High Street Hill, MA homes for sale & real estate

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14 Irving St, Brookline, MA 02445
14 Irving St, Brookline, MA 02445
14 Irving St, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Truly stunning with historic charm, this Brookline Georgian Revival is ready for its next chapter. Ideally located in the Pill Hill District, this home is a rarity given most of the original detailing & features remain intact from the Palladian windows to the tracery in the sidelights & fanlight at the sunlit front entrance. Gracious formal dining & living room with Delft tile fireplace surround and more original detailing. Eat in kitchen w/ adjacent to an over-sized Butler's pantry. Rear mudroom entry and powder room complete the first level. Second level is graced by a second Palladian window and lovely, open landing. Three nicely proportioned bedrooms sit at each corner

$2,500,000

5 beds3.5 baths3,873 sq ft

14 Irving St, Brookline, MA 02445

7,670 sq ft lot • 2 garage spots • Community pool

60 Glen Rd #107, Brookline, MA 02445
60 Glen Rd #107, Brookline, MA 02445
60 Glen Rd #107, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Set within the serene, park-like grounds of Olmsted Park Condominiums, this charming one-bedroom, one-bath condo offers the perfect blend of nature and convenience. Located in the heart of the Emerald Necklace, you'll enjoy direct access to scenic Olmsted Park trails, ideal for morning jogs or leisurely walks. Inside, this inviting unit features a bright and functional layout, complemented by on-site amenities including an exercise room, library and laundry in the building. The well-maintained community provides a peaceful retreat while keeping you close to everything. Just minutes from Coolidge Corner, the Green Line T-stop, Fenway Park and the renowned Longwood Medical Area, this home off

$499,900

1 bed1 bath582 sq ft

60 Glen Rd #107, Brookline, MA 02445

$735 HOA • Very walkable

69 Walnut St #4, Brookline, MA 02445
69 Walnut St #4, Brookline, MA 02445
69 Walnut St #4, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Floor through one level 4 bedroom and 4 full bath condo in elevator building. Thoughtfully designed w/ luxurious finishes & exceptional attention to detail. Step into a sleek chef’s kitchen/family room adorned with custom Italian cabinetry, exquisite quartz countertops, and a dramatic curved wall of glass that bathes the space in natural light. Large center island completes the gourmet experience. Throughout the home, soaring 9-foot ceilings enhance the sense of space, while an ubundance of Italian windows framing captivating views. Wonderful outdoor space, home office & in-unit laundry. The bathrooms are a showcase of modern sophistication, featuring rich porcelain finish

$2,998,008

4 beds4 baths2,510 sq ft

69 Walnut St #4, Brookline, MA 02445

$1,469 HOA • Garage • Walker's paradise

65 Glen Rd Unit H4, Brookline, MA 02445
65 Glen Rd Unit H4, Brookline, MA 02445
65 Glen Rd Unit H4, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Welcome to a truly exquisite offering at The Park in Brookline. This elegant and sun-drenched two level corner unit boasts soaring beamed ceilings, a grand fireplace, and oversized windows that flood the space with natural light. Upon entry, you're greeted by a recently renovated kitchen, where sleek design meets functionality, and windows frame serene views of the garden. Spanning 1,213 square feet, this two-bedroom, one and a half bath home includes a primary bedroom featuring an en-suite bath with luxurious radiant heat floors. A second spacious bedroom and a half bath complete the bedroom level. This home is adorned with rich hardwood floors throughout, central air and in-unit laundry,

$849,000

2 beds1.5 baths1,213 sq ft

65 Glen Rd Unit H4, Brookline, MA 02445

$846 HOA • Very walkable

36 Allerton St, Brookline, MA 02445
36 Allerton St, Brookline, MA 02445
36 Allerton St, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Elegant 2005 home in historic Pill Hill. Open floorplan, 9+ft ceilings, spacious throughout with oversized windows and garden views. Spectacular kitchen with marble island & eat-in nook surrounded by windows and open to a sunny family room. Glass doors to private patio-garden with intricate plantings and heated lap pool enclosed by architecturally patterned brick walls, detailed with gas lamps and wrought ironed arched entries. 2nd and 3rd floors with 5 bedrooms, covered porch, 2 designer baths, laundry, master suite w/ marble bath and walk-in closet. Finished basement has separate entrance, full bath, kitchenette – spacious for family room, gym, au pair, etc. Close walk

$4,350,000

5 beds4.5 baths5,122 sq ft

36 Allerton St, Brookline, MA 02445

8,276 sq ft lot • Pool • Walker's paradise

Property at 30 Cumberland Unit W-4, Brookline, MA 02445, 2 beds, 2 baths

$945,000

2 beds2 baths1,246 sq ft

30 Cumberland Unit W-4, Brookline, MA 02445

Property at 71 Highland Rd, Brookline, MA 02445, 3 beds, 1 bath

$1,300,000

3 beds1 bath1,000 sq ft

71 Highland Rd, Brookline, MA 02445

Property at 69 Walnut St #6, Brookline, MA 02445, 2 beds, 2 baths

$1,349,999

2 beds2 baths983 sq ft

69 Walnut St #6, Brookline, MA 02445

Property at 69 Walnut St #2, Brookline, MA 02445, 3 beds, 2 baths

$1,599,000

3 beds2 baths1,105 sq ft

69 Walnut St #2, Brookline, MA 02445

Property at 31 Highland #31, Brookline, MA 02445, 3 beds, 3.5 baths

$2,598,000

3 beds3.5 baths2,500 sq ft

31 Highland #31, Brookline, MA 02445

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Nearby homes that match your criteria

99 Pond Ave #220, Brookline, MA 02445
99 Pond Ave #220, Brookline, MA 02445
99 Pond Ave #220, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Welcome to all the conveniences and amenities of the Brook House in this renovated 1,300 sq ft, 2-bedroom, 2-bathroom condo. From the entry hall, the generous living/dining room opens onto a covered porch overlooking the courtyard. The kitchen includes stainless-steel appliances including gas cooking, granite counters, and wood cabinetry. Relax in the main suite with en-suite tile bathroom, walk-in closet, and additional wall of closets. Spaced for privacy, the 2nd bedroom with its own wall of closets and built-ins offers flexibility for guests and office space with an adjacent 2nd tile bathroom. Additionally featuring central air, garage parking, and parquet floors. Highlights of the commo

$750,000

2 beds2 baths1,300 sq ft

99 Pond Ave #220, Brookline, MA 02445

$1,145 HOA • Garage • Community pool

77 Pond Ave #312, Brookline, MA 02445
77 Pond Ave #312, Brookline, MA 02445
77 Pond Ave #312, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Urban living at its finest in Brookline! Spacious one-bedroom unit with hardwood floors and central air conditioning. Enjoy the convenience of heated garage parking. The Brook House offers exceptional amenities, including onsite management, 24/7 security, a heated outdoor pool, a state-of-the-art fitness center (with steam room, sauna, weight room, and yoga studio), a resident lounge, tennis and basketball courts, and BBQ areas. Ideally located near the T (D/E lines), Brookline Village, Coolidge Corner, the Longwood Medical Area, Fenway, shopping, dining, and adjacent to Leverett Pond. Ideal for both homeowners and investors. Take advantage of unparalleled amenities and a prime location&mda

$509,000

1 bed1 bath710 sq ft

77 Pond Ave #312, Brookline, MA 02445

$1,130 HOA • Garage • Community pool

44 Washington St #713, Brookline, MA 02445
44 Washington St #713, Brookline, MA 02445
44 Washington St #713, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Welcome to this fully renovated studio at The Brook House, ideally situated just steps from Brookline Village T Station, offering effortless access to the Longwood Medical Area, downtown Boston, and nearby universities. The kitchen has been thoughtfully renovated with new ceramic porcelain floor tiles, brand-new stainless steel appliances, including a gas stove, dishwasher, microwave, and refrigerator with an ice maker plus all new cabinetry, quartz countertops, a marble backsplash, and lightings. The bathroom has also been renovated, featuring new ceramic floor and wall tiles, New flooring has been installed throughout the unit. The Brook House is a well-maintained, full-service building w

$469,900

0 beds1 bath500 sq ft

44 Washington St #713, Brookline, MA 02445

$520 HOA • Community pool • Walker's paradise

22 Chestnut Pl #111, Brookline, MA 02445
22 Chestnut Pl #111, Brookline, MA 02445
22 Chestnut Pl #111, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Enjoy the best of urban living in this beautifully landscaped property near Longwood Medical Area, Brookline Village, Coolidge Corner, Brookline Hills T stop, shops, restaurants, Jamaica Pond, and the Emerald Necklace. This oversized 900 sq ft one-bedroom, 1.5 bath home in desirable Sargent Estates features a renovated kitchen that opens to a spacious living/dining area—ideal for entertaining. Large windows fill the home with natural light, enhanced by wood flooring and ample closet space. The updated baths include stylish tile, modern fixtures, and contemporary lighting. Professionally managed building with full amenities: concierge service, seasonal outdoor pool with lifeguard, saun

$569,000

1 bed1.5 baths901 sq ft

22 Chestnut Pl #111, Brookline, MA 02445

$467 HOA • Community pool • Very walkable

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99 Pond Ave #608, Brookline, MA 02445
99 Pond Ave #608, Brookline, MA 02445
99 Pond Ave #608, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Discover your urban oasis in Brookline! Newly updated, a spacious 1-bedroom unit offers breathtaking courtyard views, a beautifully modern kitchen & bath, gleaming hardwood floors, and central AC. Heated garage parking adds convenience. The Brook House redefines luxury living with onsite management, 24/7 security, a heated outdoor pool, extensive gym (steam/sauna, weight room, yoga studio), resident lounge, tennis/basketball courts, and BBQ areas. Enjoy an A+ location near the T (D/E lines), Brookline Village/Coolidge Corner, Longwood Medical Area, Fenway, shops, and restaurants, adjacent to Leverett Pond & the Emerald Necklace. Perfect for homeowners & investors. Experien

$579,000

1 bed1 bath765 sq ft

99 Pond Ave #608, Brookline, MA 02445

$787 HOA • Garage • Community pool

33 Pond Ave Ph 1208, Brookline, MA 02445
33 Pond Ave Ph 1208, Brookline, MA 02445
33 Pond Ave Ph 1208, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Experience elevated living in this fully renovated two bedroom, two level penthouse spanning 1,840 sq. ft. Thoughtfully redesigned for modern luxury, this home features a sleek chef’s kitchen, expansive open-concept living/dining area with soaring ceilings, recessed lighting, red oak floors, and sweeping views from oversized windows. Dual-level access adds convenience, while a private rooftop terrace offers your own urban oasis. Both bedroom suites boast elegant ensuite baths, generous closets, and custom window treatments. Enjoy resort-style amenities including a heated Olympic-style pool, fitness center, tennis courts, BBQ patio, resident lounge, 24-hour security, and two-car garage

$999,000

2 beds2.5 baths1,840 sq ft

33 Pond Ave Ph 1208, Brookline, MA 02445

22.96 acre lot • $1,901 HOA • 2 garage spots

Property at 44 Washington St #917, Brookline, MA 02445, 1 bed, 1 bath

$499,999

1 bed1 bath705 sq ft

44 Washington St #917, Brookline, MA 02445

Property at 99 Pond Ave #326, Brookline, MA 02445, 1 bed, 1 bath

$569,000

1 bed1 bath870 sq ft

99 Pond Ave #326, Brookline, MA 02445

Property at 77 Pond Ave Spot 478, Brookline, MA 02445

$200,000

— beds— baths— sq ft

77 Pond Ave Spot 478, Brookline, MA 02445

Property at 44 Washington St #1104, Brookline, MA 02445, 1 bed, 1 bath

$599,000

1 bed1 bath710 sq ft

44 Washington St #1104, Brookline, MA 02445

Property at 44 Washington St #1208, Brookline, MA 02445, 1 bath

$409,000

0 beds1 bath500 sq ft

44 Washington St #1208, Brookline, MA 02445

Property at 33 Pond Ave Ph 1207, Brookline, MA 02445, 2 beds, 2.5 baths

$899,900

2 beds2.5 baths1,800 sq ft

33 Pond Ave Ph 1207, Brookline, MA 02445

Property at 99 Pond Ave #706, Brookline, MA 02445, 2 beds, 2 baths

$695,000

2 beds2 baths975 sq ft

99 Pond Ave #706, Brookline, MA 02445

Property at 33 Pond Ave #419, Brookline, MA 02445, 2 beds, 2 baths

$825,000

2 beds2 baths1,270 sq ft

33 Pond Ave #419, Brookline, MA 02445

Property at 99 Pond Ave #802, Brookline, MA 02445, 2 beds, 2 baths

$999,999

2 beds2 baths1,855 sq ft

99 Pond Ave #802, Brookline, MA 02445

Property at 77 Pond Ave #805, Brookline, MA 02445, 2 beds, 2 baths

$799,000

2 beds2 baths1,265 sq ft

77 Pond Ave #805, Brookline, MA 02445

Property at 60 Cameron St #2, Brookline, MA 02445, 3 beds, 2 baths

$1,599,000

3 beds2 baths1,448 sq ft

60 Cameron St #2, Brookline, MA 02445

Property at 44 Washington St #611, Brookline, MA 02445, 1 bath

$395,000

0 beds1 bath500 sq ft

44 Washington St #611, Brookline, MA 02445

Property at 111 Davis Ave #1, Brookline, MA 02445, 3 beds, 2 baths

$1,295,000

3 beds2 baths1,415 sq ft

111 Davis Ave #1, Brookline, MA 02445

Average home prices near High Street Hill, MA

Cities

Neighborhoods

South End homes for sale
$1,295,000
Dorchester homes for sale
$724,800
Jamaica Plain homes for sale
$799,000
Roslindale homes for sale
$749,950
Brighton homes for sale
$725,000
Back Bay homes for sale
$2,100,000
Roxbury homes for sale
$732,000
Allston homes for sale
$643,800
Chestnut Hill homes for sale
$3,074,000
Coolidge Corner homes for sale
$1,425,000

High Street Hill, MA real estate trends

$2.48M

Sale price

+269.4%
since last year

$799

Sale $/sq ft

+12.9%
since last year

Under list price

2.2%

Days on market

Down payment

100.0%

Total homes sold

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