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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!

Verandah Bay- one of the original spectacular showcase homes of Bay Creek. 3/4 acres of expansive & magnificent views of Chesapeake Bay & holes # 2 & 3 of Arnold Palmer Signature Golf course. Designed by William Poole to have the look & feel of an early century Eastern Shore manor house. As you enter this captivating 7000sqft home you feel immersed in a sense of rich grandeur with large windows & exquisite trim and several areas for gracious entertaining. Among the notable features is the reclaimed wood flooring in living area & the impressive chef kitchen with classic marble center island & Viking appliances. All bathrooms & kitchen feature exclusive New Ravenna mosaic creations. Over 3000sqft of outdoor living space overlooking tastefully landscaped garden and magical lighting

$2,349,000 Active

2 Heron Ct 44 Cape Charles, Virginia

4 Beds 7 Baths 7,000 SqFt

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

BAY FRONT COASTAL HOME W/ WHITE SANDY BEACH ON 5 ACRES! Enjoy watercolor sunsets & bay breezes from this 4200 sq ft home w/ panoramic views of the Chesapeake Bay, Westerhouse Creek & your own fresh water pond. Over 510 feet of Bulkhead, protected shoreline, & private beach. Set up as a 5 bedroom & 3.5 baths, Parlor/game room, Open Kitchen w/ Cherry Cabinets, farm house sink & wine cooler. Deck off the great room offers perfect a view of evening sunsets over the water. Boathouse to store all your recreational water toys & more. Electric installed for future addition of a boat lift. The new steel/wood spiral staircase leads to a cupola giving you 360 degree view. Most of the furniture conveys. Please view the videos to see all this home has to offer! CERTIFIED NOT IN FLOOD ZONE!

$1,490,000 Active

9454 Westerhouse Rd 3 Machipongo, Virginia

4 Beds 4 Baths 4,277 SqFt

Gracious American Foursquare Home, Circa 1920, with oversized frontporch, welcoming grand foyer, & stately staircase. Large sun-filled rooms with high ceilings, original moldings, pocket doors, & hardwood floors throughout. A well-planned kitchen with ample storage leads to the spacious dining room with original fireplace. Finished 3rd floor bedroom & full bath. To the back of the house is a 2 bedroom 1 bath apartment that could be easily closed off & used as an owners suite. Lush gardens and a private deck surround the property. The 60 ft wide back yard has ample space for off-street parking. Short walk to beach, shopping & marinas in our historical golf cart-friendly town. Operated as a short-term rental with very lucrative income. More info available upon request.

$1,124,000 Active

202 Madison Ave 318 Cape Charles, Virginia

6 Beds 6 Baths 3,167 SqFt

WATERVIEW/SUNSETS-Breathtaking views from the crow's nest of this “Cayman” design coastal home in Kings Bay Professionally designed & landscaped home has 10 ft ceilings downstairs & plenty of light! Easy walk to private beach access, this home has open concept floor plan w/ 1st floor primary suite w/ access to covered porch. Family room has fp & sliding glass doors to lavishly landscaped backyard. Kitchen has lovely light filled dining nook, ample cabinets & additional seating at the bar. 2nd floor has 3 bedrooms & 1 1/2 baths. 3rd floor crow's nest has ample room for seating w/ panoramic views of bay. Bay Creek amenities include private white sand beaches, pool, tennis & Pickelball courts. Sports & Golf memberships available. Kings Creek Marina is short walk or easy golf cart ride away!

$899,000 Active

18 Kings Bay Drive 180 Cape Charles, Virginia

4 Beds 4 Baths 2,718 SqFt

This 3 bderoom 2.5 bath home offers the best of both worlds, nearly new constraction in the heart of historic Cape Charles. Built in 2018 makes this home modern & low maintains located just steps from the beach. Off street parking with a detached garage and an entertainment room next to it. The house has lots of natural light and a coastal design. The primary suite is located on the first floor. Fenced in back yard. This home is truly the perfect beach get-away! Comes fully furnished. The house is currently used as a vacation rental.

$815,000 Active

526 Strawberry St D Cape Charles, Virginia

3 Beds 3 Baths 1,332 SqFt

Circa 1920 charming craftsman style 2 bedroom 2 bath cottage is a perfect beach getaway! Great curb appeal with cedar-shake siding. Fantastic location overlooking the tow park. Enjoy the summer concerts sitting right on your front porch. Easy one-story living. Original Hardwood floors, wood trim & fireplace. Back deck, large shed with a concrete pad for off street parking. Fenced in back yard. Closed to beach, park, down town shops & restaurants. Sold fully furnished! It is a vacation rental and has great income!

$732,000 Pending

1 Park Row 293 Cape Charles, Virginia

2 Beds 2 Baths 1,170 SqFt

Light filled single story ranch home in Tower Hill w/ 1911 sq ft was built in 2023. Property & home are in immaculate condition. Open concept living area is spacious w/ vaulted ceilings & handsome luxury vinyl plank flooring. Gas f/p in the living room makes for cozy evenings w/ family & friends. Kitchen has ample cabinetry & convenient kitchen bar. Owner's suite is spacious & has big walk in closet & large private bath. Enjoy back porch overlooking private yard. This lovely home is just outside Historic Cape Charles w/ white sandy beaches, 2 marinas, restaurants, shopping, & galleries. Cape Charles & Oyster boat ramps are only a few minutes away. Ideal for boaters, fishermen & beachcombers! 45 minutes to Norfolk & VA Beach.

$435,000 Active

22217 Kings Creek Pkwy 5 Cape Charles, Virginia

3 Beds 2 Baths 1,911 SqFt

Location ..Location ..Location. Immaculately kept condo 3 blocks to the beach in the center of Historic District! Only 4 condos in this beautifully renovated historic building. This unit is on the 2nd floor w/ light filled southern exposure w/ covered porch overlooking Cape Charles Central Park. Condo has tall ceilings, beautiful pine floors, granite counter tops, gas fireplaces, handsome moldings, tall windows & open concept floor plan. Primary bedroom opens out onto covered porch with panoramic view of town & Central Park. Upstairs bedroom & bath has plenty of closets and light filled nook looking out over the park. Condo has lots of storage w/ additional storage compartments in the basement. Plenty of off street parking in the back off of Madison Avenue. Bring your golf cart

$425,000 Pending

11 Park Row 288 D Cape Charles, Virginia

2 Beds 2 Baths 1 SqFt

Three (3) bedroom Cape Cod-style home in a very private setting on large wooded lot located in a neighborhood with spacios lots. The interior is a very comfortable lay-out with galley kitchen, with a family room with cozy woood stove on one side and breakfast room on the other. A slider leads out to a large deck and hottub. The back yard is a gem of unlimited possibilities that already has a firepit and a large two story barn, suitable for anything from storage to an entertainment space.

$369,000 Pending

8203 Denwood Rd 2& A1 Franktown, Virginia

3 Beds 3 Baths 2,058 SqFt

This two bedroom beach cottage is perfect for your summer get-away. Walk down your private steps on to the beach. It comes fully furnished, with a fully exquiped kitchen, laundry room, hot tub overlooking the Chesapeake Bay. Located just ten minutes north of Cape Charles. This home is on a land lease!

$275,000 Active

16342 Smith Beach Rd Eastville, Virginia

2 Beds 1 Baths 930 SqFt

$139,500 Active

18167 Meadows Dr 5 Cape Charles, Virginia

3 Beds 1 Baths 1,012 SqFt

900ft of Chesapeake Bay frontage doesn't even begin to describe this priceless gem colored with an endless supply of our famous sunsets. This 30.5 acre property comes with abundant privacy, endless wildlife and an amazing combination of old growth trees and cleared land. With 1,640 feet of shoreline on Costin's Pond, the property is one of the more unique properties on the Eastern Shore, bordered on the North and West by water. While the private drive ensures your irreplacable piece of nature is yours, and yours alone, you're only 10 minutes from the classic town of Cape Charles and a mere 25 minutes to all the amenities of Virginia Beach. This Eastern Shore of Virginia property defines the idea of a getaway with access to all the things that make life good.

$1,700,000 Active

Arlington Chase Rd 6 Cape Charles, Virginia

30.49 Acres

Chesapeake Bay waterfront/beachfront lot w/200 feet of water front. Fully bulkheaded w/ rock rip rap. Evening sunsets & delightful summer breezes will be yours to enjoy from this tranquil setting. Well and septic are already in! Community amenities include pool, nature trails and private beach access. Boat ramps are close by!

$269,000 Active-Under Contract

lot #19 Peaceful Pond Dr 19 Jamesville, Virginia

1.89 Acres

Located in Bay Creek's Colony Village, this lovely homesite is overlooking Crystal Lake and just steps away from the Chesapeake Bay. Build your dream home with beautiful views of the water. From here, you are a quick golf cart ride away from Historic Cape Charles and all of Bay Creek amenities, including the 27 holes of golf, 350-acre Nature Preserve, 2-mile private beach, and the members-only Life Center.

$239,000 Active

118 Sunset Blvd 40 Cape Charles, Virginia

0.25 Acres

Wonderful opportunity to live in the desirable waterfront community of Butlers Bluff. Two acres with access to the beach. Seller is including with this sale the adjacent lot which is not buildable but is a buffer area adding privacy and landscaping possibility. The back of these lots border with conservation land that will never be developed or cultivated. A very established community with easy access to Virginia Beach and close to historic Cape Charles. Next to Kiptopeke State Park that offers awesome walking and biking trails, picnic area, fishing pier, boat launching facility. Abundant wild life and quiet and peaceful area with mostly year round residents.

$130,000 Active

Lot X Butler's Bluff Dr Lot X Cape Charles, Virginia

2 Acres

Lake front building site w/southern exposure has panoramic water views in Marina Village in BayCreek. Generously sized lot in The Colony has long water views looking out towards the Chesapeake Bay w/ colorful sunsets. Short walk or golf cart ride to private beaches in this gated community. Kings Creek Marina is just around the corner with Oyster Farm Restaurant and C-Pier. Memberships available in Bay Creek for golf and sports/social memberships. Access to The Preserve Nature Trails and Coach House Tavern bar/restaurant. Bay Creek has community pool and Tennis & Pickle ball courts. Cape Charles Historic district w/ shops, galleries, restaurants, theater and Central Park is just a gof cart ride away. Build now or hold for investment!

$129,000 Active

7 Colony Dr 115 Cape Charles, Virginia

0.181 Acres

Beautiful waterfront building site with scenic views of pond and Kings Creek Marina. Community amenities include Signature PGA Golf Course, Pro Shop, Restaurant, 2 mile Private Beach and Community Pool/Tennis Courts, nature trails. Bay Creek also offers members only, Beach Club and Fitness Center. Historic Cape Charles and Kings Creek Marina are within walking distance of this home site. Golf cart friendly community!

14 Charlestowne Drive 80 Cape Charles, Virginia

0.25 Acres

High elevated home site in very desirable waterfront subdivision of Butlers Bluff. This community is established with year round residents and very conveniently located close to the Chesapeake Bay Bridge. The community is located next to the Kiptopeke state-park which offers beautiful beaches and nature trails. Bike trail near by, only 10 minute drive to the historic town of Cape Charles.

$69,000 Pending

Butler's Bluff Dr 43 Cape Charles, Virginia

1 Acres

3.026 Acre building lot in Creek Bluff has good elevation and rich soils. Creek Bluff is an upscale waterfront community in a prime location mid county on VA's Eastern Shore. Close to Morley's Wharf boat ramp on the Bayside and just a short distance to Willis Wharf boat ramp on the Seaside. This lot is priced to sell!

Creekside Dr 22A2 Belle Haven, Virginia

3,028 Acres

Maximize your business visibility! This commercial lot is in a prime location on the southbound side of Rt 13, the main route to VA BEACH, OBX, CHINCOTEAGUE, and more, presents an outstanding investment opportunity. This vacant lot, formerly home to the Captains Deck Restaurant before a fire, is strategically positioned in front of the Budget Inn. Please be aware that the Seafood Shack currently operating on the property is not part of the sale.

7130 Lankford Hwy Nassawadox, Virginia

27,930 SqFt

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