West Dennis Massachusetts homes for sale starting at Fifty Thousand Dollars

$5,875,000 - West Dennis, MA

18 Wendy Way West Dennis, MA - Welcome to Tranquility Base. Properties at the end of the fingers of West Dennis come for public sale so rarely only three have ever been recorded in the MLS. It's no wonder, with its views and luxuries. Plus this property is a boater's paradise, with a 72' deep water dock tucked conveniently along the side of the property (and permission for a second dock out front) and the calm waters of Bass River to lead you right out to Nantucket Sound. Among the $1M+ in updates that were done to the house in '24/'25 are: A brand new sea wall, all new decks, landscape, irrigation, a brand new kitchen, updated steel framing, new hardwood floors, sliders, and new HVAC. Views can be enjoyed from almost any room, and the open concept and window placement bring in every mood of sunlight throughout the day. Four en suite bedrooms plus ample overflow space and laundry up and down make this home an epic place to gather. Just around the corner (or the bend in the river) is West Dennis Yacht Club, as is West Dennis Beach. Only 30 minutes from the bridge or 15 minutes to the airport, this is an escape you can get to in a hurry.

$2,649,000 - West Dennis, MA

14 Harbor Way West Dennis, MA - Presenting a unique opportunity to own a stunning home on the Fingers in West Dennis. This exquisite property boasts breathtaking views of Nantucket Sound from every window, ensuring you capture the beauty of this phenomenal location at all times.Designed with taste and elegance, the home features two spacious decks perfect for viewing or relaxing, a patio off the deck surrounded by a beautifully landscaped yard, and plenty of space for family and pets. A NEWLY INSTALLED FLOATING DOCK can accommodate a 40' boat, and the SEAWALL was REPLACED and ELEVATED in 2021 for added security.For your convenience and peace of mind, this home is equipped with hurricane shades and tinted windows to maintain privacy and shield from the sun. The thoughtful owner has also included a 16 KW Kohler generator, extra insulation, a home security system, an irrigation system, and a wall safe.The interior is designed for accessibility and comfort, featuring a main floor en suite, ADA compatible doors and a staircase prewired for a stair-lift. Enjoy the convenience of a low entrance shower and the warmth of a first-floor wood-burning stove.

$2,400,000 - West Dennis, MA

6 Baker Way West Dennis, MA - SERIOUS CASH FLOW, Experience owning a truly unique home boasting 280-degree panoramic ocean views of Nantucket Sound and Swan River. Completely renovated in 2014 with top-tier building materials, from composite storm-grade roofing shingles to cedar siding and Azek & Trex decking. Most windows and doors are Jend-Weld hurricane-grade, and the house is elevated for added assurance. Inside, discover custom features while maintaining classic Cape Cod coastal charm with floor-to-ceiling hand-sanded pickled pine walls and reclaimed hardwood flooring from standard NH. The bathrooms and kitchen feature marble-tiled flooring inlays, granite counters in the kitchen, and stunning blue glass tiles in the bathrooms, echoing the ocean's hues. Historical features and whimsical touches abound, including a mantelpiece from the USS Constitution ''Old Ironsides'' and repurposed port windows and sconces. Enjoy energy-efficient upgrades like a tankless hot water heater and a propane burner. Upgraded to a 4-bedroom septic in 2012. Nestled in pristine private dunes on a white sandy beach, this home offers the perfect blend of luxury and coastal living. Don't miss out on this Cape Cod retreat

$1,200,000 - West Dennis, MA

36 Uncle Barneys Road West Dennis, MA - Historical homes and water lovers!! Step back in time and experience the charm of old Cape Cod in this antique home. Built in 1900 and filled with character, this 4BR, 2BA home sits on a rare .88-acre lot in an area of smaller parcels—offering space, history, and views of Bass River. From the wood floors to original moldings, built-ins, and cozy nooks, every inch tells a story. Enjoy the covered patio or sunroom with views of Bass River just across the street. With a town way to water steps away, it's ideal for kayaking, paddleboarding, or watching the boats go by. The flexible layout offers natural light, spacious rooms, and vintage charm throughout. Some updates are needed, but the home has been well loved. Located ~1.3 miles to West Dennis Beach, 0.4 miles to a public boat ramp, and close to marinas and boat clubs, this is a dream location for boaters and beach lovers. A rare opportunity to own a piece of Cape Cod's history and make it your own. Professional photos coming soon. Priced under assessed value! Failed Title V. Sold ''AS IS'' Location, low taxes and phenomenal beaches in Dennis make this a great opportunity for a value add. Buyers & agents to do own due diligence.

$879,000 - West Dennis, MA

401 Main Street West Dennis, MA - Welcome to #101, The Crown Jewel of The Columns, a stunning 2-bedroom + bonus room/den, 2-bath 1375 sq ft home featuring 2 exclusive-use patio areas that create a seamless blend of indoor & outdoor living. This residence beautifully marries modern elegance w/classic charm, highlighted by a restored historic fireplace and contemporary bathrooms, fixtures, & design elements throughout. With approximately 10-foot ceilings, the space feels bright, airy, and inviting—truly a sanctuary to call home. Additional highlights include an inviting kitchen with butlers pantry, cozy den and the convenience of two dedicated parking spaces and deeded storage. Experience comfort and style in this exceptional property. Set on over 13 acres of conservation land, The Columns provides a tranquil escape while remaining conveniently located just off Cape Rte 28. Experience the best of Cape Cod living in this remarkable property where classic history meets modern elegance. Don't miss your chance to own a piece of Cape Cod's heritage—schedule your private showing today and immerse yourself in the beauty and charm of The Columns!

$799,000 - West Dennis, MA

111 School Street West Dennis, MA - Renovated in 2023, this exceptional two-level home in the highly sought-after West Dennis area offers endless possibilities. Located less than a mile from the pristine shores of West Dennis Beach, it perfectly blends modern comfort with coastal charm. Whether you're looking for a spacious year-round residence, a relaxing vacation retreat, or an income-generating investment, this home's versatile layout and prime location provide the ideal foundation for your vision. Currently, rental income for the year is approximately $45,000 which would transfer to new owners.Don't miss the opportunity to make this beautifully updated property your own.

$674,000 - West Dennis, MA

178 School Street West Dennis, MA - Charming Cape Cod-style home located close to popular West Dennis Beach features a blend of historic character and modern amenities. Key features include 3 bedrooms, 1.5 bathroom, and a generous lot size, making it a desirable property for those seeking a coastal lifestyle. The home retains its vintage charm with classic architectural details, while offering proximity to nearby beach,shops, dining, and outdoor recreational activities. Buyers/buyers agents to verify all information contained herein.

$565,000 - West Dennis, MA

401 Main Street West Dennis, MA - Discover the perfect blend of history and modern comfort in this charming 700 sq ft, 1-bedroom, 1.5-bath home. Unit 201 features exquisite period details, including a beautifully restored fireplace mantle from Captain Obed Baker's residence. The open-concept living and dining area flows seamlessly to your own private 160+ sq ft balcony, ideal for savoring morning coffee or entertaining guests with afternoon refreshments. The contemporary kitchen boasts stainless steel appliances, while a versatile bonus room offers endless possibilities as a library, office, or den. Enjoy the unique charm of glass-encased period etchings alongside modern fixtures and amenities, creating an enviable living experience. Set on over 13 acres of conservation land, The Columns provides a tranquil escape while remaining conveniently located just off Cape Rte 28. Experience the best of Cape Cod living in this remarkable property where classic history meets modern elegance. Don't miss your chance to own a piece of Cape Cod's heritage—schedule your private showing today and immerse yourself in the beauty and charm of The Columns!

$550,000 - West Dennis, MA

855 Main Street West Dennis, MA - 855 Main St in West Dennis is a UNICORN, or perhaps better described as a Mermaid! The property was most recently the retail shop Mermaids on Cape Cod, and it is a RARE FIND. A multi-use property that has recently been used as a two bedroom home and a retail shop. The house sits on Rt 28 for high visibility, with plenty of parking out back on the quarter acre lot. Ideal for retail, a barbershop or salon, a coffee shop or just a comfortable cottage. If you are looking for a place to live and/or run a business, this Mermaid could be calling your name.

$479,000 - West Dennis, MA

43 Pond Street West Dennis, MA - Rarely available pondfront cottage in W. Dennis on Kelley's pond! This delightful two bedroom cottage is quintessential Cape Cod charm with a wood burning fireplace, a new bathroom, ample size kitchen, a screened in porch and deck overlooking the pond with southwestern exposure and beautiful sunsets. Rinse off in your outdoor shower and enjoy the firepit after a day of kayaking or swimming. The Pines on Kelley's Pond consists of 14 individual free-standing condominiums spread out on more than 4 aces on the shore of the pond. Around each unit is an exclusive use area just for that unit. There is a deed restriction whereby the cottage is for seasonal use only (April 1-Nov 30 of each year). The unit will be sold mostly furnished. Not to be missed. Not to be missed!!

West Dennis, Massachusetts listings for sale

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