OFF MARKET

Off Market May 2016 for $875K

$2,507,681

Est. refi paymentEst. refi $3,196/mo

•

3,745

sq ft

86 Leonard Dr, Osterville, MA 02655

About this home

Wianno Opportunity!! Deeded rights to Eel River. Fantastic corner lot close to Sea View Ave. This classic Cape Cod home is situated in the heart of Wianno on a private and lushly landscaped acre of land. A mahogany deck, stretching along the back of the house, beautiful plantings and an in ground pool highlight the outdoor living space. Interior space includes two options for first floor Master Bedroom suites, , hardwood floors throughout and a spacious family room. New addition and two car garage added to the original house in 1991. This is a rare opportunity to purchase an exceptional Osterville village home. Spectacular yard and pool!

Single-familyProperty Type

1965Year Built

1.13 acresLot Size

$670Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Gene Orloff • Sotheby's International Realty

Bought with Gene Orloff • Sotheby's International Realty

Redfin checked: 2 minutes ago

•Source:MLS PIN #71940976

Redfin Estimate

$2,507,681

$1.6M since sold in May 2016$27K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 11.7% higher than the average sale price ($2.24M) of 6 comparable homes.

SOLD JUL 21, 2026
$2,800,000
A
3 beds3.5 baths2,676 sq ft
106 Hathaway Rd, Osterville, MA 02655
SOLD AUG 11, 2026
$1,650,000
B
4 beds4.5 baths3,957 sq ft
442 Bay Ln, Centerville, MA 02632
SOLD MAY 14, 2026
$2,700,000
C
3 beds3 baths3,055 sq ft
18 Winfield Way, Osterville, MA 02655
SOLD AUG 17, 2026
$3,475,000
D
4 beds4 baths4,364 sq ft
82 Crystal Lake Rd, Osterville, MA 02655
SOLD JUL 29, 2026
$1,495,000
E
4 beds4 baths2,509 sq ft
25 Manor Way, Osterville, MA 02655
SOLD MAY 8, 2026
$1,349,000
F
4 beds2.5 baths2,326 sq ft
77 Robbins St, Osterville, MA 02655

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Earn from this home

Sell

$1,837,400

Est. take-home

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Refinance

Est. cash available

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Rent

$4,374/mo

Redfin rental estimate

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Market trends in 02655, MA

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

96.4%

0.0% MoM

Median sale price

$1.5M

$321K MoM

Avg. days on market

19d

10 days MoM

Recently sold homes

1 MoM

New listings for sale

NEW 4 HRS AGO
$990,000
3 beds2.5 baths2,116 sq ft
82 Falling Leaf Ln, Osterville, MA 02655
$1,485,000
3 beds2.5 baths1,844 sq ft
23-27 Swift Ave, Osterville, MA 02655
$999,000
2 beds2.5 baths1,564 sq ft
16 Second #4, Osterville, MA 02655
$1,349,900
3 beds3 baths2,126 sq ft
30 Deerfield Rd, Osterville, MA 02655
$999,000
2 beds2.5 baths1,564 sq ft
16 Second Ave #4, Osterville, MA 02655
$799,000
3 beds2 baths1,856 sq ft
329 Swift Ave, Osterville, MA 02655
See all

Provided by Redfin

Sale history for 86 Leonard Dr

Date

Event

Price

MLS PIN #71940976

May 20, 2016

Sold

$875,000

$234/sq ft

Mar 28, 2016

Pending

—

Jan 20, 2016

Price Changed

$1,100,000

$294/sq ft

Dec 13, 2015

Listed

$1,195,000

$319/sq ft

CCIMLS #21407698

May 20, 2016

Sold

$875,000

$234/sq ft

May 9, 2016

Listing Removed

—

Mar 28, 2016

Contingent

—

Feb 3, 2016

Relisted

—

Feb 3, 2016

Listing Removed

—

Jan 19, 2016

Price Changed

$1,100,000

$294/sq ft

Sep 24, 2015

Price Changed

$1,195,000

$319/sq ft

Sep 24, 2015

Relisted

—

Sep 15, 2015

Contingent

—

Jul 28, 2015

Price Changed

$1,295,000

$346/sq ft

May 4, 2015

Price Changed

$1,395,000

$372/sq ft

Apr 22, 2015

Listed

$1,495,000

$399/sq ft

+11

Wianno Opportunity! Deeded rights to Eel River & a short distance from Sea View Ave. This classic Cape Cod home is situated in the heart of Wianno on a private and lushly landscaped acre of land. A mahogany deck, stretching along the back of the house, beautiful plantings and an in ground pool highlight the outdoor living space. Interior space includes two optons for first floor Master Bedroom suites, hardwood floors throughout and a spacious family room. New addition & two car garage was added to the original house in 1991. This is a rare opportunity to purchase an exceptional Osterville Village home. Spectacular yard and pool!

Public Records

May 1, 1991

Sold

$499,000

$133/sq ft

Public Records

Jan 5, 1987

Sold

$465,000

$124/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$13,709 (+15.5%)

$810,900 + $832,900

$1,643,800

2022

$11,871 (+4.5%)

$530,700 + $700,700

$1,231,400

2021

$11,364 (−1.7%)

$482,400 + $600,900

$1,083,300

2020

$11,556 (−0.6%)

$518,400 + $536,000

$1,054,400

2019

$11,626 (+11.1%)

$544,300 + $486,400

$1,030,700

2018

$10,463 (−13.0%)

$518,400 + $414,100

$932,500

2017

$12,029 (−1.7%)

$695,700 + $422,200

$1,117,900

2016

$12,240 (−16.8%)

$700,700 + $422,200

$1,122,900

2015

$14,704

$934,300 + $420,900

$1,355,200

Tax history for 86 Leonard Dr

Year

Property tax

Land + Additions

Assessment*

2023

$13,709 (+15.5%)

$810,900 + $832,900

$1,643,800

2022

$11,871 (+4.5%)

$530,700 + $700,700

$1,231,400

2021

$11,364 (−1.7%)

$482,400 + $600,900

$1,083,300

2020

$11,556 (−0.6%)

$518,400 + $536,000

$1,054,400

2019

$11,626 (+11.1%)

$544,300 + $486,400

$1,030,700

2018

$10,463 (−13.0%)

$518,400 + $414,100

$932,500

2017

$12,029 (−1.7%)

$695,700 + $422,200

$1,117,900

2016

$12,240 (−16.8%)

$700,700 + $422,200

$1,122,900

2015

$14,704

$934,300 + $420,900

$1,355,200

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

1.13 Acres

Year renovated

—

Sq. Ft.

4,228

Year built

1965

Style

Single Family Residential

County

Barnstable County

APN

2231823

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 19, 2023.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 6
AttachedGarageYN: Yes
Parking Features: Attached, Garage Door Opener, Storage, Workshop in Garage, Garage Faces Side, Paved Drive, Off Street, Driveway, Paved

Interior

Master Bedroom Information
Level: First

Bedroom #2 Information
Level: First

Bedroom #3 Information
Level: Second

Bathroom Information
# of Bathrooms (Full): 4
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Bathroom #1 Information
Level: First

Bathroom #2 Information
Level: First

Bathroom #3 Information
Level: First

Living Room Information
Level: First

Family Room Information
Level: First

Dining Room Information
Level: First

Kitchen Information
Level: First

Basement Information
Basement: Full, Interior Entry, Concrete

Laundry Information
Laundry Features: First Floor

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 2

Interior Features
# of Rooms (Total): 8
Window Features: Screens
Flooring: Wood
Interior Features: Wet Bar

Exterior

Building Information
Building Area (Total): 3,745
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual

Exterior Features
Fencing: Fenced/Enclosed, Fenced
Roof: Shingle
Patio And Porch Features: Deck, Deck - Wood
Exterior Features: Deck, Deck - Wood, Pool - Inground, Pool - Inground Heated, Cabana, Rain Gutters, Storage, Professional Landscaping, Sprinkler System, Screens, Fenced Yard, Fruit Trees, Garden

Pool Information
Has Private Pool
Pool Features: In Ground, Pool - Inground Heated

Property Information
PropertySubType: Single Family Residence
Other Structures: Cabana

Lot Information
Lot Size (Acres): 1.13
Lot Features: Corner Lot, Wooded, Cleared, Level
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $14,246.80
Tax Year: 2015

Utilities

Utility Information
Sewer: Inspection Required for Sale, Private Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Forced Air, Natural Gas
Cooling: Central Air, Wall Unit(s)

Location

Location Information
Directions: Osterville Village to Parker Rd to Rt on Leonard
UnparsedAddress: 86 Leonard Dr, Barnstable MA 02655

Community Information
Senior CommunityYN: No
Community Features: Shopping, Pool, Golf, Medical Facility, Conservation Area, Marina, Private School, Public School, University

Public facts

Beds: 5
Baths: 3.0
Sq. Ft.: 4,228
Stories: 2.0
Lot Size: 1.13 acres
Style: Single Family Residential
Year Built: 1965
Year Renovated: —
County: Barnstable County
APN: 2231823

Home facts updated by county records on Jul 19, 2023

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

Barnstable United Elementary School

Public 4-5 • Assigned • 3.2mi

3/10

Barnstable High School

Public 8-12 • Assigned • 4.3mi

3/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

4/10 Heat Factor

7 days above 88° expected this year, 18 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Osterville, MA • 02655

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.8 hours in June and 4.5 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.38M – $2.88M

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Nearby similar homes

NEW 4 HRS AGO

$990,000

3 beds2.5 baths2,116 sq ft

82 Falling Leaf Ln, Osterville, MA 02655

3D WALKTHROUGH

$875,000

3 beds2 baths1,497 sq ft

5 Briar Patch Rd, Osterville, MA 02655

$829,900

3 beds2.5 baths2,100 sq ft

177 Bayview Cir, Osterville, MA 02655

$589,000

2 beds1 bath1,056 sq ft

30 Patience Ln, Cotuit, MA 02635

3D WALKTHROUGH

$4,950,000

5 beds7.5 baths5,970 sq ft

313 Bridge St, Osterville, MA 02655

VIDEO TOUR

$8,800,000

5 beds5 baths7,157 sq ft

25 Oyster Way, Osterville, MA 02655

New listings for sale in 02655

NEW 4 HRS AGO

$990,000

3 beds2.5 baths2,116 sq ft

82 Falling Leaf Ln, Osterville, MA 02655

$1,485,000

3 beds2.5 baths1,844 sq ft

23-27 Swift Ave, Osterville, MA 02655

$999,000

2 beds2.5 baths1,564 sq ft

16 Second #4, Osterville, MA 02655

$1,349,900

3 beds3 baths2,126 sq ft

30 Deerfield Rd, Osterville, MA 02655

$999,000

2 beds2.5 baths1,564 sq ft

16 Second Ave #4, Osterville, MA 02655

$799,000

3 beds2 baths1,856 sq ft

329 Swift Ave, Osterville, MA 02655

Home values near 86 Leonard Dr

Data from public records.

Address	Redfin Estimate
81 Leonard Rd, Osterville, MA 3 Beds \| 3.5 Baths \| 2232 Sq. Ft.	$3,075,723
63 Leonard Rd, Osterville, MA 5 Beds \| 3.5 Baths \| 3093 Sq. Ft.	$2,704,133

Address	Redfin Estimate
51 Leonard Rd, Osterville, MA 3 Beds \| 2 Baths \| 1927 Sq. Ft.	$1,856,145
38 Leonard Rd, Osterville, MA 3 Beds \| 3.5 Baths \| 4120 Sq. Ft.	$3,086,536

Address	Redfin Estimate
35 Leonard Rd, Osterville, MA 4 Beds \| 2 Baths \| 2572 Sq. Ft.	$2,014,223
54 Leonard Rd, Osterville, MA 4 Beds \| 2 Baths \| 2470 Sq. Ft.	$1,922,965

Property information provided by MLS PIN when last listed in 2015. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 02655, MA

Sale history for 86 Leonard Dr

Tax history for 86 Leonard Dr

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02655

Home values near 86 Leonard Dr

More real estate resources