Whispering Woods Real Estate

Whispering Woods Real Estate

Welcome to Whispering Woods, a serene subdivision nestled in the heart of the United States, where nature and community blend seamlessly to create a truly idyllic living experience. This enchanting neighborhood is designed for those who appreciate the beauty of the outdoors and the warmth of a close-knit community.

Whispering Woods is characterized by its lush landscapes, towering trees, and winding pathways that invite residents to explore the natural beauty surrounding them. The subdivision features a variety of thoughtfully designed homes that cater to diverse lifestyles, from charming single-family residences to modern townhouses, ensuring that there is something for everyone.

Families will find Whispering Woods to be an ideal place to raise children, with excellent schools located just a stone's throw away. The community is rich in amenities, including parks, playgrounds, and recreational areas that encourage outdoor activities and foster a sense of belonging. Whether it's a leisurely stroll through the woods, a weekend picnic, or a game of soccer at the local field, there's no shortage of opportunities for fun and connection.

In addition to its natural beauty, Whispering Woods boasts convenient access to shopping, dining, and entertainment options, allowing residents to enjoy the best of both worlds. With a strong sense of community and a commitment to preserving the environment, Whispering Woods is more than just a place to live—it's a lifestyle.

Discover the charm and tranquility of Whispering Woods, where your dream home awaits amidst the whispers of nature. Come and experience the perfect blend of comfort, community, and convenience in this delightful subdivision!

Newest Listings in Whispering Woods

$519,900
3 Beds ⋅ 3 Baths
Welcome to this beautiful, like-new end-unit Carriage House in the highly sought-after 55+ community of Whispering Woods! Built just five years ago, this impeccably maintained 3-bedroom, 3-bath home offers the perfect blend of modern style, low-maintenance living, and exceptional community amenities. Ideally situated on a premium homesite backing to tranquil woods, with open space on one side and a nearby pond on the other, this home provides both privacy and scenic surroundings. A two-car garage, private driveway, and convenient overflow parking ensure plenty of space for residents and guests alike. Step inside to discover luxury vinyl plank flooring throughout most of the main level and an inviting open-concept layout that seamlessly connects the living room, dining area, and kitchen. The spacious living room is anchored by a gas fireplace and enhanced with recessed lighting. Designed for both everyday living and entertaining, the kitchen features Quartz countertops, stainless steel appliances, a center island with breakfast bar seating, soft-close cabinetry, a subway tile backsplash, gas cooking, and a spacious pantry. Just off the kitchen, enjoy your morning coffee or evening relaxation in the screened porch, which opens to a patio overlooking the peaceful backyard. The spacious first-floor primary suite offers a tray ceiling, walk-in closet, and a private en-suite bath with luxury vinyl plank flooring. Also on the main level are a second bedroom, an additional full bath, a convenient laundry room, and direct access to the garage. Upstairs, you'll find a generous loft that offers endless possibilities for a home office, hobby room, or additional living space, along with a third bedroom and another full bathroom – perfect for visiting family and friends. Additional upgrades include beautiful plantation shutters, enlarged moldings, dual-zone HVAC, a tankless water heater, LeafFilter gutter protection, and abundant closet space. Life at Whispering Woods means enjoying a truly carefree lifestyle. The HOA takes care of landscaping, lawn care, snow removal (including driveways), and trash service, allowing you more time to enjoy the community's outstanding amenities. Residents have access to a beautiful clubhouse with a fitness center, community pool, card room, bocce ball courts, and pickleball courts, along with an active social calendar filled with planned events, games, and activities. The community's unique "Neighbors Helping Neighbors" committee fosters a welcoming atmosphere where residents come together to lend a helping hand whenever needed. This move-in ready home offers the perfect combination of comfort, convenience, and community. Don't miss your opportunity to enjoy the exceptional lifestyle that Whispering Woods has to offer!

352 Tranquility Way, Middletown

Listing courtesy of Compass. Contact: 3022029855
$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
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
$385,000
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
$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
$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
$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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