Osterville Massachusetts Real Estate & Homes For Sale

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$1,400,000
3bd
3ba
3182sqft
17,860Sqft

35 Waterfield Road
Osterville, Massachusetts 02655

Nicole DeFrancesco
SilverStone Capeside Realty Group
Welcome home to this meticulously maintained & lovingly cared for 3 bedroom / 3 bath Cape style home. This eloquent home is in close proximity to the quaint village of Osterville w/ easy access to all the fun at beautiful Dowses Beach, Joshua's Pond, shopping, restaurants, galleries & so much more.
$4,895,000
4bd
3ba
3100sqft
41,818Sqft

149 East Bay Road
Osterville, Massachusetts 02655

Ellen Valentgas
Sotheby's International Realty
Embrace the epitome of coastal luxury in Osterville Village with this impeccably restored shingle-style residence. A striking entrance with Belgian block stonework leads to professionally landscaped grounds. The main level features an artisanal kitchen, a chic bar area, and a sumptuous primary suite with a marble bathroom. Throughout, find exquisite craftsmanship and upscale details.
$1,900,000
4bd
3ba
2386sqft
13,068Sqft

117 Spice Lane
Osterville, Massachusetts 02655

Julie White
William Raveis Real Estate & Home Services
This is your quintessential Cape Cod home in one of Osterville's sought-after locations, Oyster Hills. This astonishing home was fully-renovated in 2020 and offers an open floor-plan that is bright and happy with so much natural sunlight. Total turn-key home; just bring your clothes and your beach bag and hop into your golf cart that can easily fit into your oversized garage.
$629,900
3bd
2ba
1452sqft
15,246Sqft

111 East Osterville Road
Osterville, Massachusetts 02655

Reciprocal Agent
Reciprocal Office
Welcome to Osterville Heights! This lovely, sunny 3 bedroom 2 bath home with attached garage has been well maintained and is ready for it's new family. The main bedroom is generously sized with a private full bath. Enjoy a fireplaced living room, large family room with a gas stove, and two sets of sliders which take you out to a level private back yard. One floor living at it's best.
$8,100,000
4bd
3ba
3877sqft
57,064Sqft

200 N Bay Road
Osterville, Massachusetts 02655

Zenas Crocker
LandVest, Inc.
Envision your forever estate on the private, gated island of Oyster Harbors. This elevated 1.31-acre parcel offers the perfect canvas for your dream home. An iconic Royal Barry Wills 3,877 square foot home is currently sited, but expansion or a new home, pool, and guest house are all within reach.
$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.
$9,000,000
7bd
3ba
4028sqft
39,640Sqft

265 Sea View Avenue
Osterville, Massachusetts 02655

John B Cotton, Jr
Sotheby's International Realty
''In its proper season, every door is unlocked, every window wide open. People, too, are more open in summer, moving through the house and each other's lives as freely as the wind. Their schools and offices are distant, their guard is down, their feet are bare,'' writes George Howe Colt.
$3,995,000
5bd
5ba
5421sqft
23,087Sqft

320 Parker Road
Osterville, Massachusetts 02655

Paul E Grover
Berkshire Hathaway HomeServices Robert Paul Properties
Located a short stroll from Osterville Village, this shingle-style home showcases stunning architectural details and scenic views over Wianno Golf Course and Parker Pond. Exquisite craftsmanship is on full display throughout, from a spacious covered porch that greets visitors to a gourmet kitchen with honed granite countertops and cherry cabinetry.
$1,375,000
4bd
3ba
3795sqft
26,572Sqft

60 Deerfield Road
Osterville, Massachusetts 02655

Colleen A Riley
Sotheby's International Realty
Osterville Village! You'll fall in love with this newly remodeled Cape just a short distance to Osterville Village and Dowses Beach! With its open floor plan, updated kitchen and baths, heated sunroom and screened in porch, this property offers the perfect blend of modern convenience and classic Cape Cod charm.
$95,000
1Room(s)
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.
$95,000
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.
$699,900
2bd
2ba
1278sqft

39 Tower Hill Road # 18C
Osterville, Massachusetts 02655

Irene Best
William Raveis Real Estate & Home Services
Coastal luxury with a sense of sophistication and comfort in this newly renovated condo in the village of Osterville with an In-Town location! Stroll to the restaurants and shops! Dowses Beach a mile away! Spacious living/dining combination with lots of natural sunlight! Gorgeous kitchen with Kitchen Aid appliances, white shaker cabinetry, quartz countertops and gorgeous tile and backsplash.
$749,900
2bd
1ba
1216sqft
21,780Sqft

933-I Main Street
Osterville, Massachusetts 02655

Chris Olson
eXp Realty, LLC
Charming 2 bedroom, 1.5 bath single family ranch style home situated on a 1/2 acre of park like grounds just inside Osterville village (Gallery Place). The home is situated on a stunning and remarkably private lot surrounded by homes of significantly higher values.
$3,000
1863sqft
3,485Sqft

10 Wianno Avenue
Osterville, Massachusetts 02655

Danny M Griffin
Griffin Realty Group
Perfectly located in the heart of Osterville village this retail location is perfect for a variety of opportunities. The space offers glass display street frontage to the main showroom and includes separate spaces for office or additional retail space. This unit also includes direct basement access for additional storage and in addition room for two off street parking spaces.
$15,000
2bd
2ba
240sqft

920 Main Street BLDG 1
Osterville, Massachusetts 02655

Priscilla A Stolba
Priscilla Stolba R E
Osterville Village beautiful first floor 2 BR/2 Bath condo. Perfect for someone looking to spend the summer on Cape Cod. Just leave your car at the condo and walk downtown to restaurants, shopping and more! The unit is nicely furnished, laundry in the unit, Cozy Livingroom with gas fireplace. Sliders to private deck. Open dining room, French doors to designer kitchen with cherrywood cabinetry.
$2,595,000
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.
$2,995,000
4bd
3ba
3015sqft
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.
$660,000
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.
$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.
$13,800,000
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.
$1,349,999
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.
$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.
$439,900
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.
$1,395,000
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.
$3,995,000
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.
$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.
$10,900,000
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.
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