Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$1,299,999 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 5,400 Sq. Ft.
  • 2 Car Garage
  • Updated 8 hours ago

Next open house:

Open House: 11:00 AM - 1:00 PM

Saturday 9/12 11:00 AM - 1:00 PM

18037 Highwood Drive,Rehoboth Beach, DE 19971

18037 Highwood DriveRehoboth BeachDE19971

Get directions
See This Home
Save This Home
See This Home
Save This Home
This exquisite former model home in the Wellesley community offers exceptional indoor and outdoor living just minutes from Lewes and Rehoboth Beach. Situated on a Spacious Lot with wooded backdrop for added privacy, the Fenced Backyard is designed for entertaining and relaxation, featuring an expansive Brand New Paver Patio, with Heated Saltwater Plunge Pool and Outdoor Kitchen. With the ability to reach temperatures up to 104°F, the pool can also be enjoyed hot-tub style throughout the year-creating your own private backyard retreat in every season. A welcoming Covered Front Porch leads into the open Foyer, with a Private Office just off the entry. Continue past the first Main-level Bedroom into the bright and airy living area, where you will find a Spacious Great Room and Gourmet Kitchen with an oversized center island that flows seamlessly into the living and dining spaces. Just off the Great Room, the Covered Porch features natural gas heaters, extending the enjoyment of this inviting space throughout the year. The main level also features a spacious Primary Suite with Dual Vanities and a generous Walk-in Closet with custom shelving. Upstairs, a spacious Living Room opens to another Covered Porch and is joined by two additional Bedrooms, a full Bath, and a substantial unfinished space offering the potential for storage or future expansion. The Finished Basement adds an entire additional level of living space and is perfectly set up for entertaining, relaxing, and recreation. It features an Entertainment Room with Dry bar, a spacious living and lounge area, dedicated Exercise Room, Full Bathroom, and a utility room or workshop & abundant storage-providing plenty of room for family and guests while adding tremendous versatility to the home. Custom Plantation style shutters will be professionally installed prior to closing. Just down the block, enjoy the Community Clubhouse, Fitness Center, and Pool. With multiple indoor and outdoor living spaces, a private backyard retreat designed for year-round enjoyment, and a convenient location near the beaches, shopping, dining, and everything the Lewes-Rehoboth area has to offer, this exceptional home is ready to be enjoyed!

Full Property Details for 18037 Highwood Dr

General

  • Price: $1,299,999
  • HOA FEE: $310/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $2,007 (2026)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: DESU2120312
  • Updated: 9/11/2026
  • Added to Site: 1 day(s) ago

Interior

  • Rooms/Areas: 2nd Stry Fam Rm, Exercise Room, Laundry, Storage Room, Utility Room
  • Flooring: Carpet, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4
  • Upper Floor Baths: 1
  • Upper - Full Baths: 1
  • Main Floor Baths: 2
  • Main - Full Baths: 2
  • Lower Floor Baths: 1
  • Lower - Full Baths: 1

Bedrooms

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

Additional Information

  • Shared Amenities: Bar/Lounge, Club House, Exercise Room, Pool - Outdoor
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Concrete, Heated, In Ground, Saltwater

Exterior

  • Exterior Features: BBQ Grill, Extensive Hardscape, Exterior Lighting, Flood Lights, Play Area, Stone Retaining Walls, Underground Lawn Sprinkler
  • Porch/Patio/Deck: Patio(s), Porch(es), Balcony

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 6
  • Parking Type: Attached Garage, Driveway
  • Garage Description: Garage - Front Entry, Garage Door Opener, Inside Access

Location

  • Area: Lewes Rehoboth Hundred (31009)
  • County: SUSSEX
  • Subdivision: WELLESLEY AT HIDDEN MEADOWS
  • Driving Directions: From Route one South turn right onto Route 24 West. Then left onto Warrington Road and turn right onto Highwood Drive.

School Information

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

Community

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

Heating & Cooling

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

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Coastal, Traditional
  • Structure Type: Detached
  • Construction: HardiPlank Type, Stick Built
  • Basement: Yes
  • Basement Entrance: Yes
  • Basement Desc.: Connecting Stairway, Fully Finished, Interior Access, Outside Entrance, Rear Entrance, Side Entrance, Sump Pump, Walkout Stairs
  • Foundation: Concrete Perimeter
  • Roof: Architectural Shingle
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 5,400
  • Sq. Ft. Source: Estimated
  • Living Area: 4,800 Sq. Ft.
  • Finished Above Grnd: 3,400 Sq. Ft.
  • Finished Below Grnd: 1,400 Sq. Ft.
  • Year Built: 2021
  • Year Built Source: Estimated

Unit Information

Unit 1

  • Bathrooms-Lower: 1

Lot Features

  • Property View: Trees/Woods
  • Lot Size (Acres): 0.23
  • Lot Size (Sq. Ft.): 10,000
  • Lot Size Source: Estimated
  • Zoning: RS
  • Lot Description: Backs to Trees, Front Yard, Premium, Private, Rear Yard
  • Fencing (Description): Aluminum

Financial Considerations

  • Price Per Sq. Ft.: $382.35
  • Association Fee: $930
  • Assoc Fee Freq.: Quarterly
  • School Tax: $1,802
  • County Tax: $204
  • Tax w/Assessment: $953,700
  • Tax Amount: $2,007
  • Tax Year: 2026

Disclosures and Reports

  • Ownership: Fee Simple

Listed by Patterson-Schwartz-Rehoboth, CASSANDRA ROGERSON and Patterson-Schwartz-Rehoboth, Jessica White Harrison

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agents

— 18037 Highwood Dr —

  • CASSANDRA ROGERSON

    Patterson-Schwartz-Rehoboth

  • Jessica White Harrison

    Patterson-Schwartz-Rehoboth

Listing Office Email: jgiles@psre.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 18037 Highwood Dr

School District:Cape Henlopen School District
NameGradesDistance
Rehoboth Elementary School
500 Stockley Street, Rehoboth Beach, DE 19971
PK-62.8 mi
Beacon Middle School
19483 John J Williams Highway, Lewes, DE 19958
4-80.6 mi
Cape Henlopen High School
1250 Kings Highway, Lewes, DE 19958
8-122.7 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 18037 Highwood Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/10/2026
Listed
$1,299,999
36.84%
MLS
8/27/2025
Sold
$950,000
—
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 18037 Highwood Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,014
-19%
100%
2023
$2,492
—
100%
2023
$2,489
4%
100%
2022
$2,403
923%
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.

Estimate the Cost for 18037 Highwood Dr

$
Down Payment
%
$
%

$
$
$

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

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Patterson-Schwartz-Rehoboth, CASSANDRA ROGERSON and Patterson-Schwartz-Rehoboth, Jessica White Harrison

Similar Properties near 18037 Highwood Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

230 Clara Ln, Lewes, DE 19958 - Photo 1
$1,340,400

230 Clara Ln  Lewes, DE 19958

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 2,478
    Sq. Ft.
Listed by Monument Sotheby's International Realty, HENRY A JAFFE
149 Glade Cir W, Rehoboth Beach, DE 19971 - Photo 1
$1,250,000
Open House

149 Glade Cir W  Rehoboth Beach, DE 19971

  • Single Family
  • Active
  • Updated 8 hours ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,400
    Sq. Ft.
Listed by Compass, Edith Chilelli
30769 Edgewater Dr, Lewes, DE 19958 - Photo 1
$1,225,000

30769 Edgewater Dr  Lewes, DE 19958

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 2,515
    Sq. Ft.
Listed by Northrop Realty, Noah Crofton Bates
412 Kings Hwy, Lewes, DE 19958 - Photo 1 Price Reduced
-$101,000 (-7.48%)
$1,249,000

412 Kings Hwy  Lewes, DE 19958

  • Single Family
  • Active
  • Updated 23 hours ago
  • 4
    Beds
  • 3
    Total Baths
  • 1,909
    Sq. Ft.
Listed by Monument Sotheby's International Realty, Brian K Barrows and Monument Sotheby's International Realty, JENNIFER BARROWS

Just Listed near 18037 Highwood Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

7 Sand Dune Dr, Dewey Beach, DE 19971 - Photo 1 Just Listed
$3,995,000

7 Sand Dune Dr  Dewey Beach, DE 19971

  • Single Family
  • Active
  • Updated 21 hours ago
  • 6
    Beds
  • 4
    Total Baths
  • 3,200
    Sq. Ft.
Listed by Monument Sotheby's International Realty, Justin Noble
33725 Skiff Aly, Lewes, DE 19958 - Photo 1 Just Listed
$375,000
Open House

33725 Skiff Aly  #304  Lewes, DE 19958

  • Condo
  • Active
  • Updated 22 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,369
    Sq. Ft.
Listed by Catina Fair (443) 528-4424
32191 Nassau Rd, Lewes, DE 19958 - Photo 1 Just Listed
$19

32191 Nassau Rd  #2  Lewes, DE 19958

  • Commercial Lease
  • Active
Listed by R&R Commercial Realty, Keith Walpole and R&R Commercial Realty, Marie Biro
33737 Skiff Aly, Lewes, DE 19958 - Photo 1 Just Listed
$649,999

33737 Skiff Aly  Lewes, DE 19958

  • Condo
  • Active
  • Updated 10 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,634
    Sq. Ft.
Listed by Sell Your Home Services, Daniel J. Demers

Price Reduced near 18037 Highwood Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

16512 Greenspring Ave, Lewes, DE 19958 - Photo 1 Price Reduced
-$20,000 (-3.18%)
$609,900
Open House

16512 Greenspring Ave  Lewes, DE 19958

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,400
    Sq. Ft.
Listed by Debbie Riley Geist (302) 507-6257
34185 Skyflower Loop, Lewes, DE 19958 - Photo 1 Price Reduced
-$15,000 (-2.78%)
$525,000

34185 Skyflower Loop  Lewes, DE 19958

  • Single Family
  • Active
  • Updated 2 days ago
  • 5
    Beds
  • 4
    Total Baths
  • 2,814
    Sq. Ft.
Listed by Northrop Realty, FRANCIS ESPARZA
412 Kings Hwy, Lewes, DE 19958 - Photo 1 Price Reduced
-$101,000 (-7.48%)
$1,249,000

412 Kings Hwy  Lewes, DE 19958

  • Single Family
  • Active
  • Updated 23 hours ago
  • 4
    Beds
  • 3
    Total Baths
  • 1,909
    Sq. Ft.
Listed by Monument Sotheby's International Realty, Brian K Barrows and Monument Sotheby's International Realty, JENNIFER BARROWS
21006 Jenny Ct, Lewes, DE 19958 - Photo 1 Price Reduced
-$10,000 (-1.6%)
$614,000

21006 Jenny Ct  Lewes, DE 19958

  • Single Family
  • Active
  • Updated 5 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 2,541
    Sq. Ft.
Listed by ReMax Coastal, SUZANNE MACNAB

Recent Sales near 18037 Highwood Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

3 Good Hope Ct, Rehoboth Beach, DE 19971 - Photo 1 Sold
$1,325,000

3 Good Hope Ct  Rehoboth Beach, DE 19971

  • Single Family
  • Closed
  • 5
    Beds
  • 4
    Total Baths
  • 1,223
    Sq. Ft.
Listed by RE/MAX Realty Group Rehoboth, ROB BURTON
Sold by Coldwell Banker Premier - Rehoboth, KATHY NEWCOMB
21309 High Plns Rd, Lewes, DE 19958 - Photo 1 Sold
$1,167,405

21309 High Plns Rd  Lewes, DE 19958

  • Single Family
  • Closed
  • 5
    Beds
  • 5
    Total Baths
  • 4,664
    Sq. Ft.
Listed by Jack Lingo - Lewes, PAUL TOWNSEND
Sold by Redfin Corporation, Kelley J Johnson
23608 Deaver Cir, Lewes, DE 19958 - Photo 1 Sold
$1,125,000

23608 Deaver Cir  Lewes, DE 19958

  • Single Family
  • Closed
  • 5
    Beds
  • 5
    Total Baths
  • 6,694
    Sq. Ft.
Listed by Patterson-Schwartz-Rehoboth, JAMIE COLEMAN and Patterson-Schwartz-Rehoboth, Jessica White Harrison
Sold by Bill Bjorkland
6 Comfort Ct, Rehoboth Beach, DE 19971 - Photo 1 Sold
$1,425,000

6 Comfort Ct  Rehoboth Beach, DE 19971

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 4,500
    Sq. Ft.
Listed by Jack Lingo - Lewes, Chelsea Bristow
Sold by Jack Lingo - Rehoboth, TJARK BATEMAN

18037 Highwood Drive, Rehoboth Beach, DE 19971 (MLS# DESU2120312) is a Single Family property with 4 bedrooms and 4 full bathrooms. 18037 Highwood Drive is currently listed for $1,299,999 and was received on September 10, 2026. Want to learn more about 18037 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.

Tour this property