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Wellesley Hills Homes for Sale

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  • 179 Oakland St, Wellesley Hills, MA 02481
    179 Oakland St, Wellesley Hills, MA 02481
    179 Oakland St, Wellesley Hills, MA 02481
    /42

    $4,870,000

    • 6 Beds
    • 8 Baths
    • 7,197 Sq Ft

    179 Oakland St, Wellesley Hills, MA 02481

    Overlooking the sweeping 18-hole vistas of Wellesley Country Club, this exceptional Colonial estate blends timeless New England elegance with refined modern living. Thoughtfully redesigned over a two-year collaboration with a premier design team, every detail — from the architecture and lighting to the soft blue-gray palette — was carefully curated to complement the surrounding landscape and

    Lin Shi Phoenix Real Estate

    179 Oakland St, Wellesley Hills, MA 02481
  • 6 Willow St, Wellesley, MA 02481
    6 Willow St, Wellesley, MA 02481
    6 Willow St, Wellesley, MA 02481
    /37

    $1,100,000

    Open Sun 12PM - 1PM $98K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,165 Sq Ft

    6 Willow St, Wellesley, MA 02481

    A great opportunity for a buyer who understands the value of sweat equity and is willing to make some improvements! This delightfully charming Cape style home offers a versatile open concept floor plan. The first floor flows seamlessly to two separate fireplace living areas as well as a dining room with hardwood flooring throughout. The updated kitchen boasts granite countertops, stainless

    Frank Celeste Gibson Sotheby's International Realty

    6 Willow St, Wellesley, MA 02481
  • 151 Oakland St, Wellesley Hills, MA 02481
    151 Oakland St, Wellesley Hills, MA 02481
    151 Oakland St, Wellesley Hills, MA 02481
    /42

    $3,850,000

    Open Sun 12PM - 1:30PM $1M PRICE DROP
    • 6 Beds
    • 5 Baths
    • 6,990 Sq Ft

    151 Oakland St, Wellesley Hills, MA 02481

    Located in the Country Club neighborhood on 1.15 acres, overlooking Wellesley Country Club greens, with sweeping scenic golf course views. Renovations in 2022, this home blends historic character with refined luxury, featuring wide pine floors, 6 fireplaces, and walls of windows overlooking the greens. Gracious living spaces include an inviting fire-placed great room, sophisticated library,

    Beth Dickerson Gibson Sotheby's International Realty

    151 Oakland St, Wellesley Hills, MA 02481
  • 41 Hunnewell St, Wellesley Hills, MA 02481
    41 Hunnewell St, Wellesley Hills, MA 02481
    41 Hunnewell St, Wellesley Hills, MA 02481
    /21

    $1,348,000

    $50K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,384 Sq Ft

    41 Hunnewell St, Wellesley Hills, MA 02481

    Privately set on 1.42 acres at the end of a secluded cul-de-sac, this gracious Colonial offers a rare blend of privacy, natural beauty, and timeless charm. Surrounded by mature trees and picturesque grounds, the home features sun-filled living spaces, an inviting family room with cathedral ceiling, spacious living room, and two fireplaces that bring warmth and character throughout. The generous

    Christine Norcross William Raveis R.E. & Home Services

    41 Hunnewell St, Wellesley Hills, MA 02481
  • 22 Cedar St, Wellesley Hills, MA 02481
    22 Cedar St, Wellesley Hills, MA 02481
    22 Cedar St, Wellesley Hills, MA 02481
    /37

    $1,275,000

    Open Sun 12PM - 1:30PM
    • 3 Beds
    • 3 Baths
    • 1,848 Sq Ft

    22 Cedar St, Wellesley Hills, MA 02481

    Classic charm meets modern luxury in this beautifully updated 3-bedroom, 3-bathroom 1920's Colonial. The main level welcomes you with high ceilings, an open concept layout and an abundance of natural light throughout. Flexible space for living and dining as well as generous family room. Gorgeous modern eat in kitchen with stainless steel appliances and gas cooking. Step outside to your private

    The Shulkin Wilk Group Compass

    22 Cedar St, Wellesley Hills, MA 02481
  • 31 Lantern Ln, Wellesley Hills, MA 02481
    31 Lantern Ln, Wellesley Hills, MA 02481
    31 Lantern Ln, Wellesley Hills, MA 02481
    /20

    $1,299,000

    • 4 Beds
    • 2 Baths
    • 2,233 Sq Ft

    31 Lantern Ln, Wellesley Hills, MA 02481

    Wonderful opportunity to own an affordable two-family home in Wellesley. Don't miss this charming two-family home nestled in a desirable neighborhood setting — rich in character and architectural detail with a stunning wrap-around porch that sets it apart. Each unit offers 2 bedrooms, updated electrical service, and a large detached 2-car garage adds exceptional value. Commuters will love the

    Ned Mahoney eXp Realty LLC - Corporate Office

    31 Lantern Ln, Wellesley Hills, MA 02481
  • 32 Bobolink Rd, Wellesley Hills, MA 02481
    32 Bobolink Rd, Wellesley Hills, MA 02481
    32 Bobolink Rd, Wellesley Hills, MA 02481
    /42

    $1,490,000

    Open Sun 11AM - 12:30PM $39K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,218 Sq Ft

    32 Bobolink Rd, Wellesley Hills, MA 02481

    Meticulously updated and turnkey move in!32 Bobolink Rd combines classic charm with modern conveniences. Recent improvements including a new roof, updated HVAC systems & interior upgrades,unbeatable location close to all the Wellesley top schools, parks, shopping, and commuter routes.Bright and spacious raise ranch house which located on a quiet street. Gleaming hardwood floors , open concept

    Key Kuen Ho Blue Ocean Realty, LLC

    32 Bobolink Rd, Wellesley Hills, MA 02481
  • 37 Oakland St, Wellesley, MA 02481
    37 Oakland St, Wellesley, MA 02481
    37 Oakland St, Wellesley, MA 02481
    /37

    $2,480,000

    Open Sun 12PM - 1:30PM $118K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,600 Sq Ft

    37 Oakland St, Wellesley, MA 02481

    STUNNING NEW-CONSTRUCTION-QUALITY RENOVATION! Completely gut-renovated 5BR/4.5BA home featuring an open, sun-filled floor plan, designer finishes, and a chef’s kitchen with premium appliances. Bright sunroom, spacious living areas, and a fully finished lower level ideal for a family room, gym, or guest space. A professionally installed perimeter French drain system ensures a dry basement. Enjoy

    John Saleh Centre Realty Group

    37 Oakland St, Wellesley, MA 02481
  • 77 Cedar St, Wellesley Hills, MA 02481
    77 Cedar St, Wellesley Hills, MA 02481
    77 Cedar St, Wellesley Hills, MA 02481
    /39

    $2,150,000

    • 5 Beds
    • 3.5 Baths
    • 3,704 Sq Ft

    77 Cedar St, Wellesley Hills, MA 02481

    Young & beautifully crafted, this exceptional home offers the perfect blend of modern luxury & everyday convenience. Designed for effortless living and entertaining, the sun-filled open floor plan is anchored by a stunning chef’s kitchen featuring high end appliances, walk in pantry & expansive countertops with generous gathering spaces that flow seamlessly into the inviting family room, LR &

    The Lara & Chelsea Collaborative Coldwell Banker Realty - Wellesley

    77 Cedar St, Wellesley Hills, MA 02481
  • 144 Washington St, Wellesley Hills, MA 02481
    144 Washington St, Wellesley Hills, MA 02481
    /2

    $3,500,000

    New Construction
    • 5 Beds
    • 5.5 Baths
    • 5,800 Sq Ft

    144 Washington St, Wellesley Hills, MA 02481

    Beautiful New Construction in desirable Wellesley Hills near Warren Park. The inviting front porch & enhanced driveway w/cobblestones sets the tone of the home's warmth & craftsmanship. It's 5,800 sq.ft. of living over 4 levels. No detail has been overlooked, from the layout, custom built-ins, coffered ceiling & shiplap accents. The Chef's kitchen has Thermador appliances, large center island and

    Patricia Bradley Rutledge Properties

    144 Washington St, Wellesley Hills, MA 02481
Massachusetts Norfolk County Wellesley Wellesley Hills

Real Estate & Homes for Sale in Wellesley Hills, Wellesley

Why Live in Wellesley Hills
Wellesley Hills is a neighborhood characterized by its early 20th-century architecture, featuring grand Colonial Revivals, Tudor Revivals, Cape Cods, and Garrison-style homes. Newer constructions are also present, often replacing older structures due to limited land availability. The area is known for its larger lot sizes, ranging from a quarter acre to 1 acre. Residents, including many finance, banking, and biotech executives, enjoy a community with abundant walking trails and parks such as Centennial Park and the 2.5-mile Fuller Brook Path. In winter, local hills and ponds become popular spots for ice skating and sledding. The Wellesley Country Club, with its 18-hole golf course, racquetball courts, and outdoor pool, serves as a key recreational and social hub. Commerce is centered along Washington Street, home to independent bakeries, restaurants, and shops, including the repurposed Wellesley Hills rail station now housing Caffè Nero. Whole Foods Marketplace and Linden Square offer additional retail options. Community events like Wellesley’s Wonderful Weekend and various block parties foster a strong sense of community. The neighborhood is well-connected, with the Wellesley Hill train station providing MBTA commuter rail access to Boston, and bus routes via the MetroWest Regional Transit Authority. Boston and Logan International Airport are less than 20 miles away. Students attend highly rated Wellesley Public Schools, including Joseph E. Fiske Elementary, Otho L. Schofield Elementary, Wellesley Middle School, and Wellesley High School. Local higher education institutions include Wellesley College, Babson College, and Mass Bay Community College.
Learn more about living in Wellesley Hills

Wellesley Hills Home Prices vs. Nearby Wellesley, MA Neighborhoods

Wellesley Hills Wellesley Farms Weston The Flats
Median Home Price
$2,274,500
$2,295,000
$2,795,000
$2,599,000
Median Sale Price
$2,325,000
+22% YoY
$2,050,000
-5% YoY
$2,480,000
+3% YoY
$2,575,000
+11% YoY
Median Single Family Price
$2,325,000
$2,327,500
$2,700,000
$2,640,000
Median Townhouse Price
$1,612,000
--
$881,250
$1,475,000
Median Condo Price
--
$1,100,000
$850,000
$1,379,000
Total Active Listings
10
4
44
4
Market Conditions
3 Months of Supply
Seller's Market
2 Months of Supply
Seller's Market
4 Months of Supply
Seller's Market
1 Months of Supply
Seller's Market

Frequently Asked Questions

Is Wellesley Hills a good place to live?
Wellesley Hills is a good place to live. Wellesley Hills is considered car-dependent and bikeable with minimal transit options. Wellesley Hills is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. It has a median age of 42. The average household income is $217,185 which is above the national average. College graduates make up 84.9% of residents. A majority of residents in Wellesley Hills are home owners, with 25% of residents renting and 75% of residents owning their home. A local real estate agent serving Wellesley Hills can help you decide if this neighborhood is the right one for you. Learn more on our Wellesley Hills neighborhood guide.
Is Wellesley Hills, MA a safe neighborhood?
Wellesley Hills, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Wellesley Hills?
The median home price in Wellesley Hills is $2,274,500. If you put a 20% down payment of $454,900 and had a 30-year fixed mortgage with an interest rate of 6.49%, your estimated principal and interest payment would be $11,490 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $492K a year to afford the median home price in Wellesley Hills. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Wellesley Hills is $217K.
What are the best public schools in Wellesley Hills?
The best public schools that serve Wellesley Hills are:
What are the best private schools in Wellesley Hills?
The best private schools that serve Wellesley Hills are:
  • Fessenden School has an A+ Niche grade, a student teacher ratio of 5:1 and an average review score of 4.8.
  • Dana Hall School has an A+ Niche grade, a student teacher ratio of 6:1 and an average review score of 4.3.
  • Fusion Academy Newton has a B+ Niche grade, a student teacher ratio of 2:1 and an average review score of 4.0.
What are the most popular zip codes in Wellesley Hills, Wellesley, MA?
The most popular zip codes in Wellesley Hills, Wellesley, MA include 02481, 02494, 02462, 02468 and 02464.
What are the most popular neighborhoods near Wellesley Hills, Wellesley, MA?
The most popular neighborhoods near Wellesley Hills, Wellesley, MA are Waban, Wellesley Farms, Newton Upper Falls, Cliff Estates and Auburndale.
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