Homes with Basements for Sale in Osterville, MA

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FLOOR PLAN

ABOUT THIS HOME
Home with Basement for sale in Osterville, MA:
* * NEW TO THE MARKET * * Quaint Cape Cod ranch welcomes you with the covered front porch with contemporary flair located in the heart of Osterville’s historic village coastal neighborhood. This home features an airy open floor plan with cathedral ceilings and recessed lighting throughout. The living room offers a gas fireplace and soaring cathedral ceiling. A vaulted foyer with closet provides an inviting entry. Kitchen highlights include cathedral ceilings, skylight, recessed lighting, oversized pantry, and a center island that opens to the dining area. Sliders lead to the outdoor deck for seamless indoor-outdoor living. First-floor laundry adds convenience. Split floor plan: The

$1,612,000

3 beds2 baths1,264 sq ft

137 Wianno Cir, Osterville, MA 02655

Covered front porch • Open floor plan • Vaulted foyer

ABOUT THIS HOME
Home with Basement for sale in Osterville, MA:
Exquisite waterfront estate in the gated enclave of Oyster Harbors, one of Cape Cod's most sought-after communities. Located minutes from everything Osterville has to offer, yet a world apart, the property represents a rare and extraordinary opportunity to own a generational compound in an inimitable setting. Ideally positioned to capture dramatic sunsets over Cotuit Bay and Nantucket Sound beyond, the estate features a stunning main residence, a two-bedroom guest cottage, a swimming pool, private dock, and more. A wooded drive gives way to manicured grounds of nearly two acres, transporting one to a private seaside resort as the ocean comes into view. Inside, an open layout caters to moder

$18,500,000

7 beds10 baths10,104 sq ft

47 Sunset Pt, Osterville, MA 02655

Waterfront estate • Gated enclave • Private dock

3D WALKTHROUGH

ABOUT THIS HOME
Home with Basement for sale in Osterville, MA:
Discover the charm of Wianno in this beautifully renovated four-bedroom, three-bath home, walking distance to Osterville Village, beaches, and the best of Cape Cod living. With deeded access to Eel River and lovely views overlooking the Wianno golf course, this inviting property offers a rare combination of location, comfort, and lifestyle. Thoughtfully designed for easy one-level living, the turnkey home features a warm and welcoming living room with fireplace, vaulted ceilings, and a relaxed country feel. The spacious deck overlooking the golf course provides an idyllic setting for morning coffee, summer entertaining, or unwinding at the end of the day. This home's exceptional location

$2,700,000

4 beds3 baths2,050 sq ft

72 Hathaway Rd Rd, Osterville, MA 02655

One-level living • 0.82 acre lot • 2 garage spots

3D WALKTHROUGH

ABOUT THIS HOME
Home with Basement for sale in Osterville, MA:
Representing the pinnacle of coastal elegance, this extraordinary estate on Little Island offers a rare opportunity for a generational compound in mint condition and an unsurpassed location. Finished to the highest standards, the property features a spectacular five-bedroom main residence, a swimming pool, a pool house with kitchenette and full bath, and a detached three-car garage with a home gym above. In the main residence, timeless and sophisticated design is on display throughout, with custom millwork, designer wallpaper, soaring vaulted ceilings, and a smart home system that governs doors, locks, and hardware with effortless ease. Superlative craftsmanship and finishes define every ro

$4,950,000

5 beds7.5 baths5,970 sq ft

313 Bridge St, Osterville, MA 02655

Swimming pool • Pool house • Custom millwork

VIDEO TOUR

ABOUT THIS HOME
Home with Basement for sale in Osterville, MA:
Waterfront home in the heart of Osterville Village, where charming shops, restaurants, and amenities are just a short stroll away. Enjoy spectacular, unobstructed views, sunsets and frontage on the picturesque North Bay- all this and room for a pool. This meticulously maintained and beautifully appointed home is move-in ready, offering the perfect opportunity to enjoy immediately or create your dream waterfront retreat. With a 5-bedroom septic system already installed, the property offers outstanding expansion potential, making it ideal for future additions or a custom renovation. Whether you're seeking a turnkey home or envisioning a larger estate, this exceptional property combines an unb

$4,250,000

3 beds3.5 baths2,721 sq ft

35 Blue Heron Dr, Osterville, MA 02655

Turnkey home • Room for a pool • Waterfront home

Property at 84 Hinckley Cir, Osterville, MA 02655, 3 beds, 1.5 baths

$725,000

3 beds1.5 baths1,008 sq ft

84 Hinckley Cir, Osterville, MA 02655

Property at 22 Scudder Rd, Osterville, MA 02655, 5 beds, 6 baths

$4,795,000

5 beds6 baths4,100 sq ft

22 Scudder Rd, Osterville, MA 02655

Property at 955 Main St, Osterville, MA 02655, 3 beds, 2 baths

$1,475,000

3 beds2 baths1,764 sq ft

955 Main St, Osterville, MA 02655

Property at 156 East Bay Rd, Osterville, MA 02655, 4 beds, 5 baths

$3,450,000

4 beds5 baths2,424 sq ft

156 East Bay Rd, Osterville, MA 02655

Property at 179 Pineleigh Path, Osterville, MA 02655, 5 beds, 6.5 baths

$5,950,000

5 beds6.5 baths8,740 sq ft

179 Pineleigh Path, Osterville, MA 02655

Property at 12 Cockachoiset Ln, Osterville, MA 02655, 3 beds, 3 baths

$2,950,000

3 beds3 baths3,178 sq ft

12 Cockachoiset Ln, Osterville, MA 02655

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

$7,995,000

5 beds5.5 baths7,565 sq ft

168 Garrison Ln, Osterville, MA 02655

Property at 727 Main St Apt B1, Osterville, MA 02655, 2 beds, 1.5 baths

$599,900

2 beds1.5 baths1,088 sq ft

727 Main St Apt B1, Osterville, MA 02655

Property at 93 Oyster Way, Osterville, MA 02655, 4 beds, 4 baths

$4,495,000

4 beds4 baths4,964 sq ft

93 Oyster Way, 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 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 14 Indian Trl, Osterville, MA 02655, 5 beds, 4 baths

$9,850,000

5 beds4 baths3,087 sq ft

14 Indian Trl, Osterville, MA 02655

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NEW 18 HRS AGO

ABOUT THIS HOME
Home with Basement for sale in Osterville, MA:
One of the best values among homes for sale in Osterville! Welcome to 329 Swift Avenue, a turnkey Osterville home offered at $799,000 with an established rental history, a desirable walk-to-village location, and exceptional future potential. Set on approximately . 3 acres, this charming Cape Cod property offers the space buyers are looking for, including a generous yard with potential for a pool, subject to permitting. Located just minutes from the heart of Osterville Village, this home puts shopping, dining, coffee, beaches and the best of the Cape Cod lifestyle within easy reach. Whether you are searching for a year-round Osterville home, Cape Cod summer house, second home, or investment

$799,000

3 beds2 baths1,856 sq ft

329 Swift Ave, Osterville, MA 02655

Generous yard • Oversized lot • Potential for a pool

ABOUT THIS HOME
Home with Basement for sale in Osterville, MA:
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. 2nd floor has a ~300 sqft bedroom or playroom perfect for kids visiting during the summer. The walk out lower level has ~650 sqft of finished space easily upgraded with heat for year-round use. The space is perfect for a separate seasonal rental or visitors to have separate living space which includ

$839,900

3 beds2.5 baths2,100 sq ft

177 Bayview Cir, Osterville, MA 02655

Finished space • Dowes beach • Sun porch

VIDEO TOUR

ABOUT THIS HOME
Home with Basement for sale in Osterville, MA:
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 romantic patios. Curving stone walls, terraced rock feature gardens, and stone patios complement the entire grounds. Across the river from your 200 feet of waterfront is Long Beach, a pristine barrier stretch of powdery white sand and privacy. The dock enjoys some of the deepest water of any house on thi

$8,625,000

7 beds7.5 baths7,315 sq ft

63 Main St, Osterville, MA 02655

Stone patios • Hidden porches • Dynamic views

FLOOR PLAN

ABOUT THIS HOME
Home with Basement for sale in Osterville, MA:
This meticulously renovated waterfront Cape on the bay is indoor-outdoor living at its finest, where sun-filled interiors meet breathtaking waterfront views. Five plus bedrooms, multiple fireplaces, and a sprawling finished basement provide space for every occasion, while a breakfast nook overlooking the rear landscape sets the tone for relaxed everyday living. With the flexibility to place the primary suite on the first or second floor, the layout adapts effortlessly to any lifestyle. Outside, 1.69 acres of manicured grounds showcase a heated in-ground pool with new bluestone surround, hot tub, fire pit, pool house, and outdoor shower. With multiple lounging areas, every corner of the exte

$5,995,000

5 beds6.5 baths9,645 sq ft

375 Baxters Neck Rd, Marstons Mills, MA 02648

Breakfast nook • Waterfront views • Hot tub

FLOOR PLAN

ABOUT THIS HOME
Home with Basement for sale in Osterville, MA:
Nestled within the prestigious enclave of Seapuit, this architectural masterpiece represents a rare synergy of design and craftsmanship spanning over 5,000SF of meticulously curated space. A collaboration between renowned architect Doreve Nicholaeff & the master builders at Sylvia & Sylvia, the residence is an exercise in sophisticated coastal living. The home is set on a two-acre private oasis, featuring manicured grounds in a serene courtyard setting designed by the acclaimed David Hawk. The main level is anchored by a sumptuous primary suite boasting a state-of-the-art bathroom, a dedicated dressing room, and dual walk-in closets. Upstairs, two additional private suites offer

$3,500,000

4 beds4.5 baths5,049 sq ft

140 Seapuit Rd, Osterville, MA 02655

Dual walk-in closets • Manicured grounds • 2.05 acre lot

ABOUT THIS HOME
Home with Basement for sale in Osterville, MA:
New Driveway Entrance and front yard redesigned!!!! Fall in love the moment you step inside this beautifully renovated home that feels brand new in every way. Sunlight fills the space throughout the day, drawing your eye to tranquil pond views and the surrounding natural beauty that create an immediate sense of calm and privacy. Thoughtfully redesigned with modern amenities, this home offers effortless living both indoors and out. Imagine preparing meals in the outdoor kitchen while overlooking the water, or starting your day in the main-level bedroom with peaceful pond views before stepping onto the deck with your morning coffee. Tucked into a serene setting, yet just minutes to the bouti

$1,675,000

3 beds2.5 baths2,048 sq ft

162 Main St, Osterville, MA 02655

Renovated home • Main-level bedroom • Pond views

Property at 441 Old Mill Rd, Osterville, MA 02655, 2 beds, 2 baths

$735,000

2 beds2 baths2,110 sq ft

441 Old Mill Rd, Osterville, MA 02655

Property at 359 Baxter Neck Rd, Marstons Mills, MA 02648, 5 beds, 7 baths

$6,750,000

5 beds7 baths8,989 sq ft

359 Baxter Neck Rd, Marstons Mills, MA 02648

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than Redfin are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated Sun Aug 30 2026. Neither the listing broker nor Redfin shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. The Broker providing this data believes it to be correct but advises interested parties to confirm any item before relying on it in a purchase decision. All properties are subject to prior sale, changes, or withdrawal. © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

Homes with Basements for Sale in Osterville

There are currently 17 homes with basements for sale in Osterville at a median listing price of $4.2M. 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 83 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, 4 homes have been sold in Osterville. In addition to houses in Osterville, there were also 5 condos, 1 townhouse, and 0 multi-family units 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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