66 Pershing Ln, Orleans, MA 02653
Property image
Property image
OFF MARKET

$4,151,500

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

66 Pershing Ln, Orleans, MA 02653

Est. Refi. Payment $23,374/mo*
Refinance Your Home
Currently Off Market - Sold Apr 27, 2020 for $3,150,000

Home Value

Trulia Estimate
$4.15M
Since last month
Decreased$12K (-0.3%)
Since last year
Increased$146K (+3.6%)
Since last sale
Increased$1M (+31.8%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +70% in the last 10 years
MonthEstimated value
2026
August 2026$4.15M
August 2026$4.15M
July 2026$4.16M
June 2026$4.18M
May 2026$4.1M
April 2026$4.06M
March 2026$4.02M
February 2026$3.95M
January 2026$3.98M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
142 Monument Road, Orleans, MA
0.78
Single-Family Home
$1,780,000
03/17/26
4
3.5
2,565
63 Old Field Road, Orleans, MA
0.52
Single-Family Home
$5,450,000
01/23/26
4
3
2,413
9 Joy Lane, Orleans, MA
0.89
Single-Family Home
$2,800,000
10/16/25
3
5.5
4,250
136 Monument Road, Orleans, MA
0.76
Single-Family Home
$2,300,000
10/14/25
4
3
2,796
10 Lake Farm Lane, Orleans, MA
1.10
Single-Family Home
$2,000,000
10/29/25
3
2.5
2,709
22 Pilgrim Lake Terrace, Orleans, MA
0.97
Single-Family Home
$1,100,000
03/05/26
3
2.5
2,379
80 Briar Spring Road, Orleans, MA
1.04
Single-Family Home
$1,481,000
04/22/26
3
3.5
2,226
16 Carlton Road, Orleans, MA
1.27
Single-Family Home
$1,975,000
07/09/26
3
3.5
2,892
9 Packet Landing, Orleans, MA
1.04
Single-Family Home
$1,549,000
08/17/26
4
2.5
3,036
75 Monument Road, Orleans, MA
0.82
Single-Family Home
$1,050,000
05/28/26
3
2
1,829

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
64 Pershing Lane, Orleans, MA 02653
0.02
$6,250,000
5
6.5
5,800
For Sale
5 Kidd Way, Orleans, MA 02653
0.11
$4,200,000
5
4.5
3,130
For Sale
63 kescayogansett Road, Orleans, MA 02653
0.12
$4,799,999
5
7
5,400
For Sale
9 Higgins Way, Orleans, MA 02653
0.24
-
2
2
1,242
Off Market
40 Pershing Lane, Orleans, MA 02653
0.21
$2,996,200
3
2.5
2,560
Off Market
35 Pershing Lane, Orleans, MA 02653
0.24
$1,924,100
3
2.5
3,164
Off Market
34 Jack Knife Point Road, Orleans, MA 02653
0.29
$5,832,900
4
4.5
3,443
Off Market
17 Cove Road #1, 2, 3 & 4, Orleans, MA 02653
0.28
$898,600
4
4
2,200
Off Market
5 Reilly Run, Orleans, MA 02653
0.28
$930,000
3
3.5
2,102
Recently Sold
7 Reilly Run, Orleans, MA 02653
0.28
$956,000
3
3.5
2,102
Recently Sold
3 Reilly Run, Orleans, MA 02653
0.28
$940,000
3
3.5
2,102
Recently Sold
2 Reilly Run, Orleans, MA 02653
0.28
$972,500
3
3.5
2,102
Recently Sold

Local Information

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

Home Highlights

Property Type
Single-Family Home
Year Built
2004
Lot Size
1.39 acres
Living Area
3,862 sqft
Price/Sqft
$1,075
Parking
Garage

About this House

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.
66 Pershing Ln, Orleans, MA 02653 is a 3 bedroom, 5 bathroom, 3,862 sqft single-family home built in 2004. It last sold for $3,150,000 on Apr 27, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,151,500, with a rent estimate of $4,507/month.

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 and Tax history

DateEventPrice
Apr 27, 2020
Source: CCIMLS #21905772
Sold
$3,150,000
Apr 27, 2020
Source: Agent Provided
PendingToActive
$3,499,000
Mar 16, 2020
Source: Agent Provided
Pending
$3,499,000
Sep 3, 2019
Source: Agent Provided
PriceChange
$3,499,000
Price decreased by 9%
Aug 9, 2019
Source: Agent Provided
Listed For Sale
$3,849,000

Market trends in Orleans

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
44
1MoM

Around this home

View nearby schools on GreatSchools
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"
    7
    Flag
  • 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. "
    0
    Flag
  • Maria L.
    "Very dog-friendly! And what dogs don't love the Cape? Water, beaches, squirrels & bunnies to chase...It's dog heaven!"
    0
    Flag
  • 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"
    3
    Flag
  • 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."
    4
    Flag
  • 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."
    4
    Flag
  • 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?"
    3
    Flag
  • 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..."
    0
    Flag
  • Judy B.
    "Police Block party, concerts, shopping,ice skating rink, Nauset Beach, Baseball games, Christmas Stroll, Halloween walk"
    1
    Flag
  • 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!! "
    4
    Flag
  • 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. "
    2
    Flag
  • 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. "
    0
    Flag
  • 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. "
    0
    Flag
  • Brianhopkins a.
    "short walk to for coffee/grocery/dinning bike to bay or on trail"
    2
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 66 Pershing Ln

  • What is 66 Pershing Ln estimated to be worth?
    Trulia's estimated value for 66 Pershing Ln in Orleans, MA is $4,151,500.
  • What is the price history for 66 Pershing Ln?
    66 Pershing Ln in Orleans, MA last sold for $3,150,000 in April 2020.
  • Is Orleans a buyer's or seller's market?
    Orleans is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Orleans?
    Residents describe Orleans, MA as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Orleans, MA.
  • Does 66 Pershing Ln have air conditioning?
    Yes, 66 Pershing Ln in Orleans, MA has air conditioning.
  • How big is the lot at 66 Pershing Ln?
    The lot at 66 Pershing Ln in Orleans, MA is about 1.4 acres.

Explore by feature - Air Conditioning

Explore by feature - Washer/dryer

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 66 Pershing Ln

Skip to last item
Skip to first item

Homes for sale near 66 Pershing Ln

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item