121 properties for sale in Osterville

Exceptional 3-BR Family/Vacation Home in Osterville: Nestled in a well-maintained neighborhood in the desirable village of Osterville. This spacious and inviting 2116 sf 3 BR home would be an ideal primary residence or your Cape Cod getaway retreat. Beautiful hardwood floors throughout the main floor. Upstairs-2 spacious guest bedrooms and a loft/study room. This home features an impressive primary suite with a walk-in closet and ample storage. The backyard highlights a large deck perfect for outdoor living and entertaining. An attached 2 car (heated) garage. An unfinished basement with great ceiling height for excellent flexibility or future expansion. Nature lovers will appreciate the exceptional location. At the end of the cul-de-sac you're at The Skunknett River Wildlife Sanctuary. Explore 147 acres with marked trails, vernal pools and local wildlife right at your doorstep. Conveniently located 1.8 mi to the village, 3.2 mi to Dowses Beach.03 to Cape Cod Academy. This home comes co

Monthly condo fee includes heat, hot water and electricity! This charmer offers contemporary style in a compact space, featuring a first-floor bedroom, full bath, and loft accessed by a distinctive spiral staircase. A private patio provides a great spot to relax and enjoy the outdoors. A fresh coat of paint and a few personal touches will bring out its full potential. Community amenities include a swimming pool and three coin-operated laundry rooms. Conveniently located just off Route 28, with easy access to Osterville Village, Hyannis, and Mashpee Commons. A delightful opportunity to create your own Cape Cod getaway! Buyers and agents, to verify all information contained herein. Taxes may vary depending on residency status

The right address can give you the best of both worlds—privacy at home and Village life just minutes away. Osterville's Starboard Lane, winding along the western shore of the Bumps River, is one of those special places. Known for gracious homes, substantial parcels, and a wonderfully private setting, it remains one of the Village's most desirable enclaves. Set on 1.68 acres, 420 Starboard Lane offers four bedrooms and 2,636 square feet of comfortable living space, with high ceilings, generous gathering areas, and a floor plan well suited to relaxed Cape Cod living. A detached two-car garage with unfinished space above adds another dimension, offering intriguing possibilities for the future. Here, there is room to breathe without giving up the restaurants, shops, beaches, and everyday pleasures that make Osterville so appealing. Private. Prestigious. Close to everything that matters. Opportunities to own this much land in such a desirable Osterville setting don't come along often. Pleas

Incredible value at this new price in Osterville Heights! Move right into this sun-filled, open-concept ranch with one-car garage and oversized shed set on a private and spacious partially-fenced park-like backyard perfect for adding a potential pool, outdoor entertaining, barbecues, lawn games and relaxing with family and friends. New improvements include enhanced landscaping, fresh paint, new Canadian white oak floors throughout, 3 new Rovsun mini-split A/C units, tile floors in bathrooms, a new Electrolux ventless stackable washer/dryer in hallway bath, new vanity/toilet in the second bath and an new electric heated fireplace in the spacious bedroom. The full lower level offers excellent expansion possibilities, while the generous backyard provides additional opportunities to create your ideal Cape Cod retreat. Whether you're looking for a year-round home, vacation getaway, or investment opportunity, this property checks all the boxes. Conveniently located just minutes from Ostervil

Beautifully renovated and thoughtfully designed by an Osterville builder, this custom ranch offers the ease of one-level living with the elevated finishes of a designer home including 3 beds with a large master suite and 3 full baths each one has its own unique design. The light-filled interior features a cathedral shiplap ceiling, Phillip Jeffries wallcoverings, extensive marble, custom cabinetry and a stunning kitchen appointed with premium Viking and Miele appliances. Marble finishes continue throughout the beautifully designed baths. The walk-out lower level adds valuable bonus living space, ideal for a family room, home office, gym or guest area along with a 3 season screened in porch. Fresh cottage-inspired details and a sophisticated coastal palette complete the transformation. For buyers seeking a move-in-ready Osterville home, renovated ranch, first-floor living or the feel of new construction, 31 Jason's Lane delivers timeless Cape Cod style with a designer's touch

Located in the heart of Wianno, this exceptional new construction home offers the ultimate Cape Cod lifestyle-just moments to the village and beach. Blending classic Cape architecture with modern luxury, this home is designed for everyday living and effortless entertaining. Exquisite millwork, high ceilings, white oak floors, beautifully appointed built-ins, marble throughout, Marvin windows and doors -it's the finishes that set this home apart. The foyer opens to a gourmet kitchen with generous island, custom cabinetry, pantry, and Sub-Zero refrigerator. The light-filled living and dining spaces flow seamlessly to a beautifully landscaped private yard with ipe deck, creating an inviting setting for indoor-outdoor living. An adjoining bar enhances the home's effortless entertaining appeal, while the main level ensuite is perfect for guest or office space. Upstairs, the layout includes three additional bedrooms, luxurious bathrooms, a built-in reading bench, laundry room, and a grand fa

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 this stretch, allowing for multiple boats and other recreational craft. The quaint conclusion to this fairytale setting is a larger detached apartment over the garage. The square footage of 9,011, seven bedrooms and seven-and-a-half bathrooms speak for themselves. This treasure is waiting for you

Perfectly situated within a 5-minute drive of the beach, Main Street Osterville shopping and restaurants, and Route 28, which opens all of the Cape to exploration and fun, this gracious 4-bed, 4-bath home offers a peaceful retreat where timeless coastal charm meets effortless outdoor living. Set among mature trees and beautifully groomed landscaping, the wooded setting creates privacy and a sense of escape, while the inviting deck and three-season screened porch extend the living space into nature. Inside, glowing hardwood floors and abundant windows fill the home with warmth and natural light. Soaring ceilings and beautiful exposed beams add a sense of grandeur, while multiple fireplaces, framed by timeless brick and distinctive wood mantels, create cozy gathering spaces throughout. The expansive kitchen shines with polished granite countertops, bright white cabinetry, stainless steel appliances, including a double oven and gas range, blending beautifully with the home

Osterville Village Cottage on South: A rare offering in the heart of Osterville Village. Renovated duplex townhome just one block from Main Street and steps from Joshua's Pond. One of two residences in this private enclave- a setting that delivers quiet, space, and exclusivity. An arbor marks the front approach, with a fenced front yard and a private side entrance. Shell driveway with parking for 2 cars + an assigned guest spot. Beyond the door, a beautiful private backyard and a generous south-facing deck makes for a peaceful private retreat. Inside, light pours through the spacious living room with two skylights and beautiful hardwood floors. Well-appointed Kitchen w/granite counters, stainless appliances and an eat- up breakfast bar. Whether as a Cape Cod retreat, an income producing property, or a year-round residence, the Osterville Cottage on South delivers - close to Dowses Beach, village shops and restaurants. Companion unit also available. Seller will consider selling both uni

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 includes a kitchenette, 1/2 bath, outdoor shower, bunk bed room, family room with queen bed and day bed. This lower level is very comfortable with full sized windows and a slider sleeps 5 with easy access through the slider to the flat back yard and enclosed outside shower. The lot is. 4 acres and has plent

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

Privately set behind a gated drive on two acres along Eel River, this remarkable Osterville waterfront estate commands a rare vantage point overlooking the river and Nantucket Sound. The architecture is designed around the setting, with broad expanses of glass, soaring coffered ceilings, fine millwork, and a succession of light-filled spaces oriented toward the water. The main level brings together a gracious chef's kitchen, a dramatic great room overlooking the water, and a luxurious primary suite with its own media room. The residence unfolds across three levels, with a graceful stairway connecting each floor. The second level offers three additional bedroom suites, while the third floor creates a more intimate retreat, with a spacious waterfront sitting room opening to a private balcony, and a fifth bedroom along with two bonus rooms. The finished lower level is dedicated to recreation, with a theater accommodating 20 and a substantial game and media room. Beyond the main residence,

FIRST FLOOR RENOVATED CONDO in the heart of Osterville Village! Enjoy the best of village living with an easy walk to Osterville's shops, restaurants, and local amenities. This tastefully renovated condo with new floors, kitchen and baths offers two generously sized bedrooms and two full bathrooms. The spacious living room features a cozy fireplace and flows beautifully into the dining area, creating an inviting space for everyday living and entertaining. Sliders lead to a covered patio providing a separate entrance as well as the perfect spot to relax and enjoy the outdoors. Head to Joshua's Pond or Dowses Beach for a swim or relaxing by the water. Truly easy one level living. Don't miss this opportunity to own in one of Cape Cod's most desirable locations!

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 upgraded cabinets, granite counters and breakfast bar plus half bath. The primary bedroom is on the first level offering a private ensuite bath with Shower and separate spa tub, plus walk in closet! Perfect! hardwood floors throughout and on both levels. 2 bedrooms a d full bath complete the 2nd floor. The partially finished basement provides laundry and extra recreation or home office space. 1 car attached garage completes the property. Minutes to Osterville village center for dining, boutique shopping, galleries and more. 2.1 miles to stunning Dowses Beach!

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 of this special property. The main living spaces are designed for comfort and gathering, highlighted by a generous great room with a custom fireplace that opens to a covered patio and private side yard. A well-appointed kitchen adjoins the dining room, while the first floor also includes a bedroom with attached sitting room, laundry, and multiple inviting outdoor living areas. Upstairs, the primary suite is anchored by its own fireplace, private bath, and walk-in closet. An additional sitting room with balcony access and a third bedroom complete the second level, offering flexible space for guests

Presiding over West Bay, this extraordinary waterfront estate spans 2.35 pristine acres with breathtaking views in an unrivaled location. A park-like driveway winds through manicured grounds with sculpted boxwood hedges and vibrant hydrangeas, creating a sense of privacy and grandeur as you approach the residence. A private dock provides immediate access to West Bay and Nantucket Sound, while the waterside swimming pool and pool house create a resort-like atmosphere. Inside, the residence showcases fine architectural millwork, soaring ceilings, limestone flooring, and six fireplaces across its gracious living spaces. The intuitive layout centers around an impressive main living room where French doors trace the water side of the home, allowing natural light to pour inside while framing panoramic views. Cooking and daily living center around the gourmet kitchen, which features a custom wood center island with seating, professional-grade appliances, and natural stone countertops. Excepti

Privately set behind a gated drive on two acres along Eel River, this remarkable Osterville waterfront estate commands a rare vantage point overlooking the river and Nantucket Sound. The architecture is designed around the setting, with broad expanses of glass, soaring coffered ceilings, fine millwork, and a succession of light-filled spaces oriented toward the water. The main level brings together a gracious chef's kitchen, a dramatic great room overlooking the water, and a luxurious primary suite with its own media room. The residence unfolds across three levels, with a graceful stairway connecting each floor. The second level offers three additional bedroom suites, while the third floor creates a more intimate retreat, with a spacious waterfront sitting room opening to a private balcony, and a fifth bedroom along with two bonus rooms. The finished lower level is dedicated to recreation, with a theater accommodating 20 and a substantial game and media room. Beyond the main residence,

Welcome to 51 Falling Leaf Lane, a charming two-bedroom, two-bath ranch tucked away on a peaceful dead-end street in the heart of Osterville. Offering privacy, comfort, and convenience, this inviting home is an ideal Cape Cod retreat or year-round residence. The thoughtfully designed floor plan provides an easy flow between living spaces, with plenty of room to gather and entertain. Bright, welcoming interiors create a warm and comfortable atmosphere, while two spacious bedrooms offer comfortable accommodations for family or guests. A versatile bonus room provides added flexibility and can be used as a home office, den, hobby space, or occasional guest room. Enjoy the peaceful outdoor setting surrounded by mature trees and the natural beauty of Cape Cod. Just minutes from Osterville Village, beautiful beaches, restaurants, shopping, conservation areas, and recreational opportunities, this home offers the ideal combination of tranquility and convenience. A wonderful opportunity to enjoy

Incredible value at this new price in Osterville Heights! Move right into this sun-filled, open-concept ranch with one-car garage and oversized shed set on a private and spacious partially-fenced park-like backyard perfect for adding a potential pool, outdoor entertaining, barbecues, lawn games and relaxing with family and friends. New improvements include enhanced landscaping, fresh paint, new Canadian white oak floors throughout, 3 new Rovsun mini-split A/C units, tile floors in bathrooms, a new Electrolux ventless stackable washer/dryer in hallway bath, new vanity/toilet in the second bath and an new electric heated fireplace in the spacious bedroom. The full lower level offers excellent expansion possibilities, while the generous backyard provides additional opportunities to create your ideal Cape Cod retreat. Whether you're looking for a year-round home, vacation getaway, or investment opportunity, this property checks all the boxes. Conveniently located just minutes from Ostervil

Presiding over West Bay, this extraordinary waterfront estate spans 2.35 pristine acres with breathtaking views in an unrivaled location. A park-like driveway winds through manicured grounds with sculpted boxwood hedges and vibrant hydrangeas, creating a sense of privacy and grandeur as you approach the residence. A private dock provides immediate access to West Bay and Nantucket Sound, while the waterside swimming pool and pool house create a resort-like atmosphere. Inside, the residence showcases fine architectural millwork, soaring ceilings, limestone flooring, and six fireplaces across its gracious living spaces. The intuitive layout centers around an impressive main living room where French doors trace the water side of the home, allowing natural light to pour inside while framing panoramic views. Cooking and daily living center around the gourmet kitchen, which features a custom wood center island with seating, professional-grade appliances, and natural stone countertops. Excepti

Incredible value at this new price in Osterville Heights! Move right into this sun-filled, open-concept ranch with one-car garage and oversized shed set on a private and spacious partially-fenced park-like backyard perfect for adding a potential pool, outdoor entertaining, barbecues, lawn games and relaxing with family and friends. New improvements include enhanced landscaping, fresh paint, new Canadian white oak floors throughout, 3 new Rovsun mini-split A/C units, tile floors in bathrooms, a new Electrolux ventless stackable washer/dryer in hallway bath, new vanity/toilet in the second bath and an new electric heated fireplace in the spacious bedroom. The full lower level offers excellent expansion possibilities, while the generous backyard provides additional opportunities to create your ideal Cape Cod retreat. Whether you're looking for a year-round home, vacation getaway, or investment opportunity, this property checks all the boxes. Conveniently located just minutes from Ostervil

Set on 1.2 acres in an exceptional location along the highly desirable south-facing side of Starboard Lane, this Osterville property offers a rare opportunity to renovate, reimagine, or create a custom dream home in one of the village's most sought-after settings. The existing three-bedroom, three-bath residence enjoys partial water views and provides an appealing foundation for a buyer, builder, or investor looking to take full advantage of this prime parcel. The first floor features a spacious primary suite with high ceilings and an en-suite bath, along with an open-concept kitchen and den designed for comfortable everyday living. A second full bath includes a steam shower and distinctive Sherle Wagner-designed sink. A gracious living room with a working fireplace and an enclosed, winterized porch complete the main level. Upstairs are two additional bedrooms, a full bath, and a dedicated laundry room with space for a washer and dryer. A detached two-car garage is located at the rear

The Cottage- Osterville Village. A rare offering in the heart of Osterville Village: a renovated duplex townhome just one block from Main Street and steps from Joshua's Pond. One of two residences in this private enclave- a setting that delivers quiet, space, and exclusivity. An arbor marks the front approach, with a fenced front yard and a private side entrance. Beyond the door, a private backyard, a shell driveway and a generous south-facing deck. A small waterfall, and a private patio under a pergola draped with trumpet vines, completes the outdoor space. A true sanctuary for the nature lover. Inside, the light pours through a cathedral skylit living room anchored by a gas fireplace and beautiful hardwood floors. Whether as a Cape Cod retreat, an income producing property, or a year-round residence, The Cottage delivers - close to Dowses Beach, village shops and restaurants. Companion unit also available. Seller will consider selling both units together. Inquire for details. Offered

Set on 2.35 beautifully landscaped acres along Eel River, this exceptional Osterville waterfront estate enjoys western exposure, sweeping water views, and a substantial deep-water dock with direct access to Nantucket Sound. The setting is defined by an extraordinary combination of privacy, scale, and waterfront amenities, creating a rare sense of arrival and an exceptional connection to the water. The six-bedroom main residence offers approximately 7,000 square feet of living space, with a gracious floor plan designed to take full advantage of the setting. From the grand foyer, panoramic water views immediately draw the eye through the home and toward the expansive grounds and waterfront beyond. The main level offers generous living and entertaining spaces, while the second floor features a spacious primary suite with fireplace, walk-in closet, and private bath, along with five additional bedrooms. The lower level includes a recreation room, exercise room, and abundant storage, with an

Perfectly situated within a 5-minute drive of the beach, Main Street Osterville shopping and restaurants, and Route 28, which opens all of the Cape to exploration and fun, this gracious 4-bed, 4-bath home offers a peaceful retreat where timeless coastal charm meets effortless outdoor living. Set among mature trees and beautifully groomed landscaping, the wooded setting creates privacy and a sense of escape, while the inviting deck and three-season screened porch extend the living space into nature. Inside, glowing hardwood floors and abundant windows fill the home with warmth and natural light. Soaring ceilings and beautiful exposed beams add a sense of grandeur, while multiple fireplaces, framed by timeless brick and distinctive wood mantels, create cozy gathering spaces throughout. The expansive kitchen shines with polished granite countertops, bright white cabinetry, stainless steel appliances, including a double oven and gas range, blending beautifully with the home's classic chara

Architecturally stunning and beautifully appointed, this exceptional residence is set within one of Cape Cod's premier resort communities. Perfectly sited on 2.44 acres, the elegant home combines exquisite craftsmanship and refined detailing with a warm, inviting sense of style and ambiance. Nearly 5,000 square feet of custom-designed living space flows seamlessly from one room to the next, creating an ideal setting for both sophisticated entertaining and relaxed everyday living. The spacious living room is designed for both grand-scale entertaining and comfortable everyday living, featuring a handsome wet bar and seamless access to the light-filled sunroom overlooking the resort style pool. The dining area provides an inviting setting for formal gatherings, while the beautifully appointed kitchen with a generous center island, granite countertops, and custom backsplash, serves as the heart of the home. Refined millwork and thoughtful architectural details throughout add a timeless sen

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 beach. 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 modern living with an eat-in chef's kitchen equipped with professional-grade appliances, seamlessly blending with a fireplaced living area. Oversized windows and glass doors line the waterside of the home, framing spectacular vistas and effortlessly connecting to the outdoors where a covered wooden deck

Beautifully renovated and thoughtfully improved, 23 and 27 Swift Avenue is a rare two-parcel Osterville offering totaling approximately 1.11 acres, just moments from Osterville Village. Set on approximately.66 acre, the charming 3-bedroom residence is conveyed with an adjoining approximately.45-acre parcel, creating exceptional privacy and intriguing future potential. Recent improvements include a new roof and brand-new 4-bedroom septic system. Inside, sun-filled living spaces feature warm wood floors, classic Cape character and a beautifully appointed kitchen flowing to the dining and family areas with direct access to the expansive backyard. A first-floor primary suite with renovated bath, separate living room and powder room complete the main level, with two bedrooms and full bath upstairs. Outdoors, enjoy mature landscaping, expansive lawns, oversized spa, outdoor shower and stone fire pit. A detached 2-car garage features temperature/humidity controls and epoxy flooring. Additiona

Move-in ready and offered for the first time in generations, this charming one-level ranch is ideally located in the heart of Osterville Village. Just 1.5 miles to beautiful Dowses Beach, an 8-minute drive to sought-after Craigville Beach, and only 0.4 miles to the crystal-clear waters of Joshua Pond. This inviting

Luxurious Oyster Harbors residence with Deeded Beach Rights! This architecturally designed, luxury built home by Bayside Building features impressive exterior roof lines and extensive millwork throughout. The quality of construction is readily evident from the moment you arrive at the residence. The 1st floor features an expansive 2-story living room with a gas fireplace, an adjacent dining room, a gourmet kitchen w/ center island & a sep. Wet bar area, an expansive master bedroom suite with a luxurious master bathroom, a sep. Guest suite, laundry room, half bath, and an expansive screened-in porch which also has a gas fireplace. The 2nd floor features 2 bedrooms, a bathroom, and a large family room. The professionally maintained grounds have numerous hydrangeas, mature trees for privacy, a heated pebble-tech pool and spa, a pool house with a half bath and laundry. There is a 2-car att. Garage, a front open porch, and a generator. In addition, this property benefits from deeded beach a