Osterville Homes for Sale

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  $799,900

  $69K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  177 Bayview Cir, Osterville, MA 02655

  Wow what a rare opportunity to purchase an AFFORDABLE turnkey Quintessential Year-Round Cape within.5 mile of Osterville Village and 1 mile to Dowes Beach. The size of the house can be deceiving from the front elevation. Here are the details of the ~2100 sqft of living space. Main level of ~1150 sqft includes a primary suite, guest bedroom, 2 full baths, living room, E/I kitchen and sun porch.

  Derek Greene The Greene Realty Group

  177 Bayview Cir, Osterville, MA 02655
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  $7,995,000

  $2M PRICE DROP

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

  168 Garrison Ln, Osterville, MA 02655

  Nestled amid beautifully landscaped grounds, this exceptional 7,500± square foot residence captures breathtaking views over West Bay and Eel River. A private sandy beach and deep-water dock provide effortless access to Nantucket Sound, creating a rare combination of serenity and seafaring adventure. Inside, the five-bedroom home blends refined architecture with inviting coastal warmth. A dramatic

  Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

  168 Garrison Ln, Osterville, MA 02655
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  $1,995,000

  Open Sat 12:30PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 2,636 Sq Ft

  420 Starboard Ln, Osterville, MA 02655

  In Osterville, certain streets make the most of Village living. Starboard Lane, winding along the western shore of the Bumps River, is among the village's most coveted addresses. Known for gracious homes with exceptional privacy on large parcels, the convenience to the heart of Osterville is a huge plus. 420 Starboard Lane captures the Village vibe wonderfully. Set on 1.68 acres, this

  Jack Cotton, Jr Sotheby's International Realty

  420 Starboard Ln, Osterville, MA 02655
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  $599,900

  • 2 Beds
  • 1.5 Baths
  • 1,088 Sq Ft

  727 Main St Unit B1, Osterville, MA 02655

  RARE to market! First opportunity in YEARS in Osterville's sought after Wianno Knoll. Nestled in the heart of Osterville village this desirable first floor condo has it all! Gorgeous open floor plan features two spacious bedrooms, a completely updated full bath and charming guest half bath. Renovated open kitchen with pantry closet, stainless appliances. and sliders leading to private back porch

  Gregory W Nowak Craigville Realty Co

  727 Main St Unit B1, Osterville, MA 02655
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  $9,850,000

  $650K PRICE DROP

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

  14 Indian Trail, Osterville, MA 02655

  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, Osterville, MA 02655
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  $8,625,000

  • 7 Beds
  • 7.5 Baths
  • 7,315 Sq Ft

  63 Main St, Osterville, MA 02655

  Legacy estate set prominently on one of the highest Osterville bluffs delivers classic waterfront expectations with a superior dock and substantial dynamic views from the Vineyard to Hyannisport. The grand yesteryear home constructed in 1920 conveys the qualities of that oceanfront era, with higher ceilings, multiple great rooms, and the character of hidden porches, exclusive balconies, and

  Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

  63 Main St, Osterville, MA 02655
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  $945,000

  • 3 Beds
  • 2.5 Baths
  • 1,501 Sq Ft

  55 Deerfield Rd, Osterville, MA 02655

  Osterville Beauty! Nestled on a private lot offering a very private year yard with hot tub, fire pit deck, grill area and shed with Tiki bar! The interior of this 3 bedroom, 2.5 bath home shows like new! ideal floor plan for entertaining! The family room with beamed ceiling, nautical trim and fireplace is the perfect spot for "movie night!". The easy to navigate kitchen is fully applianced, with

  Margo Pisacano Margo & Company

  55 Deerfield Rd, Osterville, MA 02655
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  $2,950,000

  • 3 Beds
  • 3 Baths
  • 3,178 Sq Ft

  12 Cockachoiset Ln, Barnstable, MA 02655

  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

  Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

  12 Cockachoiset Ln, Barnstable, MA 02655
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  $9,850,000

  $650K PRICE DROP

  • 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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  $1,425,000

  $154K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,765 Sq Ft

  955 Main St, Osterville, MA 02655

  A mid-19th-century Greek Revival, believed to be the birthplace of Captain William Bradford Parker and later home to Samuel Hallett -- both tied to Osterville's historic maritime corridor along Main Street. The property reflects the success of maritime captains - there's a reason Osterville was once described as ''a place where retired sea captains can live like gentlemen.'' You feel that here.

  Karen Lilly Property Cape Cod

  955 Main St, Osterville, MA 02655
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  $7,250,000

  $750K PRICE DROP

  • 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 two-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. A gracious covered front porch

  Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

  440 Grand Island Dr, Osterville, MA 02655
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  $735,000

  $75K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft

  441 Old Mill Rd, Osterville, MA 02655

  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

  Diane Boudreau Kinlin Grover Compass

  441 Old Mill Rd, Osterville, MA 02655
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  $3,100,000

  • Land
  • 2.3 Acres
  • $1,347,826 per Acre

  Lot 288 Seapuit River Rd A, Barnstable, MA 02655

  Located in the heart of Oyster Harbors - Cape Cod's premier golf community - this 2.3-acre lot presents an outstanding opportunity to create a legacy estate. Set within the highly sought after village of Osterville, known for its timeless charm and distinguished properties, this expansive parcel offers ample space to design a custom estate with room for a main house, guest, house, pool and pool

  Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

  Lot 288 Seapuit River Rd A, Barnstable, MA 02655

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