149 East Bay Road, Osterville, MA 02655
Property image
Property image
OFF MARKET

149 East Bay Road
Osterville, MA 02655

Osterville
  • 4 Beds
  • 3.5 Baths
  • 3,100 sqft (on 0.96 acres)

$4,396,100

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $24,724/mo*
Refinance Your Home

$4,396,100

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $24,724/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,100 sqft
(on 0.96 acres)

Home Value

Trulia Estimate
$4.4M
Since last month
Increased$19K (+0.4%)
Since last year
Decreased$306K (-6.4%)
Since last sale
Decreased$135K (-2.9%)
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 +208% in the last 10 years
MonthEstimated value
2026
August 2026$4.44M
July 2026$4.42M
June 2026$4.47M
May 2026$4.41M
April 2026$4.31M
March 2026$4.28M
February 2026$4.34M
January 2026$4.53M
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
82 Crystal Lake Road, Osterville, MA
0.29
Single-Family Home
$3,475,000
08/17/26
4
4
4,364
125 Wianno Circle, Osterville, MA
0.27
Single-Family Home
$3,200,000
05/14/26
4
4.5
2,752
64 Bay Street, Osterville, MA
0.69
Single-Family Home
$2,550,000
12/04/25
4
5
2,812
268 Parker Rd, Barnstable, MA
0.48
Single-Family Home
$3,995,000
06/01/26
5
4.5
6,239
64 Bay St, Barnstable, MA
0.76
Single-Family Home
$2,550,000
12/04/25
4
5
2,812
18 Winfield Lane, Osterville, MA
0.76
Single-Family Home
$2,700,000
05/14/26
3
3
3,055
268 Parker Road, Osterville, MA
0.49
Single-Family Home
$3,995,000
06/01/26
5
4.5
6,239
146 Scudder Road, Osterville, MA
0.34
Single-Family Home
$2,500,000
08/12/26
3
4
2,650
106 Hathaway Road, Osterville, MA
0.77
Single-Family Home
$2,800,000
07/21/26
3
3.5
2,676
92 Wianno Circle, Osterville, MA
0.28
Single-Family Home
$1,490,000
05/29/26
3
3
2,459

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
149 E Bay Rd, Barnstable, MA 02630
0.00
-
4
3.5
3,100
Off Market
199 East Bay Road #13, Osterville, MA 02655
0.07
$1,726,000
3
3.5
3,551
Recently Sold
199 E Bay Rd #13, Barnstable, MA 02630
0.09
$1,726,000
3
3.5
3,551
Recently Sold
156 E Bay Road, Osterville, MA 02655
0.06
$3,450,000
4
5
3,924
For Sale
281 Wianno Avenue, Osterville, MA 02655
0.12
$4,213,900
7
5.5
4,375
Off Market
281 Wianno Ave, Barnstable, MA 02630
0.12
-
7
5.5
4,375
Off Market
321 Wianno Avenue, Osterville, MA 02655
0.15
$3,278,000
5
4
3,424
Off Market
219 Wianno Ave, Barnstable, MA 02630
0.17
-
3
2.5
2,708
Off Market
219 Wianno Avenue, Osterville, MA 02655
0.18
$3,514,700
3
2.5
2,708
Off Market
34 Hollingsworth Road, Osterville, MA 02655
0.23
$1,512,700
3
2
1,738
Off Market
125 Wianno Cir, Barnstable, MA 02630
0.27
$3,200,000
4
4.5
2,752
Recently Sold

Local Information

  • Map ViewExplore the area around 149 East Bay Road.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1958
Lot Size
0.96 acres
Living Area
3,100 sqft
Price/Sqft
$1,418
Parking
2 Car Garage

About this House

Embrace the epitome of coastal luxury in Osterville Village with this impeccably restored shingle-style residence. A striking entrance with Belgian block stonework leads to professionally landscaped grounds. The main level features an artisanal kitchen, a chic bar area, and a sumptuous primary suite with a marble bathroom. Throughout, find exquisite craftsmanship and upscale details. The sprawling backyard oasis offers privacy and tranquility. This residence is ideally situated between the village and Dowses Beach. Buyers and agents are advised to verify details.
149 East Bay Road, Osterville, MA 02655 is a 4 bedroom, 4 bathroom, 3,100 sqft single-family home in Osterville, built in 1958. It last sold for $4,572,500 on Jun 24, 2024 (7% below the $4,895,000 asking price). It is currently off market. The Trulia Estimate is $4,396,100, with a rent estimate of $6,553/month.

Home Details for 149 East Bay Road

Interior Features

Interior Details
Basement: Full,Partial,Interior EntryNumber of Rooms: 8
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3100 Square Feet
Appliances & Utilities
Appliances: Gas Water Heater
Heating & Cooling
Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Flooring: Hardwood, Tile
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood, Tile

Exterior Features

Exterior Home Features
Roof: Shingle WoodExterior: Private Yard, Underground SprinklerFoundation: Block, PouredNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Attached
Frontage
Road Frontage: PublicRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Cumulative Days on Market: 30

Property Information

Year Built
Year Built: 1958Year Renovated: 2022
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Shingle SidingNot a New ConstructionNot Attached PropertyDoes Not Include Home Warranty
Property Information
Condition: Updated/Remodeled, ApproximateParcel Number: 140159

Price & Status

Price
List Price: $4,895,000

Active Status

MLS Status: Closed

Location

Direction & Address
City: Osterville
School Information
Elementary School District: BarnstableJr High / Middle School District: BarnstableHigh School District: Barnstable

Building

Building Area
Building Area: 3100 Square Feet

HOA

No HOA

Lot Information

Lot Area: 0.96 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Conventional

Miscellaneous

BasementMls Number: 22401542Showing Requirements: Appointment Required, Call Listing Agent
Last check for updates: about 8 hours ago
Listed by Ellen Valentgas, (508) 648-5086
Sotheby's International Realty
Bought with: Rick Shechtman, (508) 364-5200, Kinlin Grover Compass
Source: CCIMLS, MLS#22401542

Price and Tax history

DateEventPrice
Jun 24, 2024
Source: CCIMLS #22401542
Sold
$4,572,500
May 16, 2024
Source: CCIMLS #22401542
Pending
$4,895,000
Apr 16, 2024
Source: CCIMLS #22401542
Listed For Sale
$4,895,000
Sep 1, 2023
Source: CCIMLS #22300514
ListingRemoved
$5,195,000
Jun 30, 2023
Source: CCIMLS #22300514
PriceChange
$5,195,000
Price decreased by 5%

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
Skip to last item
  • Results are loading
Skip to first item

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

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

12 pet-friendly rentals in Osterville, MA

Explore by feature - Garage

8 rentals with a garage in Osterville, MA

Explore by feature - Air Conditioning

26 rentals with air conditioning in Osterville, MA

Explore by feature - Pool

7 rentals with a pool in Osterville, MA

Explore by feature - Washer/dryer

33 rentals with a washer/dryer in Osterville, MA

Homes for sale near 149 East Bay Road

Skip to last item
Skip to first item

Off Market Homes Near 149 East Bay Road

Skip to last item
Skip to first item

Frequently asked questions about 149 East Bay Road

  • What is 149 East Bay Road estimated to be worth?
    Trulia's estimated value for 149 East Bay Road in Osterville, MA is $4,396,100.
  • What is the price history for 149 East Bay Road?
    149 East Bay Road in Osterville, MA last sold for $4,572,500 in June 2024.
  • 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.
  • Does 149 East Bay Road have air conditioning?
    Yes, 149 East Bay Road in Osterville, MA has air conditioning.
  • Does 149 East Bay Road have a yard?
    Yes, 149 East Bay Road in Osterville, MA has a yard.
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 CC&I Assoc. of REALTORS®, Inc. includes the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS®, Inc. shall be responsible for any typographical errors, misinformation, 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. This site was last updated 2022-04-05 08:58:10 PDT. All properties are subject to prior sale, changes, or withdrawal. Copyright 2022© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.