Middletown, DE 19709 529 Contemplation Way
$579,900
OPEN HOUSE Sat, Jul 18 2026 10:00 AM - 12:00 PM



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Presented By: BHHS Fox & Roach - Hockessin
Home Details
Welcome to 529 Contemplation Way, an exceptional home located in the highly sought-after Whispering Woods 55+ active adult community in Middletown, Delaware, where luxury, convenience, and a carefree lifestyle come together. Designed for buyers seeking the ease of first-floor living without sacrificing space, this beautifully maintained home offers the perfect blend of elegance, flexibility, and low-maintenance living. Outstanding curb appeal, a welcoming covered front porch, and manicured landscaping create an inviting first impression, while the dramatic two-story foyer and rich hardwood flooring throughout most of the main level immediately showcase the home's quality craftsmanship. The open-concept floor plan is filled with abundant natural light and soaring vaulted ceilings, creating a bright, spacious atmosphere ideal for everyday living and entertaining. The expansive family room flows seamlessly into the dining area before opening to the screened porch and oversized stamped concrete patio, providing exceptional indoor-outdoor living for morning coffee, relaxing evenings, or entertaining family and friends. The beautifully appointed kitchen is the centerpiece of the home, featuring stainless steel appliances, designer countertops, a stylish tile backsplash, abundant cabinetry, hardwood flooring, an undermount sink with a gooseneck faucet, and a large center island with seating and additional storage. Just beyond, the sun-filled breakfast area with its vaulted ceiling offers the perfect place to begin each day. The spacious main-level primary suite provides the comfort today's buyers desire with a tray ceiling, generous closet space, and a private bath featuring a double vanity and walk-in shower. A dedicated first-floor office offers flexibility for working from home, hobbies, crafts, or a quiet reading room, while the convenient first-floor laundry room and powder room complete the thoughtfully designed main level. Upstairs, you'll discover three additional spacious rooms along with an open loft overlooking the main living area, creating the perfect second family room, media room, game room, or private retreat for overnight guests and visiting family. Whether you're hosting holidays or simply need additional living space, this versatile layout adapts beautifully to your lifestyle. The expansive unfinished basement provides exceptional storage and endless possibilities for future finished living space, including a recreation room, fitness studio, workshop, hobby room, or home theater. Beyond the home itself, Whispering Woods offers one of Middletown's premier active adult lifestyles, featuring a beautifully appointed clubhouse, fitness center, outdoor swimming pool, gathering spaces, and an active social calendar filled with clubs, activities, and community events. Lawn care and snow removal are included, allowing homeowners more time to travel, relax, and enjoy everything the community has to offer. Ideally located just minutes from Historic Downtown Middletown, residents enjoy convenient access to outstanding restaurants, boutique shopping, coffee shops, grocery stores, healthcare, parks, walking trails, golf courses, and major commuter routes including Route 1, while remaining within easy reach of Delaware's beaches, Wilmington, and Philadelphia. Combining timeless architecture, an open and flexible floor plan, abundant natural light, outstanding indoor and outdoor living spaces, resort-style community amenities, and the convenience of move-in-ready first-floor living, 529 Contemplation Way presents a rare opportunity to enjoy the lifestyle you've been waiting for in one of Middletown's most desirable 55+ communities.
Presented By: BHHS Fox & Roach - Hockessin
Interior Features for 529 Contemplation Way
Bedrooms
Bedrooms Count All Upper Levels3
Bedrooms Count Upper Level 13
Main Level Bedrooms1
Total Bedrooms4
Bathrooms
Bathrooms Half Upper Level 10
Bathrooms Half Main Level1
Bathrooms Half All Upper Levels0
Bathrooms Full Upper Level 11
Bathrooms Full All Upper Levels1
Bathrooms Count Upper Level 11.00
Bathrooms Count All Upper Levels1
Half Baths1
Total Baths3
Other Interior Features
LivingAreaSourceAssessor
Below Grade Unfin Area UnitsSquare Feet
Below Grade Unfin SQFT0
Below Grade Unfin SQFT SourceAssessor
Above Grade Finished Area2375
Above Grade Finished Area SourceAssessor
Above Grade Finished Area Unit TypeSquare Feet
BasementFull
Basement (Y/N)Yes
Below Grade Finished Area0
Below Grade Finished Area SourceAssessor
Below Grade Finished Area Unit TypeSquare Feet
Central Air Y/NYes
Fireplace Y/NNo
FlooringHardwood
Heating FuelNatural Gas
Heating Y/NYes
Hot WaterElectric
Interior AmenitiesBathroom - Soaking Tub, Bathroom - Walk-In Shower, Breakfast Area, Combination Dining/Living, Dining Area, Curved Staircase, Entry Level Bedroom, Floor Plan - Open, Kitchen - Eat-In, Kitchen - Gourmet, Kitchen
Laundry TypeMain Floor
Other Rooms
Room TypeDining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Loft, Office, Primary Bathroom
Room Details for 529 Contemplation Way
Bedroom 2
level
Upper 1
Bedroom 3
level
Upper 1
Bedroom 4
level
Upper 1
Dining Room
level
Main
Family Room
level
Main
Kitchen
level
Main
Loft
level
Upper 1
Office
level
Main
Primary Bathroom
level
Main
Primary Bedroom
level
Main
General for 529 Contemplation Way
Acceptable FinancingCash, Conventional, FHA, VA
AccessibilityNone
AppliancesBuilt-In Microwave, Built-In Range, Dishwasher, Stainless Steel Appliances
Architectural StyleCape Cod
Assoc Fee Paid PerMonthly
Bathrooms Count Main Level2.00
Bathrooms Full Main Level1
CityMIDDLETOWN
Community Pool FeaturesIn Ground
Condo/Coop Association fee Y/NNo
Construction MaterialsVinyl Siding
Cool FuelNatural Gas
CoolingCentral A/C
CountyNEW CASTLE
DirectionsFrom DE-896 (Summit Bridge Road), turn onto Whispering Woods Road. Turn right to stay on Whispering Woods Road, then turn left onto Contemplation Way. The home will be on your left.
DisclosuresLead Based Paint - State, Prop Disclosure, Radon
ExclusionsAll Personal Property
Full Baths2
Garage Spaces2.00
Garage Y/NYes
HOAYes
HOA Fee$315.00
HeatingForced Air
Legal SubdivisionWHISPERING WOODS
Levels2
Living Area2375
Lot Size Square Feet8276.00
Lot Size UnitsSquare Feet
MLS AreaSouth Of The Canal (30907)
New ConstructionNo
Other StructuresAbove Grade, Below Grade
OwnershipFee Simple
Patio/Porch FeaturesPatio(s), Porch(es)
PossessionNegotiable
Price Per Sq Ft Total AG244.17
Property ConditionExcellent
Property TypeResidential
RoofAsphalt
School DistrictAPPOQUINIMINK
Senior Community Age Req55
Senior Community Y/NYes
SewerPublic Sewer
Standard StatusActive
StatusACTIVE
Structure TypeDetached
Subdivision NameWHISPERING WOODS
Tax Annual Amount4538.0
Tax Assessed Value519600.0
Tax Lot039
Tax Year2025
Total SQFT2375
Vacation Rental Y/NNo
Water Access Y/NNo
Year Built2021
Year Built SourceAssessor
ZoningS
Exterior for 529 Contemplation Way
# of Attached Garage Spaces2
Foundation DetailsOther
Garage FeaturesGarage - Front Entry
Land Assessed Value113600.00
Lot Dimensions0.00 x 0.00
Lot Size Acres0.19
Lot Size SourceAssessor
LotDimensionsSourceAssessor
Navigable Water Y/NNo
PoolYes - Community
Total Parking Spaces2
Type of ParkingAttached Garage
Water Oriented Y/NNo
Water SourcePublic
Water View Y/NNo
Waterfront Y/NNo
Additional Details
Price History
Schools
High School
Middletown High School
Elementary School
Cedar Lane Elementary School
Middle School
Alfred G Waters Middle School
Jeremy Scott Wilson
Real Estate Agent
SQFT • 2,375