86 Leonard Rd, Osterville, MA 02655
OFF MARKET

86 Leonard Rd
Osterville, MA 02655

Osterville
  • 4 Beds
  • 4.5 Baths
  • 3,745 sqft (on 1 acre)

$2,848,500

Trulia Estimate
as of Jul 6, 2026

$2,848,500

Trulia Estimate
as of Jul 6, 2026
4 Beds
4.5 Baths
3,745 sqft
(on 1 acre)

Local Information

  • Map ViewExplore the area around 86 Leonard Rd.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This classic Cape Cod home is situated in the heart of Wianno on a secluded and lushly landscaped approx. 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 a first floor master bedroom, hardwood floors throughout and a spacious family room. A private guest suite and two-car garage were added to the original house in 1991. This is a rare opportunity to purchase an exceptional Osterville village home.
86 Leonard Rd, Osterville, MA 02655 is a 4 bedroom, 5 bathroom, 3,745 sqft single-family home in Osterville, built in 1965. It last sold for $875,000 on May 20, 2016. It is currently off market. The Trulia Estimate is $2,848,500, with a rent estimate of $7,273/month.

Home Highlights

Parking
No Info
Outdoor
Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 86 Leonard Rd

Interior Features

Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
Interior Details
Number of Rooms: 9
Appliances & Utilities
Dishwasher
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodPatio
Pool
Pool

Property Information

Year Built
Year Built: 1965
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Lot Information

Lot Area: 1 acre

Price History for 86 Leonard Rd

DatePriceEventSource
05/20/2016$875,000Sold
CCIMLS #21407698
01/21/2016$1,100,000PriceChange
Agent Provided
09/26/2015$1,195,000PriceChange
Agent Provided
07/30/2015$1,295,000PriceChange
Agent Provided
05/07/2015$1,395,000PriceChange
Agent Provided
11/13/2014$1,495,000PriceChange
Agent Provided
08/17/2014$1,650,000Listed For SaleAgent Provided
05/23/1991$499,000Sold
N/A
01/05/1987$465,000Sold
N/A

Market trends in Barnstable

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$673K
$7.5KMoM
Sale-to-List Price
98.1%
0.3%MoM
Price per sq ft
$432
$14MoM
Available listings
343
21MoM
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Property Tax and Assessment

Year2025
Tax$15,774
Assessment$1,949,800
Home facts updated by county records

Comparable Sales for 86 Leonard Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
72 Hathaway Rd, Barnstable, MA
0.09
Single-Family Home
$1,600,000
10/15/25
4
3
2,050
72 Hathaway Road, Osterville, MA
0.09
Single-Family Home
$1,600,000
10/15/25
4
3
2,050
780 Sea View Avenue, Osterville, MA
0.44
Single-Family Home
$3,400,000
10/03/25
4
4
5,460
780 Sea View Ave, Barnstable, MA
0.44
Single-Family Home
$3,400,000
10/03/25
4
4
5,762
439 Sea View Avenue, Osterville, MA
0.28
Single-Family Home
$5,800,000
02/18/26
6
5
4,021
320 Parker Road, Osterville, MA
0.40
Single-Family Home
$3,375,000
07/15/25
5
5.5
5,421
320 Parker Rd, Barnstable, MA
0.41
Single-Family Home
$3,375,000
07/15/25
5
5.5
5,421
18 Winfield Lane, Osterville, MA
0.61
Single-Family Home
$2,700,000
05/14/26
3
3
3,055
545 Sea View Avenue, Osterville, MA
0.27
Single-Family Home
$10,500,000
09/16/25
6
5.5
3,859
545 Sea View Ave, Barnstable, MA
0.28
Single-Family Home
$10,500,000
09/16/25
6
5.5
3,859

Nearby homes

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Assigned Schools

These are the assigned schools for 86 Leonard Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Osterville
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Osterville

At least 22 Trulia users voted on each feature.

  • 91 % Say car is needed

  • 83 % Say parking is easy

  • 78 % Say there's wildlife

  • 76 % Say yards are well-kept

  • 73 % Say it's quiet

  • 71 % Say it's dog friendly

  • 63 % Say neighbors are friendly

  • 63 % Say there's holiday spirit

  • 59 % Say they plan to stay for at least 5 years

  • 57 % Say people would walk alone at night

  • 50 % Say kids play outside

  • 49 % Say it's walkable to restaurants

  • 40 % Say there are community events

  • 38 % Say it's walkable to grocery stores

  • 27 % Say there are sidewalks

  • 25 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Jacqueline Hicks
    "This area lacks decent public transportation. Having a car is extremely helpful. The is the bus system but it isn’t that reliable and it doesn’t have lots of stops and routes so one has to walk a distance to get to path of bus"
    0
    Flag
  • Trulia User
    "moderate traffic at regular business hours, otherwise VERY easy travel, and safe drivers on the road "
    0
    Flag
  • Purplevelvet917
    "The bus goes by only once an hour each way. A car is helpful. Summer traffic make the commute slow so allow for extra time."
    1
    Flag
  • Joshtweaver
    "Very friendly upscale area with beautiful scenery. Great for a summer vacation. Very peaceful. Can get quiet at times so if you’re looking for excitement you may want to look elsewhere. "
    14
    Flag
  • Joshtweaver
    "Great area for kids to grow up or spend the summers in. Very friendly community feel. Safe to walk around in. "
    0
    Flag
  • Ashleighmaeb
    "An hour and a half drive back to Boston if your lucky. You can fly which is way more convenient but driving is the cheapest. It’s our summer home so we don’t care that much since we’re down all summer."
    2
    Flag
  • Hudson
    "I’ve lived in this neighborhood for over 3 years and love it. The neighbors are nice and there are lots of kids and young families."
    0
    Flag
  • bagleyheath
    "Ostervile, lovely place apart from the people. Rude arrogant, dont you know who I am? types where the rules of civilty only apply to others. If you are in the top 1% or aspire to be you'll love it."
    1
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

7 pet-friendly rentals in Osterville, MA

Explore by feature - Garage

8 rentals with a garage in Osterville, MA

Explore by feature - Air Conditioning

20 rentals with air conditioning in Osterville, MA

Explore by feature - Washer/dryer

31 rentals with a washer/dryer in Osterville, MA

Homes for sale near 86 Leonard Rd

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Off Market Homes Near 86 Leonard Rd

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