27 Winfield Way
Description
- Listed by: Jonathan A Matel • William Raveis Real Estate & Home Services
Recent comparable sales
Median sold price
$3,375,000
Avg days on market
91
Sale-to-list ratio
91.6%
Osterville, MA
9 comparable properties found
$3,375,000
Sold 07/15/25
- 5
- Bedrooms
- 6
- Bathrooms
- 5,421
- Square Feet
- 0.53
- Acres
$3,400,000
Sold 10/03/25
- 4
- Bedrooms
- 5
- Bathrooms
- 5,460
- Square Feet
- 1
- Acres
$2,550,000
Sold 12/04/25
- 4
- Bedrooms
- 5
- Bathrooms
- 2,812
- Square Feet
- 0.98
- Acres
$3,010,000
Sold 04/29/25
- 4
- Bedrooms
- 6
- Bathrooms
- Unavailable
- Square Feet
- 1.33
- Acres
$3,700,000
Sold 08/31/26
- 4
- Bedrooms
- 6
- Bathrooms
- 3,557
- Square Feet
- 2.94
- Acres
$3,200,000
Sold 05/14/26
- 4
- Bedrooms
- 5
- Bathrooms
- 2,752
- Square Feet
- 0.29
- Acres
$3,475,000
Sold 08/17/26
- 4
- Bedrooms
- 5
- Bathrooms
- 4,364
- Square Feet
- 0.49
- Acres
$3,900,000
Sold 09/02/26
- 4
- Bedrooms
- 5
- Bathrooms
- 4,241
- Square Feet
- 0.6
- Acres
$2,487,500
Sold 04/16/26
- 5
- Bedrooms
- 5
- Bathrooms
- 4,715
- Square Feet
- 2.03
- Acres
Location
Sold By Murphy Real Estate, Beth Talerman
$18,857 per month
30 year fixed, 7.03% Interest
$16,363
$2,495
$0
1Property Information for 27 Winfield Way
Property Details
- Taxes: $29,934 / year
- MLS Type: Single Family / Single Family Residence
- County: Barnstable County
- Village: Osterville
- Style: Cape
- Waterfront: Yes
- Waterview: Yes
- FEMA 100 Yr Flood Plain: Not Applicable
- Town: Barnstable
Building Information
- Stories: 2
- Year Built: 1995
- Lot Size: 1.59 AC / 69,260 SF
Summary
- Directions to Property: Main Street Osterville to West Bay Road and left onto Eel River, take right at #55 Eel River Rd (also #27 Winfield Lane).
- Title Reference - Book: 10483
- Convenient To:Golf Course: Yes
- Convenient To:Marina: Yes
- Convenient To:Public Tennis: Yes
- Convenient To:Shopping: Yes
- Region: Mid-Cape
- County: Barnstable
- City Postal ID: 02655
- Street Number: 27
- MLSAreaMajor: Barnstable
- Garage: Yes
- Garage Description:Direct Entry: Yes
- Garage Description:Door Opener: Yes
- Parking Description:Stone/Gravel: Yes
- Carport: No
- Garage Spaces: 3.00
- Tax Year: 2009
- Annual Assoc Fee: $0
- Annual Taxes: $29,934
- Virtual Tour YN: No
Property
- Zoning: res
- Tax ID: 116-100-0-0
- Lot Size Source: Assessor
- Land Court Cert #: 0
- TopographyLot Desc:View: Yes
- TopographyLot Desc:Level: Yes
- Water Access:Salt: Yes
- Water Access:Other - See Remarks: Yes
- Land Use: 101 - Residential, single family
- Lot Size Square Feet: 69260
- Sqft Total: 5627
- Lot Size Units: Acres
- Living Area: 5627.0
- Total Assessment: $3,647,600
- Land Assessments: $1,761,400
- Building Assessments: $1,886,200
- Warranty Available: No
- Flood Ins Required: Not Verified
- Lead Base Paint: No
- Asbestos: Unknown
- Year Round: Yes
- Underground Fuel Tank: Unknown
- Landlord Pays:Sewer: Private Sewerage
- Year Built Desc:Approximate: Yes
- Property Type: Residential, Single Family Residence
- Property Subtypes: Single Family Residence
- Year Built Numeric: 1995
- Construction Materials: Shingle
- Property Type: Residential
- Property Attached: No
- Senior Community: No
- Cooling: Central Air
- Fuel Type:Natural Gas: Yes
- Hot Water Source:Natural Gas: Yes
- Water:Town Water: Yes
- Water Source: Town Water
Interior and Exterior Features
- Exterior Features: Underground Sprinkler, Yard
- Miles to Beach: 0 - .1
- Private Dock: No
- Beach Ownership:Private: Yes
- Foundation: Block
- Roof Description: Wood, Pitched, Shingle
- Siding Description:Shingle: Yes
- Waterfront Desc: Salt, Other - See Remarks
- Private Pool YN: No
- Security Features: Security System
- Patio And Porch Features: Patio, Covered
- Floors: Wood, Tile, Carpet
- Heating: Natural Gas
- Interior Features: Den, Exercise Room, Sun Room, Central Vacuum, Wetbar
- Basement: No
- Fireplace: Yes
- Baths Total: 6
- Baths Full: 5
- Baths Half: 1
- Bedrooms Total: 4
- Total Floor Plans Count: 0
- Bathrooms Total (Decimal): 5.50
- Bathrooms Total (Notational): 5.10
- Cooling: Yes
- Fireplaces Total: 1
- Heating: Yes
- Stories: 2
- Laundry Features: First Floor
- Kitchen Appliances: Range, Oven, Dishwasher, Disposal, Refrigerator
- General Property Info:Stories: 2
- Master Bedroom: Yes
- Master Bedroom Level: First Floor
Property History for 27 Winfield Way
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| May 14, 2010 | Sold Cape Cod & Islands Multiple Listing Service #20905685 | $3,065,000 | — |
| May 14, 2010 | Sold MLS PIN #70949852 | $3,065,000 | — |
| Apr 28, 2010 | Under Agreement Cape Cod & Islands Multiple Listing Service #20905685 | — | |
| Mar 29, 2010 | Under Agreement MLS PIN #70949852 | — | |
| Mar 29, 2010 | Contingent MLS PIN #70949852 | — | |
| Jul 20, 2009 | Listed (Active) MLS PIN #70949852 | $4,900,000 | — |
| Jun 30, 2009 | Listed (Active) Cape Cod & Islands Multiple Listing Service #20905685 | $4,900,000 | — |
| Nov 15, 1996 | Sold Cape Cod & Islands Multiple Listing Service #5012652 | $1,600,000 | — |
| Oct 21, 1996 | Under Agreement Cape Cod & Islands Multiple Listing Service #5012652 | — | |
| Oct 16, 1995 | Listed (Active) Cape Cod & Islands Multiple Listing Service #5012652 | $2,500,000 | — |
| Jul 29, 1994 | Sold Cape Cod & Islands Multiple Listing Service #16720 | $859,000 | — |
| Jul 5, 1994 | Under Agreement Cape Cod & Islands Multiple Listing Service #16720 | — | |
| Oct 19, 1991 | Listed (Active) Cape Cod & Islands Multiple Listing Service #16720 | $995,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 05/14/2010 | Sold Cape Cod & Islands Multiple Listing Service #20905685 | $3,065,000 |
| 05/14/2010 | Sold MLS PIN #70949852 | $3,065,000 |
| 04/28/2010 | Under Agreement Cape Cod & Islands Multiple Listing Service #20905685 | — |
| 03/29/2010 | Under Agreement MLS PIN #70949852 | — |
| 03/29/2010 | Contingent MLS PIN #70949852 | — |
| 07/20/2009 | Listed (Active) MLS PIN #70949852 | $4,900,000 |
| 06/30/2009 | Listed (Active) Cape Cod & Islands Multiple Listing Service #20905685 | $4,900,000 |
| 11/15/1996 | Sold Cape Cod & Islands Multiple Listing Service #5012652 | $1,600,000 |
| 10/21/1996 | Under Agreement Cape Cod & Islands Multiple Listing Service #5012652 | — |
| 10/16/1995 | Listed (Active) Cape Cod & Islands Multiple Listing Service #5012652 | $2,500,000 |
| 07/29/1994 | Sold Cape Cod & Islands Multiple Listing Service #16720 | $859,000 |
| 07/05/1994 | Under Agreement Cape Cod & Islands Multiple Listing Service #16720 | — |
| 10/19/1991 | Listed (Active) Cape Cod & Islands Multiple Listing Service #16720 | $995,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Schools near 27 Winfield Way
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | K to 3 | |||
| Public - | 4 to 5 | |||
| Public - | 6 to 7 | |||
| Public - | 8 to 12 |
Rating | School | Distance |
|---|---|---|
West Villages Elementary School PublicK to 3 | ||
Barnstable United Elementary School Public4 to 5 | ||
Barnstable Intermediate School Public6 to 7 | ||
Barnstable High School Public8 to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
Similar Homes
New listings in 02655
Nearby home values
| Address | Sold price | Beds | Baths | Sqft | Lot (Sqft) |
|---|---|---|---|---|---|
This home: 27 Winfield Way, Osterville, MA 02655 | $3,065,000 | 4 | 6 | 5,627 | 69,260 |
$1,200,000 | 3 | 3 | 2,817 | 30,056 | |
$3,065,000 | 4 | 5.5 | 9,249 | 69,260 | |
$1,200,000 | 4 | 5 | 3,027 | 25,265 | |
$3,400,000 | 6 | 5 | 5,603 | 77,537 | |
– | – | – | – | 14,375 | |
$1,150,000 | 4 | 3 | 2,810 | – | |
$2,400,000 | 3 | 3 | 3,365 | 151,153 | |
$1 | 7 | 8 | 3,583 | 27,007 | |
$1,861,000 | 4 | 2 | 4,058 | – | |
$1,800,000 | 3 | 3 | 2,500 | 36,590 | |
$1,025,000 | 4 | 3 | 1,750 | 24,829 | |
$2,500,000 | 5 | 8 | 6,685 | 88,427 | |
$2,050,000 | 3 | 4 | 2,834 | 40,946 |
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.
Listing Courtesy of William Raveis Real Estate & Home Services, Jonathan A Matel
All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than Compass includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. Neither the listing firm nor Compass and its related brokerages shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. The Broker providing this data believes it to be correct but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.
