Welcome to Tito’s and Water — a luxurious waterfront retreat on Pleasant Bay. This stunning home features a main house with an attached carriage house/in-law suite offering extra privacy. With elegant interiors, multiple gathering spaces and a private dock, this home perfectly blends comfort, style, and coastal charm.
- 2 min drive to South Orleans Beach
- 3 min drive to Wequassett Resort & Golf Club
- 10 min drive to The Captains Golf Course
The space
KEY FEATURES:
☀ Beautiful water views of Pleasant Bay
☀ Less than 1 mile to Wequassett Resort
☀ Sleeps 10; 7 bedrooms, 10 beds
☀ 4 full bathrooms + 2 half bathrooms
☀ Private dock
☀ Carriage house (attached) with 2 bedrooms, living room, kitchenette & deck
☀ Fully equipped and spacious chef's kitchen
☀ Indoor dining + outdoor dining areas seats 10 guests
☀ Outdoor kitchen with grill + pizza oven
☀ Spacious patio with cozy firepit + large TV
☀ Gorgeous living room with modern décor, natural light & fireplace
☀ Office with desk, monitor + stunning sea views
☀ Two washer and dryers
☀ Air conditioning
☀ Coffee bar
☀ Large yard overlooking the water with corn hole
☀ Outdoor shower
☆☆ BEDROOMS ☆☆
This gorgeous estate accommodates 10 guests across 7 beautifully appointed bedrooms:
Main House:
1st Floor:
- Bedroom #1: (Primary): King bed + TV + dresser + ensuite bathroom + walk-in closet + water views
- Bedroom #2: King bed + fireplace + dresser + full mirror + connection to a full bathroom
2nd Floor:
- Bedroom #3: King bed + closet + water views
- Bedroom #4: Twin bed + seating area + small closet
- Bedroom #5: Four twin beds (perfect for kids or group) + seating area
Carriage House/In-law Suite (attached):
- Bedroom #6: King bed + dresser + closet
- Bedroom #7: Queen bed + closet
☆☆ BATHROOMS ☆☆
There are four full bathrooms and two half bathroom in this home, each of them stocked with all the essentials you need for the duration of your stay including shampoo, conditioner, body wash, hand soap, blow dryers, and towels.
First floor:
- Bathroom #1: Full bathroom - ensuite in the primary bedroom with a shower.
- Bathroom #2: Full bathroom - walk in shower (entrance via bedroom + hallway)
- Bathroom #3: Half bathroom
Second floor:
- Bathroom #4: Full bathroom - shower with tub
- Bathroom #5: Half bathroom
Carriage House:
- Bathroom #6: Full bathroom - walk in shower
☆☆ KITCHEN & LOUNGE ☆☆
Kitchen: A chef’s dream! Fully equipped with sleek modern appliances, cookware, utensils, and a coffee bar with Keurig. The kitchen flows into a beautiful dining area perfect for family meals. There is also a kitchenette in the carriage house with essentials for a quick brew or light meal.
Dining Room: Stylish indoor dining table for family meals that can seat 10 guests + separate carriage house dining table with a deck and waterviews.
Living Room: Situated on the main level, the spacious living room features comfortable seating, a smart TV, a fireplace, piano, and abundant natural light through large windows showcasing water views.
Office: Located on the second floor, with desk, chairs, monitor, and panoramic sea views – ideal for remote work or quiet reading.
Second Floor Bedroom/Lounge: features a bright and comfortable living space adjoining the room with four twin beds — complete with a seating area and plenty of natural light. It’s a great spot for reading, relaxing, or enjoying a bit of privacy from the main living areas.
Laundry: Laundry room on 2nd floor + a washer/dryer located in the 1st floor hall.
☆☆ OUTSIDE SPACE ☆☆
The exterior area of this home offers a private retreat with breathtaking views of Pleasant Bay.
Main Patio: Large entertaining area featuring a cozy firepit lounge, large outdoor TV, comfortable seating, and corn hole game.
Side Terrace: Located on the side of the home, this inviting area includes a dining table with seating for 10 guests, comfortable seating, and an outdoor kitchen with grill, pizza oven, and prep space.
Private Dock: Direct access to Pleasant Bay with panoramic water views.
Carriage House Deck: Cozy deck with seating for two guests off the carriage house living room.
☆☆ THINGS TO NOTE ☆☆
The garage is off limits to guests and will be locked during your stay.
This is a treasured family home that we are excited to share with guests! Please know there is a gallery wall in the upstairs hallway that connects the bedrooms and office that has some personal family photos. We hope you don't mind that we didn't take this personal touch down.
☆☆ PROXIMITY TO ORLEANS BEACHES ☆☆
- Pleasant Bay – steps away (for views and water access)
- South Orleans Beach – 2 min drive
- Jackknife Beach – 4 min drive
- Nauset Beach (Orleans) – 10 min drive
- Hardings Beach (Chatham) – 12 min drive
- Lighthouse Beach (Chatham) – 15 min drive
- Skaket Beach – 10 min drive
☆☆ NEARBY PLACES IN ORLEANS & CHATHAM ☆☆
- Downtown Orleans shops & cafés
- Cape Cod Rail Trail (bike path)
- Rock Harbor Marina
- Hot Chocolate Sparrow (local favorite café)
- The Knack (casual seafood & burgers)
- Mahoney’s Atlantic Bar & Grill
- The Beacon Room
- The Lobster Claw Restaurant
- Chatham Bars Inn & Wequassett Resort (luxury dining & spa options)
- Chatham Village Market Grocery Store
- Del Mar Bar & Bistro
- Viera on Main
- Impudent Oyster
- Sweet Tomatoes Pizza
- Bluefins Sushi & Sake Bar
☆☆ HOUSE RULES ☆☆
- No events or parties.
- No more than 10 guests max allowed at the home.
- No pets.
- No smoking.
- Quiet hours: 10pm-8am
- No food or drink other than water in the living areas or bedrooms.
- This is a private family home, please be respectful.
★★★ Book Today & Let Us Take Care Of You In Orleans! ★★★
Guest access
You have the entire home to yourself.
