 Active

LOT 9 Waters Edge Drive 9 Cape Charles, Virginia

1 Acres

If you are looking for tranquility and peacefulness this beautiful waterfront property is perfect! Waverly Landing Estate is a very private waterfront community and this lot is located at the end of the street in the cul-de-sac. Wide open views of Hungers Creek. This community has a boat dock and a boat launch but there is plenty of room to build your own dock right in your back yard.

$239,000 Active

Lot 1C Park Lane 1C Machipongo, Virginia

2.500 Acres

Gorgeous oversized homesite overlooking the 6th hole on Palmer Course in Bay Creek's Heron Pointe Village. Heron Pointe is a neighborhood of luxurious estate homes on spacious lots surrounded by the natural beauty of several lakes, Old Plantation Creek and the Chesapeake Bay, as well as the landscaped greens of the Arnold Palmer Signature golf course. A refreshing waterfall and lovely gardens welcome you into the community. Bay Creek amenities include a community pool, tennis, and a private white sandy beach. Sports (state of the art fitness center) and golf memberships are available as well.

$235,000 Active

143 Heron Pointe Dr 28 Cape Charles, Virginia

0.450 Acres

30.64 acre hamlet with 0.5 acre zoning. Currently divided into 13 lots but could be divided further. This property has road frontage on Sylvan Scene road on Seaside Road and an access road to the back of the property. Great opportunity to develop. 11 lots are divided between 1.01 and .35 acres. Two of the larger parcels can be further divided. One of the larger lots is 11.49 acres and the other is 8.43 acres. Both could be divide in to 0.5 acre lots. This is a rare opportunity to own a development that is approved as a residential hamlet. All 13 lots have perk test certification letters. Located 15 minutes from Cape Charles.

$180,000 Active

Sylvan Scene Dr Machipongo, Virginia

30.640 Acres

Southern Exposure building lot in Cape Charles is just 6 blocks to the beach! Located in the heart of the historic beachfront town of Cape Charles. A golf cart friendly town where you do not have to get in your car once you arrive. Close to the town's central park to enjoy the town's festivities. Build your dream home and enjoy all of the town's many amenities; tennis courts, fishing pier, sand beach, boat ramp and marina. Water/sewer fees are additional expense. House plans must be approved by Historical Review Committee in Cape Charles.

$175,000 Active

Madison Ave 134 Cape Charles, Virginia

RARE FIND! Full size building lot on Jefferson (40 x 140). 5 blocks to the beach! Water/sewer fees are additional expense. House plans must be approved by Historical Review Committee in Cape Charles.

$165,000 Active

537 Jefferson Ave 31 Cape Charles, Virginia

0.129 Acres

Panoramic views from this gorgeous lake front lot in Marina Village East. Perfect spot to build your Coastal home.. great investment opportunity.. Community amenities include a 27 hole Signature PGA Golf Course, Pro Shop, Preserve Trails, Coach House Restaurant, 2 mile Private Beach and Community Pool/Tennis & Pickle Ball Courts. Bay Creek also offers members only, Beach Club and Fitness Center. Historic Cape Charles with town beach, harbor, boat ramps, shopping, restaurants, galleries, & concerts in the park thru out the summer are just a golf cart ride away. Kings Creek Marina is conveniently located next to this community.

$135,000 Active

38 Bridgeton Drive 45 Cape Charles, Virginia

0.220 Acres

Waterfront lot in upscale waterfront community located on quiet cul-de-sac. 20 foot elevation, not in flood zone. Over 200 feet of quiet waterfront with lots of waterfowl. Lot has been approved for 50' foot setback(but should be verified). Easily accessible community deep water boat ramp and picnic area. Bring your Whaler, Skiff, or fishing kayak and enjoy terrific striper fishing on Hungars Creek and outstanding flounder fishing on Virginia's Barrier Islands. Wide streets for biking and walking. Several local wineries near by to enjoy.

$105,000 Active

Lot 17 Wilsonia Shores Dr 17 Machipongo, Virginia

0.860 Acres

5 acre home site walking distance to private sandy bayfront beach, a perfect setting to build a custom home away from the hustle and bustle of town life. Certification letter on file for a 7 bedroom home. Deeded access to Chesapeake bay beach and Westerhouse creek. Peaceful and scenic setting surrounded by nature and wildlife. A short drive away from historic Cape Charles.

Sunset Shores Drive 7B Machipongo, Virginia

5 Acres

Large Home site on cul-de-sac in Bay Creek's Signature Village. Attractive setting with trees at the back of the lot. Beautiful vista of green grass and trees make for a bucolic setting. Historic Cape Charles is just just a golf cart ride away. Beach, marinas, shopping & restaurants. Easy access of all of Bay Creek's amenities, such as the Pro Shop, two Signature Golf Courses, tennis courts, swimming pools, 2-mile private Beach, and the members-only Beach Club and Fitness Center. All of these are easily within walking distance or a short golf cart ride.

Lot 73 Seay Ct 73 Cape Charles, Virginia

0.345 Acres

Expansive 5 acre lot in the established community of Wilsonia Plantation that offers a private boat ramp on deep water with easy access to Chesapeake Bay. There is also a covered picnic area for all the residents to enjoy. A tranquil location with mostly large lots for added privacy. Conveniently located a short distance away from historic Cape Charles with its beautiful sandy beach, lots of shops and restaurants with fun and exciting events year round. A boater's dream as the boat launch is literally round the corner. This home site is cleared and ready for your building plans. Very reasonably priced in todays escalating market.

Lot 10 Wilsonia Dr 10 Machipongo, Virginia

5.010 Acres

Bay Side Dr 1 Greenbush, Virginia

1.480 Acres

3.5 wooded acres close to Route 13, 2 parcels with frontage on Trehernville Dr and Mark Lane. There is an old shed on front corner of the property. There are two parcels that convey with this sale and there are no deed restrictions

Treherneville Dr E &F Birdsnest, Virginia

3.500 Acres

2 (.5 acre) building parcels in Nassawadox area just off Franktown Rd. Old home recently taken down on front parcel. Great opportunity for 2 building parcels.

9431 Franktown Rd 79 & Nassawadox, Virginia

1 Acres

1 half acre building lot in the town of Guilford. Priced to sell.

Lot 33 Winterville Rd 33 Bloxom, Virginia

0.500 Acres

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