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!
Sold for $1,330,000
$1,330,000
33437 Islander Dr, Millsboro, DE 19966
4beds
3,651sqft
Single Family Residence
Built in 2016
0.26 Acres Lot
$1,321,100 Zestimate®
$364/sqft
$3,661 Estimated rent
Home value
$1,321,100
$1.23M - $1.43M
$3,661/mo
Zestimate® history
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Private officeGas fireplaceFloor-to-ceiling stone fireplaceGreat roomCustom built-insPolished eleganceSophisticated detail
Zillow last checked:
Listing updated:
Listed by:
Judith Dourgarian 908-625-4343,
Northrop Realty
Bought with:
Lee Ann Wilkinson, RA-0002064
Berkshire Hathaway HomeServices PenFed Realty
Source: Bright MLS,MLS#: DESU2091104
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
- Main level bathrooms: 4
- Main level bedrooms: 3
Rooms
- Room types: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Foyer, Laundry, Loft, Office, Storage Room
Primary bedroom
- Features: Crown Molding, Walk-In Closet(s), Flooring - HardWood, Window Treatments, Ceiling Fan(s)
- Level: Main
- Area: 357 Square Feet
- Dimensions: 17 X 21
Bedroom 2
- Features: Ceiling Fan(s), Flooring - Carpet, Window Treatments
- Level: Main
- Area: 156 Square Feet
- Dimensions: 12 X 13
Bedroom 3
- Features: Cathedral/Vaulted Ceiling, Ceiling Fan(s), Flooring - Carpet, Window Treatments
- Level: Main
- Area: 168 Square Feet
- Dimensions: 12 X 14
Bedroom 4
- Features: Ceiling Fan(s), Walk-In Closet(s), Flooring - Carpet, Window Treatments
- Level: Upper
- Area: 154 Square Feet
- Dimensions: 11 X 14
Dining room
- Features: Cathedral/Vaulted Ceiling, Flooring - HardWood, Window Treatments
- Level: Main
- Area: 276 Square Feet
- Dimensions: 12 X 23
Foyer
- Features: Crown Molding, Chair Rail, Flooring - HardWood
- Level: Main
- Area: 133 Square Feet
- Dimensions: 7 X 19
Kitchen
- Features: Kitchen Island, Breakfast Bar, Granite Counters, Cathedral/Vaulted Ceiling, Kitchen - Gas Cooking, Pantry, Flooring - HardWood
- Level: Main
- Area: 288 Square Feet
- Dimensions: 16 X 18
Laundry
- Features: Built-in Features, Flooring - Tile/Brick
- Level: Main
- Area: 100 Square Feet
- Dimensions: 10 X 10
Living room
- Features: Fireplace - Gas, Cathedral/Vaulted Ceiling, Built-in Features, Flooring - HardWood, Window Treatments
- Level: Main
- Area: 588 Square Feet
- Dimensions: 21 X 28
Loft
- Features: Flooring - HardWood, Window Treatments
- Level: Upper
- Area: 437 Square Feet
- Dimensions: 19 X 23
Mud room
- Features: Built-in Features, Flooring - Tile/Brick
- Level: Main
- Area: 112 Square Feet
- Dimensions: 7 X 16
Office
- Features: Chair Rail, Flooring - HardWood, Window Treatments
- Level: Main
- Area: 168 Square Feet
- Dimensions: 12 X 14
Storage room
- Features: Flooring - Other
- Level: Upper
- Area: 275 Square Feet
- Dimensions: 11 X 25
Heating
- Forced Air, Heat Pump, Central, Ceiling, Natural Gas
Cooling
- Ceiling Fan(s), Central Air, Programmable Thermostat, Electric
Appliances
- Included: Microwave, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Double Oven, Self Cleaning Oven, Oven, Range Hood, Refrigerator, Stainless Steel Appliance(s), Washer, Tankless Water Heater
- Laundry: Main Level, Laundry Room, Mud Room
Features
- Built-in Features, Ceiling Fan(s), Combination Dining/Living, Combination Kitchen/Dining, Combination Kitchen/Living, Dining Area, Entry Level Bedroom, Open Floorplan, Kitchen - Gourmet, Kitchen Island, Pantry, Primary Bath(s), Recessed Lighting, Upgraded Countertops, Walk-In Closet(s), Central Vacuum, Other, 2 Story Ceilings, 9'+ Ceilings, Dry Wall, High Ceilings, Tray Ceiling(s)
- Flooring: Ceramic Tile, Carpet, Engineered Wood, Wood
- Doors: Six Panel
- Has basement: No
- Number of fireplaces: 3
- Fireplace features: Gas/Propane, Mantel(s), Stone, Other
Interior area
- Total structure area: 3,651
- Total interior livable area: 3,651 sqft
- Finished area above ground: 3,651
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Garage Faces Front, Garage Door Opener, Oversized, Inside Entrance, Concrete, Attached, Driveway
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: Doors - Lever Handle(s), Doors - Swing In
Features
- Levels: Two
- Stories: 2
- Patio & porch: Patio
- Exterior features: Bump-outs, Extensive Hardscape, Lighting, Street Lights, Underground Lawn Sprinkler, Other
- Pool features: Community
- Spa features: Community
- Has view: Yes
- View description: Garden, Golf Course, Panoramic, Pond
- Has water view: Yes
- Water view: Pond
Lot
- Size: 0.26 Acres
- Dimensions: 80.00 x 142.00
- Features: Backs - Open Common Area, Front Yard, Landscaped, Rear Yard, SideYard(s)
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 23430.00170.00
- Zoning: MR
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Coastal,Colonial,Contemporary
- Property subtype: Single Family Residence
Materials
- Cement Siding
- Foundation: Crawl Space
- Roof: Architectural Shingle,Metal,Pitched
Condition
- Excellent
- New construction: No
- Year built: 2016
Details
- Builder model: Cassidy-Expanded
- Builder name: Schell
Utilities & green energy
- Electric: 200+ Amp Service, Circuit Breakers
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: Pool
- Security: Carbon Monoxide Detector(s), Security System, Smoke Detector(s)
- Subdivision: Peninsula
HOA
- Has HOA: Yes
- Amenities included: Bar/Lounge, Basketball Court, Beach Access, Bike Trail, Billiard Room, Cable TV, Clubhouse, Common Grounds, Community Center, Dining Rooms, Dog Park, Fitness Center, Game Room, Gated, Golf Club, Golf Course, Golf Course Membership Available, Spa/Hot Tub, Jogging Path, Meeting Room, Party Room, Picnic Area, Pier/Dock, Indoor Pool, Pool, Putting Green, Recreation Facilities, Sauna, Security, Tennis Court(s), Tot Lots/Playground, Other
- Services included: Cable TV, Common Area Maintenance, Health Club, Internet, Maintenance Grounds, Pool(s), Recreation Facility, Road Maintenance, Security, Snow Removal, Trash
- HOA fee: $1,153 quarterly
- HOA name: LEGUM NORMAN
Location
- Region: Millsboro
Financial & listing details
- Price per square foot: $364/sqft
- Tax assessed value: $777,400
- Annual tax amount: $1,684
- Date on market: 8/7/2025
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional
- Exclusions: Garage Refrigerator -ask Listing Agent
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 1/15/2026 | Sold | $1,330,000-8.3%$364/sqft |
Source:  Bright MLS #DESU2091104 Report a problem | ||
| 11/16/2025 | Contingent | $1,450,000$397/sqft |
Source: Bright MLS #DESU2091104 Report a problem | ||
| 8/7/2025 | Listed for sale | $1,450,000+52.6%$397/sqft |
Source: Bright MLS #DESU2091104 Report a problem | ||
| 9/28/2021 | Sold | $950,000-38.8%$260/sqft |
Source: Bright MLS #DESU2002722 Report a problem | ||
| 6/2/2017 | Sold | $1,551,667+812.7%$425/sqft |
Source: Public Record Report a problem | ||
| 12/22/2016 | Sold | $170,000$47/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $1,685 -26.2% | $388,700 +611.9% |
| 2024 | $2,282 +0.1% | $54,600 |
| 2023 | $2,279 +1.6% | $54,600 |
| 2022 | $2,243 +4.2% | $54,600 |
| 2021 | $2,152 +4.8% | $54,600 |
| 2020 | $2,054 | $54,600 |
| 2019 | $2,054 +0.4% | $54,600 |
| 2018 | $2,045 -1% | $54,600 |
| 2017 | $2,064 +1128.9% | $54,600 +992% |
| 2016 | $168 -3% | $5,000 |
| 2015 | $173 +1.5% | $5,000 |
| 2014 | $171 -1.1% | $5,000 |
| 2013 | $172 +4% | $5,000 |
| 2012 | $166 +1% | $5,000 |
| 2011 | $164 | $5,000 |
| 2010 | $164 +0.4% | $5,000 |
| 2009 | $163 | $5,000 |
| 2008 | -- | -- |
| 2007 | -- | -- |
| 2006 | -- | -- |
| 2005 | -- | -- |
| 2004 | -- | -- |
Find assessor info on the county website
Neighborhood: 19966
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Nearby schools
GreatSchools rating
- 5/10Long Neck Elementary SchoolGrades: K-5Distance: 1.6 mi
- 4/10Millsboro Middle SchoolGrades: 6-8Distance: 6.5 mi
- 3/10Sussex Central High SchoolGrades: 9-12Distance: 8.5 mi
Schools provided by the listing agent
- High: Sussex Central
- District: Indian River
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Delaware
- Sussex County
- Millsboro
- 19966
- 33437 Islander Dr
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