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279 Oakland StreetWellesley, MA 02481

For Sale

$2,495,000

Smart Buyer Rebate $12,475

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

Listed by Christine Norcross

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William Raveis R.E. & Home Services

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781-929-4994

Listed by Christine Norcross & Partners

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William Raveis R.E. & Home Services

Listed by Ralph Vezina

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William Raveis R.E. & Home Services

Last updated April 30, 2026

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Source: MLSPin #73509829

Listing Facts

  • TypeSingle-family
  • NeighborhoodWellesley Hills
  • Bedrooms5
  • Bathrooms4
  • Days on Prevu1
  • Taxes$20,482/year
  • Size4,227 sqft
  • Price per sqft$590

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

04/29/2026
Listed by William Raveis R.E. & Home Services
$2,495,000

Property Details for 279 Oakland Street

Association

Amenities

  • Community Features: Public Transportation, Shopping, Park

Exterior

Construction

  • Roof: Shingle, Rubber
  • Window Features: Insulated Windows
  • Year Built: 1948
  • Year Built Details: Actual
  • Architectural Style: Garrison
  • Construction Materials: Frame
  • Exterior Features: Porch, Patio, Rain Gutters, Professional Landscaping, Sprinkler System

Features

  • Patio And Porch Features: Porch, Patio
  • Road Frontage Type: Public

Measurements

  • Building Area Total: 4,227
  • Building Area Units: Square Feet
  • Lot Size Acres: 0.56
  • Lot Size Area: 0
  • Lot Size Square Feet: 24,400
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: 257458
  • Tax Annual Amount: $20,482.00
  • Tax Assessed Value: $2,014,000.00
  • Tax Year: 2026

Interior

Features

  • Appliances: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
  • Fireplace Features: Living Room
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Flooring: Wood, Tile, Carpet, Flooring - Stone/Ceramic Tile, Flooring - Wall To Wall Carpet, Flooring - Hardwood
  • Interior Features: Recessed Lighting, Bathroom - Full, Sitting Room, Sun Room, Bonus Room, Bathroom, Home Office

Measurements

  • Living Area: 4,227
  • Living Area Source: Measured

Rooms

  • Basement: Full, Finished
  • Bathrooms Full: 3
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 4
  • Bedrooms Total: 5
  • Rooms Total: 13

Other

Environmental

  • Green Energy Efficient: Thermostat

Parking

Parking

  • Open Parking Spaces: 6
  • Open Parking: Yes
  • Parking Features: Paved Drive, Off Street, Paved
  • Parking Total: 6

Schools

Elementary School

  • Elementary School: Fiske

High School

  • High School: Wellesley Hs

Middle or Junior School

  • Middle Or Junior School: Wellesley Ms

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Electric: Circuit Breakers, 200+ Amp Service
  • Heating: Forced Air, Fireplace(s)
  • Has Heating: Yes
  • Laundry Features: Flooring - Stone/Ceramic Tile, Recessed Lighting, Sink, In Basement, Electric Dryer Hookup
  • Sewer: Public Sewer
  • Utilities: For Electric Dryer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 5 bedrooms and 4 bathrooms in this single-family home at 279 Oakland Street.

What schools are nearby to 279 Oakland Street?

Nearby schools include the Fiske Elementary School, Wellesley Ms Middle School, and Wellesley Hs High School.

Does this single-family home have parking?

Yes, there are 6 parking spaces available for 279 Oakland Street.

What are the annual taxes for 279 Oakland Street?

Annual taxes for this single-family home are estimated at $20,482.

How does 279 Oakland Street compare to other single-family homes in Wellesley Hills?

This single-family home is listed 24% below the average price for single-family homes in Wellesley Hills and has been on the market for 48 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 4,227 sqft.

279 Oakland Street is a 5-bedroom, 4-bath single-family home for sale in Wellesley MA 02481. Listed on Prevu for 1 days at $2,495,000. This property features 4,227 square feet of living space, located in Wellesley Hills. The median listing price for single-family homes in this area is $3,445,000. Nearby schools include Fiske Elementary School, Wellesley Ms Middle School, and Wellesley Hs High School. Additional amenities include private outdoor space, dishwasher, air conditioning, parking, and washer/dryer. Browse more single-family home listings in Norfolk County.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting 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, leasing or renting. 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, or as to the accuracy of any of the Images, set forth herein.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.