Osterville Homes

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  /69

  $7,950,000

  • 8 Beds
  • 9 Baths
  • 7,350 Sq Ft

  850 Sea View Ave, Osterville, MA 02655

  At the western end of Osterville's legendary Sea View Avenue--a road many believe is one of the most beautiful and valuable on all of Cape Cod reveals a property that transcends the idea of a residence. On over one acre of sweeping, tree-lined greensward with glimpses of West Bay shimmering in the distance, here is a residence that is not simply lived in, but experienced.Accessed by a winding

  

  John Cotton

  Sotheby's International Realty

  (508) 504-1820

  850 Sea View Ave, Osterville, MA 02655
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  Explore Osterville

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  /23

  $3,900 per month plus fees

  • 3 Beds
  • 2 Baths
  • 1,339 Sq Ft
  • House for Rent

  21 Oak Ln, Osterville, MA 02655

  This recently renovated Cape-style home at 21 Oak Lane in Osterville offers stylish, turnkey living just minutes from beaches, shops, and village amenities. The home is being offered fully furnished. The home features three bedrooms, two full bathrooms, including a spacious primary suite with a marble bath. The open-concept living area boasts vaulted ceilings and hardwood floors throughout,

  

  Kerry Houde

  Lamacchia Realty, Inc.

  (508) 466-5286

  21 Oak Ln, Osterville, MA 02655
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  /34

  $1,220,000 Sold Sep 03, 2025

  • 3,226 Sq Ft
  • $378/SF
  • 164 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1989

  120 Robbins St, Osterville, MA 02655

  120 Robbins has great curb appeal but what is truly amazing is the interior and all the surprises it holds for the discerning buyer....not only do we have a wonderful open floor plan filled with sunshine we have doors that open to rooms you did not expect. The four season porch is a fabulous bonus which opens to beautiful landscaping and decks. There is a bonus room adjacent to the primary

  Joan Witter Compass Massachusetts, LLC

  120 Robbins St, Osterville, MA 02655
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  /26

  Est $6,234,506 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 7,126 Sq Ft

  473 Grand Island Dr, Osterville, MA 02655

  473 Grand Island Dr, Osterville, MA 02655
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  /40

  $1,700,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,050 Sq Ft

  72 Hathaway Rd, Osterville, MA 02655

  Did you ever have a treehouse? Standing on the deck of this amazing Wianno retreat, we had that ''tree house feeling.'' Our first thoughts were, silence, privacy, safety and security. All the craziness everywhere in the world was far away. Gone, in fact. Welcome to 72 Hathaway Road in the Wianno section of Osterville. When you walk through the entrance, you can feel the warmth of sixty-plus years

  

  John Cotton

  Sotheby's International Realty

  (508) 979-6232

  72 Hathaway Rd, Osterville, MA 02655
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  /18

  $2,500 per month plus fees

  • 2 Beds
  • 2 Baths
  • 1,170 Sq Ft
  • Townhouse for Rent

  13 South St, Osterville, MA 02655

  Immaculate totally furnished winter rental with private deck, private access, and parking. WINTER RENTAL ONLY: Available to March 30... possibly a little longer. Maximum 2 people. NO SMOKING.NO PETS. Shorter term furnished rental possible, but prefer a 6 month minimum. Rate is for rentals over 3 months. Located in the heart of Osterville village is this quaint renovated Townhome (1/2 Duplex)

  

  Marie Souza

  Cape Cod Real Estate Services

  (508) 419-9458

  13 South St, Osterville, MA 02655
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  /70

  $5,600,000 Sold Sep 02, 2025

  • 6,565 Sq Ft
  • $853/SF
  • 16 Days On Market

  • 6 Beds
  • 7.5 Baths
  • Built 2011

  195 Bunker Hill Rd, Osterville, MA 02655

  The beginning of every day sets the tone for that day. And here, at 195 Bunker Hill Road in the Seapuit section of Osterville, each morning arrives with quiet grandeur setting a high bar for the day.Imagine waking to sweeping views of lush, manicured greensward, the rustle of trees whispering in the breeze and the gentle hush of absolute privacy. It's the kind of beginning that makes you feel

  John Cotton Sotheby's International Realty

  195 Bunker Hill Rd, Osterville, MA 02655
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  /9

  Est $2,349,997 Not Listed For Sale

  48 Starboard Ln, Osterville, MA 02655

  48 Starboard Ln, Osterville, MA 02655
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  /50

  $15,000,000

  • 6 Beds
  • 7 Baths
  • 6,830 Sq Ft

  391 Sea View Ave, Osterville, MA 02655

  Overlooking the shimmering waters of Nantucket Sound, this extraordinary Wianno estate offers an unparalleled blend of elegance, privacy, and coastal charm. With its own private sandy beach and panoramic ocean views, this is a rare opportunity to own a legacy property, along Sea View Avenue, in one of Cape Cod's most coveted enclaves. Surrounded by lush, professionally landscaped gardens, the

  Gene Orloff Sotheby's International Realty

  391 Sea View Ave, Osterville, MA 02655
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  /46

  $2,500 per month plus fees

  • 3 Beds
  • 2.5 Baths
  • 1,132 Sq Ft
  • House for Rent

  20 Brigantine Ave, Osterville, MA 02655

  Osterville Summer Rental! $2500/week OR minimum of three-night stay; please call for nightly and off-season rates!This Osterville home is uniquely styled with fine furnishings and touches, tastefully bringing together an aesthetic of Cape Cod with a little Art Deco. Stepping inside your home away from home, you're greeted by rich plantings and soothing color, for that feeling of ''ahhhh.'' Now

  Marina Davalos Sotheby's International Realty

  20 Brigantine Ave, Osterville, MA 02655
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  /60

  $1,505,000 Sold Aug 29, 2025

  • 2,443 Sq Ft
  • $616/SF
  • 49 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1930

  117 Parker Rd, Osterville, MA 02655

  This charming Gambrel in Osterville Village will leave you speechless! Overlooking the 7th hole of the prestigious Wianno Golf Course and a walk to the village, this elegant home offers 2,443 sq ft of flexible living space, featuring rich wood floors, beautiful wainscoting and spacious rooms. The first floor includes a generous living room with fireplace, a dining room or den, a kitchen with

  Patty Flynn William Raveis Real Estate & Home Services

  117 Parker Rd, Osterville, MA 02655
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  /49

  Est $1,315,094 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,163 Sq Ft

  15 Sturbridge Dr, Osterville, MA 02655

  15 Sturbridge Dr, Osterville, MA 02655
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  /36

  $6,495,000

  • 6 Beds
  • 6 Baths
  • 4,021 Sq Ft

  439 Sea View Ave, Osterville, MA 02655

  Presenting the quintessential Cape Cod beach home on sought-after Sea View Avenue. This classic waterfront residence enjoys unobstructed views of Nantucket Sound with a picture-perfect sandy beach. The six-bedroom home showcases Old World craftsmanship and original period details throughout, including wide heart pine plank floors and paneling. At the heart of the home, a spacious living room with

  Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

  439 Sea View Ave, Osterville, MA 02655
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  /29

  $1,075,000 Sold Aug 21, 2025

  • 1,440 Sq Ft
  • $747/SF
  • 82 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1955

  25 Milne Rd, Osterville, MA 02655

  Welcome to this beautifully renovated 3- bedroom, 1.5-bathroom home that blends modern elegance with timeless comfort. The heart of the home is a stunning kitchen featuring a large, custom quartz island, perfect for meal prep, entertaining, and casual dining; new sleek cabinetry and French doors that seamlessly open to a large patio- perfect for indoor/outdoor living and entertaining. The

  Tom Foley The Foley Company

  25 Milne Rd, Osterville, MA 02655
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  /46

  Est $1,301,851 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,458 Sq Ft

  200 Sturbridge Dr, Osterville, MA 02655

  200 Sturbridge Dr, Osterville, MA 02655
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  /40

  $3,999,999

  • 10 Beds
  • 7.5 Baths
  • 6,905 Sq Ft

  414 Eel River Rd, Osterville, MA 02655

  Located in the desirable Wianno in Osterville surrounded by Luxurious homes, and walking distance to Wianno Golf course. This home has plenty of space for a large family or someone who likes to entertain. Home has three separate wings for privacy. Some of the recent improvements include kitchen with open concept. Kitchen has two stainless refrigerators and two dishwashers. Quartz countertops, and

  Shane Pacheco SMP Realty Development Co. LLC

  414 Eel River Rd, Osterville, MA 02655
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  /37

  $807,150 Sold Aug 15, 2025

  • 1,934 Sq Ft
  • $417/SF
  • 21 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1958

  26 Hinckley Cir, Osterville, MA 02655

  Rare opportunity in the heart of Osterville Village! This spacious 3-bedroom ranch with a fully finished lower-level apartment offers strong income potential in a prime, walk-to-town location. The main level features gleaming wood floors, a white kitchen with black granite countertops, large living and dining areas, and a flexible breezeway space. A garage and separate gym room (accessed via

  virginia guimond William Raveis Real Estate & Home Services

  26 Hinckley Cir, Osterville, MA 02655
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  /34

  Est $939,737 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,630 Sq Ft

  203 Sturbridge Dr, Osterville, MA 02655

  203 Sturbridge Dr, Osterville, MA 02655
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  /12

  $3,495,000

  • 4 Beds
  • 5 Baths
  • 2,812 Sq Ft

  64 Bay St, Osterville, MA 02655

  Designed by renowned architect Ivan Bereznicki for personal use, this elegant gambrel residence is just steps from vibrant Osterville Village. Positioned to capture natural light and meadow views, the home plays on architectural scale and heritage with high ceilings, oversized classical columns, and floor-to-ceiling windows. The main level features a sleek chef's kitchen with Miele and Viking

  Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

  64 Bay St, Osterville, MA 02655
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  /73

  $4,200,000 Sold Aug 08, 2025

  • 4,375 Sq Ft
  • $960/SF
  • 16 Days On Market

  • 7 Beds
  • 5.5 Baths
  • Built 1890

  281 Wianno Ave, Osterville, MA 02655

  Welcome to your dream home nestled in the highly sought-after Wianno area, where coastal charm meets modern luxury. This exquisite property features a main house and a carriage house, offering a total of 7 spacious bedrooms & 5.5 bathrooms, perfect for accommodating family and friends or hosting guests in style. As you step inside the main residence, you'll be greeted by an open-concept layout

  John Hopkins Frank A Sullivan Real Estate

  281 Wianno Ave, Osterville, MA 02655
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  /40

  Est $1,586,194 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,795 Sq Ft

  60 Deerfield Rd, Osterville, MA 02655

  60 Deerfield Rd, Osterville, MA 02655
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  /43

  $10,500,000

  • 5 Beds
  • 5 Baths
  • 3,087 Sq Ft

  14 Indian Trail, Barnstable, MA 02630

  Legacy, Lifestyle & Opportunity - A discreet treasure in one of Cape Cod's most prestigious enclaves, this exceptional waterfront property offers rare access to legacy, lifestyle, and limitless potential. Originally part of a historic compound long held by the Mellon family and now by noted philanthropist and collector William Koch, the property stands as a rare opportunity to own a slice of

  Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

  14 Indian Trail, Barnstable, MA 02630
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  /47

  $1,550,000 Sold Jul 18, 2025

  • 2,215 Sq Ft
  • $700/SF
  • 4 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1990

  59 Robbins St, Osterville, MA 02655

  Charming Osterville Retreat - Spacious, Renovated & Steps to Village and Beach. Tucked just off Main Street in the heart of the picturesque village of Osterville, this beautifully renovated Cape Cod home offers the perfect blend of charm, comfort, and convenience. With over 2,200 square feet of living space, this home is deceptively spacious and thoughtfully updated throughout. The heart of the

  Deb Kenney Berkshire Hathaway HomeServices Robert Paul Properties

  59 Robbins St, Osterville, MA 02655
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  /56

  Est $2,665,856 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 3,907 Sq Ft

  379 Starboard Ln, Osterville, MA 02655

  379 Starboard Ln, Osterville, MA 02655
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  /42

  $7,750,000

  • 7 Beds
  • 11 Baths
  • 11,546 Sq Ft

  440 Grand Island Dr, Osterville, MA 02655

  Privately sited within the prestigious Oyster Harbors golf enclave, this extraordinary estate is a masterclass in architectural sophistication and resort-style living. Encompassing a 10,000-square-foot main residence, a stunning 2-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. Inside, refined architectural detail

  Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

  440 Grand Island Dr, Osterville, MA 02655
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  /43

  $3,375,000 Sold Jul 15, 2025

  • 5,421 Sq Ft
  • $623/SF
  • 44 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2002

  320 Parker Rd, Osterville, MA 02655

  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

  Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

  320 Parker Rd, Osterville, MA 02655
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  /39

  Est $3,231,084 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,017 Sq Ft

  175 Starboard Ln, Osterville, MA 02655

  175 Starboard Ln, Osterville, MA 02655
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  /45

  $2,750,000

  • 3 Beds
  • 2 Baths
  • 1,194 Sq Ft

  51 Wianno Cir, Osterville, MA 02655

  Tucked away in the heart of Wianno, this charming waterfront home enjoys exceptional privacy and scenic views of Neck Pond and the Wianno Golf Course.Set on .73 of an acre, this property has been held by the same family for generations and is now ready for its next chapter. Ideally located close to Dowses Beach and Osterville village, this home is the perfect Cape Cod get-away with room to

  Gene Orloff Sotheby's International Realty

  51 Wianno Cir, Osterville, MA 02655
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  /49

  $1,500,000 Sold Jul 11, 2025

  • 1,471 Sq Ft
  • $1,020/SF
  • 120 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1870

  19 E Bay Rd, Osterville, MA 02655

  Rare opportunity on one of Osterville's finest streets. East Bay Road offers a scenic route between the charming village center and beloved Dowses Beach. Remarkable estates and saltwater marshes line the street leading up to the bay itself. Sitting atop a 0.4 acre parcel with a sprawling front lawn, 19 East Bay Road was recently renovated to elevate the historic home's style and functionality. A

  Shaelyn Hegarty Frank A Sullivan Real Estate

  19 E Bay Rd, Osterville, MA 02655
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  /51

  Est $1,063,872 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,162 Sq Ft

  31 Newport Ln, Osterville, MA 02655

  31 Newport Ln, Osterville, MA 02655
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  /43

  $9,995,000

  • 5 Beds
  • 5.5 Baths
  • 7,565 Sq Ft

  168 Garrison Ln, Osterville, MA 02655

  Set on highly sought-after Garrison Lane, this extraordinary residence boasts one of the most desirable locations in Osterville with panoramic views of West Bay and Eel River. The property is a boater's paradise with a protected deep-water dock offering easy access to Nantucket Sound. Beautifully constructed with exquisite finishes, the five-bedroom home is positioned to provide stunning water

  Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

  168 Garrison Ln, Osterville, MA 02655
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  /34

  $1,025,000 Sold Jul 08, 2025

  • 1,868 Sq Ft
  • $549/SF
  • 40 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  141 Parsley Ln, Osterville, MA 02655

  Oyster Hills - Definitely one of the most desirable neighborhoods in Osterville and this charming home is an example of why. Positioned on a corner lot surrounded by recently built or renovated beautiful homes that only make this home more valuable. Don't be put off by 2 bedrooms if you need more as there's plenty of space to include another bedroom or two and certainly another living space and

  Julie White William Raveis Real Estate & Home Services

  141 Parsley Ln, Osterville, MA 02655
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  /29

  Est $2,674,764 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,684 Sq Ft

  65 Starboard Ln, Osterville, MA 02655

  65 Starboard Ln, Osterville, MA 02655
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  /82

  $2,879,000

  • 5 Beds
  • 4.5 Baths
  • 4,715 Sq Ft

  98 Bunker Hill Rd, Osterville, MA 02655

  Experience the epitome of bayside living at 98 Bunker Hill Road, nestled in Osterville's distinguished Seapuit neighborhood. Sitting peacefully on over 2 acres, this 4,715 sq. ft. estate offers five bedrooms, including three with ensuite baths, and a host of inviting spaces perfect for relaxation or entertaining. Exterior assets include an attached three car garage, an abundant backyard with a

  Shaelyn Hegarty Frank A Sullivan Real Estate

  98 Bunker Hill Rd, Osterville, MA 02655
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  /38

  $2,500,000 Sold Jul 02, 2025

  • 1,960 Sq Ft
  • $1,276/SF
  • 10 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1950

  47 Great Bay Rd, Osterville, MA 02655

  Ready for Summer!!! Perfectly positioned on an expansive half-acre corner lot in Osterville's coveted Little Island neighborhood, this beautifully maintained three-bedroom residence offers water views of North Bay with deeded water access and is ready for occupancy for your summer enjoyment. The thoughtfully designed layout features a sunlit kitchen with a breakfast nook that opens to a welcoming

  Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

  47 Great Bay Rd, Osterville, MA 02655
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  /78

  Est $2,532,187 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,800 Sq Ft

  8 Nutmeg Ln, Osterville, MA 02655

  8 Nutmeg Ln, Osterville, MA 02655
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  /76

  $2,595,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,510 Sq Ft

  162 Starboard Ln, Osterville, MA 02655

  Experience tranquility and charm on nearly two acres of prime Bumps River waterfront. Start your day with a peaceful sunrise from the back deck, coffee in hand, as you watch wildlife gracefully soar around you.Enjoy the ease of one-floor living with a thoughtfully designed floor plan that maximizes views from the kitchen, family room, living room, and primary bedroom, constantly reminding you why

  Michelle Tucker William Raveis Real Estate & Home Services

  162 Starboard Ln, Osterville, MA 02655
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  /39

  $1,000,000 Sold Jul 01, 2025

  • 1,153 Sq Ft
  • $867/SF
  • 137 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1927

  38 Sunset Ln, Osterville, MA 02655

  Osterville Village! Experience the best of coastal living in this beautifully updated ranch, nestled in the heart of Osterville Village. Step inside to discover a light-filled, open floor plan where a fully renovated kitchen with quartz countertops and stainless steel appliances awaits your culinary creativity. With two new bathrooms, updated electrical, plumbing, and new HVAC system, this home

  Colleen Riley Sotheby's International Realty

  38 Sunset Ln, Osterville, MA 02655
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  /56

  Est $5,801,947 Not Listed For Sale

  • 8 Beds
  • 12 Baths
  • 10,027 Sq Ft

  159 Main St, Osterville, MA 02655

  159 Main St, Osterville, MA 02655
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  /24

  $3,500,000 Pending

  • 4 Beds
  • 5 Baths
  • 5,460 Sq Ft

  780 Sea View Ave, Osterville, MA 02655

  Your endless summer awaits at this premium Osterville property. A short stroll brings you to your private beach on Nantucket sound, while across the way enjoy private access to Eel River - ideal for launching a kayak or paddle board. It's hard to imagine a more welcoming, perfectly positioned and spacious home. Exquisitely maintained, every room is light-infused and gracious, with high ceilings,

  Ellen Valentgas Sotheby's International Realty

  780 Sea View Ave, Osterville, MA 02655

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