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529 Contemplation Way, Middletown, DE, 19709

3beds
3baths
2,375sqft
$569,900
$240price/sqft
$3,615/moest. monthly cost
$144,600/yrincome needed

About This Home

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.

Getting Around

2
WalkingCar-Dependent
0
TransitNo Nearby Transit
31
BikeSomewhat Bikeable

Schools

9/10
9/10
Middletown High SchoolGrades 9-123.6 mi

Construction

Condition

  • Property condition: Excellent
  • Year built: 2021

Materials

  • Foundation: Concrete Perimeter
  • Roof: Asphalt
  • Construction materials: Vinyl Siding

Type & Style

  • Home type: SingleFamily
  • Architectural style: Carriage House
  • Property subType: Single Family Residence

Interior

Appliances

  • Appliances included: Microwave,Built-In Range,Dishwasher,Stainless Steel Appliance(s),Electric Water Heater
  • Laundry features: Main Level

Basement

  • Has basement: Yes
  • Basement: Full

Bedroom2

  • Level: Upper

Bedroom3

  • Level: Upper

Bedroom4

  • Level: Upper

Bedrooms & Bathrooms

  • Bedrooms: 3
  • Bathrooms: 3
  • Full bathrooms: 2
  • 1/2 bathrooms: 1
  • Main level bathrooms: 2
  • Main level bedrooms: 1

Dining Room

  • Level: Main

Family Room

  • Level: Main

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
  • Finished area below ground: 0
  • Finished area above ground: 2,375

Heating & Cooling

  • Heating features: Forced Air,Natural Gas
  • Cooling features: Central Air,Natural Gas

Interior Area

  • Total structure area: 2,375
  • Total interior livable area: 2,375 sqft

Kitchen

  • Level: Main

Loft

  • Level: Upper

Office

  • Level: Main

Primary Bathroom

  • Level: Main

Primary Bedroom

  • Level: Main

Property

Accessibility

  • Accessibility features: None

Details

  • Parcel number: 13012.24039
  • Zoning: S
  • Special condition: Standard
  • Exclusions: All Personal Property

Features

  • Levels: Two
  • Stories: 2
  • Pool features: Community
  • Patio & porch: Patio,Porch

Lot

  • Lot size: 8,276 sqft
  • Lot size dimensions: 0.00 x 0.00

Parking

  • Total spaces: 2
  • Parking features: Garage Faces Front,Attached
  • Has garage: Yes
  • Attached garage spaces: 2
  • Covered spaces: 2

Climate Risk is Financial Risk

Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.

Biggest Threats for This Home

  • Inland Flooding
    Inland FloodingRelatively High
  • Winter Weather
    Winter WeatherRelatively High
  • Cold Wave
    Cold WaveModerate
  • Drought
    DroughtModerate
  • Heat Wave
    Heat WaveModerate
  • Tsunami
    TsunamiInsufficient Data

How This Home’s Risks Compare

Inland Flooding
Winter Weather
Cold Wave
Drought
Heat Wave
Tsunami

FEMA Declared Disasters Across Delaware Counties

Understanding the Costs

Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.

Estimated Costs Today

MonthlyAnnual
Mortgage $2,881$34,572
Home Insurance *$131$1,572
Property Taxes $341$4,092
Electricity $262$3,151
Total$3,615$43,380
*Does not include cost of any FAIR Plan premiums

Income You'd Need if You Spent...

35% on housing$123,942/yr
40% on housing$108,450/yr
45% on housing$96,400/yr

Delaware FAIR Plan Programs

Insurance Placement Facility of Delaware

Covered
WildfireWildfire
Add-on available
HailHail
WindWind
Visit Website →
Current Policies
Residential: 1,170Commercial: 57
Total Premiums$607,000
Total Exposure$249.53M

How Costs Could Change Over Time

Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.

Insurance Growth Rate5-year average: 7.0%
7.0%
0%30.0%
Electricity Growth Rate10-year average: 8.7%
8.7%
0%15.0%
Property Taxes Growth Rate2-year average: -0.8%
-0.8%
0%15.0%
Income Spent on Housing
30%
30%45%

Comparing Against the Market

Price Per Sq Ft

$240This listing

vs Other Active Listings

Avg $/sqft

ZIP 19709$200
New Castle County$172

vs Homes Sold Last Month

Median $/sqft

ZIP 19709$195
New Castle County$218

Current Market Trends

Median Price Per Square Foot

The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.

Historicals for This Listing

Zestimate History ($/sqft)

Price History

DateEventPrice
2026-08-03Price change$569,900
2026-07-09Listed for sale$579,900
2021-05-27Sold$427,507

For Sale by Agent

AgentMr. Earl Endrich
BrokerageBHHS Fox & Roach - Hockessin

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