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279 Oakland Street, Wellesley MA 02481

$2,495,000

Estimated $17,080/month Calculator

Single Family

5 Bedrooms

Baths

4227

Total Parking: 6

24,400 (0.56)

Built in 1948

Timeless Garrison nestled on a picturesque half-acre lot. Extensively renovated and expanded in 2005, this beautifully updated 4,000+ sq ft home blends classic New England charm with modern luxury just steps to Longfellow Pond. Thoughtfully designed with exceptional space & inviting gathering areas, the chef’s kitchen with oversized island opens to a fireside sitting area, the expansive family room flows seamlessly to an elegant fireplaced living room with French doors leading to a private stone patio. Upstairs, the serene primary suite features a walk-in closet and double vanity, along with three additional bedrooms & dedicated home office. The finished lower level offers a recreation room, full bath, & oversized laundry. Meticulously maintained with major system updates, including newer furnaces, central air, & hot water heater. Close to Needham & Wellesley MBTA, this exceptional home offers a rare blend of lifestyle, location, and design. Fiske Elementary is a Blue Ribbon school

This home has been viewed 3 times

Last Checked: May 5th, 2026 at 8:13pm (Source: MLS PIN #73509829)

Green Features

Air Conditioning

Lead Paint Free

General Information for 279 Oakland Street, Wellesley MA 02481

Listing ID73509829

Property TypeSingle Family / Detached

Price$2,495,000 ($590.25/SqFt)

StyleColonial

CityWellesley

CountyNorfolk

Neighborhood(s)

Garage Parking0

ZoningSR15

Year Built1948

Year Built SourcePublic Records

Year Built DetailsActual

Interior Features for 279 Oakland Street, Wellesley MA 02481

Approximate Living Area Total4227

Living Area Includes BasementYes

Rooms13

Bedrooms5

Primary En Suite BathroomYes

BasementFull

Cooling1, Split

Fireplaces

AppliancesRange

FlooringTile

Electric220 Volts

Exterior Features for 279 Oakland Street, Wellesley MA 02481

Approximate Lot Size (Acres)0.56

Approximate Lot Size (Square Feet)24400

Total Parking6

Garage Parking0

WaterPublic

SewerPublic Sewer

Lot Features

Parking Features1

Exterior FeaturesPorch

Foundation Area999

Foundation Materials

Construction MaterialsFrame

Road Frontage Type

Patio & PorchCovered

Roof MaterialAsphalt/fiberglass Shingles

Utility Connections110 Volts

Water Views

Water Views Features

Waterfront0

Waterfront Features

Pool Features

Horse Permitted0

Horse Amenities

Disclosures for 279 Oakland Street, Wellesley MA 02481

Lead PaintNone

UFFI

Living Area Includes BasementYes

Living Area Disclosure

Building Area SourceMeasured

Special Listing Conditions

ExclusionsAll Personal Property.

Compensation Based On

Financial Information for 279 Oakland Street, Wellesley MA 02481

Association Fee

Association Fee Frequency

Association Fee Includes

Real Estate Tax20482

Tax Year2026

Assessed Value$2,014,000

Location Information for 279 Oakland Street, Wellesley MA 02481

Elementary SchoolFiske

Middle SchoolWellesley Ms

High SchoolWellesley Hs

Neighborhood(s)

Area AmenitiesWalk/jog Trails

Contact Information for 279 Oakland Street, Wellesley MA 02481

Agent

Name: Christine Norcross & Partners

Office

Name: William Raveis R.E. & Home Services

Phone: 781-235-5000

Team Members

Name: Christine Norcross

Payment Calculator

, Interest

Property Taxes 1706.83

Principal & Interest 15373.4

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

William Raveis R.E. & Home Services

Christine Norcross & Partners

Agent Phone

Office Phone

(781) 235-5000

Text Agent Call Agent Call Office

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EXIT

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