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$899,000
4 Beds 3 Baths ACTIVE Status 73573718 MLS 2,030 SqFt.
Rare offering! Affordable duplex two family located on a quiet street in the sought-after West End of Watertown. This home has been owned by the same family for over 50 years. Unit 25 offers 5 rooms 2 bedrooms 1 bath which include a bright & sunny living room, formal dining room, Kitchen which leads to a 3-season enclosed porch perfect for future expansion. Second floor offers two bedrooms and one bath. Private lower-level storage and laundry hook-ups. Unit 27 has a living room, formal dining area, kitchen leading to bonus finished family room with a half bath. Second floor has 2 bedrooms and 1 bath. Private lower-level storage & laundry included. Separate driveways for each unit. Nice backyard outdoor space. Maintenance free exterior with replacement windows. 2 new oil tanks. Hardwood floors in both units. Perfect opportunity for first time buyer or investor to be a part of bustling Watertown.

25-27 Bromfield St, Watertown

$1,199,999
5 Beds 2 Baths ACTIVE 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

$1,999,900
7 Beds 6 Baths ACTIVE Status 73573995 MLS 5,410 SqFt.
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.

149-153 Palfrey Street, Watertown

$1,999,900
4 Beds 4 Baths ACTIVE Status 73573993 MLS 2,914 SqFt.
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.

153 Palfrey St, Watertown

$1,250,000
4 Beds 2 Baths ACTIVE Status 73568445 MLS 2,200 SqFt.
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.

6 Bates Rd E, Watertown

$875,000
6 Beds 3 Baths UNDER AGREEMENT Status 73565669 MLS 3,767 SqFt.
Excellent opportunity for investors, flippers, and developers looking to expand their real estate portfolio in Watertown! This side-by-side multifamily property at 46–48 Bridge Street is situated on an approximately 9,095 SF corner lot, zoned for residential + mixed-use zoning, offering excellent potential for future development or redevelopment. Ideally positioned in an established residential neighborhood, across the street from a newly renovated (in progress) city park, the property is a short distance to Watertown Square, the Charles River, major roadways, public transportation, shopping, dining, parks, and everyday amenities. With Cambridge,Boston, and surrounding communities just minutes away, this location offers excellent access to all that Greater Boston has to offer. A compelling opportunity for those seeking value-add potential in a desirable and well-connected Watertown location

46-48 Bridge St, 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 ACTIVE 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

$1,000,000
4 Beds 2 Baths ACTIVE Status 73562267 MLS 1,750 SqFt.
WONDERFUL WATERTOWN! VIDEO: https://youtu.be/5C9JQjpXhcQ OPEN HOUSE: Sun, 9/6 2-3pm 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.

67-69 York Ave, Watertown

$1,099,000
4 Beds 2 Baths ACTIVE Status 73562096 MLS 2,312 SqFt.
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!

146-148 Waverley Ave, Watertown

$1,599,000
4 Beds 2 Baths UNDER AGREEMENT Status 73556838 MLS 3,000 SqFt.
INVESTORS, OWNER-OCCUPANTS, and 1031 BUYERS — TAKE NOTICE! This highly desirable, fully renovated two-family home abutting Oakley Country Club delivers turnkey living, strong rental potential, and an unbeatable Watertown location. Both units feature newer gourmet kitchens with quality cabinetry and high-end baths, along with new composite rear porches recently rebuilt for long-lasting durability. Major updates, including siding, replacement windows, electrical, central air, gas heat, and tankless hot water, ensuring modern comfort and efficiency throughout. Set on a beautifully landscaped lot, the property offers a detached garage, ample parking, and inviting outdoor space. With nothing left to do but move in, this is an exceptional opportunity for those seeking a renovated multi-family with expansion potential in the walk up attic and basement, in a prime neighborhood. Minutes to Harvard Square, Boston, the Mass Pike, and Route 2, 25–27 Flint Road combines convenience, quality, and long-term value.

25-27 Flint Rd, Watertown

$1,325,000
6 Beds 3 Baths UNDER AGREEMENT Status 73556741 MLS 4,285 SqFt.
Welcome to 28 Morse St Watertown This classic Mansard-style 3-family residence is a unique opportunity and a must see. The property features approx. 4,285 sq. ft. of living space spread over three floors across 14 total rooms. The large 8,250 sq. ft. lot features a gigantic parking area with 2 carports that can hold 4 cars as well. Unit 1 has been thoroughly renovated and feels very spacious with large bedrooms, open living room, and eat in kitchen. Unit 2 provides an expansive three-bedroom with open floor plan also including large bedrooms and just awaits your finishing touches. The top floor unit 3 features 2 bedrooms and has also been thoughtfully updated. This includes newer kitchen, newly renovated bathroom, and large generous bedrooms with great light in the unit. A 1,516 sq. ft. unfinished basement currently is used for utilities storage and a laundry area. The hot water and heating systems are gas. This property represents an outstanding investment or owner-occupant opportunity with versatile living space throughout

28 Morse St, Watertown

$2,400,000
6 Beds 6 Baths ACTIVE Status 73549312 MLS 4,767 SqFt.
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. 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.

22-24 Carver Rd East, Watertown

$1,299,000
6 Beds 2 Baths ACTIVE Status 73549206 MLS 2,889 SqFt.
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.

28 Appleton St, 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

$1,375,000
6 Beds 3 Baths ACTIVE Status 73546257 MLS 3,643 SqFt.
Fantastic opportunity for an owner-occupant or investor to own a rarely available three-family in highly desirable East Watertown/Coolidge Square! Great curb appeal in a prime location! The first-floor unit features 2 bedrooms, 1 bath, an updated kitchen, recessed lights, in-unit laundry, and central air. The second and third-floor units each offer 2 bedrooms, 1 bath, private balconies and gas heat, with the third floor being recently refreshed. Hardwood floors run throughout, with additional laundry and ample storage in the basement. Two driveways provide abundant off-street parking. Brand new roof recently installed. Excellent upside potential, as rents are well below market value. Conveniently located near public transportation with easy access to Cambridge and Boston. Enjoy nearby restaurants, shops, international markets, and Arsenal Yards. A rare investment opportunity in one of Greater Boston's most sought-after neighborhoods!

34 Irma Ave, Watertown

$1,050,000
5 Beds 2 Baths UNDER AGREEMENT Status 73541131 MLS 2,578 SqFt.
A great opportunity to own a well maintained two family home in highly desirable East Watertown. Filled with character, the first floor unit features 2 bedrooms, 1 full bath, a spacious kitchen, dining room with a beautiful built-in hutch, living room, and sunroom. Original woodwork and hardwood floors beneath the carpeting showcase the home's timeless appeal. The owner's unit spans two levels and offers 3 bedrooms, a full bath, kitchen, dining room, living room, sunroom, and a dedicated office, providing ample space for today's lifestyle. Additional highlights include a detached 2-car garage, plentiful off-street parking, and separate living spaces ideal for owner occupants or investors. Roof and Boiler less than 10 yrs old. Conveniently located near Cambridge, public transportation, shopping, dining, and just a mile from Arsenal Yards!

60-62 Templeton Pkwy, Watertown

$1,850,000
6 Beds 5 Baths UNDER AGREEMENT Status 73538490 MLS 3,900 SqFt.
1890ca Victorian two-family on one of Watertown's finest streets. Located just outside Watertown Square this unique property was built as a single-family house but now incorporates the added benefit of a rental unit in the basement. Classic period details feature prominently such as high-ceilings, oversized windows, stained-glass, 3 wood-burning fireplaces, hardwood floors, a hidden powder room and a first floor library with beamed ceiling, wainscotting and French Doors. The vintage mid-century kitchen offers ample cabinets, stone counters and large picture windows overlooking the yard and gardens. The 2nd floor contains 4 well-proportioned bedrooms which includes a master bedroom suite with fireplace. The 3rd floor is fully-finished with flex space for a game room or additional bedrooms and offers another bathroom. The lower-level apartment is vintage 1940's and has been consistently rented for decades.

27 Oliver Street, Watertown

$899,900
4 Beds 2 Baths UNDER AGREEMENT Status 73537593 MLS 1,800 SqFt.
Hard-to-find brick two-family duplex with a 2-car garage in the highly sought-after Lowell School district. Each spacious apartment offers a bright first-floor living room, dining area, and kitchen, plus two bedrooms and a full bath upstairs. Hardwood floors run throughout both units. A full, separate basement provides excellent storage and offers potential for additional living space with the right vision and sweat equity. This property is ideal for a first-time homeowner, investor, or condo converter looking for long-term value. Enjoy a private rear yard perfect for grilling, outdoor activities, and gatherings with friends and family. Opportunities like this don’t come often — act now and move into your new home this summer.

55-57 York Ave, Watertown

$1,250,000
6 Beds 3 Baths UNDER AGREEMENT Status 73528750 MLS 3,166 SqFt.
Rare opportunity to acquire a well-maintained legal 3-family home perfectly located in east Watertown. Featuring 16 rooms, 6 bedrooms, 3 bathrooms, and 3 levels of living space. The property has been well maintained w/ hardwood floors, abundant natural light, excellent ceiling height, and an updated kitchen in Unit 2. Each unit is serviced w/ its own heating system, electrical panel, and hot water tank. Vinyl siding, replacement windows, and an architectural shingle roof. Outstanding location on the bus line and minutes to Arsenal Yards, Charles River, Coolidge Sq., Cambridge/Boston, Watertown Schools, and major highways. Terrific investment opportunity with great rental history in highly desirable east Watertown.

204-206 School St, Watertown

$1,399,900
7 Beds 5 Baths UNDER AGREEMENT Status 73517311 MLS 4,029 SqFt.
Set in the beloved Oakley CC neighborhood, this inviting Watertown two-family blends early-20th-century charm with modern updates. Perched on a corner lot, the home offers flexibility for multigenerational living, rental income, or condo conversion. The first-floor unit features an airy open layout with a bright family room, dining area, updated kitchen, two bedrooms, and two full baths. The upper unit lives like a single-family with two floors, five bedrooms, three full bathrooms, a cozy living room with wood-burning fireplace, classic dining room with built-in hutch, and an updated kitchen. Enjoy Boston skyline views from upstairs and country club views from all floors and effortless access to local amenities, transit, and commuter routes. Showings to begin at group showings Thursday 5/14 and Friday 5/15 from 1-2PM.

64 Commonwealth Rd, Watertown

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