Waterfront homes for sale & real estate in Osterville, MA

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3D WALKTHROUGH

ABOUT THIS HOME
Waterfront Home for sale in Osterville, MA:
On Little Island in Osterville, where the tide shapes each day, stands a home that feels like it’s been waiting for you—quietly, patiently, knowing you belong here. Step inside and soaring one-and-a-half-story ceilings lift your gaze toward light and space. Shingle-style architecture and exquisite millwork reflect timeless craftsmanship. Broad windows reveal shimmering glimpses of West Bay, reminding you the sea is always near, with deeded North Bay rights just steps away. More than a house, this is the feeling of coming home. Set on 1.13 acres of park-like grounds with a newly added pool, this 6,700-square-foot masterpiece was created for living and belonging, offering five bed

$4,550,000

5 beds6 baths6,768 sq ft

405 Bridge St, Osterville, MA 02655

Broad windows • Newly added pool • Exquisite millwork

ABOUT THIS HOME
Waterfront Home for sale in Osterville, MA:
With a prime in-town location, this 3-bedroom, 1.5-bath Osterville Cape offers the perfect blend of character, comfort, and convenience. The sun-soaked living room welcomes you with gleaming oak floors and an inviting wood-burning fireplace, creating a cozy yet open atmosphere. A private dining room and first-floor primary bedroom provide flexible living options, while the updated full bath adds modern comfort. The kitchen features new appliances, ample storage, and space for casual dining—ideal for everyday living or entertaining guests. Downstairs, a versatile bonus space serves perfectly as a mudroom, home office, or den, with a convenient half bath and direct access to the one-car

$799,000

3 beds1.5 baths1,136 sq ft

123 Tower Hill Rd, Osterville, MA 02655

Private dining room • Updated full bath • New appliances

VIDEO TOUR

ABOUT THIS HOME
Waterfront Home for sale in Osterville, MA:
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 and breakfast bar sits adjacent to a vaulted family room with access to a private front brick patio—ideal for relaxing with your morning coffee. Looking for more outdoor living? A conceptual rendering in photos shows an optional design to create a private patio oasis-Board has indicated appro

$1,895,000

3 beds3.5 baths3,551 sq ft

199 East Bay Rd #13, Osterville, MA 02655

Tray ceiling • Hardwoods • First floor

ABOUT THIS HOME
Waterfront Home for sale in Osterville, MA:
Presenting the quintessential Cape Cod retreat with dazzling views of Nantucket Sound and a private sandy beach. Built in 1930, the residence showcases Old World craftsmanship and original details throughout, including wide heart pine plank floors and paneling. At the heart of the home, a spacious living room with beamed ceilings, built-in bookshelves, and a fireplace gives way to a magnificent sunroom overlooking the ocean. The all-white kitchen is complete with a pantry, breakfast bar, and direct access to the swimming pool and patio area. A first-floor primary suite boasts breathtaking ocean views, while an en suite guest bedroom completes the main level. The second floor features 4 bedr

$5,995,000

6 beds5 baths4,021 sq ft

439 Sea View Ave, Osterville, MA 02655

Beamed ceilings • Built-in bookshelves • Private sandy beach

3D WALKTHROUGH

ABOUT THIS HOME
Waterfront Home for sale in Osterville, MA:
At the west end of Osterville’s iconic Sea View Avenue in Wianno, this extraordinary estate is more than a home—it is a masterpiece of craftsmanship and artistry. Set on 1.2 acres of horticultural privacy with glimpses of West Bay, the 7,350 sq. ft. residence showcases hand-built mahogany windows and doors, quartersawn oak floors, curved walls and bespoke cabinetry and moldings—all created with skill from a bygone era. Seven bedrooms in the main house are complemented by a one-bedroom apartment above the three-car garage, complete with radiant floors. Outdoors, a 50-foot gunite pool and stone terrace shaded by Japanese maples invite alfresco dining, while waves on Nantucke

$7,950,000

8 beds8 baths7,350 sq ft

850 Sea View Ave, Osterville, MA 02655

Curved walls • 50-foot gunite pool • Bespoke cabinetry

Property at 168 Garrison Ln, Osterville, MA 02655, 5 beds, 5.5 baths

$9,995,000

5 beds5.5 baths7,565 sq ft

168 Garrison Ln, Osterville, MA 02655

Property at 414 Eel Riv, Osterville, MA 02655, 10 beds, 7.5 baths

$3,499,999

10 beds7.5 baths6,905 sq ft

414 Eel Riv, Osterville, MA 02655

Property at 440 Grand Island Dr, Osterville, MA 02655, 7 beds, 10 baths

$7,750,000

7 beds10 baths11,546 sq ft

440 Grand Island Dr, Osterville, MA 02655

Property at 920 Main St Unit 2-1, Osterville, MA 02655, 2 beds, 2 baths

$615,000

2 beds2 baths1,150 sq ft

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

Property at 14 Indian Trl, Osterville, MA 02655, 5 beds, 4 baths

$10,500,000

5 beds4 baths3,087 sq ft

14 Indian Trl, Osterville, MA 02655

Property at 71 Sand Pt, Osterville, MA 02655, 5 beds, 5 baths

$12,250,000

5 beds5 baths5,747 sq ft

71 Sand Pt, Osterville, MA 02655

Property at 51 Wianno Cir, Osterville, MA 02655, 3 beds, 2 baths

$2,395,000

3 beds2 baths1,194 sq ft

51 Wianno Cir, Osterville, MA 02655

Property at 501 Eel River Rd, Osterville, MA 02655, 6 beds, 8 baths

$10,500,000

6 beds8 baths8,203 sq ft

501 Eel River Rd, Osterville, MA 02655

Property at 25 Oyster Way, Osterville, MA 02655, 5 beds, 4.5 baths

$10,450,000

5 beds4.5 baths7,157 sq ft

25 Oyster Way, Osterville, MA 02655

Property at 255 Bayberry Way, Osterville, MA 02655, 7 beds, 6 baths

$8,950,000

7 beds6 baths4,896 sq ft

255 Bayberry Way, Osterville, MA 02655

Property at Lot 290 0 Indian Trl, Osterville, MA 02655

$3,125,000

— beds— baths— sq ft

Lot 290 0 Indian Trl, Osterville, MA 02655

Property at Lot 288 Seapuit River Rd A, Osterville, MA 02655

$3,100,000

— beds— baths— sq ft

Lot 288 Seapuit River Rd A, Osterville, MA 02655

Property at Lot 289 Seapuit River Road B, Barnstable, MA 02655

$3,000,000

— beds— baths— sq ft

Lot 289 Seapuit River Road B, Barnstable, MA 02655

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NEW CONSTRUCTION

ABOUT THIS HOME
Waterfront Home for sale in Osterville, MA:
Fabulous opportunity to own new construction in desirable Cotuit Bay Shores. This Ranch style home features an open floor plan, cathedral ceiling, Primary Suite and two car garage. You will love the location as it is close to the Association Beach, Tennis and Pickle Courts and Playground. Spring occupancy!! Photos represent model home.

$1,350,000

3 beds2 baths1,596 sq ft

564 Cotuit Bay Dr, Cotuit, MA 02635

0.68 acre lot • $85 HOA • 2 garage spots

ABOUT THIS HOME
Waterfront Home for sale in Osterville, MA:
One of Cape Cod’s premier waterfront estates, this exquisite Cotuit Bay compound offers a resort-style pool, stunning views, and one of the area’s most significant deep-water docks with direct access to Nantucket Sound. The seven-bedroom residence is finished to the highest standards with exquisite craftsmanship and top-of-the-line finishes throughout. At the heart of the home, an eat-in chef’s kitchen opens to a sunlit living area with a wet bar, all connecting seamlessly to a covered terrace with an outdoor kitchen overlooking the pool and bay. Highlights include an elegant primary suite with two balconies, a two-bedroom apartment, a third-floor study with panoramic view

$12,500,000

7 beds7.5 baths7,467 sq ft

835 Old Post Rd, Cotuit, MA 02635

1.33 acre lot • 4 garage spots • Pool

ABOUT THIS HOME
Waterfront Home for sale in Osterville, MA:
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 and plenty of woods beyond for privacy. Deck off kitchen for outdoor dining. Inside you'll find a large L with a gas FP for those cozy winter nights and hardwood floors, which continue through the kitchen/dining and 1st fl bedroom. The kitchen features white-painted oak cabinets, black granit

$1,115,000

4 beds2 baths1,775 sq ft

40 Waterfield Rd, Osterville, MA 02655

1.31 acre lot • 2 garage spots • Car-dependent

ABOUT THIS HOME
Waterfront Home for sale in Osterville, MA:
Welcome to an exquisite 2 acre waterfront estate, complete with panoramic water views, deep water dock and an in-ground gunite pool in the serene setting of Baxter Neck Road. This remarkable residence spans 9000 SF, artfully combining elegance with a relaxed casual charm promising both privacy and grandeur. Upon entering, you are greeted by an expansive layout that effortlessly flows from one room to the next. With 5+ generously sized bedrooms and 8 luxurious baths, there's ample space for comfort and relaxation. Each room is thoughtfully designed, ensuring a perfect balance of sophistication & comfort. The living areas are adorned with fine finishes, showcasing an understated eleganc

$6,750,000

5 beds7 baths8,989 sq ft

359 Baxter Neck Rd, Marstons Mills, MA 02648

2.15 acre lot • $42 HOA • 3 garage spots

ABOUT THIS HOME
Waterfront Home for sale in Osterville, MA:
COTUIT - Come and enjoy one of CAPE COD'S nicest Villages. Situated in very close proximity to Cape Cod Bay. This home abuts Eagle Pond and Little River Sanctuary consisting of 182 Acres for those who love to hike. This builder's home consists of 5 Bedrooms/4Bathrooms. Step inside and you'll be greeted by a foyer that leads to the Formal Living Room, Dining Room, Family Room and Office. The large Kitchen has a great stove for those who enjoy cooking. On the 2nd floor the Primary Bedroom has a walk-in closet, private bath and a whirlpool tub. 3 Additional bedrooms share a bath with a tub shower and a large linen closet. The 5th Bedroom offers a cozy sitting area, private bath with a convenie

$1,775,000

5 beds4 baths4,163 sq ft

174 Little Riv, Cotuit, MA 02635

3 garage spots • Car-dependent

ABOUT THIS HOME
Waterfront Home for sale in Osterville, MA:
Must see this spacious, lovely home in the sought-after village of Osterville, just . 03 miles to shops and restaurants and under 1 mile to Dowses Beach on Nantucket Sound. Well cared for home with recent updates comes with strong rental history and is offered fully furnished for immediate use or continued investment. With over 2,900 sq. ft. , it features hardwood floors throughout, central air, and a spacious living room. Renovated kitchen with upgraded counters, cabinets, and wine refrigerator opens to a dining area with sliders to a deck and private backyard with outdoor shower. First floor includes two large bedrooms, including a primary with central full bath, plus a private wing with

$1,395,000

4 beds2.5 baths2,326 sq ft

77 Robbins St, Osterville, MA 02655

0.37 acre lot • Car-dependent

Property at 426 Old Post, Cotuit, MA 02635, 4 beds, 2 baths

$790,000

4 beds2 baths1,656 sq ft

426 Old Post, Cotuit, MA 02635

Property at 177 Bayview Cir, Osterville, MA 02655, 3 beds, 2.5 baths

$899,900

3 beds2.5 baths2,050 sq ft

177 Bayview Cir, Osterville, MA 02655

Property at 89 Swift Ave, Osterville, MA 02655, 4 beds, 2 baths

$1,175,000

4 beds2 baths2,674 sq ft

89 Swift Ave, Osterville, MA 02655

Property at 818 South Main St, Centerville, MA 02632, 3 beds, 2.5 baths

$2,295,000

3 beds2.5 baths2,338 sq ft

818 South Main St, Centerville, MA 02632

Property at 135 Putnam Ave, Cotuit, MA 02635

$6,950,000

— beds— baths— sq ft

135 Putnam Ave, Cotuit, MA 02635

Waterfront Homes for Sale in Osterville

There are currently 18 waterfront homes for sale in Osterville at a median listing price of $7.02M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Osterville stay on the market for 133 days. Popular neighborhoods include Centerville, Mid Cape, Upper Cape, Marstons Mills, and Cotuit. This map is refreshed with the newest listings in Osterville every 15 minutes.

In the past month, 2 homes have been sold in Osterville. In addition to houses in Osterville, there were also 4 condos, 1 townhouse, and 1 multi-family unit for sale in Osterville last month. Find your dream home in Osterville using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Osterville are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Osterville. If you're looking to sell your home in the Osterville area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Osterville with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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