86 Leonard Rd, Osterville, MA 02655
OFF MARKET

$3,019,200

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

86 Leonard Rd, Osterville, MA 02655

Osterville
Est. Refi. Payment $17,663/mo*
Refinance Your Home
Currently Off Market - Sold May 20, 2016 for $875,000

Home Value

Trulia Estimate
$3.02M
Since last month
Increased$119K (+4.2%)
Since last year
Increased$329K (+12.5%)
Since last sale
Increased$2M (+238.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +236% in the last 10 years
MonthEstimated value
2026
September 2026$2.96M
August 2026$2.96M
July 2026$2.84M
June 2026$2.84M
May 2026$2.73M
April 2026$2.67M
March 2026$2.69M
February 2026$2.6M
January 2026$2.48M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
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 Rd Road, Osterville, MA
0.09
Single-Family Home
$1,600,000
10/15/25
4
3
2,050
106 Hathaway Road, Osterville, MA
0.09
Single-Family Home
$2,800,000
07/21/26
3
3.5
2,676
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
567 Sea View Avenue, Osterville, MA
0.18
Single-Family Home
$2,950,000
03/26/26
7
4
4,328
18 Winfield Lane, Osterville, MA
0.61
Single-Family Home
$2,700,000
05/14/26
3
3
3,055
82 Crystal Lake Road, Osterville, MA
0.60
Single-Family Home
$3,475,000
08/17/26
4
4
4,364
268 Parker Road, Osterville, MA
0.51
Single-Family Home
$3,995,000
06/01/26
5
4.5
6,239

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
86 Leonard Drive, Osterville, MA 02655
0.01
$5,140,500
4
4.5
3,745
Off Market
81 Leonard Drive, Osterville, MA 02655
0.05
$3,369,700
3
3.5
2,232
Off Market
70 Leonard Drive, Osterville, MA 02655
0.03
$3,562,100
4
4
2,821
Off Market
106 Hathaway Road, Osterville, MA 02655
0.09
$2,800,000
3
3.5
2,676
Recently Sold
72 Hathaway Rd, Barnstable, MA 02630
0.09
-
4
3
2,050
Off Market
72 Hathaway Rd Road, Osterville, MA 02655
0.09
$2,700,000
4
3
2,050
For Sale
567 Sea View Avenue, Osterville, MA 02655
0.18
$2,950,000
7
4
4,328
Recently Sold
434 Eel River Road, Osterville, MA 02655
0.15
$3,000,000
4
3.5
2,210
Recently Sold
501 Eel River Road, Osterville, MA 02655
0.21
$9,950,000
6
8
8,203
For Sale
439 Sea View Avenue, Osterville, MA 02655
0.28
$5,800,000
6
5
4,021
Recently Sold
545 Sea View Avenue, Osterville, MA 02655
0.27
$10,723,000
6
5.5
3,859
Off Market
545 Sea View Ave, Barnstable, MA 02630
0.28
-
6
5.5
3,859
Off Market

Local Information

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

Home Highlights

Single-Family Home
Built in 1965
1 acre lot
3,745 sqft
$806/sqft

About this House

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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,019,200.

Home Details for 86 Leonard Rd

Interior Features

Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
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 and Tax history

DateEventPrice
May 20, 2016
Source: CCIMLS #21407698
Sold
$875,000
Jan 21, 2016
Source: Agent Provided
PriceChange
$1,100,000
Price decreased by 8%
Sep 26, 2015
Source: Agent Provided
PriceChange
$1,195,000
Price decreased by 8%
Jul 30, 2015
Source: Agent Provided
PriceChange
$1,295,000
Price decreased by 7%
May 7, 2015
Source: Agent Provided
PriceChange
$1,395,000
Price decreased by 7%

Market trends in Barnstable

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$682K
$3.33KMoM
Sale-to-List Price
98.5%
0.3%MoM
Price per sq ft
$464
$3MoM
Available listings
309
37MoM

Around this home

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

LGBTQ Local Legal Protections

Frequently asked questions about 86 Leonard Rd

  • What is 86 Leonard Rd estimated to be worth?
    Trulia's estimated value for 86 Leonard Rd in Osterville, MA is $3,019,200.
  • What is the price history for 86 Leonard Rd?
    86 Leonard Rd in Osterville, MA last sold for $875,000 in May 2016.
  • Is Osterville a buyer's or seller's market?
    Osterville is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Osterville?
    The median sale price in Osterville is $682K. That is down $3.33K from the prior month.
  • Does 86 Leonard Rd have a pool?
    Yes, 86 Leonard Rd in Osterville, MA has a pool.
  • How big is the lot at 86 Leonard Rd?
    The lot at 86 Leonard Rd in Osterville, MA is about 1 acre.

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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Apartments for Rent

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Off Market Homes Near 86 Leonard Rd

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