3743 Chesapeake Ave, Hampton, VA 23661
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Property image
OFF MARKET

3743 Chesapeake Ave
Hampton, VA 23661

Greater Wythe
  • 4 Beds
  • 4.5 Baths
  • 5,712 sqft (on 3.38 acres)

$1,695,100

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $9,766/mo*
Refinance Your Home

$1,695,100

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $9,766/mo*
Refinance Your Home
4 Beds
4.5 Baths
5,712 sqft
(on 3.38 acres)

Local Information

  • Map ViewExplore the area around 3743 Chesapeake Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Enjoy all that Coastal Virginia has to offer with this one of a kind property in Olde Wythe! Beautifully renovated home is at the end of a private drive & sits on 3.38 acres with phenomenal views of the Chesapeake Bay! 4 Bedrooms/4.5 Bathrooms, open concept 1st floor with large living room, dining room, kitchen & custom bar. Gourmet kitchen has large island, AGA stove & stainless-steel appliances. Large mudroom & laundry room with gift wrapping station. 1st floor primary suite with fireplace & sitting area. Primary bath has his/her sinks with onyx counters, jetted tub, custom tile shower & heated tile flooring. Upstairs, two secondary bedrooms with ensuite baths. Theater room has custom "snack bar" with fridge. Outside is a screened-in back porch, custom brick patio & outdoor fire pit, oversized garage/workshop, storage shed, updated guest cottage & more! Location offers convenient access to I-64, Downtown Hampton & more!
3743 Chesapeake Ave, Hampton, VA 23661 is a 4 bedroom, 5 bathroom, 5,712 sqft single-family home in Greater Wythe, built in 1951. It last sold for $468,300 on Jul 15, 2002. It is currently off market. The Trulia Estimate is $1,695,100, with a rent estimate of $4,831/month.

Home Highlights

Parking
Garage
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 3743 Chesapeake Ave

Interior Features

Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Hardwood, Linoleum Vinyl
Interior Details
Number of Rooms: 10Types of Rooms: Walk In Closet
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Asphalt, OtherExterior: Vinyl, BrickFoundation Type: Crawl RaisedPatio
Parking & Garage
GarageParking Spaces: 2Parking: Garage Detached

Property Information

Year Built
Year Built: 1951
Property Type / Style
Property Type: Single Family HomeArchitecture: conventional

Community

Units in Building: 2

Lot Information

Lot Area: 3.38 acres

Price History for 3743 Chesapeake Ave

DatePriceEventSource
06/21/2023ListingRemovedLong & Foster Broker Feed
05/18/2023$1,799,500PendingLong & Foster Broker Feed #10475927
05/18/2023$1,799,500ContingentREIN Inc. #10475927
04/20/2023$1,799,500PendingToActiveREIN Inc. #10475927
03/30/2023$1,799,500PendingLong & Foster Broker Feed #10475927
03/30/2023$1,799,500ContingentREIN Inc. #10475927
02/24/2023$1,799,500Listed For SaleREIN Inc. #10475927
07/15/2002$468,300Sold
N/A

Market trends in Greater Wythe

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$237K
$9.67KMoM
Sale-to-List Price
—
Price per sq ft
—
Available listings
78
11MoM
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Property Tax and Assessment

Year2025
Tax$16,058
Assessment$1,399,300
Home facts updated by county records

Comparable Sales for 3743 Chesapeake Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3748 Chesapeake Ave, Hampton, VA
0.06
Single-Family Home
$586,700
07/11/25
5
3.5
3,547
3749 Chesapeake Ave, Hampton, VA
0.04
Single-Family Home
$499,000
11/05/25
4
3
2,609
4002 Chesapeake Ave, Hampton, VA
0.33
Single-Family Home
$782,800
08/18/25
5
3.5
3,000
4017 Buchanan Dr, Hampton, VA
0.51
Single-Family Home
$462,500
12/15/25
5
3.5
3,423
200 Congress Ave, Hampton, VA
0.87
Single-Family Home
$1,350,000
08/18/25
4
4
4,643
108 Lasalle Ave, Hampton, VA
0.16
Single-Family Home
$313,500
09/26/25
5
3
1,770
4012 Chesapeake Ave, Hampton, VA
0.41
Single-Family Home
$1,100,000
07/08/26
6
5.5
5,203
3403 Chesapeake Ave, Hampton, VA
0.40
Single-Family Home
$605,000
09/29/25
3
3
2,758
3602 Spottswood Pl, Hampton, VA
0.22
Single-Family Home
$340,000
07/10/25
3
2.5
1,774
4012 Buchanan Dr, Hampton, VA
0.47
Single-Family Home
$350,000
02/06/26
4
3
2,672

Nearby homes

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Assigned Schools

These are the assigned schools for 3743 Chesapeake Ave.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Greater Wythe
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Greater Wythe

At least 117 Trulia users voted on each feature.

  • 91 % Say car is needed

  • 90 % Say parking is easy

  • 86 % Say yards are well-kept

  • 81 % Say it's dog friendly

  • 71 % Say there's holiday spirit

  • 70 % Say kids play outside

  • 70 % Say there are sidewalks

  • 63 % Say streets are well-lit

  • 61 % Say it's quiet

  • 54 % Say neighbors are friendly

  • 51 % Say it's walkable to grocery stores

  • 51 % Say they plan to stay for at least 5 years

  • 50 % Say people would walk alone at night

  • 41 % Say there's wildlife

  • 31 % Say there are community events

  • 22 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Deborahaaron
    "Park like environment. Very nice for pets and children. Waterfront is exceptional and friends and family enjoy when they visit."
    0
    Flag
  • Em Leeks
    "Safety of the area, the abundant enrichment products available for our kids, and a place of peace. Great school zone and convenience to available retail stores to provide for the family "
    0
    Flag
  • Dblunt26
    "Virginia is home for lovers. A great place to raise a family and enjoy the fruits that life has to offer. Many places to shop, dine, and enjoy the atmosphere. "
    0
    Flag
  • Trulia User
    "I’ve lived here 12 years and raised my kid here. It’s a unique neighborhood where each house has its own flair, no HOA, and folks wave and say hello as they bike or walk by. Kids hang out and play. There’s a sense of community here. LOVE living in Wythe!"
    9
    Flag
  • Trulia User
    "it's pretty much a family-oriented neighborhood is easy access to the interstate 64. it's a great area if you're interested in going to the local beaches museums parks Waterfront area it's a great area for fishing"
    0
    Flag
  • Trulia User
    "This is a family friendly environment. People are pleasant and for the most part everyone keeps to themselves. Great place to live"
    0
    Flag
  • Trulia User
    "Plenty space to walk your dog abs a nice neighborhood to have a walk great scenery friendly people you will see why walking "
    1
    Flag
  • Trulia User
    "pleasant, great neighborhood, well lit at night. My area is like big family. Kids play in yards and ride bikes in the summer all the time. Kids walk to school bus stops alone. very safe place for kids. Grocery store is close. 711 right around the corner. Advance Auto up the street."
    0
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  • Cameron W.
    "The neighborhood is definitely up and coming. New houses are being built and local stores are revamping their curbside appeal. It’s close to the James River and moderately quiet area. "
    12
    Flag
  • Thaddeus L.
    "People are always walking their dogs around the neighborhoods. Dogs are usual leashed, and friendly. Even bigger “aggressive breed” dogs. Lots of responsible owners"
    4
    Flag
  • Mark E.
    "This is a diverse affordable waterfront community. It has a park like setting throughout, with beautiful homes, unobstructed views of the Chesapeake, convenient parks and the people are all great! "
    16
    Flag
  • Susan T.
    "Great walkable neighborhood with residents of all ages and incomes. Near the water yet close to downtown amenities "
    5
    Flag
  • Kayla S.
    "great place to live...it's quite...comfortable...by the water...really great place good place for kids to grow up...and older people"
    18
    Flag
  • Janice J.
    "We do not have any community events that make this place special. There was a pool event once for some kid and a race of some sort."
    8
    Flag
  • Janice J.
    "I drive to work. There are different routes that I can take to get to work. The traffic isn’t too bad."
    2
    Flag
  • Stacey D. J.
    "good neighborhood to walk dogs and socialize with neighbors.............................................."
    0
    Flag
  • Jacob M.
    "No community events really. People leave each other alone for the most part. Kids play in the street and I would highly recommend the area. "
    0
    Flag
  • Samantha
    "We are moving in next week and are very excited about our future in this area. We love the neighborhood and the potential! "
    0
    Flag
  • Nieko A.
    "it's a beautiful and unique area with a secluded feel ; although, close to the city center. I enjoy the people and variety of shopping and nature"
    11
    Flag
  • Dalyce P.
    "Where we are close to the water there are a lot of pot holes!!! Very quiet and peaceful. Police heavily enforced "
    0
    Flag
  • Ryan
    "my neighborhood has a great vibe and all the neigbors are inviting and friendly. parking is never an issue and i always feel comfortable here."
    0
    Flag
  • Jesse H.
    "I have lived here a year and a half now, there is a lot to do in the area. minutes from the ocean. great area. "
    8
    Flag
  • James B.
    "they would like that they can walk there dog and pick up the things there pet leave behind. They can walk there pet to a park that is located less than a mile away "
    1
    Flag
  • Cynn1963
    "People walk their dogs around the neighborhood all the time. I’ve never seen any dogs running loose. The dogs that live next-door to me are very friendly."
    0
    Flag
  • Susan T.
    " A great deal of dog walking and socializing takes place in our community on a daily basis. The variety of streets and open spaces make it interesting for the dogs."
    0
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  • Dalyce P.
    "its okay the busses aren't as frequent and the scheduling and routes conflict. but if you have a car or bike its awesome."
    1
    Flag
  • Susan T.
    "The hIstoric character of the homes, the proximity to the water and the trees. Lots of young families are moving in."
    0
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  • Denise M. M.
    "Great neighbors, people in the area they watch out for eachother. Neighborhood is quiet and the scenic views are great for walks with your loved ones dogs included and bike rides"
    9
    Flag
  • Lambertgrp
    "Live 120 feet and I have a a panoramic view of Chesapeake bay. Stately homes built doing the roaring twenties. Natural gas and a popular that believes York town is the place to raise a family. This misperception keeps our city assessments low and our property tax reasonable."
    5
    Flag

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Apartments for Rent

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Homes for sale near 3743 Chesapeake Ave

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Off Market Homes Near 3743 Chesapeake Ave

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