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Privately set behind a gated drive on two acres along Eel River, this remarkable Osterville waterfront estate commands a rare vantage point overlooking the river and Nantucket Sound. The architecture is designed around the setting, with broad expanses of glass, soaring coffered ceilings, fine millwork, and a succession of light-filled spaces oriented toward the water. The main level brings together a gracious chef’s kitchen, a dramatic great room overlooking the water, and a luxurious primary suite with its own media room. The residence unfolds across three levels, with a graceful stairway connecting each floor. The second level offers three additional bedroom suites, while the third floor creates a more intimate retreat, with a spacious waterfront sitting room opening to a private balcony, and a fifth bedroom along with two bonus rooms. The finished lower level is dedicated to recreation, with a theater accommodating 20 and a substantial game and media room. Beyond the main residence, the property takes on the character of a private coastal compound. A separate two-bedroom guest house with three-car garage and pool house overlooks the expansive pool and surrounding grounds. Multiple terraces and outdoor rooms lead toward the water, where a private sandy beach and substantial deep-water dock provide direct access to Eel River and Nantucket Sound. The setting is quintessentially Osterville: private, deeply connected to the water, and minutes from the village, its beaches, harbor, shops, and restaurants. With its scale, architectural pedigree, guest accommodations, and exceptional boating access, this is a distinctive waterfront offering in one of Cape Cod’s most sought-after enclaves. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

7 Beds ⋅ 13 Baths ⋅ 73584008 MLS

Privately set behind a gated drive on two acres along Eel River, this remarkable Osterville waterfront estate commands a rare vantage point overlooking the river and Nantucket Sound. The architecture is designed around the setting, with broad expanses of glass, soaring coffered ceilings, fine millwork, and a succession of light-filled spaces oriented toward the water. The main level brings together a gracious chef’s kitchen, a dramatic great room overlooking the water, and a luxurious primary suite with its own media room. The residence unfolds across three levels, with a graceful stairway connecting each floor. The second level offers three additional bedroom suites, while the third floor creates a more intimate retreat, with a spacious waterfront sitting room opening to a private balcony, and a fifth bedroom along with two bonus rooms. The finished lower level is dedicated to recreation, with a theater accommodating 20 and a substantial game and media room. Beyond the main residence, the property takes on the character of a private coastal compound. A separate two-bedroom guest house with three-car garage and pool house overlooks the expansive pool and surrounding grounds. Multiple terraces and outdoor rooms lead toward the water, where a private sandy beach and substantial deep-water dock provide direct access to Eel River and Nantucket Sound. The setting is quintessentially Osterville: private, deeply connected to the water, and minutes from the village, its beaches, harbor, shops, and restaurants. With its scale, architectural pedigree, guest accommodations, and exceptional boating access, this is a distinctive waterfront offering in one of Cape Cod’s most sought-after enclaves. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

74 Garrison Ln, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

$849,900

Set on a wooded half-acre lot in Osterville, this 2-bedroom, 1.5-bath ranch offers comfortable one-level living and a peaceful connection to the outdoors. Hardwood floors and natural light brighten the living spaces, while a large bay window makes the room currently used as an office an inviting place to work or unwind. The kitchen opens to the dining area, and a patio provides a spot to relax beneath the trees. Enjoy the spacious, level backyard with room to garden or gather around a fire. The seller has cleared underbrush from the rear of the lot and obtained a mortgage inspection plan and lot survey while exploring the potential for an ADU; buyers should verify feasibility and permitting with the town. A full basement, storage shed, gas heat, town water, and a paved driveway with parking for three complete the property. Convenient to Osterville’s shops, beaches, golf, and walking trails.

2 Beds ⋅ 2 Baths ⋅ 73582615 MLS

Set on a wooded half-acre lot in Osterville, this 2-bedroom, 1.5-bath ranch offers comfortable one-level living and a peaceful connection to the outdoors. Hardwood floors and natural light brighten the living spaces, while a large bay window makes the room currently used as an office an inviting place to work or unwind. The kitchen opens to the dining area, and a patio provides a spot to relax beneath the trees. Enjoy the spacious, level backyard with room to garden or gather around a fire. The seller has cleared underbrush from the rear of the lot and obtained a mortgage inspection plan and lot survey while exploring the potential for an ADU; buyers should verify feasibility and permitting with the town. A full basement, storage shed, gas heat, town water, and a paved driveway with parking for three complete the property. Convenient to Osterville’s shops, beaches, golf, and walking trails.

466 Old Mill Rd, Barnstable

Listing courtesy of Listing Agent: Danny Griffin from Listing Office: Griffin Realty Group.

$849,900

Attractive and Custom Straight Ranch 42x24 +14x12 +21x17! 1- level living features Fireplaced Living room with bay window / 3rd Bedroom or Study/Office/Den with picture window and closet / Custom Kitchen with contemporary cabinets, peninsula, eat-in area, vinyl flooring and 1/2 wall with oak trim overlooking an incredible 1st Floor Family room with entry to 22x14 deck / Family room features Open beamed cathedral ceiling, skylights / custom windows / raised hearth Fireplace, sliders to an oversized deck / Main Bedroom suite with walk-in closet, laundry and private bathroom / 2nd Bedroom with wall to wall carpeting and coat closet / Hallway with pull-down stairs to attic and access to Full bathroom / Full basement under addition / Partially crawl under main house / Generator fired by natural gas / Title V completed / Fenced yard / This home is unique with an Open Floor plan! Close to stores and conveniences,

2 Beds ⋅ 2 Baths ⋅ 73581180 MLS

Attractive and Custom Straight Ranch 42x24 +14x12 +21x17! 1- level living features Fireplaced Living room with bay window / 3rd Bedroom or Study/Office/Den with picture window and closet / Custom Kitchen with contemporary cabinets, peninsula, eat-in area, vinyl flooring and 1/2 wall with oak trim overlooking an incredible 1st Floor Family room with entry to 22x14 deck / Family room features Open beamed cathedral ceiling, skylights / custom windows / raised hearth Fireplace, sliders to an oversized deck / Main Bedroom suite with walk-in closet, laundry and private bathroom / 2nd Bedroom with wall to wall carpeting and coat closet / Hallway with pull-down stairs to attic and access to Full bathroom / Full basement under addition / Partially crawl under main house / Generator fired by natural gas / Title V completed / Fenced yard / This home is unique with an Open Floor plan! Close to stores and conveniences,

87 Hinckley Circle, Barnstable

Listing courtesy of Listing Agent: George Raymond from Listing Office: Raymond & Son REALTORS®.

$2,825,000

Perfectly situated within a 5-minute drive of the beach, Main Street Osterville shopping and restaurants, and Route 28, which opens all of the Cape to exploration and fun, this gracious 4-bed, 4-bath home offers a peaceful retreat where timeless coastal charm meets effortless outdoor living. Set among mature trees and beautifully groomed landscaping, the wooded setting creates privacy and a sense of escape, while the inviting deck and three-season screened porch extend the living space into nature. Inside, glowing hardwood floors and abundant windows fill the home with warmth and natural light. Soaring ceilings and beautiful exposed beams add a sense of grandeur, while multiple fireplaces, framed by timeless brick and distinctive wood mantels, create cozy gathering spaces throughout. The expansive kitchen shines with polished granite countertops, bright white cabinetry, stainless steel appliances, including a double oven and gas range, blending beautifully with the home’s classic character.And every bathroom is truly amazing, with beautiful finishes and a polished, inviting feel. The extraordinary primary bedroom is a true sanctuary, with abundant windows creating an atmosphere that feels both grand and intimate. The spa-like primary bath features a dual vanity, separate garden tub, and beautiful finishes, offering a serene place to begin and end the day. Outside, a paver patio surrounds the sparkling swimming pool and outdoor BBQ, creating a private setting made for long sunny afternoons and evenings gathered with friends. Add to this the huge, partially finished basement and garage to provide abundant storage and flexibility. A home where sunlight, greenery, and Cape Cod ease come together beautifully. Come view today!

4 Beds ⋅ 4 Baths ⋅ 73577150 MLS

Perfectly situated within a 5-minute drive of the beach, Main Street Osterville shopping and restaurants, and Route 28, which opens all of the Cape to exploration and fun, this gracious 4-bed, 4-bath home offers a peaceful retreat where timeless coastal charm meets effortless outdoor living. Set among mature trees and beautifully groomed landscaping, the wooded setting creates privacy and a sense of escape, while the inviting deck and three-season screened porch extend the living space into nature. Inside, glowing hardwood floors and abundant windows fill the home with warmth and natural light. Soaring ceilings and beautiful exposed beams add a sense of grandeur, while multiple fireplaces, framed by timeless brick and distinctive wood mantels, create cozy gathering spaces throughout. The expansive kitchen shines with polished granite countertops, bright white cabinetry, stainless steel appliances, including a double oven and gas range, blending beautifully with the home’s classic character.And every bathroom is truly amazing, with beautiful finishes and a polished, inviting feel. The extraordinary primary bedroom is a true sanctuary, with abundant windows creating an atmosphere that feels both grand and intimate. The spa-like primary bath features a dual vanity, separate garden tub, and beautiful finishes, offering a serene place to begin and end the day. Outside, a paver patio surrounds the sparkling swimming pool and outdoor BBQ, creating a private setting made for long sunny afternoons and evenings gathered with friends. Add to this the huge, partially finished basement and garage to provide abundant storage and flexibility. A home where sunlight, greenery, and Cape Cod ease come together beautifully. Come view today!

55 Seapuit Rd, Barnstable

Listing courtesy of Listing Agent: Danny Griffin from Listing Office: Griffin Realty Group.

$1,485,000

Beautifully renovated, 23 & 27 Swift Avenue is a rare two-parcel Osterville offering totaling approximately 1.11 acres, moments from Osterville Village. The charming 3-bedroom residence sits on approximately .66 acre and is conveyed with an adjoining approximately .45-acre parcel, creating exceptional privacy and intriguing future potential. Recent improvements include a new roof and brand-new 4-bedroom septic system. Sun-filled interiors feature warm wood floors, classic Cape character and a beautifully appointed kitchen flowing to the dining and family areas. A first-floor primary suite with renovated bath, separate living room and powder room complete the main level, with two bedrooms and full bath upstairs. Outdoors, enjoy expansive lawns, mature landscaping, oversized spa, outdoor shower and stone fire pit. A detached 2-car garage offers temperature/humidity controls and epoxy flooring. Additional parcel offers future possibilities, subject to approvals.

3 Beds ⋅ 3 Baths ⋅ 73571845 MLS

Beautifully renovated, 23 & 27 Swift Avenue is a rare two-parcel Osterville offering totaling approximately 1.11 acres, moments from Osterville Village. The charming 3-bedroom residence sits on approximately .66 acre and is conveyed with an adjoining approximately .45-acre parcel, creating exceptional privacy and intriguing future potential. Recent improvements include a new roof and brand-new 4-bedroom septic system. Sun-filled interiors feature warm wood floors, classic Cape character and a beautifully appointed kitchen flowing to the dining and family areas. A first-floor primary suite with renovated bath, separate living room and powder room complete the main level, with two bedrooms and full bath upstairs. Outdoors, enjoy expansive lawns, mature landscaping, oversized spa, outdoor shower and stone fire pit. A detached 2-car garage offers temperature/humidity controls and epoxy flooring. Additional parcel offers future possibilities, subject to approvals.

23-27 Swift Ave, Barnstable

Listing courtesy of Listing Agent: Livia Freitas Monteforte from Listing Office: Compass.

$999,000

LIKE-NEW IN OSTERVILLE’S COVETED WIANNO AREA! Rare opportunity to own a free-standing condo/golf villa offering effortless luxury and low-maintenance Cape Cod living. Built in 2023 and lightly lived in, this beautifully appointed home is moments from Osterville Village, Wianno Golf Club, Dowses Beach, marinas, shops and dining. The light-filled interior features soaring ceilings, hardwood floors and a gas fireplace. An oversized gourmet kitchen showcases upgraded countertops, Bosch appliances and custom finishes. Two spacious bedrooms, 2.5 baths, plus separate living and family rooms offer exceptional flexibility. The serene primary suite features a spa-like bath. Large sliders open to an expansive fenced private patio with outdoor shower. HERS 53 energy rating, Navien on-demand hot water and central vacuum complete this Osterville retreat.

2 Beds ⋅ 3 Baths ⋅ 73571682 MLS

LIKE-NEW IN OSTERVILLE’S COVETED WIANNO AREA! Rare opportunity to own a free-standing condo/golf villa offering effortless luxury and low-maintenance Cape Cod living. Built in 2023 and lightly lived in, this beautifully appointed home is moments from Osterville Village, Wianno Golf Club, Dowses Beach, marinas, shops and dining. The light-filled interior features soaring ceilings, hardwood floors and a gas fireplace. An oversized gourmet kitchen showcases upgraded countertops, Bosch appliances and custom finishes. Two spacious bedrooms, 2.5 baths, plus separate living and family rooms offer exceptional flexibility. The serene primary suite features a spa-like bath. Large sliders open to an expansive fenced private patio with outdoor shower. HERS 53 energy rating, Navien on-demand hot water and central vacuum complete this Osterville retreat.

16 Second Unit 4, Barnstable

Listing courtesy of Listing Agent: Livia Freitas Monteforte from Listing Office: Compass.

$1,299,900

Set in desirable Osterville, 30 Deerfield Road is a beautifully reimagined three-bedroom, three-bath residence offering effortless coastal living just minutes from the beach. Recently transformed through a comprehensive interior and exterior renovation, the home blends timeless Cape Cod character with fresh, sophisticated finishes and modern comfort. The thoughtfully designed layout is highlighted by a desirable first-floor primary suite, complete with direct access to a private screened-in porch, an inviting retreat for morning coffee or relaxed summer evenings. At the heart of the home, an entirely new kitchen opens to the main living space, with a quartz-topped island and counter seating, an induction range, a beverage fridge, and an unlacquered brass faucet set at a window overlooking the yard. Generous open living and entertaining spaces flow seamlessly to the outdoors, where a spacious deck, paver patio, and classic outdoor shower create the perfect setting for life by the coast. Upstairs, two well-appointed bedrooms are joined by a versatile bonus room, ideal as a guest space or home office, along with a large full bath and a dedicated laundry room. An attached two-car garage and driveway provide ample parking, while the full walkout basement offers extra storage and the potential to be finished in the future for additional space. All of the major systems are new as well, including a natural gas Navien HydroAir boiler with on-demand tankless hot water, brand new central AC, plumbing, and updated 200-amp electrical. Exterior updates include a new asphalt roof, updated siding and trim, and select new windows and doors. With multiple indoor-outdoor living spaces, the home is equally suited for year-round living, weekend escapes, or memorable summers with family and friends. Ideally located just a few minutes from both Dowse's and Craigville beaches and within easy reach of Osterville Village, this turnkey property captures the relaxed elegance and lifestyle that make Cape Cod so special.

3 Beds ⋅ 3 Baths ⋅ 73571509 MLS

Set in desirable Osterville, 30 Deerfield Road is a beautifully reimagined three-bedroom, three-bath residence offering effortless coastal living just minutes from the beach. Recently transformed through a comprehensive interior and exterior renovation, the home blends timeless Cape Cod character with fresh, sophisticated finishes and modern comfort. The thoughtfully designed layout is highlighted by a desirable first-floor primary suite, complete with direct access to a private screened-in porch, an inviting retreat for morning coffee or relaxed summer evenings. At the heart of the home, an entirely new kitchen opens to the main living space, with a quartz-topped island and counter seating, an induction range, a beverage fridge, and an unlacquered brass faucet set at a window overlooking the yard. Generous open living and entertaining spaces flow seamlessly to the outdoors, where a spacious deck, paver patio, and classic outdoor shower create the perfect setting for life by the coast. Upstairs, two well-appointed bedrooms are joined by a versatile bonus room, ideal as a guest space or home office, along with a large full bath and a dedicated laundry room. An attached two-car garage and driveway provide ample parking, while the full walkout basement offers extra storage and the potential to be finished in the future for additional space. All of the major systems are new as well, including a natural gas Navien HydroAir boiler with on-demand tankless hot water, brand new central AC, plumbing, and updated 200-amp electrical. Exterior updates include a new asphalt roof, updated siding and trim, and select new windows and doors. With multiple indoor-outdoor living spaces, the home is equally suited for year-round living, weekend escapes, or memorable summers with family and friends. Ideally located just a few minutes from both Dowse's and Craigville beaches and within easy reach of Osterville Village, this turnkey property captures the relaxed elegance and lifestyle that make Cape Cod so special.

30 Deerfield Rd, Barnstable

Listing courtesy of Listing Agent: Garrett Hogan from Listing Office: Garland Group, LLC.

$1,100,000

Back on Market! Opportunity awaits in this coveted Osterville neighborhood. Bring Your Vision to Life With Over 3300 Sq Ft of Living Space. Radiating curb appeal, this home has been lovingly maintained by the same owners since it was built nearly 50 years ago. Set on a double lot, the mature landscaping shines in every season! New central AC, Generator, irrigation, a shed, composite deck and two car garage. Inside, the welcoming main entry leads to a spacious sitting room with bay window, opening into an elegant dining room. The bright kitchen features a skylight, peninsula and wet bar and opens into the living room with beamed ceilings, fireplace and built-in bookshelf. A highlight of the living space is a sun room with vaulted ceiling and window seat. A separate wing of the main floor has 3 bedrooms and 2 full bathrooms. The main level is rounded out by a third full bathroom and laundry closet. Upstairs, there is a massive private suite with full bathroom and its own office. The dry, unfinished basement has potential for adding extra living space. All this in a private neighborhood minutes from Osterville Village.

4 Beds ⋅ 4 Baths ⋅ 73546631 MLS

Back on Market! Opportunity awaits in this coveted Osterville neighborhood. Bring Your Vision to Life With Over 3300 Sq Ft of Living Space. Radiating curb appeal, this home has been lovingly maintained by the same owners since it was built nearly 50 years ago. Set on a double lot, the mature landscaping shines in every season! New central AC, Generator, irrigation, a shed, composite deck and two car garage. Inside, the welcoming main entry leads to a spacious sitting room with bay window, opening into an elegant dining room. The bright kitchen features a skylight, peninsula and wet bar and opens into the living room with beamed ceilings, fireplace and built-in bookshelf. A highlight of the living space is a sun room with vaulted ceiling and window seat. A separate wing of the main floor has 3 bedrooms and 2 full bathrooms. The main level is rounded out by a third full bathroom and laundry closet. Upstairs, there is a massive private suite with full bathroom and its own office. The dry, unfinished basement has potential for adding extra living space. All this in a private neighborhood minutes from Osterville Village.

175 Hickory Hill Circle, Barnstable

Listing courtesy of Listing Agent: Michelle Curran from Listing Office: Coastal Real Estate Advisors, LLC.

$4,795,000

Welcome to the beautiful village of Osterville on Cape Cod located in the heart of town, close to many stores & restaurants & only 1 mile to Dowses Beach. This newly built home was custom designed by Barnstable Harbor Builders including many high end features such as: quartz counters, Thermador appliances, red oak HW floors & custom trim detail, beadboard ceilings, & crown molding. The home is positioned seamlessly on a large .52 acre lot with a spacious back yard, a brand new vinyl saltwater pool, outdoor shower, a screened in porch, large patio area, & an outdoor pool cabana w/ a bathroom. This home is perfect for those special summer nights on Cape Cod sitting by the pool and relaxing. Each bedroom includes it's own full bathroom including the 1st floor primary suite bedroom. A few other features added by the builder: a whole house generator, gas fireplace, irrigation system, & a 1-year builder warranty as well. Come see your dream home today before it's too late!

5 Beds ⋅ 7 Baths ⋅ 73542127 MLS

Welcome to the beautiful village of Osterville on Cape Cod located in the heart of town, close to many stores & restaurants & only 1 mile to Dowses Beach. This newly built home was custom designed by Barnstable Harbor Builders including many high end features such as: quartz counters, Thermador appliances, red oak HW floors & custom trim detail, beadboard ceilings, & crown molding. The home is positioned seamlessly on a large .52 acre lot with a spacious back yard, a brand new vinyl saltwater pool, outdoor shower, a screened in porch, large patio area, & an outdoor pool cabana w/ a bathroom. This home is perfect for those special summer nights on Cape Cod sitting by the pool and relaxing. Each bedroom includes it's own full bathroom including the 1st floor primary suite bedroom. A few other features added by the builder: a whole house generator, gas fireplace, irrigation system, & a 1-year builder warranty as well. Come see your dream home today before it's too late!

22 Scudder Road, Barnstable

Listing courtesy of Listing Agent: The Quirk Group from Listing Office: Coldwell Banker Realty - Boston.

$7,500,000

Nestled along the sparkling shores of North Bay in the heart of Osterville, this exceptional Waterfront Estate delivers timeless beauty and relaxed elegance. Wake each morning to sweeping water views and ocean breezes, step onto your boat from the Substantial Dock. Featuring a Primary Suite and Guest Suite both on the 1st Floor, the residence is thoughtfully designed to blend coastal charm with modern comfort, with sun-filled living spaces, expansive windows, and seamless indoor-outdoor flow perfect for entertaining or quiet seaside relaxation. Waterfront Chef's Kitchen with Cathedral Ceiling, Living Rooms, Dens, separate living quarters complete with a Kitchen over the 3-Bay Garage. Step outside to your private waterfront oasis, where launching a kayak at sunrise, enjoying afternoon boating on North Bay, or taking sunset walks with the dog, every day feels like a vacation. Located just moments from Osterville Village's boutiques, restaurants, and marinas.

3 Beds ⋅ 6 Baths ⋅ 73520995 MLS

Nestled along the sparkling shores of North Bay in the heart of Osterville, this exceptional Waterfront Estate delivers timeless beauty and relaxed elegance. Wake each morning to sweeping water views and ocean breezes, step onto your boat from the Substantial Dock. Featuring a Primary Suite and Guest Suite both on the 1st Floor, the residence is thoughtfully designed to blend coastal charm with modern comfort, with sun-filled living spaces, expansive windows, and seamless indoor-outdoor flow perfect for entertaining or quiet seaside relaxation. Waterfront Chef's Kitchen with Cathedral Ceiling, Living Rooms, Dens, separate living quarters complete with a Kitchen over the 3-Bay Garage. Step outside to your private waterfront oasis, where launching a kayak at sunrise, enjoying afternoon boating on North Bay, or taking sunset walks with the dog, every day feels like a vacation. Located just moments from Osterville Village's boutiques, restaurants, and marinas.

46 Great Bay Rd, Barnstable

Listing courtesy of Listing Agent: Chuck Tuttle from Listing Office: William Raveis R.E. & Home Services.

$634,900

Incredible value at this new price in Osterville Heights! Move right into this sun-filled open-concept ranch with one-car garage and oversized shed, a private and spacious partially-fenced backyard with its park-like setting is perfect for adding a potential pool, enjoying outdoor games, barbecues, and relaxing with family and friends. New improvements include enhanced landscaping, fresh paint, Canadian white oak flooring throughout, three Rovsun mini-split A/C units, tile floors in both bathrooms, an Electrolux non-venting stackable washer/dryer in hallway full bath, vanity/toilet in second bedroom bath, and an electric heated fireplace in large bedroom. The full lower level as well as the generous backyard provides more options for additional living space. Perfectly suited as a year-round residence, vacation getaway or investment opportunity. Ideally located just minutes from Osterville Village, Dowses Beach, golf, boating, shopping, dining and many other premier local amenities!

2 Beds ⋅ 2 Baths ⋅ 73513515 MLS

Incredible value at this new price in Osterville Heights! Move right into this sun-filled open-concept ranch with one-car garage and oversized shed, a private and spacious partially-fenced backyard with its park-like setting is perfect for adding a potential pool, enjoying outdoor games, barbecues, and relaxing with family and friends. New improvements include enhanced landscaping, fresh paint, Canadian white oak flooring throughout, three Rovsun mini-split A/C units, tile floors in both bathrooms, an Electrolux non-venting stackable washer/dryer in hallway full bath, vanity/toilet in second bedroom bath, and an electric heated fireplace in large bedroom. The full lower level as well as the generous backyard provides more options for additional living space. Perfectly suited as a year-round residence, vacation getaway or investment opportunity. Ideally located just minutes from Osterville Village, Dowses Beach, golf, boating, shopping, dining and many other premier local amenities!

55 Seth Goodspeed's Way, Barnstable

Listing courtesy of Listing Agent: Donna Christopher from Listing Office: Sotheby's International Realty.

$2,950,000

Located in the heart of Osterville - one of Cape Cod's most desirable seaside villages along Nantucket Sound - 12 Cockachoiset, known as the iconic ''Windmill House,'' offers a distinctive blend of coastal charm and architectural character. Recognized for its unique two-story windmill adorned with seaside murals, the home features a balcony with water views and serves as a memorable focal point of this special property. The main living spaces are designed for comfort and gathering, highlighted by a generous great room with a custom fireplace that opens to a covered patio and private side yard. A well-appointed kitchen adjoins the dining room, while the first floor also includes a bedroom with attached sitting room, laundry, and multiple inviting outdoor living areas. Upstairs, the primary suite is anchored by its own fireplace, private bath, and walk-in closet. An additional sitting room with balcony access and a third bedroom complete the second level, offering flexible space for guests and relaxation. Ideally located just moments from Osterville Village, this property enjoys close proximity to boutiques, dining, and nearby beaches, while also being near some of the area's most renowned marinas, including Nauticus Marina, Crosby Yacht Yard, and Oyster Harbors Marine - offering convenient access to premier boating and waterfront amenities. The adjacent property at 30 Cockachoiset Lane is also available for sale (MLS 22601972). Together, the properties offer a rare opportunity to create a side-by-side coastal compound, with a demonstrated history of significantly strong, high-value rentals and private gatherings. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

3 Beds ⋅ 3 Baths ⋅ 73513191 MLS

Located in the heart of Osterville - one of Cape Cod's most desirable seaside villages along Nantucket Sound - 12 Cockachoiset, known as the iconic ''Windmill House,'' offers a distinctive blend of coastal charm and architectural character. Recognized for its unique two-story windmill adorned with seaside murals, the home features a balcony with water views and serves as a memorable focal point of this special property. The main living spaces are designed for comfort and gathering, highlighted by a generous great room with a custom fireplace that opens to a covered patio and private side yard. A well-appointed kitchen adjoins the dining room, while the first floor also includes a bedroom with attached sitting room, laundry, and multiple inviting outdoor living areas. Upstairs, the primary suite is anchored by its own fireplace, private bath, and walk-in closet. An additional sitting room with balcony access and a third bedroom complete the second level, offering flexible space for guests and relaxation. Ideally located just moments from Osterville Village, this property enjoys close proximity to boutiques, dining, and nearby beaches, while also being near some of the area's most renowned marinas, including Nauticus Marina, Crosby Yacht Yard, and Oyster Harbors Marine - offering convenient access to premier boating and waterfront amenities. The adjacent property at 30 Cockachoiset Lane is also available for sale (MLS 22601972). Together, the properties offer a rare opportunity to create a side-by-side coastal compound, with a demonstrated history of significantly strong, high-value rentals and private gatherings. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

12 Cockachoiset Lane, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

81 Osterville-West Barnstable Rd, Barnstable

$1,750,000

This elegant Cape-style residence offers a refined retreat on a sprawling, wooded lot near Osterville Village and Dowses Beach. Defined by bright, voluminous spaces, the home features a stately pillared portico, stone walkways, and classic shingle siding. Inside, the center hall layout leads to a grand living room with a two-story wall of windows and a Palladian arch. This flows into the dining room and a kitchen equipped with granite countertops, a cooktop island, and a sunny breakfast nook. The adjacent family room features custom built-ins and a brick fireplace. The first-flow primary suite serves as a sanctuary with a walk-in closet and en suite bathroom. Upstairs, a mezzanine gallery overlooks the living area, leading to two spacious guest bedrooms. Outside, an expansive rear deck with a vine-covered pergola overlooks the private lawn and an ornamental pond, creating the perfect setting for relaxation. Located minutes from everything Osterville has to offer!

3 Beds ⋅ 3 Baths ⋅ 73512219 MLS

This elegant Cape-style residence offers a refined retreat on a sprawling, wooded lot near Osterville Village and Dowses Beach. Defined by bright, voluminous spaces, the home features a stately pillared portico, stone walkways, and classic shingle siding. Inside, the center hall layout leads to a grand living room with a two-story wall of windows and a Palladian arch. This flows into the dining room and a kitchen equipped with granite countertops, a cooktop island, and a sunny breakfast nook. The adjacent family room features custom built-ins and a brick fireplace. The first-flow primary suite serves as a sanctuary with a walk-in closet and en suite bathroom. Upstairs, a mezzanine gallery overlooks the living area, leading to two spacious guest bedrooms. Outside, an expansive rear deck with a vine-covered pergola overlooks the private lawn and an ornamental pond, creating the perfect setting for relaxation. Located minutes from everything Osterville has to offer!

81 Osterville-West Barnstable Rd, Barnstable

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .

$735,000

This is the Osterville opportunity you’ve been waiting for. A sprawling 1.4 acre lot that borders conservation land, this is a canvas for your Cape Cod vision. You’re just moments from the heart of Osterville’s iconic village center, where you can spend afternoons browsing boutique shops or enjoying delightful dining at one of the local eateries. When the sun is shining, the pristine sands of Dowses Beach are just a short distance away.Whether you’re looking to breathe new life into the existing home through a thoughtful renovation or you're ready to start fresh and build a custom retreat that fully captures the potential of this expansive lot, the possibilities here are endless. Bring your imagination and discover the chance to create something truly special in one of the Cape’s most coveted communities.

2 Beds ⋅ 2 Baths ⋅ 73503938 MLS

This is the Osterville opportunity you’ve been waiting for. A sprawling 1.4 acre lot that borders conservation land, this is a canvas for your Cape Cod vision. You’re just moments from the heart of Osterville’s iconic village center, where you can spend afternoons browsing boutique shops or enjoying delightful dining at one of the local eateries. When the sun is shining, the pristine sands of Dowses Beach are just a short distance away.Whether you’re looking to breathe new life into the existing home through a thoughtful renovation or you're ready to start fresh and build a custom retreat that fully captures the potential of this expansive lot, the possibilities here are endless. Bring your imagination and discover the chance to create something truly special in one of the Cape’s most coveted communities.

441 Old Mill Rd, Barnstable

Listing courtesy of Listing Agent: Diane Boudreau from Listing Office: Kinlin Grover Compass.