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Property Description

Welcome to 29 Winsor Green Road, a beautifully maintained condominium within the desirable Winsor Green Condominium Association in Naples, Maine. While the Lakes Region rests under a quiet winter landscape, this meticulously renovated 2018 home invites you to imagine long summer days on the water just ahead, with Brandy Pond and Long Lake only moments away.

Inside, the home offers a thoughtful layout with bright, open living spaces designed for comfort and ease year-round. The kitchen features quartz countertops, generous cabinetry, and efficient workspace, flowing seamlessly into the dining and living areas. Bedrooms are well-proportioned, including a primary suite with a private bath, while an additional bedroom and bathrooms provide flexibility for guests or a home office. An attached garage, second-floor dedicated laundry area, and ample storage make this property equally suited for both seasonal or full-time living.

Winsor Green is known for its shared waterfront amenities, including docks, picnic areas, and expansive common green space that extends to the shoreline. Boat slips on Brandy Pond and Long Lake are increasingly scarce, making this unit's deeded lake access & slip especially valuable. While the lake may be frozen today, summer brings effortless access to boating, kayaking, paddleboarding, swimming, and lakeside relaxation just steps from home.

Located near the heart of the Naples Causeway, the property offers easy access to waterfront dining, marinas, live music, seasonal events, and local shops. Four-season recreation defines the lifestyle here, from summer days on the water and fall foliage hikes to winter snowmobiling, ice fishing, and skiing at nearby Pleasant Mountain.

Professionally managed and designed for low-maintenance ownership, this property offers the rare opportunity to purchase now and be fully prepared for summer in the Maine Lakes Region. Schedule your showing or visit the open house 12-2pm on Sunday, January 11, 2026.

Overview

Property Status
Sold
MLS ID
1648873
Property Type
Condo
Year Built
1986

Features & Amenities

Total Area
1,376 Sq.Ft.
Neighborhood
Naples
Architecture Styles
Other, Colonial, Row-End
Water Frontage
ROW to Water, Lake/Fresh Water, Dock, Deeded, Boat Slip, Beach Rights
View Description
Scenic, Trees/Woods
Garage Spaces
1.0
Water Source
Private, Well
Roof
Shingle
Lot Features
Well Landscaped, Rolling/Sloping, Near Golf Course, Near Public Beach, Near Shopping, Ski Resort, Subdivided
Parking
Reserved Parking Spaces, Auto Door Opener, Reserved Parking, Paved, Inside Entrance, 1 - 4 Spaces
Heat Type
Electric, Propane, Direct Vent Heater, Heat Pump
Air Conditioning
Heat Pump
Laundry Room
Upper Level
Appliances
Tankless Water Heater, Washer, Refrigerator, Microwave, Gas Range, Dryer, Dishwasher
Other Interior Features
Bathtub, Shower, Primary Bedroom w/Bath
Sewer
Quasi-Public, Septic Design Available, Septic Tank, Shared Septic
Substructure
Slab, Poured Concrete
Disability Features
Level Entry
Sales Price
$700,000
Real Estate Tax
$4,300/yr
HOA
$400/mo
Zoning
Rural

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29 Winsor Green Road 29

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for your interest in 29 Winsor Green Road 29, Naples, ME 04055

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