Osterville Homes

/40
Est $705,699 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,767 Sq Ft
36 Renoir Dr, Osterville, MA 02655

36 Renoir Dr, Osterville, MA 02655

/27
$3,100,000 Pending
- 4 Beds
- 3.5 Baths
- 3,720 Sq Ft
355 Bridge St, Osterville, MA 02655

The quintessential Cape Cod summer awaits at this gracious Osterville home set on picturesque Little Island. Savor every minute of summer with deeded rights to North Bay, and enjoying your private, fully fenced back yard with lush professional landscaping, beautiful gunite pool, firepit and outdoor dining. An expansive main floor makes the most of gathering spaces and indoor-outdoor living, with

Ellen Valentgas Sotheby's International Realty

355 Bridge St, Osterville, MA 02655
/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

/33
Est $717,430 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,267 Sq Ft
44 Renoir Dr, Osterville, MA 02655

44 Renoir Dr, Osterville, MA 02655

/34
$1,125,000 Open Sat 11AM - 1PM
- 4 Beds
- 2 Baths
- 1,775 Sq Ft
40 Waterfield Rd, Osterville, MA 02655

Your love affair will begin as you pull into the crushed stone, horseshoe drive w/ cobblestone aprons lined with white hydrangeas. This home looks like something out of a fairytale. A paved drive leads down to the 2-car gar., with basement access. In the rear, you'll find a large bluestone patio with an outdoor bar, TV, a seating area w/fire pit, and an outdoor shower. There’s a lush green lawn

Gervais Group Keller Williams Realty

40 Waterfield Rd, Osterville, MA 02655
/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

/37
Est $697,560 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,806 Sq Ft
65 Renoir Dr, Osterville, MA 02655

65 Renoir Dr, Osterville, MA 02655

/58
$9,995,000
- 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

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

168 Garrison Ln, Osterville, MA 02655
/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

/34
Est $709,106 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,665 Sq Ft
25 Renoir Dr, Osterville, MA 02655

25 Renoir Dr, Osterville, MA 02655

/26
$699,900
- 3 Beds
- 2 Baths
- 1,152 Sq Ft
369 Bumps River Rd, Osterville, MA 02655

Welcome to your new home in the highly sought-after village of Osterville! This charming 3 BD, 2 BA ranch at 369 Bumps River Road offers classic Cape Cod living. As you step inside, the living room's vaulted ceiling creates a spacious, inviting atmosphere, complete with a cozy fireplace for relaxing on a cool fall evening - heated by natural gas. Warm wood floors extend throughout the home,

Eric Dufault Keller Williams Realty

369 Bumps River Rd, Osterville, MA 02655
/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

/40
Est $653,672 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,267 Sq Ft
38 Vermeer Ct, Osterville, MA 02655

38 Vermeer Ct, Osterville, MA 02655

/33
$605,000 Open Sun 10:30AM - 11:30AM
- 2 Beds
- 1 Bath
- 1,179 Sq Ft
268 Bumps River Rd, Osterville, MA 02655

Welcome to this charming ranch in Osterville, one of Cape Cod's most coveted villages south of Route 28. Offering 2 bedrooms and 1 bath, this home features hardwood floors, a renovated kitchen with quartz countertops and stainless appliances, and a partially finished basement with family room, laundry, and space for overflow guests. Enjoy modern comforts with new central A/C and FHA gas heat. The

Christine Richards Kinlin Grover Compass

268 Bumps River Rd, Osterville, MA 02655
/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

/14
Est $637,797 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
37 Captain Aldens Ln, Osterville, MA 02655

37 Captain Aldens Ln, Osterville, MA 02655

/49
$1,895,000
- 3 Beds
- 3.5 Baths
- 3,551 Sq Ft
199 E Bay Rd Unit 13, Osterville, MA 02655

Rarely available, this Cape Cod-style townhome in The Cove at East Bay offers low-maintenance living just minutes from Osterville Village shops, dining, and Dowses Beach. The main level features hardwood floors, a tray-ceilinged living room with bay window, gas fireplace, and custom millwork. Rich trim and transom windows frame the formal dining room. The granite kitchen with stainless appliances

Susan Crasnick Sotheby's International Realty

199 E Bay Rd Unit 13, Osterville, MA 02655
/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

/26
Est $785,222 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,541 Sq Ft
102 Old East Osterville Rd, Osterville, MA 02655

102 Old East Osterville Rd, Osterville, MA 02655

/36
$615,000
- 2 Beds
- 2 Baths
- 1,150 Sq Ft
920 Main St Unit 1 Building 2, Osterville, MA 02655

Wouldn't you just love to have one of Cape Cod's most charming Main Streets at your front door? Osterville, the place to enjoy shopping, dining, and small village community all year round. This lovingly updated condo in Osterville Village is just the place for you. One floor living at it's best. Step through the main entry directly into your 2 bed, 2 bath, ranch style home. Gleaming hardwoods,

Madeline Lacroix Keller Williams Realty

920 Main St Unit 1 Building 2, Osterville, MA 02655
/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

/39
Est $784,225 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,853 Sq Ft
104 King Arthur Dr, Osterville, MA 02655

104 King Arthur Dr, Osterville, MA 02655

/35
$615,000
- 2 Beds
- 2 Baths
- 1,150 Sq Ft
920 Main St Unit 2-1, Osterville, MA 02655

Osterville, the place to enjoy shopping, dining, and small village community all year round. This lovingly updated condo in Osterville Village is just the place for you. One floor living at it's best. Step through the main entry directly into your 2 bed, 2 bath, ranch style home. Gleaming hardwoods, fresh paint, new appliances and windows, beautiful built ins, and wood burning fireplace. The

Madeline Lacroix Keller Williams Realty

920 Main St Unit 2-1, Osterville, MA 02655
/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

/22
Est $713,779 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,284 Sq Ft
9 Gunstock Rd, Osterville, MA 02655

9 Gunstock Rd, Osterville, MA 02655

/46
$1,395,000 Open Sat 12PM - 1:30PM
- 4 Beds
- 2.5 Baths
- 2,976 Sq Ft
77 Robbins St, Osterville, MA 02655

Lovely and spacious home in the sought-after village of Osterville. Ideally located just .03 miles to shops and restaurants and less than a mile to the warm waters of Dowses Beach on Nantucket Sound. This well-cared-for property offers an excellent rental history and is being sold fully furnished, ready for immediate enjoyment or as a continued investment opportunity. With over 2,900 sq. ft. of

Deb Kenney Berkshire Hathaway HomeServices Robert Paul Properties

77 Robbins St, Osterville, MA 02655
/34
$560,000 Sold Jun 27, 2025
- 1,560 Sq Ft
- $359/SF
- 16 Days On Market
- 2 Beds
- 2 Baths
- Built 1986
7 Fox Hollow Ln, Osterville, MA 02655

Looking for a Cape Cod home to make your own? This light-filled Saltbox offers a welcoming floor plan and great potential as a year-round residence, seasonal getaway, or investment. The sunny open layout is ideal for entertaining, with a spacious living room featuring a fireplace, cathedral ceilings, and skylights. The kitchen with breakfast nook opens to a large back deck—perfect for summer

Cindy Harrington Berkshire Hathaway HomeServices Robert Paul Properties

7 Fox Hollow Ln, Osterville, MA 02655

/17
Est $696,188 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,144 Sq Ft
7 Bonnie Briar Rd, Osterville, MA 02655

7 Bonnie Briar Rd, Osterville, MA 02655

/42
$1,295,000
- 3 Beds
- 2 Baths
- 3,387 Sq Ft
44 Avalon Cir, Osterville, MA 02655

On a quiet cul-de-sac in Osterville, this contemporary Cape blends architectural charm with a resort-inspired lifestyle. The backyard is the piece de resistance, with a sparkling pool, expansive deck, and gazebo framed by mature landscaping—perfect for entertaining or retreat. Inside, renovations highlight wood floors, exposed beam ceilings, and brick hearth fireplaces, creating warmth and

Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

44 Avalon Cir, Osterville, MA 02655
/36
$2,400,000 Sold Jun 26, 2025
- 4,192 Sq Ft
- $573/SF
- 16 Days On Market
- 4 Beds
- 4 Baths
- Built 1914
88 Bridge St, Osterville, MA 02655

Ideally located between Oyster Harbors and the Wianno Club, this beautifully maintained coastal home offers stunning views of West Bay in a tranquil, private setting. The main residence features three bedrooms, including two guest rooms on the first floor and a spacious primary suite upstairs with a sunlit balcony overlooking the bay. A welcoming living room with fireplace and walls of windows

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

88 Bridge St, Osterville, MA 02655

/47
Est $716,581 Not Listed For Sale
- 2 Beds
- 2 Baths
- 2,288 Sq Ft
598 Bumps River Rd, Osterville, MA 02655

598 Bumps River Rd, Osterville, MA 02655

/40
$899,900
- 3 Beds
- 2.5 Baths
- 2,050 Sq Ft
177 Bayview Cir, Osterville, MA 02655

Enjoy all that Osterville has to offer! This adorable 3 bedroom, 3 bath Cape is in the perfect village setting. This home has hardwood floors, an updated eat in kitchen, first floor primary with bath and private deck, large,bright, heated sunroom, first floor laundry, whole house generator, newer windows, and a finished lower level with a walk out basement; great for an in-law suite or other

Kathleen Craig Berkshire Hathaway HomeServices Robert Paul Properties

177 Bayview Cir, Osterville, MA 02655
/37
$810,000 Sold Jun 24, 2025
- 1,650 Sq Ft
- $491/SF
- 5 Days On Market
- 3 Beds
- 2 Baths
- Built 1971
106 Hickory Hill Cir, Osterville, MA 02655

Charming Cape in Osterville Village! This beautifully maintained Cape is move-in ready with thoughtful updates throughout! Gleaming hardwood floors flow through the home, with ceramic tile in both bathrooms. The cozy living room features a wood-burning fireplace insert, while the updated kitchen boasts stylish cabinetry and sleek countertops. Recent upgrades include newer gas heating, central

Eileen Prisco Prisco's Five Star Real Estate

106 Hickory Hill Cir, Osterville, MA 02655

/30
Est $714,195 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,880 Sq Ft
160 Acorn Dr, Osterville, MA 02655

160 Acorn Dr, Osterville, MA 02655

/52
$1,225,500
- 3 Beds
- 2.5 Baths
- 2,776 Sq Ft
81 Falling Leaf Ln, Osterville, MA 02655

Welcome to this finely crafted custom Cape, set in one of Osterville's desirable locations. Designed with sophistication & comfort in mind, the home showcases sun-filled, spacious rooms, elegant molding, & timeless hardwood flooring throughout.The first floor offers a front foyer, an open kitchen with walk-in pantry, island and dining area, and a formal dining room perfect for gatherings. French

Linda Whitcomb William Raveis Real Estate & Home Services

81 Falling Leaf Ln, Osterville, MA 02655
/38
$845,000 Sold May 30, 2025
- 1,656 Sq Ft
- $510/SF
- 10 Days On Market
- 3 Beds
- 2 Baths
- Built 1972
171 Sturbridge Dr, Osterville, MA 02655

OPEN HOUSES CANCELLED! Discover an incredible opportunity to own a meticulously maintained, move-in ready home in the coveted village of Osterville. Tucked within a lovely neighborhood, 171 Sturbridge Drive is a pristine property that exudes Cape Cod charm. Just minutes from Dowses Beach and the vibrant village center-home to boutique shops, fine dining, and cozy cafes-this residence offers the

Shaelyn Hegarty Frank A Sullivan Real Estate

171 Sturbridge Dr, Osterville, MA 02655

/40
Est $984,888 Not Listed For Sale
- 2 Beds
- 2 Baths
- 2,040 Sq Ft
122 Falling Leaf Ln, Osterville, MA 02655

122 Falling Leaf Ln, Osterville, MA 02655

/21
$599,500
- 1 Bed
- 1 Bath
- 720 Sq Ft
16 2nd Ave Unit 5A, Osterville, MA 02655

Tucked along picturesque Parker Road, between the Osterville Historical Museum and Wianno Golf Course, the beloved Aunt Tempy's Cottages capture the essence of Cape & Islands living - weathered shingles, crisp white trim, and beautifully kept grounds. This historic 10-unit association offers a lovely blend of character and convenience, all within steps of the village. Unit 5A underwent a full

Shaelyn Hegarty Frank A Sullivan Real Estate

16 2nd Ave Unit 5A, Osterville, MA 02655
/27
$2,425,000 Sold May 28, 2025
- 2,573 Sq Ft
- $942/SF
- 1 Day On Market
- 4 Beds
- 2.5 Baths
- Built 2003
25 Blanid Rd, Osterville, MA 02655

In the heart of Osterville Village, this shingle-style home blends classic Cape Cod charm with modern comfort. The eat-in kitchen features stainless steel appliances, a spacious island, and a sunlit breakfast nook, flowing easily to the dining room with views of the pool and private backyard. A living room and office complete the main living spaces. The first-floor primary suite includes a

Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

25 Blanid Rd, Osterville, MA 02655

/49
Est $1,079,201 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 1,759 Sq Ft
523 Bumps River Rd, Osterville, MA 02655

523 Bumps River Rd, Osterville, MA 02655

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