Whispering Woods Real Estate

Whispering Woods Real Estate

Welcome to Whispering Woods, a serene and picturesque subdivision nestled in the heart of the United States. This charming community offers a perfect blend of tranquility and modern convenience, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle.

Whispering Woods is enveloped by lush greenery and mature trees, creating a natural sanctuary that inspires relaxation and outdoor activities. The carefully planned layout of the subdivision features spacious lots, ensuring that each home enjoys privacy while still fostering a sense of community. Residents can often be found strolling along the winding pathways or gathering at the community park, where children play and neighbors connect.

The subdivision is conveniently located near essential amenities, including shopping centers, restaurants, and schools, making daily errands a breeze. With easy access to major highways, commuting to nearby cities is simple and efficient, allowing residents to enjoy the best of both worlds: a peaceful retreat and urban accessibility.

Whispering Woods is not just a place to live; it’s a lifestyle. The community hosts seasonal events, fostering camaraderie among neighbors and creating lasting friendships. Whether you’re enjoying a summer barbecue or participating in a fall festival, there’s always something happening in this vibrant neighborhood.

If you’re looking for a place that combines natural beauty, community spirit, and convenient living, Whispering Woods is the perfect choice. Come and discover the charm of this delightful subdivision and envision your future in this idyllic setting. Your dream home awaits!

Newest Listings in Whispering Woods

$492,000
3 Beds ⋅ 3 Baths

1702 Oak Ct, Monmouth Junction

Listing courtesy of Sun Realty. Contact: (631) 965-3539
$390,000
2 Beds ⋅ 2 Baths
Welcome to this beautifully updated and move-in-ready home! The bright and inviting main level features stunning wood floors (2025) and flows seamlessly into a fully remodeled kitchen (2025). The kitchen boasts crisp white cabinetry, stainless steel appliances, quartz countertops, peninsula featuring a striking quartz waterfall countertop with a sleek flat cooktop, and new smart inset ceiling lights. Two large newly added windows in the kitchen add natural light. The adjacent dining room is highlighted by a new smart chandelier and upgraded French doors (2025). Upstairs, you will find two generously sized bedrooms. The entirely remodeled full bathroom (2026) serves as a luxurious retreat, showcasing a large glass walk-in shower with custom tile work and a modern rainfall showerhead. Smart inset ceiling speakers in this space pair to your cell phone for easy listening opportunities, while a contemporary front lit and anti-fog mirror sits above a burnished stone floating vanity. The basement offers a spacious finished living area alongside an unfinished utility/laundry space, a workbench with built-in shelving, and a convenient half bathroom. It is further enhanced by newly added ceiling insulation (2026). The house features many updates including windows throughout the home (2023), roof with a 30 year warranty (2020), fully refreshed exterior paint (2023), and added windows to both the bathroom and kitchen to increase natural light. Outdoor entertaining is a dream with the covered deck located right off the dining room, leading down to a beautifully landscaped yard complete with a shed for storage, brick lined gravel path, and two gorgeous wooden pergolas.

422 Blossom Tree Dr, Annapolis

Listing courtesy of Samson Properties. Contact: 7033493900
$500,000
4 Beds ⋅ 2 Baths
Coming soon!

379 Blossom Tree Dr, Annapolis

Listing courtesy of Samson Properties. Contact: 3018542155
$369,900
3 Beds ⋅ 3 Baths
Welcome to 1424 Foxwood Ct, a beautifully updated townhome in sought-after Whispering Woods. Step outside to a large deck with stairs to the fenced backyard, a paved patio, raised garden bed, and new shed — outdoor living space rarely found in this price range. Inside, new flooring runs through all three levels, complemented by recessed lighting, an updated kitchen and bathrooms, and a new entry door with all-new interior doors. The lower level offers additional finished living space with its own full bathroom — ideal for a guest suite, office, or extra living space. A new roof and gutters add peace of mind for years to come.

1424 Foxwood Ct, Annapolis

Listing courtesy of Redfin Corp. Contact: 3016586186
$404,000
3 Beds ⋅ 2 Baths
Welcome to 413 Blossom Tree Court, a beautifully cared‑for duplex in the highly sought‑after Whispering Woods community on the Broadneck Peninsula. This lovingly maintained 3‑bedroom, 2‑full‑bath home offers a functional layout, thoughtful updates, and exceptional access to parks, trails, and everyday conveniences. The main level features a bright, renovated (2023) kitchen with granite countertops, stainless steel appliances, and abundant natural light. A dedicated dining area flows seamlessly into the kitchen, with expansive sliders opening to a private deck overlooking a large backyard and lush wooded views—an ideal setting for play, gardening, entertaining, or simply relaxing in your own outdoor retreat. Upstairs, you’ll find three comfortable bedrooms, including a spacious primary with double closets, and a tastefully renovated full hall bath (2023) conveniently located for all bedrooms. The partially finished lower level offers outstanding flexibility with a full bathroom, making it perfect for a guest suite, 4th bedroom, recreation room, or home office. The unfinished portion includes the laundry area, utilities, and direct walk‑out access to the backyard, providing convenience and excellent potential for future expansion. Opportunities include adding a lower‑level patio or a three‑season room beneath the existing deck. Additional features include hardwood‑look laminate flooring throughout, new HVAC (2023), and a hot water heater (2000). Whispering Woods offers a low HOA of just $347/year, playgrounds, walking paths, and easy access to the newly completed Broadneck Peninsula Trail. From your front door, you can bike or walk to grocery stores, restaurants, the library, Broadneck Park, and even Sandy Point State Park. Located on a quiet, less‑dense street within the community, this home provides exceptional convenience to Route 50, Route 2, and Route 97, with an easy commute to Baltimore, Washington, the Bay Bridge, the Naval Academy, and historic Annapolis. Situated in the award‑winning Broadneck school district, this is a wonderful opportunity to own a well‑loved home in one of Broadneck’s most desirable neighborhoods.

413 Blossom Tree Ct, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$364,000
3 Beds ⋅ 2 Baths
Open House Sunday 11am-1pm!Rarely available end-unit townhome in sought-after Whispering Woods! Brand New 50 yr architectural roof! This move-in ready 3 bedroom, 1.5 bath home offers privacy and charm surrounded by mature trees. Enjoy spacious living areas, and a fenced rear yard perfect for relaxing or entertaining. Private shed provides additional storage. Conveniently located near shopping, restaurants, parks, and major commuter routes with easy access to Downtown Annapolis, Route 50, and I-97.

1503 Lodge Pole Ct, Annapolis

Listing courtesy of CENTURY 21 New Millennium. Contact: 4102669005
$423,000
2 Beds ⋅ 2 Baths
Nestled among the trees in the desirable 55+ Whispering Woods community of Middletown, Delaware, this charming coastal-style villa offers the ease of single-level living with a thoughtfully designed layout and quality finishes throughout. Featuring two bedrooms and two full bathrooms, the home combines comfort and style with luxury vinyl plank, plush carpet, and tile flooring. The open floor plan creates a bright and welcoming living space, enhanced by recessed lighting in the entry, living room, and kitchen. The spacious kitchen is designed for both everyday living and entertaining, complete with a gas stove, center island, and seamless flow into the main living and dining areas. The inviting primary suite showcases an elegant tray ceiling, abundant closet space, and a private ensuite bathroom featuring a step-in shower with built-in bench and safety grab bar and a spacious vanity. A second bedroom and full bath provide comfortable accommodations for guests or a home office. An energy efficient, on-demand hot water system not only helps reduce utility costs but also provides nearly instant hot water throughout the home for added comfort and convenience. The front garden and manicured lawn add to the curb appeal of this immaculately maintained residence. Enjoy low-maintenance living while taking advantage of exceptional community amenities, including a clubhouse with a fitness center, outdoor pool, and pickleball courts. Conveniently located, this home offers the perfect blend of peaceful, tree-lined surroundings and easy access to shopping, dining, healthcare and major roadways. This is a rare opportunity to experience low-maintenance living in an attractive neighborhood designed for comfort, convenience and an active lifestyle.

1428 Whispering Woods Rd, Middletown

Listing courtesy of Compass. Contact: 3022734998
$384,500
3 Beds ⋅ 2 Baths
Set on a corner lot in Whispering Woods, this updated and move-in-ready end-unit townhome offers 3 bedrooms, 2 full baths, and a spacious, fully fenced backyard. Inside, you'll find abundant natural light, granite countertops, stainless steel appliances, updated baths, and a finished walkout lower level with direct outdoor access, making it ideal for a family room, home office, playroom, or guest space. The fully fenced backyard provides plenty of room to relax, entertain, garden, or let pets play, while a new roof adds peace of mind. Conveniently located just minutes from Route 50, downtown Annapolis, shopping, dining, parks, and more.

1528 Lodge Pole Ct, Annapolis

Listing courtesy of Taylor Properties. Contact:

$579,900
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
$390,000
3 Beds ⋅ 3 Baths
Turn-Key Annapolis Gem! Beautifully renovated inside and out, this home features flowing hardwoods on the main level and a gourmet kitchen with KraftMaid soft-close shaker cabinets, under-cabinet lighting, granite counters, Samsung SS appliances, twin pantries, and a custom island with pendant lighting. Enjoy seamless outdoor living on the large deck with a custom electronic awning, or on the walk-out level's extended paver patio with a built-in swing, seating, garden beds, shed, and fully fenced yard. The upper level boasts durable laminate floors, bedroom chair railings, and a primary suite with two closets (including a walk-in). The partially finished lower level includes a full bath, flex space for a gym or office, and top-of-the-line 2024 Samsung Smart Black Stainless laundry appliances. Prime location minutes to Historic Annapolis, DC, and Baltimore, zoned for top Broadneck district schools: Windsor Farm, Severn River Middle, and Broadneck High!

1154 Riverboat Ct, Annapolis

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690
$495,000
2 Beds ⋅ 2 Baths
Welcome to this warm and inviting end unit carriage-style home located in the 55+ community neighborhood of Whispering Woods. This home offers one floor living with 2 bedrooms & 2 full baths on the main level. Upon entering you will be greeted by LVP flooring which resembles a hardwood look that flows throughout the main living areas. The open-concept layout features a modern kitchen with quartz countertops, stainless steel appliances, a gas range, and a large island perfect for casual dining or entertaining. The living area offers a gas fireplace and outdoor access. The spacious primary suite is a true retreat with a tray ceiling, a walk-in closet and a beautifully tiled shower in the en-suite bath. Lots of windows allow natural light to stream in adding warmth to the home, but if you desire fresh air, just step outside to enjoy the beautifully designed screened in porch. The residents enjoy access to a clubhouse, swimming pool, and a variety of other top-tier amenities designed to support an active and social lifestyle. Conveniently located near shopping, dining and recreational options, this home is an exceptional opportunity to embrace low-maintenance, resort-style living. Schedule a showing today and discover the charm and comfort of this wonderful home!

1426 Whispering Woods Rd, Middletown

Listing courtesy of Crown Homes Real Estate. Contact: (302) 504-6147
$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
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