529 Contemplation Way, Middletown, DE 19709
What's special
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.
- 91 days
- 685
- 33
Travel times
Family Room
Kitchen
Primary Bedroom
Zillow last checked:
Listing updated:
Earl Endrich 610-496-3838,
BHHS Fox & Roach - Hockessin (302) 999-9999,
Listing Team: Team Endrich
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
- Main level bathrooms: 2
- Main level bedrooms: 1
Rooms
- Room types: Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Loft, Office, Primary Bathroom
Primary bedroom
- Level: Main
Bedroom 2
- Level: Upper
Bedroom 3
- Level: Upper
Bedroom 4
- Level: Upper
Primary bathroom
- Level: Main
Dining room
- Level: Main
Family room
- Level: Main
Kitchen
- Level: Main
Loft
- Level: Upper
Office
- Level: Main
Heating
- Forced Air, Natural Gas
Cooling
- Central Air, Natural Gas
Appliances
- Included: Microwave, Built-In Range, Dishwasher, Stainless Steel Appliance(s), Electric Water Heater
- Laundry: Main Level
Features
- Soaking Tub, Bathroom - Walk-In Shower, Breakfast Area, Combination Dining/Living, Dining Area, Curved Staircase, Entry Level Bedroom, Open Floorplan, Eat-in Kitchen, Kitchen - Gourmet, Kitchen Island, Primary Bath(s), 9'+ Ceilings
- Flooring: Hardwood, Wood
- Basement: Full
- Has fireplace: No
Interior area
- Total structure area: 2,375
- Total interior livable area: 2,375 sqft
- Finished area above ground: 2,375
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Garage Faces Front, Attached
- Attached garage spaces: 2
Accessibility
- Accessibility features: None
Features
- Levels: Two
- Stories: 2
- Patio & porch: Patio, Porch
- Pool features: Community
Lot
- Size: 8,276 Square Feet
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 13012.24039
- Zoning: S
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Carriage House
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- Excellent
- New construction: No
- Year built: 2021
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: Pool
- Senior community: Yes
- Subdivision: Whispering Woods
HOA
- Has HOA: Yes
- Amenities included: Bar/Lounge, Billiard Room, Clubhouse, Common Grounds, Community Center, Fitness Center, Recreation Facilities, Meeting Room
- Services included: Common Area Maintenance, Maintenance Grounds, Pool(s), Recreation Facility, Snow Removal, Trash, Maintenance Structure
- HOA fee: $315 monthly
Location
- Region: Middletown
Financial & listing details
- Price per square foot: $236/sqft
- Tax assessed value: $519,600
- Annual tax amount: $4,538
- Date on market: 7/9/2026
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional,FHA,VA Loan
- Exclusions: All Personal Property
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 10/2/2026 | Price change | $559,900-1.8%$236/sqft |
Source: | ||
| 8/3/2026 | Price change | $569,900-1.7%$240/sqft |
Source: | ||
| 7/9/2026 | Listed for sale | $579,900+35.6%$244/sqft |
Source: | ||
| 5/27/2021 | Sold | $427,507$180/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,538 +10.3% | $519,600 +446.4% |
| 2024 | $4,116 +16.6% | $95,100 |
| 2023 | $3,530 +2% | $95,100 +1.9% |
| 2022 | $3,461 +1678.7% | $93,300 +1596.4% |
| 2021 | $195 +1.2% | $5,500 |
| 2020 | $192 +8% | $5,500 |
| 2019 | $178 | $5,500 |
| 2017 | -- | $5,500 |
Monthly payment
Estimated market value
$547,900
$521,000 - $575,000
$3,134/mo
Climate risks
Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.