High Street Hill, MA homes for sale & real estate

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3D WALKTHROUGH

71 Highland Rd, Brookline, MA 02445
71 Highland Rd, Brookline, MA 02445
71 Highland Rd, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Welcome to this delightful single family nestled in the heart of Pill Hill’s Historic District! Adorned with gleaming hardwood floors throughout, plenty of windows that bathe the space in natural light! Located directly across the street from Harry Downes Field, featuring athletic fields, a running track, playground, and dog park. Just beyond lies the Muddy River, part of Olmsted Parkway, that connects to Jamaica Pond. This delightful 3-bed & 1-bath home is perfect for first-time homebuyers! w/ a beautiful deck & yard that is perfect for entertaining or to let the kids/dogs run. The home is situated within the highly regarded Lincoln School district, Brookline High School

$1,100,000

3 beds1 bath1,000 sq ft

71 Highland Rd, Brookline, MA 02445

2,248 sq ft lot • Very walkable

3D WALKTHROUGH

81 Glen Rd Unit S2, Brookline, MA 02445
81 Glen Rd Unit S2, Brookline, MA 02445
81 Glen Rd Unit S2, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Gorgeous corner townhouse offers abundant natural light, privacy, and gracious living with a stunning architecturally significant curved glass wall and tremendous high ceilings. Floor-to-ceiling builtins and recessed lighting lend sophistication and charm. The bespoke kitchen with beautiful glass-front cabinetry, porcelain white farmer's sink, induction stove, and glass tile backsplash is complemented by stunning crystal blue quartzite counters. Dine al fresco outside the kitchen on the private deck with . The second floor features a skylit staircase, spacious master bedroom with custom en suite bath, two additional bedrooms and a family bath. Extra exclusive storage, in-unit laundry, and 2

$1,049,000

3 beds2 baths1,340 sq ft

81 Glen Rd Unit S2, Brookline, MA 02445

$1,420 HOA • Very walkable

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

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

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

$1,339,999

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

6 Juniper St #16, Brookline, MA 02445
6 Juniper St #16, Brookline, MA 02445
6 Juniper St #16, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Top-floor 3BR condo on a quiet gated cul-de-sac in Brookline Village. Freshly painted with granite kitchen, stainless appliances, marble-tiled bath, hardwood floors, and four-season sunroom. Laundry in complex. Enjoy use of Brook House pool two days a week. Steps to Longwood Medical, T, Fenway, shops, and restaurants. Well-maintained building in unbeatable location.

$729,000

3 beds1 bath939 sq ft

6 Juniper St #16, Brookline, MA 02445

$742 HOA • Walker's paradise

77 Pond Ave #1207, Brookline, MA 02445
77 Pond Ave #1207, Brookline, MA 02445
77 Pond Ave #1207, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Stunning 12th-floor 1BR/1BA unit with beautiful updates and breathtaking views. This bright and airy home features a well-appointed kitchen with granite countertops, gas cooking, and nearly new (1 year old) stainless steel appliances. Gleaming refinished wood floors run throughout, adding warmth and sophistication. Enjoy sunsets and skyline views from the large private balcony, with abundant natural light pouring in through expansive picture windows. Includes 1 garage parking. Located in highly desirable Brook House, offering resort-style amenities: Olympic-size heated pool, indoor/outdoor fitness centers, tennis, basketball & pickleball courts, grilling areas, 24-hour security, and m

$585,000

1 bed1 bath860 sq ft

77 Pond Ave #1207, Brookline, MA 02445

$847 HOA • Garage • Community pool

26 White Pl #3, Brookline, MA 02445
26 White Pl #3, Brookline, MA 02445
26 White Pl #3, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Charming brick path leads to a unique find in Brookline Village @ 26 White Place #3. The townhouse provides open living space, a stunning chefs kitchen, Viking appliances & solid stone counters. Open dining area & fireplaced living room with hard wood floors, and custom built-in shelving & cabinets. The 2nd level features 2 well proportioned bedrooms, with a white tiled full bath with shower & tub. Primary bedroom/bath suite sits at the top of the townhouse. Windows & skylights provide beautiful natural light, a private bath with shower, ample closet space, add'l room for a cozy sitting area to read & relax and enjoy the tree top views. Basement with abun

$1,150,000

3 beds2 baths1,345 sq ft

26 White Pl #3, Brookline, MA 02445

$489 HOA • Walker's paradise

22 Chestnut Pl #608, Brookline, MA 02445
22 Chestnut Pl #608, Brookline, MA 02445
22 Chestnut Pl #608, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Welcome to Sargent Estates Manor! This spacious one-bedroom plus den condo includes a deeded parking space and offers the comfort and convenience you’ve been looking for. Enjoy a beautifully maintained building with elevator, concierge, professional management, and elegant lobby. Amenities include an in-ground pool, sauna, large function room with kitchen, landscaped grounds, laundry on every floor, and bike storage. Ideally located near the T, bus lines, and the Longwood Medical Area. Just a short stroll to local shops, a mini-mart, and everything vibrant Brookline has to offer.

$569,888

1 bed1.5 baths774 sq ft

22 Chestnut Pl #608, Brookline, MA 02445

$503 HOA • Community pool • Very walkable

OPEN SAT, 11:30AM TO 1PM

58 Prince St #1, Brookline, MA 02445
58 Prince St #1, Brookline, MA 02445
58 Prince St #1, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Charm, convenience and functionality abound in this 2-bed 2-bath condo in Brookline Village! Airy open-concept living, high ceilings and a private deck make this modern 1st-floor home perfect for first-time buyers and investors alike. The updated kitchen has granite counters and ample storage with easy access to the back deck for morning coffee! The spacious main living area offers plenty of room for dining and living areas, plus a convenient laundry closet. A primary suite is tucked into the back of the home, with two sizable closets and an ensuite bath. The second bedroom is at the opposite end of the condo with plentiful natural light from windows on two sides. The second full bathroom h

$788,000

2 beds2 baths980 sq ft

58 Prince St #1, Brookline, MA 02445

$258 HOA • Community pool • Very walkable

91 Chestnut St #4, Brookline, MA 02445
91 Chestnut St #4, Brookline, MA 02445
91 Chestnut St #4, Brookline, MA 02445
ABOUT THIS HOME
High Street Hill, MA Homes for Sale
Location, location! This exceptional 2 Bedroom condo with Deeded Parking space 10 and Low HOA on a quiet street in the wonderful neighborhood, close to the Medical Area. This beautiful unit features a large living room, lots of sunlight with great layout for entertaining, freshly painted, nice hardwood floors throughout, tiled bathroom, separate Eat-In Kitchen with stainless steel appliances, and IN-UNIT LAUNDRY. Steps away to Lincoln School, BHS, public transport (D line), restaurants, stores, parks, and hospitals.

$599,000

2 beds1 bath718 sq ft

91 Chestnut St #4, Brookline, MA 02445

$423 HOA • Very walkable

Property at 33 Pond Ave #603, Brookline, MA 02445, 2 beds, 2 baths

$799,999

2 beds2 baths1,005 sq ft

33 Pond Ave #603, Brookline, MA 02445

Property at 77 Pond Ave #312, Brookline, MA 02445, 1 bed, 1 bath

$509,000

1 bed1 bath710 sq ft

77 Pond Ave #312, Brookline, MA 02445

Property at 44 Washington St #713, Brookline, MA 02445, 1 bath

$469,900

0 beds1 bath500 sq ft

44 Washington St #713, Brookline, MA 02445

Property at 99 Pond Ave #608, Brookline, MA 02445, 1 bed, 1 bath

$569,000

1 bed1 bath765 sq ft

99 Pond Ave #608, Brookline, MA 02445

Property at 33 Pond Ave Ph 1208, Brookline, MA 02445, 2 beds, 2.5 baths

$999,000

2 beds2.5 baths1,840 sq ft

33 Pond Ave Ph 1208, Brookline, MA 02445

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

$495,000

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

$555,000

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 #1208, Brookline, MA 02445, 1 bath

$399,999

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 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

Average home prices near High Street Hill, MA

Cities

Neighborhoods

South End homes for sale
$1,285,000
Dorchester homes for sale
$757,000
Jamaica Plain homes for sale
$839,000
Roslindale homes for sale
$777,500
Brighton homes for sale
$679,000
Back Bay homes for sale
$1,934,000
Roxbury homes for sale
$749,900
Allston homes for sale
$669,000
Chestnut Hill homes for sale
$3,525,000
Coolidge Corner homes for sale
$1,250,000

High Street Hill, MA real estate trends

$1.15M

Sale price

-33.9%
since last year

$883

Sale $/sq ft

+5.2%
since last year

Over list price

9.7%

Days on market

Down payment

100.0%

Total homes sold

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