27 Pinecliff Dr, Marblehead, MA 01945
OFF MARKET

27 Pinecliff Dr
Marblehead, MA 01945

  • 5 Beds
  • 3.5 Baths
  • 3,984 sqft (on 0.65 acres)

$2,823,200

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $16,273/mo*

$2,823,200

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $16,273/mo*
5 Beds
3.5 Baths
3,984 sqft
(on 0.65 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Direct and private HARBOR FRONT views abound in this one of a kind home in the Cliffs neighborhood. Smell the ocean and listen to the sea gulls while enjoying a glass of wine, pool side and gazing out over the harbor. Cozy up near one of the many picture windows to enjoy the views inside and the warmth of one of the 3 fire places that are laid with the original bricks from the Beacon Hill sidewalks. The first floor master wing provides stunning views, full master bath, office and first floor laundry. An upgraded and open concept kitchen provides the perfect spot for entertaining with beamed ceiling, breakfast nook and views into the dining room overlooking the water. Upstairs boasts an additional 4 bedrooms and 2 full baths while the lower level offers an additional 1500 square feet of partially finished pool level living space. House can be purchased with an additional half acre of buildable harbor front land MLS #72449646.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 27 Pinecliff Dr

Interior Features

Interior Details
BasementNumber of Rooms: 10
Heating & Cooling
Heating: Baseboard, Radiant, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1974
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.65 acres

Price History for 27 Pinecliff Dr

DatePriceEventSource
02/27/2019$965,000Sold
N/A
02/27/2019$2,190,000PriceChange
Agent Provided
02/11/2019$1,195,000PendingAgent Provided
02/05/2019$1,195,000PriceChange
Agent Provided
01/09/2019$2,190,000PriceChange
Agent Provided
10/15/2018$1,650,000PendingAgent Provided
09/25/2018$2,190,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$20,243
Assessment$2,236,800
Home facts updated by county records

Comparable Sales for 27 Pinecliff Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.06
Single-Family Home
$3,750,000
06/11/25
5
3.5
3,576
0.17
Single-Family Home
$1,400,000
06/30/25
4
3
3,598
0.01
Single-Family Home
$4,250,000
10/20/25
5
4.5
5,725
0.44
Single-Family Home
$1,500,000
09/22/25
4
3
3,174
0.41
Single-Family Home
$1,450,000
12/01/25
4
2.5
5,109
0.27
Single-Family Home
$1,275,000
10/08/25
3
2.5
2,547
0.39
Single-Family Home
$1,175,000
05/27/25
4
2.5
2,040
0.46
Single-Family Home
$2,175,000
08/27/25
5
3.5
4,067
0.51
Single-Family Home
$815,000
01/30/26
4
3
2,484
0.47
Single-Family Home
$800,000
08/19/25
4
2.5
2,447

Assigned Schools

These are the assigned schools for 27 Pinecliff Dr.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Marblehead

At least 107 Trulia users voted on each feature.
  • 96 % Say it's dog friendly

  • 91 % Say people would walk alone at night

  • 80 % Say yards are well-kept

  • 78 % Say kids play outside

  • 78 % Say parking is easy

  • 78 % Say car is needed

  • 77 % Say there's holiday spirit

  • 72 % Say there are sidewalks

  • 70 % Say it's walkable to restaurants

  • 70 % Say neighbors are friendly

  • 69 % Say they plan to stay for at least 5 years

  • 66 % Say it's quiet

  • 64 % Say it's walkable to grocery stores

  • 64 % Say there's wildlife

  • 64 % Say streets are well-lit

  • 46 % Say there are community events

Learn more about our methodology.
  • Trulia User
    "There are lots of community events and one of the best July 4th celebrations. Lots of church groups, Council on aging, etc"
  • 9vpwcs25jb
    "Everyone is friendly towards dogs. The dogs love every person who comes close to them. It’s a pleasure to see. "
  • 9vpwcs25jb
    "I work from home so I don’t commute. I have the best of both worlds and I’m totally appreciative. Out of the worst pandemic comes the best commute ever! How lucky we are!! "
  • Lytania Jason Knowles
    "I work ten minutes away so it’s great. 7:45-8:15 in town is a mess because all the schools are doing drop off. "
  • MARC MELTZER
    "Aside from the morning & afternoon traffic the commute is okay but to & from work can be very stressful "
  • Bdmn63
    "This is an absolutely fantastic community with parents who are actively involved with their families in the community great schools and great lifestyle with the beaches in waterfronts"
  • Tpnohelty
    "Great area to walk with dogs. Safe neighborhood and everyone keeps their dogs leashed when out and about."
  • Cassandra
    "Christmas walk every year Santa comes in a lobster boat and they have a parade and all the local stores have specials "
  • Cassandra
    "Art festival in the summer. Sidewalk sales for all the local shops. Crocker park has fireworks on holidays and beautiful view of the ocean. Outdoor dining on the water "
  • R E. M.
    "this is a one of a kind community. it is very historic, going back to the 1600's. it is very safe and family friendly. it is a bit hard to commute to, but totally worth it."
  • Chalvinleo
    "Marblehead is truly something else. I have lived here for the past 10 years and I am sad to leave. This town will always feel like home. "
  • Msherman48
    "It’s Marblehead, an almost 400 year old fishing village on Massachusetts Bay. We have a small town but urban “walking” downtown on a spectacularly beautiful natural harbor. This is the real thing! And, it’s only a short hop to Boston, America’s intellectual capital city. If it didn’t have a cold winter, the whole world would want to live here!"
  • Cynshor
    "Takes a little while to get out of Marblehead and through surrounding Salem and Swampscott. Worth every minute on the ride home when you hit the water views."
  • dbrownbos
    "My neighborhood is in a great location close to schools and old town section of town. You can walk to shopping and the harbor. Lots of attractions nearby. "
  • Frank K.
    "I’ve lived in this neighborhood for fourteen years and have nice neighbors. It is safe and people watch out for each other."
  • Rhonda
    "Stunning ocean and harbor views. Beach and water sports. Walking running and biking on the Neck. Eastern and Corinthian yacht clubs among others. "
  • richard n. a.
    "Fabulous and unique seaside community. History is everywhere. 16 miles from Boston. No place to build so housing is always in demand and home values do not get hit hard in economic downturns. Great town to protect your real estate investment. "
  • Sean
    "A corner lot in the desirable family neighborhood. Kids all abound. Ice Cream Trucks and good people."
  • Alicia H.
    "I live here and this town is fantastic - it's beautiful and friendly and full of things to do! "
  • Arian S.
    "Excellent location, wonderful views, quite. I love to live and work here."

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27 Pinecliff Dr, Marblehead, MA 01945 is a 5 bedroom, 4 bathroom, 3,984 sqft single-family home built in 1974. This property is not currently available for sale. 27 Pinecliff Dr was last sold on Feb 27, 2019 for $965,000. The current Trulia Estimate for 27 Pinecliff Dr is $2,823,200.