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$559,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 3,465 Sq. Ft.
  • 2 Car Garage
  • Updated 2 days ago

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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

Full Property Details for 29580 Charles Dr

General

  • Price: $559,000
  • HOA FEE: $200/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $6,004 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDTA2014814
  • Updated: 8/24/2026
  • Added to Site: 5 day(s) ago

Interior

  • Fireplace: Yes
  • Number of Fireplaces: 1

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Upper Floor Baths: 1
  • Upper - Full Baths: 1
  • Main Floor Baths: 2
  • Main - Full Baths: 2

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Upper: 1
  • Bedrooms Main & Up: 2

Additional Information

  • Shared Amenities: Billiard Room, Club House, Exercise Room, Game Room, Jog/Walk Path, Library, Meeting Room, Party Room, Picnic Area, Pool - Outdoor, Putting Green, Retirement Community, Tennis Courts
  • Shared Pool: Yes
  • Pool: Yes

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Type: Attached Garage
  • Garage Description: Garage - Rear Entry

Location

  • Municipality: Easton
  • County: TALBOT
  • Subdivision: EASTON CLUB EAST
  • Driving Directions: Dutchmans Lane to a left on Lyons Drive to a left on Charles Dr. Property will be on your right.
  • City Limits: Yes

School Information

  • School District: Talbot County Public Schools

Community

  • Association: Yes
  • Assoc. Fees Include: Lawn Maintenance, Management, Reserve Funds, Snow Removal
  • Adult Community: Yes

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Forced Air
  • Heating Fuel: Natural Gas
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Colonial
  • Structure Type: Detached
  • Construction: Brick, Vinyl Siding
  • Foundation: Block, Brick/Mortar, Concrete Perimeter
  • Roof: Asphalt
  • Stories Description: Main, Upper 1
  • Square Feet: 3,465
  • Sq. Ft. Source: Assessor
  • Living Area: 3,465 Sq. Ft.
  • Finished Above Grnd: 3,465 Sq. Ft.
  • Year Built: 2003
  • Year Built Source: Assessor

Lot Features

  • Lot Size (Acres): 0.23
  • Lot Size (Sq. Ft.): 10,032
  • Lot Size Source: Assessor
  • Zoning: R

Financial Considerations

  • Price Per Sq. Ft.: $161.33
  • Association Fee: $600
  • Assoc Fee Freq.: Quarterly
  • Assessment Year: 2026
  • City/TownTax: $2,397
  • City/TownTax Freq: Annually
  • County Tax: $3,606
  • County Tax Freq: Annually
  • Tax w/Assessment: $497,967
  • Tax Amount: $6,004
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 3465

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 413

Listed by Benson & Mangold, LLC, Edwin M Matthews

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Listing agent

— 29580 Charles Dr —

  • Edwin M Matthews

    Benson & Mangold, LLC

Listing Office Email: info@bensonandmangold.com

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 29580 Charles Dr

School District:Talbot County Public Schools
NameGradesDistance
Easton Elementary School
307 Glenwood Avenue, Easton, MD 21601
PK-52.4 mi
Easton Middle School
201 Peachblossom Road, Easton, MD 21601
6-81.6 mi
Easton High School
723 Mecklenburg Avenue, Easton, MD 21601
9-120.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 29580 Charles Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/21/2026
Listed
$559,000
69.36%
MLS
2/04/2004
Sold
$330,070
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 29580 Charles Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,395
-15%
$497,967
8%
2023
$2,811
—
$461,033
9%
2023
$2,811
—
$424,100
7%
2023
$2,811
-35%
$396,567
7%
2022
$4,358
141%
$369,033
8%
2020
$1,810
1%
$341,500
—
2021
$1,796
—
$341,500
—
2020
$1,796
2%
$341,500
-8%
2019
$1,755
7%
$371,000
5%
2018
$1,636
5%
$354,467
5%
2017
$1,551
3%
$337,933
5%
2016
$1,501
2%
$321,400
—
2015
$1,478
3%
$321,400
—
2014
$1,436
—
$321,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Benson & Mangold, LLC, Edwin M Matthews

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29580 Charles Drive, Easton, MD 21601 (MLS# MDTA2014814) is a Single Family property with 3 bedrooms and 3 full bathrooms. 29580 Charles Drive is currently listed for $559,000 and was received on August 21, 2026. Want to learn more about 29580 Charles Drive? Do you have questions about finding other Single Family real estate for sale in Easton? You can browse all Easton real estate or contact a Coldwell Banker agent to request more information.

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