289 E Bay Rd, Osterville, MA 02655
OFF MARKET

289 E Bay Rd
Osterville, MA 02655

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

$4,877,600

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $26,911/mo*
Refinance Your Home

$4,877,600

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $26,911/mo*
Refinance Your Home
4 Beds
4.5 Baths
4,100 sqft
(on 1.34 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 289 E Bay Rd

DatePriceEventSource
02/26/2021$3,035,000Sold
CCIMLS #22006776
02/11/2021$3,495,000PendingMLS PIN #72746998
01/27/2021$3,495,000ContingentCCIMLS #22006776
01/13/2021$3,495,000PriceChange
CCIMLS #22006776
11/23/2020$3,790,000PriceChange
Agent Provided
10/06/2020$3,950,000Listed For SaleAgent Provided
12/11/2014$2,749,000ListingRemovedAgent Provided
10/07/2014$2,749,000PriceChange
Agent Provided
05/20/2014$2,950,000PriceChange
Agent Provided
03/22/2014$3,295,000PriceChange
Agent Provided
03/07/2014$3,595,000Listed For SaleAgent Provided
01/08/2014$3,595,000ListingRemovedAgent Provided
12/10/2013$3,595,000PriceChange
Agent Provided
10/09/2013$3,950,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$29,995
Assessment$3,707,700
Home facts updated by county records

Comparable Sales for 289 E Bay Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
281 Wianno Avenue, Osterville, MA
0.25
Single-Family Home
$4,200,000
08/08/25
7
5.5
4,375
281 Wianno Ave, Barnstable, MA
0.31
Single-Family Home
$4,200,000
08/08/25
7
5.5
4,375
125 Wianno Circle, Osterville, MA
0.45
Single-Family Home
$3,200,000
05/14/26
4
4.5
2,752
25 Blanid Rd, Barnstable, MA
0.54
Single-Family Home
$2,425,000
05/28/25
4
2.5
2,573
25 Blanid Road, Osterville, MA
0.54
Single-Family Home
$2,425,000
05/28/25
4
2.5
2,573
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
320 Parker Road, Osterville, MA
0.71
Single-Family Home
$3,375,000
07/15/25
5
5.5
5,421
320 Parker Rd, Barnstable, MA
0.71
Single-Family Home
$3,375,000
07/15/25
5
5.5
5,421
64 Bay St, Barnstable, MA
1.02
Single-Family Home
$2,550,000
12/04/25
4
5
2,812

Assigned Schools

These are the assigned schools for 289 E Bay 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

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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Homes for sale near 289 E Bay Rd

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Off Market Homes Near 289 E Bay Rd

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289 E Bay Rd, Osterville, MA 02655 is a 4 bedroom, 5 bathroom, 4,100 sqft single-family home built in 1979. 289 E Bay Rd is located in Osterville, Osterville. This property is not currently available for sale. 289 E Bay Rd was last sold on Feb 26, 2021 for $3,035,000. The current Trulia Estimate for 289 E Bay Rd is $4,877,600.