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$539,900

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 2,136 Sq. Ft.
  • 2 Car Garage
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Perfectly positioned on a premium homesite backing to mature woods, this beautifully appointed 3-bedroom, 2-bath home offers rare privacy, stunning natural light, and seamless indoor-outdoor living - all within an amenity-rich community featuring a pool, playground, and fitness center, just minutes from the beach. From the moment you step inside, you're greeted by soaring two-story ceilings and upper-level windows that flood the home with natural light, creating a bright, airy ambiance throughout the open floor plan. Engineered hardwood floors, a cozy fireplace, and refined finishes add warmth and sophistication while maintaining a relaxed coastal feel. The gourmet kitchen is both stylish and functional, showcasing quartz countertops, a gas range, subway tile backsplash, an oversized island ideal for gathering, and a brand-new French door refrigerator. The formal dining room is accented with elegant wainscoting, offering the perfect backdrop for holidays and special occasions. The primary suite serves as a peaceful retreat with serene wooded views and beautiful natural light. The en suite bath features split double vanities, a step-in shower, private water closet, and a spacious walk-in closet designed for effortless organization. Upstairs, the versatile loft provides flexible space for a second living area, home office, media room, or gym - ideal for today's lifestyle. But the true highlight of this home is the exceptional outdoor living space. The screened-in porch with vaulted ceilings feels like an extension of the home, offering the perfect place to enjoy morning coffee, evening cocktails, or quiet afternoons surrounded by nature. Just beyond, an oversized deck provides ample room for grilling, dining, and gathering around a firepit - all overlooking a private, wooded backdrop that ensures year-round tranquility and no rear neighbors. Additional features include a built-in desk area, mudroom/laundry room, plantation shutters throughout, and a 2-car garage with extra storage. This is more than a home - it's a peaceful coastal retreat where natural beauty, thoughtful design, and effortless entertaining come together beautifully. Schedule your private showing today!

Full Property Details for 29570 Ashland Dr

General

  • Price: $539,900
  • HOA FEE: $229/month
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: DESU2106028
  • Updated: 3/6/2026
  • Added to Site: 45 day(s) ago

Interior

  • Rooms/Areas: Dining Room, Primary Bedroom, Bedroom 2, Kitchen, Family Room, Bedroom 1, Loft, Bathroom 2, Primary Bathroom, Screened Porch
  • Interior Features: Ceiling Fan(s), Carpet, Recessed Lighting, Built-Ins, Bathroom - Stall Shower, Bathroom - Tub Shower, Dining Area, Floor Plan - Open, Kitchen - Island, Primary Bath(s), Upgraded Countertops, Wainscotting
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Mantel(s), Gas/Propane
  • Appliances: Built-In Microwave, Built-In Range, Dishwasher, Disposal, Dryer, Exhaust Fan, Refrigerator, Stainless Steel Appliances, Washer, Water Heater
  • Flooring: Carpet, Ceramic Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Main Floor Baths: 2
  • Main - Full Baths: 2

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Main & Up: 3

Other Rooms

  • Laundry: Has Laundry

Additional Information

  • Shared Amenities: Club House, Exercise Room, Fitness Center, Game Room, Jog/Walk Path, Meeting Room, Pool - Outdoor, Tot Lots/Playground, Common Grounds
  • Shared Pool: Yes
  • Pool: Yes
  • Security/Safety: Carbon Monoxide Detector(s), Smoke Detector

Exterior

  • Porch/Patio/Deck: Deck(s), Porch(es), Screened

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Features: Asphalt Driveway
  • Parking Type: Attached Garage, Driveway
  • Garage Description: Garage - Front Entry

Location

  • Area: Indian River Hundred (31008)
  • County: SUSSEX
  • Subdivision: WOODRIDGE
  • Driving Directions: Use GPS for most accurate directions

School Information

  • School District: Cape Henlopen

Community

  • Association: Yes
  • Assoc. Fees Include: Common Area Maintenance, Lawn Maintenance, Recreation Facility, Management, Pool(s), Reserve Funds, Trash

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Forced Air
  • Heating Fuel: Electric, Propane - Metered
  • Water Heater: Tankless

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Contemporary
  • Structure Type: Detached
  • Construction: Stick Built
  • Foundation: Crawl Space
  • Walls/Ceilings: 2 Story Ceilings, Wood Ceilings
  • Doors: Sliding Glass
  • Stories Description: Main
  • Square Feet: 2,136
  • Sq. Ft. Source: Estimated
  • Living Area: 2,136 Sq. Ft.
  • Finished Above Grnd: 2,136 Sq. Ft.
  • Year Built: 2022
  • Year Built Source: Estimated
  • Property Condition: Excellent

Lot Features

  • Property View: Trees/Woods
  • Lot Size (Acres): 0.2
  • Lot Size (Sq. Ft.): 8,712
  • Lot Size Source: Estimated
  • Lot Dimensions: 75.00 x 119.00
  • Zoning: AR-1
  • Lot Description: Backs to Trees

Financial Considerations

  • Price Per Sq. Ft.: $252.76
  • Association Fee: $229
  • Assoc Fee Freq.: Monthly

Disclosures and Reports

  • Ownership: Fee Simple

Listed by Jack Lingo - Lewes, Chelsea Rose Bristow

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Listing agent

— 29570 Ashland Dr —

  • Chelsea Rose Bristow

    Jack Lingo - Lewes

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 29570 Ashland Dr

School District:Cape Henlopen School District
NameGradesDistance
Beacon Middle School
19483 John J Williams Highway, Lewes, DE 19958
4-85.1 mi
Cape Henlopen High School
1250 Kings Highway, Lewes, DE 19958
8-126.8 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 29570 Ashland Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/04/2026
Listed
$539,900
2.43%
MLS
6/08/2022
Sold
$527,115
—
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 29570 Ashland Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$1,250
-15%
$3,550
—
2023
$1,470
4%
$3,550
—
2022
$1,419
643%
$3,550
—
2021
$191
100%
$3,550
—
2020
—
$3,550
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 29570 Ashland Dr

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Listed by Jack Lingo - Lewes, Chelsea Rose Bristow

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29570 Ashland Drive, Milton, DE 19968 (MLS# DESU2106028) is a Single Family property with 3 bedrooms and 2 full bathrooms. 29570 Ashland Drive is currently listed for $539,900 and was received on March 04, 2026. Want to learn more about 29570 Ashland Drive? Do you have questions about finding other Single Family real estate for sale in Milton? You can browse all Milton real estate or contact a Coldwell Banker agent to request more information.

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