66 Pershing Ln, Orleans, MA 02653
OFF MARKET

66 Pershing Ln
Orleans, MA 02653

  • 3 Beds
  • 4 Baths
  • 3,862 sqft (on 1.39 acres)

$4,174,500

Trulia Estimate
as of Jun 23, 2026
Est. Refi. Payment $23,108/mo*

$4,174,500

Trulia Estimate
as of Jun 23, 2026
Est. Refi. Payment $23,108/mo*
3 Beds
4 Baths
3,862 sqft
(on 1.39 acres)

Local Information

  • Map ViewExplore the area around 66 Pershing Ln.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

The One You've Been Waiting For! Private, permanent and licensed deep water dock, vibrant water views, guest house, classic coastal elegance and superb condition define 66 Pershing Lane. Privately set near the apex of Mayflower Point, a semi-rural promontory extending into the Pleasant Bay estuary, this thoughtfully designed home occupies an enviable position in the Cape Cod boating mecca that is Pleasant Bay. A handsome main house sits atop a bluff above the flood zone, with views out to Nauset Beach and the Atlantic. More recently built, an equally handsome, detached structure includes a full guest studio with water views, deck, and 2-car garage below. The main house--with high ceilings, rich molding, gleaming wood floors, and classic appointments--echoes the understated elegance of historic sea captains' manses. The first level's open floor plan affords enchanting water views from living/dining/kitchen areas and easy access to outdoors for dining, relaxation and play.
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
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 66 Pershing Ln

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Hardwood
Interior Details
Number of Rooms: 8Types of Rooms: Walk In Closet, Dining Room, Mud Room, Office, Pantry
Appliances & Utilities
DishwasherRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodPatio
Parking & Garage
GarageParking Spaces: 8Parking: Garage Detached

Property Information

Year Built
Year Built: 2004Year Updated: 2004
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.39 acres

Price History for 66 Pershing Ln

DatePriceEventSource
04/27/2020$3,150,000Sold
CCIMLS #21905772
04/27/2020$3,499,000PendingToActiveAgent Provided
03/16/2020$3,499,000PendingAgent Provided
09/03/2019$3,499,000PriceChange
Agent Provided
08/09/2019$3,849,000Listed For SaleAgent Provided
06/17/2002$1,500,000Sold
N/A

Market trends in Orleans

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
45
1
MoM
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Property Tax and Assessment

Year2025
Tax$25,523
Assessment$4,090,200
Home facts updated by county records

Comparable Sales for 66 Pershing Ln

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.24
Single-Family Home
$1,575,000
07/02/25
3
2.5
3,164
0.39
Single-Family Home
$2,360,000
06/27/25
4
3.5
2,988
0.78
Single-Family Home
$1,780,000
03/17/26
4
3.5
2,565
0.52
Single-Family Home
$5,450,000
01/23/26
4
3
2,413
0.89
Single-Family Home
$2,800,000
10/16/25
3
5.5
4,250
0.76
Single-Family Home
$2,300,000
10/14/25
4
3
2,615
1.10
Single-Family Home
$2,000,000
10/29/25
3
2.5
2,709
0.97
Single-Family Home
$1,100,000
03/05/26
3
2.5
2,379
1.03
Single-Family Home
$1,481,000
04/22/26
3
3.5
2,226
0.80
Single-Family Home
$1,050,000
05/28/26
3
2
1,829

Nearby homes

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Assigned Schools

These are the assigned schools for 66 Pershing Ln.
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 Orleans

At least 30 Trulia users voted on each feature.
  • 94 % Say parking is easy

  • 93 % Say yards are well-kept

  • 88 % Say there's wildlife

  • 86 % Say it's dog friendly

  • 85 % Say people would walk alone at night

  • 84 % Say it's quiet

  • 83 % Say car is needed

  • 70 % Say there's holiday spirit

  • 67 % Say they plan to stay for at least 5 years

  • 65 % Say neighbors are friendly

  • 53 % Say there are community events

  • 43 % Say it's walkable to restaurants

  • 37 % Say kids play outside

  • 32 % Say streets are well-lit

  • 27 % Say it's walkable to grocery stores

  • 22 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Deanna Johnson
    "None People are very unfriendly and selfish. Very little kindness shown in this town. Speaking is not enforced in Orleans. Many people have been hit on bicycles including myself. This town is more business oriented than people oriented. Overall very unfriendly compared to nearby towns"
  • Gladda07
    "Not too bad, there are good traffic days and there are not so good days.It all depends on the season.Fall/Winter its not bad. Spring /Summer time its a nightmare. Lots of out of towners come visit so it is a bit congested. "
  • Maria L.
    "Very dog-friendly! And what dogs don't love the Cape? Water, beaches, squirrels & bunnies to chase...It's dog heaven!"
  • Jessicalennox
    "A lot of residents are not here year round. People are genuine and friendly but in the off season there aren’t as many"
  • Ib4alljm
    "You must have access to personal transportation if you want to go farther than a mile or two in your day to day life. However this is a lovely area if you want to walk to the post office or to Friends Marketplace, or just across the street to the bank or Corner Store Burrito bar."
  • Robert C.
    "We have a very active Nauset Heights Association, with both an annual meeting and a business meeting, a summer sand sculpture event, a tennis tournament and a golf tournament. There is also our annual lawn party, at which most of the 200 members Appear. Finally, we do a community cleanup both once in the spring and once in the fall."
  • Robert C.
    "We have owned here 27 years, and lived here full-time for the past 10 years. The neighborhood is unique because it is low density, has homes of character, is quiet and for most of us is a five minute walk to the Atlantic Ocean. And most of us see it from our windows, and hear it almost always. Is that good or what?"
  • Ryan
    "There are a lot of elderly and also expensive summer homes, so you have a TON of tax revenue going to the schools, but not too many students..."
  • Judy B.
    "Police Block party, concerts, shopping,ice skating rink, Nauset Beach, Baseball games, Christmas Stroll, Halloween walk"
  • nauset
    "This is beach town with a ton of elderly so you have a HUGE tax base with a lot of money going to schools with very few kids. The schools are terrific as a result. Plus, kids can play outside, and out “back yard” is Cape Cod National Seashore. Not bad. Don’t tell anyone!! "
  • nauset
    "Neighborhood with year round residents in a beach town with a lot of seasonal people. Plus, we’re basically in a National Park. There are little stores and food available in East Orleans. ~3 miles to Nauset Beach. Year round on Cape Cod has turned out better than we could have hoped for. "
  • Shelly E.
    "It has both ocean cost line and bay coastline. The schools are amazing. Access to the off road beach area for residence only. "
  • Madison S.
    "You should put things like 'ocean views', beach access, deeded rights, when figuring values. Stated values never seem to reflect such precious commodities, which are such a plus in these areas, in fact, one of the whole reasons people live here. "
  • Brianhopkins a.
    "short walk to for coffee/grocery/dinning bike to bay or on trail"

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Homes for sale near 66 Pershing Ln

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Off Market Homes Near 66 Pershing Ln

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66 Pershing Ln, Orleans, MA 02653 is a 3 bedroom, 5 bathroom, 3,862 sqft single-family home built in 2004. This property is not currently available for sale. 66 Pershing Ln was last sold on Apr 27, 2020 for $3,150,000. The current Trulia Estimate for 66 Pershing Ln is $4,174,500.