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$1,330,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 3,651 Sq. Ft.
  • 2 Car Garage
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The welcoming covered entry of 33437 Islander Drive invites you inside to explore this exceptional luxury home, designed with enduring vision for resort-style living at home. Nestled in the sought-after, amenity-rich community of The Peninsula on Indian River Bay, this expanded Cassidy model balances coastal style, colonial design cues, and contemporary flair. Every room of this residence reflects polished elegance, sophisticated detail, and thoughtful upgrades that make it truly one-of-a-kind. Step inside and you are greeted with exquisite design elements, gorgeous hardwood flooring, feature lighting, detailed architectural moldings, and an open floor plan that unfolds beautifully from one space to the next. The great room makes a stunning first impression with its two-story ceiling, floor-to-ceiling stone fireplace flanked by custom built-ins, and a wall of stacked picture windows topped by transoms, filling the space with natural light and framing views of the expanded courtyard, outdoor kitchen, and gardens. The gourmet kitchen is as functional as it is beautiful, featuring stainless steel appliances with range hood, Quartz countertops, gray glass subway tile backsplash, crisp-white 42" custom cabinetry, and an oversized L-shaped peninsula with breakfast bar. A thoughtfully redesigned walk-in pantry with custom birch shelving, a dry bar area in the dining nook, and abundant storage throughout the home reflect the owners' eye for both form and function. The adjacent dining area offers spectacular views of the outdoors, creating the perfect setting for celebratory meals. Everyday conveniences are elevated with a custom laundry room outfitted with a sink, cabinetry, folding station, and concealed hampers, along with a professionally redesigned mudroom that accommodates golf bags and sports equipment. The oversized garage has been enhanced with slat walls, a bank of cabinets, and countertops for organized storage. The first-floor primary suite is a serene retreat, appointed with a tray ceiling, a shiplap-accented wall, wrap-around windows, private patio access, and two of the largest closets found in The Peninsula, redesigned with upgraded shelving and storage systems. The spa-like ensuite boasts dual vanities, a glass-enclosed shower with bench and transom window, and a private water closet. Two additional first-floor guest bedrooms, one with an ensuite bath, and one with a dedicated full bathroom, provide comfort and convenience for visiting family or older guests. A private office with bump-out window and a powder room completes the main level. Upstairs, a loft offers a relaxing retreat for reading, puzzles, or quiet leisure, alongside a spacious bedroom and dual access bath. A large unfinished "attic" storage room provides exceptional space rarely found in homes of this design and offers endless possibilities. The exterior living spaces are equally captivating. The terraced courtyard has been expanded to include a firepit area, an outdoor kitchen with granite bar seating, built-in refrigerator, grill, griddle, and trash system, plus a cozy gas fireplace, creating a private resort-style setting for entertaining or unwinding. Additional touches include wallpaper accents in the powder room, primary bath, and front bath; painted closets and pantry interiors; and shiplap details in the loft and laundry room. Beyond the home itself, the location within The Peninsula's, centrally located, exceptional Lakeside neighborhood enhances its appeal. Larger lot sizes provide a more open, less congested feel, and Islander Drive ends in a quiet cul-de-sac with limited traffic. Life here offers not only this remarkable residence but also access to the Peninsula's world-class amenities-Jack Nicklaus Signature Golf, pools, sports facilities, bayfront beach, and endless opportunities to live your best coastal life. Why wait to build when this thoughtfully designed, move-in-ready home is available now!

Full Property Details for 33437 Islander Dr

General

  • Sold For: $1,330,000
  • HOA FEE: $384/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $1,684 (2025)
  • Status: Closed
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: DESU2091104
  • Added to Site: 197 day(s) ago

Interior

  • Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Foyer, Laundry, Loft, Mud Room, Office, Storage Room
  • Interior Features: Built-Ins, Carpet, Ceiling Fan(s), Combination Dining/Living, Combination Kitchen/Dining, Combination Kitchen/Living, Dining Area, Entry Level Bedroom, Floor Plan - Open, Kitchen - Gourmet, Kitchen - Island, Pantry, Primary Bath(s), Recessed Lighting, Upgraded Countertops, Walk-in Closet(s), Wood Floors, Central Vacuum, Other
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Fireplace(s): Gas/Propane, Mantel(s), Stone, Other
  • Appliances: Built-In Microwave, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Oven - Double, Oven - Self Cleaning, Oven - Wall, Range Hood, Refrigerator, Stainless Steel Appliances, Washer, Water Heater - Tankless
  • Flooring: Ceramic Tile, Partially Carpeted, Engineered Wood

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Upper Floor Baths: 1
  • Upper - Full Baths: 1
  • Main Floor Baths: 4
  • Main - Full Baths: 3
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 4
  • Bedrooms Upper: 1
  • Bedrooms Main & Up: 3

Other Rooms

  • Laundry: Main Floor

Additional Information

  • Shared Amenities: Bar/Lounge, Basketball Courts, Beach, Bike Trail, Billiard Room, Cable, Club House, Common Grounds, Community Center, Dining Rooms, Dog Park, Exercise Room, Fitness Center, Game Room, Gated Community, Golf Club, Golf Course, Golf Course Membership Available, Hot tub, Jog/Walk Path, Meeting Room, Party Room, Picnic Area, Pier/Dock, Pool - Indoor, Pool - Outdoor, Putting Green, Recreational Center, Sauna, Security, Spa, Swimming Pool, Tennis Courts, Tot Lots/Playground, Other
  • Shared Pool: Yes
  • Pool: Yes
  • Security/Safety: Carbon Monoxide Detector(s), Security System, Smoke Detector

Exterior

  • Exterior Features: Bump-outs, Extensive Hardscape, Exterior Lighting, Street Lights, Underground Lawn Sprinkler, Other
  • Porch/Patio/Deck: Patio(s)

Parking

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

Location

  • Area: Indian River Hundred (31008)
  • County: SUSSEX
  • Subdivision: PENINSULA
  • Driving Directions: Route 24 to Bay Farm Road. Straight Ahead to Main entrance of The Peninsula. Stay Left to GUEST side at Security Gate House. You must be registered to enter. Contact Listing Agent.
  • Direction Faces: East

School Information

  • School District: Indian River
  • High School: Sussex Central

Community

  • Association: Yes
  • Assoc. Name: LEGUM NORMAN
  • Assoc. Fees Include: Cable TV, Common Area Maintenance, Health Club, High Speed Internet, Lawn Maintenance, Pool(s), Recreation Facility, Road Maintenance, Security Gate, Snow Removal, Trash
  • Pets Allowed: Yes
  • Pets: Case by Case Basis

Heating & Cooling

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

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Coastal, Colonial, Contemporary
  • Structure Type: Detached
  • Builder: Schell
  • Model: Cassidy-Expanded
  • Construction: Cement Siding
  • Foundation: Crawl Space
  • Roof: Architectural Shingle, Metal, Pitched
  • Walls/Ceilings: 2 Story Ceilings, 9'+ Ceilings, Dry Wall, High, Tray C
  • Doors: Six Panel
  • Stories Description: Main, Upper 1
  • Square Feet: 3,651
  • Sq. Ft. Source: Estimated
  • Living Area: 3,651 Sq. Ft.
  • Finished Above Grnd: 3,651 Sq. Ft.
  • Year Built: 2016
  • Year Built Source: Assessor
  • Property Condition: Excellent

Additional Structures

  • Other Structures: Cabana/Pool House

Lot Features

  • Property View: Garden/Lawn, Golf Course, Panoramic, Pond
  • Lot Size (Acres): 0.26
  • Lot Size (Sq. Ft.): 11,326
  • Lot Size Source: Assessor
  • Lot Dimensions: 80.00 x 142.00
  • Zoning: MR
  • Lot Description: Backs - Open Common Area, Front Yard, Landscaping, Rear Yard, SideYard(s)

Water Features

  • Water View: Yes

Financial Considerations

  • Price Per Sq. Ft.: $397.15
  • Association Fee: $1,153
  • Assoc Fee Freq.: Quarterly
  • School Tax: $1,518
  • County Tax: $166
  • County Tax Freq: Annually
  • Tax Amount: $1,684
  • Tax Year: 2025
  • Terms: Standard Sale
  • Tax Total Finished Sq. Ft.: 1662

Disclosures and Reports

  • Ownership: Fee Simple
  • Exclusions: Garage Refrigerator -Ask Listing Agent
  • Lot Number: 59

Listed by Northrop Realty, Judith Dourgarian
Sold by Berkshire Hathaway HomeServices PenFed Realty, Lee Ann Wilkinson

Listing agent

— 33437 Islander Dr —

  • Judith Dourgarian

    Northrop Realty

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with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 33437 Islander Dr

School District:Indian River School District
NameGradesDistance
Long Neck Elementary School
26064 School Lane, Millsboro, DE 19966
PK-51.7 mi
Millsboro Middle School
302 East State Street, Millsboro, DE 19966
6-86.6 mi
Sussex Central High School, Georgetown, DE
26026 Patriots Way, Georgetown, DE 19947
8-128.6 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 33437 Islander Dr

Date
Details
Price
Change
Source
1/15/2026
Sold
$1,330,000
-8.28%
MLS
8/07/2025
Listed
$1,450,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Northrop Realty, Judith Dourgarian
Sold by Berkshire Hathaway HomeServices PenFed Realty, Lee Ann Wilkinson

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33437 Islander Drive, Millsboro, DE 19966 (MLS# DESU2091104) is a Single Family property that was sold at $1,330,000 on January 15, 2026. Want to learn more about 33437 Islander Drive? Do you have questions about finding other Single Family real estate for sale in Millsboro? You can browse all Millsboro real estate or contact a Coldwell Banker agent to request more information.