Charming, affordable, and filled with opportunity, 98 Pleasant Street presents a rare chance to own in the highly sought-after Cunningham Park neighborhood of Milton. Perfectly situated on a spacious corner lot, this charming home is filled with timeless character, offering the ideal canvas to bring your vision to life. The location is unmatched — just minutes to I-93, steps from the trails and fields of Cunningham Park, and close to all the shops, restaurants, and conveniences of Milton. Combined with top-rated schools and an unbeatable neighborhood setting, this home offers incredible value in a premier location. Whether you choose to restore, renovate, or reimagine, the potential here is undeniable. Selling in “AS IS” CONDITION.
Pending
Price cut: $50K (5/28)
$725,000
98 Pleasant St, Milton, MA 02186
3beds
1,046sqft
Single Family Residence
Built in 1896
6,809 Square Feet Lot
$731,500 Zestimate®
$693/sqft
$-- HOA
What's special
Filled with timeless characterSpacious corner lot
- 43 days |
- 179 |
- 4 |
Zillow last checked:
Listing updated:
Listed by:
Tammy Connearney 508-574-6510,
Lands End Realty, Inc. 508-812-0210
Source: MLS PIN,MLS#: 73519431
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 1
- Full bathrooms: 1
Heating
- Baseboard, Natural Gas
Cooling
- Window Unit(s)
Features
- Flooring: Wood
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 1,046
- Total interior livable area: 1,046 sqft
- Finished area above ground: 1,046
Property
Parking
- Total spaces: 3
- Parking features: Detached, Paved Drive, Off Street
- Garage spaces: 1
- Uncovered spaces: 2
Features
- Patio & porch: Porch - Enclosed, Patio
- Exterior features: Porch - Enclosed, Patio
Lot
- Size: 6,809 Square Feet
- Features: Corner Lot
Details
- Parcel number: 131870
- Zoning: RC
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Other (See Remarks)
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Stone, Brick/Mortar
- Roof: Shingle
Condition
- Year built: 1896
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Highway Access, House of Worship, Private School, Public School
HOA
- Has HOA: No
Location
- Region: Milton
Financial & listing details
- Price per square foot: $693/sqft
- Tax assessed value: $777,600
- Annual tax amount: $9,263
- Date on market: 5/18/2026
Estimated market value
$731,500
$695,000 - $768,000
$3,338/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/12/2026 | Pending sale | $725,000$693/sqft |
Source: MLS PIN #73519431 Report a problem | ||
| 6/1/2026 | Contingent | $725,000$693/sqft |
Source: MLS PIN #73519431 Report a problem | ||
| 5/28/2026 | Price change | $725,000-6.5%$693/sqft |
Source: MLS PIN #73519431 Report a problem | ||
| 5/19/2026 | Price change | $775,000-6.1%$741/sqft |
Source: MLS PIN #73519431 Report a problem | ||
| 5/14/2026 | Listed for sale | $824,999+187.5%$789/sqft |
Source: MLS PIN #73519431 Report a problem | ||
| 8/22/2008 | Sold | $287,000+64%$274/sqft |
Source: Public Record Report a problem | ||
| 4/28/2008 | Sold | $175,000-56.6%$167/sqft |
Source: Public Record Report a problem | ||
| 8/20/2004 | Sold | $403,000+30%$385/sqft |
Source: Public Record Report a problem | ||
| 3/1/2002 | Sold | $310,000+85.6%$296/sqft |
Source: Public Record Report a problem | ||
| 11/21/1989 | Sold | $167,000$160/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $8,350 +1.5% | $752,900 0% |
| 2024 | $8,223 +4.1% | $753,000 +8.6% |
| 2023 | $7,902 +1.6% | $693,200 +11.2% |
| 2022 | $7,774 +4.8% | $623,400 +10.3% |
| 2021 | $7,421 +3.5% | $565,200 +3.4% |
| 2020 | $7,169 +2.5% | $546,400 +3% |
| 2019 | $6,992 +14.3% | $530,500 +19.8% |
| 2018 | $6,115 +6.8% | $442,800 +4.8% |
| 2017 | $5,728 -7.5% | $422,400 -7.9% |
| 2016 | $6,191 +9.7% | $458,600 +13.3% |
| 2015 | $5,643 +3.1% | $404,800 +10.8% |
| 2014 | $5,474 +2% | $365,200 |
| 2013 | $5,368 +2.4% | $365,200 |
| 2012 | $5,241 +2.9% | $365,200 +0.9% |
| 2011 | $5,092 +4.6% | $361,900 -0.7% |
| 2010 | $4,867 +10% | $364,600 -3.2% |
| 2009 | $4,424 +3.2% | $376,800 -3.8% |
| 2008 | $4,288 -0.3% | $391,600 -1.4% |
| 2007 | $4,303 +6.8% | $397,000 |
| 2006 | $4,030 +14.4% | $397,000 +18.8% |
| 2005 | $3,524 -0.1% | $334,300 +14.8% |
| 2004 | $3,528 +3.3% | $291,100 |
| 2003 | $3,415 +12.2% | $291,100 +61.3% |
| 2002 | $3,045 +21.8% | $180,500 +32.1% |
| 1999 | $2,501 | $136,600 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 02186
Nearby schools
GreatSchools rating
- 9/10Cunningham SchoolGrades: PK-5Distance: 0.8 mi
- 7/10Charles S Pierce Middle SchoolGrades: 6-8Distance: 1.1 mi
- 10/10Milton High SchoolGrades: 9-12Distance: 1 mi
Schools provided by the listing agent
- Elementary: Cunningham School
- Middle: Charles S Pierce Middle School
- 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.
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Massachusetts
- Norfolk County
- Milton
- 02186
- 98 Pleasant St




