289 E Bay Rd, Osterville, MA 02655
Property image
Property image
OFF MARKET

289 E Bay Rd
Osterville, MA 02655

Osterville
  • 4 Beds
  • 4.5 Baths
  • 4,100 sqft (on 1.34 acres)

$4,935,300

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $27,696/mo*
Refinance Your Home

$4,935,300

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $27,696/mo*
Refinance Your Home
4 Beds
4.5 Baths
4,100 sqft
(on 1.34 acres)

Home Value

Trulia Estimate
$4.93M
Since last month
Decreased$137K (-2.7%)
Since last year
Decreased$234K (-4.5%)
Since last sale
Increased$2M (+62.6%)
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 +84% in the last 10 years
MonthEstimated value
2026
August 2026$4.94M
July 2026$4.98M
June 2026$5.07M
May 2026$4.9M
April 2026$4.84M
March 2026$4.79M
February 2026$4.58M
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
125 Wianno Circle, Osterville, MA
0.45
Single-Family Home
$3,200,000
05/14/26
4
4.5
2,752
64 Bay Street, Osterville, MA
0.94
Single-Family Home
$2,550,000
12/04/25
4
5
2,812
125 Wianno Cir, Barnstable, MA
0.45
Single-Family Home
$3,200,000
05/14/26
4
4.5
2,752
268 Parker Rd, Barnstable, MA
0.69
Single-Family Home
$3,995,000
06/01/26
5
4.5
6,239
268 Parker Road, Osterville, MA
0.70
Single-Family Home
$3,995,000
06/01/26
5
4.5
6,239
106 Hathaway Road, Osterville, MA
0.88
Single-Family Home
$2,800,000
07/21/26
3
3.5
2,676
64 Bay St, Barnstable, MA
1.02
Single-Family Home
$2,550,000
12/04/25
4
5
2,812
92 Wianno Circle, Osterville, MA
0.42
Single-Family Home
$1,490,000
05/29/26
3
3
2,459
439 Sea View Avenue, Osterville, MA
0.92
Single-Family Home
$5,800,000
02/18/26
6
5
4,021
162 Starboard Lane, Osterville, MA
1.13
Single-Family Home
$2,210,000
10/08/25
4
3.5
3,510

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
199 E Bay Rd #13, Barnstable, MA 02630
0.17
$1,726,000
3
3.5
3,551
Recently Sold
199 East Bay Road #13, Osterville, MA 02655
0.19
$1,726,000
3
3.5
3,551
Recently Sold
281 Wianno Avenue, Osterville, MA 02655
0.25
$4,213,900
7
5.5
4,375
Off Market
321 Wianno Avenue, Osterville, MA 02655
0.25
$3,278,000
5
4
3,424
Off Market
149 East Bay Road, Osterville, MA 02655
0.26
$4,396,100
4
3.5
3,100
Off Market
156 E Bay Road, Osterville, MA 02655
0.26
$3,450,000
4
5
3,924
For Sale
149 E Bay Rd, Barnstable, MA 02630
0.26
-
4
3.5
3,100
Off Market
156 E Bay Rd, Barnstable, MA 02630
0.27
$3,450,000
4
5
2,424
For Sale
204 Crystal Lake Rd, Barnstable, MA 02630
0.29
-
4
4.5
2,434
Off Market
204 Crystal Lake Road, Osterville, MA 02655
0.29
$2,734,200
4
4.5
2,434
Off Market
281 Wianno Ave, Barnstable, MA 02630
0.31
-
7
5.5
4,375
Off Market
207 Crystal Lake Rd, Barnstable, MA 02630
0.30
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 289 E Bay Rd.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1979
Lot Size
1.34 acres
Living Area
4,100 sqft
Price/Sqft
$1,204
Parking
Garage

About this House

Experience Coastal Living at its best! Breathtaking views of East Bay and Nantucket Sound from this exquisite property located on one of Osterville's most prestigious streets. Dowses Beach and the village are just steps away. One may enjoy kayaking and boating from your own private dock. A highlight of this stately colonial is its wonderful space for entertaining family and friends. It offers an expansive living room, dining room and updated eat-in kitchen. Convenient first floor living with a downstairs bed and bath option. Upstairs offers three additional en suite bedrooms. The master bedroom features a sitting room/ office space area, wet bar, walk-in closet and master bath. There are four fireplaces, hardwood floors and over sized windows throughout. The backyard features a large deck, seating area, hot tub and outdoor shower. Enjoy creating your own Cape Cod memories for generations to come, at this stunning seaside retreat. 289 East Bay property and 290 East Bay Dock are being so
289 E Bay Rd, Osterville, MA 02655 is a 4 bedroom, 5 bathroom, 4,100 sqft single-family home in Osterville, built in 1979. It last sold for $3,035,000 on Feb 26, 2021. It is currently off market. The Trulia Estimate is $4,935,300, with a rent estimate of $7,989/month.

Home Details for 289 E Bay Rd

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood
Interior Details
Number of Rooms: 10Types of Rooms: Walk In Closet, Dining Room, Laundry Room, Office, Pantry
Fireplace & Spa
FireplaceHot Tub or Spa
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Shingle Not WoodSprinkler System
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached

Property Information

Year Built
Year Built: 1979
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 1.34 acres

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Feb 26, 2021
Source: CCIMLS #22006776
Sold
$3,035,000
Feb 11, 2021
Source: MLS PIN #72746998
Pending
$3,495,000
Jan 27, 2021
Source: CCIMLS #22006776
Contingent
$3,495,000
Jan 13, 2021
Source: CCIMLS #22006776
PriceChange
$3,495,000
Price decreased by 8%
Nov 23, 2020
Source: Agent Provided
PriceChange
$3,790,000
Price decreased by 4%

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

11 pet-friendly rentals in Osterville, MA

Explore by feature - Garage

14 rentals with a garage in Osterville, MA

Explore by feature - Air Conditioning

28 rentals with air conditioning in Osterville, MA

Explore by feature - Pool

7 rentals with a pool in Osterville, MA

Explore by feature - Washer/dryer

30 rentals with a washer/dryer in Osterville, MA

Homes for sale near 289 E Bay Rd

Skip to last item
Skip to first item

Off Market Homes Near 289 E Bay Rd

Skip to last item
Skip to first item

Frequently asked questions about 289 E Bay Rd

  • What is 289 E Bay Rd estimated to be worth?
    Trulia's estimated value for 289 E Bay Rd in Osterville, MA is $4,935,300.
  • What is the price history for 289 E Bay Rd?
    289 E Bay Rd in Osterville, MA last sold for $3,035,000 in February 2021.
  • 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 289 E Bay Rd have air conditioning?
    Yes, 289 E Bay Rd in Osterville, MA has air conditioning.
  • Does 289 E Bay Rd have laundry facilities?
    Yes, 289 E Bay Rd in Osterville, MA has laundry facilities.