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Luxury Homes in Wellesley, MA — Page 2
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Luxury Homes in Wellesley, MA

Luxury Homes in Wellesley, MA

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24 of 52 Listings
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Luxury Homes in Wellesley, MA

24 of 52 Listings

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Thomas O'Leary

Realty.com

Lic. #1000018

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  1. 16 Stearns Rd #108 — photo12Active

    $1,675,000

    2 bd · 3 ba · 1,792 sqft

    16 Stearns Rd #108, Wellesley, MA

    Bartlett Albion Group · Hammond Residential Real Estate

  2. 97 Arnold Road — photo37Active

    $4,980,000

    5 bd · 5 ba · 5,296 sqft

    97 Arnold Road, Wellesley, MA

    Bobby Morgenstern · Gibson Sotheby's International Realty

  3. 55 Ridge Hill Farm Rd — photo42Active

    $5,350,000

    5 bd · 8 ba · 8,700 sqft

    55 Ridge Hill Farm Rd, Wellesley, MA

    Debi Benoit · William Raveis R.E. & Home Services

  4. 9 Fells Circle — photo27Active

    $1,730,000

    5 bd · 4 ba · 4,471 sqft

    9 Fells Circle, Wellesley, MA

    Qian Han · JW Real Estate Services, LLC

  5. 39 Fairbanks Ave — photoOpen house Sun, Oct 18 · 12:30 PM42Active

    $3,995,000

    5 bd · 6 ba · 5,059 sqft

    39 Fairbanks Ave, Wellesley, MA

    Donahue Maley and Burns Team · Compass

  6. 25 Mansfield Road — photo1Active

    $3,650,000

    5 bd · 5 ba · 6,550 sqft

    25 Mansfield Road, Wellesley, MA

    Melissa Dailey · Coldwell Banker Realty - Wellesley

  7. 560 Worcester St — photoPrice Reduced40Active

    $1,349,000

    4 bd · 3 ba · 1,800 sqft

    560 Worcester St, Wellesley, MA

    Debi Benoit · William Raveis R.E. & Home Services

  8. 53 Elmwood Rd — photo20Active

    $1,950,000

    3 bd · 2 ba · 1,595 sqft

    53 Elmwood Rd, Wellesley, MA

    Donahue Maley and Burns Team · Compass

  9. 23 Wareland Rd — photoOpen house Sun, Oct 18 · 12:00 PM29Active

    $3,050,000

    5 bd · 5 ba · 6,006 sqft

    23 Wareland Rd, Wellesley, MA

    Donahue Maley and Burns Team · Compass

  10. 29 Cottage Street — photoPrice ReducedOpen house Sun, Oct 18 · 10:00 AM33Active

    $1,650,000

    4 bd · 4 ba · 2,086 sqft

    29 Cottage Street, Wellesley, MA

    Paula Carens · Paula Carens

  11. 43 Atwood St — photoPrice ReducedOpen house Sun, Oct 18 · 11:00 AM23Active

    $1,525,000

    3 bd · 2 ba · 2,148 sqft

    43 Atwood St, Wellesley, MA

    Brian McMahon · Rutledge Properties

  12. 23 Bellevue — photoPrice Reduced34Active

    $3,600,000

    5 bd · 6 ba · 6,289 sqft

    23 Bellevue, Wellesley, MA

    Ritu Chawla · Coldwell Banker Realty - Wellesley

  13. 12 Winding River Cir — photo39Active

    $4,999,000

    6 bd · 9 ba · 8,729 sqft

    12 Winding River Cir, Wellesley, MA

    Christine Lawrence · Rutledge Properties

  14. 265 Weston Rd — photoPrice ReducedOpen house Sun, Oct 18 · 1:30 PM37Active

    $2,750,000

    5 bd · 6 ba · 5,172 sqft

    265 Weston Rd, Wellesley, MA

    Petrone-Hunter Realty Group · Coldwell Banker Realty - Wellesley

  15. 26 Pleasant St #B — photoPrice Reduced20Active

    $1,019,999

    2 bd · 2 ba · 1,739 sqft

    26 Pleasant St #B, Wellesley, MA

    Zhen Guo · Coldwell Banker Realty - Brookline

  16. 43 Monadnock Road — photoPrice Reduced42Active

    $4,995,000

    6 bd · 6 ba · 7,738 sqft

    43 Monadnock Road, Wellesley, MA

    Melissa Dailey · Coldwell Banker Realty - Wellesley

  17. 22 Cedar St — photoPrice ReducedOpen house Sun, Oct 18 · 11:00 AM37Active

    $1,195,000

    3 bd · 3 ba · 1,848 sqft

    22 Cedar St, Wellesley, MA

    The Shulkin Wilk Group · Compass

  18. 16 Stearns Rd #304 — photo13Active

    $1,599,000

    2 bd · 2 ba · 1,591 sqft

    16 Stearns Rd #304, Wellesley, MA

    Bartlett Albion Group · Hammond Residential Real Estate

  19. 209 Bristol Rd — photoPrice ReducedOpen house Sun, Oct 18 · 12:00 PM29Active

    $3,095,000

    6 bd · 5 ba · 4,424 sqft

    209 Bristol Rd, Wellesley, MA

    Elisabeth Preis · Compass

  20. 45 White Oak Rd — photoPrice Reduced40Active

    $8,995,000

    5 bd · 6 ba · 7,200 sqft

    45 White Oak Rd, Wellesley, MA

    The Sarkis Team · Douglas Elliman Real Estate - The Sarkis Team

  21. 30R Morses Pond Road — photoPrice Reduced23Active

    $1,300,000

    3 bd · 2 ba · 1,640 sqft

    30R Morses Pond Road, Wellesley, MA

    Patricia Bradley · Rutledge Properties

  22. 45 Longmeadow Rd — photoPrice Reduced42Active

    $5,500,000

    7 bd · 9 ba · 7,600 sqft

    45 Longmeadow Rd, Wellesley, MA

    Lisa Sewall · Coldwell Banker Realty - Wellesley

  23. 77 Cedar Street — photoPrice Reduced39Active

    $2,045,000

    5 bd · 4 ba · 3,704 sqft

    77 Cedar Street, Wellesley, MA

    The Lara & Chelsea Collaborative · Coldwell Banker Realty - Wellesley

  24. 16 Stearns Rd. #203 — photoPrice Reduced19Active

    $1,498,000

    2 bd · 3 ba · 1,604 sqft

    16 Stearns Rd. #203, Wellesley, MA

    Bartlett Albion Group · Hammond Residential Real Estate

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The property listing data and information 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 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 set forth herein.
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  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #1000018

    Call Thomas

    Wellesley, MA community profile

    Area
    4.8 sq. mi.

    Source: HJN community data

    Wellesley housing market

    September 2026 · This period is still settling

    Selling at 98.7% of asking price

    Buyers here are paying below asking. MLS · 12 sales · as of Sep 29, 2026

    Homes on the market · MLS, as of Sep 27, 2026

    Median list price
    $2,450,000
    Homes for sale
    29

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 10, 2026

    Median home size
    2,458 sq. ft.