Nestled in Milton’s sought-after Hillside neighborhood, this exceptional Federal-style Colonial offers the perfect blend of classic charm, quality renovations, & ideal livability. Thoughtfully improved & meticulously cared for, the home offers 3400 sq ft of living space, including a floor-through living room, dining room, two inviting dens - with 8 ft ceilings, four fireplaces and windows galore. The sunlit kitchen opens to a breakfast nook and newly converted four-season sunroom, creating a natural connection to the outdoors. Upstairs offers four generously sized bedrooms including primary suite with en-suite bath and pristine family bath. A large and inviting family / bonus room with a gas fireplace and bar completes the lower level. Set on a private, professionally landscaped .92-acre lot, the outdoor setting is magnificent; with heated in-ground pool, expansive level lawn, and fenced privacy, this is a true lifestyle property and a turnkey opportunity for a forever home in Milton.
Sold for $2,215,000
$2,215,000
23 Parkwood Dr, Milton, MA 02186
4beds
3,418sqft
Single Family Residence
Built in 1967
0.92 Acres Lot
$2,232,600 Zestimate®
$648/sqft
$6,115 Estimated rent
Home value
$2,232,600
$2.08M - $2.39M
$6,115/mo
Zestimate® history
Owner options
List your home for rent
$6,115/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$6,115/mo
Rent Zestimate®
Refinance and save
$13,742/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$13,742/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Heated in-ground poolDining roomFenced privacyFour-season sunroomPristine family bathFour generously sized bedroomsExpansive level lawn
Zillow last checked:
Listing updated:
Listed by:
Peggy Gemelli 617-513-4802,
Gibson Sotheby's International Realty 781-444-8383
Bought with:
Andrew Mazzeo
All Star Realty, Inc.
Source: MLS PIN,MLS#: 73490877
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Features: Bathroom - 3/4, Bathroom - Double Vanity/Sink, Walk-In Closet(s), Flooring - Hardwood
- Level: Second
- Area: 266
- Dimensions: 14 x 19
Bedroom 2
- Features: Flooring - Hardwood
- Level: Second
- Area: 140
- Dimensions: 14 x 10
Bedroom 3
- Features: Flooring - Hardwood
- Level: Second
- Area: 169
- Dimensions: 13 x 13
Bedroom 4
- Features: Flooring - Hardwood
- Level: Second
- Area: 169
- Dimensions: 13 x 13
Primary bathroom
- Features: Yes
Bathroom 1
- Features: Bathroom - Half, Flooring - Stone/Ceramic Tile
- Level: First
Bathroom 2
- Features: Bathroom - 3/4, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Double Vanity, Recessed Lighting, Remodeled
- Level: Second
- Area: 56
- Dimensions: 8 x 7
Bathroom 3
- Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Recessed Lighting, Remodeled
- Level: Second
- Area: 84
- Dimensions: 12 x 7
Dining room
- Features: Closet/Cabinets - Custom Built, Flooring - Hardwood, Chair Rail, Lighting - Pendant, Crown Molding, Decorative Molding, Pocket Door
- Level: Main,First
- Area: 210
- Dimensions: 14 x 15
Family room
- Features: Flooring - Hardwood, Exterior Access, Remodeled, Slider, Crown Molding
- Level: Main,First
- Area: 187
- Dimensions: 11 x 17
Kitchen
- Features: Flooring - Hardwood, Pantry, Countertops - Stone/Granite/Solid, Breakfast Bar / Nook, Recessed Lighting, Stainless Steel Appliances, Gas Stove, Peninsula, Lighting - Pendant, Crown Molding, Pocket Door
- Level: Main,First
- Area: 132
- Dimensions: 12 x 11
Living room
- Features: Flooring - Hardwood, French Doors, Exterior Access, Crown Molding, Decorative Molding
- Level: Main,First
- Area: 540
- Dimensions: 20 x 27
Heating
- Central, Baseboard, Electric Baseboard, Natural Gas, Leased Propane Tank, Fireplace
Cooling
- Central Air
Appliances
- Included: Gas Water Heater, Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer, Range Hood, Wine Cooler, Plumbed For Ice Maker
- Laundry: Bathroom - Half, Flooring - Stone/Ceramic Tile, Stone/Granite/Solid Countertops, Main Level, Gas Dryer Hookup, Recessed Lighting, Washer Hookup, First Floor
Features
- Breakfast Bar / Nook, Recessed Lighting, Crown Molding, Decorative Molding, Closet, Cedar Closet(s), Ceiling Fan(s), Sunken, Den, Foyer, Bonus Room, Sun Room
- Flooring: Tile, Carpet, Hardwood, Flooring - Hardwood, Flooring - Wall to Wall Carpet, Flooring - Stone/Ceramic Tile
- Windows: Insulated Windows
- Basement: Full,Partially Finished,Garage Access,Concrete
- Number of fireplaces: 4
- Fireplace features: Family Room, Living Room
Interior area
- Total structure area: 3,418
- Total interior livable area: 3,418 sqft
- Finished area above ground: 2,860
- Finished area below ground: 558
Property
Parking
- Total spaces: 10
- Parking features: Attached, Garage Door Opener, Paved Drive, Off Street, Paved
- Attached garage spaces: 2
- Uncovered spaces: 8
Features
- Exterior features: Pool - Inground Heated, Rain Gutters, Storage, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard
- Has private pool: Yes
- Pool features: Pool - Inground Heated
- Fencing: Fenced/Enclosed,Fenced
Lot
- Size: 0.92 Acres
- Features: Wooded, Level
Details
- Parcel number: M:N B:012 L:7,133980
- Zoning: RA
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Concrete Perimeter
- Roof: Shingle
Condition
- Remodeled
- Year built: 1967
Utilities & green energy
- Electric: Circuit Breakers, 200+ Amp Service
- Sewer: Private Sewer
- Water: Public
- Utilities for property: for Gas Range, for Electric Oven, for Gas Dryer, Washer Hookup, Icemaker Connection
Community & HOA
Community
- Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Golf, Medical Facility, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station, University
- Subdivision: Hilllside / Scotts Woods
HOA
- Has HOA: No
Location
- Region: Milton
Financial & listing details
- Price per square foot: $648/sqft
- Tax assessed value: $1,230,300
- Annual tax amount: $13,644
- Date on market: 4/20/2026
- Exclusions: Dining Rm & Kitchen Chandeliers, Tvs, Refridgerator In Garage. Tv Wallmounts & Brackets To Stay.
Price history
| Date | Event | Price |
|---|---|---|
| 5/12/2026 | Sold | $2,215,000+18.1%$648/sqft |
Source: MLS PIN #73490877 Report a problem | ||
| 4/1/2026 | Contingent | $1,875,000$549/sqft |
Source: MLS PIN #73490877 Report a problem | ||
| 3/24/2026 | Listed for sale | $1,875,000+131.5%$549/sqft |
Source: MLS PIN #73490877 Report a problem | ||
| 8/31/2009 | Sold | $810,000+118.9%$237/sqft |
Source: Public Record Report a problem | ||
| 12/3/1990 | Sold | $370,000-22.8%$108/sqft |
Source: Public Record Report a problem | ||
| 4/1/1987 | Sold | $479,000$140/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $13,644 +4% | $1,230,300 +2.4% |
| 2024 | $13,119 +1.7% | $1,201,400 +6.2% |
| 2023 | $12,899 +3.1% | $1,131,500 +12.8% |
| 2022 | $12,507 -0.9% | $1,003,000 +4.3% |
| 2021 | $12,621 +0.4% | $961,200 +0.3% |
| 2020 | $12,569 +2.7% | $958,000 +3.2% |
| 2019 | $12,235 +10.4% | $928,300 +15.7% |
| 2018 | $11,080 +7% | $802,300 +5% |
| 2017 | $10,358 -2% | $763,900 -2.4% |
| 2016 | $10,568 +0% | $782,800 +3.3% |
| 2015 | $10,567 -4.4% | $758,000 +2.8% |
| 2014 | $11,052 +2% | $737,300 |
| 2013 | $10,838 +2.4% | $737,300 |
| 2012 | $10,580 -6.3% | $737,300 -8.1% |
| 2011 | $11,288 -2.3% | $802,300 -7.3% |
| 2010 | $11,550 +12.8% | $865,200 -0.8% |
| 2009 | $10,236 +3.5% | $871,900 -3.4% |
| 2008 | $9,888 +1% | $903,000 |
| 2007 | $9,789 +6.8% | $903,000 |
| 2006 | $9,165 +8% | $903,000 +12.2% |
| 2005 | $8,485 -0.7% | $805,000 +14.2% |
| 2004 | $8,541 +3.3% | $704,700 |
| 2003 | $8,266 -4.4% | $704,700 +37.6% |
| 2002 | $8,643 +19.3% | $512,300 +29.4% |
| 1999 | $7,247 | $395,800 |
Find assessor info on the county website
Neighborhood: 02186
Nearby homes
- $2,033,8004 bd2 ba3.2k sqft7 Parkwood Dr, Milton, MA 02186Off Market
- $1,950,2004 bd3 ba4k sqft39 Parkwood Dr, Milton, MA 02186Off Market
- $4,216,7005 bd5 ba7.6k sqft22 Parkwood Dr, Milton, MA 02186Off Market
- $--1 AcresCorner Hillside St-parkwood Dr, Milton, MA 02186Off Market
- $3,238,2005 bd-- ba6.1k sqft8 Parkwood Dr, Milton, MA 02186Off Market
- $2,112,6004 bd4 ba4.2k sqft40 Parkwood Dr, Milton, MA 02186Off Market
- $1,914,6004 bd1 ba4.9k sqft270 Hillside St, Milton, MA 02186Off Market
- $1,913,0005 bd3 ba3.1k sqft237 Hillside St, Milton, MA 02186Off Market
Nearby schools
GreatSchools rating
- 9/10Cunningham SchoolGrades: PK-5Distance: 2.3 mi
- 8/10Charles S Pierce Middle SchoolGrades: 6-8Distance: 2.3 mi
- 10/10Milton High SchoolGrades: 9-12Distance: 1.9 mi
Schools provided by the listing agent
- Elementary: Cunningham
- Middle: Charles Pierce
- High: Milton High School
Source: MLS PIN. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$2,232,600
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$2,232,600
- Massachusetts
- Norfolk County
- Milton
- 02186
- 23 Parkwood Dr
Nearby cities
Nearby zip codes
Other Milton Topics
