- Overview
- Description
- Property Details
- Location
- HOA Management
- Facts & Features
- Getting Around
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Street View
$559,900
Monthly Est:$2,787
3 Beds
- 3 Baths
2 full baths + 1 half bath
2,375sqft
529 Contemplation Way, Middletown, DE 19709
$559,900
$2,787/moEst:
Get Pre-Approved
Single Family Residence
Built in 2021
$315/mo HOA
8,276 sqft lot
$236/sq.ft
Description
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.
- Houzeo last checked: 3 hours ago
- Listing updated: October 7, 2026 at 8:36 pm
- Listing Provided by: Earl Endrich (610) 496-3838 | BHHS Fox & Roach - Hockessin (302) 999-9999
- Source: Bright MLS-NJ | MLS#: DENC2105858

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
2021
HOA Fees
$315/mo
Finished Area
2,375 sqft
Lot Size
8,276 sqft lot
Basement Area
- sqft
MLS Name
Bright MLS
MLS Number
DENC2105858
MLS Status
ACTIVE-BRIGHT
Days on Market
91

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Location
HOA Management
N/A
HOA Fees
$315/ Monthly
Amenities
Amenities and services may be covered by one or multiple associations and service providers.
Ext Bldg Maint
Common Area
Trash Pickup
Snow Removal
Pool
Gym
Club House
Meeting Room
Recreational Center
Bar/Lounge
Recreation Facility
Common Area Maintenance
Pickleball Courts
Lawn Maintenance
Billiard Room
Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 3
Bathrooms: 3
Interior
Interior Features
Bathroom 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 Island, Primary Bath(s), Wood Floors
Cooling
Central A/c
Appliances
Built In Microwave, Built In Range, Dishwasher, Stainless Steel Appliances
Heating
Forced Air
Sewer
Public Sewer
Flooring
Hardwood
Construction
Year Built
Year Built: 2021
Home type
Single Family Residence
Property Condition
Excellent
Architectural Style
Carriage House
Foundation Details
Concrete Perimeter
Roof
Asphalt
Construction Materials
Vinyl Siding
Utilities & Energy
Association Amenities
Bar/lounge, Billiard Room, Club House, Common Grounds, Community Center, Fitness Center, Recreational Center, Pickleball Courts, Meeting Room
Basement
Full
Water Source
Public
Other Features
Subdivision Name
Whispering Woods
Patio And Porch Features
Patio, Porch
Price History
| Date | Event | Price |
|---|---|---|
10/02/2026 Source: | Price Decreased | $559,900 -1.75% $236/sqft |
08/03/2026 Source: | Price Decreased | $569,900 -1.72% $240/sqft |
07/09/2026 Source: | Listed for Sale | $579,900 $244/sqft |
Nearby Homes
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Based on information from Bright MLS through Oct 29, 2026, 02:15PM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information
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