Southold Classified Ad Listings

65 Prospect St. 65 Prospect Street. 4 Bedrooms. 8 Bathroom. 3852 ft

117 Fox Hollow Ln. An exceptional six bedroom home on a quiet street just moments from Meadow Lane ocean beaches. Spacious entry foyer, formal living and dining rooms, media room, an island kitchen and first floor guest bedroom with en-suite bath. The main second floor offers a primary bedroom with en-suite bath and two additional bedrooms. The private second floor guest wing features two spaci...

4 Bennett Dr. Spend your summer at 4 Bennett Drive in East Quogue, where spacious interiors and expansive outdoor living set the stage for a relaxing Hamptons getaway. Set on a private acre on a quiet cul-de-sac, this four-bedroom, three-bath home welcomes you with a wraparound front porch, perfect for morning coffee. Inside, a kitchen with stainless steel appliances and granite countertops, a ...

1340 Ships Dr. Welcome to the effortless elegance of North Fork living at 1340 Ships Drive, a stunning Southold new construction where every inch has been masterfully planned and designed. This pristine retreat welcomes you with an expansive open floor plan and gorgeous wood floors that flow throughout the entire residence. At the heart of the home lies a true gourmet kitchen, centered around a...

32 Old Fish Cove Rd. Recently renovated to perfection, this Cape style residence is the perfect place to call home for the summer! Features include a classic covered front porch with two swings, plus 2,000 square feet of glamorous living space. The ground floor boasts a double height living room, open eat-in kitchen with island, dining room, guest bedroom and full bathroom. Upstairs, the primar...

85 Michael Dr. Flexible Lease Terms Available-price varies based on seasonality and terms (3, 6, 9, or 12 Months). This fully furnished rental at 85 Michael Drive offers a seamless move-in experience with a spacious and versatile layout designed for modern comfort. Set on an acre with a serene natural setting, the main floor of this single-level residence features a bright entrance hall leading...

22 Knoll Rd. Views from practically all rooms in this stylish home elevated above Shinnecock Bay with views as far as the Ocean passed Meadow Lane! Open floor plan with great room, kitchen and dining area with large stone fireplace. Phenomenal first floor master suite with the best views in town from the soaking tub. Second floor has 4 guest bedrooms with vaulted ceilings and sunning decks, Low...

345 Colonial Road. Property for Rent in Southold, NY for $20,000 with 3 bedrooms and 3 full baths, 1 half bath. This 2,724 square foot property was built in 1975 on a lot size of 0.37.. Tucked away on a private setting in a peaceful North Fork neighborhood just minutes from Corey Creek, Croteaux Vineyards and Greenport Brewery, this exceptional colonial offers the perfect backdrop for an unforg...

3 Bayview Rd. Some homes have a lot. This one just has IT! Extremely unique and wonderfully private, this stylish waterfront cottage mini-compound is the perfect winter-to-spring retreat. Two shockingly chic, shingled boutique bungalows sit directly on 50' of beachfront in Upper Sag Harbor Cove, with wraparound water views from nearly every room. The compound is professionally designed and impe...

6 Jean Dr. ** seller requests offers by Tuesday 7/14 at noon** Welcome to this beautifully maintained and extensively updated home offering over 3,500 square feet of exceptional living space in a sought-after cul-de-sac neighborhood. Featuring 4 bedrooms, 3 full baths, and 1 half bath, this move-in-ready residence combines generous room sizes, a flexible floor plan, and major recent improvement...

2015 Prime Time Crusader Lite 28RL, 2015 Prime Time Crusader Lite 28RL 31' 10" Fifth Wheel. 2 Slide Outs, Awning, Sleeps 6, A/C Unit. Experience the perfect blend of residential comfort, thoughtful design, and fifth-wheel convenience with this 2015 Prime Time Crusader Lite 28RL. With sleeping accommodations for up to 6, this beautifully designed rear-living fifth wheel delivers an inviting atmo...

570 Hampton Rd Apt 30. Southampton Village Fully Renovated Condo. 3 Bedrooms. 2 Bathroom. 1830 ft

8 Valley Rd. Available November through May 2027 for $8,475/month or for 1 month. Newly renovated and beautifully furnished Sag Harbor home offering 5 bedrooms and 5.5 bathrooms, including four bedrooms with private en-suite baths.Thoughtfully spread across three levels, the home offers plenty of space and privacy for family and guests. The main level features a spacious great room, an open kit...

635 Strohson Rd. Cutchogue-Spend summer in this quintessential North Fork cottage. Immaculate, beautifully furnished and well equipped home with everything you need for a comfortable stay. Wonderful location just steps to water access for boating, kayaking, paddle boarding, and fishing. Beaches, shopping, restaurants farm stands, fish market, wineries and breweries just minutes away. Available ...

305 N Main St. $75,000 August 1-31st $145,000 July 1st thru Labor Day $80,000 August 1-31st $75,000 July 1-31st $50,000 June 1-30th $200,000 Memorial Day to Labor Day Stunning 6 bedroom 4.5 bath two hundred year old farmhouse and separate cottage with a rich history. This home has being lovingly restored throughout - mixing refined antiques, period details and modern amenities for maximum style...

951 Old Clinton Rd Unit 18. Welcome to Redwood Common, a desirable condo community of just 20 meticulously maintained units ideally located close to downtown, beaches, shopping, restaurants, and all the Connecticut shoreline has to offer. This beautifully maintained townhouse offers a flexible floor plan with hardwood floors throughout, elegant crown moldings, and an abundance of natural light....

50 Old Main Rd. Available Two weeks: August 13-August 27 2027. In Quogue Village, 50 Old Main is a vacation dream-this 4 bed, 4 1/2 bath home features generous open spaces for entertaining, a heated pool set in an endless lawn, and a separate 2 story studio cottage. The first floor features an open plan with a bright entry foyer, sunken living room, and a huge cook's kitchen meant for prepping ...

11 Kitteridge Hill Road. Single Family Home for sale in Old Saybrook, CT for $679,000 with 3 bedrooms and 2 full baths, 1 half bath. This 2,755 square foot home was built in 1978 on a lot size of 1.26.. Discover the charm and comfort of this beautifully maintained Cape, ideally situated on a quiet cul-de-sac off School House Road in one of Old Saybrook's desirable locations. Offering over 2,700...

66 Oak Ave. Classic Farm house colonial sits directly on the waterfront! The home embodies peace and tranquility with a nod to simpler times when nature was the forefront of relaxation. Enjoy your private beach and yard and take in those glorious sunsets that Madison is known for. Enjoy a classic floor plan with a galley style kitchen, dining room, living room and a sunny closed in back porch t...

65 Tyler Drive. Single Family Home for sale in Riverhead, NY for $995,000 with 3 bedrooms and 2 full baths, 1 half bath. This 2,992 square foot home was built in 2004 on a lot size of 0.18.. The Estates at Olde Vine What if the next chapter of your life felt like being on vacation every day? Imagine starting your morning with coffee on the front porch, spending the afternoon on the golf course,...