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$424,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 1 Full Bath
  • 1 Partial Bath
  • 1,800 Sq. Ft.
  • 1 Car Garage
  • Updated 1 day ago
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Welcome to one of Denton's most enchanting hidden retreats - a beautifully restored and thoughtfully updated 1941 Cape Cod tucked among towering trees, lush gardens, and comfortable living spaces in the heart of town. Lovingly renovated while preserving its original charm and architectural character, the main residence offers timeless warmth and understated elegance throughout. Rich hardwood flooring, crown molding, custom built-ins, soft natural light, and inviting gathering spaces create an atmosphere that feels both refined and welcoming. The gracious living room features a wood burning fireplace with gas insert, flanked by custom cabinetry and bookshelves, while the spacious dining room and updated kitchen featuring solid wood counters, shelved pantry and storage closet blend classic charm with thoughtful functionality. A screened porch overlooking the gardens provides the perfect setting for morning coffee, evening dinners, or quiet relaxation surrounded by nature. The outdoor setting is truly exceptional. Professionally curated gardens, mature trees, flowering plantings, stone pathways, and intimate seating areas surround a stunning heated in-ground 12X24X4 concrete pool with an additional 5X6 area with steps, creating a private backyard sanctuary rarely found in an in-town setting. Every element of the grounds has been thoughtfully designed to evoke beauty, serenity, and a sense of retreat. Adding remarkable versatility and personality to the property is the detached guest cottage/pool house - this area offers the fourth bedroom and an additional full bath- it's a beautifully finished space with a distinctly relaxed, artistic character featuring soaring wood-beamed ceilings, open-concept living and sleeping areas, kitchenette, and stylish full bath. Perfect for guests, creative studio space, private office, hobbies, or peaceful overflow accommodations, the cottage offers its own unique boutique-retreat ambiance while complementing the timeless elegance of the main home. Extensive improvements completed over time include updated HVAC and ductwork, electrical rewiring and breaker panels, plumbing updates, tankless water heater, insulation improvements, crawlspace vapor barrier, custom remodeling, hardscaping, fencing, buried power lines, driveway improvements, and numerous additional quality enhancements throughout the property. Rarely does a property combine historic charm, curated outdoor living, guest accommodations, and such an inviting sense of place - all conveniently located close to downtown Denton shops, restaurants, waterfront parks, and community events.

Full Property Details for 509 S 2nd St

General

  • Price: $424,900
  • Taxes: $3,101 (2026)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDCM2007478
  • Updated: 7/9/2026
  • Added to Site: 2 day(s) ago

Interior

  • Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Storage Room, Bathroom 1, Bathroom 2, Screened Porch
  • Interior Features: Attic, Built-Ins, Dining Area, Wood Floors
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Gas/Propane, Insert, Wood
  • Appliances: Dishwasher, Disposal, Exhaust Fan, Microwave, Oven - Self Cleaning, Refrigerator, Stove, Washer/Dryer Stacked, Water Heater - Tankless
  • Flooring: Hardwood

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Upper: 3

Other Rooms

  • Laundry: Has Laundry, Dryer In Unit, Washer In Unit, Upper Floor

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Heated, In Ground

Exterior

  • Exterior Features: Extensive Hardscape, Gutter System, Outbuilding(s), Street Lights
  • Porch/Patio/Deck: Porch(es), Screened

Parking

  • Garage: Yes
  • Garage Spaces: 1
  • Total Spaces: 1
  • Parking Type: Attached Garage
  • Garage Description: Garage - Front Entry, Garage Door Opener, Inside Access

Location

  • Municipality: DENTON
  • County: CAROLINE
  • Driving Directions: From MD Route 404, take Denton Business Route ext toward downtown Denton. Continue onto Meeting House Rd and cross Choptank River into town. Stay on Franklin/Gay St to right onto S 2nd St., continue to 509.
  • City Limits: Yes

School Information

  • School District: Caroline County Public Schools

Community

  • Pets Allowed: Yes
  • Pets: Cats OK, Dogs OK

Heating & Cooling

  • Cooling Type: Heat Pump(s)
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Tankless

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Cape Cod
  • Structure Type: Detached
  • Construction: Wood Siding
  • Basement: Yes
  • Basement Desc.: Partial, Interior Access
  • Foundation: Crawl Space
  • Stories Description: Main, Upper 1
  • Square Feet: 1,800
  • Sq. Ft. Source: Estimated
  • Living Area: 1,800 Sq. Ft.
  • Finished Above Grnd: 1,800 Sq. Ft.
  • Year Built: 1941
  • Year Built Source: Estimated
  • Property Condition: Excellent

Additional Structures

  • Other Structures: Guest House

Lot Features

  • Property View: Garden/Lawn, Courtyard
  • Lot Size (Acres): 0.34
  • Lot Size (Sq. Ft.): 15,000
  • Lot Size Source: Estimated
  • Zoning: TR
  • Fencing (Description): Partially

Financial Considerations

  • Price Per Sq. Ft.: $236.06
  • Assessment Year: 2018
  • City/TownTax: $1,712
  • City/TownTax Freq: Annually
  • County Tax: $2,678
  • County Tax Freq: Annually
  • Tax w/Assessment: $175,000
  • Tax Amount: $3,101
  • Tax Year: 2026

Disclosures and Reports

  • Ownership: Fee Simple
  • Inclusions: Parking Included In ListPrice,

Listed by Benson & Mangold, LLC, Judith A Germain

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Listing agent

— 509 S 2nd St —

  • Judith A Germain

    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 509 S 2nd St

School District:Caroline County Public Schools, Denton, MD
NameGradesDistance
Denton Elementary School
303 Sharp Road, Denton, MD 21629
PK-50.6 mi
Lockerman Middle School
410 Lockerman Street, Denton, MD 21629
6-80.9 mi
North Caroline High School
10990 River Road, Ridgely, MD 21660
9-122.2 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 509 S 2nd St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/09/2026
Listed
$424,900
205.68%
MLS
8/17/2011
Sold
$139,000
—
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 509 S 2nd St

Year
Property Taxes
Change
Tax Assessment
Change
2023
$3,266
—
$259,500
12%
2023
$3,266
—
$232,467
13%
2023
$3,266
3%
$205,433
15%
2022
$3,161
63%
$178,400
1%
2017
$1,937
-39%
$177,267
1%
2021
$3,174
1%
$176,133
1%
2020
$3,154
1%
$175,000
—
2019
$3,136
1%
$175,000
—
2018
$3,101
-4%
$175,000
-5%
2017
$3,217
5%
$183,600
5%
2016
$3,057
6%
$175,467
5%
2015
$2,879
8%
$167,333
5%
2014
$2,662
—
$159,200
—
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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NMLS#: 1598647

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Listed by Benson & Mangold, LLC, Judith A Germain

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509 S 2nd Street, Denton, MD 21629 (MLS# MDCM2007478) is a Single Family property with 3 bedrooms, 1 full bathroom and 1 partial bathroom. 509 S 2nd Street is currently listed for $424,900 and was received on July 09, 2026. Want to learn more about 509 S 2nd Street? Do you have questions about finding other Single Family real estate for sale in Denton? You can browse all Denton real estate or contact a Coldwell Banker agent to request more information.

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