Vintage homes for sale & real estate in Isle of Wight County, VA

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ABOUT THIS HOME
Vintage Home for sale in Isle of Wight County, VA:
Own a piece of Smithfield history. Set on 0.93 acres along the Pagan River, this stunning 1902 Late-Victorian waterfront estate offers 7,096 sq ft of timeless elegance, plus a full unfinished basement. The home features 5 bedrooms, 3 full and 2 half baths, 11-ft barrel ceilings, stained-glass windows, tiger oak hardwood floors, breathtaking trim work, 9 custom fireplaces, and 13 chandeliers. Highlights include a grand front parlor, tall windows, working pocket doors, a private library, and a third-floor ballroom can be used for a media or game room. The fully renovated eat-in kitchen showcases a marble slab island, marble countertops and backsplash, Wolf 6-burner range with double ovens, Su

$1,895,000

5 beds4 baths7,096 sq ft

345 S Church St, Smithfield, VA 23430

Marble slab island • Third-floor ballroom • Grand front parlor

ABOUT THIS HOME
Vintage Home for sale in Isle of Wight County, VA:
Historic charm meets opportunity at 328 Main Street! This updated 3BR/1.5BA, 1,816 sqft home is zoned residential & commercial and has an approved special variance as a short-term rental from the town of Smithfield. This beauty is fully furnished for a turnkey investment at $550K! Features include first-floor primary suite, electric fireplace, walk-in closet, patio, partial fenced yard, and all appliances included. Whether you want to live here, run a business, or earn income right away, situated in historic downtown Smithfield, this location delivers.

$550,000

3 beds2.5 baths1,816 sq ft

328 Main St, Smithfield, VA 23430

Zoned residential • Short-term rental • Electric fireplace

ABOUT THIS HOME
Vintage Home for sale in Isle of Wight County, VA:
Welcome to a rare and breathtaking 96-acre farm in the heart of Smithfield — the ultimate outdoorsman’s paradise. This expansive property features a stunning 7-acre pond, for fishing, kayaking, or simply enjoying peaceful waterfront views. Whether you’re into hunting, horseback riding, ATV adventures, or just soaking in the quiet of wide-open spaces, this land offers endless possibilities. With a mix of open fields, wooded trails, and abundant wildlife, create your dream homestead, recreational retreat, or even a private event venue. A 2-bedroom, 1-bath dwelling is already on-site — perfect as a hunting cabin, weekend getaway, or guest house while you build your drea

$825,000

2 beds1 bath1,056 sq ft

9742 Mill Swamp Rd, Smithfield, VA 23430

96 acre farm • Guest house • Wooded trails

ABOUT THIS HOME
Vintage Home for sale in Isle of Wight County, VA:
Step into a piece of Smithfield’s history—an extraordinary 1702-built estate - once owned by the town’s founder. This 5,332 sqft residence perfectly marries historic character with modern comfort. Grand double doors open to a sweeping foyer and staircase, formal living and dining rooms, and a primary suite with a private balcony overlooking enchanting gardens leading to Little Creek and Windsor Castle Park. Enjoy two fully equipped kitchens, multiple fireplaces, original wood floors and a finished basement with a private entrance. A newer 75-year roof, whole-home generator, and lush outdoor spaces with fountain and fire-pit complete this timeless masterpiece.

$1,000,000

4 beds3.5 baths5,332 sq ft

338 S Church St, Smithfield, VA 23430

Multiple fireplaces • Private balcony • Original wood floors

ABOUT THIS HOME
Vintage Home for sale in Isle of Wight County, VA:
Come see this 5 bedroom, 3.5 bath home in Windsor with detached garage and in-law suite.

$315,000

5 beds3.5 baths2,729 sq ft

29 N Court St, Windsor, VA 23487

0.4 acre lot • Garage • Built 1939

Property at 12265 Smiths Neck Rd, Carrollton, VA 23314, 3 beds, 1 bath

$195,000

3 beds1 bath1,092 sq ft

12265 Smiths Neck Rd, Carrollton, VA 23314

Property at 351 S Church St, Smithfield, VA 23430, 5 beds, 3.5 baths

$1,200,000

5 beds3.5 baths4,422 sq ft

351 S Church St, Smithfield, VA 23430

Property at 3639 Carrsville Hwy, Franklin, VA 23851, 2 beds, 1 bath

$274,900

2 beds1 bath1,196 sq ft

3639 Carrsville Hwy, Franklin, VA 23851

Property at 17314 Jolly Cir, Windsor, VA 23487, 4 beds, 3 baths

$545,000

4 beds3 baths1,749 sq ft

17314 Jolly Cir, Windsor, VA 23487

Property at 405 S Church St, Smithfield, VA 23430, 2 beds, 1.5 baths

$402,000

2 beds1.5 baths982 sq ft

405 S Church St, Smithfield, VA 23430

Property at 403 S Church St, Smithfield, VA 23430, 3 beds, 1.5 baths

$481,000

3 beds1.5 baths982 sq ft

403 S Church St, Smithfield, VA 23430

Property at .71 Ac E Windsor Blvd, Windsor, VA 23487

$175,000

— beds— baths— sq ft

.71 Ac E Windsor Blvd, Windsor, VA 23487

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NEW 6 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Isle of Wight County, VA:
AMAZING OPPORTUNITY. A little love and INSTANT equity on this one!! 4 bedrooms, 2 baths, updated kitchen. Needs a good cleaning and some fresh paint and you'll be good to go! Selling as-is for a quick sale, subject to short sale approval, but definitely worth it! Schedule your showing today!

$195,000

4 beds2 baths2,002 sq ft

3328 Candlewood Dr, Hampton, VA 23666

Built 1958

NEW 12 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Isle of Wight County, VA:
This classic single story home has the kind of original charm you just don’t find anymore, and it’s been well cared for along the way. Featuring a large living room with a wood burning fireplace plus a separate family room that gives everyone space to spread out. With four bedrooms and an additional office, there’s flexibility here whether you need room to work from home, host guests, or grow into the space over time. Large corner lot with a detached garage, a small sunroom that catches the light just right, and a deck ready for morning coffee or weekend grilling. The home is in great shape and ready for someone to bring their own style and updates to make it truly theirs.

$250,000

4 beds2 baths1,835 sq ft

34 Meadow Creek Dr, Newport News, VA 23608

Small sunroom • Large corner lot • Separate family room

NEW 27 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Isle of Wight County, VA:
INVESTOR SPECIAL, DUPLEX NEAR SUFFOLK HISTORIC DISTRICT!!

$280,000

4 beds2 baths2,184 sq ft

308 Central Ave, Suffolk, VA 23434

4,356 sq ft lot • Built 1754

NEW 28 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Isle of Wight County, VA:
Welcome to this charming updated ranch offering an open, inviting layout with new paint, new waterproof vinyl flooring thought out and new fixtures. The spacious kitchen, equipped with new cabinets, granite countertops & stainless steel appliances are great for both everyday living & entertaining. Natural light streams through the new windows, while outside, a fully fenced-in and huge yard and detached garage creates a perfect space for outdoor activities. Additional features includes a new roof and new vinyl siding! Enjoy living close to the bay/ocean, fishing piers, public boat ramps, 5 beautiful parks, many historical sites, military bases, interstates, restaurants, entertain

$200,000

2 beds1 bath818 sq ft

618 33rd St, Newport News, VA 23607

Updated ranch • Spacious kitchen • Natural light

NEW 28 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Isle of Wight County, VA:
Purchase home with Cash or Hard Money Loan ONLY. AS-IS-WHERE-IS. Seller to make no repairs. Verifiable proof of funds required for showing. This home is a historical Seats Kit Home. Repairs and cosmetic updates will make this home perfect for the right individual or family.

$174,900

4 beds2.5 baths1,958 sq ft

506 Walnut St, Franklin, VA 23851

7,492 sq ft lot • Garage • Built 1947

NEW 31 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Isle of Wight County, VA:
Come see this beautifully renovated home. All new flooring, windows, doors, appliances and fixtures. The kitchen features stainless-steel appliances and sleek white cabinets. Primary bedroom with bathroom and custom tile. New roof, siding, HVAC and water heater. Schedule your showing today!

$230,000

3 beds2 baths892 sq ft

121 S 10th St, Suffolk, VA 23434

Renovated home • Custom tile • White cabinets

Property at 6613 Holland Rd, Suffolk, VA 23437, 4 beds, 3.5 baths

$369,900

4 beds3.5 baths2,800 sq ft

6613 Holland Rd, Suffolk, VA 23437

Property at 117 Whites Ln, Seaford, VA 23696, 2 beds, 1 bath

$295,000

2 beds1 bath997 sq ft

117 Whites Ln, Seaford, VA 23696

Property at 344 Colonial Trl, Surry, VA 23883, 3 beds, 2 baths

$349,900

3 beds2 baths1,978 sq ft

344 Colonial Trl, Surry, VA 23883

Property at 300 Fuller St, Suffolk, VA 23434, 3 beds, 2 baths

$184,999

3 beds2 baths1,015 sq ft

300 Fuller St, Suffolk, VA 23434

Property at 66 Cline Dr, Hampton, VA 23666, 3 beds, 2.5 baths

$365,000

3 beds2.5 baths1,800 sq ft

66 Cline Dr, Hampton, VA 23666

Property at 223 Bank St, Suffolk, VA 23434, 3 beds, 1 bath

$120,300

3 beds1 bath4,028 sq ft

223 Bank St, Suffolk, VA 23434

Property at 879 Alliance Rd, Surry, VA 23883, 3 beds, 1 bath

$255,750

3 beds1 bath1,272 sq ft

879 Alliance Rd, Surry, VA 23883

Property at 316 W Washington St, Suffolk, VA 23434, 6 beds, 4 baths

$440,000

6 beds4 baths4,150 sq ft

316 W Washington St, Suffolk, VA 23434

Property at 311 Jackson St, Suffolk, VA 23434, 4 beds, 2 baths

$240,000

4 beds2 baths1,912 sq ft

311 Jackson St, Suffolk, VA 23434

Property at 301 Jackson St, Suffolk, VA 23434, 4 beds, 2 baths

$225,000

4 beds2 baths1,500 sq ft

301 Jackson St, Suffolk, VA 23434

Property at 303 Jackson St, Suffolk, VA 23434, 4 beds, 2 baths

$225,000

4 beds2 baths1,488 sq ft

303 Jackson St, Suffolk, VA 23434

Property at 124 Wellons St, Suffolk, VA 23434, 5 beds, 2 baths

$300,000

5 beds2 baths2,800 sq ft

124 Wellons St, Suffolk, VA 23434

Property at 129 Chestnut St, Suffolk, VA 23434, 4 beds, 4 baths

$180,000

4 beds4 baths2,728 sq ft

129 Chestnut St, Suffolk, VA 23434

Property at 115 Chestnut St, Suffolk, VA 23434

$190,000

— beds— baths2,000 sq ft

115 Chestnut St, Suffolk, VA 23434

Vintage Homes for Sale in Isle of Wight County

There are currently 12 vintage homes for sale in Isle of Wight County at a median listing price of $465K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Isle of Wight County stay on the market for 79 days and receive 2 offers. This map is refreshed with the newest listings in Isle of Wight County every 15 minutes.

In the past month, 74 homes have been sold in Isle of Wight County. In addition to houses in Isle of Wight County, there were also 33 condos, 18 townhouses, and 1 multi-family unit for sale in Isle of Wight County last month. Find your dream home in Isle of Wight County 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 Isle of Wight County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Isle of Wight County. If you're looking to sell your home in the Isle of Wight County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Isle of Wight County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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