Browse All Milton MA 5 Bedroom Properties for Sale

5 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 73593368 MLS ⋅ 6,768 SqFt.

A life without compromise awaits at 44 Ridgewood Rd in Milton, where exceptional new construction pairs architectural presence with thoughtful everyday ease. A grand kitchen, butler’s pantry, and dedicated dining room set the stage for memorable entertaining, while the dramatic living room impresses with soaring ceilings, expansive windows, and a commanding fireplace. A first-floor office/bedroom with ensuite bath adapts to changing needs. A mudroom off the two-car garage and designer powder room complete the main level. The luxurious primary suite offers two separate closets and an expansive, spa-inspired bath; every secondary bedroom features its own ensuite. With 9-foot ceilings, the finished lower level offers generous entertainment spaces, a wet bar, gym, sauna, full bath, and flexible office/guest space. An expansive deck overlooks the private backyard. From milestone celebrations to quiet mornings, this distinctive Milton home makes room for every part of life.

44 Ridgewood Rd, Milton

$999,000

5 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73585240 MLS ⋅ 2,244 SqFt.

As you enter 60 Sassamon Avenue, you'll be welcomed by high ceilings, a fireplaced living room, newly refinished hardwood floors and three levels of living space. The current owners have completed numerous updates over the past five years, including a new furnace, new water heater, replacement windows and a refreshed kitchen featuring stainless steel appliances, new countertops and new flooring. With five bedrooms, two full baths and one-half bath, this charming Colonial offers ample space and flexibility for today's lifestyle. The expansive family room is sure to become a favorite gathering place, featuring new flooring, a vaulted ceiling with skylights, and direct access to the back deck and backyard. The first floor also includes a formal dining room, a versatile bedroom that could serve as a home office or playroom, a full bath with a shower, a convenient laundry room as well as a powder room. The second floor offers two bedrooms, an additional room ideal for a nursery or home office, and a full bath. Located on second floor there’s a balcony off the small room offering a wonderful view and often beautiful sunsets. On the third floor, there are two newly carpeted bedrooms, providing private and comfortable living space. Set on an oversized lot, the property also features a private side entrance leading to the finished lower level, ideal for a home gym, office, media room, or playroom. The basement is also accessible from the kitchen. The generous side yard provides exceptional outdoor space for recreation, gardening, or entertaining while offering potential opportunities for future expansion. Connected to the garage, built in 2011, there's a heated "bonus room", providing valuable flex space for hobbies, work, recreation, or a private retreat. Above the garage, you'll find abundant storage space, providing room for seasonal items, equipment & household belongings. Nestled at the base of the Blue Hills Reservation, this highly sought-after neighborhood is known for its generous lot sizes, strong sense of community & homes that have been thoughtfully expanded and improved over the years. Conveniently located near Routes 128/I-95 and 24, the property offers an easy commute to Boston and points south, while University Station while University Station & Route 128 Amtrak station are less than eight miles away. If you're hoping to be settled into your new home by the holiday season, come by and fall in love with 60 Sassamon Avenue. You'll be glad you did!

60 Sassamon Ave, Milton

$1,395,000

5 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73581557 MLS ⋅ 2,670 SqFt.

Lovingly restored and beautifully maintained, this stunning Victorian seamlessly blends timeless architectural character with modern comfort. Soaring ceilings, gracious proportions, and abundant natural light create an open and airy feel throughout, while carefully preserved period details add warmth, charm, and a sense of history at every turn. Offering three substantial floors of living space, the home provides exceptional flexibility for today's lifestyle, with inviting gathering spaces, comfortable private retreats, and room to grow, work, and entertain. The thoughtful layout flows effortlessly from room to room, creating an atmosphere that is both elegant and welcoming. Step outside to an entertaining-sized yard, perfect for summer barbecues, outdoor celebrations, gardening, or simply relaxing with family and friends. An oversized two-car garage adds convenience and ample storage, a rare and valuable feature. Ideally situated just a short stroll from boutique shops, popular restaurants, cafés, and everyday conveniences, this special home offers the perfect blend of historic beauty and walkable living. Rich in character, beautifully restored, and ideally located, this Victorian is a rare opportunity to enjoy the charm of a bygone era with all the comforts of today.

47 Washington St, Milton

$999,000

5 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73579278 MLS ⋅ 2,462 SqFt.

Motivated seller - don't miss out! This is the best opportunity in Milton. 27 Glendale Road has an updated kitchen, with large island, stainless steel appliances & an open concept dining area.Close to Milton Schools & Cunningham Park.Plus, a spacious primary suite with large close and glass enclosed shower stall. Also, this home has Central AC, 5 bedrooms, a partially finished basement and a one car garage. Lastly, this home has an in ground pool!Ready for new owners!!

27 Glendale Road, Milton

$1,195,000

5 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73578075 MLS ⋅ 2,184 SqFt.

A hidden gem in the Columbines, 19 Gaskins Road is set among mature trees and flowering woodland perennials on a private road. This gracious 5 bedroom Crosby-built home on 9500+ s.f. lot is not your typical center entrance colonial. From the stately columns at the front and side porches, to the triple windows in the living and dining rooms, to the graceful ‘Good Morning’ staircase and striking architectural details, this handsome home exudes character and charm. The large entrance hall opens to a flowing floor plan ideal for entertaining, with a light-filled, fireplaced living room and small library with a second fireplace. The kitchen is open to the generous dining area, and both kitchen and dining room access the porch. The second floor boasts four large corner bedrooms with sizeable closets, plus a bonus extra bedroom or home office. The enormous attic contains an oversized cedar closet and ample room for expansion. Downstairs, the walk-out basement is partially finished and offers potential for a wine cellar or greenhouse. Screened by shade trees in the warmer months, the backyard is large enough for games or a future patio and outdoor kitchen, while the deep, covered side porch provides for sheltered al fresco dining. Within walking distance of Turner’s Pond, schools, trolley, bike path, and Lower Mills shops and dining, this is the Columbines house you’ve been waiting for.

19 Gaskins Road, Milton

$11,900,000

5 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 73570207 MLS ⋅ 10,000 SqFt.

Privately gated and exquisitely appointed, 540 Harland Street presents a rare opportunity to own an extraordinary equestrian estate set on approximately 8 acres within the Blue Hills Reservation. Surrounded by protected natural beauty and offering direct riding access to approximately 7,000 acres of preserved landscape, this exceptional property combines complete privacy, sophisticated living, and an unparalleled connection to the outdoors—yet remains conveniently close to Boston.The approximately 8,250-square-foot main residence is designed for grand-scale living and effortless entertaining, featuring five bedrooms, five full baths, and two half baths, complemented by soaring 10-foot ceilings throughout. The spectacular chef’s kitchen is outfitted with premium Wolf appliances, while a dedicated home gym and state-of-the-art home theater elevate the everyday experience. An in-home elevator provides seamless access throughout the residence.Outdoor living is equally impressive, with a 350-square-foot patio and a fully equipped Wolf outdoor kitchen, creating an exceptional setting for entertaining, dining, and enjoying the surrounding landscape.The estate’s remarkable carriage house adds an extraordinary layer of versatility, offering an 8–16+ car garage and approximately 1,750 square feet of guest living space above. Ideal for car enthusiasts, collectors, guests, or extended family, this separate structure provides an exceptional combination of utility and luxury.At the heart of the property’s equestrian amenities is an approximately 2,000-square-foot state-of-the-art multi-stall equestrian center, thoughtfully complemented by an adjacent exercise pen. The direct access to miles of protected Blue Hills terrain allows riders to leave the property on horseback and immediately experience one of the region’s most spectacular natural settings.This is far more than a luxury residence—it is a private equestrian compound and lifestyle estate, offering an extraordinary level of scale, privacy, amenities, and access to protected land rarely found in Greater Boston. A truly distinctive retreat where refined living and the freedom of the countryside exist in perfect harmony.

540 Harland St, Milton

$2,750,000

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73560323 MLS ⋅ 5,300 SqFt.

Welcome to your brand new construction home in the beautiful town of Milton. Thoughtfully designed with over 5,300 square feet of refined living space, this custom built residence offers 5 bedrooms, 4 full baths, 2 half baths & an attached 2 car garage w/ extra storage. Entering through the arched front doorway you are greeted by an extensive open layout w/ high ceilings, natural light, a spacious dining room, and an oversized chef's kitchen featuring: taj mahal quartz counters, Thermador panelized appliances, a custom built venetian plaster vent hood, Mouser custom cabinetry & a massive pantry w/ a custom built door for easy loading direct from the garage. The 1st floor continues w/ a large living room area including a venetian plaster electric fireplace, custom built-ins, an extra office or 1st floor bedroom flex space. The second level features a stunning primary suite bedroom w/ a parquet ipe private deck & a spa-inspired en-suite bath w/ a large wet-room shower and tub. Three guest bedrooms all include walk in closets and hardwood flooring. A dedicated laundry room and two more full baths complete the 2nd floor. The finished lower level offers flexible space for a media room, playroom, home gym area, wellness center, and/or an extra bedroom w/ a full bath. The exterior includes a fully landscaped yard, composite privacy fence, a massive Ipe deck, and irrigation. A 1 year builder warranty is included as well. Come see this custom designed home built by one of the best custom home builders in the area!

33 Harbor View Park, Milton

$4,800,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73551180 MLS ⋅ 4,310 SqFt.

Set off a lovely cul-de-sac, this restored Greek Revival sits on 4+ acres of open field, rare this close to Boston, stretching out rather than closing in. The expansive field: open, level, and bordering the 7,000 acre Blue Hills Reservation, accessible and yours to explore. A buildable lot: room to expand, a family compound, simply hold as open space, you decide. Fine millwork and French doors speak to fine craftsmanship. The kitchen is anchored by top appliances and built for serious cooking. A well-appointed mudroom keeps the everyday beautifully managed. A glass-walled garden room with fireplace, woodland views and stillness. Modern systems (geothermal heating/cooling, solar array, EV charger) reflect a commitment to sustainability. Privacy and peace without sacrificing reach: commuter rail, Rts 128/95, and Logan Airport all close. Access to Milton's public and the area's prestigious independent schools. This is where sophistication, sanctuary, and the wide-open sky meet.

1632 Canton Ave, Milton

$3,200,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73511555 MLS ⋅ 4,310 SqFt.

Set off a lovely cul-de-sac, surrounded by woodland and sky, this restored Greek Revival offers grace, modern sustainability, and space for you and yours. Fine millwork and French doors speak to fine craftsmanship. The kitchen is anchored by top appliances and built for serious cooking. A well-appointed mudroom keeps the everyday beautifully managed: a quiet workhorse. A glass-walled garden room with fireplace and woodland views offers needed stillness. A bluestone terrace flows to the private trailhead into the Blue Hills Reservation: 7,000 acres for hiking or exploration. Modern systems — geothermal heating/cooling, solar array, and EV charger — reflect a commitment to sustainability. On 2+ acres of natural beauty, find privacy and peace without sacrifice: the commuter rail, Rts 128/95, Logan Airport within easy reach. Access to Milton's public and the area’s prestigious independent schools makes the address practical and inspiring. This is where sophistication and sanctuary meet.

1632 Canton Ave, Milton

$3,699,999

5 Beds ⋅ 7 Baths ⋅ EXTENDED Status ⋅ 73508385 MLS ⋅ 9,435 SqFt.

This fully renovated Georgian Colonial offers exceptional living and entertaining in one of Milton’s most desirable neighborhoods. Privately set at the end of a cul-de-sac in Indian Cliff Estates, the home sits on 1.88 acres with a three-car attached garage. The main level features an eat-in kitchen, formal dining room, and a gracious living room that flows into a sitting area. A dramatic family room with cathedral ceilings and a floor-to-ceiling stone fireplace anchors the home, complemented by a wet bar and direct access to the indoor heated pool and hot tub. An elegant foyer with a curved staircase leads to five well-appointed bedrooms. The expansive lower level offers multiple flex spaces, including a home gym, recreation rooms, and a private theater. Designed for both everyday living and memorable entertaining, this home delivers a rare blend of space, privacy, and resort-style amenities.

90 Countryside Ln, Milton

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

5 Bedroom Milton Real Estate

Our website features the best real estate search for 5 bedroom properties available in Milton and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Browse All Milton MA 5 Bedroom Properties for Sale

5 Bedroom Milton Real Estate

How much is your home worth?

How much is your home worth?