Is Oakdale, Dedham, MA dog-friendly?

As of early 2026, 90% of users say it's dog friendly

Is parking easy in Oakdale, Dedham, MA?

As of early 2026, 88% of users say parking is easy

Is a car needed in Oakdale, Dedham, MA?

As of early 2026, 86% of users say car is needed

Does Oakdale, Dedham, MA have sidewalks?

As of early 2026, 85% of users say there are sidewalks

Does Oakdale, Dedham, MA show holiday spirit?

As of early 2026, 84% of users say there's holiday spirit

Are yards well-kept in Oakdale, Dedham, MA?

As of early 2026, 80% of users say yards are well-kept

Would people walk alone at night in Oakdale, Dedham, MA?

As of early 2026, 77% of users say people would walk alone at night

Is Oakdale, Dedham, MA quiet?

As of early 2026, 75% of users say it's quiet

Are the streets well-lit in Oakdale, Dedham, MA?

As of early 2026, 64% of users say streets are well-lit

Is there wildlife in Oakdale, Dedham, MA?

As of early 2026, 58% of users say there's wildlife

Is Oakdale, Dedham, MA walkable to restaurants?

As of early 2026, 56% of users say it's walkable to restaurants

Is Oakdale, Dedham, MA walkable to grocery stores?

As of early 2026, 55% of users say it's walkable to grocery stores

Do kids play outside in Oakdale, Dedham, MA?

As of early 2026, 55% of users say kids play outside

Do residents of Oakdale, Dedham, MA plan to stay at least 5 years?

As of early 2026, 54% of users say they plan to stay for at least 5 years

Are neighbors friendly in Oakdale, Dedham, MA?

As of early 2026, 49% of users say neighbors are friendly

Are there community events in Oakdale, Dedham, MA?

As of early 2026, 43% of users say there are community events

FOR SALE

NEW

OPEN SAT, 11-1PM

255 Madison St
Dedham, MA 02026

Oakdale

3 Beds
2 Baths
2,047 sqft

$899,900

Est. Mortgage $5,334/mo*

Get Pre-Qualified

$899,900

Est. Mortgage $5,334/mo*

Get Pre-Qualified

3 Beds

2 Baths

2,047 sqft

We estimate this home will sell faster than 95% nearby.

Local Information

Map ViewExplore the area around 255 Madison St.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

Pride of ownership defines this beautifully renovated Arts & Crafts style Cape, quietly tucked away on a dead-end street in the coveted Endicott neighborhood. Blending classic charm with modern luxury, the home features soaring ceilings, elegant French doors, and gleaming hardwood floors refinished in June 2026. Main level offers two spacious bedrooms, an updated full bath, 1st-floor laundry, and a cozy living area anchored by a Mendota gas fireplace (2022). 2nd Laundry in basement. Second floor is a private retreat boasting a large primary bedroom, an updated bath, and versatile open loft with a walk-in closet. Major updates over the last decade include a new roof (2018), Fujitsu AC mini splits (2019), new garage door (2020), and a fully fenced yard (2023). Enjoy morning coffee on the enclosed sun porch or entertain on the massive Trex deck overlooking the yard. Unbeatable location just 0.4 miles to the COMMUTER ENDICOTT TRAIN, Minutes to Legacy Place, and close to major highways

We estimate this home will sell faster than 95% nearby.

Open House

Saturday, June 27

11:00 AM to 1:00 PM

Sunday, June 28

11:00 AM to 12:30 PM

Home Highlights

Parking

Garage

Outdoor

Porch, Deck

A/C

Heating & Cooling

HOA

None

Price/Sqft

$440

Listed

2 days ago

Home Details for 255 Madison St

Interior Features
Interior Details Basement: Full,Interior Entry,BulkheadNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Master Bathroom, Bathroom 1, Bathroom 2, Dining Room, Kitchen, Living Room, Office
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout Living Area: 2047 Square Feet
Appliances & Utilities Utilities: for Gas Range, for Electric DryerAppliances: Gas Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Washer/DryerDishwasherDryerLaundry: First Floor,Electric Dryer HookupMicrowaveRefrigeratorWasher
Heating & Cooling Heating: Hot Water,Natural Gas,DuctlessHas CoolingAir Conditioning: DuctlessHas HeatingHeating Fuel: Hot Water
Fireplace & Spa Number of Fireplaces: 1Fireplace: Living RoomHas a FireplaceNo Spa
Gas & Electric Electric: Circuit Breakers, 200+ Amp Service
Windows, Doors, Floors & Walls Door: French DoorsFlooring: Wood, Tile, Flooring - Hardwood
Levels, Entrance, & Accessibility Floors: Wood, Tile, Flooring Hardwood

Exterior Features
Exterior Home Features Roof: Shingle RubberPatio / Porch: Porch - Enclosed, Deck - VinylFencing: FencedExterior: Porch - Enclosed, Deck - Vinyl, Rain Gutters, Storage, Professional Landscaping, Sprinkler System, Fenced YardFoundation: StoneSprinkler System
Parking & Garage Open Parking Spaces: 2No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: Detached,Garage Door Opener,Storage,Workshop in Garage,Paved Drive,Off Street
Frontage Road Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer Sewer: Public Sewer
Finished Area Finished Area (above surface): 2047

Days on Market
Days on Market: 2

Property Information
Year Built Year Built: 1936
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape
Building Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information Parcel Number: M:0152 L:0046, 72527

Price & Status
Price List Price: $899,900Price Per Sqft: $440

Active Status
MLS Status: New

Location
Direction & Address City: DedhamCommunity: Endicott
School Information Elementary School: OakdaleJr High / Middle School: DedhamHigh School: Dedham

Agent Information
Listing Agent Listing ID: 73541756

Building
Building Area Building Area: 2047 Square Feet

Community
Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station, SidewalksNot Senior Community

HOA
No HOA

Lot Information
Lot Area: 9344 sqft

Miscellaneous
BasementMls Number: 73541756Above Grade Unfinished Area: 2047

Additional Information
Public TransportationShoppingTennis Court(s)ParkBike PathConservation AreaHighway AccessHouse of WorshipPrivate SchoolPublic SchoolT-StationSidewalks

Last check for updates: about 19 hours ago

Listing courtesy of Anne Fahy, (617) 257-8088

Coldwell Banker Realty - Canton, (781) 821-2664

Source: MLS PIN, MLS#73541756

Also Listed on MLS PIN.

Market trends in Dedham

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

10MoM

Price History for 255 Madison St

Date	Price	Event	Source
06/25/2026	$899,900	Listed For Sale	MLS PIN #73541756

06/06/2014	$529,600	Sold	N/A
Recording Date 06/06/2014 County Transfer Tax N/A Total Transfer Tax $61
02/17/2014	$525,000	ListingRemoved	Agent Provided

02/13/2014	$525,000	Listed For Sale	Agent Provided

07/15/2005	$485,000	Sold	N/A
Recording Date 07/15/2005 County Transfer Tax N/A Total Transfer Tax N/A
02/04/2005	$316,000	Sold	N/A
Recording Date 02/04/2005 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$9,528
Assessment	$755,000

Home facts updated by county records

Comparable Sales for 255 Madison St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
731 East St, Dedham, MA	0.10	Single-Family Home	$851,000	12/01/25	3	1.5	2,324
254 Madison St, Dedham, MA	0.02	Single-Family Home	$580,000	08/28/25	2	2	1,456
6 Snow Ln, Dedham, MA	0.21	Single-Family Home	$780,000	03/31/26	3	1.5	1,288
438 Mount Vernon St, Dedham, MA	0.37	Single-Family Home	$850,000	04/29/26	3	2	2,039
398 Mount Vernon St, Dedham, MA	0.32	Single-Family Home	$925,000	08/25/25	3	2	1,981
16 Glenway St, Dedham, MA	0.18	Single-Family Home	$670,000	12/01/25	4	1.5	1,470
183 Grant Ave, Dedham, MA	0.23	Single-Family Home	$665,000	11/07/25	2	1.5	1,349
16 Norwich St, Dedham, MA	0.53	Single-Family Home	$620,000	01/06/26	3	1.5	2,061
59 Hamilton Ave, Dedham, MA	0.19	Single-Family Home	$765,000	05/08/26	4	2.5	1,844
18 Boulevard Rd, Dedham, MA	0.26	Single-Family Home	$800,000	11/13/25	4	2.5	1,710

Nearby homes

Get a sense of prices in the area by checking nearby homes.

Skip to last item

SOLD
AUG 28, 2025
$580,000
2 bd
2 ba
1,456 sqft
254 Madison St,
Dedham, MA 02026
Stockman Farrar Group, Berkshire Hathaway HomeServices Commonwealth Real Estate
OFF MARKET
Est. $873,400
3 bd
1.5 ba
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14 Thompson St,
Dedham, MA 02026
Nancy & Tara, Gibson Sotheby's International Realty
OFF MARKET
Est. $857,100
3 bd
3 ba
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50 Thompson St,
Dedham, MA 02026
Richard C. Dore, Hammond Residential Real Estate
SOLD
DEC 1, 2025
$851,000
3 bd
1.5 ba
2,324 sqft
731 East St,
Dedham, MA 02026
Alan Ginsberg, Donalan Group Realty, Inc.
OFF MARKET
Est. $925,900
3 bd
2 ba
1,848 sqft
203 Madison St,
Dedham, MA 02026
Francis J. Curran, Coldwell Banker Realty - Westwood
FOR SALE
NEW
OPEN SAT, 10:30-12PM
$799,900
4 bd
2 ba
1,970 sqft
812 East St,
Dedham, MA 02026
Paul White, Keller Williams Realty Signature Properties
OFF MARKET
Est. $722,500
2 bd
1.5 ba
869 sqft
724 East St,
Dedham, MA 02026
Ron Resha, Coldwell Banker Realty - Canton
OFF MARKET
Est. $883,100
3 bd
2 ba
1,499 sqft
223 Fairbanks Rd,
Dedham, MA 02026
Deborah Mulroy, Donahue Real Estate Co.
OFF MARKET
Est. $740,900
3 bd
1 ba
1,296 sqft
819 East St,
Dedham, MA 02026
Gary Blattberg, RE/MAX 360
OFF MARKET
Est. $672,200
2 bd
1 ba
1,301 sqft
202 Madison St,
Dedham, MA 02026
Katherine Tirrell, Grade A Realty
OFF MARKET
Est. $850,800
3 bd
2 ba
1,498 sqft
710 East St,
Dedham, MA 02026
Betsy Hill, Coldwell Banker Realty - Newton

Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 255 Madison St.

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

Oakdale

12 Homes For You
Buy: $575k - $1.25m

See Local Highlights

Neighborhood stats provided by third party data sources.

What Locals Say about Oakdale

At least 42 Trulia users voted on each feature.

90 % Say it's dog friendly
88 % Say parking is easy
86 % Say car is needed
85 % Say there are sidewalks
84 % Say there's holiday spirit
80 % Say yards are well-kept
77 % Say people would walk alone at night
75 % Say it's quiet
64 % Say streets are well-lit
58 % Say there's wildlife
56 % Say it's walkable to restaurants
55 % Say it's walkable to grocery stores
55 % Say kids play outside
54 % Say they plan to stay for at least 5 years
49 % Say neighbors are friendly
43 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Alisonbarnett8
Resident
6mo ago
"Legacy Place is next door as well as the commuter rail. The complex we live in has several events around the holidays. "
0
Flag
Eileen M. B.
Resident
5y ago
"Best recreation department and friendly people. Very walkable with nice parks and open space. A commuters dream."
0
Flag
Jon S.
Resident
6y ago
"Dedham is close to highways and public transportation. It has new elementary and middle schools but taxes are rather high. "
0
Flag
Eileenmurraybrooks
Resident
6y ago
"I work in a home office so I don’t have a commute, that being said commuting downtown is very easy on the train. "
0
Flag
Eileenmurraybrooks
Resident
6y ago
"The commute is much easier than other places because it is within the route 95 belt. You don’t have to go on a highway to get into Boston. "
0
Flag
Eileen M. B.
Resident
6y ago
"I work 15 minutes from here now by car, but for years I commuted to the Prudential tower downtown and it was a very easy and pleasant commute on the commuter rail. "
0
Flag
Eileen B.
Resident
7y ago
"Oakdale is a wonderful neighborhood located close the the center, library, Endicott Estate (summer concerts, etc.) commuter rail and more. Best decision to buy here. Great shopping and restaurants."
0
Flag
Clarissa
Resident
7y ago
"Safe neighborhood, difficult to walk/bike around with traffic. Lots of community events and groups to become involved in. "
0
Flag
Benosebey
Resident
7y ago
"I've lived here for 12years now, great neighborhood, some people are great others not so much. great schools around here, there are some great places to visit/shop and eat."
5
Flag
Caren B.
Resident
7y ago
"I like the side streets where I walk my dog, but it is hard to cross the main roads."
0
Flag
Caren B.
Resident
7y ago
"I walk around my neighborhood all of the time."
0
Flag
Caren B.
Resident
7y ago
"There is an Oakdale Alliance and they offer events to get the neighborhood together that has events throughout the year."
0
Flag
Caren B.
Resident
7y ago
"There is a great school and a lot of kids in the area."
0
Flag
Gabby C.
Resident
8y ago
"They would like the dog friendly park. There are also a few trails in Dedham that you can walk on. The sidewalks are nicely done as well, so that makes it easier for people and pets to walk."
0
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Gabby C.
Resident
8y ago
"I don't have a car. It's pretty easy to get to places I need to by walking, though. Pretty much everything is within walking distance. Traffic is usually not too bad. Sometimes it can get annoying though."
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Gabby C.
Resident
8y ago
"There are so many things to do! We have so many stores and little shops."
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Gabby C.
Resident
8y ago
"It's pretty safe and family friendly. The schools and extra curricular activities are really good and well planned. The teachers work really hard and are great at what they do."
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Harlee O.
Resident
8y ago
"They would like everything because it is a perfect place to have a dog."
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Harlee O.
Resident
8y ago
"It is easy and fast to get anywhere you want to go in Dedham."
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Harlee O.
Resident
8y ago
"The people make it a fun and loving environment."
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Harlee O.
Resident
8y ago
"It is a very safe place for kids to roam freely."
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Roma
12y ago
"Great family friendly neighborhood with great access to shops, entertainment and public transport for commuting. Great Curb appeal Beautiful Period home"
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Johnrh1958
12y ago
"Really nice quiet neighborhood. well maintained. walk to commuter rail. Friendly."
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dsr
13y ago
"Handy to everything, walk to commuter rail, 20 min drive to Boston Common, 5 min to 128...walk to all schools...quiet, trees all over, beautiful churches and classic NE architecture (and variety!)...nice mix of old and young people, small shops nearby, quiet and safe...and unpretentious!"
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LGBTQ Local Legal Protections

Anne Fahy, Coldwell Banker Realty - Canton, (781) 821-2664

Agent Phone: (617) 257-8088

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
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255 Madison St, Dedham, MA 02026 is a 3 bedroom, 2 bathroom, 2,047 sqft single-family home built in 1936. 255 Madison St is located in Oakdale, Dedham. This property is currently available for sale and was listed by MLS PIN on Jun 25, 2026. The MLS # for this home is MLS# 73541756.

255 Madison St Dedham, MA 02026

$899,900

$899,900

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255 Madison St
Dedham, MA 02026