Osterville MA Homes for Sale

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Type:
Single Family
Sq.Ft.:
1,856
Status:
Active
Beds:
3
Lot size:
0.31 Acres
Year built:
1953
Baths:
2.00
MLS#:
22500443

ADDITIONAL INFORMATION

Nestled in the heart of Cape Cod, this beautifully maintained three bedroom two bath Osterville home offers the ideal blend of relaxation and convenience. Located minutes from all the areas top attractions, this home is perfect for those looking to enjoy coastal living at its finest. Inside you will discover a bright and open main floor featuring a spacious living area and a well appointed eat in kitchen. The main floor also includes a large primary and secondary bedroom along with a full bathroom with a shower and tub. The fully finished lower level provides a private retreat featuring a third bedroom, a second full bathroom, a dedicated laundry area, and a spacious living room. Outside your private backyard oasis awaits. Enjoy mature landscaping with ample space for a pool or addition. Complete with a patio and outdoor shower enjoy this serene setting all summer long. This prime location puts you just minutes from Osterville's village center (with side walk access the entire way to town) , three beaches, and is convenient for commuters. Schedule a showing today!

Type:
Single Family
Sq.Ft.:
2,863
Status:
Active
Beds:
4
Lot size:
0.22 Acres
Year built:
2016
Baths:
5.00
MLS#:
22500428

ADDITIONAL INFORMATION

Situated in a highly sought-after Osterville neighborhood, 85 Hollingsworth Road is an immaculate and spacious home built to suit every need. Ideally located just off Wianno Avenue, the property is equidistant to the quaint downtown center and the serene shores of Dowses Beach. Built in 2016, this pristine residence is move-in ready, providing an idyllic retreat to enjoy Cape Cod's vibrant lifestyle.The open-concept main floor is a showstopper, featuring gleaming hardwood floors, soaring ceilings, and abundant natural light. The gourmet kitchen is outfitted with granite countertops, a professional six-burner Wolf range, a spacious farmhouse sink, and a wine fridge. The living area is centered around a cozy gas fireplace, flanked by two sets of sliding glass doors that lead seamlessly to the backyard and patio--perfect for indoor-outdoor living and entertaining during warmer months. A favorite spot for many is the screened porch, where you can savor fresh air in comfort.The main-floor primary suite is a luxurious private retreat. It features a gas fireplace, dual walk-in closets, and an expansive en-suite bathroom with premium finishes. Upstairs, the second floor is thoughtfully designed with guests and family in mind. A spacious family room anchors the level, leading to three generously sized bedrooms, each with its own en-suite bathroom. This unique layout provides unparalleled comfort and privacy. The fully finished basement continues the home's elegant design, offering endless possibilities as an office, gym, or recreational space. The home also includes a charming front porch, a perfect spot to relax and unwind, as well as a one-car garage for added convenience. Meticulously maintained and brimming with modern amenities, this exceptional home is ready to welcome its next owner into the Cape Cod lifestyle.

Type:
Single Family
Sq.Ft.:
4,715
Status:
Active
Beds:
5
Lot size:
2.03 Acres
Year built:
1978
Baths:
5.00
MLS#:
22500407

ADDITIONAL INFORMATION

Experience the epitome of bayside living at 98 Bunker Hill Road, nestled in Osterville's distinguished Seapuit neighborhood. Sitting peacefully on over 2 acres, this 4,715 sq. ft. estate offers five bedrooms, including three with ensuite baths, and a host of inviting spaces perfect for relaxation or entertaining. Exterior assets include an attached three car garage, an abundant backyard with a swimming pool and hot tub, and deeded rights to Dam Pond!The grand entryway leads to a soaring living room filled with natural light, featuring a striking floor-to-ceiling brick fireplace. The bright, modern kitchen is equipped with stainless steel appliances, a central island, and casual dining space, seamlessly connecting to the formal dining room and a dedicated laundry room.The spacious family room impresses with hardwood floors, high ceilings, custom built-ins, and a wood-burning stove framed by cozy bench seating. A wet bar elevates the space for hosting, while a versatile bonus room above serves as a playroom, gym, or billiards room.The home's opposite wing includes a cheerful office with a wood stove, a guest suite with a full bath, and the luxurious primary suite. This retreat features dual walk-in closets, an expansive bath with a jacuzzi tub and double vanity, and tranquil views of the pool. Upstairs, three additional bedrooms and two full baths offer privacy and comfort. The backyard is a summer oasis, with a sparkling pool, hot tub, outdoor shower, gas grill, and a sprawling patio ideal for entertaining or unwinding. If you're in the mood for a salt water swim or paddle, the property comes with deeded rights to Dam Pond, which connects to North Bay. Sophisticated yet inviting, this property delivers on every aspiration. Discover all it has to offer today!

Type:
Single Family
Sq.Ft.:
1,471
Status:
Active
Beds:
3
Lot size:
0.4 Acres
Year built:
1870
Baths:
3.00
MLS#:
22500406

ADDITIONAL INFORMATION

Rare opportunity on one of Osterville's finest streets. East Bay Road offers a scenic route between the charming village center and beloved Dowses Beach. Remarkable estates and saltwater marshes line the street leading up to the bay itself. Sitting atop a 0.4 acre parcel with a sprawling front lawn, 19 East Bay Road was recently renovated to elevate the historic home's style and functionality. A brand new kitchen with 10.5 foot ceilings welcomes natural light from every angle, with plenty of space to entertain. French doors lead from the dining area to the abundant deck where warm weather conversation and meals are enjoyed. A bay window provides the living room a direct view to the natural beauty and conservation land across the street. The first floor also features a powder room and garage access. The second floor boasts a brand new primary suite with a private deck, walk-in closet, and a well-appointed full bath. Radiant heat below the checkerboard marble floors add a touch of luxury. On the opposite side of the home are two more bedrooms, each with high ceilings and views of East Bay Road. In the second floor hallway is a second full bathroom, as well as a laundry closet. The home's attached one car garage is excellent for storage as-is, or could be converted to additional living space should one desire. The home has a four bedroom septic system, providing potential for future expansion. The owners lovingly refer to this home as "The Needle in the Haystack" and that is what it truly is. An irreplaceable piece of Osterville history that has been carefully renovated and improved to match the beauty of its surroundings.

Type:
Single Family
Sq.Ft.:
8,345
Status:
Active
Beds:
5
Lot size:
3.4 Acres
Year built:
2001
Baths:
5.00
MLS#:
22500391

ADDITIONAL INFORMATION

Osterville Oasis. Sitting on 3.4 acres and abutting 2.88 acres of additional protected land, this exceptional estate offers a family retreat like no other. The home--recently spotlighted by The Wall Street Journal--boasts over 8,000 square feet of thoughtfully designed living space with fully updated systems in pristine condition. The outdoor amenities are unparalleled, featuring a sparkling pool with a charming pool house that offers two bedrooms and a kitchenette, a top tier pickleball court, and a bocce court. Perfect for both intimate gatherings and grand-scale entertaining, the home's interior features two elegant living rooms, an inviting eat-in kitchen, and seamless access to the patio--complete with a hot tub for year-round relaxation. The main floor also hosts the luxurious primary suite, offering a serene retreat. Upstairs, four additional bedrooms, a fully equipped gym, and a recreation room provide endless options for family fun and fitness. With the added convenience of a short distance to Osterville village for shopping and dining.

Type:
Single Family
Sq.Ft.:
3,802
Status:
Active
Beds:
5
Lot size:
2.61 Acres
Year built:
1985
Baths:
5.00
MLS#:
22500167

ADDITIONAL INFORMATION

Nestled in Osterville's coveted Seapuit enclave, this EB Norris-built estate spans over two acres of serene privacy and limitless potential. From the rolling lawns and infinity pool to its deep-water access on Nantucket Sound, the property offers a rare coastal retreat. Soaring windows flood the interior with natural light, revealing mesmerizing, western-facing sunsets and layered views from every room. The flexible floor plan seamlessly integrates grand entertaining spaces with intimate corners, anchored by a luxurious first-floor primary suite for ultimate comfort. Whether you envision a multi-generational residence or simply desire room to expand, this oasis invites you to craft a lasting Cape Cod legacy.Located mere moments from Osterville's renowned Main Street, world-class golf, exclusive clubs, and pristine beaches, this estate transcends the ordinary, delivering an extraordinary lifestyle for discerning buyers seeking the very best of Cape Cod living.

Type:
Single Family
Sq.Ft.:
1,153
Status:
Active
Beds:
3
Lot size:
0.09 Acres
Year built:
1927
Baths:
2.00
MLS#:
22500136

ADDITIONAL INFORMATION

Osterville Village! Experience the best of coastal living in this beautifully updated ranch, nestled in the heart of Osterville Village. Step inside to discover a light-filled, open floor plan where a fully renovated kitchen with quartz countertops and stainless steel appliances awaits your culinary creativity. With two new bathrooms, updated electrical, plumbing, and new HVAC system, this home is truly move-in ready. Outside, the freshly landscaped yard, complete with a new rear patio, fire pit, and charming plantings, creates a perfect setting for outdoor entertaining. The large shed offers endless possibilities, from storage to a potential workshop or studio. Enjoy the convenience of walking to Osterville's charming shops, dining at local restaurants, and immersing yourself in the village's vibrant community life. A quick bike ride takes you to Dowses Beach or the boating haven of Crosby's Boat Yard. Don't miss the chance to make this Osterville gem your own and enjoy the quintessential Cape Cod lifestyle.

Type:
Single Family
Sq.Ft.:
4,470
Status:
Active
Beds:
6
Lot size:
2.32 Acres
Year built:
1929
Baths:
6.00
MLS#:
22404666

ADDITIONAL INFORMATION

Experience the epitome of coastal luxury on a sun-drenched day, where the shimmering water creates an enchanting ambiance. Nestled on over 2.3 acres along the prestigious Sea View Avenue, this extraordinary Osterville estate, built in 1929, is steeped in history and charm. Once cherished by the Crane Family, renowned for supplying the special paper for the U.S. dollar, this home has been lovingly enjoyed since its purchase in 2000. Step inside to discover breathtaking views of Nantucket Sound and 170 feet of pristine, sandy beach. The first floor features a spacious living area and a cozy den/dining room, both with wood-burning fireplaces. The kitchen, complete with a butler's pantry and bar area, leads to a mudroom providing additional storage. There is a first-floor bedroom option, half bathroom, and front to back sunroom with access to the serene Gunite pool equipped with a hot tub and pool house with full bathroom. The second floor offers five bedrooms, including two en-suites, and an additional two full bathrooms, providing plenty of space for family and guests. Additional highlights include wide pine floors throughout, detached carriage house with a finished room, walkout basement, and 7-bedroom septic system. Located just minutes from Osterville village, this iconic home represents a once-in-a-lifetime opportunity to own a piece of history and coastal elegance. Don't miss the chance to make this timeless estate your own.

Type:
Single Family
Sq.Ft.:
5,960
Status:
Active
Beds:
7
Lot size:
1.12 Acres
Year built:
1986
Baths:
7.00
MLS#:
22404647

ADDITIONAL INFORMATION

Step into refined luxury with this exceptional water view residence featuring beautiful views of North Bay and nestled within the gated community of Oyster Harbors. Situated on an elevated 1.12-acre lot with mature, meticulously maintained landscaping, this exquisite home exudes curb appeal and features high-end renovations throughout. The heart of the home is the sophisticated kitchen, designed for both beauty and function, featuring a center island with a breakfast bar, custom built-in pantry shelving, and a stylish wet bar. Adjacent is the sunlit dining area that flows seamlessly into a magnificent family room, where cathedral ceilings soar above, and a gas fireplace warms the space. Expansive windows frame the serene water views of the Bay, bringing the outdoors in.The formal front-to-back living room, with its elegant gas fireplace and French doors opening to both the front and rear patios, offers the perfect retreat for relaxation or entertaining. A separate formal dining room overlooks the lushly landscaped backyard and inviting inground pool, creating an idyllic backdrop for intimate gatherings. The first-floor primary suite is a haven of comfort and convenience, complete with water views, a spacious walk-in closet and custom bathroom. Upstairs, three additional well-appointed bedrooms and a home office provide flexibility and luxurious living. Outside, indulge in the ever-changing water views of the Bay from the front patio or relax in the seclusion of the private backyard oasis, where a sparkling inground pool invites you to unwind. Completing this fabulous estate is a privately set guest house, offering a charming living room and kitchenette, bathed in natural light from the secluded patio. The guest house also features a first-floor bedroom with built-in bunk beds and a generously sized second-floor bedroom suite. Additional property features include a detached one-car garage, storage shed, a generator, and multiple seating areas designed to capture the beauty of the surrounding landscape. This classic estate combines ultimate privacy with the convenience of being just moments away from the village of Osterville, known for its pristine beaches, boutique shopping, and fine dining. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

Type:
Single Family
Sq.Ft.:
8,203
Status:
Active
Beds:
6
Lot size:
2.4 Acres
Year built:
2017
Baths:
9.00
MLS#:
22404283

ADDITIONAL INFORMATION

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 appliances and a state-of-the-art home theatre. The six ensuite bedrooms include a first-floor suite with French doors leading to the back yard and a lavish primary suite with a luxurious bathroom, two walk-in closets and a private deck overlooking the water. Enhanced with modern conveniences such as a Sonos whole-house sound system and a 9-zone Hydro air system, every detail has been carefully planned and implemented. Additional highlights include a private guest suite above the attached 3-car garage and a sprawling entertainment room with a balcony on the third level highlighted by western exposure to experience breathtaking sunsets. Located just minutes from the upscale boutiques and renowned dining of Osterville village, this extraordinary property offers a lifestyle of unparalleled elegance and tranquility by the sea. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

Type:
Condo
Sq.Ft.:
1,150
Status:
Active
Beds:
2
Year built:
1982
Baths:
2.00
MLS#:
22404100

ADDITIONAL INFORMATION

Enjoy in-town living with all that Osterville has to offer at your front door. Whether looking for a pied-a-terre or a full-time residence, this first-floor ranch style 2 bed/2bath end unit WITH GARAGE in the desirable Osterville Village condominium complex could be the answer! This light and bright unit offers a slate entry and hardwood floors throughout the living and dining areas. The living room has built-in storage units surrounding the oversized window, a wood burning fireplace for cool evenings and sliders to a private patio for your personal enjoyment. Entertaining is a breeze! The kitchen with generous cabinet and counter space flows smoothly to the dining area. New SS appliances were recently installed. The light filled primary bedroom includes a large en suite bath with ample closet space and double sinks. A generous second bedroom, full guest bath and laundry area complete the living space. Recent renovations include new air conditioning system, appliances and window replacement. Close to dining, shopping, the beach and so much more...don't miss this gem!

Type:
Single Family
Sq.Ft.:
3,510
Status:
Active
Beds:
4
Lot size:
1.99 Acres
Year built:
1971
Baths:
4.00
MLS#:
22403644

ADDITIONAL INFORMATION

Experience tranquility and charm on nearly two acres of prime Bumps River waterfront. Start your day with a peaceful sunrise from the back deck, coffee in hand, as you watch wildlife gracefully soar around you.Enjoy the ease of one-floor living with a thoughtfully designed floor plan that maximizes views from the kitchen, family room, living room, and primary bedroom, constantly reminding you why you chose this home. Ample space for entertaining both inside and out enhances the enjoyment of this serene setting.The lower walk-out level provides extra space for guests, storage, and even features an additional side garage perfect for your kayaks, paddle boards, or small boat. When you're ready for some beach time or a boating adventure, Dowses, Long, and Craigville Beaches are nearby, with your private ''new'' dock offering direct access to Nantucket Sound. Plus, Osterville Village is just a short distance away, offering excellent shopping and dining options. The dock has been replaced since the drone / photo shoot

Type:
Single Family
Sq.Ft.:
5,421
Status:
Active
Beds:
5
Lot size:
0.53 Acres
Year built:
2002
Baths:
6.00
MLS#:
22400761

ADDITIONAL INFORMATION

Located a short stroll from Osterville Village, this shingle-style home showcases stunning architectural details and scenic views over Wianno Golf Course and Parker Pond. Exquisite craftsmanship is on full display throughout, from a spacious covered porch that greets visitors to a gourmet kitchen with honed granite countertops and cherry cabinetry. The first-floor primary suite includes a luxurious marble bathroom and secluded home office. On the second floor, an open family room is seamlessly connected to the outdoors with front and back decks, while offering the utmost convenience with a thoughtfully designed kitchenette. Two bedrooms and two bathrooms with rain showers complete the second floor. A lush and private backyard with a bluestone patio offers the perfect setting to embrace outdoor living. Additional highlights include a 275-bottle wine cellar with a EuroCave cooler and a serving island, an integrated Sonos Sound System throughout interior and exterior living spaces, and a four-car garage with a self-contained apartment above. Mere minutes from everything Osterville has to offer, this extraordinary residence delivers the quintessential Cape Cod lifestyle.

Type:
Condo
Sq.Ft.:
360
Status:
Active
Beds:
n/a
Year built:
1987
Baths:
MLS#:
22400127

ADDITIONAL INFORMATION

Looking for an off property garage or storage unit in Osterville? This Osterville Village condo garage may be just what you're looking for! This unit has 360 sq ft. according to town records. There is also another unit next to this (#18) that is for sale as well. A rare opportunity in the village for much needed space.

Type:
Single Family
Sq.Ft.:
7,157
Status:
Active
Beds:
5
Lot size:
1.65 Acres
Year built:
1999
Baths:
5.00
MLS#:
22304800
Subdivision:
Oyster Harbors

ADDITIONAL INFORMATION

Located within the private, gated golf community of Oyster Harbors, in the village of Osterville, is this magnificent five-bedroom waterfront residence with an in-ground pool and deep-water dock. This beautiful residence has the look and feel of a European estate with an open floor plan design and beautiful water vistas. Refined architectural details set the tone in this grand home with 7,157 sq. ft. of living space. Interior spaces begin with a spacious foyer opening into an extraordinary great room with vaulted ceiling, walls of windows, dramatic columns and custom fireplace. A light filled dining room overlooks the water with custom arched windows leading into a stunning chef's kitchen with coffered ceiling, granite countertops with large center island and access to a waterside patio. A lavish first floor primary suite and four additional bedrooms, including a full suite over the garage, offer ample room for family and friends. This unique and inspirational home is set on a private 1.65 acre parcel with beautiful outdoor seating areas overlooking the water, the pool, gardens and deep-water dock creating an ideal backdrop for entertaining family and friends. There is an attached three car garage, and this property provides plenty of extra parking. This one-of-a-kind property will appeal to the most discerning buyer.

Type:
Single Family
Sq.Ft.:
4,896
Status:
Active
Beds:
7
Lot size:
5.98 Acres
Year built:
1988
Baths:
6.00
MLS#:
22203874

ADDITIONAL INFORMATION

Welcome to ''Point House'' a spectacular 5.98-acre waterfront estate on a peninsula overlooking the glistening waters of West Bay. In a setting of unsurpassed beauty, the 4,896 square foot residence offers truly exceptional water vistas, beautiful gardens, an expansive private sandy beach, and a substantial deep-water dock from which you can sail into the waters of Nantucket Sound. The 6-bedroom home features generous yet comfortable living spaces, beautiful architectural detailing, custom wood flooring and 5 fireplaces. The entry foyer welcomes you to the beautiful views and impressive deck that runs the length of the home and beckons you to step outside to take in the panoramic views. Highlights include a light filled, two story great room with a beautiful floor-to-ceiling brick fireplace, a well-equipped kitchen opening into the dining area and a family room accented by a fireplace all opening to the outside living spaces making this flow ideal for quiet family enjoyment or larger scale entertaining. Two bedrooms and a sitting room with fireplace can also be found on the 1st level. The primary bedroom features beautiful water views, a spacious bath, walk in closet and a large sitting room with fireplace, and three additional bedrooms and a sitting room finish the 2nd level. A third-floor walkup to a tower provides the perfect vantage point to watch the incredible sunsets you'll experience from this property. Also offered is a detached two car garage which includes living space above for extended family and guests. This seaside estate affords the utmost privacy yet offers proximity to the village of Osterville with its boutique shops and fine dining. Experience an exceptional lifestyle from this one-of-a kind waterfront estate!

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Andrea Conner, License 1000188, Xome Inc., License 9622, AndreaD.Conner@xome.com, 844-400-XOME (9663), 750 Highway 121 Bypass, Ste 100, Lewisville, TX 75067

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The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod and Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than Xome are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor this broker shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. Copyright 2025 Cape Cod and Islands MLS, Inc. All rights reserved.



Osterville Real Estate

The median home value in Osterville, MA is $610,000. The national median home value is $338,100. The average price of homes sold in Osterville, MA is $610,000. Osterville real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Osterville real estate agent to arrange a tour today!

Osterville Weather

Osterville Real Estate Market Conditions

  • Median sales price

    $610,000
    -3276800% change since last quarter
  • # Active listings

    21
    30-day change

Osterville Schools and Demographics

Education near Osterville, MA

Metric City County
High School Graduates N/A N/A
College Degree - 2 year N/A N/A
College Degree - 4 year N/A N/A
Graduate Degree N/A N/A
Expenditures per Student N/A N/A
Students per Teacher N/A N/A

Elementary Schools near Osterville, MA

School Grades Students P/T Ratio ZIP
Barnstable Community Horace Mann Charter Public School KG - 03 291 12.3 02601
Centerville Elementary PK - 03 427 14.5 02632
Hyannis West Elementary School KG - 03 355 10.9 02601
Kenneth Coombs School PK - 02 443 13.6 02649
Quashnet School 03 - 06 525 12.6 02649
West Villages Elementary School KG - 03 450 15.8 02648

Middle Schools near Osterville, MA

School Grades Students P/T Ratio ZIP
Barnstable Intermediate School 06 - 07 751 12.4 02601
Barnstable United Elementary School 04 - 05 772 13.2 02648
Mashpee Middle School 07 - 08 268 13.4 02649

High Schools near Osterville, MA

School Grades Students P/T Ratio ZIP
Barnstable High School 08 - 12 1,911 13.4 02601
Mashpee High School 09 - 12 431 10.4 02649
Sturgis Charter Public School 09 - 12 806 9.4 02601