Prevu by reAlpha
BuySellBlogBrowse Listings

55 Parkwood DriveMilton, MA 02186

For Sale

$5,995,000

Smart Buyer Rebate $29,975

Experience the pinnacle of Milton living at this 1915 French Colonial masterpiece. Set on nearly three acres at the foot of the Blue Hills Reservation, this legacy estate offers a rare blend of privacy and prestige. The grounds are an entertainer’s dream, featuring an in-ground pool, pool house, and a two-story, five-bay garage with an attached vintage greenhouse. Spanning 9,000+ sq. ft., the residence boasts seven bedrooms, ten bathrooms, and nine fireplaces. The main level offers grand formal spaces, including a mahogany-paneled library and a sophisticated office. The chef’s culinary suite is a masterwork of marble and high-end gas ranges. Retreat to the palatial primary wing—a four-room haven with dual baths and expansive views. The finished lower level adds versatility with twin fitness studios and a private lounge and office. Located eight miles from Boston and Logan, enjoy a country-manor lifestyle near world-class Milton Academy. A rare architectural gem. Welcome home!

Listed by Kevin G. Keating

·

Keating Brokerage

·

617-699-7179

Last updated May 19, 2026

·

Source: MLSPin #73519804

Listing Facts

  • TypeSingle-family
  • NeighborhoodHillside Street
  • Bedrooms7
  • Bathrooms10
  • Days on Prevu32
  • Taxes$38,228/year
  • Size9,320 sqft
  • Price per sqft$643

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking
  • Swimming Pool

Location

Mortgage Calculator

Listing History

05/15/2026
Listed by Keating Brokerage
$5,995,000

Property Details for 55 Parkwood Drive

Association

Amenities

  • Community Features: Pool, Medical Facility, Bike Path, Conservation Area, Highway Access, House Of Worship, Private School, Public School

Exterior

Construction

  • Roof: Shingle
  • Window Features: Insulated Windows
  • Year Built: 1915
  • Year Built Details: Actual
  • Architectural Style: French Colonial
  • Construction Materials: Frame
  • Exterior Features: Porch, Deck - Wood, Balcony, Pool - Inground Heated, Rain Gutters, Professional Landscaping

Features

  • Patio And Porch Features: Porch, Deck - Wood
  • Pool Features: Pool - Inground Heated
  • Pool Private: Yes
  • Road Frontage Type: Public

Measurements

  • Building Area Total: 9,320
  • Building Area Units: Square Feet
  • Lot Features: Cleared, Gentle Sloping
  • Lot Size Acres: 2.77
  • Lot Size Area: 2
  • Lot Size Square Feet: 120,661
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: 133982
  • Tax Annual Amount: $38,228.00
  • Tax Assessed Value: $3,447,100.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Gas Water Heater, Range, Oven, Dishwasher, Disposal, Trash Compactor, Microwave, Indoor Grill, Refrigerator, Washer, Dryer, Range Hood
  • Fireplace Features: Dining Room, Living Room, Master Bedroom, Bedroom, Bath
  • Fireplace: Yes
  • Fireplaces Total: 9
  • Flooring: Wood, Tile, Carpet, Marble, Stone / Slate, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
  • Interior Features: Closet/Cabinets - Custom Built, Recessed Lighting, Bathroom - Full, Bathroom - Tiled With Shower Stall, Steam / Sauna, Closet, Library, Home Office, Exercise Room, Game Room, Home Office-Separate Entry, Sitting Room, Sauna/Steam/Hot Tub

Measurements

  • Living Area: 9,320
  • Living Area Source: Measured

Rooms

  • Basement: Full, Finished, Walk-Out Access, Garage Access
  • Bathrooms Full: 7
  • Bathrooms Half: 3
  • Bathrooms Total Integer: 10
  • Bedrooms Total: 7
  • Rooms Total: 12

Parking

Parking

  • Attached Garage: Yes
  • Covered Spaces: 6
  • Garage Spaces: 6
  • Garage: Yes
  • Open Parking Spaces: 15
  • Open Parking: Yes
  • Parking Features: Attached, Detached, Under, Garage Door Opener, Paved Drive, Off Street, Tandem, Paved
  • Parking Total: 21

Utilities

Equipment

  • Cooling: Central Air, 3 Or More
  • Has Cooling: Yes
  • Electric: Circuit Breakers, 200+ Amp Service
  • Heating: Baseboard, Natural Gas, Fireplace(s), Fireplace
  • Has Heating: Yes
  • Laundry Features: Laundry Closet, Electric Dryer Hookup, Washer Hookup, First Floor
  • Sewer: Public Sewer
  • Utilities: For Electric Range, For Electric Oven
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 7 bedrooms and 10 bathrooms in this single-family home at 55 Parkwood Drive.

Does this single-family home have parking?

Yes, there are 6 parking spaces available for 55 Parkwood Drive.

What are the annual taxes for 55 Parkwood Drive?

Annual taxes for this single-family home are estimated at $38,228.

How does 55 Parkwood Drive compare to other single-family homes in Hillside Street?

This single-family home is listed 126% above the average price for single-family homes in Hillside Street and has been on the market for 22 more days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 9,320 sqft.

55 Parkwood Drive is a 7-bedroom, 10-bath single-family home for sale in Milton MA 02186. Available on Prevu for 32 days at $5,995,000. This home features 9,320 square feet of living space, located in Norfolk County. The median listing price for single-family homes in this area is $2,999,999. Additional amenities include private outdoor space, dishwasher, air conditioning, parking, swimming pool, and washer/dryer. Explore more single-family home listings in Norfolk County.

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.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.