529 Contemplation Way, Middletown, DE 19709
Local realty services provided by:ERA Byrne Realty
529 Contemplation Way,Middletown, DE 19709
$569,900
- 3 Beds
- 3 Baths
- 2,375 sq. ft.
- Single family
- Active
Listed by: earl endrich
Office: bhhs fox & roach - hockessin
MLS#:DENC2105858
Source:BRIGHTMLS
Price summary
- Price:$569,900
- Price per sq. ft.:$239.96
- Monthly HOA dues:$315
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....
Contact an agent
Home facts
- Year built:2021
- Subdivision & Development:WHISPERING WOODS
- Listing ID #:DENC2105858
- Added:59 day(s) ago
- Updated:September 06, 2026 at 01:49 PM
Rooms and interior
- Bedrooms:3
- Total bathrooms:3
- Full bathrooms:2
- Half bathrooms:1
- Flooring:Hardwood
- Dining Description:Combination Dining/Living, Dining Area, Dining Room
- Bathrooms Description:Primary Bath(s), Primary Bathroom
- Kitchen Description:Breakfast Area, Built-In Microwave, Built-In Range, Dishwasher, Kitchen - Eat-In, Kitchen - Gourmet, Kitchen - Island, Stainless Steel Appliances
- Bedroom Description:Entry Level Bedroom, Primary Bedroom
- Basement:Yes
- Basement Description:Full
- Living area:2,375 sq. ft.
Heating and cooling
- Cooling:Central A/C
- Heating:Forced Air, Natural Gas
Structure and exterior
- Roof:Asphalt
- Year built:2021
- Building area:2,375 sq. ft.
- Lot area:0.19 Acres
- Architectural Style:Carriage House
- Construction Materials:Vinyl Siding
- Exterior Features:Patio(s), Porch(es)
- Foundation Description:Concrete Perimeter
- Levels:2 Stories
Schools
- High school:MIDDLETOWN
- Middle school:ALFRED G WATERS
- Elementary school:CEDAR LANE
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$569,900
- Price per sq. ft.:$239.96
- Tax amount:$4,538 (2025)
Features and amenities
- Amenities:Curved Staircase
Parking
- Parking description:Attached Garage, Garage - Front Entry
- Garage:Yes
- Garage spaces:2
New listings near 529 Contemplation Way
- Coming Soon
$550,000Coming Soon4 beds 4 baths2,800 sq. ft.716 Guido Dr, MIDDLETOWN, DE 19709
MLS# DENC2110676Listed by: THYME REAL ESTATE CO LLC - Coming Soon
$695,000Coming Soon4 beds 3 baths2,625 sq. ft.105 Ruth Dr, MIDDLETOWN, DE 19709
MLS# DENC2110632Listed by: THYME REAL ESTATE CO LLC - Coming Soon
$749,000Coming Soon4 beds 3 baths3,425 sq. ft.2744 Van Cliburn Cir, MIDDLETOWN, DE 19709
MLS# DENC2110562Listed by: PATTERSON-SCHWARTZ-MIDDLETOWN - Coming Soon
$559,900Coming Soon3 beds 3 baths2,475 sq. ft.1243 Gwynedd Dr, MIDDLETOWN, DE 19709
MLS# DENC2110286Listed by: EMPOWER REAL ESTATE, LLC - Coming Soon
$680,000Coming Soon4 beds 3 baths3,000 sq. ft.1207 Glossy Ibis Ct, MIDDLETOWN, DE 19709
MLS# DENC2110216Listed by: CROWN HOMES REAL ESTATE - Coming Soon
$495,900Coming Soon4 beds 3 baths2,100 sq. ft.4 Lindsay Ct, MIDDLETOWN, DE 19709
MLS# DENC2108722Listed by: BHHS FOX & ROACH-CHRISTIANA - New
$384,000Active4 beds 4 baths2,040 sq. ft.357 Edgar Degas Ln #110, MIDDLETOWN, DE 19709
MLS# DENC2110688Listed by: BLENHEIM MARKETING LLC - New
$476,500Active3 beds 3 baths2,358 sq. ft.353 Edgar Degas Lane Edgar Degas #108, MIDDLETOWN, DE 19709
MLS# DENC2110690Listed by: BLENHEIM MARKETING LLC - New
$637,500Active4 beds 4 baths2,499 sq. ft.1023 Applecross Dr, MIDDLETOWN, DE 19709
MLS# DENC2110414Listed by: BRYAN REALTY GROUP - New
$398,500Active3 beds 3 baths2,600 sq. ft.1322 Carrick Ct, MIDDLETOWN, DE 19709
MLS# DENC2110494Listed by: EXP REALTY, LLC
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2023 - 2026 ERA Franchise Systems LLC. All rights reserved. ERA Franchise Systems LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. ERA, ERA Real Estate powered, and their respective logos are registered service marks of ERA Franchise Systems LLC. Each office is independently owned and operated.