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17 Homes For Sale in The Neighborhood Of Osterville In Osterville, MA

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$6,495,000Est. Payment
5 Beds | 6 Baths | 4,938 Sqft

71 Sand Point, Osterville, MA 02655

House For Sale

This home is located at 71 Sand Point Osterville, MA 02655 US and has been listed on Homes.com since 18 September 2020 and is currently priced at $6,495,000, approximately $1315 per square foot. This property was built in 1951. 71 Sand Point is within the school district(s) Barnstable Public Schools with nearby schools including Barnstable United Elementary School, Barnstable Intermediate School, and Barnstable High School. Similar properties nearby are 71 Sand Point, <a href="/property/821-old-post-rd-cotuit-ma-02635/id-500014473787/">821 Old Post Rd</a>, <a href="/property/360-n-bay-rd-osterville-ma-02655/id-900001031392/">360 N Bay Rd</a>, <a href="/property/307-ocean-view-ave-cotuit-ma-02635/id-500014473064/">307 Ocean View Ave</a>, 285 Baxter Neck Rd, <a href="/property/250-windswept-way-osterville-ma-02655/id-900001031322/">250 Windswept Way</a>, <a href="/property/206-e-bay-rd-osterville-ma-02655/id-500014545845/">206 E Bay Rd</a>, <a href="/property/92-n-bay-rd-osterville-ma-02655/id-900001031413/">92 N Bay Rd</a>, <a href="/property/120-vineyard-rd-cotuit-ma-02635/id-500014472084/">120 Vineyard Rd</a>, and <a href="/property/501-eel-river-rd-osterville-ma-02655/id-500014544507/">501 Eel River Rd</a>.

$2,895,000Est. Payment
6 Beds | 6 Baths | 7,126 Sqft

473 Grand Island Drive, Osterville, MA 02655

House For Sale

This home is located at 473 Grand Island Drive Osterville, MA 02655 US and has been listed on Homes.com since 18 September 2020 and is currently priced at $2,895,000, approximately $406 per square foot. This property was built in 1991. 473 Grand Island Drive is within the school district(s) Barnstable Public Schools with nearby schools including Barnstable United Elementary School, Barnstable Intermediate School, and Barnstable High School. Similar properties nearby are <a href="/property/473-grand-island-dr-osterville-ma-02655/id-900001031354/">473 Grand Island Dr</a>, <a href="/property/292-grand-island-dr-osterville-ma-02655/id-900001031347/">292 Grand Island Dr</a>, <a href="/property/375-baxters-neck-rd-marstons-mills-ma-02648/id-500014538285/">375 Baxters Neck Rd</a>, <a href="/property/285-windswept-way-osterville-ma-02655/id-900001031348/">285 Windswept Way</a>, <a href="/property/505-baxters-neck-rd-marstons-mills-ma-02648/id-500014538290/">505 Baxters Neck Rd</a>, <a href="/property/100-eel-river-rd-osterville-ma-02655/id-500014544679/">100 Eel River Rd</a>, <a href="/property/15-deans-hollow-rd-mashpee-ma-02649/id-900001031026/">15 Deans Hollow Rd</a>, <a href="/property/osterville-ma-02655/id-500014544292/">142 Great Bay Rd</a>, <a href="/property/30-mayflower-ln-osterville-ma-02655/id-500014545775/">30 Mayflower Ln</a>, and <a href="/property/osterville-ma-02655/id-500014544860/">209 Bay St</a>.

$8,500,000Est. Payment
5 Beds | 4 Baths | 5,000 Sqft

274 Carriage Road, Osterville, MA 02655

House For Sale

This home is located at 274 Carriage Road Osterville, MA 02655 US and has been listed on Homes.com since 27 August 2020 and is currently priced at $8,500,000, approximately $1700 per square foot. This property was built in 1942. 274 Carriage Road is within the school district(s) Barnstable Public Schools with nearby schools including Barnstable United Elementary School, Barnstable Intermediate School, and Barnstable High School. Similar properties nearby are 274 Carriage Rd, <a href="/property/360-n-bay-rd-osterville-ma-02655/id-900001031392/">360 N Bay Rd</a>, <a href="/property/134-s-bay-rd-osterville-ma-02655/id-500014544381/">134 S Bay Rd</a>, <a href="/property/250-windswept-way-osterville-ma-02655/id-900001031322/">250 Windswept Way</a>, <a href="/property/206-e-bay-rd-osterville-ma-02655/id-500014545845/">206 E Bay Rd</a>, <a href="/property/501-eel-river-rd-osterville-ma-02655/id-500014544507/">501 Eel River Rd</a>, <a href="/property/307-ocean-view-ave-cotuit-ma-02635/id-500014473064/">307 Ocean View Ave</a>, <a href="/property/120-vineyard-rd-cotuit-ma-02635/id-500014472084/">120 Vineyard Rd</a>, and <a href="/property/183-bay-st-osterville-ma-02655/id-500014544855/">183 Bay St</a>.

$1,495,000Est. Payment
8 Beds | 5 Baths | 2,811 Sqft

20 Grand Island Drive, Osterville, MA 02655

House For Sale

This home is located at 20 Grand Island Drive Osterville, MA 02655 US and has been listed on Homes.com since 6 August 2020 and is currently priced at $1,495,000, approximately $532 per square foot. This property was built in 1939. 20 Grand Island Drive is within the school district(s) Barnstable Public Schools with nearby schools including Barnstable United Elementary School, Barnstable Intermediate School, and Barnstable High School. Similar properties nearby are <a href="/property/20-grand-island-dr-osterville-ma-02655/id-900001031404/">20 Grand Island Dr</a>, 50 Nickerson Dr, <a href="/property/osterville-ma-02655/id-500014546525/">99 Swift Ave</a>, <a href="/property/192-mistic-dr-marstons-mills-ma-02648/id-500014538545/">192 Mistic Dr</a>, <a href="/property/21-bright-coves-way-mashpee-ma-02649/id-500014528272/">21 Bright Coves Way</a>, <a href="/property/199-e-bay-rd-12-osterville-ma-02655/id-500014545826/">199 E Bay Rd 12</a>, <a href="/property/205-seapuit-rd-osterville-ma-02655/id-500014544405/">205 Seapuit Rd</a>, <a href="/property/72-eagle-dr-mashpee-ma-02649/id-500014534856/">72 Eagle Dr</a>, <a href="/property/75-the-hts-mashpee-ma-02649/id-500014534897/">75 The Hts</a>, and <a href="/property/1783-main-st-cotuit-ma-02635/id-1000083882586/">1783 Main St</a>.

$7,495,000Est. Payment
6 Beds | 5 Baths | 4,235 Sqft

250 Windswept Way, Osterville, MA 02655

House For Sale

This home is located at 250 Windswept Way Osterville, MA 02655 US and has been listed on Homes.com since 31 August 2020 and is currently priced at $7,495,000, approximately $1770 per square foot. This property was built in 1925. 250 Windswept Way is within the school district(s) Barnstable Public Schools with nearby schools including Barnstable United Elementary School, Barnstable Intermediate School, and Barnstable High School. Similar properties nearby are <a href="/property/250-windswept-way-osterville-ma-02655/id-900001031322/">250 Windswept Way</a>, <a href="/property/360-n-bay-rd-osterville-ma-02655/id-900001031392/">360 N Bay Rd</a>, <a href="/property/206-e-bay-rd-osterville-ma-02655/id-500014545845/">206 E Bay Rd</a>, <a href="/property/501-eel-river-rd-osterville-ma-02655/id-500014544507/">501 Eel River Rd</a>, <a href="/property/307-ocean-view-ave-cotuit-ma-02635/id-500014473064/">307 Ocean View Ave</a>, <a href="/property/120-vineyard-rd-cotuit-ma-02635/id-500014472084/">120 Vineyard Rd</a>, <a href="/property/183-bay-st-osterville-ma-02655/id-500014544855/">183 Bay St</a>, 274 Carriage Rd, <a href="/property/134-s-bay-rd-osterville-ma-02655/id-500014544381/">134 S Bay Rd</a>, and 71 Sand Point.

$3,400,000Est. Payment
5 Beds | 6 Baths | 4,727 Sqft

285 Windswept Way, Osterville, MA 02655

House For Sale

This home is located at 285 Windswept Way Osterville, MA 02655 US and has been listed on Homes.com since 18 August 2020 and is currently priced at $3,400,000, approximately $719 per square foot. This property was built in 1999. 285 Windswept Way is within the school district(s) Barnstable Public Schools with nearby schools including Barnstable United Elementary School, Barnstable Intermediate School, and Barnstable High School. Similar properties nearby are <a href="/property/375-baxters-neck-rd-marstons-mills-ma-02648/id-500014538285/">375 Baxters Neck Rd</a>, <a href="/property/285-windswept-way-osterville-ma-02655/id-900001031348/">285 Windswept Way</a>, <a href="/property/mashpee-ma-02649/id-500014528075/">3 Bight Cir</a>, <a href="/property/marstons-mills-ma-02648/id-500014538290/">505 Baxters Neck Rd</a>, <a href="/property/473-grand-island-dr-osterville-ma-02655/id-900001031354/">473 Grand Island Dr</a>, <a href="/property/100-eel-river-rd-osterville-ma-02655/id-500014544679/">100 Eel River Rd</a>, <a href="/property/30-mayflower-ln-osterville-ma-02655/id-500014545775/">30 Mayflower Ln</a>, <a href="/property/352-mashpee-neck-rd-mashpee-ma-02649/id-500014536334/">352 Mashpee Neck Rd</a>, <a href="/property/29-ockway-bay-rd-mashpee-ma-02649/id-500014527603/">29 Ockway Bay Rd</a>, and <a href="/property/292-grand-island-dr-osterville-ma-02655/id-900001031347/">292 Grand Island Dr</a>.

$1,395,000Est. Payment
3 Beds | 4 Baths | 3,021 Sqft

21 Windrush Lane, Osterville, MA 02655

House For Sale

This home is located at 21 Windrush Lane Osterville, MA 02655 US and has been listed on Homes.com since 3 September 2020 and is currently priced at $1,395,000, approximately $462 per square foot. This property was built in 1977. 21 Windrush Lane is within the school district(s) Barnstable Public Schools with nearby schools including Barnstable United Elementary School, Barnstable Intermediate School, and Barnstable High School. Similar properties nearby are <a href="/property/199-e-bay-rd-12-osterville-ma-02655/id-500014545826/">199 E Bay Rd 12</a>, <a href="/property/438-quinaquisset-ave-mashpee-ma-02649/id-500014535649/">438 Quinaquisset Ave</a>, <a href="/property/21-windrush-ln-osterville-ma-02655/id-500014544383/">21 Windrush Ln</a>, <a href="/property/marstons-mills-ma-02648/id-500014538379/">3635 Falmouth Rd</a>, <a href="/property/95-wianno-cir-osterville-ma-02655/id-500014545744/">95 Wianno Cir</a>, <a href="/property/192-mistic-dr-marstons-mills-ma-02648/id-500014538545/">192 Mistic Dr</a>, <a href="/property/205-seapuit-rd-osterville-ma-02655/id-500014544405/">205 Seapuit Rd</a>, <a href="/property/1783-main-st-cotuit-ma-02635/id-1000083882586/">1783 Main St</a>, 165 Baxter Neck Rd, and <a href="/property/44-fairwinds-dr-osterville-ma-02655/id-500014546508/">44 Fairwinds Dr</a>.

$7,999,000Est. Payment
7 Beds | 10 Baths | 7,727 Sqft

134 South Bay Road, Osterville, MA 02655

House For Sale

This home is located at 134 South Bay Road Osterville, MA 02655 US and has been listed on Homes.com since 13 July 2020 and is currently priced at $7,999,000, approximately $1035 per square foot. This property was built in 1998. 134 South Bay Road is within the school district(s) Barnstable Public Schools with nearby schools including Barnstable United Elementary School, Barnstable Intermediate School, and Barnstable High School. Similar properties nearby are <a href="/property/134-s-bay-rd-osterville-ma-02655/id-500014544381/">134 S Bay Rd</a>, <a href="/property/360-n-bay-rd-osterville-ma-02655/id-900001031392/">360 N Bay Rd</a>, 274 Carriage Rd, <a href="/property/250-windswept-way-osterville-ma-02655/id-900001031322/">250 Windswept Way</a>, <a href="/property/206-e-bay-rd-osterville-ma-02655/id-500014545845/">206 E Bay Rd</a>, 71 Sand Point, <a href="/property/183-bay-st-osterville-ma-02655/id-500014544855/">183 Bay St</a>, <a href="/property/120-vineyard-rd-cotuit-ma-02635/id-500014472084/">120 Vineyard Rd</a>, <a href="/property/307-ocean-view-ave-cotuit-ma-02635/id-500014473064/">307 Ocean View Ave</a>, and <a href="/property/501-eel-river-rd-osterville-ma-02655/id-500014544507/">501 Eel River Rd</a>.

$300,000
$6,950,000Est. Payment
6 Beds | 6 Baths | 3,719 Sqft

360 North Bay Road, Osterville, MA 02655

House For Sale

This home is located at 360 North Bay Road Osterville, MA 02655 US and has been listed on Homes.com since 26 June 2020 and is currently priced at $6,950,000, approximately $1869 per square foot. This property was built in 1949. 360 North Bay Road is within the school district(s) Barnstable Public Schools with nearby schools including Barnstable United Elementary School, Barnstable Intermediate School, and Barnstable High School. Similar properties nearby are <a href="/property/360-n-bay-rd-osterville-ma-02655/id-900001031392/">360 N Bay Rd</a>, <a href="/property/307-ocean-view-ave-cotuit-ma-02635/id-500014473064/">307 Ocean View Ave</a>, <a href="/property/250-windswept-way-osterville-ma-02655/id-900001031322/">250 Windswept Way</a>, 71 Sand Point, <a href="/property/501-eel-river-rd-osterville-ma-02655/id-500014544507/">501 Eel River Rd</a>, <a href="/property/120-vineyard-rd-cotuit-ma-02635/id-500014472084/">120 Vineyard Rd</a>, <a href="/property/134-s-bay-rd-osterville-ma-02655/id-500014544381/">134 S Bay Rd</a>, and <a href="/property/206-e-bay-rd-osterville-ma-02655/id-500014545845/">206 E Bay Rd</a>.

$4,300,000Est. Payment
6 Beds | 7 Baths | 4,958 Sqft

320 Seapuit River Road, Osterville, MA 02655

House For Sale

This home is located at 320 Seapuit River Road Osterville, MA 02655 US and has been listed on Homes.com since 8 May 2020 and is currently priced at $4,300,000, approximately $867 per square foot. This property was built in 1985. 320 Seapuit River Road is within the school district(s) Barnstable Public Schools with nearby schools including Barnstable United Elementary School, Barnstable Intermediate School, and Barnstable High School. Similar properties nearby are 230 Seapuit River Rd, <a href="/property/osterville-ma-02655/id-500014544704/">95 Eel River Rd</a>, <a href="/property/29-ockway-bay-rd-mashpee-ma-02649/id-500014527603/">29 Ockway Bay Rd</a>, <a href="/property/46-little-island-dr-osterville-ma-02655/id-500014544378/">46 Little Island Dr</a>, <a href="/property/mashpee-ma-02649/id-500014528075/">3 Bight Cir</a>, <a href="/property/mashpee-ma-02649/id-500014529710/">23 Ocean Bluff Dr</a>, <a href="/property/352-mashpee-neck-rd-mashpee-ma-02649/id-500014536334/">352 Mashpee Neck Rd</a>, <a href="/property/94-starboard-ln-osterville-ma-02655/id-500014546701/">94 Starboard Ln</a>, <a href="/property/cotuit-ma-02635/id-1000026103778/">108 Little River Rd</a>, and 315 Baxter Neck Rd.

$1,995,000Est. Payment
4 Beds | 5 Baths | 3,590 Sqft

95 Windswept Way, Barnstable, MA 02655

House For Sale

95 Windswept Way in exclusive Oyster Harbors, with gated 24/365 security, enjoys the prevailing southwest summer breeze reminiscent of olde Cape Cod. The shingle style Home was thoughtfully placed on an elevated, very private lot and designed by famed architect Don Hisaka. This bright, airy sun filled home is a wonderful retreat for family and friends. Graceful architectural features inside and out can't help but put a smile on the faces of young and old... This home has been enjoyed, lovingly maintained and updated over the years. Thoughtful layout lends itself to entertaining large groups, yet allows guests intimate spaces as well. Walls of windows and doors bring nature inside and provide smooth transition for everyone to enjoy the expansive yard, decks, patios & requisite summer barbecues! Separate guest wing feature 3 bedrooms & magnificent bath. Upstairs is the very private master bedroom suite. Did we mention Beach and boating access are a 9 iron away!? This home is aggressively priced, represents a great investment, and we promise a viewing will be well worth the investment of your time!

$2,995,000Est. Payment
6 Beds | 6 Baths | 4,707 Sqft

292 Grand Island Drive, Osterville, MA 02655

House For Sale

This home is located at 292 Grand Island Drive Osterville, MA 02655 US and has been listed on Homes.com since 6 February 2020 and is currently priced at $2,995,000, approximately $636 per square foot. This property was built in 1983. 292 Grand Island Drive is within the school district(s) Barnstable Public Schools with nearby schools including Barnstable United Elementary School, Barnstable Intermediate School, and Barnstable High School. Similar properties nearby are <a href="/property/473-grand-island-dr-osterville-ma-02655/id-900001031354/">473 Grand Island Dr</a>, <a href="/property/292-grand-island-dr-osterville-ma-02655/id-900001031347/">292 Grand Island Dr</a>, <a href="/property/375-baxters-neck-rd-marstons-mills-ma-02648/id-500014538285/">375 Baxters Neck Rd</a>, <a href="/property/285-windswept-way-osterville-ma-02655/id-900001031348/">285 Windswept Way</a>, <a href="/property/94-starboard-ln-osterville-ma-02655/id-500014546701/">94 Starboard Ln</a>, <a href="/property/505-baxters-neck-rd-marstons-mills-ma-02648/id-500014538290/">505 Baxters Neck Rd</a>, <a href="/property/100-eel-river-rd-osterville-ma-02655/id-500014544679/">100 Eel River Rd</a>, <a href="/property/osterville-ma-02655/id-500014544292/">142 Great Bay Rd</a>, <a href="/property/30-mayflower-ln-osterville-ma-02655/id-500014545775/">30 Mayflower Ln</a>, and <a href="/property/352-mashpee-neck-rd-mashpee-ma-02649/id-500014536334/">352 Mashpee Neck Rd</a>.

$2,500,000
$19,500,000Est. Payment
9 Beds | 7 Baths | 5,516 Sqft

198 & 227 Bridge Street, Osterville, MA 02655

House For Sale

This home is located at 198 & 227 Bridge Street Osterville, MA 02655 US and has been listed on Homes.com since 3 July 2019 and is currently priced at $19,500,000, approximately $3535 per square foot. This property was built in 1900. 198 & 227 Bridge Street is within the school district(s) Barnstable Public Schools with nearby schools including Barnstable United Elementary School, Barnstable Intermediate School, and Barnstable High School. Similar properties nearby are 227 Bridge St #198 and <a href="/property/osterville-ma-02655/id-500014544357/">227 Bridge St</a>.

$200,000
$4,795,000Est. Payment
5 Beds | 6 Baths | 5,680 Sqft

46 Little Island Drive, Osterville, MA 02655

House For Sale

This home is located at 46 Little Island Drive Osterville, MA 02655 US and has been listed on Homes.com since 14 August 2019 and is currently priced at $4,795,000, approximately $844 per square foot. This property was built in 1998. 46 Little Island Drive is within the school district(s) Barnstable Public Schools with nearby schools including Barnstable United Elementary School, Barnstable Intermediate School, and Barnstable High School. Similar properties nearby are <a href="/property/46-little-island-dr-osterville-ma-02655/id-500014544378/">46 Little Island Dr</a>, <a href="/property/315-baxters-neck-rd-marstons-mills-ma-02648/id-500014538293/">315 Baxters Neck Rd</a>, 315 Baxter Neck Rd, <a href="/property/821-old-post-rd-cotuit-ma-02635/id-500014473787/">821 Old Post Rd</a>, <a href="/property/mashpee-ma-02649/id-500014528075/">3 Bight Cir</a>, <a href="/property/cotuit-ma-02635/id-1000026103778/">108 Little River Rd</a>, 230 Seapuit River Rd, 285 Baxter Neck Rd, <a href="/property/92-n-bay-rd-osterville-ma-02655/id-900001031413/">92 N Bay Rd</a>, and <a href="/property/osterville-ma-02655/id-500014545559/">191 Sea View Ave</a>.

$5,500,000Est. Payment
6 Beds | 7 Baths | 6,482 Sqft

92 North Bay Road, Osterville, MA 02655

House For Sale

This home is located at 92 North Bay Road Osterville, MA 02655 US and has been listed on Homes.com since 14 February 2020 and is currently priced at $5,500,000, approximately $849 per square foot. This property was built in 1981. 92 North Bay Road is within the school district(s) Barnstable Public Schools with nearby schools including Barnstable United Elementary School, Barnstable Intermediate School, and Barnstable High School. Similar properties nearby are 285 Baxter Neck Rd, <a href="/property/92-n-bay-rd-osterville-ma-02655/id-900001031413/">92 N Bay Rd</a>, <a href="/property/46-little-island-dr-osterville-ma-02655/id-500014544378/">46 Little Island Dr</a>, 71 Sand Point, 315 Baxter Neck Rd, <a href="/property/osterville-ma-02655/id-500014545559/">191 Sea View Ave</a>, <a href="/property/821-old-post-rd-cotuit-ma-02635/id-500014473787/">821 Old Post Rd</a>, and <a href="/property/315-baxters-neck-rd-marstons-mills-ma-02648/id-500014538293/">315 Baxters Neck Rd</a>.

$2,950,000Est. Payment
4 Beds | 4 Baths | 4,480 Sqft

Osterville, MA 02655

House For Sale

Stunning water, marsh and sunset views prevail from every room in this sophisticated, updated and meticulously maintained home set on a quiet street on Little Island. The thoughtful floor plan offers both elegant entertaining and comfortable relaxing rooms along with privately situated bedroom suites. Every space in the home is designed to maximize the enchanting and ever changing views. The expansive west facing deck with wet bar runs the length of the house, and provides multiple areas for entertaining, relaxing and enjoying the wildlife in this peaceful and private enclave. A two car attached garage, beautifully manicured landscaping with flowering shrubs and plants compliment the stone walls and walk ways around the grounds. Completed with deeded access to West Bay, and within minutes to Osterville Village, Marinas and Clubs.

$2,500,000
$19,500,000Est. Payment
9 Beds | 7 Baths | 3,315 Sqft

Osterville, MA 02655

House For Sale

Imagine the splendor of a life lived as a steward of the harbor. This timeless family estate on Little Island in Osterville is set on nearly 4 acres with 2 deep water docks & a private beach. The main residence hosts 6 bedrooms complimented with a separate 2 bedroom guest house, studio apartment & fully applianced boat house. From the properties vantage point, at the head of the inlet, watch as boats of varying shapes and sizes parade in & out of West Bay. The current stewards of this estate have welcomed many seafarers to their docks to tie up while they awaited the rise of the drawbridge into North Bay. They have shared refreshments at their refurbished antique shanty/boathouse & on their private sandy beach. The 4 distinctive dwellings set on 2 seperate lots (198 and 227) have provided the platform for many get togethers, both formal & informal, but more often than not have been the backdrop to the quiet serenity & immeasurable beauty this unique waterfront oasis has to offer.

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