Westbrook CT Real Estate & Homes for Rent

Winter/Off Season and Summer Furnished House Rental. 4 Bedroom/2 Bathroom Cape Close to Greenport Village. Formal Dining Room, Separate Den with TV, Screened Porch with Large Dining Table and Summer Kitchen Set Up. Nicely Manicured Lawn for Enjoyment. October 2023 to May 2024 $3,500 Per Month; SUMMER 2024 - June $9,000; June 28 to July 12 $5,600; Summer Weekly $2,800 (with two week minimum). Permit #0701.

Spacious & immaculate Sound front Contemporary home sitting on a hilltop in Orient, overlooking Long Island Sound to the north & farm fields to the south. Meticulously renovated & professionally designed 4 bedrooms, 5.5 baths with 128 ft of private beach. The ground floor has a large family room with glass doors to a blue stone patio, lawn, & stairs to the beach. This level includes an ensuite bedroom, additional full bath, Malm fire drum, & infra-red sauna. The main floor offers an open floor plan with living/dining/den/kitchen, a 2-sided fireplace, new kitchen, new baths, waterside & farm view decks. A professional ping-pong table, CAC, & outdoor shower are additional amenities. The panoramic Sound and farm views on 1.84 acres offer unique privacy. Offered July 65,000; Aug 75,000. Permit# 1059.

Charming and chic 3 bedroom, 1.5 bath Cottage on Lake Marion with many charming original features. Open, sunny floor plan with common area that opens onto spacious lakefront deck perfect for relaxing, grilling & dining. Wood burning fireplace, fully equipped cook's kitchen, private dock, outdoor shower, & easy stroll to association bay beach. Offered June $8,000; Aug $16,000. Permit# 0692.

Authentic 1770 Cottage in the heart of Orient Village. Lovingly restored & maintained Village home on beautifully landscaped lot, offering private grounds & distant views of sunsets over the bay. Furnished in period antiques, screened-in porch off kitchen, first floor bedroom. Walk to amenities, bay beach, Yacht Club, marina, farm stand & Jitney. Offered Sept $7,000. Permit #0091.

BOOK '24 NOW: Various Rates All Year Long: East Marion, North Fork - Coveted and rare rental (Rates: Season 2023 $87k; June $20k, Aug-LD $40k; Bal of Sept OR Oct $20k; off Season Winter $7000 per mo etc) on the bay in private setting overlooking Bug Light and Long Beach. Spectacular setting with heated, waterside pool. One floor living with many access points to southeast facing deck/terrace. Incredible sunrises - and sunsets reflected on the lighthouse and bay. Living room w/fireplace, sunroom/office, EIK with upscale appliances; DR w/sliders to terrace for outdoor dining. Waterside master suite w/full bath, 3 additional bedrooms w/guest bath. Large 3+ car garage for cars and summer toys. Private yard space for playing and pique-nique'ng. The ultimate North Fork beach house rental for you and your guests. Home sleeps up to 12 people comfortably. Life doesn't get better than at Tara-by-the-Bay. Close proximity to area farmstands, lavender fields, wineries and destination restaurants in Greenport. Permit #0248.

Welcome To Your Greenport Summer Retreat! This Colonial Stunner Has Just Been Completely Renovated To A Very High Standard. This Gem Boasts White Oak Hardwood Floors Throughout, Three Bedrooms, Two Full Bathrooms, Primary Is En-Suite With A Very Large Walk In Closet, A Quaint Gourmet Eat In Kitchen With Stainless Steel Appliances, A Beautiful Den That Could Also Be Utilized As A Workout Area Or Home Office, Large Dining Room Drenched In Natural Light, The Laundry Is Neatly Stacked & Tucked Away. This Beauty Sits On A Wonderful Mature Half Acre, Perfect For Entertaining Guests Or Getting Away From It All And Immersing Yourself In North Fork Peace And Nature. The Perimeter Of The Gorgeous Backyard Is Completely Fenced-In. Kick Back And Savor The Beauty From Your Very Own Screened Porch. Beloved Greenport Village Is Merely A Stones Throw Away. Be Part Of Everything The North Fork Has To Offer: Pristine Beaches, Delectable Restaurants, Local Organic Produce & A Burgeoning Wine Country. Southold Town Rental Permit #1072. July: $15,000. August: $20,000. July/August: $35,000. August to LD: $23,000

Cape-Cod-Style Cedar-Shingle House situated on edge of low bluff. Wooded lot with 2nd-story master bedroom suite/deck. Fantastic 180-degree views of Gardiner's Bay, Bug Lighthouse, Shelter Island, Orient Village and East Hampton with 150-feet of private sandy beach and boat mooring. Permit #0049.

Unwind on Marion Lake and recharge on the Bay! This 2-bedroom, 1 bathroom lakefront cottage is the perfect escape! Just steps away from the Bay allows you to play the day away! Rinse off in the outdoor shower, dine outside on the large deck overlooking Marion Lake and then chill out by the fire pit, making s'mores and creating memories! June:$10K, July:$15K, Aug:$17.5K, Sept:$12K, Oct:$10K, Mem Day-Oct:$60K Permit # 1060

Live the waterfront dream! Imagine having the choice to wake up overlooking Gardiner's Bay or tranquil Marion Lake. This immaculate 3 bedroom, 3 bathroom home offers unparalleled views and much more. Your own Right of Way to the Bay, a mooring for your boat and lakefront access in the backyard! Meticulously appointed and ready for the season! Cozy up by one of the 3 gas fireplaces, indulge in a luxurious soak in one of 2 tubs or have coffee on one of the four waterside balconies. You will not want to leave! Ren permit # 1075

Summer 2024 Rates: June 27-July 11 $15K, Sept4-Oct4 $5K/week: Rare new construction on a quiet side street in Greenport Village, this modern luxury home is the perfect base to explore the beaches, wineries, and farm-to-table dining of the North Fork. Walking distance to downtown Greenport and a short drive from all the major North Fork sights. Or just whittle away your days enjoying the amenities of your luxurious home retreat. Lounge in your heated saltwater pool while sipping a cold drink. Curl up with a book in front of your gas fireplace. Catch up on sleep surrounded by plush bedding on your memory foam mattress. Immerse yourself in the low-key North Fork lifestyle at your private Greenport Getaway.

Spend your summer enjoying all the North Fork has to offer at this Greenport waterfront home with dock and community bay beach. Completely updated with high end touches throughout including chef's custom kitchen with island, 3 bedrooms (2 are en-suite), 4 full bathrooms, expansive waterfront deck, and a lower level entertainment lounge. The perfect place to relax and unwind. Permit# 0955.

Cute as a button cottage located in Gardiners Bay Estates. Tucked away in a private sandy beach community w/ mooring and bulkhead space to tie up to for boaters and a swim platform for summertime fun! Back patio to chill, grill & dine al fresco or screened in porch to kick back & relax, rain or shine. Just 3 miles to Greenport Village, 1/2 mile to Sep's Farm Stand & Lavender By the Bay & only 7 miles to the Orient Ferry. (Southold Town Rental Permit #0775)

Imagine waking up to breathtaking sunrises over the bay and the sound of gentle waves lapping at your doorstep. This Bay front cottage offers the perfect atmosphere to unplug, relax and connect on your own terms. 3 bedrooms, 1 full & 2 half baths, sunroom, outdoor shower and waterside firepit. Book now to create your unforgettable memories! June:$15K, July: $20K, Aug:$25K, Sep:$15K, Oct:$15K, Mem-Oct:$80K Permit # 0449

Experience serenity at this stylishly renovated and tastefully adorned cape in the heart of Greenport village. This expansive residence offers three bedrooms, including a master suite with a private bath, two additional bathrooms, and a convenient home office. The main floor embraces an open-concept design, featuring light-filled dining and living areas, along with a well-appointed kitchen boasting stainless steel appliances. The fenced-in yard creates a tranquil space for stargazing after a day of summer adventures. Just steps away from Greenport Village's restaurants, shops, the Shelter Island Ferry, train, and Jitney bus, and a short distance to popular 67 Steps Beach, this is the perfect location for your unforgettable Greenport summer getaway.

Village Lane summer house - full season rental - historic charm seamlessly blended with modern amenities. Water views. Hardwood floors, lots of light, unique architectural interest with sophisticated decor for the discerning traveler. Rent reflects MD-LD.

Enjoy these breath taking views of Spring Pond out to Gardiner's Bay and Bug Light House. Pass by the renown Lavender Farm on your way to this open concept sun filled home in Gardiners Bay. Offering all the luxuries and amenities within a short distance to a private sandy bay beach. Enjoy August on the North Fork and simply relax. bug

Amazing North Fork home with heated salt water gunite pool located in Grandview Estates featuring 4 bedrooms (1st floor bedroom with ensuite, 2 ensuite guest bedroom on the second floor with 1 additional guest bedroom and guest bathroom) office/den also located on the second floor with a large sitting area and balcony at the landing of the second floor, large, finished basement with projection TV. June $25,000, July $35,000 Permit #0441.

Wonderful North Fork summer rental with in ground pool located on a quiet block with a private community sandy beach at the end of Gillette Drive. This spacious home features 3 bedrooms and 2 bathrooms with a fenced in back yard with beautiful views of a lavender farm. Vineyard, Farm stand and golf course less than a mile away and approximately only 2 miles from the town of Greenport where you can enjoy great activities and fine dining.

Beautifully updated & fully renovated traditional Arts & Crafts home in the heart of Orient Village and one block from Orient Harbor. Gourmet kitchen with Thermador 6 burner/griddle stove, Subzero refrigerator, Bosch dishwasher. Enclosed front porch. Fenced yard, outdoor shower, backyard deck for relaxing, grilling & dining. Professionally landscaped with vegetable garden and outdoor shower. Offered April $9,000; Sept $16,000. Permit #0827.

Impeccably restored 19th Century gem located in the heart of Orient Village with bay views. Close to bay and sound beaches, and a stroll to all village amenities. Featuring 2 parlors, 3 bedrooms, library, office, eat-in kitchen, updated baths, charming garden, out-door dining, and grill, out-door shower. Offered May $7,000; Nov $6,000. Permit #0483.

Relax and enjoy this beautifully appointed bay front house w/ private beach and stunning views of Orient Harbor, Bug Light and Shelter Island. Moor your boat in the bay; kayak, swim, fish or chill on the decks and porches. Basement game room w/ Ping-Pong, TV and games. Conveniently located near shopping, restaurants, ferries, farm stands, vineyards. Available May- $10,000,October - $10,000. Permit# 0026.

Summer 2024. Luxurious Modern Home with Heated Inground Pool in Private Community with Memorable Bay Beach 3 Blocks Away. Short Distance to Golf and Greenport Village. Summer 2024 - June $20,000; July $35,000. Off Season (January to May) - $10,000 per month (single to multiple months considered). Permit # 0634.

Summer rental in Orient. Beautifully renovated inside and out featuring 4 bedrooms, 2.5 baths, plus a spacious backyard with pool. Available for August-LD. RP# 0930

Excellent North Fork vacation location! Tastefully appointed 3BR/4 BA Colonial in pristine, like new condition. Every amenity including a heated, saltwater pool plus 3 living/media rooms. Lovely, quiet neighborhood with a sandy Bay beach & gorgeous Sound beach just minutes away. Nearby CSA farmstands & seafood markets for enjoying farm to table, poolside dining. Renowned restaurants and Greenport's vibrant downtown only 5 minutes away. [Rental permit #0384 Exp. 2/9/2025].

Charming, clean, freshly painted and tastefully decorated, 3 bedroom,1 bath, Greenport bungalow. The enclosed sun-porch is a great extra space to relax on rainy days too. The location~ Just a couple of blocks from a beautiful Bay Beach with boat ramp and amenities. Just down the block from Portobello's Restaurant, Billy's By The Bay and Kontokosta Vineyard. Close to Village shops, bars, restaurants, farmstands, winery, galleries, museums and more. The well-equipped house is so inviting, just unpack and unwind! (Southold Town Permit #1012. Per Southold town, maximum occupancy: 5).