Whispering Woods Homes for Sale

Whispering Woods Homes for Sale

Welcome to Whispering Woods, a serene subdivision nestled in the heart of the United States, where nature and modern living harmoniously intertwine. This enchanting community is characterized by its lush greenery, whispering trees, and a tranquil atmosphere that invites residents to unwind and enjoy the beauty of their surroundings.

Whispering Woods offers a delightful selection of homes for sale, catering to a variety of lifestyles and preferences. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, you’ll find a range of charming properties that suit your needs. Each home is thoughtfully designed, featuring spacious layouts, contemporary finishes, and plenty of natural light, creating an inviting ambiance that feels just like home.

The subdivision is not just about beautiful homes; it’s also about community. Residents enjoy access to well-maintained parks, walking trails, and recreational facilities that encourage an active lifestyle. The friendly neighborhood atmosphere fosters a sense of belonging, where neighbors become friends and community events bring everyone together.

Conveniently located, Whispering Woods is just a short drive away from shopping centers, dining options, and top-rated schools, making it an ideal place for families and professionals alike. Embrace the lifestyle you’ve always dreamed of in Whispering Woods, where every day feels like a retreat into nature while still being close to urban conveniences.

Explore the homes for sale in Whispering Woods today, and discover the perfect blend of comfort, community, and convenience awaiting you!

Newest Whispering Woods Homes for Sale

$500,000
4 Beds ⋅ 2 Baths ⋅ MDAA2152908 MLS
Coming soon!

379 Blossom Tree Dr, Annapolis
$569,900
3 Beds ⋅ 3 Baths ⋅ DENC2105858 MLS
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.

529 Contemplation Way, Middletown
$645,000
4 Beds ⋅ 2 Baths ⋅ MDCA2026970 MLS
This beautiful white brick ranch home with a full basement, two-car garage and large asphalt parking area is a one-of-kind find in southern Maryland. Built by PF Summers in 2002, this home combines thoughtful, wood finishes, and quality craftsmanship in one of Calvert County’s most desirable communities. As you enter the home through its beautiful front porch, you will find an entryway and living room with 12 ft ceilings and crown moldings, a fire place and direct access to beautiful red cedar screened-in back porch overlooking a large back yard with an 8x8 paver fire pit. It could also fit a large deck and pool area. The living room also connects on one side to 3 bedrooms each with 1-2 large closets and full bath with a double vanity and separate enclosed toilet with large cabinet. On the other side, the living room connects to a beautiful dining room with crown moldings, wainscoting and baseboards, and a large kitchen with breakfast nook with views of the red cedar back porch and back yard. The kitchen features large wood cabinets and counter space areas for prepping/serving meals as well as an easy access pantry. The primary bedroom suite, laundry and garage are on this side of the home as well. The garage is a two-car side-load garage with its own large storage area as well as attic space access. The primary suite has views of the backyard and access to future external deck. The suite includes a large bathroom with white tiling, large jacuzzi tub, the walk-in shower with a glass door, spacious his and hers vanities, spacious walk-in closet, and an enclosed toilet with large cabinet. The primary bath is also connected to a separate room containing a washer and dryer, a laundry/utility sink, spacious linen closet and laundry shelving for convenience. The curb appeal shines with this white brick house sitting high on a beautiful 2-plus acre lot including spacious two-car side-load garage, huge asphalt parking area, matching brick mailbox and welcoming front porch. This home also has outstanding possibilities depending on your needs with its 2,626 sq ft walkout basement - ideal for in-law suite, theatre room, entertainment, extra bedrooms in the future or storage (already plumbed for two full baths, laundry room and kitchen and has a separate basement heating/cooling unit and ducting already installed). As a resident of Whispering Woods, you’ll enjoy access to community amenities including a tennis/basketball court and playground.

3005 Blackberry Ln, Prince Frederick
$399,000
3 Beds ⋅ 2 Baths ⋅ MDAA2140770 MLS
FRESHLY PAINTED AND NEW CARPET THROUGHTOUT. WALKOUT BASEMENT. THANK YOU FOR SHOWING

1531 Hickory Wood Dr, Annapolis
$895,000
5 Beds ⋅ 4 Baths ⋅ NJCB2027984 MLS
Located in the prestigious Whispering Woods Community, this pristine two-story, 5 bedroom, 3.5 bath home is truly ready for new beginnings. The second level features a well-appointed main hall bathroom and four spacious bedrooms, including an impressively sized primary suite complete with an oversized walk-in closet and a private ensuite bathroom with spa tub and dual vanities that complete your own peaceful retreat. Step through the exquisite foyer on the main level to find a thoughtfully designed layout offering a formal dining room, den, family room, an additional bedroom, and a full bathroom, making this ideal for guests or multi-generational living. The open kitchen seamlessly connects to the laundry room, three-car garage, and a raised concrete deck with patio that overlooks the in-ground pool, creating the perfect flow for everyday living and entertaining. The finished basement showcases the most recent updates to the home and serves as an entertainer’s dream. This expansive entertainment lair includes an in-home theater room, full bar with barstools, pool table, shuffleboard, video arcade game, and ample space for high-top tables and seating—perfect for hosting memorable gatherings of any size. With generous living space, flexible accommodations for in-laws or extended family, and endless indoor and outdoor entertainment options, this home truly has it all. Schedule your private showing today and experience everything this exceptional Whispering Woods property has to offer.

1869 Whispering Woods Way, Vineland
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