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
• Explore Osterville

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  /17

  $2,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,544 Sq Ft
  • House for Rent

  31 Robbins St, Osterville, MA 02655

  Year round- Avail for ONE YEAR ONLY Mid Sept, 2025 thru Sept, 2026 Three bedroom two bath ranch located on a quiet street. Close to great town restaurants and Dowses Beach. Deck and private back yard. No smoking of any kind. 1st, last and security required. Avail Sept

  Team 300 Today Real Estate

  31 Robbins St, Osterville, MA 02655
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  /55

  $635,000 Sold Oct 15, 2025

  • 884 Sq Ft
  • $718/SF
  • 9 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1929

  22 1st Ave, Osterville, MA 02655

  Adorable Cape Cod style home located in the sought after Avenues with deeded beach and recreation area at Sea Side Park. Wonderful for year round living or your Cape retreat. Also a wise investment location for leasing with close proximity to world famous Craigville Beach, The Melody Tent and all of the Hyannis attractions. You will love the spacious summer porch for catching the breezes and

  Adrienne Siegel Strawberry Hill R E

  22 1st Ave, 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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  /26

  $357,000

  • 2 Beds
  • 1 Bath
  • 594 Sq Ft

  3040 Falmouth Rd Unit H, Osterville, MA 02655

  Welcome to 3040 Falmouth Rd, Unit H—a rare free-standing condo in the sought-after Osterville Pines community. This charming detached condo lives like a single-family (electric, heat, gas and water included in condo fees), featuring hardwood floors, high ceilings, and a fireplaced living room opening to a bright eat-in kitchen. Two sunny bedrooms and a beautifully renovated bath with river stone

  Livia Monteforte

  Compass

  (508) 514-5783

  3040 Falmouth Rd Unit H, Osterville, MA 02655
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  /46

  $2,500 total monthly price

  • 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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  /40

  $1,600,000 Sold Oct 15, 2025

  • 2,050 Sq Ft
  • $780/SF
  • 69 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1961

  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 Hathway 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

  72 Hathaway Rd, Osterville, MA 02655
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  /49

  Est $1,250,287 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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  /27

  $357,000

  • 2 Beds
  • 1 Bath
  • 594 Sq Ft

  3040 Falmouth Rd Unit H, Osterville, MA 02655

  Welcome to 3040 Falmouth Road, Unit H--a rare, free-standing condo tucked within the sought-after Osterville Pines community. This absolutely charming residence lives like a single-family home and features beautiful hardwood floors, high ceilings, and a cozy living room that opens to a sunlit, eat-in kitchen. Two perfectly sized bedrooms are filled with natural light, and the fully renovated

  Livia Monteforte

  Compass Massachusetts, LLC

  (508) 257-7938

  3040 Falmouth Rd Unit H, Osterville, MA 02655
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  /76

  $2,210,000 Sold Oct 08, 2025

  • 3,510 Sq Ft
  • $630/SF
  • 390 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1971

  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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  /46

  Est $1,244,739 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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  /66

  $624,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,316 Sq Ft

  17 Avalon Cir, Osterville, MA 02655

  Welcome to Osterville, where timeless elegance meets Cape Cod's coastal charm! This beautifully updated 3-bedroom, 1.5-bath ranch offers easy one-floor living in one of Barnstable's most sought-after villages. The 1,316 sq. ft. layout includes a primary suite with private half bath and 2 additional bedrooms, all enhanced by gleaming hardwood floors (2022). Enjoy peace of mind with major updates:

  John Fallon LAER Realty Partners

  17 Avalon Cir, Osterville, MA 02655
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  /12

  $660,000 Sold Oct 03, 2025

  • 1,276 Sq Ft
  • $517/SF
  • 27 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1968

  33 Aspen Way, Osterville, MA 02655

  Welcome to 33 Aspen Way, a charming ranch-style home in the highly desirable village of Osterville. This solidly built residence features 3 bedrooms, 1 1/2 baths, and a 1-car garage, all set on a beautifully landscaped lot.The open floor plan creates a natural flow throughout the main living areas, offering comfort and flexibility for everyday living or entertaining. Upgrades include a new roof,

  Derek Greene The Greene Realty Group

  33 Aspen Way, Osterville, MA 02655
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  /50

  Est $951,156 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,061 Sq Ft

  65 Deerfield Rd, Osterville, MA 02655

  65 Deerfield Rd, Osterville, MA 02655
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  /50

  $13,500,000

  • 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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  /24

  $3,400,000 Sold Oct 03, 2025

  • 5,460 Sq Ft
  • $623/SF
  • 1 Day On Market

  • 4 Beds
  • 5 Baths
  • Built 1987

  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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  /40

  Est $1,415,477 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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  /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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  /40

  $665,000 Sold Sep 23, 2025

  • 1,196 Sq Ft
  • $556/SF
  • 20 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  35 Sharon Cir, Osterville, MA 02655

  Tucked away on a quiet cul-de-sac in the heart of Osterville Heights, this lovingly maintained 3-bedroom, 2-bath ranch offers comfort, charm, and room to grow. Sited on a professionally landscaped .74-acre lot with irrigation throughout, the home is surrounded by mature trees, flowering perennials, stone walkways, and handsome stone walls. The fully fenced backyard features a gated entry,

  Christine Richards Kinlin Grover Compass

  35 Sharon Cir, Osterville, MA 02655
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  /56

  Est $2,610,476 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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  /35

  $3,499,999

  • 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 Real Estate Investments and Development Co.

  414 Eel River Rd, Osterville, MA 02655
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  /42

  $690,000 Sold Sep 16, 2025

  • 1,830 Sq Ft
  • $377/SF
  • 9 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  40 Gunstock Rd, Osterville, MA 02655

  **OPEN HOUSE CANCELED** Bright and updated Osterville oasis! Tucked into a peaceful neighborhood south of Route 28, this beautifully-updated home blends Cape Cod charm with modern comforts that include a refreshed kitchen, updated baths, new flooring and energy-efficient solar panels. The sun-filled interior creates a warm and welcoming atmosphere while the spacious deck is perfect for

  Kevin Eosco Today Real Estate

  40 Gunstock Rd, Osterville, MA 02655
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  /39

  Est $3,287,301 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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  /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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  /59

  $10,500,000 Sold Sep 16, 2025

  • 3,859 Sq Ft
  • $2,721/SF
  • 105 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 1947

  545 Sea View Ave, Osterville, MA 02655

  Set on Osterville's prestigious Sea View Avenue, this exquisite waterfront estate boasts an unparalleled combination of privacy, presence, and natural beauty. Sweeping views of Nantucket Sound and a pristine private sandy beach highlight this one-of-a-kind offering, located just minutes from everything Osterville has to offer. Accessed via a long, tree-lined driveway, coastal gardens and rolling

  Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

  545 Sea View Ave, Osterville, MA 02655
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  /51

  Est $1,008,922 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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  /31

  $2,395,000

  • 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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  /32

  $1,165,000 Sold Sep 15, 2025

  • 2,098 Sq Ft
  • $555/SF
  • 110 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1972

  50 Deerfield Rd, Osterville, MA 02655

  Nestled in a quiet neighborhood near Dowses Beach and Main Street Osterville, this updated Cape-style home exudes a coastal-casual vibe. The sun-filled first floor offers an open layout ideal for entertaining. The chef's kitchen features a large island, quartz countertops, GE Profile appliances, and a farmhouse sink overlooking the spacious backyard. Hardwood floors, crown molding and a stunning

  Joan Witter Compass Massachusetts, LLC

  50 Deerfield Rd, Osterville, MA 02655
• 

  

  /25

  Est $873,722 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 972 Sq Ft

  329 Swift Ave, Osterville, MA 02655

  329 Swift Ave, Osterville, MA 02655
• 

  

  /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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  /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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  /29

  Est $2,225,908 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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  /44

  $8,950,000

  • 7 Beds
  • 6 Baths
  • 4,896 Sq Ft

  255 Bayberry Way, Osterville, MA 02655

  Welcome to ''Point House'' a spectacular 5.98-acre waterfront estate on a peninsula overlooking the glistening waters of West Bay. In a setting of unsurpassed beauty, the 4,896 square foot residence offers truly exceptional water vistas, beautiful gardens, an expansive private sandy beach, and a substantial deep-water dock from which you can sail into the waters of Nantucket Sound. The 6-bedroom

  Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

  255 Bayberry Way, 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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  /78

  Est $2,642,949 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
• 

  

  /98

  $5,395,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 7,500 Sq Ft

  60 Smoke Valley Rd, Osterville, MA 02655

  Magnificent private shingle-style new construction home in Osterville's Seapuit area. Home has exquisite features both inside and out, including high-end fixtures, custom woodworking and cabinetry, gourmet kitchen with panoramic breakfast nook, media room, and elevator to all three stores are just to name a few. Landscaping with salt-water pool, pergola, patio, fireplace, outdoor kitchen and

  Gail Germain Martis Sotheby's International Realty

  60 Smoke Valley Rd, 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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  /44

  Est $1,655,786 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,754 Sq Ft

  132 Swift Ave, Osterville, MA 02655

  132 Swift Ave, Osterville, MA 02655
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  /12

  $2,995,000 Pending

  • 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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  /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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