14 Trailside Way

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living room 28
living room 29
living room 26
kitchen 1
kitchen 8
kitchen 7
kitchen 9
kitchen 3
kitchen 6
living room 5
living room 9
living room 1
living room 3
living room 16
living room 19
fireplace 3
living room 20
living room 21
living room 24
living room 6
living room 25
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stairs leading to the loft
stairs to the loft
primary bath2
primary bath
primary bath3
primary bath4
primary bedroom 1
primary bedroom 4
primary bedroom 7
Primary bedroom
balcony 1
balcony
Bedroom 1-2
bedroom 1-3
bedroom 1-4
bedroom 2-1
bedroom 2-3
hallway
hallway2
hallway3
hallway4
hallway5
second flr bath 2
second flr bath 3
second flr bath 4
second flr bath 5
second flr bath 7
second flr bath
second flr bath1
stairs to basement
basement living room 6
basement living room 7
basement living room 5
basement living room 9
basement living room 14
basement living room 16
basement living room 3
basement living room 4
basement living room 1
basement living room 2
basement living room 10
basement living room 11
basement living room 12
basement living room 13
basement living room 15
basement living room 17
basement living room 18
basement living room
basement bedroom 1
basement bedroom
IMG_1992
exterior 6
exterior 12
Railing
View water
exterior 11
exterior 16
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walk way 1
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Active
$899,900
4 beds1,994 sqft
14 Trailside Way, Bridgton, ME 04009
Est: $5,542/moGet pre-approved
Single FamilyProperty Type
15.84 acresLot Size
2025Year Built
$451/sq ftPrice per sq ft
$2,000/yrHOA Fees

Description

Nestled slope-side at the Pleasant Mountain Ski Area, now part of the renowned Boyne Resorts, (owner of Sunday River, Sugarloaf, and Loon Ski Resort) this stunning newly constructed custom-built log home is the essence of luxury and adventure. Imagine stepping out of your front door and onto the ski trails, where endless winter fun awaits. The soaring cathedral ceilings and wall of windows frame views of surrounding mountains and Moose Pond. Unique lighting fixtures and tasteful décor add an elegant...Nestled slope-side at the Pleasant Mountain Ski Area, now part of the renowned Boyne Resorts, (owner of Sunday River, Sugarloaf, and Loon Ski Resort) this stunning newly constructed custom-built log home is the essence of luxury and adventure. Imagine stepping out of your front door and onto the ski trails, where endless winter fun awaits. The soaring cathedral ceilings and wall of windows frame views of surrounding mountains and Moose Pond. Unique lighting fixtures and tasteful décor add an elegant touch to the warm wood finishes throughout the home. The main floor is open concept living, dining, and kitchen area perfect for entertaining. The living room fireplace and soaring stone chimney adds character and warmth. Two spacious bedrooms provide cozy retreats, complemented by a stunning full bathroom featuring attractive tiled shower and flooring. Step outside onto the wrap-around porch, where open railings allow you to soak in panoramic views as you entertain around the firepit. Ascending to the loft, you'll discover the primary bedroom, that boasts high ceilings and its own unique lighting. Indulge in the spa-like custom tile shower with a glass enclosure and your own sitting area. The lower-level space features a cozy living room with a gas fireplace that opens to a game room--ideal for unwinding after a day on the slopes. A fourth-bedroomed offers additional accommodation for guests. The slider leads to a second deck with custom railings. This property comes completely furnished, making it a turn-key opportunity for those seeking their dream vacation or investment home. This property already has an impressive rental history with future income on the books. Downtown Bridgton has dining, shopping, and entertainment options. Nearby snowmobile, ATV trails and scenic hiking paths. Experience the thrill of Ski-in/Ski-out living. Asked about the mortgage rate buy-down by a local lender, with acceptable contract, terms and conditions apply. 3 Bedroom Septic.
3 days on Market
  • Listed by: Barbara Howe 207.583.7510 barbarahowe990@gmail.com • Pine Tree Realty of Maine
Last updated: 10/02/2026 03:44 PM • Source: Maine Listings, MLS#: 1682785

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$5,542 per month

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Principal and Interest

$4,804

Property Taxes

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HOA Dues

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Property Information for 14 Trailside Way

Property Details
  • Taxes: $6,853 / year
  • MLS Type: Residential / Single Family Residence
  • County: Cumberland County
  • Architectural Style: Chalet, Contemporary, New Englander
  • Furnished: Furnished
  • View: Mountain(s), Scenic, Trees/Woods
  • Has Waterfront: No
  • Waterfront Features: Lake/Fresh Water, Nearby, Public
  • Zoning: Residential
Building Information
  • Year Built: 2025
  • Lot Size: 15.84 AC / 689,990 SF
Summary
Location and General Information
  • Water View: Yes
  • Page: 291
  • Directions: Route 302 to Mountain Road, past Pleasant Mountain Ski Lodge, Trailside Way is on your right, follow up to #14 on the right.
  • Latitude: 44.050404
  • Longitude: -$70.81
  • Water Body Type: Lake, Pond
  • Water Body Name: Moose Pond
Taxes and HOA
  • Association Fee: $2,000.00
  • Association: Yes
  • Tax Lot: 17/B
  • Tax Book Number: 39018
  • Tax Map Number: 7
  • Tax Year: 2025
  • Association Fee Frequency: Annually
  • Tax Annual Amount: $6,853.00
Parking
  • Parking Features: Paved, 1 - 4 Spaces, On Site
  • Vehicle Storage: No Vehicle Storage
  • Has Attached Garage: No
  • Has Garage: No
Virtual Tour
Property
Lot Information
  • Lot Features: Near Public Beach, Near Shopping, Neighborhood, Rural, Ski Resort, Rolling Slope, Landscaped, Wooded
  • Lot Size Acres: 15.84
  • Lot Size Area: 15.84
  • Lot Size Source: Survey
  • Lot Size Square Feet: 689990.4
  • Lot Size Units: Acres
  • Roads: Association, Dead End, Paved, Private Road
  • Road Frontage Type: Private Road
  • Road Surface Type: Paved
  • Tree Growth: false
Property and Assessments
  • Above Grade Finished Area: 1444.0
  • Below Grade Finished Area: 550.0
  • Building Area Source: Public Records
  • Building Area Total: 1994.0
  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Surveyed: Yes
  • Year Built: 2025
Building Features
  • Levels: Multi-Level
  • Levels: Multi-Level, Three or More
  • Foundation Details: Poured Concrete
  • Construction Materials: Log, Log Siding
Financial Information
  • List Price/SqFt: $623.20
Green Features
  • HERS Certified: No
Utilities
  • Electric: Circuit Breakers
  • Gas: Bottled
  • Sewer: Private Sewer, Shared Septic
  • Water Source: Private
  • Water Heater: On Demand, Tankless
Interior and Exterior Features
Exterior Features
  • Roof: Shingle
Interior Features
  • Amenities: 1st Floor Bedroom, Washer Hookup, Storage, Primary Bedroom w/Bath
  • Appliances: Dishwasher, Dryer, Microwave, Electric Range, Refrigerator, Washer
  • Bathrooms Full: 2
  • Bathrooms Total Decimal: 2.0
  • Bathrooms Total Integer: 2
  • Bedrooms Total: 4
  • Fireplaces Total: 2
  • Laundry Features: Washer Hookup
  • # Full Baths Level 1: 1
  • # Full Baths Upper: 1.0
  • Rooms Total: 8
  • Basement: Interior Entry, Walk-Out Access, Daylight, Finished, Full
  • Has Fireplace: Yes
  • Patio And Porch Features: Deck
  • Cooling: Central Air
  • Has Cooling: Yes
  • Heating: Electric, Propane, Direct Vent Furnace, Forced Air, Zoned, Radiant
  • Has Heating: Yes
  • Flooring: Tile, Wood, Luxury Vinyl
  • Interior Features: 1st Floor Bedroom, Storage, Primary Bedroom w/Bath
Room Information
Kitchen
  • Kitchen Countertop: Granite
Laundry
  • Laundry Room Amenities: Washer Hookup
Rental
Rent Information
  • Land Lease: No

Property History for 14 Trailside Way

DateEvent & SourcePriceAppreciation
Oct 1, 2026

Listed (Active)

Maine Listings #1682785

$899,900—
Aug 18, 2026

Withdrawn

Maine Listings #1657247

$899,900—
Apr 10, 2026

Listed (Active)

Maine Listings #1657247

$995,000—
DateEvent & SourcePrice
10/01/2026

Listed (Active)

Maine Listings #1682785

$899,900
08/18/2026

Withdrawn

Maine Listings #1657247

$899,900
04/10/2026

Listed (Active)

Maine Listings #1657247

$995,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 14 Trailside Way

Taxable ValueLand$500,000Additions$287,591Total$787,591
Tax Record2025$6,498 ($542 / month)
Home Facts
Total Finished SqFt825 SqFtAbove Grade Finished SqFt825 SqFtCountyCUMBERLANDAPNBRGT M:007 L:017 S:B T:014

Schools near 14 Trailside Way

This home is within Regional School Unit 61 Msad 61.
Rating
School
Type
Grades
Distance
Stevens Brook School
Public - PK to 5
Lake Region Middle School
Public - 6 to 8
Lake Region High School
Public - 9 to 12
Crooked River Elementary
Public - 3 to 5
Rating
School
Distance
Stevens Brook School
PublicPK to 5

Lake Region Middle School
Public6 to 8

Lake Region High School
Public9 to 12

Crooked River Elementary
Public3 to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 14 Trailside Way, Bridgton, ME 04009

14 Trailside Way is a single family home for sale in Bridgton, ME 04009. This property was listed for sale on October 1, 2026 by Pine Tree Realty of Maine, it's currently listed at $899,900. This listing's school district is Regional School Unit 61 Msad 61. Nearby schools include Stevens Brook School, Lake Region Middle School and Lake Region High School. 14 Trailside Way is a 4-bed, 2-bath, 1,994 sqft single family home built in 2025.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Pine Tree Realty of Maine

Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal, noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved.