Osterville MA Real Estate & Homes for Sale

A rare opportunity on Osterville's coveted Little Island, this charming four-bedroom home features sweeping views of North Bay on an expansive 1.45-acre lot with park-like grounds. This timeless retreat offers endless possibilities for expansion with pending applications/approvals for a dock and six-bedroom septic system. Upon entering the home, breathtaking views take center stage through oversized windows that look out to a waterside bluestone terrace equally suited for grand entertaining and quiet relaxation. A thoughtful floor plan seamlessly flows from the living room and an adjacent sunroom to the kitchen, dining room, and a formal living room with a fireplace. A bonus room completes the first level, while the second floor features a primary suite overlooking the bay and three guest bedrooms, ensuring ample space for friends and family. A detached two-car garage completes this extraordinary residence, located minutes from Oyster Harbors, Main Street, Dowses Beach, marinas, and everything else Osterville has to offer.

A rare opportunity on Osterville's coveted Little Island, this charming four-bedroom home features sweeping views of North Bay on an expansive 1.45-acre lot with park-like grounds. This timeless retreat offers endless possibilities for expansion with pending applications/approvals for a dock and six-bedroom septic system. Upon entering the home, breathtaking views take center stage through oversized windows that look out to a waterside bluestone terrace equally suited for grand entertaining and quiet relaxation. A thoughtful floor plan seamlessly flows from the living room and an adjacent sunroom to the kitchen, dining room, and a formal living room with a fireplace. A bonus room completes the first level, while the second floor features a primary suite overlooking the bay and three guest bedrooms, ensuring ample space for friends and family. A detached two-car garage completes this extraordinary residence, located minutes from Oyster Harbors, Main Street, Dowses Beach, and marinas.

Welcome to the beautiful village of Osterville. This brand new 2024 Bayside Built timeless custom home is truly a masterpiece located in the cozy Oyster Hills neighborhood. High-end finishes throughout the home include: custom designer marble tile, quartzite counters, Wolf & Subzero appliances, white oak HW floors & trim detail straight out of a custom home magazine. The L-shaped home is positioned perfectly on a large 1-acre corner lot as it seamlessly blends the home into the backyard entertainment area with a large limestone & granite patio, outdoor shower, gas fire pit, & a screened in porch, perfect for those gorgeous summer nights on Cape Cod. A few other additions added by the builder: a full-home Kohler generator, irrigation system, alarm system, multiple TV's & Sonos sound systems, & a 1-year new construction builder warranty as well as many other top-notch finishes. Located only 1 mile from Osterville Main Street's many shops & restaurants & only 1.7 miles to Dowses Beach.

Welcome to the beautiful village of Osterville. This brand new 2024 Bayside Built timeless custom home is truly a masterpiece located in the cozy Oyster Hills neighborhood. The high-end finishes throughout the home include: custom designer marble tile, quartzite counters, Wolf & Subzero appliances, white oak HW floors & trim detail straight out of a custom home magazine. The L-shaped home is positioned perfectly on a large 1-acre corner lot as it seamlessly blends the home into the backyard entertainment area with a large limestone & granite patio, outdoor shower, gas fire pit, & a screened in porch, perfect for those gorgeous summer nights on Cape Cod. A few other additions added by the builder: a full-home Kohler generator, irrigation system, alarm system, multiple TV's & Sonos sound systems, & a 1-year new construction builder warranty as well as many other top-notch finishes. Your new home is located only 1 mile from Osterville Main Street's many shops & restaurants & only 1.7 miles to the picturesque Dowses Beach. Do not miss out on this truly stunning home!

Nestled in the village of Osterville, this ranch-style home offers a year round retreat. Step inside to find an open floor plan that connects the kitchen and living room with a fireplace perfect for entertaining. The home includes two comfortable bedrooms and two bathrooms on the first level, designed for accessibility and convenience. The primary bedroom is en-suite for ultimate convenience. Extend your living space with a large three-season room and deck. The additional space in the basement offers versatility with three large multi-use rooms, an additional bathroom, and a kitchenette. This lower level also provides direct access to a patio and yard. While some updating is needed to restore the home to its original beauty, a passing 3-bedroom Title V inspection has been completed. Positioned on a quiet cul-de-sac, this property is a short drive from Dowses Beach. Experience the charm of Osterville with a vibrant business district featuring everything from art galleries to eateries.

Nestled in the charming village of Osterville, this delightful ranch-style home offers a peaceful year round retreat. Step inside to discover an inviting open floor plan that connects the kitchen to a spacious living room with a cozy fireplace perfect for entertaining and everyday life. The home includes two comfortable bedrooms and two bathrooms on the first level, designed for accessibility and convenience. The primary bedroom is en-suite for ultimate convenience. Extend your living space with a large three-season room and an outdoor deck.The additional space in the basement offers versatility with three large multi-use rooms, an additional bathroom, and a small kitchenette. This lower level also provides direct access to a patio and a private yard. While some updating is needed to restore the home to its original beauty, a passing 3-bedroom Title V inspection has been completed. Positioned on a quiet cul-de-sac, this property is just a short drive from the soft sands of Dowses Beach. Experience the unique charm of Osterville with nearby attractions like the historic Crosby Yacht Yard and a vibrant business district featuring everything from art galleries to cozy eateries.

Beautiful 3290 +- sf new construction by Barnstable Harbor Builders in Osterville, offers 3 levels of Cape Cod living. 3 br en-suite, 4-1/2 ba, primary on both first and 2nd floors, walkout terrace level perfect for entertaining pool side, new 16x32 in ground heated pool w autocover, travertine pool deck, outdoor kitchenette with natural gas grille, enclosed private outdoor rinse area. A 3 season screen w/glass porch to enjoy the sunsets, hardwood floors throughout, fully plastered walls, custom tiled baths and walk in showers, custom cabinetry with quartz counters, Thermador appliances, Andersen windows, 4 zone A/C and natural gas heat, on demand hot water makes this home super energy efficient. Outside details include custom landscaping, large paved driveway, custom fencing, sodded lawns, irrigation,, etc. everything is here! Dowses beach appx 1 mi, and sidewalk to Main Street Osterville including Fancys, Crisp, Wimpys, Five Bays approx 1/4 mi. Property abuts almost 100 acres of conservation land with walking and hiking trails to Josuas and Mica Ponds. Ready for July '24 occupancy.More photos will be added as house is completed.

Welcome to this magnificent 2021-built real estate gem located in the sought-after Wianno neighborhood. With its beautiful open spaces, this home is perfectly designed for accommodating large gatherings and entertaining. The property features an inviting in-ground pool complete with a safety cover, allowing for enjoyment with peace of mind. Additionally, a charming pool house awaits guests, offering a cozy retreat for relaxation and comfort. You will enjoy the enclosed porch complete with a gas fireplace, screens and windows. This luxurious estate boasts six spacious bedrooms, each thoughtfully designed with its own private bathroom, providing residents with unparalleled privacy and convenience. The contemporary yet timeless design of the property harmoniously blends with its surroundings, creating a warm and inviting atmosphere. Enjoy the perks of residing in Wianno, with convenient access to club amenities and beautiful beaches, elevating the overall lifestyle of this extraordinary h

Embrace the epitome of coastal luxury in Osterville Village with this impeccably restored shingle-style residence. A striking entrance with Belgian block stonework leads to professionally landscaped grounds. The main level features an artisanal kitchen, a chic bar area, and a sumptuous primary suite with a marble bathroom. Throughout, find exquisite craftsmanship and upscale details. The sprawling backyard oasis offers privacy and tranquility. This residence is ideally situated between the village and Dowses Beach. Buyers and agents are advised to verify details.

Embrace the epitome of coastal luxury in Osterville Village with this impeccably restored shingle-style residence. A striking entrance with Belgian block stonework leads to professionally landscaped grounds. The main level features an artisanal kitchen, a chic bar area, and a sumptuous primary suite with a marble bathroom. Throughout, find exquisite craftsmanship and upscale details. The sprawling backyard oasis offers privacy and tranquility. This residence is ideally situated between the village and Dowses Beach. Buyers and agents are advised to verify details.

Welcome to Osterville Heights! This lovely, sunny 3 bedroom 2 bath home with attached garage has been well maintained and is ready for it's new family. The main bedroom is generously sized with a private full bath. Enjoy a fireplaced living room, large family room with a gas stove, and two sets of sliders which take you out to a level private back yard. One floor living at it's best. Whether you are looking for a full time home or a summer home on Cape Cod, this home is a must see. Situated on a corner lot in the subdivision Osterville Heights, this home is within 4 miles of several beaches and less than 3 miles to the quaint Village of Osterville where you will find restaurants, shops and galleries.

Envision your forever estate on the private, gated island of Oyster Harbors. This elevated 1.31-acre parcel offers the perfect canvas for your dream home. An iconic Royal Barry Wills 3,877 square foot home is currently sited, but expansion or a new home, pool, and guest house are all within reach. Facing the southwesterly trade winds, and the setting sun, this location affords more than 180-degree views in nearly every corner of this estate. The private deep-water dock with ample space for almost any vessel allows you to enjoy the convenience of reaching Edgartown for breakfast in under 20 minutes. Step out of your own Mediterranean style "beach club' and watch your ship come in, embracing the ultimate waterfront lifestyle.

Envision your forever estate on the private, gated island of Oyster Harbors. This elevated 1.31-acre parcel offers the perfect canvas for your dream home. An iconic Royal Barry Wills 3,877 square foot home is currently sited, but expansion or a new home, pool, and guest house are all within reach. Facing the southwesterly trade winds, and the setting sun, this location affords more than 180-degree views in nearly every corner of this estate. The private deep-water dock with ample space for almost any vessel allows you to enjoy the convenience of reaching Edgartown for breakfast in under 20 minutes. Step out of your own Mediterranean style 'beach club' and watch your ship come in, embracing the ultimate waterfront lifestyle.

Welcome to Osterville Heights! This lovely, sunny 3 bedroom 2 bath home with attached garage has been well maintained and is ready for it's new family. The main bedroom is generously sized with a private full bath. Enjoy a fireplaced living room, large family room with a gas stove, and two sets of sliders which take you out to a level private back yard. One floor living at it's best. Whether you are looking for a full time home or a summer home on Cape Cod, this home is a must see. Situated on a corner lot in the subdivision Osterville Heights, this home is within 4 miles of several beaches and less than 3 miles to the quaint Village of Osterville where you will find restaurants, shops and galleries.

Osterville Village! You'll fall in love with this updated ranch that offers a modern and stylish coastal living experience. Enjoy a fully renovated kitchen featuring quartz counters and stainless steel appliances, as well as 2 new bathrooms, updated electrical and plumbing, and HVAC system, this home is move-in ready. The fresh landscaping with new rear patio, fire pit, fencing and plantings enhance its appeal! There's even a large shed that has endless possibilities! The convenient location allows you to walk to all of Osterville's great stores, restaurants, library and churches! It's also a short bike or drive to Dowses Beach and Crosby's Boat Yard.

Osterville Village! Leave your car at home! You'll fall in love with this updated ranch set in the heart of Osterville that offers a modern and stylish coastal living experience with convenience in mind. Enjoy a fully renovated kitchen featuring quartz counters and stainless steel appliances, as well as 2 new bathrooms, updated electrical and plumbing, and HVAC system, this home is move-in ready. The fresh landscaping with new rear patio, fire pit, fencing and plantings enhance its appeal! There's even a large shed that has endless possibilities! The central location allows you to walk to all of Osterville's great stores, restaurants, library and churches! It's also a short bike or drive to Dowses Beach and Crosby's Boat Yard.

"In its proper season, every door is unlocked, every window wide open. People, too, are more open in summer, moving through the house and each other's lives as freely as the wind. Their schools and offices are distant, their guard is down, their feet are bare," writes George Howe Colt. A more lovely door to be unlocked is nearly impossible to find. Open to the shores of Nantucket Sound in Wianno on Cape Cod this this shingled masterpiece offers a magnificent view splayed before you from over 200 feet of shoreline. With shoes a distant memory, step off the covered porch and, feel the lawn, the salt-smoothed seaside deck and finally, the sand. Look back at this 4,028 square foot home framed against an impossibly blue sky with seven bedrooms, multiple gathering areas and a kitchen perfect for cooking up memories as cuisine, and know all is well in your world. There are memories to be made, milestones to celebrate and feelings to restore. Please verify all information contained herein.

''In its proper season, every door is unlocked, every window wide open. People, too, are more open in summer, moving through the house and each other's lives as freely as the wind. Their schools and offices are distant, their guard is down, their feet are bare,'' writes George Howe Colt. A more lovely door to be unlocked is nearly impossible to find than at 265 Sea View Avenue in Wianno, Osterville on Cape Cod. Open to the shores of Nantucket Sound, this shingled masterpiece offers a magnificent view splayed before you from over 200 feet of shoreline. With shoes a distant memory, step off the covered porch and, feel the lawn, the salt-smoothed seaside deck and finally, the sand. Look back at this 4,028 square foot home framed against an impossibly blue sky with seven bedrooms, multiple gathering areas and a kitchen as perfect for cooking up memories as cuisine, and know all is well in your world. An expansive seaside lawn offers endless possibilities for gatherings, games, tents or even a pool. There are memories to be made, milestones to celebrate, feelings and souls to restore from this ultimate coastal escape. Call to arrange an in-person visit. Please verify all information.

Located a short stroll from Osterville Village, this shingle-style home showcases stunning architectural details and scenic views over Wianno Golf Course and Parker Pond. Exquisite craftsmanship is on full display throughout, from a spacious covered porch that greets visitors to a gourmet kitchen with honed granite countertops and cherry cabinetry. The first-floor primary suite includes a luxurious marble bathroom and secluded home office. On the second floor, an open family room is seamlessly connected to the outdoors with front and back decks, while offering the utmost convenience with a thoughtfully designed kitchenette. Two bedrooms and two bathrooms complete the second floor. Additional highlights include a four-car garage with a self-contained apartment above, a lush backyard, and a large bluestone patio. Mere minutes from everything Osterville has to offer, this extraordinary residence delivers the quintessential Cape Cod lifestyle.

Located a short stroll from Osterville Village, this shingle-style home showcases stunning architectural details and scenic views over Wianno Golf Course and Parker Pond. Exquisite craftsmanship is on full display throughout, from a spacious covered porch that greets visitors to a gourmet kitchen with honed granite countertops and cherry cabinetry. The first-floor primary suite includes a luxurious marble bathroom and secluded home office. On the second floor, an open family room is seamlessly connected to the outdoors with front and back decks, while offering the utmost convenience with a thoughtfully designed kitchenette. Two bedrooms and two bathrooms complete the second floor. Additional highlights include a four-car garage with a self-contained apartment above, a lush backyard, and a large bluestone patio. Mere minutes from everything Osterville has to offer, this extraordinary residence delivers the quintessential Cape Cod lifestyle.

Coastal luxury, a timeless and thoughtful design with a sense of sophistication and comfort in this totally remodeled 2 bed, 2 bath second floor condo in the heart of Osterville village. Steps to shopping and dining and 1 Mile to beach! Spacious living and dining room combination with lots of natural sunlight, adjacent to the newly remodeled kitchen with quartz counters, Kitchen Aid appliances, new cabinetry, undermount lighting, and lots of storage in this darling kitchen. Kick your shoes off and let your feet feel the Sawyer Mason high end flooring throughout the condo. Plantation shutters throughout! Enjoy your wood burning fireplace, or the ample deck to dine and lounge under the awning in the summer. Retreat to the spacious primary bedroom with en-suite bathroom, double vanity and Carrera marble flooring. Gorgeous custom guest bathroom with Thibault wallpaper and walk in shower. Stroll to the village for shopping and dining. Close to the beach! Welcome to your new lifestyle!

Coastal luxury with a sense of sophistication and comfort in this newly renovated condo in the village of Osterville with an In-Town location! Stroll to the restaurants and shops! Dowses Beach a mile away! Spacious living/dining combination with lots of natural sunlight! Gorgeous kitchen with Kitchen Aid appliances, white shaker cabinetry, quartz countertops and gorgeous tile and backsplash. Dreamy and beachy Sawyer Mason hardwood flooring throughout the condo. Two comfy bedrooms with an oversized master with en-suite bathroom with double marble vanity. High end custom bathroom for your guests with Thibault wallpaper! Gorgeous grass cloth in living and dining, recessed lighting, crown molding, plantation shutters, lots of closet space and storage. Wood burning fireplace for the cool nights and a deck to dine in the summer months! Professionally painted. In-unit laundry! Furniture negotiable! Welcome to your new lifestyle!

Charming 2 bedroom, 1.5 bath single family ranch style home situated on a 1/2 acre of park like grounds just inside Osterville village (Gallery Place). The home is situated on a stunning and remarkably private lot surrounded by homes of significantly higher values. This home is in move-in condition with timeless cape cod details, hardwood floors throughout, with generously sized bedrooms, a large living room fireplace and an open concept flow throughout the common areas. It can be enjoyed as a year round residence or a seasonal rental opportunity. Because the lot is so large with ideal dimensions and given its idyllic location within Osterville Village, it can be redesigned, modernized or razed and re-built as new construction. The owner has created 2 septic designs (attached) and will install in the location approved by the buyer. And because the property contains at least 20,000 SF, the home could be used as a legal 3 bedroom with an alternative septic design (fast system).

Charming 2 bedroom, 1.5 bath single family ranch style home situated on a 1/2 acre of park like grounds just inside Osterville village (Gallery Place). The home is situated on a stunning and remarkably private lot surrounded by homes of significantly higher values. This home is in move-in condition with timeless cape cod details, hardwood floors throughout, with generously sized bedrooms, a large living room fireplace and an open concept flow throughout the common areas. It can be enjoyed as a year round residence or a seasonal rental opportunity. Because the lot is so large with ideal dimensions and given its idyllic location within Osterville Village, it can be redesigned, modernized or razed and re-built as new construction. The owner has created 2 septic designs (attached) and will install in the location approved by the buyer. And because the property contains at least 20,000 SF, the home could be used as a legal 3 bedroom with an alternative septic design (fast system).

Location!!! One of the best in Osterville. Just a short stroll to the Village, Wianno Golf Course and North Bay landing to kayak, shellfish or just enjoy the view. This newly renovated 4 bedroom home was meticulously designed with exceptional craftsmanship. The spectacular gourmet kitchen includes top of the line appliances, a generous center island and a cozy fireplace. The primary bedroom with vaulted ceilings and an en suite bathroom, as well as the three additional bedrooms and second floor office/den overlook the professionally landscaped yard with a covered bluestone patio. This home, with its high ceilings, hardwood throughout, marble and natural stone bathrooms, a welcoming farmers porch, and a two car garage is truly a gem right in the heart of Osterville.