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$2,200,000
3 Beds ⋅ 3 Baths ⋅ 22603268 MLS
At the landing in quaint Paine Hollow, you will find this vintage waterfront Cape where timeless, classic design and an exceptional location come together to create a home and memories to be enjoyed for generations. The house is sited on .80 of an acre, with 206' of beach frontage, overlooking Blackfish Creek. Included is an additional .55-acre level, partially cleared, wooded, unbuildable lot that has served as overflow parking and off-season boat storage. The custom-designed and built single-owner home features wide pine-plank floors, knotty pine paneling, wainscoting, custom-handcrafted doors, cabinets, and vanities, and skim-coated plaster walls. Attention to detail and craftsmanship are evident throughout. The first floor features an open-concept layout, with a stately brick fireplace outfitted with a propane gas insert anchoring the main living space. Expansive sliding glass doors capture panoramic views, inviting the outdoors in and connecting the main living areas and the private primary ensuite directly to the bayside decks. Practicality meets thoughtful planning in the kitchen ell, where a transitional hallway provides convenient access to a powder room, pantry closets, a laundry room, and internal entries to the two-car garage and basement. Upstairs consists of two front-to-back bedrooms with a shared generous full bath, offering elevated waterviews. Whether hosting summer guests or enjoying a quiet weekend by the water, the home feels equally suited to entertaining and peaceful retreat. Premium features that enhance the property's utility include an oversized, two-car garage with insulated doors, a spacious walk-in attic, and a full basement accessible from two interior points. Modern essentials like a whole-house Generac generator and an outdoor shower complete the offering. The property is served by a four-bedroom septic system with a recent inspection report available.

300 Paine Hollow Road, Wellfleet
$899,000
4 Beds ⋅ 2 Baths ⋅ 22603196 MLS
Welcome to Twin Oaks, a private and comfortable 4-bedroom, 2-bath Cape-style home nestled on a secluded 1-acre wooded lot. Tucked away at the end of a sand driveway in the peaceful Paine Hollow bayside neighborhood, this property offers the perfect blend of privacy and natural beauty.The waters of Blackfish Creek are just down the road, and the home abuts acres of protected conservation land with scenic walking trails right outside your door. Whether you're looking for a year-round residence or a tranquil retreat, this property offers an exceptional opportunity to enjoy nature at its finest.The home is served by a 5-bedroom septic system, which has passed inspection, offering potential flexibility for future expansion, subject to local regulations.The oil tank needs upgrading and the seller is asking the buyer to take responsibility for a new oil tank at buyers expense and after the closing. The WFD will issue a 6 month waiver for the buyer to accomplish the installation.Don't miss this rare opportunity to own your own private sanctuary in one of the area's most peaceful settings.

50 Amy's Way, Wellfleet
$799,000
4 Beds ⋅ 2 Baths ⋅ 22603185 MLS
Tucked away at the end of a quiet road, this 4-bedroom, 2-bath Cape offers the perfect blend of privacy, convenience, and Cape Cod living. Set on a generously sized lot just 1.5 miles from Mayo Beach, you'll enjoy easy access to Wellfleet's renowned beaches, restaurants, galleries, and outdoor recreation while returning home to your own peaceful retreat. Inside, the sun-filled open floor plan features hardwood floors, a cozy fireplace, two first-floor bedrooms, and a full bath, offering flexibility for guests or single-level living. Upstairs, you'll find two spacious bedrooms & an additional full bath. Step outside to a private backyard with a deck & outdoor shower--ideal after a beach day. The walkout lower level provides outstanding potential to create more living space, whether you envision a media room, home gym, playroom, or guest suite. An ideal opportunity as a year-round residence, vacation getaway, or investment property in one of Cape Cod's most desirable coastal communites.

3098 State Hwy Rte 6 Highway, Wellfleet
$989,000
3 Beds ⋅ 3 Baths ⋅ 22602986 MLS
Historic, charming and beautifully renovated this 3-bedroom antique home is thoughtfully updated structurally and cosmetically. Its timeless character has been preserved. Ties to the area's early saltworks and fishing industries, this special property offers a rare blend of historic significance and modern comfort. Filled with natural light, the main house features 2 beds + 2 baths, inviting living spaces and a spacious family room addition that creates an ideal gathering place for family and friends. Original charm is complemented by tasteful renovations; so warm and functional! Attached annex provides exceptional flexibility; soaring ceilings, living room w wood stove, sleeping loft, additional bedroom and a full bath. Perfect for guests, extended family, a home office, or creative retreat. Beautifully landscaped grounds create a private and picturesque setting. A detached two-car garage is topped by an unfinished studio space, offering endless possibilities for artists, hobbyists, remote work, or extra storage. Rich in history, character, and versatility. Unique Wellfleet property offers a rare opportunity to own a distinctive home to live, work, create and entertain.

45 Old Paine Hollow Road, Wellfleet
$2,100,000
3 Beds ⋅ 3 Baths ⋅ 22602799 MLS
Beautifully tucked away on a quiet, sand road on the western side of Ocean View Drive, you will find this long held family home which has been beautifully expanded and maintained since its original form in 1950. Designed first by mid century modern architect Paul Mitarachi, the stunning, original, 2 bedroom structure offers double height ceilings in the living room and a magical second level which invites the outside in and highlights the surrounding peace and privacy of the seashore woods. From here a light and bright, renovated kitchen connects this area to a spacious primary suite and generous screened-in porch ensuring easeful, modern living in an incomparable location. Set on 3.11 acres of land surrounded by Cape Cod National Seashore, here footpaths lead through the woods to hidden treasure Spectacle pond and the ocean can be heard from the moment you arrive. With access to ocean beaches, the north Wellfleet kettle ponds and even a quiet route to town center down Long Pond Road, this newly offered home combines mid century architecture with modern upgrades, expansion and renovation creating a comfortable, striking and warm place for all seasons. Come explore.

1125 Ocean View Drive, Wellfleet
$799,000
3 Beds ⋅ 2 Baths ⋅ 22602662 MLS
Welcome to Clam Cake cottage in picturesque Pleasant Point, Wellfleet. Perched on a hill with water views of Blackfish Creek tidal estuary, this charming 3BR, 1.5 bath 1920's seasonal cottage is the perfect bayside beach house. Just a short walk to the waters of nearby Pleasant Point Landing where you will enjoy swimming, kayaking, shell fishing, spectacular nature walks and marshland views. The mini-split A/C provides both heating and cooling. You will relish relaxing on the screened porch, savoring the gentle breeze and enjoying life in your Wellfleet beach house. Drinking water is supplied by the neighborhood Pleasant Water system. Good rental history.Take a look soon.

125 Pleasant Point Road, Wellfleet
$869,000
3 Beds ⋅ 2 Baths ⋅ 22602379 MLS
Tucked into a peaceful marshside neighborhood, this inviting 3 bedroom, 2 bath home blends privacy, coastal beauty, and classic Cape Cod charm. The open kitchen, living, and dining area flows seamlessly onto an oversized deck, creating the perfect space for relaxing or entertaining after a day at the beach.Located just minutes from ocean beaches, bay side sunsets, nature trails, galleries, and local dining, the home offers easy access to all that makes Wellfleet and the Outer Cape so special. A successful rental for many years, this property presents an exceptional investment opportunity, vacation getaway, or year-round residence.Offered furnished.

285 Blue Heron Road, Wellfleet
$1,200,000
5 Beds ⋅ 3 Baths ⋅ 22601798 MLS
Step into a piece of history with this extraordinary Wellfleet property. Rarely does a property with this much opportunity come to the market. Set on a pastoral 1.5 acre parcel and tucked back a generous distance from Route 6, you are enveloped in a peaceful oasis with glimpses of Drummer's Cove. The property offers endless possibilities with the historic main house, a large insulated and heated post and beam barn studio with attached garage and a charming one bedroom cottage. The main house boasts character throughout that can only be found in homes from this time period with the original layout, built-in's and much of the original hardware. The home features four bedrooms and two bathrooms, a sunporch, sunny kitchen with breakfast nook, and a dining room for larger gatherings. The second floor offers additional sleeping areas and plenty of storage. There are spaces to gather together and spaces for quiet retreat. Step outside and be greeted by mature plantings, lovely herb gardens and open spaces to enjoy outdoor living. Across the yard you will find the post and beam barn which offers abundant natural light and the open spaces present opportunities for many uses; home office, art studio, hang out space, future pool house etc. Tucked along the edge of the property is a charming cottage offering a loft bedroom, efficient kitchen, private deck, half bath and outdoor shower. Use for family and friends or additional income and rent either year round or seasonally. This property is a canvas for those who appreciate homes with character and soul. A chance to infuse your own vision into this already captivating gem. Whether you're drawn to the beautiful grounds or enchanted by its timeless allure, this property invites you to become part of its storied legacy.

1551 Us Route 6, Wellfleet
$1,795,000
4 Beds ⋅ 4 Baths ⋅ 22601437 MLS
Major price improvement! Discover a truly unique property tucked away in the heart of Wellfleet that provides versatility. This quality-built home features a gourmet kitchen, four bedrooms, 4 baths, over 4000 sf and an adaptable space perfect for separate living quarters and potential income. Whether used as a multi-generational setup or a seamless single-family home, the interior boasts large yet inviting rooms with three fireplaces and charming nooks. Outdoor living is enhanced by multiple surrounding decks and 1.26 acres. The property also includes a unique ''blank slate'' room ready for a potential indoor pool. Note other idea concepts in the virtually staged photos.For the auto aficionados-find an oversized detached two-car garage and additional garage/s space in the expansive basement. With plenty of room for your boat and beach toys and just in time for summer on Cape Cod a truly versatile home in one of the Cape's most sought-after villages.

85 Pier Road, Wellfleet
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 22601154 MLS
4 bedroom, 3 1/2 bath 3000 sf Post and beam 1982, Ideal location, Quiet neighborhood, Surrounded by nature, Cape cod national seashore and beaches, Summer community. Renovated 2026 bathrooms, kitchen HVAC, flooring and finishes. Interior renovation can still be customized.

205 Blue Heron Road, Wellfleet
$1,995,000
5 Beds ⋅ 5 Baths ⋅ 22502115 MLS
Looking for a resort-style compound with high-end craftsmanship and a rare level of privacy? Welcome to 40 Leilla Rich Drive. Set on a fully-fenced lot with room for a pool, this upscale all-season property is perfect for long summer weekends, entertaining guests or simply unwinding near miles of National Seashore beaches. A dramatic vaulted four-season family room anchors the home. Filled with natural light and overlooking the expansive grounds, it creates an immediate sense of calm from the moment you arrive. Spend your days exactly as you imagined: mornings with coffee and birdsong, afternoons at nearby LeCount Hollow or Marconi Beach and evenings that transition effortlessly from sunset drives along the coast to dinner and live music at the iconic Beachcomber. Back home, gather by the woodburning fireplace or retreat to the comfort of one of the many serene, well-appointed suites. Enjoy a first-floor primary bedroom with spa-inspired indoor/outdoor bath amenities and its own courtyard. Work remotely from your dedicated home office with custom-built cabinetry. Entertain in your chef's kitchen complete with wet bar. Accommodate guests in their second-story wing with its own living room, kitchenette, bathroom, sunlit porches and a separate entrance. Additional highlights include a finished basement ideal for a home gym or movie room, convenient first floor laundry and a sizeable three-car garage with room for a boat and substantial storage for bikes, paddleboards and beach chairs. Whether you're seeking a sophisticated summer residence, a year-round work-from-home sanctuary by the sea, or a legacy property for years to come, Leilla Rich represents a compelling opportunity to secure your place on the Outer Cape.

40 Leilla Rich Drive, Wellfleet

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