VRBO is part of the HomeAway family, the world leader in vacation rentals with over 1 million listings. We offer the largest selection of properties for any travel occasion and every budget. We’re committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together. Learn More

Spectacular Waterfront Home on Southold Bay - One of a Kind!

You sent a message to this owner.

Watch the Tall ships all day from 3 different levels!


Last updated: 12/02/2014
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:2 nights
  • Internet:Yes
  • Pets considered:No
  • Wheel chair accessible:No

Southold house description

Located in the private beach community of Reydon Shores, 'The Roost' was newly built in 2007-2008. This property is bordered by over 400 acres of forever wild land which abounds with astounding wildlife and rare birds. It boasts a 140 degree water view of Southold bay with huge glass windows on three sides to optimize the views. Off the Master Bedroom is a cozy sky deck perfect for sunrises and spectacular sights of the east ends continuous show of Yachts & Tall Ships. Also located upstairs are two additional bedrooms with queen beds. Downstairs has a spacious laundry closet, another bedroom with a full bath. The Kitchen, dining and living room are a combined 'Huge great room' with incredible water views with endless glass windows and doors. The living room has a 50 inch HD flat screen, wireless Internet and stereo.

Fishing Charters : 1-FISHING TRIPS; Specializing in teaching children (and adults) the art of fishing. Our waters hold many species of different fish from prime fluke, scup, sea trout, striped bass, bluefish, blackfish, flounder, tuna and shark. Capt'n Roo is one of the best fisherman on the north fork and loves to share his fishing skills with his quests. Capt'n Roo has the patience and knowledge to make sure the kids (and adults) have an unforgettable fishing experience. We supply the bait, tackle, boat ( 25ft center console inboard) and tales for a great time. All you need is sunscreen, drinks, lunch and towels just in case you might want a quick swim. At the end of the trip- all your fish will be cleaned and properly packaged- ready to eat.

Boating adventure tours: 2- ADVENTURE TOURS;
Your family can choose from swimming, clamming, snorkeling, fishing, and sightseeing .You choose the adventure and set out for a 2 ,4 or 6 hr. trip . For example our most popular trip is the 6 hr. excursion too Southampton Ocean beach. The day begins ( with 15 minute safety briefing and rules set by the captain.) at 9:45 am. We Load the boat (docked on site) with beach gear and were off with a full hour of boating thru the great peconic bay , going thru the Shinnecock Canal and crossing the great Shinnecock Bay where we beach the boat on bayside where you have a short walk over the dunes to one of the most spectacular Ocean Beaches on the east coast. There our quests can choose to remain on the beach (for apprx. 3 hrs) or continue thru the shinnecock inlet for some exciting offshore fishing for the prized doormat fluke and Striped Bass.At apprx. 2:30pm we pick up the beachers and head back towards the northfork. We arrive back at the dock at appr. 4:oopm

Clam Bakes * Cookouts * Barbeques:
Cap'tn Roo is a retired professional caterer specializing in outdoor catering. So kick back settle in with the sights while your clambake is prepared and served on site.

Note: All Fishing ,Cruises, Adventure Trips and Catering are subject to weather and tides so planning events need flexibility.

Prices for all activities given upon request.


We offer vacation rentals for every budget

Choose from a wide variety of properties

No booking fees

Free to book with no hidden costs

We help you travel with confidence

Every listing is guaranteed against fraud

Experienced property owners or managers

Average five years in the business

Property Type

  • House
  • 2500 sq. ft.

Accommodation Type

      • Vacation Rental

      Onsite Services

          • Housekeeper Optional


          • Non Smoking Only
          • Pets Not Allowed
          • Unsuitable For Elderly Or Infirm
          • Wheelchair Inaccessible

          Bedrooms: 4 Bedrooms, Sleeps 8

          • Bedroom 1: 1 king

            Plus Bunkbeds in adjacent room /closet...moreless

          • Bedroom 2: 1 queen


          • Bedroom 3: 1 queen


          • Bedroom 4: 1 twin/ single


          • Room 5


          • Master Bedroom is huge with a pillow topped custom mattress that makes sleeping an incredible experience. Off the bedroom is a sky deck boasting the best water view southold has to offer. This is a great way to greet the day at sunrise watching ospreys catch fish, Yachts and Tall Ships cruising by and local fisherman tending their catch. Additionally there is a walk in closet with a set of bunkbeds for extra sleeping and a beautiful master bath with a clawfoot soaking tub as well as a spacious shower equipped with a rain showerhead....moreless

          Bathrooms: 2 Bathrooms

          Other Amenities

              • SUNSET CRUISES and water taxi service to and from; Greenport, Shelter Island, & Sag Harbor for Shopping, Dining and activities. An example would be an afternoon cocktail cruise leaving the dock Late afternoon- (your choice of time).We arrive at a destination of your choice such as Sag Harbor where we drop you off at the Town Dock for an evening in town. Pickup time is at your discretion but curfew is 11:00pm. Prices upon request....moreless


              • Books
              • CD Player
              • DVD Player
              • Radio
              • Satellite / Cable
              • Stereo
              • Television


              • Adventure
              • Away From It All


              • Autumn Foliage
              • Bay/Sound
              • Churches
              • Cinemas
              • Forests
              • Library
              • Marina
              • Museums
              • Playground
              • Restaurants
              • Synagogues
              • Winery Tours

              Local Services & Businesses

              • ATM/Bank
              • Fitness Center
              • Groceries
              • Hospital
              • Massage Therapist
              • Medical Services

              Leisure Activities

              • Antiquing
              • Beachcombing
              • Bird Watching
              • Horseback Riding
              • Outlet Shopping
              • Paddle Boating
              • Scenic Drives
              • Sight Seeing
              • Walking

              Location Type

              • Beach
              • Waterfront

              Sports & Adventure Activities

              • Cycling
              • Deepsea Fishing
              • Fishing
              • Fly Fishing
              • Golf
              • Golf Privileges Optional
              • Hiking
              • Jet Skiing
              • Pier Fishing
              • Roller Blading
              • Sailing
              • Scuba Diving Or Snorkeling
              • Snorkeling
              • Sound/Bay Fishing
              • Surf Fishing
              • Swimming
              • Tennis
              • Water Skiing
              • Wind-Surfing


              • Dining Area
              • Seating for 6 people


              • Activities Guide
              • Air Conditioning
              • Basic Soaps
              • Ceiling Fans
              • Clothes Dryer
              • Filtered Water
              • Fireplace
              • Hair Dryer
              • Heating
              • Internet
              • Iron & Board
              • Laundry Soap
              • Linens Provided
              • Local Maps
              • Parking
              • Telephone
              • Towels Provided
              • Washing Machine
              • Water Cooler
              • Wireless Internet


              • 4 Ring Stove
              • Coffee Maker
              • Cooking Utensils
              • Dishwasher
              • Freezer
              • Grill
              • Ice Maker
              • Lobster Pot
              • Microwave
              • Oven
              • Pantry Items
              • Refrigerator
              • Stove
              • Toaster


              • Balcony
              • Barbecue
              • Beach Chairs
              • Beach Towels
              • Boat Dock
              • Fish Cleaning Table
              • Kayak / Canoe
              • Lawn / Garden
              • Outdoor Grill
              • Outdoor Grill Gas
              • Patio
              • Porch / Veranda
              • Unscreened Porch / Veranda

              House Cleaning

                  • Housekeeper Optional


                  Write a review 5
                  from 17 traveler reviews
                  Rental basis: Per property
                  Dates Nightly Weekend Night Weekly Monthly * Event
                  Holiday season
                  Nov 1 - Jan 2, 2015
                  2 night min stay

                  Additional information about rental rates

                  Fees and Rental Conditions:

                  • Property Damage Protection $49
                  • Refundable Damage Deposit $300
                  • Cleaning $125
                  • Taxes Not included


                  The above rates are for a six person rental- Please note that larger parties are subject to a surcharge based on the number of guests.

                  Please wait... Pay with confidence

                  Paying through this free service protects your payment up to $10,000 against listing fraud. If you are not paying through HomeAway Payments always call the owner at the number listed on our website and never use instant money transfer services such as Western Union and MoneyGram.

                  Don't forget your vacation protection! Get protected now

                  Adding our Vacation Protection services can make sure your getaway goes smoothly, no matter what. We offer Cancellation Protection, Carefree Rental Guarantee, and Damage Protection so you can truly relax.

                  Protect your payments in case you need to cancel.
                  Guarantee the rental meets your expectations.
                  Ensure you're prepared in case of accidental damage.


                  Last updated: 12/02/2014
                  Check availability
                  23 Available
                  21 Unavailable
                  22 Today
                  23 Selected dates


                  40 Miles
                  Nearest Airport
                  3 Miles
                  Nearest Barpub
                  Founders Landing
                  7 Miles
                  Nearest Ferry
                  7 Miles
                  Nearest Golf
                  Island Links
                  3 Miles
                  Nearest Train
                  20 Miles
                  Nearest Motorway
                  3 Miles
                  Nearest Restaurant
                  Founders Landing

                  Car: Recommended

                  We are located on the north shore of Hogs neck in Southold. This area is very special as it is very quiet, serene and mostly still exists in its wild state. It is home to Cedar Beach, Goose creek, Paradise point and three prominent wineries. The Indian Museum and Custer Telescope ( famous for study of the solar system) make their home here as well. The North Fork Triathalon is held here every year in the beginning of July mainly due to the extreme low volume of traffic. Horses, pony drawn buggys, runners , Bicyclists and walkers feel they have the roads to themselves.


                  Owner info

                  Contact us

                  Speaks: english

                  Guestbook comments from the owner

                  1 of 6


                  • Watch the Tall ships all day from 3 different levels!

                    Watch the Tall ships all day from 3 different levels!

                  • aerial view

                    aerial view

                  • Master Bedroom feels like you're under the stars!

                    Master Bedroom feels like you're under the stars!

                  • Guest Bedroom #2

                    Guest Bedroom #2

                  • Great Room (Kitchen, Dining, Living Area)

                    Great Room (Kitchen, Dining, Living Area)

                  • short walk to private Beach

                    short walk to private Beach

                  • sunset bonfire

                    sunset bonfire

                  • Gorgeous beach just steps away

                    Gorgeous beach just steps away

                  • Breathtaking views

                    Breathtaking views

                  • Whether its sunrise or sunset- it does'nt get better than this

                    Whether its sunrise or sunset- it does'nt get better than this

                  • Spectacular views from house

                    Spectacular views from house

                  • M.B. Skydeck is perfect for sunrise coffee or a sunset cocktail !

                    M.B. Skydeck is perfect for sunrise coffee or a sunset cocktail !

                  • Huge state of the art Kitchen- with a perfect view !

                    Huge state of the art Kitchen- with a perfect view !

                  • living room

                    living room

                  • Catch big fish with cap'tn Roo

                    Catch big fish with cap'tn Roo

                  • The bite is always on!

                    The bite is always on!

                  $550 per night (USD)

                  4 Bedroom / 2 Bathroom
                  Sleeps 8

                  View calendar: Updated 12/02/14
                  Minimum stay: 2 nights
                  Dates are unavailable
                  Please stay a bit longer. A stay of nights or more is required for these dates.
                  This listing requires that rentals start on a .
                  Get an instant quote
                  Member since: 2010
                  Speaks: english
                  • Response time: Within a few hours
                  • Response rate: 100%
                  • Calendar last updated: 12/02/2014
                  Email owner

                  914 469-3095

                  Please wait... Pay with confidence Guaranteed, secure, with no booking fees Learn more
                  Add vacation protection services to your booking

                  Three services to protect your trip:

                  Protect your payments in case you need to cancel.

                  Guarantee the rental meets your expectations.

                  Ensure you're prepared in case of accidental damage.

                  Get it now

                  Share this property via Email

                  Spectacular Waterfront home on Southold bay - one of a kind!

                  Southold #281433ha

                  4 BR  2 BA  Sleeps 8

                  You must be signed in to share this property by e-mail

                  Share this property via Email

                    Please correct the following errors and resend:
                  • Enter one or more valid email addresses separated by commas.
                  • Oops! You have exceeded the limit of 10 email addresses.
                  • Your message may not contain markup. Please remove the markup and try again.