Chesapeake by Del Webb. The Hillsboro model offers an exceptional combination of space, convenience, and comfortable living. Located directly across from the Community Center and pool, this home features more than 3,400 square feet of thoughtfully designed living space. The main level includes two generously sized bedrooms and two full bathrooms, along with a separate office, living room, family room with fireplace, and bright sunroom. Upstairs, you'll find an additional bedroom, full bathroom, and spacious living area—ideal for guests, family members, or a private retreat. Step outside to the rear patio, where extensive landscaping creates a beautiful setting for outdoor entertaining, relaxing, or enjoying the surrounding views. With its versatile floor plan, abundant living space, and highly convenient location, the Hillsboro is a home designed for both everyday comfort and entertaining. Recent improvements include a new roof, HVAC system and a new hot water heater
For sale
Price cut: $50K (9/30)
$499,900
29580 Charles Dr, Easton, MD 21601
3beds
3,465sqft
Single Family Residence
Built in 2003
10,032 Square Feet Lot
$485,500 Zestimate®
$144/sqft
$200/mo HOA
What's special
Separate officeRear patioNew roofBright sunroomFamily room with fireplaceTwo generously sized bedroomsVersatile floor plan
- 62 days
- 312
- 14
Zillow last checked:
Listing updated:
Listed by:
Eddie Matthews 410-310-4957,
Benson & Mangold, LLC (410) 822-1415
Source: Bright MLS,MLS#: MDTA2014814
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 3
- Main level bathrooms: 2
- Main level bedrooms: 2
Basement
- Area: 0
Heating
- Forced Air, Natural Gas
Cooling
- Central Air, Electric
Appliances
- Included: Electric Water Heater
Features
- Has basement: No
- Number of fireplaces: 1
Interior area
- Total structure area: 3,465
- Total interior livable area: 3,465 sqft
- Finished area above ground: 3,465
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Garage Faces Rear, Attached
- Attached garage spaces: 2
Accessibility
- Accessibility features: None
Features
- Levels: Two
- Stories: 2
- Pool features: Community
Lot
- Size: 10,032 Square Feet
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 2101102699
- Zoning: R
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Brick, Vinyl Siding
- Foundation: Block, Brick/Mortar, Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 2003
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Senior community: Yes
- Subdivision: Easton Club East
HOA
- Has HOA: Yes
- Amenities included: Billiard Room, Clubhouse, Fitness Center, Game Room, Jogging Path, Library, Meeting Room, Party Room, Picnic Area, Pool, Putting Green, Retirement Community, Tennis Court(s)
- Services included: Maintenance Grounds, Management, Reserve Funds, Snow Removal
- HOA fee: $600 quarterly
Location
- Region: Easton
- Municipality: Easton
Financial & listing details
- Price per square foot: $144/sqft
- Tax assessed value: $497,967
- Annual tax amount: $6,004
- Date on market: 8/21/2026
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
Estimated market value
$485,500
$461,000 - $510,000
$3,504/mo
Price history
| Date | Event | Price |
|---|---|---|
| 9/30/2026 | Price change | $499,900-9.1%$144/sqft |
Source:  Bright MLS #MDTA2014814 Report a problem | ||
| 9/4/2026 | Price change | $549,900-1.6%$159/sqft |
Source: Bright MLS #MDTA2014814 Report a problem | ||
| 8/21/2026 | Listed for sale | $559,000+69.4%$161/sqft |
Source: Bright MLS #MDTA2014814 Report a problem | ||
| 2/4/2004 | Sold | $330,065$95/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2026 | $2,497 +3.4% | $497,967 +8% |
| 2025 | $2,414 -55.9% | $461,033 +8.7% |
| 2024 | $5,471 +11% | $424,100 +6.9% |
| 2023 | $4,927 +13.1% | $396,567 -6.5% |
| 2022 | $4,358 +12.3% | $424,100 +24.2% |
| 2021 | $3,880 | $341,500 |
| 2020 | $3,880 | $341,500 |
| 2019 | $3,880 -5.4% | $341,500 -8% |
| 2018 | $4,100 +8.1% | $371,000 +4.7% |
| 2017 | $3,792 +154.6% | $354,467 +4.9% |
| 2016 | $1,490 | $337,933 +5.1% |
| 2015 | $1,490 +12.6% | $321,400 |
| 2014 | $1,322 | $321,400 |
| 2013 | -- | $321,400 -16% |
| 2012 | -- | $382,400 |
| 2011 | -- | $382,400 |
| 2010 | -- | $382,400 -9.3% |
| 2009 | -- | $421,450 +10.8% |
| 2008 | -- | $380,200 +12.2% |
| 2007 | -- | $338,950 +13.9% |
| 2006 | -- | $297,700 +2.5% |
| 2005 | -- | $290,406 +0.3% |
| 2004 | -- | $289,610 |
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: 21601
Nearby schools
Schools provided by the listing agent
- District: Talbot County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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