Osterville MA Real Estate & Homes for Sale

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Beds:
4
Baths:
3.00
Sq.Ft.:
2,050
Status:
NEW LISTING
MLS#:
22603965
Type:
Single Family
Lot size:
0.82 Acres
Year built:
1961
A broker reciprocity listing Courtesy: The Foley Company 508-685-8928
View additional info

ADDITIONAL INFORMATION

Discover the charm of Wianno in this beautifully renovated four-bedroom, three-bath home, walking distance to Osterville Village, beaches, and the best of Cape Cod living. With deeded access to Eel River and lovely views overlooking the Wianno golf course, this inviting property offers a rare combination of location, comfort, and lifestyle. Thoughtfully designed for easy one-level living, the turnkey home features a warm and welcoming living room with fireplace, vaulted ceilings, and a relaxed country feel. The spacious deck overlooking the golf course provides an idyllic setting for morning coffee, summer entertaining, or unwinding at the end of the day. This home's exceptional location puts Osterville Village, beaches, boating, dining, and shopping close at hand. Whether you're seeking a year-round residence or a special Cape Cod retreat, this Wianno property offers an outstanding opportunity in a highly desirable setting. New Title V compliant septic system installed.

Beds:
7
Baths:
11.00
Sq.Ft.:
10,104
Status:
NEW LISTING
MLS#:
22603952
Type:
Single Family
Subdivision:
Oyster Harbors
Lot size:
1.97 Acres
Year built:
2007
A broker reciprocity listing Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties 508-420-1414
View additional info

ADDITIONAL INFORMATION

Exquisite waterfront estate in the gated enclave of Oyster Harbors, one of Cape Cod's most sought-after communities. Located minutes from everything Osterville has to offer, yet a world apart, the property represents a rare and extraordinary opportunity to own a generational compound in an inimitable setting. Ideally positioned to capture dramatic sunsets over Cotuit Bay and Nantucket Sound beyond, the estate features a stunning main residence, a two-bedroom guest cottage, a swimming pool, private dock, and more. A wooded drive gives way to manicured grounds of nearly two acres, transporting one to a private seaside resort as the ocean comes into view. Inside, an open layout caters to 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 invites al fresco dining and entertaining. Elevated quality and craftsmanship are found throughout, from rich hardwood floors to custom built-ins and crown moldings. The expansive primary suite encompasses an entire wing of the home with a private balcony overlooking the water, a sumptuous bathroom with a built-in soaking tub, and two walk-in closets. Four well-appointed en suite bedrooms complete the second level, offering refined accommodations for family and friends. Designed to embrace outdoor living, the resort-inspired pool and terrace are the perfect gathering place for summer days, complete with an outdoor kitchen and cabana. A rolling lawn leads to the water, where the private dock offers endless possibilities for days spent on the ocean. Additional highlights include a sports court and a car barn that's sure to please the discerning automotive enthusiast. A rare combination of luxury, privacy, and natural beauty, this one-of-a-kind estate is ready to be enjoyed.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,721
Status:
NEW LISTING
MLS#:
22603916
Type:
Single Family
Lot size:
1.92 Acres
Year built:
1963
A broker reciprocity listing Courtesy: The Foley Company 508-685-8928
View additional info

ADDITIONAL INFORMATION

Waterfront home in the heart of Osterville Village, where charming shops, restaurants, and amenities are just a short stroll away. Enjoy spectacular, unobstructed views, sunsets and frontage on the picturesque North Bay- all this and room for a pool. This meticulously maintained and beautifully appointed home is move-in ready, offering the perfect opportunity to enjoy immediately or create your dream waterfront retreat. With a 5-bedroom septic system already installed, the property offers outstanding expansion potential, making it ideal for future additions or a custom renovation. Whether you're seeking a turnkey home or envisioning a larger estate, this exceptional property combines an unbeatable village location with endless possibilities. No flood insurance required on current property.

Beds:
5
Baths:
8.00
Sq.Ft.:
5,970
Status:
Active
MLS#:
22603652
Type:
Single Family
Lot size:
0.93 Acres
Year built:
1940
A broker reciprocity listing Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties 508-420-1414
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ADDITIONAL INFORMATION

Representing the pinnacle of coastal elegance, this extraordinary estate on Little Island offers a rare opportunity for a generational compound in mint condition and an unsurpassed location. Finished to the highest standards, the property features a spectacular five-bedroom main residence, a swimming pool, a pool house with kitchenette and full bath, and a detached three-car garage with a home gym above. In the main residence, timeless and sophisticated design is on display throughout, with custom millwork, designer wallpaper, soaring vaulted ceilings, and a smart home system that governs doors, locks, and hardware with effortless ease. Superlative craftsmanship and finishes define every room, from the chef's kitchen with professional grade appliances to the exquisitely appointed first-floor primary suite featuring custom-designed closets and a luxurious bathroom with a jetted Grohe shower system. Four additional bedrooms, including a second-floor primary suite, ensure refined accommodations for family and guests, while a finished lower level provides flexible bonus space. Set amidst park-like grounds with manicured landscaping, the backyard features multiple gathering spaces, including an expansive poolside terrace with a summer kitchen and fire pit. The stunning pool house caters to resort-style living and offers endless possibilities. Meticulously appointed with no detail overlooked, additional highlights include a whole-home generator, state-of-the-art security, and Lutron smart lighting. Minutes from everything Osterville has to offer, this exceptional family compound is ready to be enjoyed.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,100
Status:
Active
MLS#:
22603520
Type:
Single Family
Lot size:
0.4 Acres
Year built:
1971
A broker reciprocity listing Courtesy: The Greene Realty Group 888-278-5840
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ADDITIONAL INFORMATION

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 of build-able land to build your luxury dream home. Or keep it as the year-round home it currently is with rental income as an option in the separate lower-level space. Sold furnished or not.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,297
Status:
Active
MLS#:
22603408
Type:
Single Family
Lot size:
0.47 Acres
Year built:
1982
A broker reciprocity listing Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties 508-420-1414
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ADDITIONAL INFORMATION

Welcome to 17 Galleon Way, a charming Osterville ranch offering the perfect blend of comfort, versatility, and Cape Cod living. The main home features a beautifully renovated kitchen, two bedrooms and one and a half baths, all thoughtfully designed for easy one-level living. Main home is 864 sq ft. An attached garage adds everyday convenience and additional storage.A standout feature of this property is the attached one-bedroom, one-bath apartment (432 sq ft) offering exceptional flexibility for extended family, guests, a home office, or potential rental income (subject to applicable regulations and approvals). The apartment was permitted as in in-law apartment. Buyer will need to re-apply for the proper permits dictated by a change in ownership. Set on a 1/2 acre lot, you'll enjoy being just minutes from Osterville Village's boutiques, restaurants, marinas, golf courses, and some of Cape Cod's most beautiful beaches. Whether you're searching for a year-round residence, a seasonal getaway, or an investment opportunity.Buyer to do due diligence.

Beds:
3
Baths:
4.00
Sq.Ft.:
3,355
Status:
Active
MLS#:
22603317
Type:
Single Family
Subdivision:
Tanglewood
Lot size:
0.34 Acres
Year built:
1978
A broker reciprocity listing Courtesy: Coastal Real Estate Advisors LLC 617-416-4601
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ADDITIONAL INFORMATION

Offered for the first time! 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 landscaping shines in every season! Inside, the welcoming main entry leads to a spacious sitting room with bay window, opening into an elegant dining room. The bright and airy 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 a window seat. A separate wing of the main floor has 2 bedrooms, an office and 2 full bathrooms. The main level is rounded out by a third full bathroom and laundry closet. Upstairs, there is a massive 3rd bedroom with full bathroom and its own office. All this in a private neighborhood minutes from Osterville Village. New central AC, Generator, irrigation, a shed, composite deck and two car garage... come see why this home was worth holding on to!

Beds:
5
Baths:
6.00
Sq.Ft.:
7,157
Status:
Active
MLS#:
22603271
Type:
Single Family
Subdivision:
Oyster Harbors
Lot size:
1.65 Acres
Year built:
1999
A broker reciprocity listing Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties 508-420-1414
View additional info

ADDITIONAL INFORMATION

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 captures tranquil water views and flows seamlessly into a beautifully appointed chef's kitchen featuring a coffered ceiling, granite countertops, an oversized center island, and direct access to a spacious waterside terrace. The first-floor primary suite offers a luxurious private retreat, while four additional bedrooms--including a gracious guest suite above the attached three-car garage--provide exceptional accommodations for family and guests. Outdoor living is equally compelling. Expansive terraces and inviting gathering spaces overlook the pool, manicured gardens, and deep-water dock, creating an idyllic setting for waterfront entertaining or peaceful afternoons by the shore. Set within one of Cape Cod's most coveted private enclaves, where golf, boating, and an unmatched sense of privacy define the lifestyle, this exceptional estate represents a rare opportunity to own a legacy property in Oyster Harbors.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,808
Status:
Active
MLS#:
22603216
Type:
Single Family
Lot size:
0.38 Acres
Year built:
1985
A broker reciprocity listing Courtesy: Compass Massachusetts, LLC 508-206-8726
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ADDITIONAL INFORMATION

Nestled in a neighborhood south of Route 28, this charming Osterville ranch offers the perfect blend of classic Cape Cod character & modern comfort. Before you even step inside, a private front patio welcomes you, the ideal spot for a pair of Adirondack chairs. The interior has been thoughtfully reimagined for contemporary living w/ a bright open concept layout. Upon entry, you're greeted by a sun-drenched dining area that sets an inviting tone w/ its cathedral ceilings, a skylight & sliders that lead out to a freshly painted deck. The kitchen offers a central island providing a natural gathering spot before transitioning into the living room. Anchored by a fireplace this central living space feels remarkably open & airy. The home features 2 bedrooms, including a primary en-suite. Brand-new carpeting flows throughout the entire home, paired w/ an abundance of storage space to keep everything perfectly organized. The living space extends to a walkout basement, providing a versatile layout that easily adapts to your specific needs. This lower level opens to a private, level yard. This Osterville gem is ready for you and its next chapter to begin.

Beds:
5
Baths:
7.00
Sq.Ft.:
4,100
Status:
Active
MLS#:
22603117
Type:
Single Family
Lot size:
0.52 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Coldwell Banker Realty 508-862-8021
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ADDITIONAL INFORMATION

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!

Beds:
7
Baths:
8.00
Sq.Ft.:
9,011
Status:
Active
MLS#:
22603124
Type:
Single Family
Lot size:
1.38 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties 508-945-5553
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ADDITIONAL INFORMATION

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. Set aside any reservations of the year built...the entire foundation and structure were comprehensively reinforced and renovated by E.J. Jaxtimer. Any changes or modifications a buyer might want would be aesthetic alone. 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 with vaulted ceilings and additional charm. The square footage of 9,011, seven bedrooms and seven-and-a-half bathrooms speak for themselves. This treasure is waiting for you.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,359
Status:
Active
MLS#:
22602969
Type:
Single Family
Lot size:
0.76 Acres
Year built:
1985
A broker reciprocity listing Courtesy: William Raveis Real Estate & Home Services 508-428-3320
View additional info

ADDITIONAL INFORMATION

Osterville Oasis...Tucked away at the end of a quiet, tree-lined lane, this beautifully renovated Cape-style home offers the perfect blend of classic charm with modern updates in highly desirable Oyster Hills West. The first floor features a spacious Primary Suite with a private bath, overlooking a lushly landscaped, private backyard. The inviting Living Room showcases custom built-ins and a striking Gas Fireplace, flowing seamlessly into a lovely Porch-an ideal spot to enjoy morning coffee while taking in the peaceful surroundings. The oversized dining area highlights upgraded Andersen windows installed throughout the home in 2019, bringing abundant natural light. A renovated Granite Kitchen, 1st-Floor Laundry, and Powder Room provide complete 1st-floor living potential. Upstairs, you'll find three generously sized Bedrooms, one including an En-Suite half Bath, plus an additional full Bathroom A partially finished Lower Level with dual Cedar Closets offers valuable bonus space and future expansion potential. Upgrades include Gas Furnace(2020), Water Heater(2020), A/C System(2023), Hardwood floors(2019) Roof(2016), handsome Granite Steps (2025), Generator (2022)...Ready for you

Beds:
3
Baths:
2.00
Sq.Ft.:
1,426
Status:
Active
MLS#:
22602806
Type:
Single Family
Lot size:
0.41 Acres
Year built:
1979
A broker reciprocity listing Courtesy: C. Case Realty, LLC 508-868-2105
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ADDITIONAL INFORMATION

Welcome to this 3 bedroom, 2 bath Cape-style home in the coastal village of Osterville, situated on a corner lot in a neighborhood setting. This property features new kitchen cabinets, new stainless appliances, backsplash and granite countertops. A fireplace living room to enjoy on cool nights and a dining room with sliders to a spacious deck with a gas hookup for grilling, ideal for entertaining your guests. The first-floor primary bedroom and bath provide convenient one-level living, while the walkout lower level offers excellent potential for expansion, a home office or recreation space and includes French doors leading to a brick patio. An attached one-car garage adds storage and convenience. Enjoy the beach, boating, shopping, and dining in this vibrant coastal village. Whether you're seeking a year-round residence, vacation getaway, or Cape Cod retreat, this well-appointed home offers the best of Osterville living.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,636
Status:
Active
MLS#:
22602737
Type:
Single Family
Lot size:
1.68 Acres
Year built:
1978
A broker reciprocity listing Courtesy: Sotheby's International Realty 508-428-9115
View additional info

ADDITIONAL INFORMATION

In Osterville, certain streets make the most of Village living. Starboard Lane, winding along the western shore of the Bumps River, is among the village's most coveted addresses. Known for gracious homes with exceptional privacy on large parcels, the convenience to the heart of Osterville is a huge plus. 420 Starboard Lane captures the Village vibe wonderfully. Set on 1.68 acres, this four-bedroom 2,636 square foot residence offers an exceptional kitchen, generous gathering spaces, may recent updates, and the flexibility that make for easy coastal living. A detached two-car garage with unfinished space above presents intriguing possibilities for expansion. Private. Prestigious. Perfectly located. A rare chance to claim your place in one of Osterville's most sought-after enclaves.Opportunity like this rarely lingers.Please verify all information contained herein.

Beds:
6
Baths:
8.00
Sq.Ft.:
8,387
Status:
Active
MLS#:
22602716
Type:
Single Family
Lot size:
2.6 Acres
Year built:
2026
A broker reciprocity listing Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties 508-420-1414
View additional info

ADDITIONAL INFORMATION

Newly constructed and ready to enjoy, this exceptional waterfront estate on the Bumps River represents the finest of Cape Cod living. Combining an unrivaled setting with state-of-the-art luxury, the property features a resort-inspired swimming pool and cabana, a renovated boathouse with a float for non-motorized crafts, and a deeded beach lot on Long Beach. Upon approaching the estate, an incomparable level of craftsmanship and finish is immediately on display, from the Maibec white cedar shingle siding to Pella Architect Series windows and doors throughout. Inside, the open floor plan seamlessly flows from a fireplaced living room with coffered ceilings to a gourmet kitchen anchored by a Sub-Zero French door refrigerator, a Wolf range, and Danby natural stone counters. A built-in banquette breakfast nook, full pantry with second refrigerator, and a wet bar complete the space. Glass doors line the waterside of the home, opening to an expansive Phoenician Buff stone terrace surrounding a custom Pebble Tec pool and spa. The first-floor primary wing offers direct terrace access, two custom walk-in closets, and a luxurious bath with natural stone countertops and a freestanding soaking tub. Four well-appointed en suite bedrooms, a family room, and an ipe deck with stainless cable railing occupy the second level, with flexible bonus space above. A private bedroom suite over the garage accommodates guests or staff. Located minutes from everything Osterville has to offer, this extraordinary property represents a rare opportunity to own a newly built waterfront estate in one of Cape Cod's most sought-after communities.

Beds:
4
Baths:
5.00
Sq.Ft.:
5,049
Status:
Active
MLS#:
22602715
Type:
Single Family
Lot size:
2.05 Acres
Year built:
1996
A broker reciprocity listing Courtesy: Kinlin Grover Compass 508-362-2120
View additional info

ADDITIONAL INFORMATION

Nestled within the prestigious enclave of Seapuit, this architectural masterpiece represents a rare synergy of design and craftsmanship spanning over 5,000SF of meticulously curated space. A collaboration between renowned architect Doreve Nicholaeff & the master builders at Sylvia & Sylvia, the residence is an exercise in sophisticated coastal living. The home is set on a two-acre private oasis, featuring manicured grounds in a serene courtyard setting designed by the acclaimed David Hawk. The main level is anchored by a sumptuous primary suite boasting a state-of-the-art bathroom, a dedicated dressing room, and dual walk-in closets. Upstairs, two additional private suites offer refined accommodations for guests or family & the newly finished lower level extends the living space even further. Modern luxury is seamlessly integrated through a recently installed, whole-home Savant automation system, giving you effortless control over climate, lighting, and entertainment at the touch of a button. The heart of Osterville Village & the sands of Dowses Beach are just a few minutes away. This is more than a home; it's a legacy estate offering a lifestyle of unmatched privacy & convenience.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,924
Status:
Active
MLS#:
22602593
Type:
Single Family
Lot size:
0.62 Acres
Year built:
1915
A broker reciprocity listing Courtesy: William Raveis Real Estate & Home Services 508-428-3320
View additional info

ADDITIONAL INFORMATION

Prime location on one of Cape Cod's most coveted roads, East Bay Road in Osterville. This beautiful home is rich with character, having been repurposed from a large carriage house. It boasts history and classic Cape Cod charm. Enter the home through the large living room and move into the kitchen equipped with a bright sunroom off to the right. An old horse stable has been fashioned into an office space that is located to the left of the kitchen, with an adjacent first-floor full bathroom. Upstairs are 4 bedrooms, two of which include ensuite bathrooms. Downstairs a finished basement provides more living space as well as a laundry room and a full bath. Outside, a detached 2-car garage provides space for your vehicles as well as a shed for storage. A beautiful fenced in side yard is ideal for summer gatherings, games or just relaxing. There is also an outdoor area out back for grilling and dining, as well as an outdoor shower, perfect after a day spent at the beach. Just minutes from Dowses Beach, the East Bay boat landing, and Osterville Main Street, this home embodies vintage Cape Cod charm and is ready for a future with somebody who will appreciate its beauty and character.

Beds:
5
Baths:
8.00
Sq.Ft.:
8,740
Status:
Active
MLS#:
22602488
Type:
Single Family
Subdivision:
Oyster Harbors
Lot size:
1 Acres
Year built:
2006
A broker reciprocity listing Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties 508-420-1414
View additional info

ADDITIONAL INFORMATION

Set on the 14th fairway of the golf course within the coveted gated community of Oyster Harbors, this exceptional residence combines timeless design with modern comforts in a beautifully crafted coastal setting. The home is defined by generous proportions, abundant natural light, and refined architectural detail throughout. Thoughtfully designed living spaces feature soaring ceilings and a striking double-sided stone fireplace that creates a warm focal point between gathering areas. The kitchen is tailored for both everyday living and entertaining, offering professional-grade appliances, expansive stone countertops, and a custom mahogany butler's pantry that provides additional prep and serving space. A secluded primary suite enjoys its own dedicated wing on the first floor, complete with a luxurious bathroom, two walk-in closets, and French doors that open to a private patio overlooking the swimming pool and gardens.Outdoor amenities take full advantage of the private setting, with multiple covered porches and a heated Gunite pool with limestone surround, all positioned to capture views of the golf course. Leaving nothing to be desired, ownership includes deeded beach access and passenger dock rights. An exceptional offering in one of Cape Cod's most sought-after communities, this magnificent lifestyle property is ready to be enjoyed.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,954
Status:
Active
MLS#:
22602404
Type:
Condo
Year built:
1988
A broker reciprocity listing Courtesy: Sotheby's International Realty 508-428-9115
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ADDITIONAL INFORMATION

This spacious two bedroom, two and one half bath condo at Fairways in Osterville village is perfect for summer or year-round living. The condo abuts the Wianno Golf course and offers three floors of living and includes basement storage and a detached one car garage..The second floor includes a light-filled living room lined with windows,a gas fireplace, a screened porch with views of the 5th hole of Wianno Golf course, a large, bright dining room, kitchen,and a half bath with laundry. The third floor offers a spacious prmary bedroom with high ceilings, a private balcony with views and and an ensuite-bath. Stairs lead to a lovely office loft area facing the golf course. A second bedroom has a tray ceiling, full bath and closet. The condo is ideally located close to the village with restaurants, shops, marinas, library, churches and Dowses Beach.This is a wonderful opportunity to add your finishing touches and live and entertain close to the action of the village. First showings June 13, 11-1

Beds:
3
Baths:
6.00
Sq.Ft.:
4,831
Status:
Active
MLS#:
22602282
Type:
Single Family
Lot size:
0.78 Acres
Year built:
1946
A broker reciprocity listing Courtesy: William Raveis Real Estate & Home Services 508-428-3320
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ADDITIONAL INFORMATION

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, (complete with 30 Amp power outlets and fresh water). 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, this rare offering combines serenity, sophistication, and the quintessential Cape Cod lifestyle in one unforgettable waterfront setting.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,088
Status:
Active
MLS#:
22602304
Type:
Condo
Year built:
1967
A broker reciprocity listing Courtesy: Craigville Realty Co 508-775-3174
View additional info

ADDITIONAL INFORMATION

RARE to market! First opportunity in YEARS in Osterville's sought after Wianno Knoll. Nestled in the heart of Osterville village this desirable first floor condo has it all! Gorgeous open floor plan features two spacious bedrooms, a completely updated full bath and charming guest half bath. Renovated open kitchen with pantry closet, stainless appliances. and sliders leading to private back porch surrounded by beautiful, lush landscaping, perfect for enjoying your morning coffee. Additional features include hardwood floors, cozy brick fireplace, custom wood shutters and window treatments, numerous closets throughout with additional huge, private storage area for bikes, beach gear, seasonal decor, and more. Walk to restaurants, boutiques, market, cafes, and ice cream! Walk or bike to the crown jewel of Cape Cod, stunning Dowses Beach only a half mile away. Move in ready and won't last, be in for Summer!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,040
Status:
Active
MLS#:
22601981
Type:
Single Family
Subdivision:
Osterville Heights
Lot size:
0.35 Acres
Year built:
1977
A broker reciprocity listing Courtesy: Sotheby's International Realty 508-428-9115
View additional info

ADDITIONAL INFORMATION

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 Osterville Village, Dowses Beach, golf, boating, shopping, dining, and other premier local amenities. A wonderful opportunity to enjoy the Cape Cod lifestyle in one of Osterville's coveted locations.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,178
Status:
Active
MLS#:
22601973
Type:
Single Family
Lot size:
0.27 Acres
Year built:
1858
A broker reciprocity listing Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties 508-420-1414
View additional info

ADDITIONAL INFORMATION

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 and relaxation.Ideally located just moments from Osterville Village, this property enjoys close proximity to boutiques, dining, and nearby beaches, while also being near some of the area's most renowned marinas, including Nauticus Marina, Crosby Yacht Yard, and Oyster Harbors Marine - offering convenient access to premier boating and waterfront amenities. The adjacent property at 30 Cockachoiset Lane is also available for sale (MLS 22601972). Together, the properties offer a rare opportunity to create a side-by-side coastal compound, with a demonstrated history of significantly strong, high-value rentals and private gatherings.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,084
Status:
Active
MLS#:
22601935
Type:
Single Family
Lot size:
1.22 Acres
Year built:
1998
A broker reciprocity listing Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties 508-420-1414
View additional info

ADDITIONAL INFORMATION

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 by a two-story wall of windows and a Palladian arch that floods the home with light. This formal area flows into the dining room and a functional kitchen featuring granite countertops, a central island with a cooktop, and a sunny breakfast nook. Adjacent to the kitchen, a comfortable family room offers custom built-ins and a brick fireplace.The primary suite provides a quiet sanctuary on the first floor, complete with a walk-in closet and en suite bathroom. Upstairs, a versatile mezzanine gallery overlooks the living area and leads to two well-proportioned guest bedrooms. Outside, the expansive rear deck, complete with a retractable awning and vine-covered pergola, overlooks a private lawn and a peaceful ornamental pond, offering a perfect setting for outdoor relaxation. All of this, just a short drive away from Osterville Village and Dowses Beach.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,048
Status:
Active
MLS#:
22601704
Type:
Single Family
Lot size:
0.91 Acres
Year built:
1971
A broker reciprocity listing Courtesy: Property Cape Cod 508-420-4200
View additional info

ADDITIONAL INFORMATION

New spacious front yard and entrance redesigned !!! Fall in love the moment you step inside this beautifully renovated home that feels brand new in every way. Sunlight fills the space throughout the day, drawing your eye to tranquil pond views and the surrounding natural beauty that create an immediate sense of calm and privacy. Thoughtfully redesigned with modern amenities, this home offers effortless living both indoors and out. Imagine preparing meals in the outdoor kitchen while overlooking the water, or starting your day in the main-level bedroom with peaceful pond views before stepping onto the deck with your morning coffee. Tucked into a serene setting, yet just minutes to the boutiques, restaurants, coffee shops, and ice cream spots of Osterville Village. Enjoy easy access to all of Barnstable's beautiful beaches, with iconic Dowses Beach only minutes away. A private retreat that perfectly blends nature, comfort, and location. Note: Town Field Card does not reflect renovation updates, additional sq footage or 3 bedroom count.

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Andrea D. Conner, License 1?0?0?0?1?8?8, Xome Inc., License 9622, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067


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 2026 Cape Cod and Islands MLS, Inc. All rights reserved.



Osterville Real Estate

Osterville is located in Massachusetts.

Osterville Weather

Osterville Map

Osterville Real Estate Market Conditions

  • Median sales price

    $1,274,250
    -3276800%
    change since last quarter
  • # Active listings

    38
    30-day change

Osterville Schools and Demographics

Education near Osterville, MA

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

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

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

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

Demographics near Osterville, MA

City County
Neighborhood Type
Population N/A N/A
Population Density N/A N/A
Median Age N/A N/A
People per Household N/A N/A
Median Household Income N/A N/A
Average Income per Capita N/A N/A

Real estate near Osterville