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62 Cypress Unit 1, Brookline
$850,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73570551 MLS ⋅ 1,135 SqFt.
PRICED TO SELL!! PRICE BELOW TOWN ASSESSED VALUE. RARE 2-UNITS-IN-1 CONFIGURATION | PRIME BROOKLINE VILLAGE LOCATION!! INVESTOR & MULTIGENERATIONAL OPPORTUNITY!Unlock the ultimate flexibility at 62 Cypress St #1, a uniquely structured property featuring two separate apartments contained under one deed: a charming 1-bedroom unit and a self-sufficient studio. Spanning 1,135 square feet of versatile living space, this property is perfect for investors looking to maximize rental income, buyers seeking a multigenerational living setup, or owner-occupants wanting to live in one side while renting out the other to pay down the mortgage. Alternatively, the layout offers the seamless potential to combine both spaces into a 2-bedroom, 2-bathroom residence. Steeped in classic 1895 Brookline charm, the property boasts stunning period details including soaring high ceilings, elegant moldings, tall wood pocket doors, oversized windows, and original hardwood flooring throughout. The primary apartment features a sun-drenched living room with a bay window, a fully renovated eat-in kitchen with granite countertops and stainless appliances, a comfortable spacious bedroom, and a convenient in-unit washer and dryer. The adjacent studio apartment functions perfectly as an independent guest house, passive income stream, or private home office, complete with its own large bay window, full bathroom, and a functional kitchenette. Condo includes 1 parking space and a pet-friendly association. Perfectly situated in the heart of Brookline, you are just steps away from Brookline Village, the Green Line T-station, Emerson Park, and Brookline High School. Enjoy an easy commute or quick access to the world-renowned Longwood Medical Area, local shopping, dining, and major employment centers. This is an incredibly rare opportunity to secure an asset with immediate equity growth and unparalleled lifestyle options in one of Greater Boston's most desirable communities!

62 Cypress Unit 1, Brookline

17 Chesham Road, Brookline
$3,195,000
6 Beds ⋅ 6 Baths ⋅ UNDER AGREEMENT Status ⋅ 73570431 MLS ⋅ 5,487 SqFt.
This stunning Fisher Hill home is surrounded by spectacular gardens and offers over 5,400 square feet of living space. Featuring 6 bedrooms, 5 full baths, and 1 half bath, the home welcomes you with a expansive foyer and curved staircase. The warm and inviting living room boasts floor-to-ceiling windows, a fireplace, and French doors opening to the loggia. The dining room features a fireplace and bowed window overlooking the gardens. An expansive eat-in kitchen includes a center island and upholstered seating area. A bookshelf lined family room and half bath complete the first floor.Upstairs, the grand primary suite offers a walk-in closet, en-suite bath, and shared balcony with the second bedroom. There is a second bedroom on this floor that also includes an en-suite bath and the additional additional bedrooms share a faull bath. The third floor provides extra bedrooms and ideal home office space plus there is a full bath on this floor. The third floor also offers a large walk-in closet that is perfect for additional storage..Additional highlights include a finished basement with exercise room, office, and full bath, plus a two-car garage and beautifully landscaped yard and stone patio. Ideally located for easy access to Washington Square and the C and D line of the T. Convenient to the Runkle Elementary School, Whole Foods, Trader Joes and the shops and restaurants of Coolidge Corner.

17 Chesham Road, Brookline

16 Harris St, Brookline
$2,700,000
6 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73565926 MLS ⋅ 4,281 SqFt.
A compelling opportunity in Brookline’s F-1.0 Three-Family zoning district. This well-located property is currently configured as a three-family residence and offers exceptional potential for investors, developers, or an owner-occupant looking to create value in one of Brookline’s most desirable neighborhoods. Owned and loved by the same family for many decades, this distinctive property offers generous layouts, period character, multiple outdoor spaces, a 2-car garage, driveway parking, in a location that is convenient to public transportation, shops, restaurants, and neighborhood amenities. Unit 1 is a bi-level 4 bed, 2 bath residence featuring approximately 9'5" ceilings on the first floor, three fireplaces, multiple decks, generously sized bedrooms, and in-unit laundry hookup. The scale and flexibility of this unit provide an excellent foundation for future improvement and personalization. Unit 2 is a charming 1 bed, 1 bath apartment with just over 9 foot ceilings, a generous sized bedroom with: fireplace, bay window and plenty of wardrobe room. The kitchen features ample cabinetry, and gas connection for a range. A spacious bathroom with shower/tub combination add to the appeal. Unit 3, uniquely offers a flexible 1- 2 bedroom layout with plenty of character. The bedroom and living areas can be configured to accommodate different living arrangements, while an additional sitting area provides an ideal home office or flex space. For investors, the property’s three-unit configuration, substantial square footage, parking, outdoor space, and prime Brookline location create multiple avenues for maximizing the property’s potential. The existing layouts provide a strong starting point for thoughtful renovation, modernization- a canvas of limitless scope. Commuting is convenient with the 66 bus and Green Line C/D branches nearby. Additional features include basement washer/dryer hookups. 16 Harris is a rare opportunity to acquire a character-rich Brookline multifamily in a highly desirable location.

16 Harris St, Brookline

52 Clinton Road, Brookline
$2,999,000
4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73565107 MLS ⋅ 3,265 SqFt.
Located on coveted Fisher Hill, this charming residence set on 14,550 square feet of beautifully landscaped grounds, offers thoughtfully designed modern updates, newer systems, and the convenience of an attached garage. The gracious main level features a welcoming living room with fireplace, formal dining room, powder room, and a chef’s eat-in kitchen featuring custom cabinetry outfitted with a Thermador gas cooktop and warming drawer, GE Monogram double ovens, two Bosch dishwashers, two sinks, and a Sub-Zero refrigerator. The kitchen opens to a spacious, sun-filled family room with skylights and direct access to the lush, private backyard. A flag stone patio and gas hookup for grilling create an ideal setting for relaxed indoor-outdoor living. The second level features a generous primary suite with a newly renovated en-suite bath, complete with luxurious heated radiant floors and a skylight, along with three generous closets. Three additional well-proportioned bedrooms with substantial closet space and a full bath complete this level. The finished lower level provides versatile flex space for a gym, office/guest accommodations, playroom/den, along with a full bath, laundry area with refrigerator/freezer, and extra storage, all with 1- car garage access and additional 2 outdoor spaces. Ideally situated near Runkle School, Brookline High School, the Longwood Medical Area, Chestnut Hill Reservoir, and the MBTA Green Line C and D branches, with easy access to nearby shops, restaurants, and Route 9.

52 Clinton Road, Brookline

60 Marshal St Unit 4, Brookline
$580,000
1 Beds ⋅ 1 Baths ⋅ UNDER AGREEMENT Status ⋅ 73564879 MLS ⋅ 828 SqFt.
SUBSTANTIAL PRICE REDUCTION! Oversized 1 Bed condo (828 square feet) in one of Brookline's most desirable locations; situated between Coolidge Corner & Longwood. This unit boasts an expansive floor plan with a favorable layout and loads of great features. The vast layout boasts a large entryway, spacious living room with towering ceiling height and bay windows, separate dining space, PLUS a separate office nook perfect for a home office. The bedroom can comfortably fit a queen bed plus additional furniture and the separate kitchen offers comfortable space for cooking and food prep. This is a true floor-thru layout, with front to back (east to west) exposure allowing for great natural light. There is CENTRAL AIR, WASHER / DRYER in unit, dishwasher/disposal, multiple walls of exposed brick, lots of closet space, and an incredibly LOW CONDO FEE of only $223 includes heat and hot water. The building has recently replaced the roof (July 2025), upgraded the electrical service to 400AMP (August 2025), & re-pointed the exterior masonry (July 2025). No upcoming assessments or large projects planned. Built new in 1997, this unit has been incredibly well-maintained and is in excellent / turnkey condition. There is a private entrance with access to an exclusive patio and shared yard space. A+ Location! Located one block to the C Line, several blocks to the D Line, surrounded by parks, commerce, and endless dining & entertainment options. Coolidge Corner, Audubon Circle, Kenmore Square, Fenway, and Longwood all within close proximity. 88 Walk-Score. This unit will surprise you with how much natural light it receives and how open & airy it is. Do not skip this one - you will be pleasantly surprised when you see it in person.

60 Marshal St Unit 4, Brookline

37-39 Beaconsfield Road, Brookline
$2,999,000
9 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73561142 MLS ⋅ 4,600 SqFt.
RENOVATED Side-by-Side 2-FAMILY in BROOKLINE near Washington Square. Townhome Style Layouts, Each Unit has a Private Entry & Each home enjoys Private Outdoor Space, Deck + Terrace + Patio. Central A/C with separate HVAC. The Large DRIVEWAY, holds 3 Car Parking in Tandem. Strong Rental History! One Unit (#37) is 1600SF, 4BR/2BA, located on the right side and can be "Owner Occupied" while you collect rent ($7,225/month) next door at #39 w/Lease thru 8/31/27. That Penthouse Duplex is Spacious & Renovated with 5 Bedrooms/3 Bathrooms. The Living/Dining showcase a Wall of Windows, overlooking a Tree-lined Beaconsfield Road. Each room is Bright & Sundrenched across 3000 Square Feet. The finishes throughout are Condo-Quality! Beautiful Hardwood Floors, Central A/C, In-Unit Washer/Dryer. Entering the Kitchen, The Delighted Chef in YOU feels at home with a Gas Cooking & High-End Appliances like VIKING + SUB-ZERO. On the left side, #39 has generously-sized Bedrooms with a WOW Primary Suite --Walk in Closet--Primary Bathroom. Cherry Wood Cabinets surround a Double Vanity. The Cherry on Top? The Vanity has Custom Storage on ALL sides...Left | Right | Center...PRIME LOCATION with Access to Washington Square's Restaurants, Botique Shops and Star Market. Just minutes to the Beaconsfield Green Line (T) station, D Line + C Line. Only 10 min walk to Brookline High School or The Brookline Reservoir. Beaconsfield is a side street, making this an exceptional Investment Opportunity.

37-39 Beaconsfield Road, Brookline

811 Heath St Unit Rear, Brookline
$2,100,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73560438 MLS ⋅ 3,193 SqFt.
TWO CAR GARAGE: This exceptional contemporary townhome offers 3,193 square feet of sophisticated living space in the heart of Chestnut Hill. Located in the highly desirable Brookline school district, this four-bedroom, four-and-a-half-bath residence combines refined contemporary design, premium finishes, and the comfort of single-family living with the convenience of condominium ownership.Bathed in natural light from oversized black-framed windows, the open-concept main level features 8-inch white oak hardwood flooring, soaring ceilings, and a beautifully appointed chef's kitchen with custom cabinetry, quartz countertops, premium stainless steel appliances, a six-burner Bosch gas range, and an oversized center island overlooking the dining and living areas. Sliding glass doors open to a private patio and fenced yard, creating seamless indoor-outdoor living, while a stylish tiled powder room completes the main level.The second level features two spacious en-suite bedrooms, including a luxurious primary suite with a custom walk-in closet and spa-inspired bath featuring elegant tilework and a frameless glass shower. The top level offers two additional en-suite bedrooms, a striking glass-enclosed office, and a dedicated laundry room.Additional highlights include designer lighting, a tiled mudroom with custom built-ins, abundant storage, and two assigned heated garage parking spaces.Moments from The Street Chestnut Hill, Chestnut Hill Square, Hammond Pond Reservation, Skyline Park, Route 9, Longwood Medical Area, and downtown Boston. Never occupied, this extraordinary residence offers a rare opportunity to own a turnkey luxury home in one of Brookline's most sought-after neighborhoods.

811 Heath St Unit Rear, Brookline

60 Babcock St Unit 53, Brookline
$699,000
1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73553757 MLS ⋅ 768 SqFt.
Beautifully renovated 5th-floor condo in the heart of Coolidge Corner with spectacular, unobstructed views of the Boston skyline and gorgeous sunrises. This spacious, sun-filled 1-bedroom home features floor-to-ceiling windows, a large private balcony, and desirable southeast exposure that fills the space with natural light. The thoughtfully updated interior includes a contemporary kitchen with stainless steel appliances and breakfast bar, an inviting dining room area, a large bedroom with walk-in closet, a newly renovated bath with glass shower enclosure, new Bosch washer/dryer, air conditioning (mini-splits) in living room and bedroom, recessed lighting, beautiful engineered hardwood floors, and motorized window shades. The private balcony is perfect for morning coffee, al fresco dining, and herb/flower gardening. Professionally managed building with recently upgraded heating system, renovated common areas, modernized elevators, secure lobby with electronic entry, package room, additional storage, and bicycle racks in the garage. Garage parking, plus guest parking. Landscaped grounds with mature plantings and benches tucked amongst the gardens. Ideally located near shops, restaurants and cafés, Trader Joe's, several parks, schools, universities, Green Line (B & C), and the Longwood Medical Area. This elegant move-in ready home offers an outstanding opportunity to own in one of Brookline's most sought-after neighborhoods.

60 Babcock St Unit 53, Brookline

50 Green Street Unit 401, Brookline
$949,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73553528 MLS ⋅ 1,086 SqFt.
Turnkey Treasure in the Heart of Coolidge Corner. Welcome to this beautifully maintained top-floor corner residence, ideally situated on a picturesque one-way, tree-lined street with a dedicated bike lane and a charming neighborhood park just outside your door. Located in the heart of highly sought-after Coolidge Corner, this exceptional home offers the perfect blend of convenience, comfort, and timeless appeal. Bathed in natural light from its desirable southern exposure, the residence enjoys breathtaking sunrise and sunset views with unobstructed vistas throughout the day. The thoughtfully updated kitchen features new stainless steel appliances, granite countertops, and abundant cabinetry, while gleaming hardwood floors—professionally Bona® refinished—add warmth and elegance throughout. Meticulously cared for by the same owner-occupant since 1978, this move-in-ready home is in outstanding condition. Additional highlights include premium custom window treatments, generous closet space, and one deeded parking space (currently assigned as #60). Residents enjoy an elegant lobby, a beautifully maintained community, and access to an Olympic-sized outdoor swimming pool. This is a rare opportunity to own a turnkey home in one of Brookline’s most desirable neighborhoods, just moments from renowned restaurants, cafés, boutique shopping, public transportation, and everything Coolidge Corner has to offer.

50 Green Street Unit 401, Brookline

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