255 High Toss Road, Wellfleet, MA 02667
Property image
Property image
OFF MARKET

$1,646,600

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 3,240 sqft (on 1.39 acres)

255 High Toss Road, Wellfleet, MA 02667

Est. Refi. Payment $9,264/mo*
Refinance Your Home
Currently Off Market - Sold Aug 20, 2024 for $1,350,000

Home Value

Trulia Estimate
$1.65M
Since last month
Decreased$13K (-0.8%)
Since last year
Increased$257K (+18.4%)
Since last sale
Increased$301K (+22.3%)
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 +78% in the last 10 years
MonthEstimated value
2026
August 2026$1.65M
August 2026$1.64M
July 2026$1.66M
June 2026$1.67M
May 2026$1.65M
April 2026$1.57M
March 2026$1.48M
February 2026$1.42M
January 2026$1.4M
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
30 Chequessett Knolls Drive, Wellfleet, MA
0.49
Single-Family Home
$1,425,000
07/08/26
2
3
2,641
130 Daniels Drive, Wellfleet, MA
0.67
Single-Family Home
$1,620,000
09/10/25
3
3.5
3,376
320 Coles Neck Road, Wellfleet, MA
0.65
Single-Family Home
$600,000
06/05/26
3
2
1,552
105 West Main Street, Wellfleet, MA
0.80
Single-Family Home
$910,000
11/12/25
5
3
2,425
225 Coles Neck Road, Wellfleet, MA
0.80
Single-Family Home
$1,500,000
01/22/26
3
3
1,790
20 Thomas Coles Lane, Wellfleet, MA
0.73
Single-Family Home
$789,000
10/23/25
4
2
1,902
3034 Baker Avenue, Wellfleet, MA
0.81
Single-Family Home
$945,000
07/09/26
3
2
1,648
46 Hiram Hill Road, Wellfleet, MA
0.67
Single-Family Home
$745,400
10/24/25
4
1.5
1,792
495 Chequessett Neck Road, Wellfleet, MA
0.86
Single-Family Home
$2,500,000
09/25/25
6
1.5
1,906
615 Chequessett Neck Road, Wellfleet, MA
0.87
Single-Family Home
$5,200,000
08/05/26
5
4.5
4,454

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
145 Highmeadow Rd, Wellfleet, MA 02667
0.08
$700,000
-
-
-
For Sale
105 Highmeadow Road, Wellfleet, MA 02667
0.16
$1,412,900
3
2.5
2,023
Off Market
35 High Meadow Road, Wellfleet, MA 02667
0.23
$1,435,700
3
2
3,333
Off Market
95 Newcomb Hill Road, Wellfleet, MA 02667
0.27
$798,700
3
1
842
Off Market
10 Bellamy Lane, Wellfleet, MA 02667
0.32
$1,051,900
3
2
1,232
Off Market
50 Newcomb Hill Way, Wellfleet, MA 02667
0.36
$1,696,800
5
4
2,845
Off Market
460 Old Chequessett Neck, Wellfleet, MA 02667
0.43
-
-
-
-
Off Market
100 Old High Toss Bridge Road, Wellfleet, MA 02667
0.40
$1,348,000
3
2
1,792
Off Market
506 Old Chequessett Neck, Wellfleet, MA 02667
0.47
$1,319,500
5
3
3,000
Off Market
50 Hopkins Drive, Wellfleet, MA 02667
0.45
$1,399,000
3
3.5
3,041
Off Market
30 Chequessett Knolls Drive, Wellfleet, MA 02667
0.49
$1,425,000
2
3
2,641
Recently Sold

Local Information

  • Map ViewExplore the area around 255 High Toss Road.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1999
1.39 acre lot
3,240 sqft
$508/sqft
Garage

About this House

Sited on a hilltop overlooking the National Seashore, is this architect-designed, custom-built contemporary shingle-style home with unparalleled privacy. The property offers a quiet close to nature retreat that defines the draw to the Outer Cape. Spacious and light-filled, the home's design is based on a generous first-floor layout. Enter through a handsome front entrance that opens into a foyer and further into a light-filled great room with a fireplace, dining area, and kitchen. On this same level, on one side of the home, is a primary bedroom with an en-suite bathroom and a cozy den/office with a fireplace, the seller's favorite room for settling in for the evening. A half bath with laundry and an attached two garage is on the other side of the house. The custom-crafted staircase winds up to the second floor, opening into a spacious family room with a bedroom on either side and a shared bathroom. It is the perfect arrangement for family and guests. Across the back of the home is an expansive deck for outdoor leisure activities or entertaining. The premier bayside location allows easy backroad access to town center, marina, golf, tennis, bay, pond, and ocean beaches. Property is shown by private appointment.
255 High Toss Road, Wellfleet, MA 02667 is a 3 bedroom, 3 bathroom, 3,240 sqft single-family home built in 1999. It last sold for $1,350,000 on Aug 20, 2024 (7% below the $1,450,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,646,600, with a rent estimate of $3,670/month.
Last check for updates: about 17 hours ago
Listed by Ashley Fawkes, (508) 237-1986
Kinlin Grover Compass
Bought with: Buyer Unrepresented, cci.UnrepBuyer
Source: CCIMLS, MLS#22401766

Home Details for 255 High Toss Road

Interior Features

Interior Details
Number of Rooms: 8
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Appliances & Utilities
Appliances: Oil, Tankless Water Heater
Heating & Cooling
Heating: OilHas CoolingHas HeatingHeating Fuel: Oil
Fireplace & Spa
Number of Fireplaces: 2
Windows, Doors, Floors & Walls
Flooring: Wood, Tile, Carpet
Levels, Entrance, & Accessibility
Stories: 2Floors: Wood, Tile, Carpet

Exterior Features

Exterior Home Features
Roof: Asphalt ShinglePatio / Porch: Deck
Parking & Garage
Number of Garage Spaces: 2Has a GarageParking Spaces: 2Parking: Garage
Frontage
Not on Waterfront

Days on Market

Cumulative Days on Market: 70

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Shingle Siding
Property Information
Parcel Number: 122340

Price & Status

Price
List Price: $1,450,000

Active Status

MLS Status: Closed

Location

Direction & Address
City: Wellfleet

Building

Building Area
Building Area: 3240 Square Feet

Lot Information

Lot Area: 1.39 Acres

Listing Info

Special Conditions: None

Miscellaneous

Mls Number: 22401766Attribution Contact: ashley.fawkes@compass.comShowing Requirements: Call Listing Agent, Pet (See Remarks), Yard Sign

Price and Tax history

DateEventPrice
Aug 20, 2024
Source: CCIMLS #22401766
Sold
$1,350,000
Jul 5, 2024
Source: CCIMLS #22401766
Pending
$1,450,000
Jun 26, 2024
Source: CCIMLS #22401766
PriceChange
$1,450,000
Price decreased by 3%
Jun 4, 2024
Source: CCIMLS #22401766
PriceChange
$1,495,000
Price decreased by 6%
Apr 26, 2024
Source: CCIMLS #22401766
Listed For Sale
$1,595,000

Market trends in Wellfleet

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
50
8MoM

Around this home

What Locals Say about Wellfleet

At least 9 Trulia users voted on each feature.

  • 93 % Say car is needed

  • 83 % Say there's wildlife

  • 80 % Say it's quiet

  • 79 % Say yards are well-kept

  • 78 % Say parking is easy

  • 75 % Say there's holiday spirit

  • 69 % Say people would walk alone at night

  • 67 % Say it's dog friendly

  • 62 % Say they plan to stay for at least 5 years

  • 60 % Say it's walkable to restaurants

  • 56 % Say neighbors are friendly

  • 46 % Say there are community events

  • 32 % Say kids play outside

  • 29 % Say it's walkable to grocery stores

  • 29 % Say there are sidewalks

  • 13 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Whytm2279x
    "Not vey local but very northeastern, which is great!. Lots of great places for shopping and having great food. The shops offer great variety with great taste "
    0
    Flag
  • Reuben Walton
    "Wellesley is an amazing town because it’s got so much culture and it has a beautiful coastline and it’s just about to get in the dump away from PTown so what more could you want to?"
    0
    Flag
  • Nancy
    "Unique community where people care and look out for each other. Incredible beauty that everyone works hard to preserve."
    0
    Flag
  • Matt
    "very safe area, great school system. The type of neighborhood where you can leave your doors unlocked and neighbors look out for each other. "
    1
    Flag
  • Arnold_t_pants
    "This is just my vacation location. But it’s my favorite place. In the summer, there are regular community events for people of all ages. In the off-season, it’s just a lovely location without us visitors!"
    2
    Flag

LGBTQ Local Legal Protections

All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than CC&I Assoc. of REALTORS®, Inc. includes the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS®, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. This site was last updated 2026-09-05 15:08:06 PDT. All properties are subject to prior sale, changes, or withdrawal. Copyright 2026© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

Frequently asked questions about 255 High Toss Road

  • What is 255 High Toss Road estimated to be worth?
    Trulia's estimated value for 255 High Toss Road in Wellfleet, MA is $1,646,600.
  • What is the price history for 255 High Toss Road?
    255 High Toss Road in Wellfleet, MA last sold for $1,350,000 in August 2024.
  • Is Wellfleet a buyer's or seller's market?
    Wellfleet is currently a balanced market, based on recent for-sale activity.
  • What do residents say about Wellfleet?
    Residents describe Wellfleet, MA as quiet, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Wellfleet, MA.
  • Does 255 High Toss Road have air conditioning?
    Yes, 255 High Toss Road in Wellfleet, MA has air conditioning.
  • Does 255 High Toss Road have a yard?
    Yes, 255 High Toss Road in Wellfleet, MA has a yard.

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