Provincetown MA Luxury Homes

MLS Number 22404743

• Condo
• Bedrooms 2
• Bathroom 3
• Square Feet 1,035
• Town Provincetown

This fully renovated West End penthouse in Ptown's most sought-after location, nestled within the historic Victorian house known as The Sandpiper. The meticulously designed 1,035-sq ft residence features two bedrooms, each with an en suite bathroom, thoughtfully positioned on opposite ends of the unit to ensure the ultimate in privacy. With three balconies you'll enjoy breathtaking, unobstructed ocean views. It offers private beach gate access and an on site property manager. This stunning condo featuring sleek porcelain floors, open floor plan with a chic living room with a full-size fireplace, dining room and a contemporary kitchen, outfitted with stainless steel appliances. A private laundry room, complete with a full-size washer and dryer and two private off-street parking spaces.One of the most coveted features of this penthouse is the exclusive, large cobblestone courtyard directly on Commercial Street--an amenity rarely found and highly sought after in Ptown.

Listed by David L White of OwnerEntry.com

MLS Number 22404326

• Residential
• Bedrooms 1
• Bathroom 2
• Square Feet 3,126
• Town Provincetown

Don't miss this rare opportunity to own a historic piece of Provincetown. The Packard Gallery is a beloved landmark on Commercial Street, successfully owned by celebrated artist Anne Packard for the past 35 years. Originally built as a church, this property has been beautifully maintained. Special touches such as the iconic cupola, arched windows and solid steel girder construction are defining features that have stood the test of time. The gallery itself is full of light with hardwood floors, superior acoustics and plenty of storage. In addition to the stunning gallery space, there is a one bedroom unit with full kitchen in the rear of the building with a secluded back patio. There are options to use your imagination, keep or reduce the gallery space with a residential unit or convert back to a private residence as it once was. This unbeatable East End location, steps from the Bay with 4 parking spaces is unheard of. It is truly one of a kind! Seller welcomes offers with requests for buyer concessions.

Listed by Shelby Zawaduk and The Rose Kennedy Team of Gibson Sotheby's International Realty

MLS Number 22404634

• Condo
• Bedrooms 4
• Bathroom 5
• Square Feet 1,904
• Parking Spaces 2

Meticulously restored 1870s Second Empire home thoroughly re-engineered for luxurious 2025 living. Spanning 1,904 sq. ft. the four-bedroom home is situated atop Center St across from the Library. Restored stained-glass double doors welcome you to a grand scale open living space, featuring 12 ft. ceilings, wide plank Sawyer-Mason hardwood floors throughout, beautiful, coffered ceilings, a custom cherry mantel gas fireplace, state-of-the-art HVAC, and RH light fixtures & chandeliers. The gourmet kitchen with island & peninsula includes GE Cafe Collection appliances, a pantry & half bath. All four bedrooms offer luxurious en-suite bathrooms. The ground-floor bedroom is ideal for an office and the second-floor primary suite has views of the bay. Enjoy the front exclusive patio bathed in morning light, or relax in the fully fenced back patio, with sunset views of the monument. A unique opportunity to own a fully restored historic home. The seller will consider requests for buyer concessions

Listed by Iskren Georgiev of Gibson Sotheby's International Realty

MLS Number 22402844

• Residential
• Bedrooms 7
• Bathroom 4
• Square Feet 2,958
• Parking Spaces 10

Venture onto the veranda of this elegant Greek Revival single-family home and let the bay breezes transport you to a bygone era as you enjoy views of Commercial Street and the harbor. Centrally located on a hill with rooftop and monument views, this unique property boasts 7 bedrooms, 4 bathrooms, and a spacious living room with newly refinished floors perfect for gatherings and entertaining. The several bonus spaces, including an outbuilding, offer endless possibilities for a home office, art studio, or home gym. This well maintained three-story home is filled with period charm, featuring restored antique windows, built-ins, and a large porch with a second-floor balcony. The generous property includes ample parking and a side yard awaiting your landscape design vision. With an extremely strong rental potential, the property is fully rented for the 2024 season. Seller welcomes offers with requests for buyer concessions.

Listed by Iskren Georgiev of Gibson Sotheby's International Realty

MLS Number 22402724

• Condo
• Bedrooms 3
• Bathroom 4
• Square Feet 2,993
• Parking Spaces 3

Welcome to 44 Winslow Street, a meticulously designed modern residence offering the ultimate in luxury and comfort. This 2,993 sq. ft. home features 3 spacious bedrooms and 3.5 beautifully appointed bathrooms, perfect for both relaxation and entertaining. The gourmet kitchen, equipped with high-end GE appliances, is a chef's dream. The expansive open-concept living area boasts modern finish carpentry, exquisite built-ins, and glass railings, providing a seamless flow between each level. Step outside to your private oasis featuring a fully fenced yard and heated saltwater pool. The outdoor kitchen is complete with plumbing, a grill, and a TV, ideal for summer gatherings. An irrigation system ensures your landscaping stays lush and green. Enjoy the low-maintenance lifestyle with Hardie shingles and Azek trim. The heated and air-conditioned garage offers convenience, additional workspace and future expansion possibilities. Located in Winslow Farm, this home offers independent ownership, delivering the next best thing to a single-family home. Short-term rentals are permitted and it's being offered mostly furnished for your utmost convenience.

Listed by Holmes Group and Brett E Holmes of Kinlin Grover Compass

MLS Number 22403105

• Condo
• Bedrooms 3
• Bathroom 3
• Square Feet 2,546
• Parking Spaces 1

Epic 3-Bedroom Duplex Condominium in the Heart of Provincetown. Introducing the crown jewel at Wharf of the Seven Oars. You'll feel like you're traveling down a quaint alley in a European village where an unassuming entrance just off Commercial Street leads you into a grand living area where water views have been expecting you.Enter a home where sophistication and coastal living collide, and discover this 2,546 square foot duplex condominium, perched in the vibrant heart of Provincetown. This isn't just a residence; it's a bonafide sanctuary...and a BIG one.Running the entire length of the building imagine two full floors of elegant, easy luxury. The first level is a grand open-concept oasis, where living, dining, and lounging spaces merge in harmony while also existing as clearly defined spaces. Ascend to the upper level, where the primary bedroom/living room suite beckons you through a 9-foot slider to a deck offering panoramic 180 degree views that stretch from Ptown Harbor to the far reaches of your imagination. Watch as the marina, Town beach, Long Point, the monument, and the library compete for center stage as day turns to night. Peer through windows that frame the ever-entertaining tableau of Commercial Street below. Peer through windows that frame the ever-entertaining tableau of Commercial Street below. And if water views are your jam, prepare to be moved from both levels of this haven. In the kitchen, a 6-burner Bosch propane range and oven await with Shaker cabinets and stainless appliances framed by the textured beauty of tasteful gray and white honed granite countertops. Warm yourself by one of the two sleek, high-end linear electric fireplaces, their flames flickering with promises of cozy nights. The primary suite is a symphony of luxury, featuring a fireplace, a serene office area, a soaking tub for dream-weaving, and a spa-sized shower with dual rain heads and open-air transom windows that allow light, air, and views to Long Point. The en suite guest bedroom on the first level is no mere afterthought. It's a grand space with a bay window overlooking Commercial St and a walk-in closet, offering a getaway within a getaway for your guests. But wait. There's more? Yep! A dedicated laundry room where you can wash, dry, AND fold your clothes with space to spare. A generous first-level bonus room ripe for an office, den, or impromptu creative explosion is ready for your vision. AND there's an extra-large storage room off the primary suite, where shelves yearn to keep your treasures tidy. Design details and craftsmanship enchant with oak flooring, coffered ceilings, and custom molding at every turn. Large glass panels along the staircase let light cascade in highlighting the open feeling and flow. Extra-wide staircases allow for grand entrances (and exits), and generous wall space awaits your art collection. Comfort AND convenience? Get out! Central air and heat ensure your comfort in every season, an off-site parking space (location TBD) keeps your chariot safe. Dive into the extraordinary. Live the luxurious life you've always dreamed of in the heart of Provincetown with this remarkable duplex condominium. Don't pinch yourself - this is for reals. Seller welcomes offers with requests for buyer concessions.

Listed by David M Nicolau and Nate Butera of Gibson Sotheby's International Realty

MLS Number 22404793

• Residential
• Bedrooms 10
• Bathroom 8
• Square Feet 2,124
• Parking Spaces 9

Nestled on a charming side street in the heart of Provincetown, this delightful 10-bedroom 8 bathroom property, currently operating as the popular Chicago House guesthouse, is a hidden gem. The main level boasts a delightful parlor room, a fully renovated kitchen, and the owner's quarters complete with a private bath. There are two beautifully appointed guests rooms, each featuring its own private bath. On the second level, you'll find seven inviting guest rooms, serviced by four private and three shared baths. Guests love the covered porch--a perfect spot for sipping morning coffee or unwinding with an afternoon cocktail while soaking in the vibrant atmosphere of the town. A standout feature of this property is the ability to accommodate nine parking spaces, a rare find in such a central location! Additionally, solar panels are installed, generating enough electricity to nearly eliminate the electric bill. With over 2,100 square feet of living space and soon-to-be connection to the sewer for 10 bedrooms, this property presents endless possibilities for its next owner, whether you're looking to continue its successful guesthouse operation or explore new ventures. Reviews highlight the warm hospitality and personalized service that make each stay special. Guests often rave about the peaceful ambiance, impeccable cleanliness, and the delightful breakfast offerings. Many visitors return year after year, drawn by the sense of home and the exceptional experiences shared at The Chicago House. Whether you're seeking a romantic getaway, a family vacation, or a solo retreat, The Chicago House Guesthouse offers an unforgettable experience that captures the essence of Provincetown's charm and history. Seller welcomes offers with requests for buyer concessions.

Listed by The Beach Buoys of Gibson Sotheby's International Realty

MLS Number 22403916

• Residential
• Bedrooms 3
• Bathroom 2
• Square Feet 1,369
• Town Provincetown

Incredible opportunity to live in the lovely East End of Provincetown with deeded beach access, water views, and impressive rental history! This unique home, with frontage on both Commercial and Bradford Street, offers the convenience of parking for up to five cars. As you enter the foyer, you are welcomed by the light-filled open living space designed for comfort and style, featuring contemporary and practical built-in seating, a cozy fireplace, and a large window that frames stunning views of Cape Cod Bay and your deeded path to the beach that is just feet away. The inviting dining area is perfect for gatherings, highlighted by a charming window seat. The kitchen has access to the backyard, outdoor shower, and parking. A stunning staircase leads you to the second floor, where you will find the master bedroom with water views, a full bathroom, and two more spacious bedrooms. Don't miss your chance to own a piece of Provincetown's serene East End!Seller welcomes offers with requests for buyer concessions.

Listed by The Rose Kennedy Team of Gibson Sotheby's International Realty