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$1,229,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 3,345 Sq. Ft.
  • 2 Car Garage
  • Updated 5 days ago
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Don't miss the opportunity to own in the beautiful community of Wellesley at Hidden Meadows, superbly located between downtown Rehoboth Beach and historic downtown Lewes. Tucked along Warrington Road, this desirable location offers exceptional convenience to everyday essentials including grocery stores, shopping, dining, medical facilities and more-all without the need to navigate Route 1. Gently used and beautifully maintained, this exquisite home is situated on a premium, spacious homesite backing to mature trees. The expansive rear yard is already fenced and offers irrigation, built-in garden boxes and plenty of room to create your own private oasis-including space for a future swimming pool. A welcoming front porch sets the tone as you step inside to a thoughtfully designed floor plan that perfectly balances luxury, comfort and functionality. The first level features a private home office, ideal for today's work-from-home lifestyle, along with a guest bedroom and full bath offering privacy and convenience for visiting family and friends. At the heart of the home is an impressive gourmet kitchen featuring an oversized island, quartz countertops, stylish backsplash and abundant cabinetry. Completely open to the dining and living areas, this inviting space was designed for effortless entertaining. A cleverly designed built-in pantry takes functionality to another level, offering generous storage, a dedicated beverage station and plenty of room to tuck away those bulky countertop appliances. Best of all, the main living spaces overlook the sprawling backyard, bringing the peaceful outdoor setting into everyday living. The 1st floor primary suite leaves little to be desired, featuring a luxurious en-suite bath and dual customized walk-in closets designed to maximize every inch of storage. The larger closet even provides direct access to the spacious laundry room-a thoughtful design detail that makes an everyday chore remarkably convenient. Upstairs, a generous yet comfortable loft creates another inviting gathering space where family and guests can spread out and relax. Step outside onto the covered balcony to enjoy cool coastal breezes and peaceful views of the trees and expansive backyard. Two additional guest bedrooms share a full bath, while a spacious walk-in attic provides exceptional storage. Outdoor living is equally impressive. Multiple porches, a built-in grilling station, paver patio with gas firepit, attractive paver walkways and a private yard create the perfect setting for everything from quiet evenings at home to memorable gatherings with friends. Beautifully appointed, exceptionally functional and ideally located between two of Coastal Delaware's most sought-after destinations, this Wellesley at Hidden Meadows residence truly offers the complete package. Luxury, location, space and convenience-this home has it all!

Full Property Details for 18285 Highwood Dr

General

  • Price: $1,229,000
  • HOA FEE: $310/month
  • Taxes: $1,962 (2026)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: DESU2119292
  • Updated: 9/2/2026
  • Added to Site: 6 day(s) ago

Interior

  • Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Kitchen, Laundry, Loft, Office, Bathroom 3, Attic
  • Interior Features: Ceiling Fan(s), Kitchen - Island, Primary Bath(s), Recessed Lighting, Walk-in Closet(s), Combination Kitchen/Living, Dining Area, Entry Level Bedroom, Floor Plan - Open, Pantry, Upgraded Countertops, Wood Floors
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Gas/Propane, Mantel(s)
  • Appliances: Cooktop, Oven - Wall, Refrigerator, Washer, Dryer, Dishwasher, Microwave, Water Heater - Tankless
  • Flooring: Ceramic Tile, Hardwood

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: 4
  • Bedrooms Upper: 2
  • Bedrooms Main & Up: 2

Other Rooms

  • Laundry: Main Floor, Washer In Unit, Dryer In Unit

Additional Information

  • Shared Amenities: Club House, Common Grounds, Fitness Center, Game Room, Meeting Room, Pool - Outdoor
  • Shared Pool: Yes
  • Pool: Yes

Exterior

  • Exterior Features: BBQ Grill, Extensive Hardscape, Exterior Lighting, Gutter System, Lawn Sprinkler, Underground Lawn Sprinkler
  • Porch/Patio/Deck: Porch(es), Deck(s), Patio(s), Screened

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 4
  • Parking Features: Concrete Driveway
  • Parking Type: Attached Garage, Driveway
  • Garage Description: Garage - Front Entry

Location

  • Area: Lewes Rehoboth Hundred (31009)
  • County: SUSSEX
  • Subdivision: WELLESLEY AT HIDDEN MEADOWS
  • Driving Directions: Enter the Wellesley community from Warrington Road. Follow Highwood Drive and take right at the pool. Home will be on the right backing to the woods.
  • Location Details: Middle Of Block

School Information

  • School District: Cape Henlopen
  • Elementary School: Rehoboth
  • Middle School: Beacon
  • High School: Cape Henlopen

Community

  • Association: Yes
  • Assoc. Name: WELLESLEY HOA, INC.
  • Assoc. Fees Include: Common Area Maintenance, Lawn Maintenance, Management, Pool(s), Recreation Facility, Reserve Funds, Road Maintenance, Snow Removal, Trash
  • Pets Allowed: Yes
  • Pets: Dogs OK, Cats OK

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C, Ceiling Fan(s), Zoned
  • Cooling Fuel: Electric
  • Heating Type: Forced Air, Zoned
  • Heating Fuel: Natural Gas
  • Water Heater: Tankless, Natural Gas

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Phone Available, Natural Gas Available

Structural Information

  • Architectural Style: Contemporary
  • Structure Type: Detached
  • Builder: NV Homes
  • Model: Monterey
  • Construction: Blown-In Insulation, Batts Insulation, HardiPlank Type, Stick Built
  • Foundation: Crawl Space
  • Roof: Architectural Shingle
  • Walls/Ceilings: 9'+ Ceilings, Dry Wall
  • Windows: Double Hung, Insulated, Screens
  • Doors: French, Sliding Glass
  • Stories Description: Main, Upper 1
  • Square Feet: 3,345
  • Sq. Ft. Source: Estimated
  • Living Area: 3,345 Sq. Ft.
  • Finished Above Grnd: 3,345 Sq. Ft.
  • Year Built: 2023
  • Year Built Source: Estimated
  • Property Condition: Excellent

Lot Features

  • Property View: Trees/Woods
  • Lot Size (Acres): 0.36
  • Lot Size (Sq. Ft.): 15,512
  • Lot Size Source: Estimated
  • Street/Road Desc.: Black Top
  • Zoning: AR-1
  • Lot Description: Backs to Trees, Front Yard, Landscaping, Premium, Private, Rear Yard
  • Fencing (Description): Rear

Financial Considerations

  • Price Per Sq. Ft.: $367.41
  • Association Fee: $310
  • Assoc Fee Freq.: Monthly
  • Other Fee: $100
  • Other Fee Freq.: One Time
  • Assessment Year: 2026
  • School Tax: $1,763
  • County Tax: $200
  • County Tax Freq: Annually
  • Tax Amount: $1,962
  • Tax Year: 2026

Disclosures and Reports

  • Ownership: Fee Simple
  • Exclusions: Wine fridge in hall storage closet
  • Inclusions: Insta-hot and faucet, whole house filter and softener, beverage fridge in pantry, gas firepit, built in grill, landscape lighting

Listed by Jack Lingo - Rehoboth, SHAUN TULL and Jack Lingo - Rehoboth, AMANDA RYAN

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Listing agents

— 18285 Highwood Dr —

  • SHAUN TULL

    Jack Lingo - Rehoboth

  • AMANDA RYAN

    Jack Lingo - Rehoboth

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

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Schools serving 18285 Highwood Dr

School District:Cape Henlopen School District
NameGradesDistance
Rehoboth Elementary School
500 Stockley Street, Rehoboth Beach, DE 19971
PK-63 mi
Beacon Middle School
19483 John J Williams Highway, Lewes, DE 19958
4-80.3 mi
Cape Henlopen High School
1250 Kings Highway, Lewes, DE 19958
8-123.1 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 18285 Highwood Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/02/2026
Listed
$1,229,000
18.05%
MLS
3/20/2023
Sold
$1,041,070
—
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 18285 Highwood Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$1,970
-12%
100%
2023
$2,248
845%
100%
2022
$238
1%
100%
2021
$235
—
—
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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Listed by Jack Lingo - Rehoboth, SHAUN TULL and Jack Lingo - Rehoboth, AMANDA RYAN

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18285 Highwood Drive, Rehoboth Beach, DE 19971 (MLS# DESU2119292) is a Single Family property with 4 bedrooms and 3 full bathrooms. 18285 Highwood Drive is currently listed for $1,229,000 and was received on September 02, 2026. Want to learn more about 18285 Highwood Drive? Do you have questions about finding other Single Family real estate for sale in Rehoboth Beach? You can browse all Rehoboth Beach real estate or contact a Coldwell Banker agent to request more information.

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