luxury real estate for sale South Dennis, United States

Tucked within the prestigious Windward Estates enclave of East Dennis, this exceptional Royal Barry Wills-inspired residence built by the iconic Bob McPhee Homes represents the gold standard of Cape Cod craftsmanship. Windward Estates is a private community of just 53 distinctive homes, each thoughtfully sited on generous wooded lots to preserve privacy and individuality. Residents treasure the quiet exclusivity of this neighborhood--known for architectural integrity, gracious homes, and a close-knit atmosphere where generations of families return year after year.Set on a beautifully landscaped lot with no neighbors on three sides and the rear bordering protected Water Department land, this property offers rare privacy while remaining moments from Dennis Pines Golf Course, the Cape Cod Rail Trail, the coveted Northside beaches, and convenient highway access.A classic front entry adorned with distinctive bullseye glass panes welcomes you into a gracious two-story foyer where wide hallways, gleaming hardwood floors, and refined moldings reflect the quality of construction throughout. Custom millwork, beadboard accents, chair rails, built-ins, plantation shutters, and tasteful coastal colors create a warm yet sophisticated interior. Designed for both grand entertaining and comfortable everyday living, the home offers more than 4,500 square feet of beautifully arranged living space. The formal living room features custom woodwork, built-in bookcases, and a striking fireplace with black onyx tile surround and custom wrought iron enclosure. The elegant dining room is highlighted by chair rails and a custom picture window overlooking the grounds. At the heart of the home is a spacious chef's kitchen featuring rich cherry cabinetry, high-end appliances, and an impressive 8-foot granite island. The kitchen opens to a welcoming family room with cathedral beamed ceiling and magnificent fieldstone fireplace, creating a relaxed gathering space with views of the private backyard. A thoughtfully designed private wing features two first-floor primary suites positioned in opposite directions for maximum privacy. One suite offers direct access to the bluestone patio along with a walk-in closet, luxurious bath, and adjoining office, nursery, or exercise space. The second primary suite includes generous proportions, a built-in vanity and writing desk, and its own elegant en-suite bath. The rear entry from the separate guest circular driveway leads to a well-appointed mudroom, laundry room, and guest bath, along with access to the large finished room above the garage--an ideal space for a private office, studio, or fitness area. The second level offers three additional spacious bedrooms and a full bath for family and guests. Outside, professionally landscaped grounds feature mature plantings, lush lawns, custom awnings, and an inviting bluestone patio perfect for entertaining. Additional highlights include luxury Kohler fixtures, custom cabinetry and tile in baths, plantation shutters, built-ins, whole-house generator, and a massive full basement offering exceptional storage or future expansion. Meticulously maintained and thoughtfully designed, this remarkable home blends timeless Cape Cod architecture with modern comfort and exceptional privacy in one of East Dennis's most sought-after executive neighborhoods.

Tucked into a desirable South Dennis neighborhood close to conservation land and Northside beaches, this move-in ready and perfectly maintained 2-bedroom, 1-bath home offers easy Cape living. Thoughtfully updated, the home features an updated kitchen and bath, and central air for year-round comfort. The home offers a separate living room with fireplace and a spacious family room overlooking the backyard, providing flexible living and entertaining space. The 3-season porch with multiple sliders brings in abundant natural light and creates a seamless indoor-outdoor feel. Step outside to a maintenance-free deck overlooking a fenced, level yard with a new walkway, large shed, and beautifully simple landscaping--ideal for relaxing or entertaining.

There are certain neighborhoods on Cape Cod that people discover and immediately understand why so few homes are ever available.The kind of places where homes are thoughtfully sited on generous lots, mature landscaping softens the view from the road, and a quiet sense of permanence is immediately apparent. Places where ownership is often measured in decades rather than years, and where homes rarely come to market because they are quietly passed along through neighbors, friends, and family connections before the rest of the world ever knows they are available.Windward is one of those places.This coveted East Dennis enclave of custom McPhee-built homes has long been regarded as one of the area's best-kept secrets. Tucked away just minutes from some of the Cape's best beaches, Windward offers something increasingly difficult to find: privacy, space, and a level of understated elegance that never asks for attention yet quietly commands it.There are no gates here. None are needed.The winding roads, generous setbacks, meticulously maintained homes, and extraordinary pride of ownership create a feeling of exclusivity that is difficult to define but impossible to miss. It is a neighborhood for those who appreciate breathing room, who value quality over flash, and who understand that true luxury is often found in what isn't crowded, hurried, or easily replicated. Perhaps that is why so few homes ever become available. Once people find Windward, they tend to stay. Set near the end of a gentle curve in the road, 9 Baker's Pond enjoys one of Windward's most desirable settings. A sweeping circular driveway welcomes you to this custom Cape, thoughtfully designed to embrace both privacy and natural light. Inside, warm and inviting spaces include an eat-in kitchen with rich cherry cabinetry, a formal dining room ready for holidays and celebrations, and a comfortable living room centered around a handsome fireplace. The first-floor primary suite offers cathedral ceilings and a sense of retreat, while additional bedrooms and flexible living spaces provide room for family and guests. And then comes the surprise. Added by the current owners, the spectacular year-round sunroom was designed to do exactly what it does so beautifully--draw your eyes outward and showcase the extraordinary setting beyond. With soaring cathedral ceilings, shiplap detail overhead, and floor-to-ceiling windows that flood the space with natural light, it serves as both the heart of the home and a window into the remarkable oasis beyond. From here, the entire scene unfolds. What was completely hidden upon arrival reveals itself all at once--a private backyard oasis that feels more boutique resort than private residence. A heated saltwater pool with a cascading waterfall and graceful arcing water jets creates a resort-like experience, while an expansive bluestone patio, colorful plantings, and impeccably maintained grounds provide the perfect backdrop for both grand entertaining and quiet relaxation. The tiki hut cabana--with bar, refrigeration, television, and plenty of room for family and friends--invites spontaneous summer afternoons that effortlessly drift into evening. As landscape lighting begins to glow and the gardens settle into the soft light of dusk, it becomes easy to understand why so many treasured memories have been created here. Perhaps the greatest luxury is that it is all just steps from your back door. A private retreat designed to be enjoyed whenever the mood strikes. Some of the best moments of summer happen not at a destination, but at home. https://media.nausetmedia.com/sites/rgbdabmy/unbranded

Everyone dreams about finding that special Cape Cod neighborhood... the kind where the roads are quiet, neighbors wave as they pass, and evening walks become part of your daily routine.Tucked into a peaceful neighborhood with no cut-through traffic, 42 Diane offers the kind of easy, low-maintenance lifestyle that feels a world away from stress, yet remains close to everything that makes life on Cape Cod so special. Take an evening stroll to Flax Pond for sunsets and fresh air, wander nearby walking trails, or head over to a Cape Cod Baseball League game on a warm summer night -- one of the Cape's most treasured traditions.South side beaches, Bass River, boating, kayaking, dining, shopping, golf, and outdoor recreation are all just moments away, making it easy to fill your days with everything people love about Cape Cod living. Whether gathering with family & friends after a beach day, enjoying backyard cookouts on warm summer evenings, or simply relaxing in quiet comfort of home, this is a place designed for making memories. 42 Diane Ave captures something increasingly hard to find - a welcoming neighborhood, a slower pace, and that unmistakable feeling of being ''Down the Cape. The Cape.

A charming Arthur Lohr-built ranch perfectly located in West Dennis. This 2/3 bedroom, 1 bath home offers hardwood floors, a wood burning fireplace, and an eat-in kitchen filled with natural light, creating a bright feel throughout. A spacious great room with vaulted ceilings provides additional living space, perfect for entertaining and creating classic Cape Cod memories. An additional room is currently used as a third bedroom, offering flexibility for guests or a home office. Recent updates include a new gas furnace (2026), along with a newer roof and hot water heater (2019). The home offers solid bones and tremendous potential to make it your own. Set on a corner lot with a private, natural backyard setting and a small patio area for outdoor enjoyment. Perfectly positioned along Trotting Park Road, offering easy access to South Village, Trotting Park, and West Dennis Beaches in one direction, and local favorites including Cuffy's, Love Farms, The Breakfast Room, and Three Fins Coffee in the other. Ideal for year-round living or a Cape Cod summer retreat. Passed Title V. Washer and dryer located in the Cape Cod basement.

From the outside, this classic East Dennis ranch may feel modest and unassuming--but step inside and you'll discover a home that lives far larger than it appears, now beautifully refreshed and reintroduced to the market.After a thoughtful ''fluff and buff''--including wallpaper removal, fresh interior paint, and elegant coastal staging from end to end--the home has been completely reimagined to showcase its full potential and lifestyle appeal in today's market.Tucked into the quietly treasured neighborhood of Forest Pines, just off historic Route 6A in East Dennis, this is one of those rare Northside settings where homes are seldom available... simply because people don't want to leave. Mature trees, gracious homes, and a peaceful, established setting create that unmistakable Old Cape Cod feel.The location is exceptional--just minutes to Cold Storage Beach, Sesuit Harbor, and the very best of East Dennis and Dennis Village living. Enjoy lobster roll cruises from Sesuit Harbor, morning walks along the bay, afternoons at the beach, and easy access to Dennis Highlands and Dennis Pines Golf Courses--all part of the everyday rhythm here.Inside, the home offers a warm and welcoming l layout with generous living spaces, abundant natural light, and a flow that lives comfortably for both everyday use and entertaining. Large windows bring the outdoors in, and the rooms feel open, bright, and inviting throughout. A hole house generator completes this generous package of positives! The newly staged interior highlights how effortlessly the home can adapt to today's coastal lifestyle--whether enjoyed as-is or taken to the next level over time. It's a wonderful canvas with both immediate charm and long-term potential. Outside, the private yard offers space to relax, garden, or expand your outdoor living vision in a setting that feels tucked away, yet close to everything that makes East Dennis so special. Comfortable, refreshed, and quietly exceptional, this is a rare opportunity to become part of one of the Northside's most beloved neighborhoods.

Imagine waking up everyday to stunning views of Canoe Pond and the serene sounds of nature. This spacious 3 bedroom- 3 bath home isn't just a house it's a lifestyle! Enjoy the tranquility of a quiet neighborhood while being 6 minute drive to Brewsters Paines Creek Beach and its famous flats at low tide. Whether you're canoeing, paddle boarding, fishing, out for a jog or walking a dog, this home offers endless outdoor adventures right at your doorstep. Experience breathtaking sunsets and make lasting memories in this Cape Cod hidden gem. Renovations: Roof, Gas Heat, Central Air, RINNI Tankless Hot Water, Kitchen cabinets Granite kitchen counters, Guest Bath, Whole House Generator and More- Lovingly Maintained. Don't miss out on your chance to live where everyday feels like a vacation. turn key for your summer enjoyment.

Stunning Brewster Home!Just minutes from beaches and premier golf courses, this meticulously maintained residence offers the perfect blend of casual elegance and modern comfort. The bright, open floor plan features a gourmet kitchen with center island, custom cabinetry, and gleaming Roca tile floors. The inviting living room flows into the dining area, featuring a soaring ceiling, a gas fireplace and sliding doors that open to a spacious deck overlooking the private backyard.Throughout the home, you'll find custom window shutters and exquisite hardwood floors. There are two primary suites, one on each level, along with two guest bedrooms--one currently used as a sitting room. Additional highlights include beautifully appointed bathrooms, 1st floor laundry, natural gas heat, central air conditioning, a whole-house generator, irrigation system, and an atttached two-car garage with potential bonus space above. A welcoming front porch and professional landscaping complete this stunning oasis, privately nestled on a cul-de-sac surrounded by protected greenspace in a lovely neighborhood.

Renovated in 2024, this exceptional two-level home in the highly sought-after West Dennis area offers endless possibilities. Located less than a mile from the pristine shores of West Dennis Beach, it perfectly blends modern comfort with coastal charm. Whether you're looking for a spacious year-round residence, a relaxing vacation retreat, or an income-generating investment, this home's versatile layout and prime location provide the ideal foundation for your vision. The first floor currently generates approximately $25,000 per year in rental income. Don't miss the opportunity to make this beautifully updated property your own. Closing best after September 12, 2026.

Easy Living, Exceptional Value & a Lifestyle You'll Love ... Nestled along a quiet, tree-lined lane in the heart of Kings Way, this lovingly maintained ''A'' unit offers the ease of true one-floor living combined with the flexibility and space that today's buyers appreciate. Conveniently located near the Village Green, post office, community building, pool, and many of Kings Way's most popular amenities, this is one of the best values currently available in the community.A sunny foyer welcomes you into a bright and comfortable home featuring newer hardwood floors, an updated kitchen, updated baths, and a floor plan designed for effortless living. The cathedral-ceiling living room is filled with natural light and flows seamlessly into the dining area, creating an inviting space for everyday living and entertaining.The main level offers everything you need on one floor, including two bedrooms, two full baths, first-floor laundry, and direct access from the attached one-car garage. The spacious primary suite features a private bath and walk-in closet, while the guest bedroom and second full bath provide comfort and privacy for visitors. Outside, a charming private courtyard offers the perfect opportunity to indulge your green thumb, creating a welcoming outdoor retreat filled with colorful flowers, container gardens, or seasonal plantings. To the rear of the home, a sprawling 27-foot deck overlooks the golf course while maintaining a wonderful sense of privacy. Whether hosting summer gatherings with family and friends or simply enjoying a quiet morning coffee or evening glass of wine, this outdoor living space becomes a natural extension of the home. The finished walkout lower level expands the living space considerably with a large family room, half bath, cedar closet, workshop, storage room, and abundant space for guests, hobbies, a home office, exercise room, or creative pursuits. Whether you're downsizing without sacrificing space or simply want room for family and friends to visit, this flexible lower level adapts beautifully to your needs. Kings Way is synonymous with low-maintenance living and an active Cape Cod lifestyle. Residents enjoy golf, tennis, pickleball, pools, walking trails, a popular restaurant with fine dining, pub and bar, community gathering spaces, social clubs, professional on-site management and maintenance, post office services, banking services, and a welcoming neighborhood atmosphere. Offering modern updates, comfortable one-floor living, generous bonus space, and access to one of Cape Cod's most complete lifestyle communities, this inviting home proves that luxury condominium living can still be remarkably affordable. For buyers seeking a move-in ready home that reflects today's lifestyle within an established and beautifully maintained community, this lovingly cared-for residence is a rare opportunity to enjoy all that Kings Way has to offer.

If you've been searching for a truly turnkey home, look no further. This absolutely pristine 3 bedroom, single level residence offers the perfect blend of comfort, style, and convenience, featuring two private en-suite bedrooms. Thoughtfully updated throughout, the home boasts new siding and windows, enhancing both curb appeal and energy efficiency. The updated white kitchen showcases beautiful stone countertops, stainless steel appliances, and a bright, inviting atmosphere ideal for everyday living and entertaining. The welcoming living room features a fireplace, creating the perfect gathering space for relaxing evenings and cozy Cape Cod winters. The spacious primary suite offers a stunning tiled shower and thoughtfully updated finishes. Comfort is ensured year round with an efficient heat pump providing air conditioning for warm summer days. Solar panels help offset energy costs, adding efficiency and longterm savings. The finished lower level provides valuable additional living space, ideal for guest overflow, a home office, recreation room, or hobby area. Situated on a desirable corner lot in Captain's Village, one of South Yarmouth's most sought after neighborhoods, this home enjoys close proximity to beaches, shopping, dining, and schools. A onec ar garage provides convenient parking and additional storage space. Step outside to enjoy the backyard and outdoor shower, perfect for rinsing off after a day at the beach and embracing the Cape Cod lifestyle. Move right in and start enjoying everything this exceptional home has to offer.

Cape Cod ease starts here. Bright and beautifully maintained end unit H-Style townhouse, turnkey lifestyle buyers are looking for, privacy, space, and resort-style amenities just minutes from Dennis and Yarmouth beaches. The entrance courtyard w/ maple and weeping cherry trees, while a lush brick side courtyard with perennial plantings and another miniature weeping cherry creates a peaceful outdoor escape. Generous deck adds more room to relax, entertain, or simply enjoy the Cape Cod air. Inside, the home feels light, calm, and instantly welcoming with soothing wall colors, hardwood flooring, and abundant natural light. The large eat-in kitchen features granite countertops, stainless steel appliances, pantry, recessed lighting, skylight, laundry and sliders leading directly to the gated brick courtyard. 2+ bedrooms, a loft, 4 bathrooms, and a finished walkout basement with plenty of storage, this home offers flexible space for guests, work, hobbies, or extended stays. A 2-car garage and nearby visitor parking add convenience makes this an easy choice ready to start enjoying Cape Cod now. HOA fees include golf, pools, tennis & more active lifestyle or a place to unwind. This is It!

Quintessential Cape Cod LIFESTYLE: A classic Cape summer home (year-round too!), on sought-after Fisk Street, a few minutes drive to iconic West Dennis Beach. This home has been loved and cared for as a family vacation spot for decades, and you can feel that vibe as you explore. The home features hardwood floors, 3 bedrooms (2 on first floor, 1 upstairs) plus multiple overflow spaces including a spacious attic over the garage for storage. In addition to the detached, one-car garage, there's also a sizable shed. And, of course, don't forget the outdoor shower! The home sits on .66 acres, a larger lot in the area; the rolling green backyard makes the property all the more special. You'll definitely enjoy making memories here!

Just minutes from Nantucket Sound beaches, this spacious 2-bedroom, 2.5-bath townhouse-style condominium offers bright, inviting living spaces and an exceptional location for year-round living or a perfect summer retreat. The home is filled with lots of natural light and features hardwood floors, custom-painted wood accent walls, an aesthetic fireplace that adds warmth and character to the living area. The full kitchen has newer appliances (needs updating) and flows easily into the dining room, where sliding doors open to a generous private deck surrounded by mature plantings for added privacy. Beyond the deck, enjoy shared common area with flowering trees and a firepit--ideal for relaxing or entertaining. A practical mudroom includes in-unit laundry and a convenient half bath. The finished lower level, complete with a full bath, provides flexible space for a family room, exercise studio, game room or guest overflow. Upgrades include a new gas heating system, new AC units, new electrical panel, and newer windows. Ideally located close to beaches, Sea View Park & local restaurants. Final Condo Docs will be provided.

A Cape Cod Story Worth Living--On a road named for Cape Cod author Joseph Crosby Lincoln, this year-round 2 bedroom Cape style home sits just a short distance from the shores of Nantucket Sound -- where the rhythms of coastal life that Lincoln so famously celebrated are still very much alive today. Brewster-born, Lincoln charmed readers with his humorous and affectionate portrayals of Cape Cod village life.Step inside and discover hardwood floors, newer appliances, and a cozy gas fireplace perfect for curling up on a winter evening with one of the Cape stories you'll find waiting on the bookshelf. The location is simply unbeatable. West Harwich puts you moments from the popular restaurants, shops, and marinas of Harwich Port village, and a day trip to Nantucket is an easy adventure. This is a neighborhood people return to year after year and stay forever.The patio is ideal for summer entertaining, and the attached one-car garage adds convenience. For those with an eye toward the future, the second floor holds expansion potential with room for two additional bedrooms and a bath.This is your opportunity to write your own Cape Cod story, one summer memory at a time. Close to Belmont Rd and Pleasant Rd Beaches

Welcome to Bentley Woods, a new subdivision tucked away in the desirable Headwaters neighborhood. This cleared 0.92-acre lot offers an exceptional opportunity to build your custom home in a peaceful, nature-filled setting.Enjoy direct access to adjacent conservation land and the Cape Cod Rail Trail, with miles of biking and walking trails right from your doorstep. The property is also conveniently located near Hinckley Pond, perfect for kayaking, fishing, and enjoying the outdoors.A rare offering in a sought-after neighborhood--bring your plans and start building at Bentley Woods.

A moment away from the launching dock on Bass River, this property enjoys a charming corner lot setting. This two-story four bedroom house boasts an open floor plan with a cathedral ceiling, great room, eat in kitchen and formal dining room. Completing the first floor is an en suite bedroom. The spacious second floor is a sunny retreat with two bedrooms and a grand en suite primary bedroom. Highlighting the gardens is a koi pond with a fountain and deck overlooking majestic trees and perennial plantings. A two car garage and desired full lower level offers storage convenient to coastal living. Proximity to a private deeded beach ensures enchanting summer enjoyment.

Welcome to Bentley Woods, a new subdivision tucked away in the desirable Headwaters neighborhood. This cleared 0.92-acre lot offers an exceptional opportunity to build your custom home in a peaceful, nature-filled setting. Enjoy direct access to adjacent conservation land and the Cape Cod Rail Trail, with miles of biking and walking trails right from your doorstep. The property is also conveniently located near Hinckley Pond, perfect for kayaking, fishing, and enjoying the outdoors. A rare offering in a sought-after neighborhood--bring your plans and start building at Bentley Woods.

Now offered with a significant $20,000 price improvement, this beautifully refreshed Kings Way ''D'' style end-unit has been thoughtfully re-staged, re-photographed, and completely reintroduced to the market with a fresh new look and feel. Tucked into one of the most peaceful and private settings within the community, the home offers an exceptional combination of space, comfort, and resort-style Cape Cod living.Sunlight pours through multiple exposures, filling the main level with warmth and natural light. Hardwood floors, a striking granite gas fireplace, and an open flowing layout create an inviting atmosphere perfect for both everyday living and entertaining. The dining area opens to a sunny deck overlooking the manicured fairways of the Kings Way golf course -- an ideal setting for morning coffee, outdoor dining, or relaxing at the end of the day.The kitchen features quartz countertops, an eat-in dining area, and convenient first-floor laundry, while the main-level primary suite offers easy one-floor living with a walk-in closet and private bath.A standout feature rarely found at Kings Way is the extraordinary finished walk-out lower level offering three additional finished rooms, a full bath, and its own gas fireplace. Perfect for guests, extended family, home office space, hobbies, or media room flexibility, this level dramatically expands the home's livability and functionality. Fresh updates and new staging now showcase the tremendous versatility of the space. Outside, the fenced side yard provides a rare private outdoor area ideal for gardening, entertaining, or simply enjoying the peaceful surroundings. Direct access to the golf course enhances the seamless connection to the beautifully landscaped grounds. With over 2,700 square feet of living space, 2+ bedrooms, 3.5 baths, and a two-car garage, this move-in ready home offers outstanding value within the highly sought-after Kings Way community, where residents enjoy golf, tennis, pickleball, dining, social activities, and easy access to the beaches, harbors, villages, and coastal charm of Dennis and Yarmouth.

Set within the highly coveted Fingers neighborhood enclave of West Dennis, this exceptional waterfront home offers a rare blend of comfort, style, and direct water access. Perfectly positioned along the Bass River, the property features a private dock with direct access to Nantucket Sound and the Atlantic Ocean, ideal for coastal living at its finest. Inside, the home is thoughtfully updated and renovated throughout, showcasing modern finishes, all-new appliances, and a bright layout designed to maximize the surroundings. Nearly every window frames stunning views, creating a serene and immersive coastal experience from sunrise to sunset.This home is ready for immediate enjoyment or continued investment. The beautifully landscaped grounds reflect meticulous care and pride of ownership, enhancing both curb appeal and outdoor living spaces. With an extensive and proven rental history, this property presents an outstanding opportunity for both personal use and income generation. A true waterfront masterpiece in one of Cape Cod's most desirable neighborhoods.

Expansive, well-maintained Cape Cod style home set on a private 1.31 acre retreat lot with extensive mature landscaping, offering exceptional privacy and a flexible floor plan. This 5 bedroom, 3 bath residence features hardwood floors throughout, central air, a new gas fireplace, and a first-floor office/laundry room ideal for today’s living. The spacious primary suite provides a peaceful retreat, while the spacious basement offers excellent expansion potential. An oversized two-car garage provides ample storage. Outdoor living is designed for entertaining with a beautifully landscaped 3/4-acre fenced backyard, irrigation, storage shed, outdoor shower, built-in basketball hoop, firepit, koi pond, and room for a pool. Ideally located near Gray’s Beach, historic Route 6A, golf, shopping, the Cape Cod Rail Trail, highway access, and local restaurants.