279 Oakland Street Wellesley, MA ^$ 2,495,000

279 Oakland Street

^$ 2,495,000

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Open House 5/1 4:30pm - 6pm

279 Oakland Street

Wellesley, MA, 02481

^$ 2,495,000

Bedrooms5 Baths3.1 Sq 4,227

Monthly Estimate*

^$ 15,362

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Single Family Home for sale in Wellesley, MA

for $2,495,000 with 5 bedrooms and 3 full baths, 1 half bath. This 4,227 square foot home was built in 1948 on a lot size of 0.56.

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

Open House

5/1/2026 4:30 PM - 6:00 PM

5/2/2026 12:00 PM - 2:00 PM

5/3/2026 12:00 PM - 2:00 PM

279 Oakland Street Wellesley, MA

* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

^$ 2,495,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 20,482

Style

Garrison

Lot Size

0.56

Year Built

1948

Town/City

Wellesley

County/Region

Norfolk

MLS | Web ID

73509829

List By

Christine Norcross & Partners

Listing Agent

William Raveis R.E. & Home Services

Broker

Affordability Calculator

$17,069

Per Month

Monthly Principal & Interest: $15,362
Monthly Property Taxes: $1,707
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends

Single family listings in Wellesley, MA

Average List Price ^$3,372,169

Percent of Sale Price 35%

About Wellesley, MA

28,724 Population

8% Since 2002

^$170,623 Median Income

35.33 Median Age

42% Households with Children

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Trends Information provided by ATTOM Data Solutions.

Neighborhood & Schools

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Pricing History

Date	Price	Price Change	Description
4/29/2026	$2,495,000		Listed Price

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279 Oakland Street, Wellesley, MA, 02481 is a Single Family Home for sale at $2,495,000 with 4,227 sqft and a lot size of 0.56. 279 Oakland Street has 5 bedrooms, 3.1 baths, and was built in 1948. The property's zip code is 02481 which is in Wellesley, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 5/1/2026.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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 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 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, or as to the accuracy of any of the Images, set forth herein.

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279 Oakland Street

Single Family Home for sale in Wellesley, MA

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