Whispering Woods Homes for Sale

Whispering Woods Homes for Sale

Welcome to Whispering Woods, a picturesque subdivision nestled in the heart of Annapolis, Maryland. This charming community is located in Anne Arundel County, offering a tranquil and serene setting for residents to call home. Whispering Woods is known for its tree-lined streets, well-manicured lawns, and a strong sense of community.

Homes for sale in Whispering Woods are truly something special. From cozy bungalows to spacious family homes, there is something to suit every lifestyle and budget. True to its name, Whispering Woods offers homes with beautiful wooded views, providing a sense of privacy and tranquility. Residents can enjoy the peaceful surroundings while still being close to all the amenities that Annapolis has to offer.

Whether you're looking for a quiet retreat or a place to raise a family, Whispering Woods has something for everyone. With its convenient location, top-rated schools, and friendly atmosphere, it's no wonder why so many people are proud to call Whispering Woods home. Come and discover the beauty and charm of this lovely subdivision in Annapolis, Maryland.

Newest Whispering Woods Homes for Sale

$500,000
4 Beds ⋅ 2 Baths
Beautifully updated 4 bedroom, 2 full bath home with a fully finished walkout lower level in a convenient Annapolis location. The main level offers an open living, dining and kitchen area with a large center island, updated cabinetry, quartz countertops, stainless steel appliances and designer lighting. Step directly from the kitchen onto the rear deck overlooking the fully fenced backyard, perfect for relaxing or entertaining. Three bedrooms and a beautifully renovated full bathroom complete the main level. The lower level includes a spacious recreation room with walkout access to the backyard, a fourth bedroom, second full bathroom, utility room and additional storage space. Recent updates include a remodeled kitchen and bathrooms, luxury vinyl plank flooring, carpet, modern lighting and fresh finishes. Conveniently located near Downtown Annapolis, shopping, dining, parks, commuter routes and the U.S. Naval Academy.

379 Blossom Tree Dr, Annapolis

Listing courtesy of Samson Properties. Contact: 3018542155
$569,900
3 Beds ⋅ 3 Baths
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

Listing courtesy of BHHS Fox & Roach - Hockessin. Contact: (302) 999-9999
$645,000
4 Beds ⋅ 2 Baths
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

Listing courtesy of HomeZu by Simple Choice. Contact: (855) 885-4663
$399,000
3 Beds ⋅ 2 Baths
FRESHLY PAINTED AND NEW CARPET THROUGHTOUT. WALKOUT BASEMENT. THANK YOU FOR SHOWING

1531 Hickory Wood Dr, Annapolis

Listing courtesy of Real Estate Depot. Contact:

$895,000
5 Beds ⋅ 4 Baths
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

Listing courtesy of Fathom Realty NJ, LLC. Contact: 856-344-4663
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