1029 Sherando Ct, Chesapeake, VA 23320
Porch
Master Shower
OFF MARKET

$837,900

Trulia Estimate
  • 6 Beds
  • 4.5 Baths
  • 4,200 sqft (on 0.35 acres)

1029 Sherando Ct, Chesapeake, VA 23320

Greenbrier East
Est. Refi. Payment $5,128/mo*
Refinance Your Home
Currently Off Market - Sold Jul 17, 2017 for $500,000

Home Value

Trulia Estimate
$838K
Since last month
Increased$5K (+0.6%)
Since last year
Increased$18K (+2.1%)
Since last sale
Increased$338K (+67.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +61% in the last 10 years
MonthEstimated value
2026
September 2026$838K
August 2026$834K
July 2026$834K
June 2026$847K
May 2026$843K
April 2026$848K
March 2026$838K
February 2026$821K
January 2026$811K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1026 Woodwind Way, Chesapeake, VA
0.11
Single-Family Home
$585,000
05/13/26
4
2.5
2,882
1017 Winchester Way, Chesapeake, VA
0.12
Single-Family Home
$549,900
05/12/26
4
2.5
2,378
1129 Cumberland Ct, Chesapeake, VA
0.15
Single-Family Home
$723,000
08/11/26
4
3
3,458
1045 Winchester Way, Chesapeake, VA
0.07
Single-Family Home
$270,000
07/20/26
4
2.5
2,600
1021 Woodwind Way, Chesapeake, VA
0.16
Single-Family Home
$535,000
08/03/26
4
3
2,469
1439 Kemp Bridge Dr, Chesapeake, VA
0.46
Single-Family Home
$635,000
08/13/26
5
3.5
3,500
1417 Kemp Bridge Ln, Chesapeake, VA
0.58
Single-Family Home
$755,000
08/04/26
5
3.5
3,952
1304 Kemp Bridge Dr, Chesapeake, VA
0.53
Single-Family Home
$675,900
10/07/25
5
4.5
3,314
1132 Cumberland Ct, Chesapeake, VA
0.10
Single-Family Home
$739,000
06/10/26
6
4
3,849
1302 Sasparilla Ct, Chesapeake, VA
0.52
Single-Family Home
$569,900
07/07/26
4
2.5
2,494

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
1017 Winchester Way, Chesapeake, VA 23320
0.12
$549,900
4
2.5
2,378
Recently Sold
1026 Woodwind Way, Chesapeake, VA 23320
0.11
$585,000
4
2.5
2,882
Recently Sold
1132 Cumberland Ct, Chesapeake, VA 23320
0.10
$739,000
6
4
3,849
Recently Sold
1129 Cumberland Ct, Chesapeake, VA 23320
0.15
$723,000
4
3
3,458
Recently Sold
901 Cooper Ln, Chesapeake, VA 23320
0.25
$649,900
4
2.5
2,432
Off Market
905 Cooper Ln, Chesapeake, VA 23320
0.25
$654,600
4
2.5
2,432
Off Market
936 Biltmore Way #37, Chesapeake, VA 23320
0.26
$490,000
3
3
2,112
Recently Sold
922 Biltmore Way, Chesapeake, VA 23320
0.28
$534,100
3
3
2,235
Off Market
1404 Shenandoah Parkway, Chesapeake, VA 23320
0.34
$560,900
4
2.5
2,540
Off Market
937 Brenner Rd, Chesapeake, VA 23320
0.31
$610,800
4
2.5
2,432
Off Market
935 Brenner Rd, Chesapeake, VA 23320
0.31
$542,100
4
2.5
2,202
Off Market
809 Monroe Court, Chesapeake, VA 23320
0.31
$425,600
3
2.5
2,225
Off Market

Local Information

  • Map ViewExplore the area around 1029 Sherando Ct.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1990
0.35 acre lot
4,200 sqft
$200/sqft
Garage

About this House


Welcome to your luxurious family haven in the prestigious Hampton Roads Community, an all-brick masterpiece meticulously crafted by a renowned construction company.

Key Features:

Open Living: The seamless open living plan connects the living, dining, and kitchen spaces, perfect for creating cherished family memories.
Grand All-Brick Home: This house boasts impeccable all-brick architecture, built to the highest standards, ensuring lasting quality and style.
Detailed Floor Plan: Grand entryways and meticulous design promote effortless flow between rooms for everyday living and entertaining.
In-Law Suite: Enjoy an in-law suite, providing privacy and independence for extended family members while maintaining the cohesion of your home.
In-Ground Pool: Your private outdoor oasis features an inviting L-shaped in-ground pool, ideal for lap swimming or entertaining.
Outdoor Entertainment: A generously-sized yard with a Lifetime playground and outdoor seating areas invites relaxation and stargazing on warm evenings.
Gourmet Kitchen: The kitchen is a culinary masterpiece with a custom-built refrigerator and ample storage for functionality and organization.
Double Garages: Two full garages are perfect for vehicle storage or potential game areas. A convenient pool bathroom adds to the convenience.
Convenient Location: Situated in a secure, mature neighborhood with single-entry access, your family's safety is paramount. Proximity to schools, shopping, and amenities make life convenient, with quick access to 168 and I-64 expressways.
This residence embodies luxury living, family bonding, and entertainment, offering a unique opportunity in the Hampton Roads Community.

House History & Upgrades:

This impeccably maintained property offers a glimpse into its history and upgrades:

Extensive Upgrades: Previous owners expanded living spaces and added a permitted in-law suite with a half bathroom in 2007.
Modernization: A new dishwasher was installed in 2020, and a minor repair was done on the built-in refrigerator in June 2023.
Irrigation & Water System: An irrigation system was installed in July 1999, while the septic water pump serves the yard. The house water supply is from the city.
Pool Perfection: The pool is meticulously maintained with Mineral Pure ionized water and a 2017 Panama Royal Prism pool liner.
HVAC & Water Heater: A dual Goodman HVAC system from 2006 ensures year-round comfort. The water heater was upgraded in December 2018.
Energy Efficiency: The house includes an electric Sentry Energy Management System for electricity savings.
Community: Nestled in the Kemps Woods Planned Unit Development (PUD), the property benefits from a Civic League for community engagement.
Roof & Crawl Space: The roof boasts architectural shingles with a 30-40 year lifespan. The crawl space is meticulously enclosed and protected.
Landscaping Excellence: Gomez Landscaping has maintained the grounds for six years, ensuring the exterior matches the interior's impeccable presentation.
This property showcases thoughtful upgrades and meticulous maintenance, offering a turnkey experience for its fortunate new owners.

1029 Sherando Ct, Chesapeake, VA 23320 is a 6 bedroom, 4 bathroom, 4,200 sqft single-family home in Greenbrier East, built in 1990. It last sold for $500,000 on Jul 17, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $837,900, with a rent estimate of $4,066/month.

Home Details for 1029 Sherando Ct

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Linoleum Vinyl
Interior Details
AtticIn-law unitNumber of Rooms: 11Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Office, WorkshopCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalRefrigerator
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: BrickFoundation Type: OtherLawnPorch
Pool
Pool
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached, Garage Detached

Property Information

Year Built
Year Built: 1990Year Updated: 2007
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.35 acres

Price and Tax history

DateEventPrice
Sep 5, 2023
Source: N/A
ListingRemoved
Aug 30, 2023
Source: N/A
Listed For Sale
$750,000
Jul 17, 2017
Source: N/A
Sold
$500,000
Jun 15, 2017
Source: Agent Provided
Pending
$500,000
May 3, 2017
Source: Agent Provided
Listed For Sale
$500,000

Market trends in Greenbrier East

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$407K
$3.83KMoM
Sale-to-List Price
100.1%
Price per sq ft
$227
$4MoM
Available listings
120
6MoM

Around this home

Neighborhood Overview

Greenbrier East
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Greenbrier East

At least 321 Trulia users voted on each feature.

  • 94 % Say it's dog friendly

  • 88 % Say car is needed

  • 88 % Say parking is easy

  • 78 % Say there are sidewalks

  • 74 % Say it's quiet

  • 73 % Say streets are well-lit

  • 73 % Say there's holiday spirit

  • 72 % Say people would walk alone at night

  • 70 % Say yards are well-kept

  • 68 % Say kids play outside

  • 56 % Say they plan to stay for at least 5 years

  • 53 % Say it's walkable to restaurants

  • 52 % Say neighbors are friendly

  • 49 % Say it's walkable to grocery stores

  • 40 % Say there's wildlife

  • 28 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Sophia.anne.molina
    "Some days there is bad traffic and others it’s smooth. I find that compared to other cities it’s decent. I would describe my commute as fair compared to living in Portsmouth or Norfolk or Virginia Beacb. My commute is anywhere from 5 minutes to 35 minutes from my place of residence. That’s all I would say. "
    0
    Flag
  • Shirley Belue
    " The is a family oriented community. There are schools and parks to get walks for health. Many neighbors have dogs and cats. There are no sidewalks, just a two lane road. "
    1
    Flag
  • stampwithsharon
    "Excellent book club! Neighbors are very friendly. Quiet neighbors,nice pool. Walkable to grocery, restaurants and library. "
    0
    Flag
  • M2jfr2k9vs
    "Motor vehicles are the ultimate way to travel, they’re so convenient! I highly recommend getting or having a vehicle!!!"
    1
    Flag
  • 94zw848pdw
    "Not too bad. I get to work within 20 minutes with minimal traffic. Not sure what else to say about it"
    2
    Flag
  • Kclynncarlisle
    "Pizza party’s, barbecues, trick or treating, thanksgiving potlucks, back porch hang outs, pool party’s. "
    0
    Flag
  • Colpotitoli
    "Nice safe clean friendly close to all shopping center urgent care and other hospitals are very close "
    1
    Flag
  • Trulia User
    "There are always dogs being walked and playing in the field by my apartment with their owners. It is a very dog friendly area and the owners are polite and kind and courteous of other dogs as well as people who live around here without dogs. "
    1
    Flag
  • Trulia User
    "Great community, Friendly , quiet , kid friendly. Lived here all of my life and have never had issues or problems. "
    0
    Flag
  • Trulia User
    "I've lived here and love it I would recommend everyone to live here .I'm so ready To live in this area again "
    2
    Flag
  • Trulia User
    "There are no events at our apartment complex or the 2 next to ours. The mall is dieing. I do love the craft fair at the park. I hope next year it is bigger with more information on what our city has to offer. I miss the pow wows the park had. it is a good reminder of the Native American heritage. "
    0
    Flag
  • Trulia User
    "They would definitely not like people not picking up after their dogs They’ll love walking their dog around the neighborhood "
    0
    Flag
  • Rachelrb
    "This neighborhood is the perfect place to raise a family.It’s beautiful, safe, and extremely fun for kids! "
    13
    Flag
  • Ken L.
    "Close to everything. Very friendly people, and nice area. Schools are great. I went to Oscar Smith for a year, and while there teachers truly pushed me."
    5
    Flag
  • Sharlene R.
    "As there many dog owners in the neighbor. A lot of dog lovers within the communities. Must be careful as Bishopstokes is a race trap "
    7
    Flag
  • Littlesugarmom
    "Great area to raise kids, family oriented area. Great parks and trails. Lots to do and close proximity to everything necessary "
    1
    Flag
  • Stephaniestout94
    "Quiet neighborhood. A lot of families. Close to everything. Food entertainment , shopping, dog parks. "
    2
    Flag
  • Katelyn W.
    "There’s plenty of areas to walk your dog. Sidewalks, parks, lots of trees. Most places have fences and yards or are pet friendly apartments. "
    0
    Flag
  • Carrie J.
    "it's nice and quite yet close to anything you could possibly need or want. I have lived here for 2 years and love the area."
    4
    Flag
  • Ashley D.
    "Quiet and safe. Right next to a school and a mall which is hard to find. The cops monitor the neighbor and make sure speeding is kept to a minimum."
    12
    Flag
  • Karena P.
    "It’s a great place to live, especially if you have a young family! Great schools, and great for pets! "
    0
    Flag
  • Ash M.
    "Great neighborhood with great restaurants and shopping within 5 miles radius. Very safe with sidewalks pretty much everywhere."
    3
    Flag
  • Ahagenbucher182
    "I love this area so much. It’s such a great place to raise of family!!! :) Greenbrier East is the best! "
    0
    Flag
  • A.brown2134
    "It’s a great place to raise your family. I would recommend this area to anyone looking for a nice, friendly, quiet atmosphere "
    1
    Flag
  • Rebecca B.
    "Although there are areas to play between our patios and the white sticks indicating the golf course property, children do not play back there. The only time I’ve ever seen children play in the area that is available and allowed is wintertime when snow is on the grounds."
    0
    Flag
  • Brittany B.
    "Been around this neighborhood for a while. Very family friendly. Love the area in general. Great place to raise a family."
    3
    Flag
  • Fw
    "I love it here! Neighborhood is nice and quiet. Streets are always clean, very convenient to shopping, I always feel safe here. "
    0
    Flag
  • Don7likeu
    "This is a great place to live. There are many shops nearby and great schools. I have been here for two years and don't plan on moving to a different area any time soon."
    0
    Flag
  • Lpierce4511
    "I've loved in this neighborhood for 4 years. It's close to shopping and interstates making it easy to travel. I've always felt very safe in this area. I love the lake and walking path!"
    4
    Flag
  • Rebekah MO
    "This is a wonderful neighborhood, everyone is so friendly and close to everything! I would highly recommend this area to anyone! "
    0
    Flag
  • Rosario36@yahoo.com
    "Cooks outs, sharing info, schools, friends, scenery, hospitality, clean, pool, fun, picnics, and parties "
    0
    Flag
  • Fabian O.
    "Great area to live in. Everything you could ever need is within 10 to 15 minutes driving would recommend to anyone"
    0
    Flag
  • Marlena S.
    "Dog owners would love that 4 Paws, PetSmart, Barker and open dog parks are literally down the street"
    0
    Flag
  • Amy B.
    "My neighborhood is 100% dog friendly. People are always out walking their dogs. There is also a dog park around the corner at Chesapeake City Park "
    0
    Flag
  • KC
    "I’ve lived here for six months now, the area is great for going on runs and walks, my neighbors are friendly and the area is clean. There’s a lake nearby and plenty of shopping for anything you need within minutes of your house."
    9
    Flag
  • Gellinabaez
    "Dogs in the Greenbrier area seem to be friendly and well-trained; I never hear loud, constant barking. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 1029 Sherando Ct

  • What is 1029 Sherando Ct estimated to be worth?
    Trulia's estimated value for 1029 Sherando Ct in Chesapeake, VA is $837,900.
  • What is the price history for 1029 Sherando Ct?
    1029 Sherando Ct in Chesapeake, VA last sold for $500,000 in July 2017.
  • Is Chesapeake a buyer's or seller's market?
    Chesapeake is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Chesapeake?
    The median sale price in Chesapeake is $407K. That is up $3.83K from the prior month.
  • Does 1029 Sherando Ct have air conditioning?
    Yes, 1029 Sherando Ct in Chesapeake, VA has air conditioning.
  • Does 1029 Sherando Ct have a pool?
    Yes, 1029 Sherando Ct in Chesapeake, VA has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Outdoor Space

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