Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$4,250,000 Coming Soon

  • For Sale
  • Coming Soon / No Show
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,244 Sq. Ft.
  • 2.26 Acres
  • 2 Car Garage
  • Updated 3 days ago
See This Home
Save This Home
See This Home
Save This Home
Set on more than 2.5 acres with over 300 feet of private waterfront with western views, 156 High Winds Drive captures westerly views across Broad Cove toward Casco Bay. Located within the prestigious High Winds neighborhood, with walking trails and shared access to a dock and float, this exceptional setting offers the quintessential coastal Maine lifestyle-boating, fishing, swimming, and spectacular sunsets. Custom built in 2019, the residence was thoughtfully designed to embrace its waterfront setting, with water views from nearly every room. Handcrafted millwork and 5-inch quarter-sawn oak floors showcase the quality throughout. The beautifully appointed kitchen features Thermador appliances, a generous island, and walk-in pantry, opening to a spacious family room with gas fireplace and a light-filled dining area overlooking the lawn and waterfront. Four ensuite bedrooms offer exceptional flexibility. A first-floor suite with fireplace can serve as a primary bedroom, private guest quarters, or home office. Upstairs, three additional suites include a second primary option. Both primary suites feature fireplaces, walk-in closets, and beautifully appointed baths with radiant heat. A finished daylight lower level adds flexible space for media, recreation, fitness, or entertaining. Custom landscaping and hardscaping lead toward the waterfront, while a detached barn with private guest suite above provides additional space for visitors, extended family, or a studio. On-demand generators serve both buildings. Remarkably private yet just 10 minutes from Yarmouth Village and convenient to Portland, 156 High Winds Drive combines substantial private waterfront, coveted western exposure, and exceptional craftsmanship in an extraordinary coastal Maine setting.

Full Property Details for 156 High Winds Dr

General

  • Price: $4,250,000
  • HOA FEE: $125/month
  • HOA FEE FREQ.: Annually
  • Taxes: $50,071 (2027)
  • Status: Coming Soon / No Show
  • Type: Single Family
  • Source: MREIS
  • MLS ID: 1683612
  • Updated: 10/8/2026
  • Added to Site: 4 day(s) ago

Interior

  • Number of Rooms: 10
  • Interior Features: 1st Floor Bedroom, Bathtub, In-Law Floorplan, Pantry, Shower, Storage, Walk-In Closet(s), Primary Bedroom w/Bath
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Dishwasher, Disposal, Dryer, Gas Range, Refrigerator, Washer, Tankless Water Heater, Other
  • Flooring: Tile, Wood

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Upper Level

Additional Information

  • Security/Safety: Security System

Exterior

  • Porch/Patio/Deck: Deck, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking Features: Paved, 5 - 10 Spaces, Detached, Inside Entrance

Location

  • County: Cumberland
  • Subdivision: High Winds

School Information

  • High School District: Yarmouth Schools

Community

  • Association: Yes
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Central Air Conditioning
  • Heating Type: Gas Bottled, Forced Air, Radiant

Utilities

  • Sewer: Quasi-Public
  • Water: Public

Structural Information

  • Architectural Style: Colonial
  • Construction: Wood Frame, Wood Siding
  • Basement: Yes
  • Basement Desc.: Interior Entry, Daylight, Finished, Full
  • Roof: Metal, Shingle
  • Windows: Double Pane Windows
  • Square Feet: 4,244
  • Sq. Ft. Source: Other
  • Finished Total: 4,244 Sq. Ft.
  • Finished Above Grnd: 3,326 Sq. Ft.
  • Finished Below Grnd: 918 Sq. Ft.
  • Year Built: 2019

Additional Structures

  • Other Structures: Barn(s)

Lot Features

  • Lot Size (Acres): 2.26
  • Lot Size (Sq. Ft.): 98,445.6
  • Street/Road Desc.: Private Road, Paved
  • Zoning: LDR
  • Lot Description: Irrigation System, Near Public Beach, Near Town, Neighborhood, Subdivided, Suburban, Level, Landscaped

Water Features

  • Water Front: Yes
  • Water Front Name: Broad Cove

Green Features

  • Energy Efficient: Ceiling Fans, Water Heater, Insulated Foundation, Thermostat

Financial Considerations

  • Association Fee: $1,500
  • Assoc Fee Freq.: Annually
  • Tax Amount: $50,071.84
  • Tax Year: 2027

Disclosures and Reports

  • Block: 1B
  • Lot Number: 11

Listed by Legacy Properties Sotheby's International Realty (207) 780-8900

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 156 High Winds Dr —

  • Legacy Properties Sotheby's International Realty

    207-780-8900

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 156 High Winds Dr

School District:Yarmouth
NameGradesDistance
Yarmouth Elementary School
121 Mccartney Street, Yarmouth, ME 04096
2-41.9 mi
William H Rowe School
52 School Street, Yarmouth, ME 04096
K-12 mi
Frank H Harrison Middle School
220 Mccartney Street, Yarmouth, ME 04096
6-82 mi
Yarmouth High School
286 West Elm Street, Yarmouth, ME 04096
9-121.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 156 High Winds Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/08/2026
Listed
$4,250,000
5.59%
MLS
1/05/2024
Sold
$4,025,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 156 High Winds Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$47,931
71%
$3,294,200
201%
2024
$28,080
9%
$1,093,900
—
2023
$25,677
9%
$1,090,800
—
2022
$23,583
9%
$1,090,800
—
2021
$21,598
1%
$1,090,800
—
2020
$21,380
4%
$1,090,800
—
2019
$20,506
165%
$1,087,300
151%
2018
$7,725
-26%
$434,000
-29%
2017
$10,500
1%
$611,900
—
2016
$10,439
-14%
$611,900
9%
2015
$12,102
—
$561,300
—
2014
$12,124
-2%
$561,300
—
2013
$12,349
—
$561,300
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 156 High Winds Dr

$
Down Payment
%
$
%

$
$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Legacy Properties Sotheby's International Realty (207) 780-8900

Similar Properties near 156 High Winds Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

15 Sturdivant Rd, Cumberland, ME 04110 - Photo 1
$4,900,000

15 Sturdivant Rd  Cumberland, ME 04110

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 3,531
    Sq. Ft.
Listed by Legacy Properties Sotheby's International Realty
32 Edgewater Rd, Falmouth, ME 04105 - Photo 1
$3,500,000

32 Edgewater Rd  Falmouth, ME 04105

  • Single Family
  • Active
  • 3
    Beds
  • 5
    Total Baths
  • 3,668
    Sq. Ft.
Listed by RE/MAX By The Bay
13 Foreside Rd, Falmouth, ME 04105 - Photo 1
$5,150,000

13 Foreside Rd  Falmouth, ME 04105

  • Single Family
  • Active
  • 5
    Beds
  • 6
    Total Baths
  • 4,678
    Sq. Ft.
Listed by Legacy Properties Sotheby's International Realty
2 Drew Rd, South Portland, ME 04106 - Photo 1
$3,450,000

2 Drew Rd  South Portland, ME 04106

  • Single Family
  • Active
  • 3
    Beds
  • 2
    Total Baths
  • 2,148
    Sq. Ft.
Listed by Legacy Properties Sotheby's International Realty

Just Listed near 156 High Winds Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

304 Blanchard Rd, Cumberland, ME 04021 - Photo 1 Just Listed
$599,000

304 Blanchard Rd  Cumberland, ME 04021

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 2,936
    Sq. Ft.
Listed by Real Broker
10 Fairwind Ln Ext, Cumberland, ME 04110 - Photo 1 Just Listed
$3,150,000

10 Fairwind Ln Ext  Cumberland, ME 04110

  • Single Family
  • Active
  • Updated 4 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 5,751
    Sq. Ft.
Listed by Legacy Properties Sotheby's International Realty
99 Delwin Dr, North Yarmouth, ME 04097 - Photo 1 Price Reduced
-$175,000 (-12.07%)
$1,275,000

99 Delwin Dr  North Yarmouth, ME 04097

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,528
    Sq. Ft.
Listed by Legacy Properties Sotheby's International Realty
85 Mill Ridge Rd, North Yarmouth, ME 04097 - Photo 1 Just Listed
$730,000

85 Mill Ridge Rd  North Yarmouth, ME 04097

  • Single Family
  • Active
  • Updated 22 hours ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,402
    Sq. Ft.
Listed by Regency Realty Group

Price Reduced near 156 High Winds Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

40 Powell Rd, Cumberland, ME 04110 - Photo 1 Price Reduced
-$4,000 (-0.55%)
$725,000

40 Powell Rd  Cumberland, ME 04110

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,540
    Sq. Ft.
Listed by U&R Real Estate
99 Delwin Dr, North Yarmouth, ME 04097 - Photo 1 Price Reduced
-$175,000 (-12.07%)
$1,275,000

99 Delwin Dr  North Yarmouth, ME 04097

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,528
    Sq. Ft.
Listed by Legacy Properties Sotheby's International Realty
57 Oaken Rdg, North Yarmouth, ME 04097 - Photo 1 Price Reduced
-$7,000 (-1.93%)
$355,000

57 Oaken Rdg  #57  North Yarmouth, ME 04097

  • Condo
  • Active
  • Updated 1 day ago
  • 2
    Beds
  • 3
    Total Baths
  • 1,428
    Sq. Ft.
Listed by Keller Williams Realty
53 Mill Rd, North Yarmouth, ME 04097 - Photo 1 Price Reduced
-$49,000 (-8.18%)
$550,000

53 Mill Rd  North Yarmouth, ME 04097

  • Single Family
  • Active
  • Updated 21 hours ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,126
    Sq. Ft.
Listed by River's Edge Realty LLC

Recent Sales near 156 High Winds Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

59 Maeves Way, Cumberland, ME 04110 - Photo 1 Sold
$3,995,000

59 Maeves Way  Cumberland, ME 04110

  • Single Family
  • Closed
  • Updated 10 days ago
  • 4
    Beds
  • 6
    Total Baths
  • 4,306
    Sq. Ft.
Listed by RE/MAX By The Bay
Sold by Legacy Properties Sotheby's International Realty
185 Woodville Rd, Falmouth, ME 04105 - Photo 1 Sold
$3,650,000

185 Woodville Rd  Falmouth, ME 04105

  • Single Family
  • Closed
  • 5
    Beds
  • 6
    Total Baths
  • 6,666
    Sq. Ft.
Listed by RE/MAX By The Bay
Sold by Legacy Properties Sotheby's International Realty

156 High Winds Drive, Yarmouth, ME 04096 (MLS# 1683612) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 156 High Winds Drive is currently listed for $4,250,000 and was received on October 08, 2026. Want to learn more about 156 High Winds Drive? Do you have questions about finding other Single Family real estate for sale in Yarmouth? You can browse all Yarmouth real estate or contact a Coldwell Banker agent to request more information.

Tour this property