Luxury Redefined at 1301 Simon Drive Experience the pinnacle of Chesapeake living in this custom 5,612 sq. ft. brick estate. Nestled on a spacious corner lot in Greenbrier, this 6-bed, 4.5-bath masterpiece blends timeless elegance with modern high-tech luxury. The Interior Experience: Ultimate Comfort: Enjoy radiant heated floors Chef’s Dream: Gourmet kitchen with high-end appliances and a sleek wet bar. Grand Design: Cathedral ceilings and a dramatic winding staircase. Your Private Oasis: Step outside to a brand-new, gorgeous pool oasis. Whether you're hosting a summer gala or a quiet evening by the water, this backyard is designed for pure relaxation. The Bells & Whistles: Oversized 3-car garage. Lavish primary suite with a champagne bubble spa-tub. Premium finishes and smart-home integration throughout. 1301 Simon Drive | Luxury is in the details.
Under contract
Price cut: $122K (7/13)
$1,075,000
1301 Simon Dr, Chesapeake, VA 23320
6beds
5,612sqft
Single Family Residence
Built in 2005
0.41 Acres Lot
$1,070,500 Zestimate®
$192/sqft
$45/mo HOA
What's special
- 77 days |
- 1,681 |
- 95 |
Zillow last checked:
Listing updated:
Listed by:
Eugene Shull,
KW Metro Center 805-858-9000
Source: REIN Inc.,MLS#: 10632029
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Rooms
- Room types: Attic, Breakfast Area, PBR with Bath, Office/Study
Heating
- Forced Air
Cooling
- Central Air
Appliances
- Included: Dishwasher, Disposal, Dryer, Microwave, Gas Range, Refrigerator, Washer, Gas Water Heater
- Laundry: Dryer Hookup, Washer Hookup
Features
- Cathedral Ceiling(s), Dual Entry Bath (Br & Br), Primary Sink-Double, Walk-In Closet(s), Entrance Foyer, Pantry
- Flooring: Bamboo, Carpet, Ceramic Tile, Wood
- Basement: Crawl Space
- Attic: Permanent Stairs,Walk-In
- Number of fireplaces: 1
- Fireplace features: Fireplace Gas-natural
Interior area
- Total interior livable area: 5,612 sqft
Video & virtual tour
Property
Parking
- Total spaces: 3
- Parking features: Garage Att 3+ Car, 3 Space
- Attached garage spaces: 3
Features
- Stories: 3
- Patio & porch: Deck, Patio
- Exterior features: Inground Sprinkler
- Pool features: In Ground
- Fencing: Back Yard,Fenced
- Waterfront features: Not Waterfront
Lot
- Size: 0.41 Acres
Details
- Parcel number: 0294001000800
- Zoning: R15S
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Brick
- Roof: Asphalt Shingle
Condition
- New construction: No
- Year built: 2005
Utilities & green energy
- Sewer: City/County
- Water: City/County
- Utilities for property: Cable Hookup
Community & HOA
Community
- Subdivision: Emerald Forest
HOA
- Has HOA: Yes
- HOA fee: $45 monthly
Location
- Region: Chesapeake
Financial & listing details
- Price per square foot: $192/sqft
- Tax assessed value: $1,007,100
- Annual tax amount: $10,172
- Date on market: 5/1/2026
Estimated market value
$1,070,500
$1.02M - $1.12M
$4,632/mo
Price history
Price history is unavailable.
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $10,172 +9.2% | $1,007,100 +9.2% |
| 2024 | $9,313 +2.7% | $922,100 +2.7% |
| 2023 | $9,071 +11.4% | $898,100 +15.8% |
| 2022 | $8,145 +12.5% | $775,700 +12.5% |
| 2021 | $7,238 | $689,300 +3.4% |
| 2020 | -- | $666,600 -2.2% |
| 2019 | $7,157 +11.3% | $681,600 |
| 2018 | $6,431 -2% | $681,600 +9% |
| 2017 | $6,566 +2.1% | $625,300 +2.1% |
| 2016 | $6,431 | $612,500 |
| 2015 | $6,431 | $612,500 +4.8% |
| 2014 | $6,431 +9.8% | $584,700 +4.9% |
| 2013 | $5,855 | $557,600 |
| 2012 | $5,855 -5.1% | $557,600 -5.1% |
| 2011 | $6,170 -7.8% | $587,600 -7.8% |
| 2010 | $6,695 -3% | $637,600 -3% |
| 2009 | $6,905 -21.1% | $657,600 -21.1% |
| 2008 | $8,752 -0.2% | $833,500 +0.7% |
| 2007 | $8,774 -2% | $827,700 +2.6% |
| 2006 | $8,957 | $806,900 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: Greenbrier East
Nearby schools
GreatSchools rating
- 6/10Greenbrier Primary SchoolGrades: PK-2Distance: 0.8 mi
- 7/10Greenbrier Middle SchoolGrades: 6-8Distance: 1.3 mi
- 4/10Indian River High SchoolGrades: 9-12Distance: 2.4 mi
Schools provided by the listing agent
- High: Indian River
Source: REIN Inc.. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
- $920,0005 bd4 ba3.8k sqft1523 Peyton Ln, Chesapeake, VA 23320Sold
- $970,1005 bd4 ba4.1k sqft1303 Simon Dr, Chesapeake, VA 23320Off Market
- $1,238,0005 bd4 ba5.7k sqft1535 Peyton Ln, Chesapeake, VA 23320Off Market
- $1,067,8005 bd4 ba4.6k sqft1519 Peyton Ln, Chesapeake, VA 23320Off Market
- $1,022,0005 bd4 ba3.5k sqft1528 Peyton Ln, Chesapeake, VA 23320Off Market
- $1,009,7005 bd4 ba3.6k sqft1532 Peyton Ln, Chesapeake, VA 23320Off Market
- $935,0005 bd4 ba3.5k sqft1302 Simon Dr, Chesapeake, VA 23320Off Market
- $1,094,2006 bd5 ba4.6k sqft1524 Peyton Ln, Chesapeake, VA 23320Off Market
A local agent can set up tours, give advice and negotiate with sellers.
Similar homes
- $999,9996 bd4 ba4.7k sqft821 Redleafe Cir, Chesapeake, VA 23320For Sale
MLS ID #10642513, Alison Keech. REIN Inc. - $1,195,0006 bd4 ba5.3k sqft520 Youngstown Ct, Chesapeake, VA 23322For Sale
MLS ID #10639257, Emilee Davis. REIN Inc. - $1,190,0006 bd5 ba6.3k sqft4200 Quailshire Ct, Chesapeake, VA 23321For Sale
MLS ID #10639205, Anna Paduhovich. REIN Inc. - $950,0005 bd4 ba3.8k sqft129 Greengable Way, Chesapeake, VA 23322For Sale
MLS ID #10642562, Betsy Thompson. REIN Inc. - $1,229,0005 bd4 ba3.8k sqft1905 Lancing Crest Ln, Chesapeake, VA 23323For SaleMLS ID #10641173, Robin Tuxill. REIN Inc.
- $935,0006 bd4 ba3.7k sqft409 Torre Pine Ct, Chesapeake, VA 23322For SaleMLS ID #10642291, Kim McGlone. REIN Inc.
- $975,0005 bd6 ba4.6k sqft3000 Miars Grn, Chesapeake, VA 23321For SaleMLS ID #10642217, Laura McGuire. REIN Inc.
- $1,200,0004 bd4 ba4.3k sqft1625 Water View Cir, Chesapeake, VA 23322For SaleMLS ID #10630708, Michele Obenour. REIN Inc.
- $1,325,0005 bd4 ba5.6k sqft1149 Waters Rd, Chesapeake, VA 23322For SaleMLS ID #10620633, Kesha Wilkey-Prim. REIN Inc.
- $820,0005 bd5 ba4.9k sqft700 Harbor Quay, Chesapeake, VA 23320For SaleMLS ID #10639536, Jean Vines. REIN Inc.
- $685,0005 bd3 ba3.2k sqft813 Loch Island Dr, Chesapeake, VA 23320For SaleMLS ID #10639539, Laura McGuire. REIN Inc.
- $754,9005 bd3 ba3.4k sqft404 Vespasian Cir, Chesapeake, VA 23322For SaleMLS ID #10637123, Thomas Milan. REIN Inc.
- $1,100,0005 bd4 ba3.7k sqft2704 Indian Creek Ct, Virginia Beach, VA 23457For SaleMLS ID #10641900, Rusty Hulett. REIN Inc.
- $715,0005 bd3 ba2.9k sqft4305 Indian River Rd, Virginia Beach, VA 23456For SaleMLS ID #10643012, Micah Laurendeau. REIN Inc.
- $1,149,0006 bd5 ba4.5k sqft536 Thistley Ln, Chesapeake, VA 23322For SaleMLS ID #10626451, Mina Wang. REIN Inc.
- $800,0005 bd4 ba3.6k sqft915 Shelter Rock Ln, Chesapeake, VA 23322For SaleMLS ID #10636961, Greg Garrett. REIN Inc.
- $1,149,0005 bd5 ba4.5k sqft2280 Rio Rancho Dr, Virginia Beach, VA 23456For SaleMLS ID #10633671, Mandy Farmer. REIN Inc.
- $1,200,0006 bd4 ba4.9k sqft2276 Rio Rancho Dr, Virginia Beach, VA 23456For SaleMLS ID #10640581, June Surbaugh. REIN Inc.
- $715,0005 bd3 ba3.1k sqft581 Hunts Pointe Dr, Virginia Beach, VA 23464For SaleMLS ID #10642828, Ryan Ryckman. REIN Inc.
- $924,9005 bd3 ba3.7k sqft804 Casa Verde Way, Virginia Beach, VA 23456For SaleMLS ID #10643030, Dakota Bush. REIN Inc.
