1355 Simon Dr, Chesapeake, VA 23320
OFF MARKET

1355 Simon Dr
Chesapeake, VA 23320

Greenbrier East
  • 5 Beds
  • 4 Baths
  • 3,680 sqft (on 0.60 acres)

$961,900

Trulia Estimate
as of Jul 20, 2026
Est. Refi. Payment $5,558/mo*
Refinance Your Home

$961,900

Trulia Estimate
as of Jul 20, 2026
Est. Refi. Payment $5,558/mo*
Refinance Your Home
5 Beds
4 Baths
3,680 sqft
(on 0.60 acres)

Local Information

  • Map ViewExplore the area around 1355 Simon Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Single Family Home for sale by owner in Chesapeake, VA 23320. Beautiful lakefront lot!!-New Construction-Underway 7/1/10. LOADED custom brick home with stone accents. Almost 3700'-5 BR's w/ master down plus bonus office. 3.5 baths. Double trey ceiling in master. Huge side loading garage with 2 OH doors. Loaded with tile,HW, upgraded mouldings,granite tops,SS appliances,etc. 2 story foyer and 11' FR ceilings. Many extra's-pre-wire package,security,sod. Rear covered porch with fan to enjoy evenings overlooking lake. Hurry now while finishes still available to select. A great value even in today's market-very reasonably priced at $582,900. Completion approx 12/10. Please call 652 9079 for more details.
1355 Simon Dr, Chesapeake, VA 23320 is a 5 bedroom, 4 bathroom, 3,680 sqft single-family home in Greenbrier East, built in 2011. It last sold for $540,000 on May 31, 2011. It is currently off market. The Trulia Estimate is $961,900, with a rent estimate of $4,160/month.

Home Highlights

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

Home Details for 1355 Simon Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
AtticNumber of Rooms: 10
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: BrickFoundation Type: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2011
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 0.60 acres

Price History for 1355 Simon Dr

DatePriceEventSource
02/19/2021ListingRemovedN/A
02/05/2012$582,900ListingRemovedN/A
08/04/2011$582,900Listed For SaleN/A
05/31/2011$540,000Sold
N/A
04/22/2011$559,000PriceChange
Agent Provided
02/20/2011$575,000PriceChange
Agent Provided
01/08/2011$582,900PriceChange
Agent Provided
12/04/2010$597,900Listed For SaleAgent Provided
06/24/2010$145,500Sold
N/A
03/19/2010$150,000Sold
N/A
09/22/2008$242,075Sold
N/A

Market trends in Greenbrier East

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$405K
$15KMoM
Sale-to-List Price
100.0%
Price per sq ft
$224
$8MoM
Available listings
103
1MoM
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Property Tax and Assessment

Year2025
Tax$9,400
Assessment$930,700
Home facts updated by county records

Comparable Sales for 1355 Simon Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1356 Simon Dr, Chesapeake, VA
0.05
Single-Family Home
$894,900
09/04/25
4
3.5
3,746
1212 Masters Row, Chesapeake, VA
0.30
Single-Family Home
$550,000
07/23/25
4
3.5
3,252
1207 Masters Row, Chesapeake, VA
0.28
Single-Family Home
$900,000
04/27/26
5
4
3,962
1345 Simon Dr, Chesapeake, VA
0.09
Single-Family Home
$899,900
01/30/26
5
4.5
4,751
1322 Simon Dr, Chesapeake, VA
0.12
Single-Family Home
$904,000
11/21/25
6
4.5
4,023
1301 Niblick Ct, Chesapeake, VA
0.35
Single-Family Home
$855,000
08/28/25
5
3.5
3,641
1305 Turnberry Ct, Chesapeake, VA
0.47
Single-Family Home
$725,000
11/06/25
6
4
3,917
805 River Strand, Chesapeake, VA
0.69
Single-Family Home
$810,000
05/22/26
5
4.5
3,904
1109 Plantation Lakes Cir, Chesapeake, VA
0.59
Single-Family Home
$565,000
07/21/25
4
2.5
2,554
1305 Gable Way, Chesapeake, VA
0.64
Single-Family Home
$640,000
07/08/26
4
2.5
3,049

Nearby homes

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Assigned Schools

These are the assigned schools for 1355 Simon Dr.
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

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

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Homes for sale near 1355 Simon Dr

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Off Market Homes Near 1355 Simon Dr

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