Milton Real Estate

Milton is located between the Neponset River and the Blue Hills just 10 miles south of Boston by car. At 13.3 square miles with 27,000 residents, Milton is a densely populated South Shore suburb. Despite its convenient location and growing population, Milton still has a bucolic feel. Commercial development is limited and pristine estates are interspersed with protected land and parks. Much of the community’s appeal stems from its safe neighborhoods, friendly residents and top-ranked schools — both public and private. Not surprisingly, Money Magazine has repeatedly included Milton on its annual list of “Best Places to Live” in the United States. Given its historic past, Milton still retains many 19th century country homes and estates as well as early 19th century workers’ housing. Field stone walls forming property boundaries are a fixture on many lots. Many notable homes are on the Historic Register with the Milton Historical Commission creating six different historic districts within the town: Milton Center, Scotts Woods, Brush Hill, Milton Hill, Railway Village, and Milton Cemetery.  Read more about Milton real estate.

Milton Homes & Condos For Sale

Milton Homes & Condos For Sale September 29, 2023
37
Listed
80
Avg. DOM
$532.64
Avg. $ / Sq.Ft.
$950,000
Med. List Price
37 Properties
Page 1 of 4
6
Beds
8F21/2
Baths
15,491
Sq.Ft.
1890
Year Built
24
Days on Site
73155682
MLS
Applecroft, located in the Blue Hills of Milton, Massachusetts, is a nationally recognized, 1890's shingle-style country estate situated on 8.5 pastoral acres. The property has been fully restored...
10
Beds
5F11/2
Baths
7,761
Sq.Ft.
1810
Year Built
134
Days on Site
73114196
MLS
Enjoy total privacy, inside Route 128, in a stunning setting atop Brush Hill Road. On market for first time in 125 years! The main residence with 10 bedrooms and 5 ensuite baths is ready to restore...
8
Beds
4F11/2
Baths
9,100
Sq.Ft.
1860
Year Built
12
Days on Site
73160689
MLS
Sprawling estate on almost 2 acres tucked down a tree-lined drive off Milton's prestigious Brush Hill Rd. This 6,919 square foot home exudes opulence and old-world charm with its arched stairways,...
Open 9/30
52 Ford Ranch Rd Milton,  MA 02186
4
Beds
2F11/2
Baths
6,212
Sq.Ft.
1965
Year Built
5
Days on Site
73163063
MLS
FIRST OFFERING! Custom-built sprawling ranch, on a private ended way nestled in prestigious Historic Hillside neighborhood HNA. Designed by the award-winning founder of Domain Home Furnishings and...
5
Beds
4F11/2
Baths
4,473
Sq.Ft.
1973
Year Built
51
Days on Site
73147087
MLS
Welcome to the historic Scott's Woods neighborhood. What truly sets this fine home apart is its location. Nestled in a hidden gem of a neighborhood, this enclave remains one of Milton's most closely...
Open 9/30
50 Wolcott Woods Lane #50 Milton,  MA 02186
2
Beds
2F11/2
Baths
2,500
Sq.Ft.
2023
Year Built
256
Days on Site
73071151
MLS
One of only two remaining free-standing Adams at Award Winning Wolcott Woods, suburban Boston's premier 55+ neighborhood. This coveted detached design nestled privately in the woods with its own...
Open 9/30
50 Wolcott Woods Lane #50 Milton,  MA 02186
2
Beds
2F11/2
Baths
2,500
Sq.Ft.
2023
Year Built
192
Days on Site
73090319
MLS
One of only two remaining free-standing Adams at Wolcott Woods, suburban Boston's premier 55+ neighborhood. This coveted detached design is sure to make a statement with its lovely front entrance...
Open 9/30
139 Gerald Road Milton,  MA 02186
4
Beds
3F11/2
Baths
3,767
Sq.Ft.
1994
Year Built
4
Days on Site
73163654
MLS
Eureka! Your search has ended! This fantastic Colonial on a cul-de-sac in the heart of the Cunningham Park area has everything on your wish list! The first floor has a gracious foyer with a guest...
$1,635,000
Condo: Wolcott Woods
3
Beds
3F11/2
Baths
2,816
Sq.Ft.
2023
Year Built
18
Days on Site
73158282
MLS
Richly appointed, thoughtfully sited, and surrounded by nature, Wolcott Woods, suburban Boston's premier 55+ community, offers a portfolio of floorplans to suit today's lifestyles. The classic side...
Open 9/30
43 Wolcott Woods Lane #43 Milton,  MA 02186
$1,575,000
Condo: Wolcott Woods
3
Beds
3F11/2
Baths
2,576
Sq.Ft.
2023
Year Built
327
Days on Site
73055923
MLS
Enjoy the convenience of ready access to major highways and public transportation and a comfortable lifestyle, enhanced by the seasonal splendors that this magnificent estate setting affords. Only...
$1,575,000
Condo: Wolcott Woods
3
Beds
3F11/2
Baths
2,576
Sq.Ft.
2023
Year Built
18
Days on Site
73158309
MLS
Enjoy the convenience of ready access to major highways and public transportation and a comfortable lifestyle, enhanced by the seasonal splendors that this magnificent estate setting affords. Only...
$1,535,000
Condo: Wolcott Woods
3
Beds
3F11/2
Baths
2,576
Sq.Ft.
2023
Year Built
389
Days on Site
73032706
MLS
The classic shingle-style Draper design at Wolcott Woods, suburban Boston's premier 55+ community, lives like a vacation home while providing year-round enjoyment. Stepping from a charming front...

More About Milton Real Estate

Milton Location

Milton’s easy commute times to Boston by car and via the Red Line on the MBTA and commuter rail are a major part of its draw. In fact, Milton maintains four stops along the Mattapan-Ashmont Red Line Trolley. The community is bordered by Boston neighborhoods Dorchester and Mattapan to the north; Hyde Park (Boston) to the west; Quincy to the east and south; Randolph to the south; and Canton to the west. Milton is also easily accessed from I-93 and U.S. Route 1 as well as Route 3, which loop around the town near the southern and eastern borders.

Milton Recreation

Milton offers an abundance of activities for families. The Blue Hills Reservation, a 7,000-acre state park, is tops on many locals’ list. The Reservation stretches from Quincy to Dedham and from Milton to Randolph and houses 16 historic structures as well as a variety of trails and natural landscapes. The top of the hills offer sweeping views of the Boston cityscapes. The Blue Hill Observatory is also in the park and is the oldest continually operated weather observatory in the U.S. Another park attraction is Houghton’s Pond, which was formed 10,000 years ago from receding glaciers. The 24-acre pond is up to 42 feet deep in some areas providing numerous opportunities for swimming, fishing, and picnicking along its scenic shores. The Neponset River Reservation is another place to enjoy views of the river and natural beauty of many protected areas.

Milton History

The Puritans settled Milton as part of Dorchester in the 1630s with many of the early Puritan families of Milton going on to take influential roles in the creation of the Massachusetts Bay Colony. Milton’s roots are grounded in an agrarian culture and variety of industries that sprang up along the Neponset River. In the 18th century Milton served as the site of the first chocolate factory in New England while expanding as an industrial area. The town was home to America’s first piano factory as well as helping to originate the term “cracker” for biscuits baked at Bent’s Cookie Factory. These concoctions made of flour and water were designed so they would not deteriorate during long sea voyages from the port of Boston. The “crackling” noise occurred during the baking process, giving birth to the name. Today Milton claims many notable residents — the town was President George H.W. Bush’s birthplace and home to former Governor Deval Patrick as well as being the town of record for many New England athletes, actors, authors, and statesmen.

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