Waterfront living at its best! Nestled in the desirable Holland Pines neighborhood, 1729 Chestwood Drive offers the perfect blend of comfort, charm, and outdoor beauty. With 4 bedrooms and 2.5 baths, this 2,626 sq. ft. home features hardwood floors, vaulted ceilings, and a gorgeous clawfoot tub for spa-like relaxation. The updated kitchen opens to bright living spaces and a cozy gas fireplace, while upstairs bedrooms offer plenty of space for the whole family. Step outside to a private 0.56-acre lot with wooded government land on two sides for privacy and endless water views. Enjoy evenings on the wraparound porch, large deck with retractable awning, or waterside patio. Schools include Christopher Farms Elementary and Landstown Middle/High. Convenient to Oceana, Dam Neck, shopping, and dining—this home truly has it all! No HOA!
Sold
$689,900
1729 Chestwood Dr, Virginia Beach, VA 23453
4beds
2,626sqft
Single Family Residence
Built in 1995
0.56 Acres Lot
$712,500 Zestimate®
$263/sqft
$3,261 Estimated rent
Home value
$712,500
$670,000 - $762,000
$3,261/mo
Zestimate® history
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List your homeWhat's special
Waterfront livingCozy gas fireplaceBright living spacesEndless water viewsWaterside patioWraparound porchVaulted ceilings
Zillow last checked:
Listing updated:
Listed by:
Eddie Gerardo-Ferrer,
RE/MAX Allegiance 757-490-7300
Bought with:
Anne Asercion
Swell Real Estate Co
Source: REIN Inc.,MLS#: 10602060
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Rooms
- Room types: Attic, Breakfast Area, Fin. Rm Over Gar, PBR with Bath, Utility Room
Heating
- Forced Air, Natural Gas, Zoned
Cooling
- Central Air, Zoned
Appliances
- Included: Dishwasher, Disposal, Microwave, Gas Range, Refrigerator, Electric Water Heater
Features
- Primary Sink-Double, Walk-In Closet(s), Ceiling Fan(s)
- Flooring: Carpet, Ceramic Tile, Laminate/LVP
- Basement: Crawl Space
- Attic: Pull Down Stairs
- Number of fireplaces: 1
- Fireplace features: Fireplace Gas-natural
Interior area
- Total interior livable area: 2,626 sqft
Property
Parking
- Total spaces: 2
- Parking features: Garage Att 2 Car, Driveway, Garage Door Opener
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Stories: 2
- Patio & porch: Deck, Patio, Porch
- Pool features: None
- Fencing: Partial,Fenced
- Has view: Yes
- View description: Water, Trees/Woods
- Has water view: Yes
- Water view: Water
- Waterfront features: Lake Front
Lot
- Size: 0.56 Acres
Details
- Parcel number: 14957021240000
- Zoning: R10
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Roof: Composition
Condition
- New construction: No
- Year built: 1995
Utilities & green energy
- Sewer: City/County
- Water: City/County
Community & HOA
Community
- Subdivision: Holland Pines
HOA
- Has HOA: No
Location
- Region: Virginia Beach
Financial & listing details
- Price per square foot: $263/sqft
- Tax assessed value: $523,900
- Annual tax amount: $5,082
- Date on market: 9/19/2025
Price history
Price history is unavailable.
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $5,082 +3.1% | $523,900 +5.2% |
| 2024 | $4,928 +0.9% | $497,800 +0.9% |
| 2023 | $4,885 +10.3% | $493,400 +10.3% |
| 2022 | $4,429 +13.4% | $447,400 +13.4% |
| 2021 | $3,906 0% | $394,500 +11.8% |
| 2020 | $3,907 +16.8% | $352,800 +5.7% |
| 2019 | $3,346 | $333,800 |
| 2018 | $3,346 +2.9% | $333,800 +2.9% |
| 2017 | $3,252 +0.6% | $324,400 -0.6% |
| 2016 | $3,232 -0.7% | $326,500 -0.7% |
| 2015 | $3,254 | $328,700 +8.8% |
| 2014 | $3,254 | $302,200 -4.5% |
| 2013 | -- | $316,600 +4.7% |
| 2012 | -- | $302,300 |
| 2011 | -- | $302,300 -6.4% |
| 2010 | -- | $323,100 -10.1% |
| 2007 | -- | $359,530 +20.3% |
| 2006 | -- | $298,766 +14.6% |
| 2005 | -- | $260,636 +20.4% |
| 2004 | -- | $216,498 +13.7% |
| 2003 | -- | $190,490 +4.7% |
| 2002 | -- | $181,864 |
| 2001 | -- | $181,864 |
Find assessor info on the county website
Neighborhood: Princess Anne
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Nearby schools
GreatSchools rating
- 9/10Christopher Farms Elementary SchoolGrades: PK-5Distance: 0.5 mi
- 8/10Landstown Middle SchoolGrades: 6-8Distance: 2.5 mi
- 6/10Landstown High SchoolGrades: 9-12Distance: 2.3 mi
Schools provided by the listing agent
- Elementary: Christopher Farms Elementary
- Middle: Landstown Middle
- High: Landstown
Source: REIN Inc.. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Virginia
- Virginia Beach City
- Virginia Beach
- 23453
- Princess Anne
- 1729 Chestwood Dr
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