Browse All Watertown MA 5 Bedroom Properties for Sale

5 Beds ⋅ 2 Baths ⋅ PRICE CHANGED Status ⋅ 73593805 MLS ⋅ 2,176 SqFt.

Space, character, and an exceptional Watertown location come together in this two-family home offering 2,176 sq ft of living space! The vacant first-floor unit features three bedrooms, a full bath, freshly refinished hardwood floors, fresh paint, all-new replacement windows, and charming original woodwork and built-ins. The kitchen offers new flooring and appliances, while the entire unit has been deleaded with a Certificate of Compliance. Upstairs, the tenant-occupied second unit features two bedrooms, a full bath, hardwood floors, in-unit laundry, and an additional sunroom offering flexible space for an office or storage. Currently rented for $2,700 per month with a lease through July 2027, this unit provides immediate rental income. Major improvements include two brand-new oil tanks, two new hot water heaters, updated 100-amp electrical panels, and separate utilities. Both units enjoy rear decks overlooking a very spacious, fully fenced shared backyard. A one-car garage for storage and off-street parking for approximately 4–6 vehicles add further appeal. Ideally located near Watertown Square, Arsenal Yards, the Charles River Greenway, public transportation, and major routes into Cambridge and Boston. An outstanding opportunity to enjoy owner-occupancy with rental income in a desirable Watertown location!

44-46 Quimby Street, Watertown

$1,125,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73592962 MLS ⋅ 2,126 SqFt.

Well maintained brick & Vinyl two family, first floor consists of a living room, kitchen, two beds and full bath. Top unit rehabbed in 2010, central air, Large modern kitchen with granite island, open floor plan with formal dining area, a fireplace'd Family room, full bath with laundry, top floor consists of two bedrooms. This well maintained multi-family boasts updated 300 amp electrical, ample off street parking, coin op laundry for tenants as well as two storage sheds, great for tools, motorcycles, bikes and more!

24 Charles St, Watertown

$1,500,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73589846 MLS ⋅ 3,050 SqFt.

**INCOME-PRODUCING WATERTOWN TWO-FAMILY!** Ideally located on Mount Auburn Street with convenient access to Boston and surrounding communities, this two-family property presents an excellent opportunity for both investors and owner-occupants. Currently generating approximately **$7,200 per month in rental income**, both units are occupied with tenants at will. The property offers immediate income with potential upside for the next owner. Features include separate water meters, off-street parking, and deleaded status. Whether you're looking to expand your investment portfolio or occupy one unit while generating rental income from the other, 745–747 Mount Auburn Street offers flexibility and opportunity in a highly desirable Greater Boston location. Property to be sold **AS IS**; buyers and their agents are encouraged to conduct their own independent due diligence. Listing agent is related to the seller.

745/ 747 Mount Auburn St, Watertown

$999,000

5 Beds ⋅ 3 Baths ⋅ CONTINGENT Status ⋅ 73589555 MLS ⋅ 1,900 SqFt.

Newton Line! Perfect opportunity to expand this single 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 a 2 level ranch style singe family with a walk-up finished attic. 3 bedrooms on the first floor with an eat-in kitchen, bright & spacious living room and full bath. Attic consists of 1 or 2 bedrooms 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!

25 Lyons Ct, Watertown

$950,000

5 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73588201 MLS ⋅ 2,484 SqFt.

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.

326-328 Charles River Rd, Watertown

$900,000

5 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73587698 MLS ⋅ 2,240 SqFt.

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.

51-53 Prentiss St, Watertown

$1,449,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73581941 MLS ⋅ 2,183 SqFt.

Welcome to this beautifully renovated five-bedroom Cape-style home, ideally situated in one of Watertown’s desirable residential neighborhoods. Thoughtfully updated throughout, this move-in-ready home combines classic charm with modern finishes and a flexible floor plan. The main level features a spacious living room with a fireplace, a versatile room off the main living area that can serve as a bedroom or home office. With bedrooms located on both the first and second floors, the layout provides flexibility for a variety of living arrangements. The fully finished lower level adds valuable living space, perfect for a recreation area, home gym, or office. Outside, enjoy an expansive, level backyard featuring a built-in BBQ station (brick blocks mangal and tandoori - total of 2,200 bricks, handmade in 2023) an ideal setting for outdoor dining, entertaining, gatherings, or simply relaxing at home. Conveniently located near public transportation, parks, walking trails, shopping, restaurants, major routes, and all that Watertown has to offer. With five bedrooms, beautifully renovated living spaces, a fully finished lower level, and an impressive backyard entertaining area, this home is ready for its new owners to move in and enjoy.

47 Rosedale Rd, Watertown

$1,250,000

5 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73581743 MLS ⋅ 2,592 SqFt.

Location! Rare waterfront lead tested with reports 2-family (also being sold as condos) in Watertown, overlooking the Charles River and views of the Watertown Boat Harbor. This area is perfect for anyone who loves the outdoors, to be on the water for water activities or, enjoys biking, walking/jogging along the river parks and the bike path. This property features 2 units. The first floor has 2 bedrooms, a sun room/office, full bath, open living/dining rooms with gorgeous natural woodwork, mudroom, and original moldings. The eat-in kitchen has S/S appliances with lots of quartz counterspace & cabinets. The second floor has 3 bedrooms, a sun room/office, full bath, open living/dining rooms with gorgeous natural woodwork, cabinetry and original moldings. The eat-in kitchen has S/S appliances with lots of quartz counter space & cabinets. Laundry is located in the basement with each unit having their own with lots of workspace & extra storage. Air Source Electric Heat pumps for Heat and AC. Home has been insulated. Each unit gets 2 tandem off street parking with one car spot each in the carport. Front and back porches, shed for bike storage and a yard for outside entertaining. 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.

330-332 Charles River Rd, Watertown

$999,000

5 Beds ⋅ 3 Baths ⋅ CONTINGENT Status ⋅ 73580479 MLS ⋅ 1,900 SqFt.

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!

25 Lyons Ct, Watertown

$1,495,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73573722 MLS ⋅ 2,840 SqFt.

Gracious Center Entrance Colonial located near the Oakley Country Club. Spacious & bright front to back Living Room with beamed ceilings, French Doors, and beautiful fireplace with mantle. Nice sunroom with loads of light. Formal dining room. Eat-in kitchen with Cherry Cabinets, granite counters, & S.S Appliances. Second floor has 4 corner bedrooms separated by large foyer with tiled bath. Walk-up third floor perfect for storage or potential expansion. Finished lower-level perfect for in-law or future ADU. Basement offers a full kitchen with dining area, living room, bedroom & full bath. Lower has its own entrance and egress. Gleaming hardwood floors throughout, replacement windows, new dual gas furnace & on demand water heater. Central Air. Laundry and storage in lower level. Oversized two car garage with ample off-street parking. Conveniently located between Cushing Sq. in Belmont & Watertown Sq. Steps to the new Net Zero Watertown High School. Close to all restaurants, cafe's, specialty shops, transportation, The Lowell Elementary School, the sought-after bike path. Short drive to the Arsenal Yards. Easy access to the Mass Pike. This home has been in the same family for over 50 years and awaits a new family to create new memories. Welcome to Watertown!

158 Common St, Watertown

$1,199,999

5 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73573835 MLS ⋅ 2,466 SqFt.

Meticulously maintained, this 2-family home at 49 Hall Ave is perfect for investors or owner-occupants. Enjoy total peace of mind with updated electrical, gas heat, full insulation, and replacement windows. Unit 1 features a bright, open-concept floor plan with 5 rooms, 2 bedrooms, 1 full bath, a kitchen breakfast bar, and in-unit laundry. Unit 2 boasts a spacious, open 6-room layout with 3 bedrooms, 1 full bath, private laundry, and sleek, contemporary finishes throughout. Exceptional outdoor amenities include a 1-car garage, a 4-car tandem driveway, a manageable yard, and a large shared deck. Benefit from an unbeatable commuter location just steps from Cushing Square shops, restaurants, and the new, state-of-the-art Watertown High School, with easy access to public transit, Rt. 16, and Rt. 2. Ready to rent or move right in!

49 Hall Ave, Watertown

$1,499,000

5 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73564758 MLS ⋅ 2,416 SqFt.

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.

27 Woodleigh Rd, Watertown

$1,099,000

5 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73564587 MLS ⋅ 2,300 SqFt.

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.

7 Hearn, Watertown

$900,000

5 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73561201 MLS ⋅ 2,227 SqFt.

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!

33 Melendy Ave, Watertown

$2,645,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73547203 MLS ⋅ 4,537 SqFt.

Fully renovated and thoughtfully restored, this exceptional five-bedroom, four-and-a-half-bath home offers rare multigenerational living in one of Watertown’s most desirable neighborhoods. High ceilings, beautiful architectural details, and abundant natural light complement an open, inviting layout designed for modern living. The beautifully appointed kitchen features a separate pantry and flows into generous living and dining spaces. The serene primary suite includes an enclosed sunlit balcony, while a private lower-level in-law suite with separate entrance and versatile third-floor guest or teen suite provide outstanding flexibility for extended family, guests, or work-from-home living. Outside, enjoy a spacious yard with professionally designed hardscape, landscaping, and curated plantings. Just moments from Arsenal Yards, the Charles River Greenway, dining, shopping, fitness, and entertainment, with convenient access to Boston and major commuter routes. One year builders warranty included.

68 Barnard Avenue, Watertown

$960,000

5 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73547064 MLS ⋅ 2,250 SqFt.

Located in highly desirable Warrendale, this spacious two-family home offers an exceptional opportunity for homeowners, developers, and investors seeking to build equity. The first-floor apartment features five rooms with two bedrooms, while the second-floor unit offers six rooms with three bedrooms. Both apartments showcase hardwood floors in the living rooms, dining rooms, and bedrooms, along with classic built-in dining room hutches that add timeless character. Double-pane windows provide improved energy efficiency, and each unit includes both front and rear covered porches, perfect for relaxing or enjoying the outdoors. Ideally situated near Waverley Square, this property offers convenient access to local shops, restaurants, parks, Watertown Center, and Arsenal Yards. Enjoy the nearby Charles River walking, jogging, and bike path. Commuters will enjoy easy access to the Massachusetts Turnpike, multiple public transportation options, and the commuter rail.

18 Prospect Street, Watertown

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Browse All Watertown MA 5 Bedroom Properties for Sale

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