421 Main St, Osterville, MA 02655
OFF MARKET

$16,814,700

Trulia Estimate
  • 9 Beds
  • 10 Baths
  • 11,578 sqft (on 5.46 acres)

421 Main St, Osterville, MA 02655

Osterville
Est. Refi. Payment $94,178/mo*
Refinance Your Home
Currently Off Market - Sold Aug 19, 2019 for $9,950,000

Home Value

Trulia Estimate
$16.8M
Since last month
Decreased$116K (-0.7%)
Since last year
Increased$1M (+7%)
Since last sale
Increased$7M (+68%)
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 +159% in the last 10 years
MonthEstimated value
2026
August 2026$16.72M
July 2026$16.83M
June 2026$16.79M
May 2026$16.24M
April 2026$15.89M
March 2026$15.19M
February 2026$15.09M
January 2026$14.98M
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
44 Seapuit Road, Osterville, MA
1.12
Single-Family Home
$4,650,000
05/28/26
7
8
8,345
391 Sea View Ave, Barnstable, MA
1.29
Single-Family Home
$10,500,000
12/16/25
6
5.5
6,830
391 Sea View Avenue, Osterville, MA
1.29
Single-Family Home
$10,500,000
12/16/25
6
5.5
6,830
255 Bayberry Way, Barnstable, MA
1.59
Single-Family Home
$7,800,000
07/29/26
7
6
4,896
255 Bayberry Way, Osterville, MA
1.61
Single-Family Home
$7,800,000
07/29/26
7
6
4,896
195 Bunker Hill Road, Osterville, MA
1.39
Single-Family Home
$5,600,000
09/02/25
6
7.5
6,565
195 Bunker Hill Rd, Barnstable, MA
1.39
Single-Family Home
$5,600,000
09/02/25
6
7.5
6,565
268 Parker Rd, Barnstable, MA
0.88
Single-Family Home
$3,995,000
06/01/26
5
4.5
6,239
162 Starboard Lane, Osterville, MA
0.72
Single-Family Home
$2,210,000
10/08/25
4
3.5
3,510
268 Parker Road, Osterville, MA
0.89
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
177 Bayview Circle, Osterville, MA 02655
0.09
$839,900
3
2.5
2,100
For Sale
26 Evans St, Barnstable, MA 02630
0.15
-
3
2
1,510
Off Market
38 Evans St, Barnstable, MA 02630
0.17
-
4
3.5
2,982
Off Market
48 Bayview Circle, Osterville, MA 02655
0.17
$1,168,500
3
2.5
1,775
Recently Sold
48 Bayview Cir, Barnstable, MA 02630
0.17
$1,168,500
3
2.5
1,775
Recently Sold
38 Evans Street, Osterville, MA 02655
0.17
$1,495,700
4
3.5
2,982
Off Market
53 Spice Lane, Osterville, MA 02655
0.18
$1,305,000
3
1.5
1,740
Recently Sold
53 Spice Ln, Barnstable, MA 02630
0.19
$1,305,000
3
1.5
1,740
Recently Sold
58 Evans Street, Osterville, MA 02655
0.20
$1,627,500
3
4
3,060
Off Market
52 David St, Barnstable, MA 02630
0.22
-
3
2.5
2,534
Off Market
107 Spice Lane, Osterville, MA 02655
0.28
$1,389,300
3
2.5
2,268
Off Market
107 Spice Ln, Barnstable, MA 02630
0.29
-
3
2.5
2,268
Off Market

Local Information

  • Map ViewExplore the area around 421 Main St.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1928
Lot Size
5.46 acres
Living Area
11,578 sqft
Price/Sqft
$1,452

About this House

Overlooking the beautiful waters of East Bay and Nantucket Sound sits this sophisticated yet intimate waterfront estate. The current owners completely renovated the 11,578sf home from stem to stern with the highest grade materials and exceptional craftsmanship. Interior spaces are bathed in natural light with beautifully balanced living areas all oriented toward the water. You'll find a welcoming foyer with original wood floors, living and dining rooms with custom fireplaces, a spacious, well-equipped kitchen and a handsome library with hand pegged wood. Casual spaces for family and friends include a family room, sunroom and enclosed porch. The second level offers 2 master suites and 7 additional bedrooms. An expansive lawn, in-ground pool and scores of privacy trees dress the 5.46 acre site. A custom beach house enhances the private dock. The property offers a detached 5 car garage with a gorgeous 3 bedroom, 1,875sf carriage house above for guests and extended family.Information herein is not guaranteed or warranted and should be verified by any person who is looking at this property to purchase. Square footage, bedrooms and bathrooms do not include 1,875 sq ft guest cottage with three bedrooms and two full bathrooms.
421 Main St, Osterville, MA 02655 is a 9 bedroom, 11 bathroom, 11,578 sqft single-family home in Osterville, built in 1928. It last sold for $9,950,000 on Aug 19, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $16,814,700, with a rent estimate of $2,834/month.

Home Details for 421 Main St

Interior Features

Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 20
Heating & Cooling
Air Conditioning
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1928
Property Type / Style
Property Type: Single Family Home

Exterior Features

Exterior Home Features
Exterior: Shingles
Parking & Garage
Parking Spaces: 5

Lot Information

Lot Area: 5.46 acres

Price and Tax history

DateEventPrice
Aug 19, 2019
Source: CCIMLS #21607681
Sold
$9,950,000
Jul 12, 2019
Source: Agent Provided
Pending
$9,950,000
Apr 8, 2019
Source: Agent Provided
PriceChange
$9,950,000
Price decreased by 13%
Apr 6, 2018
Source: Agent Provided
PriceChange
$11,500,000
Price decreased by 17%
Mar 3, 2017
Source: Agent Provided
PriceChange
$13,900,000
Price decreased by 7%

Market trends in Barnstable

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$681K
$20.33KMoM
Sale-to-List Price
98.2%
Price per sq ft
$461
$19MoM
Available listings
346
20MoM

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 421 Main St

  • What is 421 Main St estimated to be worth?
    Trulia's estimated value for 421 Main St in Osterville, MA is $16,814,700.
  • What is the price history for 421 Main St?
    421 Main St in Osterville, MA last sold for $9,950,000 in August 2019.
  • Is Osterville a buyer's or seller's market?
    Osterville is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Osterville?
    The median sale price in Osterville is $681K. That is down $20.33K from the prior month.
  • How big is the lot at 421 Main St?
    The lot at 421 Main St in Osterville, MA is about 5.5 acres.
  • Does 421 Main St have parking?
    Yes, 421 Main St in Osterville, MA has on-site parking.

Explore by feature - Pet Friendly

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Explore by feature - Pool

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Off Market Homes Near 421 Main St

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