About this home
October Hill, the original estate on Paine Avenue in historic Prides Crossing reflects the quiet grace and coastal character that define Boston’s Gold Coast. This magnificent 2.6 acre private property features original Olmsted-designed gardens, southern exposure, and breathtaking views of Baker’s and Misery Islands and Salem Sound, plus private beach access and a current mooring off the beach. Cherished and meticulously maintained by the same owners for more than 35 years, the home has benefited from several significant updates in the past 2 years including new windows, upgraded electrical systems, updated Primary suite and bath with custom walk-in closet, refinished floors, and fresh exterior and interior paint. Inside, timeless craftsmanship shines through original custom woodwork, hardwood floors, soaring ceilings, fireplaces, and an expansive eat-in kitchen. Ideal setting for both everyday living and elegant entertaining. A home gym, outdoor shower, hot tub and game room bring a touch of resort-style ease to daily life.
Listing last checked: Listing updated:
Listed by Gretchen Berg · J. Barrett & Company · MLS #73586522
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Details at a glance
Interior6 property facts
- Rooms
- 14
- Heating
- Hot Water, Oil, Propane, Fireplace(s), Fireplace
- Cooling
- None
- Flooring
- Wood, Tile, Carpet, Flooring - Wood, Flooring - Hardwood
- Basement
- Yes · Full, Partially Finished, Walk-Out Access, Interior Entry
- Fireplaces
- 7
Building6 property facts
- Style
- Single Family Residence
- Year built
- 1895
- Garage
- 2
- Parking
- 11
- Foundation
- Stone
- Roof
- Shingle
Land & utilities5 property facts
- Lot size
- 2.59 acres
- Water
- Public
- Sewer
- Private Sewer
- Pool
- Not reported
- Zoning
- R90
Financial3 property facts
- Annual taxes
- $34,604
- Assessment year
- 2026
- HOA fee
- $800 (billing period not supplied)
Location
Estimated monthly cost
Explore costs at the $5,300,000 asking price. Adjust the assumptions to your situation.
Known monthly costs$29,683 / monthAdjust
- Principal & interest
- $26,800
- Property tax
- $2,884
- Insurance
- Not entered
- HOA
- Not entered
Listing annual taxes: $34,604. Initial monthly tax is one twelfth of that amount. Listing HOA fee: $800. The billing period was not supplied; confirm the monthly amount before adding it.
Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.
The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.
More property insights
Automated value estimate $5,641,759
Estimated range $3,690,931–$7,592,587.
Automated estimates are not appraisals or guarantees of market value.
Request a professional market analysisPhoto-based condition insights
Overall presentation: above average
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About 23 Paine Avenue
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