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.
CondoProperty Type
1986Year Built
$509Price/Sq.Ft.
$400/moHOA Dues
1 garage spacesParking
Listed by Joshua Lagasse• RE/MAX Realty One
Contact: jlagasse@remax.net
Bought with Colin McKeith• Oberg Insurance & Real Estate Agency, Inc.
Unparsed Address: 29 Winsor Green Road 29, Naples, ME 04055
Directions: From Exit 48 (Westbrook), take ME-302 W toward Windham/Naples. Follow ME-302 W approx. 25 miles to Naples. Turn left on Winsor Green Rd and follow to #29.
Public facts
Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: —
Style: Condo/Co-op
Year Built: —
Year Renovated: —
County: Cumberland County
APN: —
Home facts updated by county records on May 14, 2026
Around this home
Schools
Songo Locks School
Public PreK-2 • Assigned • 0.9mi
Lake Region Middle School
Public 6-8 • Assigned • 4.2mi
3/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
3/10 Heat Factor
7 days above 93° expected this year, 16 days in 30 years
4/10 Wind Factor
10% chance of strong winds in next 30 years
2/10 Air Factor
1 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Naples, ME • 04055
Average low and high temperatures (°F)
28
11
32
10
44
25
54
35
65
46
76
56
81
62
80
55
73
49
61
40
47
31
33
16
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
85/ 100
Very good sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.3 hrs
5.5 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$717,000 – $868,000
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