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Stylishly Renovated Ranch with Saltwater Pool! Bright, white, and move-in ready—this renovated ranch offers the modern coastal look every buyer is searching for. The open, airy layout features a cozy living room, spacious dining area, and an eat-in kitchen with white cabinetry, brushed gold hardware, and new flooring. The living room features large windows overlooking the backyard and gorgeous pool, filling the home with natural light. The dining room has great indoor outdoor flow, perfect for entertaining. The property includes two bedrooms, one full bath, a full unfinished basement, and an attached 1.5 car garage. Upgrades include super high efficient CAC with air cleaner (2023,) freshly painted interiors (2024,) light-toned flooring (2025), and updated window treatments throughout (2025). Exterior improvements include a 18x36 saltwater vinyl pool with stadium steps which has: propane heat, integrated pool lighting system, automatic cover and mesh winter cover (2023). Bluestone pavers surrounding the pool and connecting to a covered patio, and upgraded landscaping for a clean, modern finish (2023). Covered patio is 25x12 and is the perfect place to enjoy your morning coffee or evening cocktail and relax. Ideally located near both Southold Village and historic Greenport, the property offers the best of both worlds. Wineries, local farms, and farm-to-table dining are just moments away, while boating enthusiasts will appreciate nearby marinas. Serene beaches like Town Beach and Goose Beach are just moments away. A turnkey opportunity for those seeking a year-round home, weekend retreat, or investment property on the North Fork. Furnishings may be available for separate purchase.

2 Beds ⋅ 1 Baths ⋅ 934620 MLS

Stylishly Renovated Ranch with Saltwater Pool! Bright, white, and move-in ready—this renovated ranch offers the modern coastal look every buyer is searching for. The open, airy layout features a cozy living room, spacious dining area, and an eat-in kitchen with white cabinetry, brushed gold hardware, and new flooring. The living room features large windows overlooking the backyard and gorgeous pool, filling the home with natural light. The dining room has great indoor outdoor flow, perfect for entertaining. The property includes two bedrooms, one full bath, a full unfinished basement, and an attached 1.5 car garage. Upgrades include super high efficient CAC with air cleaner (2023,) freshly painted interiors (2024,) light-toned flooring (2025), and updated window treatments throughout (2025). Exterior improvements include a 18x36 saltwater vinyl pool with stadium steps which has: propane heat, integrated pool lighting system, automatic cover and mesh winter cover (2023). Bluestone pavers surrounding the pool and connecting to a covered patio, and upgraded landscaping for a clean, modern finish (2023). Covered patio is 25x12 and is the perfect place to enjoy your morning coffee or evening cocktail and relax. Ideally located near both Southold Village and historic Greenport, the property offers the best of both worlds. Wineries, local farms, and farm-to-table dining are just moments away, while boating enthusiasts will appreciate nearby marinas. Serene beaches like Town Beach and Goose Beach are just moments away. A turnkey opportunity for those seeking a year-round home, weekend retreat, or investment property on the North Fork. Furnishings may be available for separate purchase.

920 Pine Neck Road, Southold

$869,000

Move right in and start enjoying the North Fork lifestyle! This updated 3-bedroom, 2-bath home blends comfort and style with wood floors and abundant natural light. Recent renovations added central air, a modern kitchen with stainless steel appliances with large island, and beautifully updated bathrooms. Outside, you will enjoy a landscaped backyard complete with a pergola, a waterfall and room for a pool. Set on Glenn Road, with West Creek just across the street and a marina just down the block this location is perfect for those who enjoy the water. Close to Southold’s beaches, shops, and restaurants, this home offers a move-in-ready breath of fresh air.

3 Beds ⋅ 2 Baths ⋅ 886341 MLS

Move right in and start enjoying the North Fork lifestyle! This updated 3-bedroom, 2-bath home blends comfort and style with wood floors and abundant natural light. Recent renovations added central air, a modern kitchen with stainless steel appliances with large island, and beautifully updated bathrooms. Outside, you will enjoy a landscaped backyard complete with a pergola, a waterfall and room for a pool. Set on Glenn Road, with West Creek just across the street and a marina just down the block this location is perfect for those who enjoy the water. Close to Southold’s beaches, shops, and restaurants, this home offers a move-in-ready breath of fresh air.

625 Glenn Road, Southold

$865,000

Lovely light-filled 3-bedroom 3 bath inland end-unit in The Cove – a small hidden gem of a waterfront community nestled in the heart of the North Fork. There are boat slips for your boat with easy access to the beautiful Peconic Bay, boat racks for your paddleboard/kayak, a gunite in-ground pool, and combination tennis/pickleball court – both of which were just resurfaced this year! The airy open concept living room and dining room share a wood burning fireplace and there is a balcony off the living room. The kitchen has granite counters and sliding glass doors to the deck and the backyard. Also on the first floor is a spacious primary bedroom suite with sliders to the deck and a large ensuite bathroom. The 2nd level has two more generous bedrooms, a library/media room, and full bath. There is storage galore in the finished basement with a separate laundry area, and a one-car garage. The entire community is presently in the process of being re-shingled with handsome grey Hardi-shingles and white trim. Beaches, wineries, farms, breweries, golf, & hamlet shopping, dining, and transportation just moments away! A perfect, maintenance-free Retreat!

3 Beds ⋅ 3 Baths ⋅ 862942 MLS

Lovely light-filled 3-bedroom 3 bath inland end-unit in The Cove – a small hidden gem of a waterfront community nestled in the heart of the North Fork. There are boat slips for your boat with easy access to the beautiful Peconic Bay, boat racks for your paddleboard/kayak, a gunite in-ground pool, and combination tennis/pickleball court – both of which were just resurfaced this year! The airy open concept living room and dining room share a wood burning fireplace and there is a balcony off the living room. The kitchen has granite counters and sliding glass doors to the deck and the backyard. Also on the first floor is a spacious primary bedroom suite with sliders to the deck and a large ensuite bathroom. The 2nd level has two more generous bedrooms, a library/media room, and full bath. There is storage galore in the finished basement with a separate laundry area, and a one-car garage. The entire community is presently in the process of being re-shingled with handsome grey Hardi-shingles and white trim. Beaches, wineries, farms, breweries, golf, & hamlet shopping, dining, and transportation just moments away! A perfect, maintenance-free Retreat!

500 Meadow Court Unit #28, Southold

$864,000

Delightful 3-bedroom, 2-bath ranch style home with attached 2 car garage offers the perfect blend of coastal charm and village convenience. Just minutes to Goose Creek Beach, village shops and restaurants, Southold schools, and convenient transportation, this home invites you to live the North Fork lifestyle to the fullest. The spacious rear patio overlooking a shy half acre --- perfect for entertaining, gardening or even adding a pool. Whether you're seeking a weekend retreat or a full-time haven, this home delivers charm, comfort and room to grow! Some photos are virtually staged. First showing at Open House on Saturday 10/4/25 from 11am-1pm.

3 Beds ⋅ 2 Baths ⋅ 915131 MLS

Delightful 3-bedroom, 2-bath ranch style home with attached 2 car garage offers the perfect blend of coastal charm and village convenience. Just minutes to Goose Creek Beach, village shops and restaurants, Southold schools, and convenient transportation, this home invites you to live the North Fork lifestyle to the fullest. The spacious rear patio overlooking a shy half acre --- perfect for entertaining, gardening or even adding a pool. Whether you're seeking a weekend retreat or a full-time haven, this home delivers charm, comfort and room to grow! Some photos are virtually staged. First showing at Open House on Saturday 10/4/25 from 11am-1pm.

440 Jernick Lane, Southold

$850,000

This bright and airy 3-bedroom, 2-bathroom home on Southold's charming Hyatt Road offers a perfect blend of open and closed living spaces. With numerous windows and skylights, the home seamlessly integrates with the surrounding mature landscaping. Each bedroom boasts vaulted ceilings and picturesque views of the park-like setting. The Primary has a large ensuite bath. Conveniently located just 0.3 miles from McCabes Beach and a short drive to both downtown Southold and Greenport, this property provides both tranquility and easy access to local amenities. Full basement and attached 1 car garage.

3 Beds ⋅ 2 Baths ⋅ 843099 MLS

This bright and airy 3-bedroom, 2-bathroom home on Southold's charming Hyatt Road offers a perfect blend of open and closed living spaces. With numerous windows and skylights, the home seamlessly integrates with the surrounding mature landscaping. Each bedroom boasts vaulted ceilings and picturesque views of the park-like setting. The Primary has a large ensuite bath. Conveniently located just 0.3 miles from McCabes Beach and a short drive to both downtown Southold and Greenport, this property provides both tranquility and easy access to local amenities. Full basement and attached 1 car garage.

2955 Hyatt Road, Southold

$815,000

Lovingly maintained 3-bedroom, 2-bath home in the heart of Southold. Step inside this charming residence and be welcomed by a light-filled living room with a wood-burning fireplace. The primary bedroom features an ensuite full bath, while two guest bedrooms share an additional full bath. The renovated kitchen offers ample space to host family and friends, flowing seamlessly into a spacious dining room. From here, step out onto the back deck and patio, which leads directly to the pool area, perfect for summer entertaining. Set on a generous 0.34-acre corner lot, the property is enhanced by mature trees and shrubs, creating ample privacy and seclusion. Ideally located, both Goose Creek Beach and Southold Hamlet’s vibrant downtown are less than a mile from your front door. Don't miss the opportunity to visit this cozy and calming North Fork home.

3 Beds ⋅ 2 Baths ⋅ 907756 MLS

Lovingly maintained 3-bedroom, 2-bath home in the heart of Southold. Step inside this charming residence and be welcomed by a light-filled living room with a wood-burning fireplace. The primary bedroom features an ensuite full bath, while two guest bedrooms share an additional full bath. The renovated kitchen offers ample space to host family and friends, flowing seamlessly into a spacious dining room. From here, step out onto the back deck and patio, which leads directly to the pool area, perfect for summer entertaining. Set on a generous 0.34-acre corner lot, the property is enhanced by mature trees and shrubs, creating ample privacy and seclusion. Ideally located, both Goose Creek Beach and Southold Hamlet’s vibrant downtown are less than a mile from your front door. Don't miss the opportunity to visit this cozy and calming North Fork home.

2575 Oaklawn Avenue, Southold

$800,000

Nestled on .49 acre corner lot, this 2-bedroom, 1-bath home offers a thoughtful blend of comfort, charm, and modern updates. The heart of the home is the large kitchen, beautifully redone in 2018 with granite countertops, stainless steel appliances, a pantry, coffee bar, wine fridge, and a peninsula with seating that makes entertaining effortless. An open dining area flows naturally into the living room, where a wood-burning stove creates a warm and welcoming atmosphere. A spacious den provides endless possibilities, currently set up as a sunlit lounge—but you may envision a home office, playroom, gym, or future guest room conversion. Additional conveniences include first-floor laundry, propane gas cooking, oak wood floors throughout, and a full unfinished basement for storage or expansion. This home has been meticulously maintained and upgraded, offering peace of mind with a brand-new HVAC system (2024), roof, siding, windows, and Trex deck (2020). A detached 2-car garage and full-house generator add to its appeal. Low taxes! Ideally located near both Southold Village and historic Greenport, the property offers the best of both worlds. Wineries, local farms, and farm-to-table dining are just moments away, while boating enthusiasts will appreciate nearby marinas. Serene beaches like Town Beach and Goose Beach are close by. Rental permit in place. Furniture potentially included with sale, if desired. Whether you’re seeking a year-round residence, a North Fork retreat, or investment opportunity — this move-in ready gem invites you to settle in and start enjoying the North Fork lifestyle right away!

2 Beds ⋅ 1 Baths ⋅ 916546 MLS

Nestled on .49 acre corner lot, this 2-bedroom, 1-bath home offers a thoughtful blend of comfort, charm, and modern updates. The heart of the home is the large kitchen, beautifully redone in 2018 with granite countertops, stainless steel appliances, a pantry, coffee bar, wine fridge, and a peninsula with seating that makes entertaining effortless. An open dining area flows naturally into the living room, where a wood-burning stove creates a warm and welcoming atmosphere. A spacious den provides endless possibilities, currently set up as a sunlit lounge—but you may envision a home office, playroom, gym, or future guest room conversion. Additional conveniences include first-floor laundry, propane gas cooking, oak wood floors throughout, and a full unfinished basement for storage or expansion. This home has been meticulously maintained and upgraded, offering peace of mind with a brand-new HVAC system (2024), roof, siding, windows, and Trex deck (2020). A detached 2-car garage and full-house generator add to its appeal. Low taxes! Ideally located near both Southold Village and historic Greenport, the property offers the best of both worlds. Wineries, local farms, and farm-to-table dining are just moments away, while boating enthusiasts will appreciate nearby marinas. Serene beaches like Town Beach and Goose Beach are close by. Rental permit in place. Furniture potentially included with sale, if desired. Whether you’re seeking a year-round residence, a North Fork retreat, or investment opportunity — this move-in ready gem invites you to settle in and start enjoying the North Fork lifestyle right away!

80 Clearview Avenue W, Southold

$791,000

This charming brick house offers ample space and with a few updates it would be a perfect forever home. Its nestled in a serene neighborhood with an eat in kitchen , formal dining room, spacious living room with wood burning fireplace, 3 spacious bedrooms and 2 full bathrooms with convenience of laundry room on first floor. 2 car garage with potential loft area. It is surrounded with mature landscaping with beautiful views.

3 Beds ⋅ 2 Baths ⋅ 826980 MLS

This charming brick house offers ample space and with a few updates it would be a perfect forever home. Its nestled in a serene neighborhood with an eat in kitchen , formal dining room, spacious living room with wood burning fireplace, 3 spacious bedrooms and 2 full bathrooms with convenience of laundry room on first floor. 2 car garage with potential loft area. It is surrounded with mature landscaping with beautiful views.

155 Shepard Drive, Southold

$785,000

A charming four-bedroom, two-bath, one-level home with a touch of nostalgic appeal. This home boasts wood flooring and an attached two-car garage, nestled on a level corner lot. The primary bedroom offers the convenience of an attached full bathroom. The house, while in need of a little TLC, presents an exciting opportunity - a blank canvas ready for your personal touch. The full basement adds to the potential of this home. The property is part of the Southold Park District, providing special beach privileges at Founders Landing Park and the Wharf House. Additionally, a chance to participate in the town lottery for a discounted boat slip is an enticing extra. Located just a stone's throw from the picturesque beaches, the vibrant Southold Village with its array of shops and restaurants, and the region's renowned wineries, this property is an opportunity not to be missed. Experience the unique blend of tranquility and convenience that 280 Clearview Avenue offers. Don't wait - this home is waiting for you to make it your own.

4 Beds ⋅ 2 Baths ⋅ 936259 MLS

A charming four-bedroom, two-bath, one-level home with a touch of nostalgic appeal. This home boasts wood flooring and an attached two-car garage, nestled on a level corner lot. The primary bedroom offers the convenience of an attached full bathroom. The house, while in need of a little TLC, presents an exciting opportunity - a blank canvas ready for your personal touch. The full basement adds to the potential of this home. The property is part of the Southold Park District, providing special beach privileges at Founders Landing Park and the Wharf House. Additionally, a chance to participate in the town lottery for a discounted boat slip is an enticing extra. Located just a stone's throw from the picturesque beaches, the vibrant Southold Village with its array of shops and restaurants, and the region's renowned wineries, this property is an opportunity not to be missed. Experience the unique blend of tranquility and convenience that 280 Clearview Avenue offers. Don't wait - this home is waiting for you to make it your own.

280 Clearview Avenue, Southold

$780,000

Luxury Builders Dream Lot and Ideal for a Land Buyer Who Wants to Build Their Dream Home in a World-Class Location. Building Permit Already Intact for 4,000+ Sq. Ft. Ultra-Luxury Residence. Seller Has Furnished Model of Identical Residence on Display at 2820 Stanley Road, Mattituck. A Shovel-Ready Building Lot, Perched Within a Waterview Cul-de-sac Development and Adjacent to Pastoral Farmland, Represents A Truly Rare and Outstanding Opportunity. Values are Extremely Strong in this Development, As Each Building Lot Includes a Protective Covenant Mandating Residences to Exceed 3,000 sq. ft. of Living Space and Feature All-Natural Exterior Materials.

911864 MLS

Luxury Builders Dream Lot and Ideal for a Land Buyer Who Wants to Build Their Dream Home in a World-Class Location. Building Permit Already Intact for 4,000+ Sq. Ft. Ultra-Luxury Residence. Seller Has Furnished Model of Identical Residence on Display at 2820 Stanley Road, Mattituck. A Shovel-Ready Building Lot, Perched Within a Waterview Cul-de-sac Development and Adjacent to Pastoral Farmland, Represents A Truly Rare and Outstanding Opportunity. Values are Extremely Strong in this Development, As Each Building Lot Includes a Protective Covenant Mandating Residences to Exceed 3,000 sq. ft. of Living Space and Feature All-Natural Exterior Materials.

390 Wildberry Lane, Southold

$775,000

Build your North Fork dream in the heart of Southold. This exceptional 0.96-acre parcel is nestled among mature trees and surrounded by the scenic beauty of farmland and nature. This peaceful setting with easy access to Long Island Sound beaches, with breathtaking sunsets, acclaimed wineries, farm stands, marinas, and charming village amenities. Buyer is responsible for verifying all zoning, permits, and permitted uses with the Town of Southold. Artist Rendering- For Illustrative Purposes Only. Images are artistic interpretations and should not be relied upon as representations of existing conditions, future improvements, or development potential. All land use, zoning, and building approvals are subject to review by the Town of Southold and applicable agencies.

1031247 MLS

Build your North Fork dream in the heart of Southold. This exceptional 0.96-acre parcel is nestled among mature trees and surrounded by the scenic beauty of farmland and nature. This peaceful setting with easy access to Long Island Sound beaches, with breathtaking sunsets, acclaimed wineries, farm stands, marinas, and charming village amenities. Buyer is responsible for verifying all zoning, permits, and permitted uses with the Town of Southold. Artist Rendering- For Illustrative Purposes Only. Images are artistic interpretations and should not be relied upon as representations of existing conditions, future improvements, or development potential. All land use, zoning, and building approvals are subject to review by the Town of Southold and applicable agencies.

13260 Soundview Avenue, Southold

$775,000

Welcome to your dream North Fork escape! A storybook coastal cottage tucked away on a quiet street, just a few blocks from Founder’s Landing Park, the beach, and the Wharf House, This 2-bedroom, 2-bathroom cedar shake home is full of charm, comfort, and convenience. Whether you're looking for a full-time home, a weekend getaway, or a stylish rental property, this one has it all— and then some. From the moment you arrive, the home gives off that warm, welcoming vibe that just says relax. Inside, you’re greeted by a sun-filled open floor plan, with a living and dining area that’s perfect for entertaining or cozy nights in. The eat-in kitchen features a gas range (great for cooking up your farmers market finds), plenty of cabinet space, and views of the backyard. There’s also a full bathroom and laundry area conveniently located on the main floor. Upstairs, you’ll find two spacious bedrooms—one with a queen-sized bed and the other with twin beds plus a futon, offering lots of flexibility for guests or a home office setup. A second full bathroom rounds out the upper level, making it easy to host friends and family comfortably. The private, fully fenced backyard is a peaceful little oasis that feels like it was made for lazy summer afternoons and laid-back evenings. Plenty of space for dining and lounging, a firepit for s’mores under the stars, an outdoor shower to rinse the sand off and a BBQ area for grilling local seafood and veggies. There's even a red barn outbuilding that adds charm and offers plenty of storage space. There’s ample off-street parking, a garage, and beautiful landscaping that keeps things low-maintenance but lush. And the location? Truly unbeatable. You're right in the heart of Southold Village, with easy access to all the best the North Fork has to offer. After the beach, grab coffee from North Fork Roasting Co., dinner at Southold Social, or head out for wine tasting at one of the many world-class vineyards just minutes away. You’re also close to Einstein Square, Greenport Village, farm stands, parks, and convenient public transportation via the LIRR or Hampton Jitney. This turnkey Southold cottage is a rare find that brings together comfort, character, and an unbeatable North Fork location. Whether you're looking for a weekend escape, a full-time move, or an easy rental property, this sweet cottage is move-in ready and full of charm. Come live the laid-back, wine-sipping, beach- life you’ve been dreaming of!

2 Beds ⋅ 2 Baths ⋅ 922643 MLS

Welcome to your dream North Fork escape! A storybook coastal cottage tucked away on a quiet street, just a few blocks from Founder’s Landing Park, the beach, and the Wharf House, This 2-bedroom, 2-bathroom cedar shake home is full of charm, comfort, and convenience. Whether you're looking for a full-time home, a weekend getaway, or a stylish rental property, this one has it all— and then some. From the moment you arrive, the home gives off that warm, welcoming vibe that just says relax. Inside, you’re greeted by a sun-filled open floor plan, with a living and dining area that’s perfect for entertaining or cozy nights in. The eat-in kitchen features a gas range (great for cooking up your farmers market finds), plenty of cabinet space, and views of the backyard. There’s also a full bathroom and laundry area conveniently located on the main floor. Upstairs, you’ll find two spacious bedrooms—one with a queen-sized bed and the other with twin beds plus a futon, offering lots of flexibility for guests or a home office setup. A second full bathroom rounds out the upper level, making it easy to host friends and family comfortably. The private, fully fenced backyard is a peaceful little oasis that feels like it was made for lazy summer afternoons and laid-back evenings. Plenty of space for dining and lounging, a firepit for s’mores under the stars, an outdoor shower to rinse the sand off and a BBQ area for grilling local seafood and veggies. There's even a red barn outbuilding that adds charm and offers plenty of storage space. There’s ample off-street parking, a garage, and beautiful landscaping that keeps things low-maintenance but lush. And the location? Truly unbeatable. You're right in the heart of Southold Village, with easy access to all the best the North Fork has to offer. After the beach, grab coffee from North Fork Roasting Co., dinner at Southold Social, or head out for wine tasting at one of the many world-class vineyards just minutes away. You’re also close to Einstein Square, Greenport Village, farm stands, parks, and convenient public transportation via the LIRR or Hampton Jitney. This turnkey Southold cottage is a rare find that brings together comfort, character, and an unbeatable North Fork location. Whether you're looking for a weekend escape, a full-time move, or an easy rental property, this sweet cottage is move-in ready and full of charm. Come live the laid-back, wine-sipping, beach- life you’ve been dreaming of!

150 Hobart Road, Southold

$756,000

Summer Cottage in Southold – Just steps from the Long Islands Sound. Experience quintessential North Fork living in this completely renovated charmer featuring 3-bedrooms, and 1-bathroom perfectly positioned just steps from the beach and minutes drive away from other local beaches. Offering unrivaled access to stunning sunsets and the coastal lifestyle, the cottage features warm wood-beamed ceilings, hardwood floors, and a bright, open living area that flows effortlessly into the kitchen and dining nook — ideal for relaxed summer living and entertaining. While modest in size, this home’s true value lies in its unbeatable location and lifestyle appeal — a prime investment for those seeking a serene seasonal retreat or an exclusive North Fork address.

3 Beds ⋅ 1 Baths ⋅ 860794 MLS

Summer Cottage in Southold – Just steps from the Long Islands Sound. Experience quintessential North Fork living in this completely renovated charmer featuring 3-bedrooms, and 1-bathroom perfectly positioned just steps from the beach and minutes drive away from other local beaches. Offering unrivaled access to stunning sunsets and the coastal lifestyle, the cottage features warm wood-beamed ceilings, hardwood floors, and a bright, open living area that flows effortlessly into the kitchen and dining nook — ideal for relaxed summer living and entertaining. While modest in size, this home’s true value lies in its unbeatable location and lifestyle appeal — a prime investment for those seeking a serene seasonal retreat or an exclusive North Fork address.

150 Goldin Lane, Southold

$750,750

Welcome to 350 Brigantine Drive, a charming Southold retreat set in the peaceful waterfront-community of Harbor Lights where you can enjoy a private beach that overlooks the Peconic bay and Shelter Island. This home offers comfortable living, an inviting layout, and access to all the natural beauty and coastal lifestyle that make Southold so desirable. The main level features a bright and open living area with plenty of natural light, a functional kitchen, and a seamless flow ideal for everyday living or weekend escapes. 3 bedrooms and 2 bathrooms provide comfort and privacy, while the home’s overall layout lends itself to both full-time residency and seasonal enjoyment. Images in this listing have been virtually staged. Outdoors, the property offers a spacious yard perfect for entertaining, gardening, or simply relaxing in the quiet surroundings. Located in a sought-after neighborhood known for its tranquility and proximity to beaches, boating, vineyards, farm stands, and local dining, this home places you at the heart of everything the North Fork has to offer. Whether you’re seeking a year-round residence, a vacation getaway, or a home with long-term potential, 350 Brigantine Drive delivers an exceptional opportunity in one of Southold’s most beloved communities.

3 Beds ⋅ 2 Baths ⋅ 956754 MLS

Welcome to 350 Brigantine Drive, a charming Southold retreat set in the peaceful waterfront-community of Harbor Lights where you can enjoy a private beach that overlooks the Peconic bay and Shelter Island. This home offers comfortable living, an inviting layout, and access to all the natural beauty and coastal lifestyle that make Southold so desirable. The main level features a bright and open living area with plenty of natural light, a functional kitchen, and a seamless flow ideal for everyday living or weekend escapes. 3 bedrooms and 2 bathrooms provide comfort and privacy, while the home’s overall layout lends itself to both full-time residency and seasonal enjoyment. Images in this listing have been virtually staged. Outdoors, the property offers a spacious yard perfect for entertaining, gardening, or simply relaxing in the quiet surroundings. Located in a sought-after neighborhood known for its tranquility and proximity to beaches, boating, vineyards, farm stands, and local dining, this home places you at the heart of everything the North Fork has to offer. Whether you’re seeking a year-round residence, a vacation getaway, or a home with long-term potential, 350 Brigantine Drive delivers an exceptional opportunity in one of Southold’s most beloved communities.

350 Brigantine Drive, Southold

$750,000

Residential/Hamlet Business Opportunity Beautifully restored and updated Colonial Path House located in the heart of wine country. The front facade of the house has been restored to clapboard siding and cedar shake. The original rooms on the first floor include a parlor with wood burning fireplace, an adjacent dining room, farm kitchen and full bath/laundry room. Antique wide plank floors throughout. The second floor has 2 bedrooms, large storage closet, and full bath with an antique soaker tub. A new addition in 2007 compliments the old part of the house while modernizing the space with an ensuite bedroom, living room, a year-round sunroom, and working fireplace with a hand carved mantle from a Victorian Mansion. The kitchen has been updated with built in cabinets, a farm sink, a Bosch dishwasher and Viking stove. A bluestone patio is directly off the primary bedroom. A successful and popular bed and breakfast was operated in this new addition. An accessory cottage is perfect for your studio or office. Access to Founders Landing Beach.

3 Beds ⋅ 3 Baths ⋅ 856377 MLS

Residential/Hamlet Business Opportunity Beautifully restored and updated Colonial Path House located in the heart of wine country. The front facade of the house has been restored to clapboard siding and cedar shake. The original rooms on the first floor include a parlor with wood burning fireplace, an adjacent dining room, farm kitchen and full bath/laundry room. Antique wide plank floors throughout. The second floor has 2 bedrooms, large storage closet, and full bath with an antique soaker tub. A new addition in 2007 compliments the old part of the house while modernizing the space with an ensuite bedroom, living room, a year-round sunroom, and working fireplace with a hand carved mantle from a Victorian Mansion. The kitchen has been updated with built in cabinets, a farm sink, a Bosch dishwasher and Viking stove. A bluestone patio is directly off the primary bedroom. A successful and popular bed and breakfast was operated in this new addition. An accessory cottage is perfect for your studio or office. Access to Founders Landing Beach.

57020 Route 25, Southold

$740,000

A great business and/or investment opportunity awaits! Once a popular Southold holistic/chiropractic office with separate living quarters and then a childcare facility and apartment, this adaptable split-level property is awaiting its next creativite live-in business venture! Located on a beautiful .83 acre, this property fronts the high visibility County Road 48/North Road and backs up to scenic preserved farmland. The ground floor has a large waiting room, offices with sinks, and a half bath. The 2nd floor is a spacious 2-bedroom 1 bath rental apartment that could also be used as the business owner's home. Its Limited Business Zoning offers many opportunities including professional office, retail operation, custom workshop, garden shop/nursery, restaurant, dog and cat care facility, repair shop, etc.

1016880 MLS

A great business and/or investment opportunity awaits! Once a popular Southold holistic/chiropractic office with separate living quarters and then a childcare facility and apartment, this adaptable split-level property is awaiting its next creativite live-in business venture! Located on a beautiful .83 acre, this property fronts the high visibility County Road 48/North Road and backs up to scenic preserved farmland. The ground floor has a large waiting room, offices with sinks, and a half bath. The 2nd floor is a spacious 2-bedroom 1 bath rental apartment that could also be used as the business owner's home. Its Limited Business Zoning offers many opportunities including professional office, retail operation, custom workshop, garden shop/nursery, restaurant, dog and cat care facility, repair shop, etc.

44600 County Road 48, Southold

$740,000

A great business and/or investment opportunity awaits! Once a popular Southold holistic/chiropractic office with separate living quarters and then a childcare facility and apartment, this adaptable split-level property is awaiting its next creativite live-in business venture! Located on a beautiful .83 acre, this property fronts the high visibility County Road 48/North Road and backs up to scenic preserved farmland. The ground floor has a large waiting room, offices with sinks, and a half bath. The 2nd floor is a spacious 2-bedroom 1 bath rental apartment that could also be used as the business owner's home. Its Limited Business Zoning offers many opportunities including professional office, retail operation, custom workshop, garden shop/nursery, restaurant, dog and cat care facility, repair shop, etc.

2 Beds ⋅ 2 Baths ⋅ 1015353 MLS

A great business and/or investment opportunity awaits! Once a popular Southold holistic/chiropractic office with separate living quarters and then a childcare facility and apartment, this adaptable split-level property is awaiting its next creativite live-in business venture! Located on a beautiful .83 acre, this property fronts the high visibility County Road 48/North Road and backs up to scenic preserved farmland. The ground floor has a large waiting room, offices with sinks, and a half bath. The 2nd floor is a spacious 2-bedroom 1 bath rental apartment that could also be used as the business owner's home. Its Limited Business Zoning offers many opportunities including professional office, retail operation, custom workshop, garden shop/nursery, restaurant, dog and cat care facility, repair shop, etc.

44600 County Road 48, Southold

$740,000

Welcome to one of the best locations in Southold! Laughing Water Community with their own private beach and access to their island on Corey Creek water, with two marinas, a boat ramp for all boat lovers, and rights to two stunning private park districts (South Harbor and Founders Park) known for their pristine beach and clubhouse overlooking Shelter Island. This lovely bright and sunny move in ready ranch offers open concept living with beautiful oak floor, living room/ dining room/ kitchen, 3 bedrooms (one is currently used as a den with fireplace), large bath with Jacuzzi tub, inviting sunscreen porch, two single garages (front and back) to conveniently store your Kayak, paddle boat and beach chairs. This home is located on a corner lot with plenty of room for a pool and is a stone's throw from award winning winery Croteaux Vineyards, a short ride to the brewery, farmstands, antique shop, and the best restaurants in town. This will be your perfect vacation getaway or your forever home in our proud North Fork.

3 Beds ⋅ 1 Baths ⋅ 912925 MLS

Welcome to one of the best locations in Southold! Laughing Water Community with their own private beach and access to their island on Corey Creek water, with two marinas, a boat ramp for all boat lovers, and rights to two stunning private park districts (South Harbor and Founders Park) known for their pristine beach and clubhouse overlooking Shelter Island. This lovely bright and sunny move in ready ranch offers open concept living with beautiful oak floor, living room/ dining room/ kitchen, 3 bedrooms (one is currently used as a den with fireplace), large bath with Jacuzzi tub, inviting sunscreen porch, two single garages (front and back) to conveniently store your Kayak, paddle boat and beach chairs. This home is located on a corner lot with plenty of room for a pool and is a stone's throw from award winning winery Croteaux Vineyards, a short ride to the brewery, farmstands, antique shop, and the best restaurants in town. This will be your perfect vacation getaway or your forever home in our proud North Fork.

1040 Nakomis Road, Southold

$733,000

Great office space with apartment! The office has 5+ exam rooms, large waiting area and 2 half baths. The 1 bedroom, 1 bath apartment has a large kitchen, loft area and large deck. The property sits on one acre and has ample parking. The office and apartment must be owner occupied, or the entire structure could be converted to all living space as well as keeping the apartment. Many uses for this property - medical property, nursery school, place or worship and many more!

1 Beds ⋅ 4 Baths ⋅ 889540 MLS

Great office space with apartment! The office has 5+ exam rooms, large waiting area and 2 half baths. The 1 bedroom, 1 bath apartment has a large kitchen, loft area and large deck. The property sits on one acre and has ample parking. The office and apartment must be owner occupied, or the entire structure could be converted to all living space as well as keeping the apartment. Many uses for this property - medical property, nursery school, place or worship and many more!

Southold

$720,000

Southold- Get ready to kick off your shoes this summer... Kenneys Beach is waiting for you. This two bedroom, one bath ranch home has been lovingly maintained. An easy, open floor plan consists of a living room, eat-in-kitchen, and separate dining room/den. Slider to a large patio perfect for entertaining and family get-togethers. Two comfortable bedrooms. One bath with a tub/shower combo. Wood floors throughout. A level .29 acre parcel features a pebble fire pit seating area, lovely plantings, gardens, and a manicured lawn. Outdoor shower. Partial basement. Situated between Kenney and McCabe's Long Island Sound beaches. This home is an exceptional value, ready to use as is, or as the starting point for your North Fork year-round or vacation home. Everything is right here...beaches, restaurants, golf, farm stands, wineries and shopping. An excellent opportunity to enter the North Fork market.

2 Beds ⋅ 1 Baths ⋅ 947455 MLS

Southold- Get ready to kick off your shoes this summer... Kenneys Beach is waiting for you. This two bedroom, one bath ranch home has been lovingly maintained. An easy, open floor plan consists of a living room, eat-in-kitchen, and separate dining room/den. Slider to a large patio perfect for entertaining and family get-togethers. Two comfortable bedrooms. One bath with a tub/shower combo. Wood floors throughout. A level .29 acre parcel features a pebble fire pit seating area, lovely plantings, gardens, and a manicured lawn. Outdoor shower. Partial basement. Situated between Kenney and McCabe's Long Island Sound beaches. This home is an exceptional value, ready to use as is, or as the starting point for your North Fork year-round or vacation home. Everything is right here...beaches, restaurants, golf, farm stands, wineries and shopping. An excellent opportunity to enter the North Fork market.

340 Pine Road, Southold

$718,000

Picture this: you’ve been walking through homes that are either way too much house… or feel like a shoebox with a mortgage. Then you walk into this one and it just clicks, not too big, not too small, and it actually makes sense for real life. It’s a two-bedroom layout that works, and the bathroom is basically begging for a remodel. The pink tile had its moment, but I’d happily retire it and put in something that feels like my style. The kind of update that instantly makes the whole house feel fresher without turning your life into a six-month construction zone. What I really love is how you get two different “hangout spaces” Up front, there’s a sunroom that keeps you connected to the neighborhood, coffee in the morning, wave to the walkers, feel like you’re actually part of a community. Then out back you’ve got a deck where you can disappear a little, because it overlooks the woods and the yard is fenced in, The kitchen is the same vibe: totally functional, but also a clear opportunity. Can use it comfortably right now, and then renovate when ready, and the fact that it could be expanded makes it feel like a smart move. And the neighborhood perk? This is the kind you can’t renovate into a house later: the park and beach at the end of the street. In the summer you get that breeze off the water, that easy “flip-flops and go” lifestyle. It’s the simple stuff that ends up being the best stuff.

2 Beds ⋅ 1 Baths ⋅ 961780 MLS

Picture this: you’ve been walking through homes that are either way too much house… or feel like a shoebox with a mortgage. Then you walk into this one and it just clicks, not too big, not too small, and it actually makes sense for real life. It’s a two-bedroom layout that works, and the bathroom is basically begging for a remodel. The pink tile had its moment, but I’d happily retire it and put in something that feels like my style. The kind of update that instantly makes the whole house feel fresher without turning your life into a six-month construction zone. What I really love is how you get two different “hangout spaces” Up front, there’s a sunroom that keeps you connected to the neighborhood, coffee in the morning, wave to the walkers, feel like you’re actually part of a community. Then out back you’ve got a deck where you can disappear a little, because it overlooks the woods and the yard is fenced in, The kitchen is the same vibe: totally functional, but also a clear opportunity. Can use it comfortably right now, and then renovate when ready, and the fact that it could be expanded makes it feel like a smart move. And the neighborhood perk? This is the kind you can’t renovate into a house later: the park and beach at the end of the street. In the summer you get that breeze off the water, that easy “flip-flops and go” lifestyle. It’s the simple stuff that ends up being the best stuff.

1000 Gin Lane, Southold

$690,000

Perfect opportunity for 1st time buyers, downsizers, or investors! This original-style 3-bedroom, 1-bath ranch, perfectly situated just steps from a beautiful Goose Creek beach in a highly desirable Southold location. With a spacious backyard and room for a pool, this home offers a fantastic opportunity to make it your own. Enjoy the convenience of single-level living, featuring a primary bedroom and an easy-flow layout that makes everyday life a breeze. Located within the Southold Park District, you’ll have access to stunning parks, pristine beaches, and all the charm of the North Fork. A little work will transform this home into something truly special—don’t miss your chance!!!!

3 Beds ⋅ 1 Baths ⋅ 839087 MLS

Perfect opportunity for 1st time buyers, downsizers, or investors! This original-style 3-bedroom, 1-bath ranch, perfectly situated just steps from a beautiful Goose Creek beach in a highly desirable Southold location. With a spacious backyard and room for a pool, this home offers a fantastic opportunity to make it your own. Enjoy the convenience of single-level living, featuring a primary bedroom and an easy-flow layout that makes everyday life a breeze. Located within the Southold Park District, you’ll have access to stunning parks, pristine beaches, and all the charm of the North Fork. A little work will transform this home into something truly special—don’t miss your chance!!!!

570 N North Bayview Road, Southold

$685,000

Discover a beautifully renovated unit featuring ceramic tile throughout and two modern marble full bathrooms, including a primary ensuite with walk-in custom closets. Enjoy a spacious open living room with a cozy fireplace and sliders leading to a patio, seamlessly connected to the dining area and large eat-in kitchen. Convenient main floor washer and dryer. The property boasts a very large, clean, and dry full-size basement. Nestled in a 55+ community with lush greenery, an in-ground pool, and a clubhouse perfect for socializing. Ideally located just a short distance from town, train, shopping, the library, and the beach.

2 Beds ⋅ 2 Baths ⋅ 919707 MLS

Discover a beautifully renovated unit featuring ceramic tile throughout and two modern marble full bathrooms, including a primary ensuite with walk-in custom closets. Enjoy a spacious open living room with a cozy fireplace and sliders leading to a patio, seamlessly connected to the dining area and large eat-in kitchen. Convenient main floor washer and dryer. The property boasts a very large, clean, and dry full-size basement. Nestled in a 55+ community with lush greenery, an in-ground pool, and a clubhouse perfect for socializing. Ideally located just a short distance from town, train, shopping, the library, and the beach.

2555 Youngs Avenue Unit #14A, Southold

$665,000

Location, Location, Location! Nestled in the heart of Southold, this home is in a beautiful neighborhood and in close proximity to a cozy restaurant, the Custer Institute Observatory for gazing at the stars and a charming farm stand just around the corner. The property is delightful, especially the backyard with views of nearby horses grazing. This 3 bedroom, 1 bath home offers the ease of one floor living and is a blank canvas waiting for your personal touch. Hardwood floors throughout and an enclosed sunroom too. Best of all, the big ticket items have been taken care of: Roof is just 3 years young, the boiler was replaced last year and the hot water tank is brand new! With a little TLC, you can create an inviting space that reflects your style. The one car garage and full basement offer additional space for your needs. At this price, it won't last!

3 Beds ⋅ 1 Baths ⋅ 904653 MLS

Location, Location, Location! Nestled in the heart of Southold, this home is in a beautiful neighborhood and in close proximity to a cozy restaurant, the Custer Institute Observatory for gazing at the stars and a charming farm stand just around the corner. The property is delightful, especially the backyard with views of nearby horses grazing. This 3 bedroom, 1 bath home offers the ease of one floor living and is a blank canvas waiting for your personal touch. Hardwood floors throughout and an enclosed sunroom too. Best of all, the big ticket items have been taken care of: Roof is just 3 years young, the boiler was replaced last year and the hot water tank is brand new! With a little TLC, you can create an inviting space that reflects your style. The one car garage and full basement offer additional space for your needs. At this price, it won't last!

205 Grange Road, Southold

$650,000

Welcome to the North Fork. This pristine Ranch home features 3 Bedrooms 1 bath Updated Kitchen with dining area and access to large deck and cozy fire pit, full semi finished basement with laundry room and storage plus 1 1/2 car garage. Imagine your days wine tasting, strolling the hamlet of Southold, a short drive to Greenport with top notch Restaurants and Shops or just relaxing on the beaches close proximity to the Peconic Bay and the Long Island Sound. Year round living awaits.

3 Beds ⋅ 1 Baths ⋅ 856542 MLS

Welcome to the North Fork. This pristine Ranch home features 3 Bedrooms 1 bath Updated Kitchen with dining area and access to large deck and cozy fire pit, full semi finished basement with laundry room and storage plus 1 1/2 car garage. Imagine your days wine tasting, strolling the hamlet of Southold, a short drive to Greenport with top notch Restaurants and Shops or just relaxing on the beaches close proximity to the Peconic Bay and the Long Island Sound. Year round living awaits.

900 Cedar Drive, Southold

$645,000

Just 950 feet from the beloved Kenney's Beach this charming 3 bed room, one bath beach cottage offers a rare opportunity to create your dream retreat in one of the most desirable locations on the North Fork. This property is brimming with potential both inside and out. Enjoy sun filled days by the beach and stop by Little Fish for sunset cocktails at night. Inside, you’ll find a cozy living room, a full kitchen, and a sun-drenched year-round sunroom, perfect for morning coffee or quiet reading. Outside, peaceful garden spaces offer room for outdoor dining ready to be enjoyed and enhanced. A rustic “she shed” and additional storage spaces provide creative possibilities, while the natural, sanctuary-like setting makes this home beautiful in every season. This home's true magic lies in its unbeatable location and the potential to make it uniquely yours.

3 Beds ⋅ 1 Baths ⋅ 899619 MLS

Just 950 feet from the beloved Kenney's Beach this charming 3 bed room, one bath beach cottage offers a rare opportunity to create your dream retreat in one of the most desirable locations on the North Fork. This property is brimming with potential both inside and out. Enjoy sun filled days by the beach and stop by Little Fish for sunset cocktails at night. Inside, you’ll find a cozy living room, a full kitchen, and a sun-drenched year-round sunroom, perfect for morning coffee or quiet reading. Outside, peaceful garden spaces offer room for outdoor dining ready to be enjoyed and enhanced. A rustic “she shed” and additional storage spaces provide creative possibilities, while the natural, sanctuary-like setting makes this home beautiful in every season. This home's true magic lies in its unbeatable location and the potential to make it uniquely yours.

335 Dogwood Lane, Southold

$620,000

Welcome to 265 Hummel Ave in Southold, a charming two-bedroom, one-bathroom gem that embodies the perfect balance of comfort and potential. This property is a blank canvas for your imagination, boasting a full attic that presents an exciting opportunity for expansion, allowing you to customize the loft space to your unique needs and taste. The home is situated in a vibrant community that thrives on connectivity and convenience. Just moments from your doorstep, you’ll find the local bus and train station, making your commute or weekend trips a breeze. Additionally, this location places you in close proximity to a variety of local shops, offering everything from everyday essentials to unique finds. Schedule your showing today and do not run the risk of missing out on this fantastic opportunity!

2 Beds ⋅ 1 Baths ⋅ 942515 MLS

Welcome to 265 Hummel Ave in Southold, a charming two-bedroom, one-bathroom gem that embodies the perfect balance of comfort and potential. This property is a blank canvas for your imagination, boasting a full attic that presents an exciting opportunity for expansion, allowing you to customize the loft space to your unique needs and taste. The home is situated in a vibrant community that thrives on connectivity and convenience. Just moments from your doorstep, you’ll find the local bus and train station, making your commute or weekend trips a breeze. Additionally, this location places you in close proximity to a variety of local shops, offering everything from everyday essentials to unique finds. Schedule your showing today and do not run the risk of missing out on this fantastic opportunity!

265 Hummel Avenue, Southold

$605,000

Gorgeous, light, bright, and airy, this immaculate 2-bedroom, 2-bath condominium is located in the highly desirable Founders Village 55+ community. Featuring soaring vaulted ceilings, an eat-in kitchen, spacious living and dining areas, and an inviting open layout, this home is designed for comfortable, low-maintenance living. The primary suite offers a private bath and generous closet space, while a full basement provides exceptional storage and endless possibilities. Enjoy beautifully maintained grounds, a community clubhouse, and pool, all just minutes from Southold Village, wineries, farm stands, beaches, shopping, and transportation. A wonderful opportunity to enjoy the best of the North Fork lifestyle.

2 Beds ⋅ 2 Baths ⋅ 1006443 MLS

Gorgeous, light, bright, and airy, this immaculate 2-bedroom, 2-bath condominium is located in the highly desirable Founders Village 55+ community. Featuring soaring vaulted ceilings, an eat-in kitchen, spacious living and dining areas, and an inviting open layout, this home is designed for comfortable, low-maintenance living. The primary suite offers a private bath and generous closet space, while a full basement provides exceptional storage and endless possibilities. Enjoy beautifully maintained grounds, a community clubhouse, and pool, all just minutes from Southold Village, wineries, farm stands, beaches, shopping, and transportation. A wonderful opportunity to enjoy the best of the North Fork lifestyle.

2555 Youngs Avenue Unit #1D, Southold

$600,000

Ranch Style Home. This Home Features 2 Bedrooms, Full Bath, Dining Area, Eat In Kitchen & 2 Car Garage. Centrally Located To All. Don't Miss This Opportunity!

2 Beds ⋅ 1 Baths ⋅ 1007215 MLS

Ranch Style Home. This Home Features 2 Bedrooms, Full Bath, Dining Area, Eat In Kitchen & 2 Car Garage. Centrally Located To All. Don't Miss This Opportunity!

6900 Main Bayview Road, Southold

$600,000

Wonderful opportunity in prime location to build your dream home on this bright and private corner lot of 0.55 acre in the desirable community of Southold. This land has partial water view and access to ramp at the end of the road to Goose Creek for boating, kayaking, and fishing. And yes, it is only a few minutes from town, restaurants, farmstands, wineries, antique shops, and more.

996413 MLS

Wonderful opportunity in prime location to build your dream home on this bright and private corner lot of 0.55 acre in the desirable community of Southold. This land has partial water view and access to ramp at the end of the road to Goose Creek for boating, kayaking, and fishing. And yes, it is only a few minutes from town, restaurants, farmstands, wineries, antique shops, and more.

105 Mailer Court, Southold