Oak Square, MA homes for sale & real estate

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OPEN TODAY, 11AM TO 12:30PM

21 Upcrest Rd, Boston, MA 02135
21 Upcrest Rd, Boston, MA 02135
21 Upcrest Rd, Boston, MA 02135
ABOUT THIS HOME
Oak Square, MA Homes for Sale
Welcome to this charming four-bedroom Colonial tucked away on a quiet dead-end street, just a short walk to Oak Square and local shops. This beautifully updated home features brand-new hardwood flooring throughout, a newly added half bath, and new windows on the way, offering comfort, style, and energy efficiency. The spacious first floor includes a sun-filled, front-to-back 12x23 living room—perfect for entertaining—as well as a formal dining room and a generous kitchen ready for your personal touch. Upstairs, you'll find four well-ventilated bedrooms, ideal for cool summer nights. A bright and airy three-season sunroom off the 4th bedroom (9x17) provides flexible space—p

$950,000

4 beds1.5 baths1,906 sq ft

21 Upcrest Rd, Boston, MA 02135

4,050 sq ft lot • Very walkable

214 Market St #201, Boston, MA 02135
214 Market St #201, Boston, MA 02135
214 Market St #201, Boston, MA 02135
ABOUT THIS HOME
Oak Square, MA Homes for Sale
BEST BUILDING. BEST LAYOUT. BEST PRICE! 2+ bedroom/2 bath condominium residence with 2 car parking, a private deck and over 1,200 sq/ft of living area in The Saybrook, a beautifully designed + crafted building near Boston Landing, Brighton Center and more! Enter into an open floor plan kitchen with contemporary cabinetry, quartz counters and an island with seating for 3. Beyond the kitchen is an area for a dining table and a living room space with a fireplace. There is also an adjacent study/home office with access to a 70 sq/ft deck. The bedrooms are both of a nice size, with the primary bedroom having a Juliette balcony, a walk in closet and a gorgeous marble bath with double vanity sink

$848,000

2 beds2 baths1,201 sq ft

214 Market St #201, Boston, MA 02135

$745 HOA • 2 garage spots • Very walkable

365 Faneuil St #2, Boston, MA 02135
365 Faneuil St #2, Boston, MA 02135
365 Faneuil St #2, Boston, MA 02135
ABOUT THIS HOME
Oak Square, MA Homes for Sale
Rare Opportunity. Unbeatable Value. Move right into this freshly painted 1-bedroom with deeded parking (Space #4) and a price that’s hard to beat. You're just steps to bus lines for Kenmore, Harvard Square, and the Express Bus to downtown. Stroll to neighborhood restaurants, parks, and shops; Boston Landing and the Charles River are a quick drive away, and the Mass Pike is minutes from your door. Inside, enjoy wood floors, new window treatments, an updated bath, and an eat-in kitchen with a new refrigerator. Laundry is located just outside the unit. A Lead Inspection Compliance Report is on file. Low condo fee keeps monthly costs down, and owner-occupants can currently save $3,984.21

$349,500

1 bed1 bath590 sq ft

365 Faneuil St #2, Boston, MA 02135

$244 HOA • Community pool • Very walkable

87-89 Bennett St, Boston, MA 02135
87-89 Bennett St, Boston, MA 02135
87-89 Bennett St, Boston, MA 02135
ABOUT THIS HOME
Oak Square, MA Homes for Sale
Fantastic corner lot 2 family on beautiful tree lined Bennett St. The 1st floor unit features 2 spacious bedrooms 1 bath and a spacious living and dining room with hardwood floors. The second floor unit also features spacious bedrooms living and dining room. Both units are ready for you to bring your creative touches to make this beautiful home shine. Outside there is off street parking for 3 vehicles a garage and a large nicely landscaped yard.

$1,200,000

2 beds1 bath2,316 sq ft

87-89 Bennett St, Boston, MA 02135

7,260 sq ft lot • Garage • Very walkable

99 Tremont St #105, Boston, MA 02135
99 Tremont St #105, Boston, MA 02135
99 Tremont St #105, Boston, MA 02135
ABOUT THIS HOME
Oak Square, MA Homes for Sale
Movtivated seller for this move-in ready studio residence at 99 Tremont! Located in the Oak Square neighborhood of Brighton, this community is ideally situated and offers an ideal commute to downtown Boston. Hop on the I-90 Massachusetts Turnpike or Express Bus right to the Back Bay or the Financial District. At 99 Tremont, open concept floor plans are outfitted with sophisticated appliances, sleek counters, wide plank floors and tall windows. Featuring parking, fitness center, billiards room, media lounge, elevated garden terrace, and more! 99 Tremont offers you an unparalleled lifestyle experience in a vibrant, walkable location. Video tour is avaialble.

$520,000

0 beds1 bath616 sq ft

99 Tremont St #105, Boston, MA 02135

$437 HOA • Very walkable

Property at 99 Tremont #205, Boston, MA 02135, 1 bed, 1 bath

$525,000

1 bed1 bath616 sq ft

99 Tremont #205, Boston, MA 02135

Property at 664 Washington St, Boston, MA 02135, 14 beds, 6 baths

$3,930,000

14 beds6 baths— sq ft

664 Washington St, Boston, MA 02135

Property at 21 Glenley Ter, Boston, MA 02135, 5 beds, 3 baths

$1,400,000

5 beds3 baths3,493 sq ft

21 Glenley Ter, Boston, MA 02135

Property at 709 Washington St #709, Boston, MA 02135, 3 beds, 2 baths

$849,000

3 beds2 baths2,129 sq ft

709 Washington St #709, Boston, MA 02135

Property at 12 Bigelow Cir #3, Boston, MA 02135, 2 beds, 1 bath

$675,000

2 beds1 bath1,238 sq ft

12 Bigelow Cir #3, Boston, MA 02135

Property at 23 Gordon St, Boston, MA 02134, 5 beds, 2.5 baths

$999,000

5 beds2.5 baths3,179 sq ft

23 Gordon St, Boston, MA 02134

Property at 121 Tremont St Unit B1, Boston, MA 02135, 1 bed, 1 bath

$393,000

1 bed1 bath767 sq ft

121 Tremont St Unit B1, Boston, MA 02135

Property at 99 Tremont St #213, Boston, MA 02135, 2 beds, 2 baths

$789,999

2 beds2 baths1,091 sq ft

99 Tremont St #213, Boston, MA 02135

Property at 214 Market St #202, Boston, MA 02135, 2 beds, 2 baths

$789,000

2 beds2 baths1,014 sq ft

214 Market St #202, Boston, MA 02135

Property at 121 Tremont St Unit A2, Boston, MA 02135, 1 bed, 1 bath

$395,000

1 bed1 bath726 sq ft

121 Tremont St Unit A2, Boston, MA 02135

Property at 11 Faneuil St, Boston, MA 02135

$5,000,000

— beds— baths— sq ft

11 Faneuil St, Boston, MA 02135

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Nearby homes that match your criteria

NEW 21 HRS AGO

1731 Beacon St #809, Brookline, MA 02445
1731 Beacon St #809, Brookline, MA 02445
1731 Beacon St #809, Brookline, MA 02445
ABOUT THIS HOME
Oak Square, MA Homes for Sale
Perfectly perched on 8th floor, far above the clamour of city life, this stunning 997 sq ft 2-bed condo with bamboo floors is bathed in natural sunlight all day long, offering sweeping Northeast views of the city from every window!! Open concept Living/Dining area with abundant storage space, including an enviable Walk-in closet in the Primary Bedroom. The Dining Room has been smartly reconfigured into a Second Bedrm/Office by incorporating the exterior patio into the living space. Enjoy carefree living at Brookline's most desirable Full Amenity complex. INCLUDED: 24 Hr Concierge, 4-Season Heated Swimming Pool, Garage Pkng, Guest Pkng, Designated Storage, Gym, Clubroom, Library and common

$749,900

2 beds1 bath997 sq ft

1731 Beacon St #809, Brookline, MA 02445

$785 HOA • Garage • Community pool

OPEN TODAY, 12:30PM TO 1:30PM

1588 Beacon St #2, Brookline, MA 02445
1588 Beacon St #2, Brookline, MA 02445
1588 Beacon St #2, Brookline, MA 02445
ABOUT THIS HOME
Oak Square, MA Homes for Sale
Elegant prewar building in the heart of the best area in vibrant Brookline surrounded by restaurants and shopping. Beautifully updated floor-through 3-4 bedroom 2 full bath with owner/architect’s custom touch everywhere! Classic detail, ceiling height, flooded with natural light , set back from street by stone paths creating privacy, city and garden views with charm from only brownstones built in this special era combined beautifully with today's lifestyle and open concept living. Three unusually large, private bedrooms with an option to have a 4th , two full baths, formal dining, inviting living room, and designer eat-in kitchen. Upgrades include central air, glamorous master bath, a

$1,149,000

3 beds2 baths1,481 sq ft

1588 Beacon St #2, Brookline, MA 02445

$822 HOA • Garage • Very walkable

66 Union St, Boston, MA 02135
66 Union St, Boston, MA 02135
66 Union St, Boston, MA 02135
ABOUT THIS HOME
Oak Square, MA Homes for Sale
Attention home owners and investors! Tremendous investment Opportunity awaiting for you! This well maintained three-family home boasting 4200 sq. ft living space w. six side by side parking spaces located in the heart of Brighton. Each unit features four bedrooms, one bathroom and a back balcony, w. shared laundry unit in the basement. Major renovation was completed in 2020. All units are under leasing cycles of Aug 31st, generating a healthy $10,700 monthly income and eligible for residential tax exception if owner occupied. Conveniently locate in between/close to Boston University and Boston College, with walking distance to Green Line T Station, Super Markets, Brighton Center.

$2,250,000

12 beds3 baths4,182 sq ft

66 Union St, Boston, MA 02135

5,000 sq ft lot • Very walkable

OPEN TODAY, 12PM TO 2PM

249 Corey Rd #306, Boston, MA 02135
249 Corey Rd #306, Boston, MA 02135
249 Corey Rd #306, Boston, MA 02135
ABOUT THIS HOME
Oak Square, MA Homes for Sale
Welcome to The Jordan, Brighton’s newest boutique condominium ideally located on the Brookline town line. This well-designed complex features 34 modern units, just steps from Whole Foods and public transportation, offering unparalleled convenience for urban living. Residents enjoy premium amenities, including a landscaped private courtyard with grill, a spacious rooftop terrace with 360° views, a fitness center, resident lounge and secure underground assigned parking. Each unit showcases open-concept layouts and high-end finishes, with a gourmet kitchen featuring Fisher & Paykel appliances and sleek quartz countertops. With over a dozen unique floor plans, The Jordan offers

$1,037,500

2 beds1 bath940 sq ft

249 Corey Rd #306, Boston, MA 02135

$713 HOA • Garage • Very walkable

OPEN TODAY, 12PM TO 2PM

249 Corey Rd #308, Boston, MA 02135
249 Corey Rd #308, Boston, MA 02135
249 Corey Rd #308, Boston, MA 02135
ABOUT THIS HOME
Oak Square, MA Homes for Sale
Welcome to The Jordan, Brighton’s newest boutique condominium ideally located on the Brookline town line. This well-designed complex features 34 modern units, just steps from Whole Foods and public transportation, offering unparalleled convenience for urban living. Residents enjoy premium amenities, including a landscaped private courtyard with grill, a spacious rooftop terrace with 360° views, a fitness center, resident lounge and secure underground assigned parking. Each unit showcases open-concept layouts and high-end finishes, with a gourmet kitchen featuring Fisher & Paykel appliances and sleek quartz countertops. With over a dozen unique floor plans, The Jordan offers

$675,000

1 bed1 bath786 sq ft

249 Corey Rd #308, Boston, MA 02135

$540 HOA • Garage • Very walkable

OPEN TODAY, 12PM TO 2PM

249 Corey Rd Unit 403PH, Boston, MA 02135
249 Corey Rd Unit 403PH, Boston, MA 02135
249 Corey Rd Unit 403PH, Boston, MA 02135
ABOUT THIS HOME
Oak Square, MA Homes for Sale
Welcome to The Jordan, Brighton’s newest boutique condominium ideally located on the Brookline town line. This well-designed complex features 34 modern units, just steps from Whole Foods and public transportation, offering unparalleled convenience for urban living. Residents enjoy premium amenities, including a landscaped private courtyard with grill, a spacious rooftop terrace with 360° views, a fitness center, resident lounge and secure underground assigned parking. Each unit showcases open-concept layouts and high-end finishes, with a gourmet kitchen featuring Fisher & Paykel appliances and sleek quartz countertops. With over a dozen unique floor plans, The Jordan offers

$1,049,000

1 bed1 bath760 sq ft

249 Corey Rd Unit 403PH, Boston, MA 02135

$638 HOA • Garage • Very walkable

Property at 249 Corey Rd Unit 407PH, Boston, MA 02135, 2 beds, 2 baths

$1,299,000

2 beds2 baths1,166 sq ft

249 Corey Rd Unit 407PH, Boston, MA 02135

Property at 249 Corey #103, Boston, MA 02135, 2 beds, 2 baths

$1,349,000

2 beds2 baths1,125 sq ft

249 Corey #103, Boston, MA 02135

Property at 130 Sutherland Rd #1, Boston, MA 02135, 2 beds, 1 bath

$529,000

2 beds1 bath727 sq ft

130 Sutherland Rd #1, Boston, MA 02135

Property at 88 Strathmore #7, Boston, MA 02135, 2 beds, 1 bath

$649,000

2 beds1 bath877 sq ft

88 Strathmore #7, Boston, MA 02135

Property at 285 Corey Rd #7, Boston, MA 02135, 2 beds, 1 bath

$639,000

2 beds1 bath916 sq ft

285 Corey Rd #7, Boston, MA 02135

Property at 5 Braemore Rd #10, Boston, MA 02135, 1 bed, 1 bath

$329,000

1 bed1 bath385 sq ft

5 Braemore Rd #10, Boston, MA 02135

Property at 9 Downing Rd, Brookline, MA 02445, 8 beds, 5 baths

$2,995,000

8 beds5 baths5,803 sq ft

9 Downing Rd, Brookline, MA 02445

Property at 1515 Commonwealth Ave #415, Boston, MA 02135, 1 bed, 1 bath

$849,000

1 bed1 bath909 sq ft

1515 Commonwealth Ave #415, Boston, MA 02135

Property at 1945 Commonwealth Ave #65, Boston, MA 02135, 1 bed, 1 bath

$435,000

1 bed1 bath620 sq ft

1945 Commonwealth Ave #65, Boston, MA 02135

Property at 1774 Beacon St #6, Brookline, MA 02445, 2 beds, 1 bath

$810,000

2 beds1 bath1,036 sq ft

1774 Beacon St #6, Brookline, MA 02445

Property at 56 Park Vale Ave #4, Boston, MA 02134, 1 bed, 1 bath

$385,000

1 bed1 bath470 sq ft

56 Park Vale Ave #4, Boston, MA 02134

Property at 1789 Commonwealth, Boston, MA 02135, 14 beds, 6 baths

$3,995,000

14 beds6 baths6,206 sq ft

1789 Commonwealth, Boston, MA 02135

Property at 15 N Beacon St #104, Boston, MA 02134, 2 beds, 1.5 baths

$545,000

2 beds1.5 baths778 sq ft

15 N Beacon St #104, Boston, MA 02134

Property at 1408 Commonwealth Ave Unit 8-15, Boston, MA 02135, 1 bed, 1 bath

$444,900

1 bed1 bath685 sq ft

1408 Commonwealth Ave Unit 8-15, Boston, MA 02135

Average home prices near Oak Square, MA

Cities

Neighborhoods

Jamaica Plain homes for sale
$839,000
Fenway-Kenmore homes for sale
$1,495,000
Cambridgeport homes for sale
$1,024,950
Brighton homes for sale
$679,000
North Cambridge homes for sale
$1,075,000
Mission Hill homes for sale
$685,000
Fenway / Kenmore Square homes for sale
$1,219,000
Allston homes for sale
$699,000
Chestnut Hill homes for sale
$3,525,000
Coolidge Corner homes for sale
$1,071,000

Oak Square, MA real estate trends

All Home Types trends in Oak Square, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$906,250

-17.6% YoY | Jun 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Jun 2025

Growth

% YoY

Oak Square, MA

$906,250

-17.6%

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