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Open: Sat 1pm-2:30pm
For salePrice cut: $10K (10/2)
$559,900
3beds
2,375sqft

529 Contemplation Way, Middletown, DE 19709

3beds
2,375sqft
Single Family Residence
Built in 2021
8,276 Square Feet Lot
$547,900 Zestimate®
$236/sqft
$315/mo HOA

What's special

Outdoor swimming poolManicured landscapingDesigner countertopsSoaring vaulted ceilingsAbundant natural lightStainless steel appliancesSpacious main-level primary suite

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
Source: Bright MLS,MLS#: DENC2105858MLS Logo
Travel times

Family Room

Kitchen

Primary Bedroom

Zillow last checked:

Listing updated:

Listed by:

Earl Endrich 610-496-3838,

BHHS Fox & Roach - Hockessin (302) 999-9999,

Listing Team: Team Endrich

Source: Bright MLS,MLS#: DENC2105858MLS Logo

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

DateEventPrice
10/2/2026Price change$559,900-1.8%$236/sqft
Source: Bright MLS #DENC2105858 Report a problem
8/3/2026Price change$569,900-1.7%$240/sqft
Source: Bright MLS #DENC2105858 Report a problem
7/9/2026Listed for sale$579,900+35.6%$244/sqft
Source: Bright MLS #DENC2105858 Report a problem
5/27/2021Sold$427,507$180/sqft
Source: Public Record Report a problem

Public tax history

YearProperty taxesTax 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
Find assessor info on the county website

Monthly payment

Est. payment
$3,776/mo
Principal & interest
$3144
Property taxes
$317
HOA Fees
$315
More affordability toolsChevron Right

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®️.

Neighborhood: 19709

Nearby schools

Cedar Lane Elementary School
Grades 1-5 • 0.6 miles
9/10
GreatSchools® Rating
Test Score Rating
10/10
Student Progress Rating
7/10
Waters (Alfred G.) Middle School
Grades 6-8 • 0.6 miles
8/10
GreatSchools® Rating
Test Score Rating
10/10
Student Progress Rating
7/10
Middletown High School
Grades 9-12 • 3.6 miles
9/10
GreatSchools® Rating
College Readiness Rating
8/10

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