OceanView at Falmouth’s 30+ year reputation for excellence in retirement living expands to Cumberland with an exciting 50+ cottage neighborhood, including NEW Special Program access at OceanView!

  • Maintenance-free living with 100% refundable entrance fee
  • Two spacious, customized floor plans with many options and a flexible construction timeframe
  • NEW – Special access to OceanView at Falmouth programs and Care Continuum including:
    • Fitness classes, movies & dining options
    • Falmouth House Assisted Living
    • Legacy Memory Care
  • OceanView at Falmouth’s experienced Management Team oversight
  • Convenient location near Cumberland Center and adjacent to Twin Brook Recreation Facility, a 250 acre park
  • On-site pool and community center for fitness programs, social events and activities of all kinds
  • Network of walking, hiking, snow shoeing and cross country ski trails
  • Golf Fore Life Program – complimentary access to:
  • Solar-powered, environmentally friendly and ecologically responsible – “green living” at its finest!


Cumberland Crossing Model Cottage
  • Two energy efficient cottage floor plans with the ability to customize
  • Both floor plans offer two spacious bedrooms, a great room with gas fireplace, two full baths, 4-season sunroom, fully applianced kitchen, laundry and attached garage with storage
  • Standard customization options include granite countertops, stainless appliances and hardwood floors
  • Standard solar – photovoltaic electricity
  • Standard full service generator
  • Options:
    • Loft with bedroom, bath and open to below living space
    • 2-car garage or widened driveway
    • Solar hot water
    • Solar generator


Maintenance Staff Raking Leaves

Enjoy your retirement and let Cumberland Crossing staff do the chores! Maintenance-free living is truly stress-free living!

  • Full-time interior and exterior maintenance, PLUS 24-hour emergency maintenance
  • Landscaping, lawn and garden care
  • Snow removal, shoveling, salt/sanding
  • Housekeeping monthly
  • Security service after-hours
  • RN Wellness Office – weekly hours
  • Annual health review by RN, with updating of File of Life medical history
  • Transitional support and priority access to Falmouth House Assisted Living or Legacy Memory Care at OceanView
  • 24-hour Emergency Medical Response System in every cottage


Cumberland was once part of North Yarmouth, ME, but was incorporated in 1821, just one year after Maine became a state. The town was officially named by Ephraim Sturdivant when the new town government elected him to do the task. It has long been a mostly agricultural town, with a rich farming history including small family farms, dairy farms, market farms, apple orchards and greenhouses.

Although only a small number of working farms remain, the Cumberland Fair, one of the state’s larger agricultural fairs, has been held here at the end of September every year since 1868. Chebeague Island, once a part of Cumberland, formed its own town in 2007. According to the United States Census Bureau, the town has a total area of 26.25 square miles and stretches inland from Cumberland Foreside, on Casco Bay, to West Cumberland, which borders Windham.

The population of Cumberland was 7,211 as of the 2010 census.

  • The Cumberland Crier – The Cumberland Crier is a weekly newsletter that is sent out by the town to community members and has information about what is going on in our community, such as road construction, waste & recycling pick-up, recreation registration, community events, council meetings and agendas, election notices, and more. This emailing service is also used in emergency situations such as weather alerts, road closures, water main breaks, or health/safety concerns.
  • The Cumberland Farmers Market – In operation in Cumberland since 1996, The Cumberland Farmers Market provides the community with a high-quality array of locally raised and produced goods.
  • Cumberland Fair – Sponsored by the Cumberland Farmers Club, this town fair has been in existence for almost 150 years. In addition to traditional agricultural events showcasing the cooking, craft and animal husbandry skills of town residents, the Fair features harness racing on a 1/3-mile clay track.
  • Cumberland Town Parks include Broad Cove Reserve, Twin Brook Recreation Area, The Town Forest, Rines Forest and Knight’s Pond, with combined trails that extend over 10 miles.
  • Val Halla Golf Club – This 18-hole professional course has been recognized as the “Best Municipal Course” in Maine by Golf Digest and the “Best Value in Maine” by the New England Golf Guide. It houses the home of the Maine State Golf Association as well as a full-service restaurant, Rachel’s on the Green.
  • Chebeague & Cumberland Land Trust – a non-profit land conservation organization that has conserved nearly 900 acres since 1988. Many of these properties are open to the public for recreation and enjoyment.
  • Aging in Place Cumberland – In 2014, community members, working with the Cumberland Town Council, formed the Aging in Place Committee to survey town residents regarding their goals and needs as they approached retirement and beyond. In 2016, the town joined the Global Network for Age-Friendly Cities and Communities, designated by the World Health Organization. Aging in Place Cumberland has developed into a thriving, vibrant organization. Through an energetic corps of volunteers and many partners, they provide a host of valuable services, programs and resources.

Town of Cumberland Website


Portland – Maine’s most dynamic city, only 20 minutes away, is home to first-class dining, art galleries, sports teams, the Portland Symphony, three colleges, two hospitals, ferry and cruise ship terminals and the Portland International Jetport.

Visit Portland Website

Outdoor Recreation

  • Casco Bay offers boating adventures of all kinds. Recommended: Peak’s Island Ferry rides!
  • Biking and hiking trails thread through the coastal communities.
  • Merrymeeting Bay, the East Coast’s third-largest estuary, provides spectacular birdwatching, fishing and boating.
  • Lighthouses abound along the Maine coast. You will find over ten active lighthouses within an hour’s drive from Cumberland Crossing!
  • The YMCA in Freeport is a full-service facility, offering lap swimming daily.
  • Skiing in its myriad forms can be enjoyed as closely as stepping out your back door, or as swiftly as schussing down one of Maine’s world-class ski areas



Don Wessels joins OceanView at Falmouth as the Sales Associate for their new satellite community, Cumberland Crossing by OceanView, in Cumberland, ME.

Don brings over 30 years sales experience with The Portland Press Herald/Maine Sunday Telegram, The George T. Johnson Company and, most recently, at The Highlands of Topsham (since 2009). Prior to his employment at The Highlands he ran the Music School at River Tree Arts in Kennebunk.

Now taking reservations, call (207) 781-4460


Cumberland Crossing by OceanView is the latest implementation of lessons learned by John Wasileski over a lifetime of designing and developing sustainable retirement living communities with a care continuum.

His foresighted partnership with community leaders, initially Portland Area Lutheran Services in 1974, sparked a passion for creating quality, environmentally-sensitive homes for seniors in maintenance-free, socially active village settings. That first experience led to the construction of the Main Lodge and the first twenty OceanView at Falmouth Cottages in 1986. As the community grew, John developed expertise in fulfilling the needs of residents and their families, while becoming an integral part of the local community. Honoring the natural world in his development process has always been a priority for John: he was awarded the Governor’s Award for Business Excellence by Governor Baldacci in 2004, the Environmental Leadership Award from the Institute for Family-Owned Business in 2017, and was recognized at the 2017 eco-Excellence Awards for Business Leadership (top winner).

OceanView Owner, John Wasileski, with son Chris and granddaughter Haley.

OceanView Owner, John Wasileski, with son Chris and granddaughter Haley.

John also brought the care continuum concept to Topsham, where he established both The Highlands and Highland Green, giving more individuals the choice to enjoy a stress-free, active and engaged retirement lifestyle, knowing that quality support and assistance will be available when needed.

In 2008, John’s son, Chris Wasileski, started working with his father, primarily on development project management. Chris’ team received the 2014 MEREDA Notable Project award for the Falmouth Schools Redevelopment project at OceanView. Chris has a background in Political Science with a focus on Environmental Politics, Energy Policy, and National Security as it relates to national resources. His research and interests have led to a focus on clean energy and energy efficiency in his Real Estate development career, primarily in the senior housing industry.

After over 30 years of growth and success at OceanView, John’s vision is expanding in cooperation with his son. This Maine-owned and managed family business is branching out with Cumberland Crossing by OceanView, a satellite community only 5.5 miles north of the main Falmouth campus. With priority access to Falmouth House Assisted Living and Legacy Memory Care at OceanView, Cumberland Crossing residents will enjoy a beautiful, rural setting at the center of Cumberland, with close proximity to the ocean and the many cultural opportunities of Portland, Maine’s largest city. Cumberland Crossing will provide new generations of retirees the opportunity for maintenance-free retirement living with a strong sense of community and peace of mind for the future, while maintaining OceanView at Falmouth’s emphasis on sustainability, alternative energy sources, and “green and local” practices.


Cumberland Crossing Model Cottage

Model Cottage Open House

 We invite you to come visit our new Model Cottage,…
Interior sprinklers, electrical wiring, and plumbing work are all complete on 56 Little Acres Drive.

Construction Flyover Video & Update!

It's a beautiful day in the neighborhood, as building continues…
Penny Asherman, Board President of the Chebeague & Cumberland Land Trust

Chebeague & Cumberland Land Trust Luncheon Presentation

Penny Asherman, Board President of the Chebeague & Cumberland…
Cumberland Crossing's first residents - Ron and dog Zoe.

Cumberland Crossing's First Resident Moves In!

Cumberland Crossing is pleased to welcome its first residents…
56 Little Acres Drive Roof

Construction Update

Cumberland Crossing's first model cottage has been sold!…
Cumberland Crossing Model Cottage

New Model Cottage Open Houses!

We invite you to come visit our new Model Cottage, where…
5 Periwinkle Drive Sod

Construction Update

Another beautiful afternoon at Cumberland Crossing with the…
56 Little Acres Drive Loft Framing

Construction Update

2nd floor loft is now all framed up at 56 Little Acres Drive,…
56 Little Acres Drive Studs and Exterior Wall

Construction Update

Walls going up at 56 Little Acres Drive, under fair summer…