121 properties for sale in Osterville

Welcome to the beautiful village of Osterville on Cape Cod located in the heart of town, close to many stores and restaurants and only 1 mile to Dowses Beach. This newly built home was custom designed by Barnstable Harbor Builders including many high end features such as: quartz counters, Thermador appliances, red oak HW floors and custom trim detail, beadboard ceilings, and crown molding. The home is positioned seamlessly on a large.52 acre lot with a spacious back yard, a brand new vinyl saltwater pool, outdoor shower, a screened in porch, large patio area, and an outdoor pool cabana w/ a bathroom. This home is perfect for those special summer nights on Cape Cod sitting by the pool and relaxing. Each bedroom includes it's own full bathroom including the 1st floor primary suite bedroom. A few other features added by the builder: a whole house generator, gas fireplace, irrigation system, and a 1-year builder warranty as well. Come see your dream home today before it's too late!

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

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

Welcome to the beautiful village of Osterville on Cape Cod located in the heart of town, close to many stores & restaurants & only 1 mile to Dowses Beach. This newly built home was custom designed by Barnstable Harbor Builders including many high end features such as: quartz counters, Thermador appliances, red oak HW floors & custom trim detail, beadboard ceilings, & crown molding. The home is positioned seamlessly on a large. 52 acre lot with a spacious back yard, a brand new vinyl saltwater pool, outdoor shower, a screened in porch, large patio area, & an outdoor pool cabana w/ a bathroom. This home is perfect for those special summer nights on Cape Cod sitting by the pool and relaxing. Each bedroom includes it's own full bathroom including the 1st floor primary suite bedroom. A few other features added by the builder: a whole house generator, gas fireplace, irrigation system, & a 1-year builder warranty as well. Come see your dream home today before it's too late!

Attractive and Custom Straight Ranch 42x24 +14x12 +21x17! 1. Level living features Fireplaced Living room with bay window / 3rd Bedroom or Study/Office/Den with picture window and closet / Custom Kitchen with contemporary cabinets, peninsula, eat-in area, vinyl flooring and 1/2 wall with oak trim overlooking an incredible 1st Floor Family room with entry to 22x14 deck / Family room features Open beamed cathedral ceiling, skylights / custom windows / raised hearth Fireplace, sliders to an oversized deck / Main Bedroom suite with walk-in closet, laundry and private bathroom / 2nd Bedroom with wall to wall carpeting and coat closet / Hallway with pull-down stairs to attic and access to Full bathroom / Full basement under addition / Partially crawl under main house / Generator fired by natural gas / Title V completed / Fenced yard / This home is unique with an Open Floor plan! Close to stores and conveniences

New Price! Rare Osterville Offering: Endless Potential for Developers, and Dreamers: Discover an incredible opportunity in desirable Osterville. Set on a completely level, 1-acre lot abutting Cape Cod Academy and the tranquil Johnson Tree Farm, this property delivers a rare blend of location, versatility, and future upside. Ideally positioned south of Route 28, you are just minutes from main st, Osterville, Dowses Beach, and Crosby Yacht Yard, while enjoying being minutes to Amie's Bakery, Beacon Gardens, Joshua's and Micha's ponds and the Skunknett River Wildlife Sanctuary. The main home presents a charming, flexible 3-bedroom, 2-bathroom layout featuring a finished lower level, offering a fresh canvas to update and reimagine. Peace of mind comes built-in with a newer roof and brand-new heat pumps backed by a 9-year warranty. A true standout of the property is the expansive 24x60 detached garage complete with an office and bathroom. It is ideal for contractors, hobbyists, or car enthu

Back on Market. Opportunity awaits in this coveted Osterville neighborhood. Bring Your Vision to Life With Over 3300 Sq Ft of Living Space. Radiating curb appeal, this home has been lovingly maintained by the same owners since it was built nearly 50 years ago. Set on a double lot, the mature landscaping shines in every season! New central AC, Generator, irrigation, a shed, composite deck and two car garage. Inside, the welcoming main entry leads to a spacious sitting room with bay window, opening into an elegant dining room. The bright kitchen features a skylight, peninsula and wet bar and opens into the living room with beamed ceilings, fireplace and built-in bookshelf. A highlight of the living space is a sun room with vaulted ceiling and window seat. A separate wing of the main floor has 3 bedrooms and 2 full bathrooms. The main level is rounded out by a third full bathroom and laundry closet. Upstairs, there is a massive private suite with full bathroom and its own office. The dry,

This elegant Cape-style residence offers a refined retreat on a sprawling, wooded lot near Osterville Village and Dowses Beach. Defined by bright, voluminous spaces, the home features a stately pillared portico, stone walkways, and classic shingle siding. Inside, the center hall layout leads to a grand living room with a two-story wall of windows and a Palladian arch. This flows into the dining room and a kitchen equipped with granite countertops, a cooktop island, and a sunny breakfast nook. The adjacent family room features custom built-ins and a brick fireplace. The first-flow primary suite serves as a sanctuary with a walk-in closet and en suite bathroom. Upstairs, a mezzanine gallery overlooks the living area, leading to two spacious guest bedrooms. Outside, an expansive rear deck with a vine-covered pergola overlooks the private lawn and an ornamental pond, creating the perfect setting for relaxation. Located minutes from everything Osterville has to offer!

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 welcomes you into a dramatic foyer, setting the tone for the refined interiors that follow. The main living spaces unfold in a thoughtfully designed layout that flows from formal living and family rooms to an elegant dining area with each space inviting connection, comfort, and celebration. At the heart of the home, the chef's kitchen is both striking and functional, anchored by dual oversized islands clad in premium granite, and accompanied by a fireside sitting room that beckons lingering conversation. Adjacent, the spectacular sunroom redefines indoor-outdoor living with a custom crafted bar and

Discover the epitome of luxury living in this custom-designed waterfront estate, featuring breathtaking views of Eel River and Nantucket Sound. Located in the village of Osterville and set on an expansive and beautifully landscaped 2.4-acre lot, this stunning residence features over 8,000 square feet of meticulously crafted living space with rich details, modern comforts and extraordinary views. The grand interiors seamlessly blend with the exquisitely landscaped outdoor spaces, featuring an inground pool, hot tub, spacious pool house, and a substantial private deep-water dock. Upon entering the home, the grand foyer leads you into the magnificent great room with a two-story custom fireplace, where panoramic vistas of the water and breathtaking sunsets set the scene for unforgettable family gatherings as well as effortless entertaining. The generous floor plan also features a refined library, formal dining room, a gourmet kitchen with center island, custom cabinetry and top-of-the-line

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 Cape Cod Escape features 3 bedrooms and 1.5 baths, offering easy single-floor living. Recent updates include fresh interior paint, beautifully refinished hardwood floors with a fresh stain and polyurethane finish, and a brand-new kitchen floor, making this home ready for its next owner to enjoy from day one. Experience the best of Cape Cod living with charming village shops, restaurants, and coastal attractions just moments away

A generational waterfront setting on Crystal Lake with approved Patrick Ahearn plans and a privately owned dock - an exceptionally rare, build-ready opportunity within a stone's throw of Osterville beaches and village center. A truly distinctive offering on the shores of Crystal Lake in one of Osterville's most coveted and tightly held neighborhoods. With direct lake frontage, a privately owned dock, and approved architectural plans by Patrick Ahearn, one of New England's most celebrated residential architects, this is a rare opportunity to create a refined waterfront residence with both architectural pedigree and long-term value. Ideally positioned for the best of Osterville living, the property offers the uncommon luxury of easy access to the Wianno/Sea View Beach (.2 mi), Dowses Beach (.3 mi), and Osterville Village (.8 mi), placing iconic beaches, village amenities, and daily conveniences all within easy reach. The combination of waterfront privacy and exceptional proximity is incr

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 welcomes you into a dramatic foyer, setting the tone for the refined interiors that follow. The main living spaces unfold in a thoughtfully designed layout that flows from formal living and family rooms to an elegant dining area with each space inviting connection, comfort, and celebration. At the heart of the home, the chef's kitchen is both striking and functional, anchored by dual oversized islands clad in premium granite, and accompanied by a fireside sitting room that beckons lingering conversation. Adjacent, the spectacular sunroom redefines indoor-outdoor living with a custom crafted bar and

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

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

Welcome to the beautiful village of Osterville on Cape Cod located in the heart of town, close to many stores and restaurants and only 1 mile to Dowses Beach. This newly built home was custom designed by Barnstable Harbor Builders including many high end features such as: quartz counters, Thermador appliances, red oak HW floors and custom trim detail, beadboard ceilings, and crown molding. The home is positioned seamlessly on a large.52 acre lot with a spacious back yard, a brand new vinyl saltwater pool, outdoor shower, a screened in porch, large patio area, and an outdoor pool cabana w/ a bathroom. This home is perfect for those special summer nights on Cape Cod sitting by the pool and relaxing. Each bedroom includes it's own full bathroom including the 1st floor primary suite bedroom. A few other features added by the builder: a whole house generator, gas fireplace, irrigation system, and a 1-year builder warranty as well. Come see your dream home today before it's too late!

Legacy, Lifestyle and 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 coastal legacy. This waterfront estate offers 1.78 acres of private grounds, a beautifully preserved five-bedroom residence, and a substantial deep-water dock with direct access to Nantucket Sound-accommodating six or more vessels with ease. Inside, the home exudes understated charm with a seamless connection to outdoor living-screened porch, expansive deck, and water views from most rooms. A welcoming main-level primary suite with adjoining study anchors the floor plan, while the heart of the home features a stone fireplace, an open-concept kitchen, and a screened porch that opens to an expansiv

In the heart of Wianno. One-level living where it counts. This 4-bed, 3.5-bath Osterville home sits in one of the Cape's most walkable, sought-after locations, moments from Dowses Beach and Main Street's shops and restaurants. Inside, it lives like new: gleaming hardwood floors, crown molding, and detailed wainscoting throughout. The first-floor primary suite means single-level living without giving up scale. A fireplace anchors the open living area, built for both quiet nights and full-house gatherings. The kitchen carries the same finish level throughout the whole home, with high-end appliances and detailed cabinetry designed for real entertaining, not just photos. Outside, the bluestone patio functions as a second living room: a pergola, built-in gas grill, and custom gas fire pit make three-season (and beyond) living effortless. Practical luxury runs underneath it all. Geothermal heating and cooling keep utility costs down year-round, and the attached heated garage adds protected p

Set behind the gates of Oyster Harbors, Cape Cod's most exclusive private golf and waterfront community, this extraordinary waterfront estate offers an exceptional blend of architectural elegance, privacy, and coastal luxury. Perfectly sited on 1.65 acres along the water's edge, the property enjoys sweeping water views, a deep-water dock, an in-ground pool, and meticulously landscaped grounds designed for both grand entertaining and quiet moments of retreat. Inspired by the timeless character of a European country estate, the residence encompasses 7,157 square feet of thoughtfully designed living space where sophisticated craftsmanship meets effortless comfort. A dramatic foyer introduces the home's remarkable interior, opening to an impressive great room with soaring vaulted ceilings, architectural columns, a custom fireplace, and expansive walls of glass that frame the ever-changing waterfront. Designed for both everyday living and elegant entertaining, the sun-filled dining room cap

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 plenty

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 u0026 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 bea

Delightful first floor unit in sought after Osterville village location! Nestled in the heart of beautiful Osterville village and walking distance to Fancy's Market, Library, Church, Restaurants and Fabulous Boutique shops. Stroll to the resident only desirable Dowses beach too! This is a wonderful opportunity to live and enjoy one floor living where everything is at your fingertips.

Delightful first floor unit in sought after Osterville village location! Nestled in the heart of beautiful Osterville village and walking distance to Fancy's Market, Library, Church, Restaurants and Fabulous Boutique shops. Stroll to the resident only desirable Dowses beach too! This is a wonderful opportunity to live and enjoy one floor living where everything is at your fingertips

Architecturally stunning and beautifully appointed, this exceptional residence is set within one of Cape Cod

Beautifully renovated and thoughtfully improved, 23 u0026 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. Addit

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

Tucked within the gated enclave of Oyster Harbors, 93 Oyster Way blends timeless coastal elegance with modern luxury. Designed for both everyday living and entertaining, the home offers sun-filled interiors with vaulted ceilings and rich hardwood floors. Formal living and dining rooms provide inviting gathering spaces with serene backyard views. At the heart of the home, the chef's kitchen features custom wood cabinetry, granite countertops, a large center island, and premium Wolf and Sub-Zero appliances. An adjacent breakfast nook enhances the kitchen's functionality, with direct access to the family room and screened porch for seamless indoor-outdoor living. The primary suite offers a private retreat with dual walk-in closets, patio access, and a spa-like bath with soaking tub and walk-in shower. Additional bedrooms, en-suite baths, and a home office add flexibility. A finished lower level includes a gym, office, wine cellar, and ample storage. Outdoors, a brick patio and stone wall

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 Cape Cod Escape features 3 bedrooms and 1.5 baths, offering easy single-floor living. Recent updates include fresh interior paint, beautifully refinished hardwood floors with a fresh stain and polyurethane finish, and a brand-new kitchen floor, making this home ready for its next owner to enjoy from day one. Experience the best of Cape Cod living with charming village shops, restaurants, and coastal attractions just moments away

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 & 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 units

Nestled along the sparkling shores of North Bay in the heart of Osterville, this exceptional Waterfront Estate delivers timeless beauty and relaxed elegance. Wake each morning to sweeping water views and ocean breezes, step onto your boat from the Substantial Dock. Featuring a Primary Suite and Guest Suite both on the 1st Floor, the residence is thoughtfully designed to blend coastal charm with modern comfort, with sun-filled living spaces, expansive windows, and seamless indoor-outdoor flow perfect for entertaining or quiet seaside relaxation. Waterfront Chef's Kitchen with Cathedral Ceiling, Living Rooms, Dens, separate living quarters complete with a Kitchen over the 3-Bay Garage. Step outside to your private waterfront oasis, where launching a kayak at sunrise, enjoying afternoon boating on North Bay, or taking sunset walks with the dog, every day feels like a vacation. Located just moments from Osterville Village's boutiques, restaurants, and marinas