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For sale
  • Price cut: $10K (8/3)
    $569,900

    529 Contemplation Way, Middletown, DE 19709

    3beds
    2,375sqft
    : 
    $3,833/mo
    Get pre-qualified
    Single Family Residence
    Built in 2021
    8,276 Square Feet Lot
    $558,900 Zestimate®
    $240/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.
    40 days
    |
    718
    |
    19
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Mr. 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: $240/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

        Estimated market value

        $558,900

        $531,000 - $587,000

        $3,130/mo

        Price history

        DateEventPrice
        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-- $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

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 19709

        Getting around

        2 / 100
        Car-Dependent
        0 / 100
        No Nearby Transit
        31 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Cedar Lane
        • Middle: Alfred G Waters
        • High: Middletown
        • District: Appoquinimink

        Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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