Osterville Homes for Sale

Tucked away in the heart of Wianno, this charming waterfront home enjoys exceptional privacy and scenic views of Neck Pond and the Wianno Golf Course.Set on .73 of an acre, this property has been held by the same family for generations and is now ready for its next chapter. Ideally located close to Dowses Beach and Osterville village, this home is the perfect Cape Cod get-away with room to

Gene Orloff Sotheby's International Realty

A custom home in the quaint seaside Village of Osterville! Perfectly nestled alongside Crosby Boat Yard, Nauticus Marina, Oyster Harbors Marina, The Chart Room and well-known West Bay, you will find this top of line crafted 4 bedroom, 3.5 bathroom home. Hand-selected flooring and natural lighting fill the open-concept entertaining spaces and private rooms, creating an elevated living experience.

Cynthia Houlihan Berkshire Hathaway HomeServices Robert Paul Properties

From the moment you arrive, you're greeted by a stone circular driveway and a large front porch that warmly says, ''Welcome--please come in!''Once inside, you immediately notice the home's timeless elegance combined with the comfort needed for everyday living. Each room is perfectly sized, and the thoughtful layout and seamless flow from one room to the next make this home ideal for family

Julie White William Raveis Real Estate & Home Services

Defined by its water views, generous grounds, and multiple outdoor living spaces, 30 Cockachoiset (''Dillon House'') offers a welcoming coastal retreat designed for gathering, entertaining, and enjoying life by the water. The main level is thoughtfully designed with an open floor plan anchored by a well-equipped kitchen that flows seamlessly into a sun-filled breakfast nook and sitting area,

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

Tucked within the gated enclave of Oyster Harbors, 93 Oyster Way blends coastal elegance with modern luxury. Sunlit interiors feature vaulted ceilings, hardwood floors, and inviting living and dining spaces overlooking a private backyard. The chef’s kitchen offers custom cabinetry, granite countertops, a large island, and premium Wolf and Sub-Zero appliances, opening to a family room and screened

Kelly Crosby LandVest, Inc.

Defined by sweeping water views, expansive grounds, and exceptional outdoor living spaces, 30 Cockachoiset (“Dillon House”) offers a welcoming coastal retreat designed for gathering and entertaining. The open-concept main level features a well-equipped kitchen flowing into a sun-filled breakfast nook and sitting area surrounded by walls of windows overlooking the water. Additional highlights

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

Set on 3.4 acres of meticulously landscaped grounds in Osterville's coveted Seapuit neighborhood, this magnificent Colonial estate offers the best of modern living on a grand scale. The five-bedroom main residence showcases architectural splendor and attention to detail throughout, with seamless access to expansive outdoor living spaces. Rivaling a private resort, the grounds boast rolling lawns,

Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

Set on an exceptionally oversized 2.94-acre corner parcel within Osterville's highly sought-after Seapuit neighborhood, this newly built residence offers a rare combination of privacy, scale, and resort-style amenities, just minutes from the heart of Osterville Village. Surrounded by established homes in a refined residential setting, the property presents a compelling opportunity for turnkey

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

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

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

A custom home in the quaint seaside Village of Osterville! Perfectly nestled alongside Crosby Boat Yard, Nauticus Marina, Oyster Harbors Marina, The Chart Room and well-known West Bay, you will find this top of line crafted 4 bedroom, 3.5 bathroom home. Hand-selected flooring and natural lighting fill the open-concept entertaining spaces and private rooms, creating an elevated living experience.

Cynthia Houlihan Berkshire Hathaway HomeServices Robert Paul Properties

This beautiful new Osterville home is perfectly situated in Wianno, just minutes from village shops, restaurants, and Dowses Beach. With its open floor plan, white oak hardwood floors, and exceptional attention to detail, this charming property offers coastal living at its finest.The stunning kitchen features quartzite countertops, Viking appliances, and a large island with generous seating and

Gene Orloff Sotheby's International Realty

Located in the heart of Osterville, one of Cape Cod’s most sought-after seaside villages along Nantucket Sound, 12 Cockachoiset - known as the iconic “Windmill House” - blends coastal charm with distinctive architectural character. Recognized for its two-story windmill adorned with seaside murals, the home features water views from a private balcony and inviting indoor-outdoor living spaces

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

Charming one-level ranch offered for the first time in generations, ideally located in the heart of Osterville Village. Only 1.5 miles to beautiful Dowses Beach, a short 8 minute drive to sought-after Craigville Beach, and a quick 0.4 miles to the clear waters of Joshua Pond. This inviting "Cape Cod Escape" features 3 bedrooms and 1.5 baths, offering easy single-floor living and endless

Chelsea McLaughlin RE/MAX Legacy

Just in time for summer! Move right into this newly remodeled, sun-filled open-concept ranch with one-car garage and oversized shed in desirable Osterville Heights! Set on a spacious, partially fenced private yard, it's perfect for outdoor games, barbecues, and relaxing with family and friends. Recent upgrades include enhanced landscaping, fresh paint, Canadian white oak flooring throughout,

Donna Christopher Sotheby's International Realty

Property is being offered via Real Estate Auction on Friday, June 26th at 11am on-site. The actual selling price will be determined auction day. List price/estimated value seen is set at the real estate tax assessment. Pre-auction offers must be presented on the auction P&S and are subject to seller confirmation. 10% Buyer's Premium applies. Re: The Estate of Beth E. Higgins. 2,076+/- sf 3BR, 2BA

Justin Manning JJManning Auctioneers

Discover the charm and convenience of this lovingly maintained ranch-style home, perfectly designed to meet all your needs. Adding to its appeal, this home is just minutes away from the idyllic coastal Main Street of Osterville Village with its charming boutiques, delightful cafes, and quaint seaside allure. The home's inviting foyer is the perfect introduction to the warmth and character that

Karen Rezendes Kinlin Grover Compass

This 4 bedroom home, nestled in one of Osterville's most coveted neighborhoods, is perfect for both relaxation and entertaining, offering a blend of comfort and space for creating unforgettable memories. The fantastic layout connects the sun-filled living room, kitchen, and dining area, with a slider leading to a deck featuring an awning for shade. There's also a spacious family room with gas

Amanda Kundel Kinlin Grover Compass

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

Shaelyn Hegarty Frank A Sullivan Real Estate

A mid-19th-century Greek Revival, believed to be the birthplace of Captain William Bradford Parker and later home to Samuel Hallett -- both tied to Osterville's historic maritime corridor along Main Street. The property reflects the success of maritime captains - there's a reason Osterville was once described as ''a place where retired sea captains can live like gentlemen.'' You feel that here.

Karen Lilly Property Cape Cod

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

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 2-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. Inside, refined architectural detail

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

Exquisite Waterfront Estate in Exclusive Oyster Harbors: Experience the pinnacle of coastal luxury with this magnificent Cape Cod waterfront estate, nestled in the prestigious gated community of Oyster Harbors. Boasting 450 feet of pristine water frontage with a private beach and breathtaking views over Cotuit Bay and North Bay, this property offers spectacular sunsets, an elegant coastal

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

Summer is in the Air! Welcome 177 Bayview Circle and Osterville Village. Enjoy sunbathing and swimming at Dowses beach, go clamming off Bridge Street, stroll to Fancy's Market and Main St for dining, shopping, ice cream and more. This lovely property is also near town way to water, Osterville Library and Post Office, Crosby Yacht, East Bay, the farmers market and private golf clubs. Come see this

Kathleen Craig Berkshire Hathaway HomeServices Robert Paul Properties

Welcome to ''Point House,'' an extraordinary 5.98-acre waterfront estate set on a private peninsula overlooking the shimmering waters of West Bay. Surrounded by breathtaking natural beauty, this rare offering pairs sweeping water views with exceptional privacy, highlighted by expansive lawns, curated gardens, a private sandy beach, and a substantial deep-water dock with direct access to Nantucket

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

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.

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

Nestled in the heart of Osterville Village, this 3-bedroom, 3-bath home perfectly blends charm with modern updates in one of Cape Cod's most sought-after locations. The backyard is an entertainer's paradise: just wait until you see this spectacular outdoor kitchen with stainless steel appliances, fire pit, and pergola. A partially finished basement provides extra living space, and an oversized

Sarah Harrington Kinlin Grover Compass

This elegant Cape-style residence offers a refined retreat just minutes from everything Osterville Village has to offer. Set on a sprawling, wooded lot, the home's classic exterior is highlighted by a stately pillared portico and a winding stone walkway that create distinguished curb appeal.The interior opens into a center hall layout where architectural columns frame a grand living room defined

Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

RARE opportunity for a gorgeous first floor unit in Osterville's desirable Village Square. Completely renovated and move in ready two bedroom two bath condo in the heart of Osterville village. Light and airy open floor plan with numerous windows and ample natural light. Features include all new kitchen with luxury appliances, gorgeous marble and natural stone tiled bathrooms, white oak flooring,

Gregory W Nowak Craigville Realty Co

This beautifully updated Osterville Cape, set on a private cul-de-sac, offers move-in-ready living with a thoughtfully curated interior that reflects its coastal charm. Bright, spacious rooms feature vaulted ceilings, skylights, and abundant natural light, while five high-efficiency ductless A/C units ensure comfort throughout the summer months.The first-floor primary suite includes a walk-in

Margo Pisacano Margo & Company

Legacy, Lifestyle & 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

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

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

Kimberly Gazal Santos Property Cape Cod

Osterville opportunity. Situated on 1.4 acres and abutting conservation land, this 2-bedroom, 2-bath raised ranch offers endless possibilities. Located just moments from Osterville’s charming village center, you’ll enjoy easy access to boutique shopping, delightful dining, and local favorite, Dowses Beach. Whether it’s a thoughtful home renovation or a complete reimagining to unlock the full

Diane Boudreau Kinlin Grover Compass

Builder/Investor Opportunity in Osterville with Expansion Potential!Charming 3-bedroom, 1-bath home on a spacious 0.64-acre lot in one of Osterville's most desirable locations. Features include a sunroom, garage, additional shed, private backyard, and newer boiler, gas furnace and heat pump.Conveniently located near Dowses and Craigville Beaches and close to Osterville Main Street shops and

Kami Dimitrova EXIT Cape Realty

South of Route 28 in Osterville village, this inviting property offers an outstanding opportunity to secure your place in one of the area's most sought-after locations. Just 1 mile from Main Street, you'll enjoy easy access to restaurants, shops, beaches and everyday conveniences that make village living so special. Inside the home features a bright living room with vaulted ceilings, a first

Adam Marks Berkshire Hathaway HomeServices Robert Paul Properties