Osterville Massachusetts Real Estate & Homes For Sale

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$2,695,000
4bd
3ba
3478sqft
15,682Sqft

100 Meadowlark Lane
Osterville, Massachusetts 02655

Tom P Foley
The Foley Company
Location!!! One of the best in Osterville. Just a short stroll to the Village, Wianno Golf Course and North Bay landing to kayak, shellfish or just enjoy the view. This newly renovated 4 bedroom home was meticulously designed with exceptional craftsmanship. The spectacular gourmet kitchen includes top of the line appliances, a generous center island and a cozy fireplace.
$3,300,000
4bd
3ba
2694sqft
11,761Sqft

21 Cockachoiset Lane
Osterville, Massachusetts 02655

Cindy Houlihan
Berkshire Hathaway HomeServices Robert Paul Properties
A new custom home in the quaint seaside Village of Osterville! Perfectly nestled alongside Crosby Boat Yard, Nauticus Marina, Oyster Harbors Marina, The Chart Room and well-known West Bay, you will find this top of line crafted 4 bedroom, 3.5 bathroom home.
$1,100,000
3bd
3ba
1759sqft
116,741Sqft

523 Bumps River Road
Osterville, Massachusetts 02655

Danielle Chaulk
Kinlin Grover Compass
Privacy and serenity abound in this charming property located in highly desirable Osterville Village. This Cape Style Home set on 2.6 acres has deeded access to Micah's Pond, perfect for swimming, sailing, kayaking etc... The living room with cathedral beam ceiling and wood burning fireplace creates a warm inviting atmosphere.
$675,000
2bd
2ba
1155sqft

920 Main Street # 4
Osterville, Massachusetts 02655

Shaelyn Hegarty
Frank A Sullivan Real Estate
Discover a coastal sanctuary in the heart of Osterville's charming village. Boasting a prime location amongst beloved shops and restaurants, this residence offers a delightful blend of convenience and charm. Indulge in the quality craftsmanship showcased throughout this condo, which was fully renovated in 2019. The living room features shiplap-adorned walls, vaulted ceilings and a gas fireplace.
$629,900
3bd
3ba
1806sqft
22,216Sqft

65 Renoir Drive
Osterville, Massachusetts 02655

Deb E Costa
On the Move Real Estate
This home is neatly tucked away on a private lot on dead-end street just off Route 28. Privacy abounds in the backyard abutting conservation land. SELLERS HAVE INVESTED OVER $90,000 OF MAJOR UPDATES TO THE HOME. Automatic generator will keep the lights on despite any weather! Kitchen and baths on 1st and 2nd floors are remodeled. Anderson & Pella windows and doors.
$15,995,000
6bd
5ba
4254sqft
67,954Sqft

807 Sea View Avenue
Osterville, Massachusetts 02655

Ellen Valentgas
Sotheby's International Realty
Feel the world drift away as you enter this extraordinary oceanfront beach house with a private white sand beach and unobstructed, expansive views of Nantucket Sound. An awe-inspiring wall of glass spanning the length of the house frames the breathtaking seascape, creating an atmosphere of tranquility and wonder.
$679,000
3bd
2ba
1284sqft
15,246Sqft

9 Gunstock Road
Osterville, Massachusetts 02655

Robert B Kinlin
Berkshire Hathaway HomeServices Robert Paul Properties
This well-maintained Ranch style home is located on a corner lot south of Rt 28 in Osterville Woods. The living room features a cathedral ceiling and wood burning fireplace and opens into the dining and sitting area as well as a kitchen with new appliances. The primary bedroom has an updated full bath and there are newer carpets throughout the home.
$1,675,000
3bd
3ba
1520sqft
21,344Sqft

219 Pond Street
Osterville, Massachusetts 02655

Colleen A Riley
Sotheby's International Realty
Osterville Village! Discover the true feeling of coastal living in this newly remodeled home with a detached cottage, located just a short stroll away from the village and picturesque Joshua's Pond. Step inside this tastefully decorated residence that exudes chic coastal style, featuring custom french tile, quartz counters, and luxurious finishes throughout.
$1,495,000
4bd
3ba
2982sqft
25,700Sqft

38 Evans Street
Osterville, Massachusetts 02655

Elaine A Roy
Today Real Estate
Welcome to your Cape Cod Home. The attention to detail is evident throughout this newly renovated home that features Hickory hardwood floors throughout a first floor primary suite with accent wall including a fireplace, walk in closet and a very sophisticated en suite bathroom with a freestanding soaking tub, shower and his and hers vanity.
$12,900,000
4bd
4ba
5413sqft
46,174Sqft

995 Sea View Avenue
Osterville, Massachusetts 02655

Robert B Kinlin
Berkshire Hathaway HomeServices Robert Paul Properties
Experience the pinnacle of comfort and luxury from this exquisite waterfront property located in Osterville, MA, featuring a substantial deep-water dock, pristine beach, and unparalleled water views of Nantucket Sound. The owners completely transformed this residence in 2020 into a stunning modern oasis with approximately 5,400 sq. ft.
$9,950,000
5bd
4ba
7157sqft
71,874Sqft

25 Oyster Way
Osterville, Massachusetts 02655

Robert B Kinlin
Berkshire Hathaway HomeServices Robert Paul Properties
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.
$625,000
3bd
2ba
1880sqft
11,761Sqft

160 Acorn Drive
Osterville, Massachusetts 02655

Gena Gomes
Redfin Corporation
Wecome to 160 Acorn Drive, Osterville. Spacious 7 room 3 bedroom 2 bath ranch with office/bonus room. Beautiful hardwood floors with gas fireplace. Large kitchen with new dishwasher and refrigerator. Freshly painted throughout, four year old roof with large deck for entertaining. Located on a quiet street near Cape Cod Academy, Dowses Beach, Wianno Golf Club and downtown Osterville.
$699,000
4bd
2ba
1946sqft
13,504Sqft

158 Wintergreen Circle
Osterville, Massachusetts 02655

Laurie J Jacobson
eXp Realty, LLC
Location, location, location!! So close to the best that Osterville has to offer! This four-bedroom, two-bath Cape home boasts over 1900 square feet!! So many unique features this home has to offer.
$6,385,000
5bd
5ba
5924sqft
43,560Sqft

350 Windswept Way
Osterville, Massachusetts 02655

Carole B Swartz
Kinlin Grover Compass
Exceptional offering at exclusive Oyster Harbors Club on Cape Cod; Ultimate, thoughtful 2021 renovation. You will appreciate the highest standard of excellence that enhances this home's comfort and function. There are 5 bedrooms, 51/2 bathrooms.
$575,900
2bd
1ba
1052sqft
15,246Sqft

99 E Osterville Road
Osterville, Massachusetts 02655

Michelle M Tucker
William Raveis Real Estate & Home Services
Home Sweet Home in Osterville! Enjoy bright, one floor living in this delightful ranch. Sunny living room with brick fireplace. Nicely updated Eat-in kitchen with sliders leading out to the back deck overlooking the private back yard and gardens. New flooring throughout. Stackable washer/dryer in the back bedroom's closet.
$2,750,000
4bd
4ba
4064sqft
85,813Sqft

201 Smoke Valley Road
Osterville, Massachusetts 02655

Paul E Grover
Berkshire Hathaway HomeServices Robert Paul Properties
This exquisite four-bedroom home offers privacy and water views on nearly two acres in Osterville's prestigious Seapuit neighborhood, located minutes from the center of the village. A grand front porch overlooking Warren's Cove sets the stage, showcasing the timeless beauty of Cape Cod.
$1,275,000
2bd
3ba
1492sqft
11,761Sqft

218 Scudder Road
Osterville, Massachusetts 02655

Bonnie P Filiault
William Raveis Real Estate & Home Services
Exciting New Price for this Osterville Village home which offers an incredible opportunity to own a beautiful property located in this picturesque village on Cape Cod. Just a short distance from Dowses Beach and Osterville Village amenities this property embodies the quintessential Cape Cod Lifestyle and perfect blend of tranquility and convenience.
$1,375,000
3bd
2ba
1153sqft
3,920Sqft

38 Sunset Lane
Osterville, Massachusetts 02655

Colleen A Riley
Sotheby's International Realty
Osterville Village! Leave your car at home! You'll fall in love with this updated ranch set in the heart of Osterville that offers a modern and stylish coastal living experience with convenience in mind. Enjoy a fully renovated kitchen featuring quartz counters and stainless steel appliances, as well as 2 new bathrooms, updated electrical and plumbing, and HVAC system, this home is move-in ready.
$2,200,000
4bd
3ba
4245sqft
48,352Sqft

24 Farm Valley Road
Osterville, Massachusetts 02655

The Kanter Team
Kinlin Grover Compass
Nestled in the heart of picturesque Osterville,this charming Cape Cod home offers the quintessential New England coastal living experience. As you approach this property in what we call ''Hidden Farm Valley'' you'll immediately notice its stunning curb appeal. A classic Cape Cod facade with complete privacy welcomes you home.
$8,850,000
4bd
3ba
3877sqft
57,064Sqft

200 N North Bay Road
Osterville, Massachusetts 02655

Zenas Crocker
LandVest, Inc.
Iconic Royal Barry Will's designed waterfront home on Oyster Harbors. Spectacular sunset views await the new stewards of this home which affords water views from almost every room. One of a handful of true, protected, deep water docks allowing access to Nantucket Sound and south shore fishing grounds in just minutes.The home is sited on an elevated 1.31 acre lot that faces west.
$2,850
2bd
2ba
1040sqft
15,246Sqft

21 Nathans Way
Osterville, Massachusetts 02655

Carole M Phelps
ERA Cape Real Estate, LLC
YEARLY RENTAL.ONLY A SHORT DRIVE TO FAMOUS DOWSES BEACH.AS YOU CAN SEE ALL UPDATES REMODEL MAGAZINE WORTHY AMENITIES INCLUDE:Spacious Living roomUpdated kitchen with granite counter-topsnew cabinets, stainless appliances.
$1,650,000
3bd
5ba
4269sqft
12,197Sqft

12 Fire Station Road
Osterville, Massachusetts 02655

Jane N Bodrie
Sotheby's International Realty, Inc.
Nestled in Charming Osterville Village this home seamlessly blends historic elegance with contemporary amenities. Dating back to its historical roots, this 3 bedroom, 5.5 bath home boasts new additions in 2000 and 2004 that harmoniously expand its charm and functionality. Convenience is at your doorstep as you stroll to shops, restaurants, museums and visit renowned Dowses Beach.
$3,200,000
5bd
4ba
4715sqft
88,427Sqft

98 Bunker Hill Road
Osterville, Massachusetts 02655

Lee Brown
Sotheby's International Realty
A drive through lighted stone pillars alongside the sweeping lawn sets the stage. Sited on a two-acre parcel within the exclusive neighborhood of Seapuit, Osterville, is this stunning 4715 square foot contemporary style home. The dramatic cathedral ceilings, along with the automatic skylights, provide abundant natural light throughout.
$455,000
21Room(s)
2400sqft

1112 Main Street # 13
Osterville, Massachusetts 02655

Gerry Coughlan
Kinlin Grover Compass
Business warehouse condo in Osterville now available for sale. Unit # 13 with 1 large overhead bay door and 1 access door. Open unit with 1/2 bath and full loft above for additional storage or future office space. Excellent village location, investment, business or personal hobby.
$99,900
360sqft

920A Main Street # 17
Osterville, Massachusetts 02655

Patty Radford
Radford Realty Group
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.
$99,900
360sqft

920A Main Street # 18
Osterville, Massachusetts 02655

Patty Radford
Radford Realty Group
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 (#17) that is for sale as well. A rare opportunity in the village for much needed space.
$1,495,000
4bd
2ba
2379sqft
12,197Sqft

179 Robbins Street
Osterville, Massachusetts 02655

Marcus Nese
William Raveis Real Estate & Home Services
Outstanding Osterville residence, perfectly situated, close to Dowses Beach and Village attractions yet quietly tucked-away. Spacious four bedroom Gambrel-style home, recent renovations and improvements make this light and bright property, with an open floor plan, ready for immediate enjoyment. Custom quality craftsmanship is evident throughout.
$2,595,000
3bd
3ba
2972sqft
9,148Sqft

18 Parker Road
Osterville, Massachusetts 02655

W&W Boston/Cape Cod Connection
Compass Massachusetts, LLC
Experience the ultimate in coastal living with your dream home in Osterville Village! This Cape Cod gem has undergone meticulous renovations and boasts an ideal location, steps away from the shops, restaurants, and famous Dowses Beach. If you love to cook you will be delighted with the newly built chef's kitchen and butler pantry. Are you wanting a quiet area to read a good book or do a puzzle.
$4,290,000
6bd
5ba
4511sqft
20,038Sqft

101 Warren Street
Osterville, Massachusetts 02655

W&W Boston/Cape Cod Connection
Compass Massachusetts, LLC
Welcome to this magnificent 2021-built real estate gem located in the sought-after Wianno neighborhood. With its beautiful open spaces, this home is perfectly designed for accommodating large gatherings and entertaining. The property features an inviting in-ground pool complete with a safety cover, allowing for enjoyment with peace of mind.
$2,350,000
3bd
3ba
3845sqft
46,174Sqft

1676 South County Road
Osterville, Massachusetts 02655

Gail C Germain Martis
Sotheby's International Realty
Pristine Federal Colonial Revival has open floor plan with private areas for today's lifestyle. High-end original and updated quality materials, appliances and mechanics throughout. Cedar roofing, hardwood flooring, marble baths, custom moldings, high ceilings and oversized windows all create a serene and bright environment.
$3,250,000
106,722Sqft

30 Indian Trail
Osterville, Massachusetts 02655

Zenas Crocker
LandVest, Inc.
The site of Mrs. Mellon's orchard enjoys a bucolic landscape view with prevailing southwest winds. The largest lot at The Cove at Oyster Harbors should easily accommodate multiple structures, a pool, gardens, tennis court and so forth. Access on Oyster Harbors best street, with underground utilities assures complete privacy. Additional lots available for purchase.
$3,000,000
90,605Sqft

0 Seapuit River Road
Osterville, Massachusetts 02655

Zenas Crocker
LandVest, Inc.
This 2.08-acre lot affords the potential for a generous building envelope and privacy is assured with protected land just across the street. The site would allow up to 8 bedrooms across several buildings, garage, pool, pool house and so forth. If combined with The Point (0 Indian Trail), the potential for Oyster Harbors most significant interior estate becomes clear.
$3,550,000
98,881Sqft

21 Indian Trail
Osterville, Massachusetts 02655

Zenas Crocker
LandVest, Inc.
Facing southwest this 2.27 acre lot has the potential to have a nice water view enjoying the prevailing southwesterly seasonal winds. A design for home, pool and garage guest building are in place. Indian trail affords Oyster Harbors most prestigious address with underground power lines. Truly a sanctuary within a private island. Additional lots available for purchase.
$3,125,000
87,556Sqft

0 Indian Trail
Osterville, Massachusetts 02655

Zenas Crocker
LandVest, Inc.
This gently sloping 2.01-acre site feels like old Cape Cod. The site has room for everything an extended family might want: Main house, guest building, garage, pool and so forth. Great light, complete privacy and the best street on Oyster Harbors. Additional lots available for purchase.
$3,100,000
100,188Sqft

0 Seapuit River Road
Osterville, Massachusetts 02655

Zenas Crocker
LandVest, Inc.
This magnificent, gently sloping 2.3-acre lot should allow total privacy with room for an estate with 8 or more bedrooms. Guest building, garage, tennis, pool and pool house are all possibilities. A water view may be possible! Additional lots available for purchase.
$12,500,000
8bd
4ba
4033sqft
106,722Sqft

227 Bridge Street
Osterville, Massachusetts 02655

Robert B Kinlin
Berkshire Hathaway HomeServices Robert Paul Properties
From its unparalleled location on Little Island in Osterville, this special waterfront estate overlooks the sparkling waters of West Bay and offers breathtaking water vistas from its private and elevated setting. This 2.45-acre lot features a substantial deep water dock, private sandy beach and an expansive yard perfect for entertaining.
$13,000,000
7bd
6ba
4896sqft
260,489Sqft

255 Bayberry Way
Osterville, Massachusetts 02655

Robert B Kinlin
Berkshire Hathaway HomeServices Robert Paul Properties
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.
$30,000,000
7bd
9ba
15500sqft
159,430Sqft

835 Sea View Avenue
Osterville, Massachusetts 02655

Paul E Grover
Berkshire Hathaway HomeServices Robert Paul Properties
Set on Osterville's exclusive Sea View Avenue with commanding views over Nantucket Sound and an unprecedented 280 feet of private sandy beach, a once-in-a-lifetime coastal oasis awaits. Magnificent landscaping sets the stage, with specimen trees and lush plantings that offer total privacy across 3.66 acres.
$870,000
2bd
2ba
2350sqft

105 Parker Road # D
Osterville, Massachusetts 02630

Joanne M Murphy
Sotheby's International Realty
From the minute you walk into The Fairways you know you have arrived at a special place. The beautifully landscaped grounds and inviting front porch are just the beginning of a great experience. This first floor end unit overlooks the Wianno Golf Course. Features include gleaming hardwood floors, a gourmet kitchen and master suite.
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