Pending Listings in Southern Chesapeake, VA

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CONTINGENT3D WALKTHROUGH

ABOUT THIS HOME
Pending Listing in Southern Chesapeake, VA:
Welcome home to 809 Checkerspot Way, an exceptional 6-bed, 3-bath home located in sought-after Dominion Meadows! Built in 2019, this spacious property offers over 3,900 sq ft of modern living with a bright open-concept design. The gourmet kitchen features a large island, custom cabinetry, granite countertops, stainless appliances, and walk-in pantry. Enjoy flexible spaces including a first-floor bedroom and full bath, dedicated office, and a cozy family room with gas fireplace. Upstairs you’ll find a luxurious primary suite with tray ceiling, spa-style bath, and oversized walk-in closet. The fenced backyard, covered patio and in ground salt water pool are perfect for entertaining! Jus

$735,000

6 beds3 baths3,943 sq ft

809 Checkerspot Way, Chesapeake, VA 23323

Custom cabinetry • Stainless appliances • Gourmet kitchen

CONTINGENT

ABOUT THIS HOME
Pending Listing in Southern Chesapeake, VA:
Escape to serene country living just minutes from the city! These charming log-style homes sits on nearly 5 acres acres in Pleasant Grove and features 4 bedrooms and 3 bathrooms. This equestrian-ready property features 4 stalls, 2 run-ins, a round pen with a shed tack room & a chicken coop—perfect for horse lovers or hobby farmers. A separate 1-bedroom, 1-bath guest house includes a full kitchen and living room with new LVP flooring (being replaced this coming weekend)—ideal for guests, extended family, or rental income. The spacious wraparound porch in the back is perfect for relaxing & taking in the peaceful views. Located on a lightly trafficked, country road yet

$700,000

4 beds3 baths1,932 sq ft

2820 Bunch Walnuts Rd, Chesapeake, VA 23322

2 run ins • Guest house • Round pen

CONTINGENT

ABOUT THIS HOME
Pending Listing in Southern Chesapeake, VA:
ASSUMABLE VA LOAN AT 3% INTEREST. 3 Acres! Amazing custom 3,420 SF home boasts of 4 spacious BR/3.5 BA and features 1st & 2nd floor primary en-suites offering walk-in showers and relaxing soaking tubs. Massive 19' x 12' flex space is perfect as a bonus room or 5th bedroom. Eat-in kitchen and all bathrooms feature upgraded granite countertops and vanities; durable LVP flooring throughout the 1st floor; cozy gas fireplace in den; formal dining room for gatherings and entertaining. Outdoor living is elevated with a covered front porch, back porch, deck, and fenced backyard. Also included is a 2-car attached garage; panel wired for generator; 3-bay detached garage with electricity, 50 AMP

$915,000

4 beds3.5 baths3,420 sq ft

2508 Sanderson Rd, Chesapeake, VA 23322

Soaking tubs • Flex space • Walk-in showers

CONTINGENT

ABOUT THIS HOME
Pending Listing in Southern Chesapeake, VA:
Welcome to Gum Tree Farm – a rare 45-acre countryside farm offering peaceful living just minutes from Chesapeake’s city conveniences. This charming country home features a wraparound porch, wood floors, woodstove, and a classic claw-foot tub. Home features primary on first floor and 2nd bedroom first floor, and 2 additional BR 2nd floor with small bath. The land offers 4 fenced pastures, with additional paddocks, a 12-acre hay field, bridle path, hay barn, HUGE pole barn, LG chicken coop, LG dog kennel — great for those who love farm life. Timber was replanted with Loblolly pines in 1999, and the property participates in the Land Program with income from hay production &a

$876,000

4 beds2.5 baths2,680 sq ft

1900 Pocaty Rd, Chesapeake, VA 23322

Bridle path • Wood floors • Fenced pastures

CONTINGENT

ABOUT THIS HOME
Pending Listing in Southern Chesapeake, VA:
Private, end-of-cul-de-sac 46.43-acre retreat in the sought-after Grassfield HS district, mix of timber & open fields with room for horses, ATVs, hunting & more. Surrounding trails, deer & wild turkey make this a true sportsman’s paradise, yet close to shopping. Built in 2021, the bright ranch offers an open Kitchen/Living/Dining plan, large bedrooms, generous closets, big utility/mud room, and a primary suite with walk-in closet plus en-suite with jetted tub & separate shower. Stylish white cabinetry, oversized island & Energy Star appliances anchor the kitchen. Evenings made for stargazing by the fire pit; wide skies for sunsets. Plenty of space for pas

$875,000

4 beds2.5 baths2,280 sq ft

2532 Wild Horse Rdg, Chesapeake, VA 23322

Large bedrooms • Generous closets • Big utility mud room

Property at 2913 Lake Drummond Cswy, Chesapeake, VA 23322, 4 beds, 2.5 baths

$750,000

4 beds2.5 baths3,089 sq ft

2913 Lake Drummond Cswy, Chesapeake, VA 23322

Property at 4500 Backwoods Rd, Chesapeake, VA 23322, 4 beds, 3.5 baths

$840,000

4 beds3.5 baths3,228 sq ft

4500 Backwoods Rd, Chesapeake, VA 23322

Property at 1533 Cedarville Ct, Chesapeake, VA 23322, 4 beds, 3.5 baths

$1,278,786

4 beds3.5 baths3,936 sq ft

1533 Cedarville Ct, Chesapeake, VA 23322

Property at 3B Taft Rd, Chesapeake, VA 23322, 4 beds, 3.5 baths

$985,769

4 beds3.5 baths3,423 sq ft

3B Taft Rd, Chesapeake, VA 23322

Property at 1498 Cedarville Ct, Chesapeake, VA 23322, 4 beds, 2.5 baths

$930,120

4 beds2.5 baths3,668 sq ft

1498 Cedarville Ct, Chesapeake, VA 23322

Property at 2209 Centerville Tpke, Chesapeake, VA 23322

$230,000

— beds— baths— sq ft

2209 Centerville Tpke, Chesapeake, VA 23322

Property at 168 AC St Brides Rd W, Chesapeake, VA 23322

$2,000,000

— beds— baths— sq ft

168 AC St Brides Rd W, Chesapeake, VA 23322

Property at Lot 14 Taft Rd, Chesapeake, VA 23322

$600,000

— beds— baths— sq ft

Lot 14 Taft Rd, Chesapeake, VA 23322

Property at 109 Lilypad Ct, Chesapeake, VA 23322, 5 beds, 3.5 baths

$784,555

5 beds3.5 baths3,226 sq ft

109 Lilypad Ct, Chesapeake, VA 23322

Property at 105 Lilypad Ct, Chesapeake, VA 23322, 5 beds, 4 baths

$742,165

5 beds4 baths3,165 sq ft

105 Lilypad Ct, Chesapeake, VA 23322

Property at 404 Stoney Mist Way, Chesapeake, VA 23322, 4 beds, 3 baths

$669,705

4 beds3 baths2,807 sq ft

404 Stoney Mist Way, Chesapeake, VA 23322

Property at 1254 Solitude Trl, Chesapeake, VA 23322, 4 beds, 4 baths

$902,395

4 beds4 baths3,674 sq ft

1254 Solitude Trl, Chesapeake, VA 23322

Property at 2816 Benefit Rd, Chesapeake, VA 23322, 3 beds, 2.5 baths

$415,000

3 beds2.5 baths1,700 sq ft

2816 Benefit Rd, Chesapeake, VA 23322

Property at 149 E Saint Brides Rd, Chesapeake, VA 23322, 5 beds, 3.5 baths

$849,900

5 beds3.5 baths3,118 sq ft

149 E Saint Brides Rd, Chesapeake, VA 23322

Property at 2207 Carolina Rd, Chesapeake, VA 23322, 3 beds, 3 baths

$619,900

3 beds3 baths2,146 sq ft

2207 Carolina Rd, Chesapeake, VA 23322

Property at 1116 Murray Dr, Chesapeake, VA 23322, 4 beds, 3 baths

$710,000

4 beds3 baths2,400 sq ft

1116 Murray Dr, Chesapeake, VA 23322

Property at 801 Benefit Rd, Chesapeake, VA 23322, 3 beds, 2 baths

$650,000

3 beds2 baths2,190 sq ft

801 Benefit Rd, Chesapeake, VA 23322

Property at 928 Shillelagh Rd, Chesapeake, VA 23323, 3 beds, 1 bath

$250,000

3 beds1 bath1,142 sq ft

928 Shillelagh Rd, Chesapeake, VA 23323

Property at 600 Mile Creek Ln, Chesapeake, VA 23322, 5 beds, 3.5 baths

$689,900

5 beds3.5 baths3,100 sq ft

600 Mile Creek Ln, Chesapeake, VA 23322

Property at 2200 Carolina Rd, Chesapeake, VA 23322, 4 beds, 2 baths

$550,000

4 beds2 baths1,575 sq ft

2200 Carolina Rd, Chesapeake, VA 23322

Property at 3252 S Battlefield Blvd, Chesapeake, VA 23322, 4 beds, 2 baths

$450,000

4 beds2 baths1,920 sq ft

3252 S Battlefield Blvd, Chesapeake, VA 23322

Property at 1628 Ballahack Rd, Chesapeake, VA 23322, 3 beds, 1 bath

$273,500

3 beds1 bath955 sq ft

1628 Ballahack Rd, Chesapeake, VA 23322

Property at 2428 Number Ten Ln, Chesapeake, VA 23323, 4 beds, 2.5 baths

$797,000

4 beds2.5 baths2,923 sq ft

2428 Number Ten Ln, Chesapeake, VA 23323

Property at 420 Stoney Mist Way, Chesapeake, VA 23322, 6 beds, 3.5 baths

$781,700

6 beds3.5 baths3,480 sq ft

420 Stoney Mist Way, Chesapeake, VA 23322

Property at 3144 Eason Rd, Chesapeake, VA 23322, 4 beds, 5 baths

$879,000

4 beds5 baths5,757 sq ft

3144 Eason Rd, Chesapeake, VA 23322

Property at 929 Saint Brides Rd W, Chesapeake, VA 23322, 3 beds, 2 baths

$424,000

3 beds2 baths1,538 sq ft

929 Saint Brides Rd W, Chesapeake, VA 23322

Property at 2652 Benefit Rd, Chesapeake, VA 23322, 8 beds, 5.5 baths

$1,595,000

8 beds5.5 baths6,400 sq ft

2652 Benefit Rd, Chesapeake, VA 23322

Property at 2352 Shillelagh Rd, Chesapeake, VA 23323, 5 beds, 4.5 baths

$868,188

5 beds4.5 baths3,668 sq ft

2352 Shillelagh Rd, Chesapeake, VA 23323

Property at 1524 Cedarville Ct, Chesapeake, VA 23322, 4 beds, 3.5 baths

$952,187

4 beds3.5 baths3,490 sq ft

1524 Cedarville Ct, Chesapeake, VA 23322

Property at 3 AC Seven Eleven Rd, Chesapeake, VA 23322, 4 beds, 2.5 baths

$699,000

4 beds2.5 baths2,376 sq ft

3 AC Seven Eleven Rd, Chesapeake, VA 23322

Property at 4792 Ballahack Rd, Chesapeake, VA 23322, 6 beds, 5.5 baths

$1,219,768

6 beds5.5 baths4,010 sq ft

4792 Ballahack Rd, Chesapeake, VA 23322

Property at 1560 Sanderson Rd, Chesapeake, VA 23322, 4 beds, 3.5 baths

$995,260

4 beds3.5 baths3,581 sq ft

1560 Sanderson Rd, Chesapeake, VA 23322

Property at 2344 Shillelagh Rd, Chesapeake, VA 23323, 4 beds, 3.5 baths

$695,000

4 beds3.5 baths3,042 sq ft

2344 Shillelagh Rd, Chesapeake, VA 23323

Property at 4908-A Ballahack Rd, Chesapeake, VA 23322

$274,900

— beds— baths— sq ft

4908-A Ballahack Rd, Chesapeake, VA 23322

Property at 3A Taft Rd, Chesapeake, VA 23322, 4 beds, 3.5 baths

$938,197

4 beds3.5 baths3,484 sq ft

3A Taft Rd, Chesapeake, VA 23322

Property at 1490 Cedarville Ct, Chesapeake, VA 23322, 4 beds, 3.5 baths

$838,152

4 beds3.5 baths3,001 sq ft

1490 Cedarville Ct, Chesapeake, VA 23322

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Pending Listings in Southern Chesapeake

There are currently 45 pending listings for sale in Southern Chesapeake at a median listing price of $782K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Southern Chesapeake stay on the market for 88 days and receive 3 offers. Popular neighborhoods include Greenbrier, Deep Creek, Great Bridge, Kempsville, and Pungo-Blackwater. This map is refreshed with the newest listings in Southern Chesapeake every 15 minutes.

In the past month, 11 homes have been sold in Southern Chesapeake. In addition to houses in Southern Chesapeake, there were also 0 condos, 0 townhouses, and 2 multi-family units for sale in Southern Chesapeake last month. Find your dream home in Southern Chesapeake using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Southern Chesapeake are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Southern Chesapeake. If you're looking to sell your home in the Southern Chesapeake area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Southern Chesapeake with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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