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$2,495,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 4,227 Sq. Ft.
  • 0.56 Acres
  • Updated 3 hours ago

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Open House: 12:00 PM - 2:00 PM

Sunday 5/3 12:00 PM - 2:00 PM

279 Oakland Street,Wellesley, MA 02481

279 Oakland StreetWellesleyMA02481

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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

Full Property Details for 279 Oakland St

General

  • Price: $2,495,000
  • Taxes: $20,482 (2026)
  • Status: Active
  • Type: Single Family
  • MLS ID: 73509829
  • Updated: 5/3/2026
  • Added to Site: 4 day(s) ago

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Bathroom 1: First
  • Bathroom 2: Second
  • Bathroom 3: Second

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: 18.00 x 20.00, Second
  • Bedroom 2: 16.00 x 12.00, Second
  • Bedroom 3: 11.00 x 17.00, Second
  • Bedroom 4: 13.00 x 11.00, Second

Other Rooms

  • Living Room: 13.00 x 21.00, First
  • Family Room: 20.00 x 23.00, First
  • Kitchen: 16.00 x 15.00, First
  • Dining Room: 16.00 x 14.00, First
  • Office: 10.00 x 10.00, Second

Parking

  • Parking Features: Paved Drive, Off Street, Paved

Location

  • County: Norfolk

Structural Information

  • Architectural Style: Garrison
  • Basement: Yes
  • Square Feet: 4,227
  • Year Built: 1948

Lot Features

  • Lot Size (Acres): 0.56

Financial Considerations

  • Tax Amount: $20,482
  • Tax Year: 2026

Disclosures and Reports

  • Disclosures/Rstr.: Per Seller the light pole at driveway does not work
  • Property ID: 257458

Listed by William Raveis R.E. & Home Services, Christine Norcross & Partners and Christine Norcross

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Listing agents

— 279 Oakland St —

  • Christine Norcross & Partners

    William Raveis R.E. & Home Services

  • Christine Norcross

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 279 Oakland St

School District:Wellesley School District
NameGradesDistance
Joseph E. Fiske Elementary School
45 Hastings Street, Wellesley, MA 02481
K-50.4 mi
Wellesley Middle School
50 Kingsbury Street, Wellesley, MA 02481
6-82.1 mi
Wellesley High School
50 Rice Street, Wellesley, MA 02481
9-121.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 279 Oakland St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/29/2026
Listed
$2,495,000
303.72%
MLS
3/17/2000
Sold
$618,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 279 Oakland St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$19,892
3%
$1,935,000
4%
2024
$19,279
2%
$1,852,000
12%
2023
$18,927
11%
$1,653,000
14%
2022
$16,983
-1%
$1,454,000
—
2021
$17,085
2%
$1,454,000
—
2020
$16,808
3%
$1,454,000
3%
2019
$16,348
8%
$1,413,000
11%
2018
$15,188
1%
$1,271,000
—
2017
$14,985
2%
$1,271,000
2%
2016
$14,740
2%
$1,246,000
—
2015
$14,415
4%
$1,247,000
4%
2014
$13,894
—
$1,204,000
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Be ready to buy your new home!

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NMLS#: 1598647

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Listed by William Raveis R.E. & Home Services, Christine Norcross & Partners and Christine Norcross

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279 Oakland Street, Wellesley, MA 02481 (MLS# 73509829) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 279 Oakland Street is currently listed for $2,495,000 and was received on April 29, 2026. Want to learn more about 279 Oakland Street? Do you have questions about finding other Single Family real estate for sale in Wellesley? You can browse all Wellesley real estate or contact a Coldwell Banker agent to request more information.

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