Fabulous opportunity to own a multi-family in Watertown's desirable East End/Oakley CC neighborhood! Situated on a beautiful tree-lined street, this sprawling two-family offers over 3,000 square feet of living space, charming period details, and endless sunlight. The first-floor unit had been updated in the last 10 years and features a gracious fire-placed living room, dining room with original built-ins, two spacious bedrooms as well as rear sunroom perfect for a home office, newer kitchen and bath, and newer windows. The second floor which is ready for your own personal touches offers the same layout plus two additional bedrooms on the 3rd floor, as well as a large unfinished attic space with great expansion potential or adding a second bath. Both units feature gorgeous original woodwork, hardwood flooring, wood-burning fireplaces, built-ins & pantry space, high ceilings, decks and natural light. Large unfinished basement with high ceilings, one car garage and 3+ driveway parking. Incredible opportunity for owner-occupants, investors, multi-generational living or developers looking to do a condo-conversion in a prime neighborhood. Vibrant East Watertown location near Arsenal Yards, shops, restaurants, green space and all that Watertown has to offer! Commuter-friendly, easy to Boston/Cambridge and right down the street from the 73 bus to Harvard Square and the Red Line. Must see!
OPPORTUNITY KNOCKS - ATTN SAVVY INVESTORS & OWNER OCCUPANTS - Rare opportunity to build equity quickly in this classic New England 2 family style home. RARE WATERFRONT HOME in exceptional location, overlooking the Charles River and just a stone's throw from the Watertown Boat Yard. Fabulous area especially for those who enjoy being outdoors in nature - including water sports/recreation such as kayaking and boating or biking/walking/jogging alongside the Charles. Either way, you have direct access to both, just steps from your front door. Although you'll have a bit of updating to do, some major items have already been taken care of. This includes a new roof (2026), new water heaters for both units (2026), new plumbing in both baths including new stack (2026), refinished flooring in unit 2, both Burnham heating units have been serviced recently and are in good working order. Each unit gets 2 tandem off street parking, including 1 garage spot EACH. Easy commuter access to Harvard/Cambridge, downtown Boston & Brighton. Leave the car, take the bike along the Charles River bike path, minutes to the New Arsenal Yards for shopping and dining. Great layouts, sunroom/office area overlooking the Charles, beautiful decorative fireplaces in each unit, on a corner lot with outstanding parking options are just some of the core features adding to the untapped potential of this home.
Classic 1925 two-family in East Watertown, on a quiet block between Mount Auburn Street and Belmont Street, with hardwood through both floors under high ceilings, deep moldings and built-in china cabinets, and enclosed sunporches stacked front and back that keep every room bright. The first floor has eight rooms, two bedrooms, a full bath, formal dining with a corner built-in, an eat-in kitchen with a butler's pantry. The second floor has three bedrooms, a renovated bath, living and dining opening through original French doors, a sunroom, and a walk-up attic above. The full basement runs the length of the house, partially finished, with laundry, workshop and a walkout to a level lawn, flagstone patio and storage shed, plus two off-street spaces on a paved drive. Separate entries and separate heating systems. Walk to the Mount Auburn Street bus into Harvard Square, minutes to Star Market, Arsenal Yards and the Charles River paths, quick to Route 2 and the Pike. Sold as-is. Live on one floor and rent the other, or take the whole building. Both units delivered vacant at closing, with the seller requesting some flexibility on the closing date.
Welcome Home to 340 School Street in East Watertown! This massive 2 family property is situated in a prime Oakley Country Club location on a corner lot with entrances on both School Street and Maplewood Street. The property has been meticulously maintained & updated while keeping the original magnificent natural hardwood trim, flooring, french doors & leaded glass work. This is truly a gorgeous home boasting with charm & character that's rarely available today while offering all the modern conveniences for contemporary living. Both kitchens are very modern with granite counters, gas cooking & stainless appliances, all 3 baths are fully tiled & have also been completely redone. The upper unit is extremely large with roughly 2,600 square feet with 2 levels of living, 4 bedrooms, 2 full baths, formal living & dining rooms, gas fireplace, front & back staircases, 3 private exterior porches, 3rd floor laundry & ample storage. The 1st floor unit is also large with almost 1,750 square feet with 3 bedrooms, formal living & dining room, gas fireplace & 2 private exterior porches. Both kitchens are very modern with granite counters, gas cooking & stainless appliances, all 3 full baths are fully tiled & have also been completely redone. Both gas heating systems are steam based & have been redone, there's recent central a/c, the electrical has been completely updated with 2 separate 100 amp panels & even the gas hot water has been updated. There's also a 2-car garage, ample storage, separate water meters, lawn irrigation & professional landscaping, This property is really outstanding & in amazing condition with truly unlimited potential.
Offered for the first time in more than 80 years, this classic circa-1857 Mansard-style three-family, with more than 3,800 sf of living space, presents a value-add opportunity for owner-occupants, investors, developers, and alike. Ready for its next chapter, the property offers the opportunity to restore to its original architectural charm or explore a range of possibilities, including condominium conversion and building expansion. The generous 12,550-square-foot lot with six off-street parking spaces further enhances the property's significant upside development appeal and long-term investment potential. Ideally located just a few blocks from vibrant Watertown Square, offering easy access to restaurants, cafés, the public library, banks, pharmacies, and everyday amenities. Roughly one mile from Exit 127 off the Massachusetts Turnpike at Newton Corner, the location provides excellent commuter access to Cambridge, Downtown Boston and Logan International Airport.
Impeccably renovated two-unit multi-family in the heart of Watertown, combining 7 bedrooms and 4.5 baths across both homes with 3 dedicated parking spaces. Unit 24 spans three levels and is built for family living, with well-chosen finishes throughout. Three generously sized bedrooms and a full bath share the top floor with a versatile bonus area, perfect as a reading nook or arts and crafts space. On the floor below, a primary suite and living area sit alongside a large kitchen and dining space, both filled with natural light and well positioned for comfort and privacy. Stairs lead down to an impressive entry-way with hall tree and bench set-up. Unit 22 brings its own flexibility across two levels. The lower floor can serve as a second primary suite with office, or as private guest quarters, while two full bedrooms upstairs sit on opposite sides of the home for added privacy. A comfortable living area, full bath, and spacious laundry room round out the main level, which enjoys southeastern exposure and feels unusually bright for a first-floor unit. An ample shared driveway offers parking for both households, with room to spare. Each unit can be purchased separately or together as a multi-family opportunity. Come tour these beautifully redesigned homes and imagine the possibilities. 22and24olney.com
Newton Line! Perfect opportunity to expand this two-family home situated at the end of a dead-end street on over a 13,000+ sq ft piece of land.. Lower-level has a 1-bedroom apartment with separate entrance and private driveway. Main home is an original singe family with 3 bedrooms on the first floor with an eat-in kitchen, bright & spacious living room and full bath. Large walk-up attic bedroom with a half bath. The possibilities are endless for this property. Renovate and make your own custom single-family home or a development opportunity for 2 Townhomes as this home is in a T-Zone. Developers to do their own due diligence. Conveniently located on the Newton line near Watertown Square, the sought-after bike path, restaurants, shopping, cafe's and bus transportation to downtown, Central & Harvard Sq. with easy access to the Mass Turnpike. Welcome to Watertown!
PACKAGE SALE ONLY: 149 and 153 Palfrey Street are offered together for $1,999,900 and will not be sold separately.A rare opportunity to acquire two adjacent, family-held properties offering a compelling combination of private single-family living, established rental income and meaningful value-add potential.Originally purchased by the same family in 1958, the property was later subdivided, and the single-family residence at 149 Palfrey Street was constructed in 1963. Both properties have remained in the same family for nearly seven decades and are now being offered as one coordinated package.149 Palfrey Street is a well-maintained three-bedroom ranch featuring a fireplaced living room, dining room, den, eat-in kitchen, hardwood floors, central air and an attached garage. The substantial lower level offers a recreation room with a second fireplace, half bath, laundry and utility areas, workshop space and abundant storage. With approximately 2,500 square feet of living space across two levels, the home is comfortable and move-in ready while offering an opportunity to modernize over time.Next door, 153 Palfrey Street is an established four-unit property with approximately 3,000 square feet of living space. Units 2, 3 and 4 are occupied by tenants at will, providing immediate rental income. Unit 1 is vacant and requires renovation, creating an opportunity to improve the space, establish a new market rent and increase the property’s overall income potential. Unit 4 has been recently updated.Tenants are at will. Seller can delivery with the existing tenancies in place or vacant with required notice. No specific vacancy date is represented. An investor may preserve the current income while completing due diligence, planning improvements, obtaining estimates and arranging financing.For an owner-occupant, this package offers the privacy of a detached single-family home with income from four neighboring apartments—without sharing walls with tenants. For an investor, it presents five residences across two adjacent parcels, existing cash flow and immediate value-add potential.Two buildings. Five residences. Nearly seven decades of family ownership. One remarkable Watertown opportunity. Cross-reference companion MLS Listing IDs 73573985 and 73573993.
PACKAGE SALE ONLY: The $1,999,900 list price includes both 153 and 149 Palfrey Street. The properties must be purchased together and will not be sold separately.153 Palfrey Street is an established four-unit residential property offering current rental income and additional potential. The building contains almost 3,000 square feet of living area, 10 rooms and four full bathrooms according to public records.Units 2, 3 and 4 are occupied under written tenant-at-will agreements and currently generate $5,295 in total monthly rent. Unit 1 is vacant and requires renovation, while Unit 4 has been recently updated.Also included is the adjacent property at 149 Palfrey Street, a well-maintained three-bedroom ranch with central air, two fireplaces, an attached garage and substantial lower-level space.For an investor, the package offers five residences across two adjacent parcels with existing income. For an owner-occupant, it provides rental income from four neighboring apartments while preserving the privacy of a detached single-family home. Cross-reference companion MLS Listing IDs 73573985 and 73573995.
Well maintained Two Family located in West Watertown. This young two family has 5 rooms 3 bedrooms 1 bath on the first floor. Second floor has 6 rooms 3 bedrooms, office and 1 bath. Both living rooms have fireplaces. Second floor unit has a Mini split in the living room for air conditioning, spacious bedrooms, eat-in kitchen with nice cabinets & granite counters. Conveniently located near restaurants, shopping, parks, & the sought-after bike path. Perfect opportunity to own a well-cared for two family for investment or owner occupied. Schedule a viewing today. Welcome to Watertown!
Attention investors- don't miss this great opportunity in one of the top neighborhoods in East Watertown with a highly desirable location! Solid two family on a spacious lot with a large rear yard- both units have remodeled kitchens and baths done in 2017, new roof in 2017, resurfaced driveway in 2019, new back entrance done in 2021 (railing, stairs, and door) and replaced supports and beams for decks. There is possible expansion potential in the walk up attic, gas heating systems, and a two car garage. This property has strong rental income, is a stone's throw from Bus 71 to Harvard Sq, short distance to Watertown Sq and Cushing Sq, Belmont, plus I-90, and Storrow Drive. Easy access to shops and restaurants.
Welcome to 27 Woodleigh Rd, a well-maintained two-family home offering approximately 2,416 sq. ft. of living space in a desirable Watertown location. The property features two spacious units with separate entrances. One unit offers 2 bedrooms and 1 full bathroom, while the second features 3 bedrooms and 1 full bathroom. Both units offer updated kitchens and bathrooms and comfortable, functional layouts.Recent improvements include a newer roof (2021), two newer composite decks, and two gas hot water tanks installed in 2025. The property also offers an impressive driveway with parking for up to 10 cars.Additional space in both the basement and attic provides exciting future possibilities. The property is equipped with three electrical panels, including an additional panel that may support future expansion. The basement offers potential for an ADU, while the attic also presents potential for additional use and has independent exterior access currently enclosed within one of the bedrooms. Any ADU, expansion, or future use is subject to buyer due diligence and all required permits and municipal approvals.Conveniently located near shops, restaurants, public transportation and major routes, this property offers an excellent opportunity for an owner-occupant, investor, or multi-generational living. Easy to show.
Wonderful opportunity to own a beautifully maintained 3-bedroom, 2-bathroom duplex condo-quality home with a separate 2-bedroom first-floor rental unit, generating approximately $30,000 per year in additional rental income. Ideally located on the doorstep of Cambridge, this property offers an exceptional combination of comfortable living, rental income potential, and long-term value. Enjoy easy access to the city, with Mt. Auburn Street just moments away, as well as the Watertown-Cambridge Greenway for walking, biking, and recreation.The location provides convenient access to Storrow Drive, Memorial Drive, the Charles River, MIT, Harvard, and surrounding Cambridge amenities. With its desirable location, flexible living arrangement, and strong income-producing potential, this property presents an outstanding opportunity for an owner-occupant, investor, or anyone looking to build long-term real estate value.
WONDERFUL WATERTOWN! VIDEO: https://youtu.be/5C9JQjpXhcQ Solid, meticulously maintained brick two-family in East Watertown, ideal for an investor or owner-occupant seeking immediate rental income. Built in 1939 and standing on a 5,500 SF lot, this classic two-story duplex offers 1,750 SF of living area across two mirrored 2-bedroom, 1-bath units — 10 rooms total. Each unit features a bright living room, dining area, eat-in kitchen, screened porch, and two second-floor bedrooms with a full bath. Both units currently have long-term tenants in place, making this a turnkey income property from day one.This home has been meticulously maintained with a steady stream of big-ticket updates: a new roof in 2017, boilers replaced in 2019 and 2020, a new dishwasher installed December 2025, and a new washing machine added February 2026 — giving the next owner real peace of mind on major systems and appliances alike. The full basement is split into two individual sections — one per unit — each with its own utility/mechanical space and a semi-finished room offering flexible storage or non-sleeping bonus space...add heat and you could have 1300sqft+ units! Plus an installed waterproofing system. A detached 2-car garage adds valuable off-street parking, a rare commodity in this part of Watertown.Location is a standout: the property sits directly across from the Lowell Elementary School, and is just under a mile to the Waverley Commuter Rail stop for an easy inbound commute. It's also close to MBTA bus lines and just minutes from the shops, restaurants, and everyday conveniences of Coolidge Square — including Coolidge Hardware, Dunkin', Artemis Yoga, and a mix of local eateries — as well as the broader dining and retail corridor along Trapelo Road in nearby Waverley Square. Commuters and shoppers alike will also appreciate easy access to Arsenal Yards and the Charles River Greenway/bike path system.With income already in place, meticulously maintained mechanical systems, and a location that checks the boxes for schools, transit, and walkable amenities, 67-69 York Ave offers a compelling combination of stability and long-term upside in one of Watertown's most convenient East End pockets.
Exceptional opportunity to own a spacious two-family in one of Watertown's most sought-after neighborhoods. Offering over 2,300 sq ft of living space, each unit features 2 bedrooms, 1 full bath, hardwood floors, separate living and dining rooms, generous kitchens, and abundant natural light, creating layouts that appeal to both owner-occupants and investors. Recent improvements include a new roof, leaf-blocking gutters, and a fully renovated first-floor including the bathroom. The fenced corner lot provides outdoor space, while off-street parking adds convenience. Ideally situated just minutes from Watertown Square, Arsenal Yards, the Charles River Greenway, restaurants, shopping, public transportation, and major commuter routes with easy access to Boston and Cambridge. Whether you're looking to generate rental income, occupy one unit while offsetting your mortgage, or expand your investment portfolio, this property offers flexibility and long-term value in a high-demand location!
Developers and Contractors!! Presenting a multi-opportunity property. Do a complete gut renovation and restore to its original single family glory, renovate as 2 units and sell as condominiums, add on a second unit or ADU to suit your needs or knock down and build two new condominium units. Sited on 7,500 sq ft, the property is conveniently located off Mt. Auburn St near vibrant Coolidge Sq. with restaurants and wonderful small shops. Immediate access to busline to Harvard Sq and Watertown Sq. Also a short distance to Arsenal Yards!
Presenting an exceptional Muti-family property at 22-24 Carver Rd East in Watertown's desirable East End, Oakley CC neighborhood. This home was completely renovated in 2020 and features 2 duplex units consisting of 4 bedrooms, 3 baths, grand open kitchens with stainless appliances, expansive living/dining rooms that are perfect for entertaining and 4 private decks. The driveway has parking for 6 cars plus a garage that houses 2 more. it is a perfect place for investors or owner occupants looking for rental income to offset expenses. This home is great for multi-generational families with close proximity to parks, schools and dog park across the street. The location is convenient to Watertown Sq, Arsenal Yard, Charles River Greenway parks, schools and has easy access to Boston & Cambridge. The projected rent for 22 Carver Rd E is $5500/month. The seller lives in 24 Carver Rd E and is willing to lease back at $5500/month or we can deliver vacant. Each unit is in move in condition.
Exceptional opportunity to own this spacious 13-room, 6-bedroom, 2-bath multi-family home on a prominent corner lot in desirable East Watertown. Offering the perfect blend of size, location, and future potential, this classic property is filled w/ character, featuring a welcoming farmer's porch, high ceilings, oversized rooms, in-lead windows, and abundant natural light. The 1st floor unit offers 2 bedrooms, 1 bath, hardwood floors, generous living/dining area, and a convenient pantry. The upper unit spans 2 levels w/ 4 bedrooms, 1 bath, expansive living space, and endless possibilities for customization. The grounds are well manicured w/ mature plantings, paver walkway, patio, stone retaining wall, and 3 car wide paver driveway. Ideal for owner-occupants, investors, multi-generational living. Conveniently located steps from Coolidge Square, restaurants, shopping, parks, and public transit, w/ easy access to Arsenal Yards, Cambridge, Boston. A rare opportunity in a great neighborhood.
Watertown is located in Massachusetts.
