99 E Bay Rd, Osterville, MA 02655
OFF MARKET

99 E Bay Rd
Osterville, MA 02655

Osterville
  • 5 Beds
  • 4.5 Baths
  • 3,228 sqft (on 0.84 acres)

$3,086,900

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $17,400/mo*
Refinance Your Home

$3,086,900

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $17,400/mo*
Refinance Your Home
5 Beds
4.5 Baths
3,228 sqft
(on 0.84 acres)

Home Value

Trulia Estimate
$3.09M
Since last month
Decreased$79K (-2.5%)
Since last year
Increased$58K (+1.9%)
Since last sale
Increased$2M (+111.8%)
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 +98% in the last 10 years
MonthEstimated value
2026
August 2026$3.07M
July 2026$3.11M
June 2026$3.15M
May 2026$3.07M
April 2026$3.06M
March 2026$2.97M
February 2026$2.86M
January 2026$2.8M
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
77 Robbins Street, Osterville, MA
0.39
Single-Family Home
$1,349,000
05/08/26
4
2.5
2,976
64 Bay Street, Osterville, MA
0.58
Single-Family Home
$2,550,000
12/04/25
4
5
2,812
92 Wianno Circle, Osterville, MA
0.30
Single-Family Home
$1,490,000
05/29/26
3
3
2,459
125 Wianno Circle, Osterville, MA
0.27
Single-Family Home
$3,200,000
05/14/26
4
4.5
2,752
120 Robbins Street, Osterville, MA
0.47
Single-Family Home
$1,220,000
09/03/25
3
3.5
3,226
120 Robbins St, Barnstable, MA
0.48
Single-Family Home
$1,220,000
09/03/25
3
3.5
2,976
64 Bay St, Barnstable, MA
0.66
Single-Family Home
$2,550,000
12/04/25
4
5
2,812
92 Wianno Cir, Barnstable, MA
0.30
Single-Family Home
$1,490,000
05/29/26
3
2
2,459
268 Parker Rd, Barnstable, MA
0.44
Single-Family Home
$3,995,000
06/01/26
5
4.5
6,239
146 Scudder Road, Osterville, MA
0.30
Single-Family Home
$2,500,000
08/12/26
3
4
2,650

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
0.10
-
4
3.5
3,100
Off Market
219 Wianno Ave, Barnstable, MA 02630
0.12
-
3
2.5
2,708
Off Market
149 East Bay Road, Osterville, MA 02655
0.10
$4,396,100
4
3.5
3,100
Off Market
219 Wianno Avenue, Osterville, MA 02655
0.14
$3,514,700
3
2.5
2,708
Off Market
156 E Bay Road, Osterville, MA 02655
0.11
$3,450,000
4
5
3,924
For Sale
281 Wianno Ave, Barnstable, MA 02630
0.16
-
7
5.5
4,375
Off Market
34 Hollingsworth Road, Osterville, MA 02655
0.16
$1,512,700
3
2
1,738
Off Market
199 East Bay Road #13, Osterville, MA 02655
0.18
$1,726,000
3
3.5
3,551
Recently Sold
141 Wianno Avenue, Osterville, MA 02655
0.18
$2,152,900
4
4.5
4,000
Off Market
141 Wianno Avenue, Osterville, MA 02655
0.18
$2,929,600
4
3.5
3,908
Off Market
281 Wianno Avenue, Osterville, MA 02655
0.20
$4,213,900
7
5.5
4,375
Off Market
19 E Bay Road, Osterville, MA 02655
0.17
$1,506,300
3
2.5
1,471
Off Market

Local Information

  • Map ViewExplore the area around 99 E Bay Rd.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1973
Lot Size
0.84 acres
Living Area
3,228 sqft
Price/Sqft
$956
Parking
Garage

About this House

Around the corner from Dowses Beach, youll find this interesting U-shaped ranch; 3 bedrooms, including the Master on one side, and 2 guest bedrooms on the other side. Formal living room, kitchen with breakfast nook, and family room. Hardwood floors, gas heat, AC, and large lot with 20 x 40 heated in-ground pool. Plus finished room with bath in walkout lower level. Current has laundry in the basement, but there are hookups on the first floor. Terrific village setting with proximity to shops, restaurants, and beach. Works well for year-round or second home. Taxes may vary due to owner use of property, buyer should confirm.
99 E Bay Rd, Osterville, MA 02655 is a 5 bedroom, 5 bathroom, 3,228 sqft single-family home in Osterville, built in 1973. It last sold for $1,450,000 on Jul 19, 2002. It is currently off market. The Trulia Estimate is $3,086,900, with a rent estimate of $6,755/month.

Home Details for 99 E Bay Rd

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Hardwood
Interior Details
Number of Rooms: 10Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Office
Appliances & Utilities
DishwasherRefrigerator

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Shingle Not Wood
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached

Property Information

Year Built
Year Built: 1973
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Lot Information

Lot Area: 0.84 acres

Price and Tax history

DateEventPrice
May 31, 2020
Source: Agent Provided
ListingRemoved
$1,599,000
Feb 24, 2020
Source: Agent Provided
Listed For Sale
$1,599,000
Nov 18, 2019
Source: Agent Provided
ListingRemoved
$1,599,000
May 23, 2019
Source: Agent Provided
PriceChange
$1,599,000
Price decreased by 5%
Jan 17, 2019
Source: Agent Provided
Listed For Sale
$1,689,000

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
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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

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Apartments for Rent

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Explore by feature - Pet Friendly

11 pet-friendly rentals in Osterville, MA

Explore by feature - Garage

13 rentals with a garage in Osterville, MA

Explore by feature - Air Conditioning

29 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 99 E Bay Rd

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Off Market Homes Near 99 E Bay Rd

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Frequently asked questions about 99 E Bay Rd

  • What is 99 E Bay Rd estimated to be worth?
    Trulia's estimated value for 99 E Bay Rd in Osterville, MA is $3,086,900.
  • What is the price history for 99 E Bay Rd?
    99 E Bay Rd in Osterville, MA last sold for $1,450,000 in July 2002.
  • 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 99 E Bay Rd have air conditioning?
    Yes, 99 E Bay Rd in Osterville, MA has air conditioning.
  • Does 99 E Bay Rd have laundry facilities?
    Yes, 99 E Bay Rd in Osterville, MA has laundry facilities.