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$2,885,000
5 Beds 4 Baths ACTIVE Status 73507050 MLS 4,110 SqFt.
Located on one of Wellesley’s most coveted roads in Cliff Estates, 100 Albion is a beautifully appointed pillared white Colonial set on .77 acres of professionally landscaped grounds. Blending timeless architecture with modern living, the main level offers a gracious fireplaced living room with a large picture window, an elegant dining room, a private office, and an expansive kitchen centered around a large island. These spaces flow seamlessly into a spacious fireplaced family room with custom cabinetry and out to a brand-new deck ideal for indoor/outdoor entertaining. The first floor also includes a well-placed laundry room with a full bath. Upstairs are five bedrooms, including a serene primary suite with a walk-in closet, along with four additional bedrooms and two full baths. The finished walk-out lower level features a full bath and bar, providing versatile living space. Exceptional curb appeal, a circular driveway, and beautifully landscaped grounds complete this impressive home.

100 Albion Rd, Wellesley

$2,325,000
5 Beds 4 Baths UNDER AGREEMENT Status 73506000 MLS 2,840 SqFt.
Set in Wellesley’s sought after Dana Hall neighborhood, 11 Sterling Road blends timeless charm with modern living on .57 acres of private, beautifully landscaped grounds. This 5-bedroom home offers 3 full baths and 1 half bath, with an open floor plan tailored for today’s lifestyle. Sun-filled interiors feature a fireplace living room, formal dining room with large picture windows, and a welcoming den/family room with its own fireplace-ideal for both everyday living and entertaining. The kitchen, equipped with stainless steel appliances, flows seamlessly into the main living areas. The second floor includes a spacious primary suite with full bath and three additional bedrooms and another full bath, while the third floor provides a private ensuite fifth bedroom—perfect for guests or a home office. A finished lower level adds versatile space for recreation, fitness, or work. Ideally located near town, schools, and commuting routes. Don't miss this opportunity to make this home your own!

11 Sterling Rd, Wellesley

$1,239,000
3 Beds 3 Baths UNDER AGREEMENT Status 73503725 MLS 3,129 SqFt.
Come see the Best of Everything! Over 3000 sq ft, soaring ceilings, 2 staircases, gracious formal and casual living & dining, updated light-filled kitchen, butler’s pantry, first floor laundry, up to five sleeping spaces, tranquil primary ensuite, beautiful hardwood floors, period details thru-out. Two porches, mature plantings, 2 car garage and EV charging station complete this classic gem, just steps to schools, shopping & train. Enjoy the space of a multi-million dollar home for the price of a condo. Most convenient Worcester Street address. Great access to and from town on side roads and new traffic signals get you in and out of the driveway with ease. Best value in Wellesley!

642 Worcester St, Wellesley

$2,250,000
8 Beds 5 Baths ACTIVE Status 73503039 MLS 5,559 SqFt.
Ideally located in the heart of Wellesley Center, 9–11 Hampden Street is a rare offering of gracious proportion, charm and timeless detail. With nearly 5,600 sq. ft. of living space across three sun-splashed finished floors, this stately residence offers 8 bedrooms and versatile living areas awaiting a discerning buyer’s vision. Sited on .37 acres, with a freshly painted interior, it is equally compelling as a grand single-family home or as an investment with its current 2-family configuration. Rich in history, the property was long associated with Helen Temple Cooke, pioneering educator and head of the Dana Hall School from 1899-1955. Currently owned for a second time by Dana Hall, the home blends historic character with an unrivaled in-town location - just a block to the train, shops, restaurants, and the beloved Brook Path. A unique opportunity to create a signature residence or phenomenal addition to your investment portfolio in one of Wellesley’s most coveted neighborhoods!

9-11 Hampden Street, Wellesley

$2,250,000
8 Beds 6 Baths ACTIVE Status 73503038 MLS 5,559 SqFt.
Ideally located in the heart of Wellesley Center, 9–11 Hampden Street is a rare offering of gracious proportion, charm and timeless detail. With nearly 5,600 sq. ft. of living space across three sun-splashed finished floors, this stately residence offers 8 bedrooms and versatile living areas awaiting a discerning buyer’s vision. Sited on .37 acres, with a freshly painted interior, it is equally compelling as a grand single-family home or as an investment with its current 2-family configuration. Rich in history, the property was long associated with Helen Temple Cooke, pioneering educator and head of the Dana Hall School from 1899-1955. Currently owned for a second time by Dana Hall, the home blends historic character with an unrivaled in-town location - just a block to the train, shops, restaurants, and the beloved Brook Path. A unique opportunity to create a signature residence or phenomenal addition to your investment portfolio in one of Wellesley’s most coveted neighborhoods!

9-11 Hampden Street, Wellesley

$1,595,000
6 Beds 4 Baths UNDER AGREEMENT Status 73502238 MLS 3,447 SqFt.
Wonderful opportunity in the heart of the Poet's neighborhood, this expansive Tudor Colonial blends timeless charm with modern comforts. Thoughtfully updated throughout, this home boasts soaring ceilings, spacious rooms and a flexible floor plan. Gracious formal living room with stone fireplace flows through to well appointed dining room. Light and bright eat in kitchen with stainless steel appliances opens to the large level lot perfect for indoor/outdoor entertaining. Family room and wonderful sunroom / play space offer many options for today's living. Upstairs there are four corner bedrooms and renovated full bath. The third floor allows for either two additional family bedrooms or private work from home space. The separate entrance makes it a fantastic space for an in law or au pair suite. Finished lower level with home gym, full bath and ample storage. Prime location near shops, restaurants and easy commuting to Mass Pike and the T. Just Minutes from Warren playground.

225 Walnut St, Wellesley

$1,699,000
5 Beds 4 Baths ACTIVE Status 73500976 MLS 2,267 SqFt.
Located in the Dana Hall neighborhood of Wellesley, this expansive 5-bedroom, 4-bath home offers a highly desirable and flexible layout, complemented by a detached guest suite, ideal for extended family, an au pair, or visiting guests. The beautifully updated kitchen features ample storage, quality finishes, and seamless flow to sun-filled living spaces, creating an inviting setting for everyday living and casual gatherings. Generously sized bedrooms and a clean, well-lit basement round out the interior. A sparkling pool anchors warm-weather entertaining, while the expansive deck overlooking the large, flat, fenced-in yard provides generous space for grilling, dining, lounging, and hosting. Mature landscaping enhances privacy and curb appeal, and the location offers close proximity to top-rated schools, shops, commuter routes, and recreation. 29 Cottage Street delivers the complete package—flexible living, beautiful indoor-outdoor spaces, and a layout that supports every stage of life.

29 Cottage St, Wellesley

$3,500,000
5 Beds 6 Baths ACTIVE Status 73499362 MLS 5,800 SqFt.
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 sunny eat-in area that abuts a spacious family room. Flexible first floor w/office or living room & a formal dining room. 5 bedrooms, including a Primary Suite w/walk-in closet & spa-like bath. The expansive lower level has a full bath offering plenty of space for a playroom & gym. The oversized mudroom w/custom built-ins, easy access to the stone patio will not disappoint. A 2 car garage w/overflow parking space, making coming & going a breeze. It's an ideal commuter location near the Hills Train and short distance to shops, restaurants, & Hills Library. Delivery date is mid-June!

144 Washington Street, Wellesley

$5,695,000
5 Beds 7 Baths ACTIVE Status 73499334 MLS 9,400 SqFt.
Once in a lifetime opportunity to own in Wellesley's most coveted premier historic location, Pond Road. Featuring the finest custom craftsmanship throughout, professionally engineered mechanical systems, smart house and professionally designed ultra high end finishes. Over 9400 sq ft of living space on 3 floors. The floor plan everybody wants with a 1200 sq ft great room and over 10 foot ceilings. Oversized mudroom and pantry. First floor includes white oak herring bone hardwoods. 2nd floor ceilings 14-20 feet! An incredible main suite. All bedrooms en-suite with walk-in closets. Plus a 2nd floor lounge room or incredible guest suite. Lower level is unprecedented with 17 ft ceiling in 1/2 court basketball/ rec room (size of space also work for squash) with viewing room including wet bar. Theatre/media room with additional wet bar plus a gym with full bath including steam shower. Large flat yard. Close to Wellesley trails and town center.

196 Pond Road, Wellesley

$1,595,000
3 Beds 3 Baths ACTIVE Status 73499017 MLS 3,012 SqFt.
Wake up to sparkling water views from every room. Sip morning coffee and enjoy the wildlife from your deck. River views can be enjoyed from nearly every room and are especially striking from the expansive glass-enclosed sunroom where the landscape changes with the season. Recent upgrades include a new roof, HVAC, full interior and exterior painting, windows, doors, and more. The open, flexible layout is ideal for entertaining, creative living, and working from home. Set among lush perennial gardens, this unique home offers abundant privacy and a peaceful natural backdrop. A truly special home in an extraordinary natural setting. Ideally located with easy access to Wellesley Center and minutes from South Natick, Elm Bank Reservation, and the historic Bacon Free Library.

30 S River St, Wellesley

$4,150,000
5 Beds 4 Baths UNDER AGREEMENT Status 73498043 MLS 5,074 SqFt.
Set in one of Wellesley’s most elite and sought-after neighborhoods, this quintessential Colonial blends timeless architecture with impeccable modern updates. Thoughtfully and beautifully renovated by a highly regarded architect and premier builder, the home showcases exceptional craftsmanship and refined design throughout. The private backyard retreat is ideal for both relaxation and entertaining, featuring a stunning bluestone patio, elegant walkways, and extensive masonry that extends to a beautifully crafted paver driveway. Perfectly positioned across from coveted Rockridge Pond, residents enjoy year-round access to scenic trails, kayaking and canoeing in warmer months, and picturesque ice skating in winter. A rare opportunity to own a classic home in an exceptional setting where natural beauty and sophisticated living come together.

33 Hundreds Cir, Wellesley

$1,100,000
3 Beds 3 Baths ACTIVE Status 73497359 MLS 2,165 SqFt.
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 appliances, ample storage and breakfast bar and opens to a large rear deck, perfect for entertaining.  Upstairs boasts  a large en-suite Primary bedroom, two additional bedrooms, another full bath along with an office/den bonus  space. There are plenty of custom built-ins, cabinets and quaint nooks that make this an adorable gem of a home.  The acreage is combined lots 6 & 6R and offers a half acre of privacy or possible room to grow. The home needs some exterior and basement improvements to reimagine it to your dream!  Terrific location, moments to Fiske elementary school & easy access to Rt.9,128.

6 Willow Street, Wellesley

$2,149,000
4 Beds 4 Baths UNDER AGREEMENT Status 73494412 MLS 3,122 SqFt.
Step into a notable historic "Augustus Fuller" home-where timeless character meets modern living. This beautifully preserved and thoughtfully updated residence offers an exceptional opportunity to own a home rich in heritage while enjoying today's most sought after comforts.Historic charm is evident in every detail, with countless interior & exterior updates to ensure a lifestyle of ease & sophistication. The heart of the home features a newly renovated, sun-drenched kitchen that shines as a true centerpiece. Designed with both style & functionality in mind, it features bright finishes & ample cabinetry for an inviting atmosphere perfect for everyday living & entertaining alike. The second floor offers 4 beautiful bedrooms offering charming fireplaces, wood floors, 3 full bathrooms, a laundry area as well as spaces to be creative for your daily needs. The addition of a classic farmer's porch with fans & a copper roof graces the front of the home. WELCOME HOME!

122 Great Plain Ave, Wellesley

$999,900
2 Beds 2 Baths CONTINGENT Status 73494021 MLS 1,057 SqFt.
Beautifully crafted and brand new, this 24 unit condominium assoc. at The Albion features luxury living spaces with open floor plans, high-end finishes, and bordering green spaces. The Albion is the ultimate mix of contemporary design, and modern amenities, and is set in a prime location near Linden Square in Wellesley. This two-bedroom residence features 9’ high ceilings, hardwood floors, fireplace, quartz countertops, in-unit laundry, with washer and dryer and oversized energy-efficient windows providing wonderful natural sunlight. This is a corner unit with three lovely exposures. Parking space #35. The Albion is located approximately .5 miles from Linden Square and abuts Sprague Field. Town amenities are close by, offering residents the convenience and proximity to top-ranking public schools, many shops and restaurants, grocery stores, as well as multiple parks, public tennis courts, trails, and the commuter rail into Boston. Common area exercise and game room.

16 Stearns Unit 302, Wellesley

$1,945,000
4 Beds 4 Baths UNDER AGREEMENT Status 73491540 MLS 2,953 SqFt.
This charming 1937 Colonial is perfectly situated on a quiet cul-de-sac just moments from shops, restaurants, major highways, and the commuter rail, offering both convenience and neighborhood charm. With four finished levels of living space, this beautifully maintained home features nine spacious rooms, including four bedrooms, three full baths, and one half bath. The updated kitchen opens seamlessly to the living and dining areas, creating a bright and inviting layout ideal for everyday living and entertaining. A dedicated first-floor office provides the perfect space for working from home. The finished lower level offers additional flexible living space for a family room, gym, or playroom. Outside, enjoy a private fenced backyard with a patio, perfect for relaxing or hosting gatherings. Classic character blends effortlessly with modern updates in this warm and welcoming home, offering comfort, style, and a highly desirable location close to everything.

2 Woodlawn Oval, Wellesley

$1,625,000
3 Beds 4 Baths UNDER AGREEMENT Status 73490774 MLS 2,377 SqFt.
Perfection! This townhome functions as a single family while offering the ultimate in luxury, size and convenience. Large open floor plan with designer kitchen, large dining space and huge living area. Second floor main bedroom with large custom closet and gorgeous full bathroom with double sink. Two additional bedrooms with full bath. Laundry completes the second floor. Fully finished lower level with windows and full bath. Perfect space for family room and/or gym. All finishes selected by one of Wellesley's favorite interior designers. One garage space and one designated parking space plus ample parking for guests. Just a short distance to Linden Square with Tatte, Karma, The Cottage, Captain Marden's... Plus Roche Brothers, great stores, train and all schools close by! Not to be missed!!!

63 Oak Street Unit A, Wellesley

$1,747,200
2 Beds 3 Baths ACTIVE Status 73488987 MLS 1,792 SqFt.
2 garage parking spots included if offers by 5/31!!! Welcome to the ALBION! New Construction Wellesley’s newest luxury condominium building. This stunning 2-bedroom, den/office and 2.5-bath residence featuring soaring 9' ceilings and beautiful open views overlooking Sprague Field. The open-concept floor plan, showcases a high-end chef’s kitchen with center island, premium finishes, and all the bells and whistles—perfect for everyday living and entertaining. The warm and inviting living room is highlighted by a cozy fireplace. The spacious primary suite offers a walk-in closet and a spa-like bath designed for relaxation. The 2nd bedroom has outdoor access to a private balcony. In-unit laundry. Exercise & game rooms on 2nd & 3rd level. Within close proximity to vibrant Linden Square amenities including shopping and restaurants, & tennis & pickle ball courts at Sprague Field. Easy highway access. Please ask listing agent about the possibility of a second space.

16 Stearns Rd Unit 208, Wellesley

$4,950,000
7 Beds 8 Baths UNDER AGREEMENT Status 73488659 MLS 8,840 SqFt.
Spectacular Cliff Estates Colonial set on a majestic, private ¾ acre lot in one of Wellesley’s most coveted neighborhoods. Meticulously updated and expanded by renowned architect Patrick Ahern + KVC Builders, this exceptional residence blends timeless elegance, exquisite detailing and refined modern living. Designed for grand entertaining, the main level features a front-to-back living room w/a fireplace and French doors to a balcony overlooking beautifully landscaped grounds, a formal dining room, and a sunlit chef’s kitchen with dual islands, breakfast room and butler’s pantry. A gracious family room w/a fireplace and custom built-ins opens to a richly paneled study. The serene primary suite offers a fireplace, spa-like bath with soaking tub & private balcony. There are 6 additional bedrooms plus a finished walkout LL w/a media room, recreation spaces and an office. An extraordinary offering close to top schools, commuting routes, and Wellesley’s premier shops, dining and more!

65 Woodcliff Rd, Wellesley

$1,295,000
3 Beds 2 Baths UNDER AGREEMENT Status 73474490 MLS 1,743 SqFt.
Welcome to this lovingly maintained 3 BR home on a quiet cul-de-sac in Wellesley. The first floor offers a formal living room w/wood burning fireplace, formal dining room and a sun-splashed FR with vaulted ceiling, gas FP, AC and access to outdoor deck. The kitchen has updated, granite countertops, SS appliances and dining space. 1/2 BA completes the first floor. The 2nd floor has three bedrooms and a full bathroom with tub & shower. Hardwood floors throughout almost the entire house. The heated basement w/FP offers a playroom as is or the ability to finish and add additional living space. There is also rooms for a work area & home office,. The yard offers opportunities for gardening and a play set. Conveniently located to Rt 9, Mass Pike and 95. 2.6 miles to Wellesley Square, commuter train, shops and restaurants. Sunnyside Ave is assigned to the new Hardy School! A perfect starter home in desirable Wellesley!

16 Sunnyside Ave, Wellesley

$2,299,000
5 Beds 4 Baths UNDER AGREEMENT Status 73473045 MLS 3,398 SqFt.
5 bedroom home on Morses Pond with the most incredible water views. Swim, paddle board, kayak or fish from your own backyard. Large open kitchen family room with full picture windows offering stunning views of the pond. Kitchen with stainless appliances and large island. Dining room/sunroom with access to deck with more water views. Living room with fireplace and built-ins. First floor den. Main suite also focuses on water views with new bathroom as well as walk-in closet. 2 additional bedrooms on 2nd floor with another updated bath. Large office on the 2nd floor. 3rd floor with 2 additional bedrooms- one with Juliet balcony and 3rd full bathroom. Lower level perfect for storage plus playroom/ exercise area. NEW: boiler, wet bar, flooring, master bath, 2nd floor bath and powder room. Recent updates make this home ready to move right in. Enjoy peaceful living and enjoy this view all 4 seasons of the year.

31 College Road, Wellesley

$3,245,000
5 Beds 5 Baths ACTIVE Status 73472096 MLS 4,416 SqFt.
Incredible new construction opportunity in one of Wellesley’s most sought-after neighborhoods, ideally located within walking distance to the newly built John D. Hardy Elementary School and nearby Perrin Park. This exceptional home offers a fabulous floor plan featuring soaring ceilings, exquisite millwork, abundant natural light, and designer fixtures and finishes throughout. The first floor showcases a grand foyer, open-concept chef’s kitchen with breakfast area, fire-placed family room, formal dining room, and a versatile first-floor study or bedroom. The second level includes four beautifully appointed bedrooms, highlighted by a spacious primary suite, one en-suite bedroom, and a shared double vanity bathroom. The finished lower level provides flexible space for a gym, additional bedroom, and family room. A two-car garage with high ceilings, mudroom, stunning stone patio, and level backyard complete this remarkable property.

38 Parker Rd, Wellesley

$1,285,000
4 Beds 3 Baths UNDER AGREEMENT Status 73469533 MLS 2,150 SqFt.
Rare opportunity to get into the Town of Wellesley. Situated on an oversized 26000 sqft lot on a cul-de-sac with potential for expansion.This well-maintained 4 Bedrooms, 2 1/2 bath home is in move-in condition. The main level has gleaming hardwood floors throughout, a master bedroom with an updated en-suite bath, and two good-sized bedrooms with shared updated full bath. New kitchen with SS appliances and granite counter tops and access to rear deck overlooking level backyard. Living room with fireplace and formal dining area complete the main floor. The fully finished ground level is sunny and bright, with a separate entrance and “mud-room” area and a bedroom with an updated half-bath, fireplace, and built-in shelving/storage. The large open floor plan provides great flexibility of use for an office, gaming lounge, work-out and entertainment room. Easy access to commuter rail, 95, Rt. 9, schools, parks, shopping and restaurants and Babson and Wellesley and Mass Bay colleges.

96 Washburn Avenue, Wellesley

$3,695,000
6 Beds 5 Baths PRICE CHANGED Status 73469127 MLS 6,990 SqFt.
Located in the Country Club neighborhood on 1.15 acres, overlooking Wellesley Country Club greens, with sweeping scenic golf course views. Renovated 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, dining room, home office with separate entrance w/full bath (or 6th bedroom). Primary suite with vaulted ceilings and radiant bathroom, 4 additional bedrooms (two ensuite), 4th bedroom access to third-floor game room. The finished lower level features a large billiards/family room, gym, workshop, mudroom & storage. Bluestone patio and wraparound deck capture panoramic views, spectacular sunrises and sunsets, fruit trees and a 19th-century unfinished barn with electricity and water & a fenced in paddock. Abutts conservation land, 2 car garage, cobblestone parking, stoned walls, can be sold furnished.

151 Oakland Street, Wellesley

$3,400,000
10 Beds 9 Baths ACTIVE Status 73445436 MLS 10,318 SqFt.
Rare Investment Opportunity in the Heart of Wellesley Square! Offered for the first time in almost 80 years, this exceptional TWO BUILDING/multi-family property is a rare find in one of Metro Boston’s most desirable communities. Situated on a quiet street just steps from vibrant Wellesley Square, this unique offering includes two buildings with a total of 7/8 units, providing excellent long-term income and countless possibilities for the savvy investor or owner-occupant. Live in one unit and let the other units work for you, or hold as a high-performing rental property with significant upside. This is an excellent opportunity to own in a prime Wellesley location — enjoy restaurants, boutique shops, the Commuter Rail, Wellesley College, and the Wellesley Library. Enjoy unbeatable access to Routes 16, 9, 95, and the Mass Pike, making commuting and travel effortless. Whether you're looking to invest, convert, or plant roots in a world-class community, this property delivers!

5-7 Abbott Street, Wellesley

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