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279 Oakland Street — Photo 11 / 30

$2,495,000

Active

279 Oakland Street

Wellesley, MA 02481

5Beds
3.5Baths
4,227Sq Ft
$590$/Sq Ft
24,400 sqftLot
1948Built
18Days on Market

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

Listing courtesy of Christine Norcross & Partners, William Raveis R.E. & Home Services

About This Property

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

Property Details

Key Facts

Property Type

Single Family

Style

Bungalow

Year Built

1948

Living Area

4,227 sqft

Lot Size

24,400 sqft

Rooms

13

Bedrooms

5

Bathrooms

3.5 (3 full, 1 half)

Construction

Exterior

A

Basement

Full Basement

Flooring

Softwood, Wall to Wall Carpet, Hardwood

Parking Spaces

6

Systems & Utilities

Heating

Hot Water Baseboard

Cooling

Central Air

Water

City/Town Water

Sewer

City/Town Sewer

Financial

Taxes (2026)

$20,482/yr

Price / Sqft

$590/sqft

MLS #

73509829

Days on Market

18

Price History

Listed

May 6, 2026

$2,495,000

No price changes recorded.

Explore the Neighborhood

Schools Nearby

Wellesley Public Schools

9 schools · 11:1 student-teacher ratio

A+9/10

Elementary Schools

Bates Elementary School (K-5)8/10
Sprague Elementary School (K-5)8/10
Fiske Elementary School (K-5)8/10

Middle Schools

Wellesley Middle School (6-8)8/10

High Schools

Wellesley Senior High School (9-12)10/10
Gateways Program (therapeutic academic support at WHS)Strong AP course offerings across all academic departmentsPartnership opportunities with Wellesley CollegeComprehensive arts program (visual, performing, music)

Ratings from GreatSchools & Niche

Full school details →
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Listing Courtesy Of

Christine Norcross & Partners · William Raveis R.E. & Home Services
(781) 235-5000

MLS #73509829

Listing information provided by MLS Property Information Network, Inc. (MLS PIN). Data last updated May 24, 2026. Information deemed reliable but not guaranteed. © 2026 Steinmetz Real Estate Professionals at William Raveis Real Estate. Equal Housing Opportunity.

Home Value