Osterville MA Real Estate & Homes for Sale

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Beds:
2
Baths:
2.00
Sq.Ft.:
1,055
Status:
NEW LISTING
MLS#:
22604877
Type:
Single Family
Lot size:
0.5 Acres
Year built:
1955
A broker reciprocity listing Courtesy: Griffin Realty Group 508-420-8800
View additional info

ADDITIONAL INFORMATION

Set on a wooded half-acre lot in Osterville, this 2-bedroom, 1.5-bath ranch offers comfortable one-level living and a peaceful connection to the outdoors. Hardwood floors and natural light brighten the living spaces, while a large bay window makes the room currently used as an office an inviting place to work or unwind. The kitchen opens to the dining area, and a patio provides a spot to relax beneath the trees. Enjoy the spacious, level backyard with room to garden or gather around a fire. The seller has cleared underbrush from the rear of the lot and obtained a mortgage inspection plan and lot survey while exploring the potential for an ADU; buyers should verify feasibility and permitting with the town. A full basement, storage shed, gas heat, town water, and a paved driveway with parking for three complete the property. Convenient to Osterville's shops, beaches, golf, and walking trails.

Beds:
6
Baths:
9.00
Sq.Ft.:
9,464
Status:
NEW LISTING
MLS#:
22604836
Type:
Single Family
Lot size:
2.35 Acres
Year built:
2002
A broker reciprocity listing Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties 508-420-1414
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ADDITIONAL INFORMATION

Presiding over West Bay, this extraordinary waterfront estate spans 2.35 pristine acres with breathtaking views in an unrivaled location. A park-like driveway winds through manicured grounds with sculpted boxwood hedges and vibrant hydrangeas, creating a sense of privacy and grandeur as you approach the residence. A private dock provides immediate access to West Bay and Nantucket Sound, while the waterside swimming pool and pool house create a resort-like atmosphere. Inside, the residence showcases fine architectural millwork, soaring ceilings, limestone flooring, and six fireplaces across its gracious living spaces. The intuitive layout centers around an impressive main living room where French doors trace the water side of the home, allowing natural light to pour inside while framing panoramic views. Cooking and daily living center around the gourmet kitchen, which features a custom wood center island with seating, professional-grade appliances, and natural stone countertops. Exceptional quality and attention to detail are evidenced throughout, from the oval wood-paneled library with built-in bookshelves to the industrial-grade HVAC system ensuring the utmost comfort. Six well-appointed en suite bedrooms provide exceptional accommodations for all, including a luxurious primary suite with two full bathrooms, two dressing rooms, and serene views of the water. Outside, an expansive stone patio surrounds the swimming pool and spa, providing an effortless setting for al fresco dining and entertaining amidst a stunning backdrop. Combining refined craftsmanship and modern luxury in one of Cape Cod's most coveted neighborhoods, this inimitable waterfront estate is located minutes from Wianno, Oyster Harbors, Main Street, and everything Osterville has to offer.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,501
Status:
Active
MLS#:
22604805
Type:
Single Family
Lot size:
0.26 Acres
Year built:
1977
A broker reciprocity listing Courtesy: Margo & Company 508-428-4443
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ADDITIONAL INFORMATION

Osterville Beauty! Nestled on a private lot offering a very private year yard with hot tub, fire pit deck, grill area and shed with Tiki bar! The interior of this 3 bedroom, 2.5 bath home shows like new! ideal floor plan for entertaining! The family room with beamed ceiling, nautical trim and fireplace is the perfect spot for "movie night!". The easy to navigate kitchen is fully applianced, with upgraded cabinets, granite counters and breakfast bar plus half bath. The primary bedroom is on the first level offering a private ensuite bath with Shower and separate spa tub, plus walk in closet! Perfect! hardwood floors throughout and on both levels. 2 bedrooms a d full bath complete the 2nd floor. The partially finished basement provides laundry and extra recreation or home office space. 1 car attached garage completes the property. Minutes to Osterville village center for dining, boutique shopping, galleries and more. 2.1 miles to stunning Dowses Beach!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,523
Status:
Active
MLS#:
22604641
Type:
Single Family
Lot size:
1.52 Acres
Year built:
1999
A broker reciprocity listing Courtesy: Griffin Realty Group 508-420-8800
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ADDITIONAL INFORMATION

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 character. And every bathroom is truly amazing, with beautiful finishes and a polished, inviting feel. The extraordinary primary bedroom is a true sanctuary, with abundant windows creating an atmosphere that feels both grand and intimate. The spa-like primary bath features a dual vanity, separate garden tub, and beautiful finishes, offering a serene place to begin and end the day. Outside, a paver patio surrounds the sparkling swimming pool and outdoor BBQ, creating a private setting made for long sunny afternoons and evenings gathered with friends. Add to this the huge, partially finished basement and garage to provide abundant storage and flexibility. A home where sunlight, greenery, and Cape Cod ease come together beautifully. Come view today!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,116
Status:
Active
MLS#:
22604478
Type:
Single Family
Lot size:
0.34 Acres
Year built:
1999
A broker reciprocity listing Courtesy: Sotheby's International Realty 508-428-9115
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ADDITIONAL INFORMATION

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

Beds:
3
Baths:
3.00
Sq.Ft.:
1,844
Status:
Active
MLS#:
22604426
Type:
Single Family
Lot size:
1.11 Acres
Year built:
1956
A broker reciprocity listing Courtesy: Compass Massachusetts, LLC 508-206-8726
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ADDITIONAL INFORMATION

Beautifully renovated and thoughtfully improved, 23 & 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. Additional parcel offers potential future possibilities, subject to approvals. 23 & 27 Swift Avenue are being sold together. 27 Swift may offer some additional developmental options (G.L. c. 40a 2024)

Beds:
2
Baths:
3.00
Sq.Ft.:
1,564
Status:
Active
MLS#:
22604395
Type:
Condo
Year built:
2023
A broker reciprocity listing Courtesy: Compass Massachusetts, LLC 508-206-8726
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ADDITIONAL INFORMATION

LIKE-NEW IN OSTERVILLE'S COVETED WIANNO AREA! Rare opportunity to own a free-standing Osterville condo/golf villa offering effortless luxury and low-maintenance Cape Cod living. Built in 2023 and lightly lived in, this beautifully appointed home is moments from Osterville Village, Wianno Golf Club, Dowses Beach, marinas, shops and dining. Natural light pours through the open, airy interior featuring soaring ceilings, hardwood floors and a gas fireplace. The oversized gourmet kitchen features upgraded countertops, Bosch appliances and custom finishes. Two spacious bedrooms, 2.5 baths, plus separate living and family rooms provide exceptional flexibility. The serene primary suite features a spa-like bath. Second bedroom with walk-in closet. Large sliders open to an expansive fenced private patio, complemented by an outdoor shower. HERS 53 energy rating, Navien on-demand hot water and central vacuum complete this turnkey Osterville retreat. Nearly new. Exceptionally light. Effortlessly ideal for Cape Cod living.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,856
Status:
Active
MLS#:
22604277
Type:
Single Family
Lot size:
0.31 Acres
Year built:
1953
A broker reciprocity listing Courtesy: Sotheby's International Realty 508-428-9115
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ADDITIONAL INFORMATION

One of the best values among homes for sale in Osterville! Welcome to 329 Swift Avenue, a turnkey Osterville home offered at $799,000 with an established rental history, a desirable walk-to-village location, and exceptional future potential. Set on approximately .3 acres, this charming Cape Cod property offers the space buyers are looking for, including a generous yard with potential for a pool, subject to permitting.Located just minutes from the heart of Osterville Village, this home puts shopping, dining, coffee, beaches and the best of the Cape Cod lifestyle within easy reach. Whether you are searching for a year-round Osterville home, Cape Cod summer house, second home, or investment property, 329 Swift Avenue offers a rare combination of location, value and versatility. The property is being offered turnkey, allowing a new owner to begin enjoying it immediately or continue taking advantage of its proven rental history. With its walkable Osterville location, oversized lot, rental income history and under a 1 million, this is an outstanding opportunity in one of Cape Cod's most sought-after villages. The first photo is a virtual rendering showcasing potential curb appeal improvements, including a new cottage-style front door, window boxes, and an additional window. Please note that the seller will not be performing any of this work.

Beds:
2
Baths:
2.00
Sq.Ft.:
2,010
Status:
Active
MLS#:
22604062
Type:
Single Family
Lot size:
0.5 Acres
Year built:
2000
A broker reciprocity listing Courtesy: William Raveis Real Estate & Home Services 508-428-3320
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ADDITIONAL INFORMATION

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

Beds:
3
Baths:
2.00
Sq.Ft.:
1,248
Status:
Active
MLS#:
22604019
Type:
Single Family
Lot size:
0.5 Acres
Year built:
1985
A broker reciprocity listing Courtesy: Compass Massachusetts, LLC 508-206-8726
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ADDITIONAL INFORMATION

Welcome to 111 W Wind Cir, a beautifully renovated single-family home nestled in the heart of Osterville, MA. This stunning 3-bedroom, 2-bathroom property has been thoughtfully updated and offers comfortable living across 1,248 square feet of well-designed space. Step inside to find a bright and airy layout with six inviting rooms, perfect for relaxing or entertaining. The newly renovated kitchen boasts modern updates and plenty of space to cook and gather. Both bathrooms have been tastefully updated to offer a fresh, contemporary feel. Cozy up by the charming fireplace in the living area, creating a warm and welcoming ambiance throughout the seasons. Outside, enjoy the serene surroundings from your private deck - ideal for morning coffee, evening dinners, or simply unwinding in nature. The home offers the convenience of air conditioning to keep you comfortable year-round. A walk out basement offers exceptional additional living space and is tastefully finished. Parking will never be a concern with an included garage and additional parking spaces. Whether you're looking for a full-time residence or a seasonal retreat, this property offers both comfort and practicality in a fant

Beds:
4
Baths:
3.00
Sq.Ft.:
2,050
Status:
Active
MLS#:
22603965
Type:
Single Family
Lot size:
0.82 Acres
Year built:
1961
A broker reciprocity listing Courtesy: The Foley Company 508-685-8928
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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:
Active
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
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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 beach. A wooded drive gives way to manicured grounds of nearly two acres, transporting one to a private seaside resort as the ocean comes into view. Inside, an open layout caters to modern living with an eat-in chef's kitchen equipped with professional-grade appliances, seamlessly blending with a fireplaced living area. Oversized windows and glass doors line the waterside of the home, framing spectacular vistas and effortlessly connecting to the outdoors where a covered wooden deck 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:
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:
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
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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:
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:
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
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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
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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
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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
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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
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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:
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
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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
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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.

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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

    $1,053,500
    -3276800%
    change since last quarter
  • # Active listings

    40
    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