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Cape Cod Style Retreat in the Heart of Southold This Southold gem delivers the perfect blend of peace, privacy, and proximity to all the North Fork has to offer. Enjoy Blocks to McCabes Beach, Kenny’s Beach, Horton Point Lighthouse, vineyards, farm stands, and charming local shops—all just minutes away. Originally built in 1989, this home has been thoughtfully updated and expanded with a brand-new addition in 2024 and a modern kitchen completed in 2016. Offering 3 bedrooms easily convert to 4 spacious bedrooms and 3 full baths, the layout is both functional and flexible for your lifestyle needs. Additional features include: Oversized climate-controlled detached 2-car garage (2023) Oversized climate-controlled attached garage New electric panel (2024) and 500-gallon buried propane tank (2023) Two new HVAC units (2025) and whole-house 20kW generator (2024) Whole-house water filtration system (2023) Oil heat with a newer tank Andersen windows, Trex decking, roll-up rear awning (2023), and fire pit for outdoor enjoyment Fenced rear yard, walk-out basement with 2 egress windows, and underground sprinkler system (2024) 2-car port for additional covered parking Don’t miss this rare opportunity to own a beautifully maintained, move-in-ready home that sits on 2.17 acres in one of Southold’s most desirable locations. Come experience your slice of paradise on the North Fork! If you're looking for space, updates, and a great backyard setup, this one checks all the boxes. Come take a look — you’ll love what you see!

3 Beds ⋅ 3 Baths ⋅ 907526 MLS

Cape Cod Style Retreat in the Heart of Southold This Southold gem delivers the perfect blend of peace, privacy, and proximity to all the North Fork has to offer. Enjoy Blocks to McCabes Beach, Kenny’s Beach, Horton Point Lighthouse, vineyards, farm stands, and charming local shops—all just minutes away. Originally built in 1989, this home has been thoughtfully updated and expanded with a brand-new addition in 2024 and a modern kitchen completed in 2016. Offering 3 bedrooms easily convert to 4 spacious bedrooms and 3 full baths, the layout is both functional and flexible for your lifestyle needs. Additional features include: Oversized climate-controlled detached 2-car garage (2023) Oversized climate-controlled attached garage New electric panel (2024) and 500-gallon buried propane tank (2023) Two new HVAC units (2025) and whole-house 20kW generator (2024) Whole-house water filtration system (2023) Oil heat with a newer tank Andersen windows, Trex decking, roll-up rear awning (2023), and fire pit for outdoor enjoyment Fenced rear yard, walk-out basement with 2 egress windows, and underground sprinkler system (2024) 2-car port for additional covered parking Don’t miss this rare opportunity to own a beautifully maintained, move-in-ready home that sits on 2.17 acres in one of Southold’s most desirable locations. Come experience your slice of paradise on the North Fork! If you're looking for space, updates, and a great backyard setup, this one checks all the boxes. Come take a look — you’ll love what you see!

3520 Old North Road, Southold

$1,300,000

North Fork Coastal Living With Sunset & Water Views Enjoy breathtaking sunsets and water views from any of the three private balconies of this beautiful North Fork retreat. Designed for comfort and relaxed elegance, this residence features a dynamic open floor plan that seamlessly connects the living room, dining, and kitchen areas leading to outdoor balconies. The granite kitchen is perfect for entertaining, opening to a bright living room with a fireplace and a cozy den ideal for year-round gatherings. The first-floor primary suite offers convenience and privacy, while upstairs you’ll find two additional bedrooms, each with its own balcony overlooking the Long Island Sound. The fully finished walk-out basement extends the living space with direct access to the patio and backyard, ideal for outdoor dining or relaxing in the coastal breeze. A detached two-car garage includes a bonus room for extra storage above, offering generous space for a studio, office and many other possibilities. Perfectly located near McCabe’s and Kenney’s Beaches, local vineyards, the lighthouse, and North Fork’s favorite restaurants, this home captures the essence of seaside living — where every day feels like a getaway.

3 Beds ⋅ 4 Baths ⋅ 920310 MLS

North Fork Coastal Living With Sunset & Water Views Enjoy breathtaking sunsets and water views from any of the three private balconies of this beautiful North Fork retreat. Designed for comfort and relaxed elegance, this residence features a dynamic open floor plan that seamlessly connects the living room, dining, and kitchen areas leading to outdoor balconies. The granite kitchen is perfect for entertaining, opening to a bright living room with a fireplace and a cozy den ideal for year-round gatherings. The first-floor primary suite offers convenience and privacy, while upstairs you’ll find two additional bedrooms, each with its own balcony overlooking the Long Island Sound. The fully finished walk-out basement extends the living space with direct access to the patio and backyard, ideal for outdoor dining or relaxing in the coastal breeze. A detached two-car garage includes a bonus room for extra storage above, offering generous space for a studio, office and many other possibilities. Perfectly located near McCabe’s and Kenney’s Beaches, local vineyards, the lighthouse, and North Fork’s favorite restaurants, this home captures the essence of seaside living — where every day feels like a getaway.

12250 Soundview Avenue, Southold

$1,250,000

Grab your beach chair and your towel and get ready for summer! This quintessential Long Island Sound beachfront cottage offers water views from every room plus spectacular, and unobstructed western sunsets. Turn-key and move-in ready, this 2-bedroom, 1-bath gem perfectly blends classic seaside charm with modern comfort, featuring a renovated kitchen, and bath. Situated on .25-acre, this waterfront property has plenty of room for enjoying outdoor entertaining. Just step outside, breathe in the salt air, and start living the North Fork beach life.

2 Beds ⋅ 1 Baths ⋅ 1015770 MLS

Grab your beach chair and your towel and get ready for summer! This quintessential Long Island Sound beachfront cottage offers water views from every room plus spectacular, and unobstructed western sunsets. Turn-key and move-in ready, this 2-bedroom, 1-bath gem perfectly blends classic seaside charm with modern comfort, featuring a renovated kitchen, and bath. Situated on .25-acre, this waterfront property has plenty of room for enjoying outdoor entertaining. Just step outside, breathe in the salt air, and start living the North Fork beach life.

56055 County Road 48, Southold

$1,250,000

Southold Waterfront, Goose Creek Lane Association- Exceptional waterfront location with serene Goose Creek views. Gorgeous sunsets. Shy half acre landscaped property located on a peaceful country lane. Easy access to Goose Creek Beach and the Southold Yacht Club. Traditional style home with 3 bedrooms, 3 baths and expansive water views. The house features an open floor plan: Spacious Kitchen with granite counters, Living Room with a wood burning fireplace, and Dining Area with French Doors opening to a large waterside wrap deck. Family room perfect for informal entertaining, a mud room and full bath complete the 1st floor. On the second floor, there is a waterside primary en-suite bedroom with broad views over the Creek. Two more gracious guest bedrooms and a full bath. This home is light and bright. Rooms have many windows to capture the views. Bay windows in the primary bedroom and living room. Ceiling fans in the bedrooms. A fabulous location near all amenities: restaurants, vineyards, farm stands, shopping, marinas, and beaches. For year round or seasonal living, this property is an outstanding value as is, with many upside possibilities in a setting that cannot be replicated.

3 Beds ⋅ 3 Baths ⋅ 907530 MLS

Southold Waterfront, Goose Creek Lane Association- Exceptional waterfront location with serene Goose Creek views. Gorgeous sunsets. Shy half acre landscaped property located on a peaceful country lane. Easy access to Goose Creek Beach and the Southold Yacht Club. Traditional style home with 3 bedrooms, 3 baths and expansive water views. The house features an open floor plan: Spacious Kitchen with granite counters, Living Room with a wood burning fireplace, and Dining Area with French Doors opening to a large waterside wrap deck. Family room perfect for informal entertaining, a mud room and full bath complete the 1st floor. On the second floor, there is a waterside primary en-suite bedroom with broad views over the Creek. Two more gracious guest bedrooms and a full bath. This home is light and bright. Rooms have many windows to capture the views. Bay windows in the primary bedroom and living room. Ceiling fans in the bedrooms. A fabulous location near all amenities: restaurants, vineyards, farm stands, shopping, marinas, and beaches. For year round or seasonal living, this property is an outstanding value as is, with many upside possibilities in a setting that cannot be replicated.

800 Goose Creek Lane, Southold

$1,250,000

Nestled in the heart of Southold’s coveted North Fork, 1465 Ackerly Pond Lane offers a rare opportunity to own a custom home on over 2.5 acres of serene, private land. This single-family property is surrounded by natural beauty and tucked away on a quiet lane, making it ideal for those seeking peace and space just minutes from the village, vineyards, and beaches. Home features a large gourmet kitchen, 4 bedrooms, 2.5 baths, hardwood floors, mudroom, oversized 3 car garage, large, 11 foot deep basement with 3 egress windows ready to be finished. The lot is zoned for residential use and offers ample room for a custom pool, small vineyard, gardens, tennis, pickleball, etc. or garden retreat. Whether you're envisioning a weekend escape or a full-time residence, this substantial property provides the canvas to bring your dream home to life in one of Long Island’s most charming coastal communities. Brand New Boiler/Heating system.

4 Beds ⋅ 3 Baths ⋅ 856096 MLS

Nestled in the heart of Southold’s coveted North Fork, 1465 Ackerly Pond Lane offers a rare opportunity to own a custom home on over 2.5 acres of serene, private land. This single-family property is surrounded by natural beauty and tucked away on a quiet lane, making it ideal for those seeking peace and space just minutes from the village, vineyards, and beaches. Home features a large gourmet kitchen, 4 bedrooms, 2.5 baths, hardwood floors, mudroom, oversized 3 car garage, large, 11 foot deep basement with 3 egress windows ready to be finished. The lot is zoned for residential use and offers ample room for a custom pool, small vineyard, gardens, tennis, pickleball, etc. or garden retreat. Whether you're envisioning a weekend escape or a full-time residence, this substantial property provides the canvas to bring your dream home to life in one of Long Island’s most charming coastal communities. Brand New Boiler/Heating system.

1465 Ackerly Pond Lane, Southold

$1,249,000

Southold, North Fork – Private Bayfront Community Living Discover effortless, upscale living in the coveted Angel Shores bayfront community, complete with private association access to a pristine sugar-sand beach. Set on a beautifully landscaped, ultra-private lot backing to over 20 acres of protected preserve land—with only one immediate neighboring home—this exceptional 2,300 sq ft contemporary ranch offers rare privacy, serenity, and sophistication in one of the North Fork’s most desirable locations. The expansive property also provides ample space for an in-ground pool or additional outdoor amenities. Designed for true ease of one-floor living, the home features soaring vaulted ceilings that enhance the light-filled living and dining areas, creating an inviting space for both everyday comfort and entertaining. Step outside to approximately 1,500 sq ft of expansive decking—perfect for hosting gatherings or enjoying quiet moments surrounded by mature landscaping and natural beauty. The thoughtfully designed layout offers ideal separation and privacy, featuring 2.5 baths: a private owner’s suite with en-suite full bath, generous walk-in closet, and dedicated office area or 4th bedroom/nursery; two guest bedrooms situated on the opposite side of the home with a shared full bath; plus a convenient half bath located near the den. The spacious kitchen with breakfast area flows seamlessly into the living spaces, while the cozy den with fireplace adds warmth and charm. Extensive upgrades elevate both convenience and peace of mind, including a whole-house automatic generator, new furnace, new central air conditioning, new washer and dryer, and a new oil tank. An oversized buried propane tank offers flexibility for future gas appliances, pool heating, or additional enhancements. A high-tech security system adds another layer of comfort. The full, unfinished basement provides abundant storage with potential for additional living space and features a two-car garage with separate driveway access, ideal for service entry—while the circular driveway ensures a grand and practical welcome for visitors. Enjoy close proximity to additional beaches, marinas, renowned restaurants, boutique shopping, and the celebrated North Fork Wine Trail. Whether you’re seeking a full-time residence or a refined weekend retreat, this home delivers the very best of North Fork living in a peaceful, private setting.

3 Beds ⋅ 3 Baths ⋅ 993409 MLS

Southold, North Fork – Private Bayfront Community Living Discover effortless, upscale living in the coveted Angel Shores bayfront community, complete with private association access to a pristine sugar-sand beach. Set on a beautifully landscaped, ultra-private lot backing to over 20 acres of protected preserve land—with only one immediate neighboring home—this exceptional 2,300 sq ft contemporary ranch offers rare privacy, serenity, and sophistication in one of the North Fork’s most desirable locations. The expansive property also provides ample space for an in-ground pool or additional outdoor amenities. Designed for true ease of one-floor living, the home features soaring vaulted ceilings that enhance the light-filled living and dining areas, creating an inviting space for both everyday comfort and entertaining. Step outside to approximately 1,500 sq ft of expansive decking—perfect for hosting gatherings or enjoying quiet moments surrounded by mature landscaping and natural beauty. The thoughtfully designed layout offers ideal separation and privacy, featuring 2.5 baths: a private owner’s suite with en-suite full bath, generous walk-in closet, and dedicated office area or 4th bedroom/nursery; two guest bedrooms situated on the opposite side of the home with a shared full bath; plus a convenient half bath located near the den. The spacious kitchen with breakfast area flows seamlessly into the living spaces, while the cozy den with fireplace adds warmth and charm. Extensive upgrades elevate both convenience and peace of mind, including a whole-house automatic generator, new furnace, new central air conditioning, new washer and dryer, and a new oil tank. An oversized buried propane tank offers flexibility for future gas appliances, pool heating, or additional enhancements. A high-tech security system adds another layer of comfort. The full, unfinished basement provides abundant storage with potential for additional living space and features a two-car garage with separate driveway access, ideal for service entry—while the circular driveway ensures a grand and practical welcome for visitors. Enjoy close proximity to additional beaches, marinas, renowned restaurants, boutique shopping, and the celebrated North Fork Wine Trail. Whether you’re seeking a full-time residence or a refined weekend retreat, this home delivers the very best of North Fork living in a peaceful, private setting.

650 The Esplanade, Southold

$1,239,000

Tucked away on a beautifully landscaped property, this 2022 built 4 bedroom, 3.5 bath residence offers the perfect blend of modern construction, thoughtful design, and effortless North Fork charm. From the moment you arrive, the inviting front porch, complete with a classic swing, sets the tone for relaxed living. Inside, the home is thoughtfully designed with a seamless flow, anchored by a stunning, light-filled chef’s kitchen that truly serves as the heart of the home. Featuring a large center island with seating, quartz countertops, custom cabinetry, stainless steel appliances, and designer pendant lighting, the space is both functional and refined. Expansive windows bring in natural light and tranquil views, while the kitchen opens effortlessly into a beautifully appointed dining area that is bright and welcoming and leads directly to the outdoor deck, creating a seamless indoor-outdoor lifestyle. This home offers a rare and highly desirable layout with primary bedrooms on both the first and second floors, each with en-suite bathrooms. The second-floor primary suite is particularly impressive, featuring a walk-in closet and a spacious bath complete with a large shower and double vanity sinks. Throughout the home, crown molding and 9-foot ceilings on the first floor enhance the sense of scale and craftsmanship, while an open-to-above foyer adds volume and an airy, inviting feel. All bedrooms are generously sized and feature large windows, filling each space with natural light. Guest and additional bathrooms are well-appointed with oversized tubs and showers, offering comfort and convenience throughout. Additional living space is found in the cozy, full glass sunroom, which opens to a large, spacious deck overlooking a completely private backyard. Designed for both relaxation and entertaining, the outdoor space includes a large 8-person hot tub (just 2 years old), lush landscaping, and a charming garden room—perfect as a lounge, studio, or quiet retreat. The entire property is fenced and includes a dedicated dog run area. A partially finished basement provides excellent flexible space with a walk-in closet, ideal for a home gym or media room. And the location? Truly exceptional. Just moments from Kenny’s Beach, renowned for its expansive beach and stunning sunsets. A rare opportunity to own a nearly new home with exceptional features, flexible living space, and an unbeatable location—where every detail has been thoughtfully considered.

4 Beds ⋅ 4 Baths ⋅ 988709 MLS

Tucked away on a beautifully landscaped property, this 2022 built 4 bedroom, 3.5 bath residence offers the perfect blend of modern construction, thoughtful design, and effortless North Fork charm. From the moment you arrive, the inviting front porch, complete with a classic swing, sets the tone for relaxed living. Inside, the home is thoughtfully designed with a seamless flow, anchored by a stunning, light-filled chef’s kitchen that truly serves as the heart of the home. Featuring a large center island with seating, quartz countertops, custom cabinetry, stainless steel appliances, and designer pendant lighting, the space is both functional and refined. Expansive windows bring in natural light and tranquil views, while the kitchen opens effortlessly into a beautifully appointed dining area that is bright and welcoming and leads directly to the outdoor deck, creating a seamless indoor-outdoor lifestyle. This home offers a rare and highly desirable layout with primary bedrooms on both the first and second floors, each with en-suite bathrooms. The second-floor primary suite is particularly impressive, featuring a walk-in closet and a spacious bath complete with a large shower and double vanity sinks. Throughout the home, crown molding and 9-foot ceilings on the first floor enhance the sense of scale and craftsmanship, while an open-to-above foyer adds volume and an airy, inviting feel. All bedrooms are generously sized and feature large windows, filling each space with natural light. Guest and additional bathrooms are well-appointed with oversized tubs and showers, offering comfort and convenience throughout. Additional living space is found in the cozy, full glass sunroom, which opens to a large, spacious deck overlooking a completely private backyard. Designed for both relaxation and entertaining, the outdoor space includes a large 8-person hot tub (just 2 years old), lush landscaping, and a charming garden room—perfect as a lounge, studio, or quiet retreat. The entire property is fenced and includes a dedicated dog run area. A partially finished basement provides excellent flexible space with a walk-in closet, ideal for a home gym or media room. And the location? Truly exceptional. Just moments from Kenny’s Beach, renowned for its expansive beach and stunning sunsets. A rare opportunity to own a nearly new home with exceptional features, flexible living space, and an unbeatable location—where every detail has been thoughtfully considered.

75 Birch Road, Southold

$1,175,000

Embrace refined living in this charming residence nestled in the heart of Southold. Enjoy the expansive .75-acre grounds that provide a sanctuary of tranquility. Situated on a meandering hill, this home offers a serene and private retreat. The modern, chic interior is beautifully designed for comfort and style. The welcoming foyer unfolds into a spacious living room, flowing effortlessly into a quaint kitchen that overlooks the backyard and opens to a large deck, inviting you to enjoy al fresco dining. The formal dining area, with separate access to the yard, transforms entertaining into an elegant affair. The main level features a convenient bedroom with easy access to the living spaces and a full bathroom. Ascend to the upper level, where the grand primary en-suite bedroom awaits, complete with a new spa-appointed bathroom, vaulted ceilings, and new wood flooring, flooded with natural light from a wall of windows. Another spacious en-suite bedroom offers a similar allure, with a new bathroom, new wood flooring, and vaulted ceilings. The lower level, equipped with laundry and a cozy recreation space, offers versatility for a gym, lounge, or home office. There’s ample room for a pool to enhance your outdoor leisure. Within a mile lies the highly sought-after Goose Creek Beach, and you’re perfectly positioned to explore the beautiful amenities of the North Fork—vineyards, Southold Town, fine dining, picturesque beaches, and charming local farm stands.

3 Beds ⋅ 3 Baths ⋅ 888816 MLS

Embrace refined living in this charming residence nestled in the heart of Southold. Enjoy the expansive .75-acre grounds that provide a sanctuary of tranquility. Situated on a meandering hill, this home offers a serene and private retreat. The modern, chic interior is beautifully designed for comfort and style. The welcoming foyer unfolds into a spacious living room, flowing effortlessly into a quaint kitchen that overlooks the backyard and opens to a large deck, inviting you to enjoy al fresco dining. The formal dining area, with separate access to the yard, transforms entertaining into an elegant affair. The main level features a convenient bedroom with easy access to the living spaces and a full bathroom. Ascend to the upper level, where the grand primary en-suite bedroom awaits, complete with a new spa-appointed bathroom, vaulted ceilings, and new wood flooring, flooded with natural light from a wall of windows. Another spacious en-suite bedroom offers a similar allure, with a new bathroom, new wood flooring, and vaulted ceilings. The lower level, equipped with laundry and a cozy recreation space, offers versatility for a gym, lounge, or home office. There’s ample room for a pool to enhance your outdoor leisure. Within a mile lies the highly sought-after Goose Creek Beach, and you’re perfectly positioned to explore the beautiful amenities of the North Fork—vineyards, Southold Town, fine dining, picturesque beaches, and charming local farm stands.

480 N Bayview Road Extension, Southold

$1,175,000

Welcome to this stunning Cape Cod-style home, completely updated in 2025 and thoughtfully designed for modern living with timeless charm. Nestled on a generous half-acre lot, this 4-bedroom, 2.5-bathroom home offers an ideal combination of style, space, and resort-style amenities. Step inside to discover a bright, open floor plan that seamlessly connects the main living areas—perfect for entertaining or everyday living. The updated kitchen features contemporary finishes and flows effortlessly into the dining and living spaces, all bathed in natural light. The first-floor primary suite is a true retreat, offering a spacious en-suite bath and ample closet space. Upstairs, you’ll find three additional bedrooms and a full bath, providing plenty of room for family, guests, or a home office. A convenient half bath is located on the main floor for guests. Step outside and unwind in your private backyard oasis. The heated in-ground saltwater pool is the centerpiece of this serene setting, complemented by a screened lanai—ideal for relaxing or dining al fresco. A two-car garage offers added convenience and storage. With comprehensive updates throughout, this home is truly move-in ready—blending classic Cape Cod charm with the comforts of modern living. Don’t miss your chance to own this beautifully updated home with space, style, and a backyard built for seasonal or year-round enjoyment. Schedule your private tour today!

4 Beds ⋅ 3 Baths ⋅ 857324 MLS

Welcome to this stunning Cape Cod-style home, completely updated in 2025 and thoughtfully designed for modern living with timeless charm. Nestled on a generous half-acre lot, this 4-bedroom, 2.5-bathroom home offers an ideal combination of style, space, and resort-style amenities. Step inside to discover a bright, open floor plan that seamlessly connects the main living areas—perfect for entertaining or everyday living. The updated kitchen features contemporary finishes and flows effortlessly into the dining and living spaces, all bathed in natural light. The first-floor primary suite is a true retreat, offering a spacious en-suite bath and ample closet space. Upstairs, you’ll find three additional bedrooms and a full bath, providing plenty of room for family, guests, or a home office. A convenient half bath is located on the main floor for guests. Step outside and unwind in your private backyard oasis. The heated in-ground saltwater pool is the centerpiece of this serene setting, complemented by a screened lanai—ideal for relaxing or dining al fresco. A two-car garage offers added convenience and storage. With comprehensive updates throughout, this home is truly move-in ready—blending classic Cape Cod charm with the comforts of modern living. Don’t miss your chance to own this beautifully updated home with space, style, and a backyard built for seasonal or year-round enjoyment. Schedule your private tour today!

1475 Oaklawn Avenue, Southold

$1,150,000

Enjoy a beautifully updated home in the desirable Harbor Lights beach community. This home has everything you need to live an amazing North Fork life with hardwood floors throughout, an open floor plan, privacy and an amazing back deck overlooking the backyard. The first floor offers an open floor plan, a beautifully updated eat in kitchen. Enjoy the living room/dining room with a fireplace while overlooking the back patio and backyard. The second floor has 3 bedrooms and a loft. This property is part of the Harbor Lights Community where you can enjoy a private beach that overlooks the peconic bay and shelter island. If you are looking for the perfect North Fork home this is it!

4 Beds ⋅ 4 Baths ⋅ 905803 MLS

Enjoy a beautifully updated home in the desirable Harbor Lights beach community. This home has everything you need to live an amazing North Fork life with hardwood floors throughout, an open floor plan, privacy and an amazing back deck overlooking the backyard. The first floor offers an open floor plan, a beautifully updated eat in kitchen. Enjoy the living room/dining room with a fireplace while overlooking the back patio and backyard. The second floor has 3 bedrooms and a loft. This property is part of the Harbor Lights Community where you can enjoy a private beach that overlooks the peconic bay and shelter island. If you are looking for the perfect North Fork home this is it!

2120 Brigantine Drive, Southold

$1,125,000

Located on a half-acre corner lot in one of Southold’s most sought-after neighborhoods, this 4-bed, 3-bath Cape offers ~2,900sqft of living space and the potential for a pool, subject to variance approval. There’s a spacious eat-in kitchen with stainless steel appliances and a center island, opening to a back patio creating a seamless space for indoor-outdoor entertaining. Additionally, the main level includes a formal dining room anchored by a wood-burning fireplace, a generous living room, a primary ensuite bedroom with a walk-in closet, an additional bedroom that could also serve as an office, and a full bath. Upstairs, two bright bedrooms share a full bathroom, complemented by a convenient hall laundry for everyday ease. A one-car garage and full basement add functional space, and peek-a-boo views of Town Creek provide a subtle coastal touch. While the home is ready for updates, it offers tremendous potential to create a custom North Fork retreat. Just a half mile from Southold hamlet’s shops and restaurants, this property combines convenience, room to grow and an exceptional location.

4 Beds ⋅ 3 Baths ⋅ 966843 MLS

Located on a half-acre corner lot in one of Southold’s most sought-after neighborhoods, this 4-bed, 3-bath Cape offers ~2,900sqft of living space and the potential for a pool, subject to variance approval. There’s a spacious eat-in kitchen with stainless steel appliances and a center island, opening to a back patio creating a seamless space for indoor-outdoor entertaining. Additionally, the main level includes a formal dining room anchored by a wood-burning fireplace, a generous living room, a primary ensuite bedroom with a walk-in closet, an additional bedroom that could also serve as an office, and a full bath. Upstairs, two bright bedrooms share a full bathroom, complemented by a convenient hall laundry for everyday ease. A one-car garage and full basement add functional space, and peek-a-boo views of Town Creek provide a subtle coastal touch. While the home is ready for updates, it offers tremendous potential to create a custom North Fork retreat. Just a half mile from Southold hamlet’s shops and restaurants, this property combines convenience, room to grow and an exceptional location.

1400 Calves Neck Road, Southold

$1,055,000

This expansive residence offers a thoughtfully designed layout with a second-floor primary suite featuring an ensuite bath and a private balcony overlooking the backyard. Two additional guest bedrooms share a generous full bath, providing ample space for hosting company. On the first floor, a light-filled kitchen flows seamlessly into a charming dining nook and a spacious living room centered around a wood-burning stove. Step outside to a private backyard retreat with a large deck for alfresco dining and lounging. The deck leads to another level, complete with a hot tub and grilling area. Beyond, the beautifully landscaped yard is dotted with mature trees and highlighted by a recently added heated saltwater pool with a bluestone surround. The fully updated, legally finished basement provides valuable additional living space, perfect for a media room, gym, or playroom. Just a half mile from a sandy beach and only a 5-minute drive to Greenport and Southold’s commercial districts, where you’ll find some of the East End’s best shops and restaurants.

3 Beds ⋅ 2 Baths ⋅ 907840 MLS

This expansive residence offers a thoughtfully designed layout with a second-floor primary suite featuring an ensuite bath and a private balcony overlooking the backyard. Two additional guest bedrooms share a generous full bath, providing ample space for hosting company. On the first floor, a light-filled kitchen flows seamlessly into a charming dining nook and a spacious living room centered around a wood-burning stove. Step outside to a private backyard retreat with a large deck for alfresco dining and lounging. The deck leads to another level, complete with a hot tub and grilling area. Beyond, the beautifully landscaped yard is dotted with mature trees and highlighted by a recently added heated saltwater pool with a bluestone surround. The fully updated, legally finished basement provides valuable additional living space, perfect for a media room, gym, or playroom. Just a half mile from a sandy beach and only a 5-minute drive to Greenport and Southold’s commercial districts, where you’ll find some of the East End’s best shops and restaurants.

610 Richmond Road, Southold

$1,055,000

Head inside this custom-built, one-owner home nestled in a serene mid-block location, just moments from Southold's finest beaches including Kenney’s and McCabe’s Beach and a few blocks from Little Fish restaurant. This move-in-ready post-modern home boasts an open-to-above entry with gleaming hardwood floors, well-appointed rooms, and a professionally designed kitchen featuring high-end stainless steel appliances, including a built-in wine fridge, a professional-grade Thermador gas range and a Thermador dishwasher. The open-concept layout is perfect for entertaining, with a spacious family room complete with a gas fireplace, seamlessly connecting to the kitchen. Make memories on the large custom built maintenance-free Trex deck, ideal for outdoor gatherings or for simply enjoying amazing sunsets in the serenity of your private backyard with room for an IG pool with site inspection on file with town. Designed for year-round comfort, this home features a two-zone gas heating and two-zone central air systems with oversized Andersen windows that flood the space with natural light. The upper level includes a luxurious primary suite with two walk-in closets and a spa-like bath, along with three additional bedrooms and the convenience of a second-floor laundry room. Additional highlights include an oversized two-car garage and a full basement with 9-foot ceilings, offering ample storage and potential for finishing. Built to green-certified standards with engineered framing for lasting quality, this Southold gem is the perfect blend of comfort, convenience, and luxury.

4 Beds ⋅ 3 Baths ⋅ 832312 MLS

Head inside this custom-built, one-owner home nestled in a serene mid-block location, just moments from Southold's finest beaches including Kenney’s and McCabe’s Beach and a few blocks from Little Fish restaurant. This move-in-ready post-modern home boasts an open-to-above entry with gleaming hardwood floors, well-appointed rooms, and a professionally designed kitchen featuring high-end stainless steel appliances, including a built-in wine fridge, a professional-grade Thermador gas range and a Thermador dishwasher. The open-concept layout is perfect for entertaining, with a spacious family room complete with a gas fireplace, seamlessly connecting to the kitchen. Make memories on the large custom built maintenance-free Trex deck, ideal for outdoor gatherings or for simply enjoying amazing sunsets in the serenity of your private backyard with room for an IG pool with site inspection on file with town. Designed for year-round comfort, this home features a two-zone gas heating and two-zone central air systems with oversized Andersen windows that flood the space with natural light. The upper level includes a luxurious primary suite with two walk-in closets and a spa-like bath, along with three additional bedrooms and the convenience of a second-floor laundry room. Additional highlights include an oversized two-car garage and a full basement with 9-foot ceilings, offering ample storage and potential for finishing. Built to green-certified standards with engineered framing for lasting quality, this Southold gem is the perfect blend of comfort, convenience, and luxury.

380 Hickory Road, Southold

$1,049,000

A must see secluded water front Compound. Rarely do you find two houses on a one acre lot. Main cottage is 3 BR, Eik, FDR,, LR with fireplace, hardwood floors, basement and inviting water side covered porch, second cottage has Primary ensuite and guest Br with second bath, Eik, LR w/Fireplace hardwood floors full basement. Small out building, Additional information: Appearance:Very good

3 Beds ⋅ 2 Baths ⋅ L3487080 MLS

A must see secluded water front Compound. Rarely do you find two houses on a one acre lot. Main cottage is 3 BR, Eik, FDR,, LR with fireplace, hardwood floors, basement and inviting water side covered porch, second cottage has Primary ensuite and guest Br with second bath, Eik, LR w/Fireplace hardwood floors full basement. Small out building, Additional information: Appearance:Very good

633 Pine Neck Road, Southold

$1,025,000

3700 Minnehaha Blvd., Southold, a darling waterfront home nestled in Laughing Waters private beach community. This home is NOT in a flood zone!!! NO flood insurance is required! This house has something for everyone! For boaters, this home is so convenient, with its very own bulkhead and easy access to the Great Peconic Bay, just untie your boat and go! For nature lovers, the views and wildlife sightings are amazing and all from the comfort of your waterside deck – it’ll never get old! For those who just want to relax, the covered front porch is the perfect spot for sipping tea and a good book. The home has recently been painted with a coastal vibe paint pallet and has had brand new hardwood maple flooring installed throughout, making it a blank canvas to move in and make it your own. The full basement with high ceilings provides ample storage. In addition to your very own bulkhead, this charming seaside community features two marinas, a boat ramp, a picnic area, a private sandy bay beach, and kayak storage. This property is a blend of comfort, convenience, and coastal charm. It's a rare opportunity to live in a vibrant community with a strong sense of camaraderie and a love for outdoor activities. Act fast ~ this gem won't last long!

3 Beds ⋅ 2 Baths ⋅ 901091 MLS

3700 Minnehaha Blvd., Southold, a darling waterfront home nestled in Laughing Waters private beach community. This home is NOT in a flood zone!!! NO flood insurance is required! This house has something for everyone! For boaters, this home is so convenient, with its very own bulkhead and easy access to the Great Peconic Bay, just untie your boat and go! For nature lovers, the views and wildlife sightings are amazing and all from the comfort of your waterside deck – it’ll never get old! For those who just want to relax, the covered front porch is the perfect spot for sipping tea and a good book. The home has recently been painted with a coastal vibe paint pallet and has had brand new hardwood maple flooring installed throughout, making it a blank canvas to move in and make it your own. The full basement with high ceilings provides ample storage. In addition to your very own bulkhead, this charming seaside community features two marinas, a boat ramp, a picnic area, a private sandy bay beach, and kayak storage. This property is a blend of comfort, convenience, and coastal charm. It's a rare opportunity to live in a vibrant community with a strong sense of camaraderie and a love for outdoor activities. Act fast ~ this gem won't last long!

3700 Minnehaha Boulevard, Southold

$999,999

The Perfect Beach Bungalow Getaway! An Idyllic Location, With Kenney's Beach Practically At Your Doorstep, This Charming Bungalow Offers Ample Space For Everyone With Five Bedrooms And Two Bathrooms. Relax And Unwind On The Outside Decks Enjoying Morning Coffee, Fresh Sea Breezes And Evening Sunsets Or Warm-up Indoors by the Fireplace. With Its Wonderful Location, Numerous Amenities And Proximity To Local Attractions, This Beach Bungalow Offers Everything You Need For A Memorable Escape. Prepare For A Rejuvenating Retreat At Kenney's Beach!

5 Beds ⋅ 2 Baths ⋅ 804563 MLS

The Perfect Beach Bungalow Getaway! An Idyllic Location, With Kenney's Beach Practically At Your Doorstep, This Charming Bungalow Offers Ample Space For Everyone With Five Bedrooms And Two Bathrooms. Relax And Unwind On The Outside Decks Enjoying Morning Coffee, Fresh Sea Breezes And Evening Sunsets Or Warm-up Indoors by the Fireplace. With Its Wonderful Location, Numerous Amenities And Proximity To Local Attractions, This Beach Bungalow Offers Everything You Need For A Memorable Escape. Prepare For A Rejuvenating Retreat At Kenney's Beach!

65 Lake Drive, Southold

$985,000

****Open House cancelled***Completely renovated raised ranch just moments away from the quaint Southold village, Goose Creek and Founders Beach, local farms, and wineries. All the work has been done for you, just unpack and start living your best life! Great room with gas fireplace, 2-year-old chef's Kitchen with quartz counters and stainless appliances, lower-level guest suite complete with private entrance, 4 bedrooms plus office, new siding, new roof, new den extension, and plenty of room for the pool! Come see this special home in a charming neighborhood where you can finally settle down.

4 Beds ⋅ 2 Baths ⋅ 903668 MLS

****Open House cancelled***Completely renovated raised ranch just moments away from the quaint Southold village, Goose Creek and Founders Beach, local farms, and wineries. All the work has been done for you, just unpack and start living your best life! Great room with gas fireplace, 2-year-old chef's Kitchen with quartz counters and stainless appliances, lower-level guest suite complete with private entrance, 4 bedrooms plus office, new siding, new roof, new den extension, and plenty of room for the pool! Come see this special home in a charming neighborhood where you can finally settle down.

730 Pine Neck Road, Southold

$961,000

Set within the coveted private Terry Waters beach community in Southold, this beautiful three-bedroom, two-bath extended ranch offers relaxed coastal living in an enchanting, private setting. A welcoming entry opens to a spacious living room anchored by a classic brick fireplace, while the thoughtfully designed layout includes a primary bedroom with an ensuite bath, an additional bonus family room ideal for entertaining or everyday living, and a full basement providing ample storage or future potential. Outdoors, a three-season covered patio overlooks the lush, expansive backyard with generous room for a pool, creating the perfect backdrop for summer gatherings or quiet moments near the water.

3 Beds ⋅ 2 Baths ⋅ 976177 MLS

Set within the coveted private Terry Waters beach community in Southold, this beautiful three-bedroom, two-bath extended ranch offers relaxed coastal living in an enchanting, private setting. A welcoming entry opens to a spacious living room anchored by a classic brick fireplace, while the thoughtfully designed layout includes a primary bedroom with an ensuite bath, an additional bonus family room ideal for entertaining or everyday living, and a full basement providing ample storage or future potential. Outdoors, a three-season covered patio overlooks the lush, expansive backyard with generous room for a pool, creating the perfect backdrop for summer gatherings or quiet moments near the water.

340 Rambler Road, Southold

$950,000

Tucked away in the heart of Southold, this adorable 3-bedroom, 2.5-bath ranch offers a rare combination of privacy, small-town charm, spacious living, and tranquil outdoor amenities — including access to dockage (with application from town), with direct bay access and ideally located a few steps from all the conveniences of downtown Southold shopping, dining and the Hampton Jitney. Set on a generous and beautifully landscaped lot, the home welcomes you with a breezy open-concept layout where the living room with fireplace flows seamlessly into the dining area. Large windows invite natural light and peaceful backyard throughout the main living space. Step outside onto a back deck, perfect for entertaining, dining al fresco, or simply enjoying the sights and sounds of nature as well as a beautiful pond view. The expansive backyard offers ample room for gardening, recreation, or even a pool. With three comfortable bedrooms, including a primary suite, hardwood floors, and an easy single-level layout, this home is ideal for year-round living or a weekend getaway. Located in the vibrant village center of Southold — close to beaches, vineyards, farm stands, and local favorites — this property is a rare find that blends convenience, serenity, and North Fork lifestyle at its finest.

3 Beds ⋅ 3 Baths ⋅ 887530 MLS

Tucked away in the heart of Southold, this adorable 3-bedroom, 2.5-bath ranch offers a rare combination of privacy, small-town charm, spacious living, and tranquil outdoor amenities — including access to dockage (with application from town), with direct bay access and ideally located a few steps from all the conveniences of downtown Southold shopping, dining and the Hampton Jitney. Set on a generous and beautifully landscaped lot, the home welcomes you with a breezy open-concept layout where the living room with fireplace flows seamlessly into the dining area. Large windows invite natural light and peaceful backyard throughout the main living space. Step outside onto a back deck, perfect for entertaining, dining al fresco, or simply enjoying the sights and sounds of nature as well as a beautiful pond view. The expansive backyard offers ample room for gardening, recreation, or even a pool. With three comfortable bedrooms, including a primary suite, hardwood floors, and an easy single-level layout, this home is ideal for year-round living or a weekend getaway. Located in the vibrant village center of Southold — close to beaches, vineyards, farm stands, and local favorites — this property is a rare find that blends convenience, serenity, and North Fork lifestyle at its finest.

720 Mechanic Street, Southold

$950,000

Amazing opportunity to own a charming 1830s home with a detached accessory apartment built in 2016. Renovated in 2003, this home sits on an acre of land surrounded by unbuildable land, offering privacy and a peaceful setting. With great bones and timeless appeal, the main house features a well-designed floor plan, a cozy living room with a wood-burning fireplace, and plenty of character throughout. Located in a fantastic spot close to the beach, this property combines historic charm with modern convenience. A separate 1 bedroom cottage adds flexibility—perfect for guests or extended family. A rare find in an unbeatable location! Room for pool!

4 Beds ⋅ 3 Baths ⋅ 820321 MLS

Amazing opportunity to own a charming 1830s home with a detached accessory apartment built in 2016. Renovated in 2003, this home sits on an acre of land surrounded by unbuildable land, offering privacy and a peaceful setting. With great bones and timeless appeal, the main house features a well-designed floor plan, a cozy living room with a wood-burning fireplace, and plenty of character throughout. Located in a fantastic spot close to the beach, this property combines historic charm with modern convenience. A separate 1 bedroom cottage adds flexibility—perfect for guests or extended family. A rare find in an unbeatable location! Room for pool!

9875 Main Bayview Road, Southold

$942,500

Welcome to 230 Booth Road, a prime Southold location offering effortless access to both Kenneys Beach and McCabe’s Beach-two of the North Fork’s most beloved Sound front destinations known for swimming, long shoreline walks, and unforgettable sunsets. This expanded cape provides exceptional flexibility for living and entertaining. The entry opens to a spacious living room with a cozy wood-burning fireplace, flowing into a dining room, both featuring oak floors currently protected by carpeting. The large eat-in kitchen offers abundant space for gatherings, with an adjacent laundry room and storage area that includes plumbing for an easy conversion to a powder room. Two bedrooms and a full bath complete the first floor. Upstairs, you’ll find three additional generous guest rooms and a full bath. An oversized walk-in attic presents potential for future expansion. The full basement offers ample storage, and Bilco doors make it simple to store outdoor furniture and seasonal items. Other features include a generator and new central air conditioning. The tranquil backyard provides plenty of room for summer entertaining. Whether you’re seeking a year-round residence or a seasonal escape, this home places you at the heart of the North Fork lifestyle—beautiful beaches, vineyards, farm stands, boutique shopping, and farm-to-table restaurants. This is the North Fork retreat you have been looking for.

5 Beds ⋅ 2 Baths ⋅ 1017107 MLS

Welcome to 230 Booth Road, a prime Southold location offering effortless access to both Kenneys Beach and McCabe’s Beach-two of the North Fork’s most beloved Sound front destinations known for swimming, long shoreline walks, and unforgettable sunsets. This expanded cape provides exceptional flexibility for living and entertaining. The entry opens to a spacious living room with a cozy wood-burning fireplace, flowing into a dining room, both featuring oak floors currently protected by carpeting. The large eat-in kitchen offers abundant space for gatherings, with an adjacent laundry room and storage area that includes plumbing for an easy conversion to a powder room. Two bedrooms and a full bath complete the first floor. Upstairs, you’ll find three additional generous guest rooms and a full bath. An oversized walk-in attic presents potential for future expansion. The full basement offers ample storage, and Bilco doors make it simple to store outdoor furniture and seasonal items. Other features include a generator and new central air conditioning. The tranquil backyard provides plenty of room for summer entertaining. Whether you’re seeking a year-round residence or a seasonal escape, this home places you at the heart of the North Fork lifestyle—beautiful beaches, vineyards, farm stands, boutique shopping, and farm-to-table restaurants. This is the North Fork retreat you have been looking for.

230 Booth Road, Southold

$940,000

Nestled on a wooded lot, this location feels private while only short distance to downtown Southold and 10 Minutes East to the Village of Greenport. With spacious, airy rooms and hardwood floors, this inviting residence promises a cozy and warm ambiance from the moment you step inside, hand painted wall mosaic, 2 fire places, Spacious Eat In Kitchen, Formal Dining room, Family room and when its time to relax step outside onto the Patio or front porch for a perfect spot to sit with a cup of coffee to observe the serene nature filled yard or the pool. HOA Fee of $150., Additional information: Interior Features:Lr/Dr

6 Beds ⋅ 3 Baths ⋅ L3509055 MLS

Nestled on a wooded lot, this location feels private while only short distance to downtown Southold and 10 Minutes East to the Village of Greenport. With spacious, airy rooms and hardwood floors, this inviting residence promises a cozy and warm ambiance from the moment you step inside, hand painted wall mosaic, 2 fire places, Spacious Eat In Kitchen, Formal Dining room, Family room and when its time to relax step outside onto the Patio or front porch for a perfect spot to sit with a cup of coffee to observe the serene nature filled yard or the pool. HOA Fee of $150., Additional information: Interior Features:Lr/Dr

1755 Yennecott Drive, Southold

$915,000

2070 Cedar Drive offers the kind of North Fork lifestyle buyers search for but rarely find — a welcoming home in a peaceful setting. There’s a sandy neighborhood beach right across the street and it’s positioned near other beaches, marinas, and North Fork vineyards. Located in a highly desirable Southold waterfront enclave, the property presents a compelling opportunity for both lifestyle buyers and long-term investors. Benefitting from strong seasonal demand and limited inventory in the immediate area, this 1.03-acre property represents not just a purchase — but a strategic hold in a supply-constrained coastal market. Beautifully updated and maintained, the two-bedroom, one-bath cottage features a cozy fireplace and gleaming hardwood floors, complemented by a recently renovated kitchen, glassed-in Florida room, central air, unfinished basement and a solid amount of upstairs bonus room space. Additional highlights include a generous two-car barn, lengthy circular driveway, and a serene park-like setting that enhances the overall appeal of this special property. Secure today. Appreciate tomorrow.

2 Beds ⋅ 1 Baths ⋅ 935245 MLS

2070 Cedar Drive offers the kind of North Fork lifestyle buyers search for but rarely find — a welcoming home in a peaceful setting. There’s a sandy neighborhood beach right across the street and it’s positioned near other beaches, marinas, and North Fork vineyards. Located in a highly desirable Southold waterfront enclave, the property presents a compelling opportunity for both lifestyle buyers and long-term investors. Benefitting from strong seasonal demand and limited inventory in the immediate area, this 1.03-acre property represents not just a purchase — but a strategic hold in a supply-constrained coastal market. Beautifully updated and maintained, the two-bedroom, one-bath cottage features a cozy fireplace and gleaming hardwood floors, complemented by a recently renovated kitchen, glassed-in Florida room, central air, unfinished basement and a solid amount of upstairs bonus room space. Additional highlights include a generous two-car barn, lengthy circular driveway, and a serene park-like setting that enhances the overall appeal of this special property. Secure today. Appreciate tomorrow.

2070 Cedar Drive, Southold

$910,000

Tucked away in a secluded waterfront setting, this charming bayside cottage offers a rare opportunity to enjoy peaceful North Fork living surrounded by natural beauty and captivating water views. Designed to embrace its exceptional location, the home features an open-concept living, dining, and kitchen area where abundant windows frame the water and fill the interior with natural light throughout the day. The seamless layout creates an inviting atmosphere for gathering with friends or simply relaxing while enjoying the tranquil waterfront setting. Offering two bedrooms and one bath, this retreat home provides the perfect escape from the everyday. Whether you're seeking a seasonal getaway or investment opportunity, the property's unique combination of privacy, water views, and North Fork charm is difficult to find.

2 Beds ⋅ 1 Baths ⋅ 1012280 MLS

Tucked away in a secluded waterfront setting, this charming bayside cottage offers a rare opportunity to enjoy peaceful North Fork living surrounded by natural beauty and captivating water views. Designed to embrace its exceptional location, the home features an open-concept living, dining, and kitchen area where abundant windows frame the water and fill the interior with natural light throughout the day. The seamless layout creates an inviting atmosphere for gathering with friends or simply relaxing while enjoying the tranquil waterfront setting. Offering two bedrooms and one bath, this retreat home provides the perfect escape from the everyday. Whether you're seeking a seasonal getaway or investment opportunity, the property's unique combination of privacy, water views, and North Fork charm is difficult to find.

723 Private Road Unit #12, Southold

$910,000

A beautiful and lovingly-maintained ranch with a front porch, set on a corner lot, offers a serene, country setting. Home features a primary bedroom ensuite, plus 2 comfortably-sized bedrooms, 2 full bathrooms and a bright, newly-renovated eat-in kitchen with French doors leading to a picturesque, level backyard with a patio. A spacious living room and family room with a brick, wood burning fireplace, both rooms accented with ceiling beams, offer an inviting layout. Solid wood flooring, central air, and a spacious 2-car garage, along with 5 spots in a circular driveway, are included in this wonderful home situated on a 1/2 acre lot. The full, unfinished basement may easily be enhanced for various uses including an entertainment area, gym and playroom. Enjoy this ideal location just 3 blocks from McCabe's Beach where the gorgeous Long Island Sound and sunsets await. Close to schools, shopping, dining, and major transportation routes, this move-in ready home is a rare opportunity that combines comfort, convenience and location.

3 Beds ⋅ 2 Baths ⋅ 978724 MLS

A beautiful and lovingly-maintained ranch with a front porch, set on a corner lot, offers a serene, country setting. Home features a primary bedroom ensuite, plus 2 comfortably-sized bedrooms, 2 full bathrooms and a bright, newly-renovated eat-in kitchen with French doors leading to a picturesque, level backyard with a patio. A spacious living room and family room with a brick, wood burning fireplace, both rooms accented with ceiling beams, offer an inviting layout. Solid wood flooring, central air, and a spacious 2-car garage, along with 5 spots in a circular driveway, are included in this wonderful home situated on a 1/2 acre lot. The full, unfinished basement may easily be enhanced for various uses including an entertainment area, gym and playroom. Enjoy this ideal location just 3 blocks from McCabe's Beach where the gorgeous Long Island Sound and sunsets await. Close to schools, shopping, dining, and major transportation routes, this move-in ready home is a rare opportunity that combines comfort, convenience and location.

6625 Hortons Lane, Southold

$910,000

Welcome to the charming and desirable Southwoods Community, located in the heart of the North Fork. This beautifully maintained, renovated ranch sits on just under half an acre and features three spacious bedrooms and spa-inspired bathrooms. The interior boasts refinished wood floors, a walk-up finished attic bonus room, and an updated eat-in kitchen equipped with granite countertops and stainless steel appliances. The open floor plan includes a casual eating area, a formal dining room, a living room, and a breezeway that connects to the two-car attached garage. The primary bedroom suite is generously sized and overlooks the private backyard, while the other two bedrooms enjoy ample natural light. The outdoor space is perfect for entertaining, featuring a fenced-in yard, a patio, and a wooden gazebo for gatherings with friends and family. There is also plenty of room for a pool, with a previous permit in place. Additional highlights include deeded access to a private association beach on Goose Creek, which leads out to Peconic Bay. The association park offers a kayak and watercraft launch, picnic area, and ample seating at both the beach and lawn. The roof was newly installed in 2021, and the property is perfectly positioned to explore the North Fork's beautiful amenities, including vineyards, Southold Town, fine dining, picturesque beaches, and charming local farm stands. Professional Photos Coming Soon

3 Beds ⋅ 1 Baths ⋅ 906052 MLS

Welcome to the charming and desirable Southwoods Community, located in the heart of the North Fork. This beautifully maintained, renovated ranch sits on just under half an acre and features three spacious bedrooms and spa-inspired bathrooms. The interior boasts refinished wood floors, a walk-up finished attic bonus room, and an updated eat-in kitchen equipped with granite countertops and stainless steel appliances. The open floor plan includes a casual eating area, a formal dining room, a living room, and a breezeway that connects to the two-car attached garage. The primary bedroom suite is generously sized and overlooks the private backyard, while the other two bedrooms enjoy ample natural light. The outdoor space is perfect for entertaining, featuring a fenced-in yard, a patio, and a wooden gazebo for gatherings with friends and family. There is also plenty of room for a pool, with a previous permit in place. Additional highlights include deeded access to a private association beach on Goose Creek, which leads out to Peconic Bay. The association park offers a kayak and watercraft launch, picnic area, and ample seating at both the beach and lawn. The roof was newly installed in 2021, and the property is perfectly positioned to explore the North Fork's beautiful amenities, including vineyards, Southold Town, fine dining, picturesque beaches, and charming local farm stands. Professional Photos Coming Soon

600 Parkway, Southold

$899,000

Build Your Dream Estate in Southold. Prime 2 Acre Corner Lot Near the Beach An exceptional opportunity awaits in one of Southold’s most desirable neighborhoods. This premium 2-acre corner parcel provides the ideal setting to design and build a custom luxury residence with plenty of room for a pool, pool house, guest cottage, tennis or pickleball courts, lush gardens, and expansive outdoor living spaces. The location is unmatched; just moments from gorgeous beaches, acclaimed vineyards, farmstands, and the charming Southold village center, offering the perfect balance of tranquility and convenience. Major due diligence items have already been completed, including an updated property survey, Suffolk County Board of Health approval, and preliminary site and building plans, making this a smooth path toward your vision. With privacy, natural beauty, and endless potential, this property is the perfect canvas to craft your forever home or seasonal North Fork retreat. A rare offering in a true destination location — explore the possibilities and make your dream home a reality.

942473 MLS

Build Your Dream Estate in Southold. Prime 2 Acre Corner Lot Near the Beach An exceptional opportunity awaits in one of Southold’s most desirable neighborhoods. This premium 2-acre corner parcel provides the ideal setting to design and build a custom luxury residence with plenty of room for a pool, pool house, guest cottage, tennis or pickleball courts, lush gardens, and expansive outdoor living spaces. The location is unmatched; just moments from gorgeous beaches, acclaimed vineyards, farmstands, and the charming Southold village center, offering the perfect balance of tranquility and convenience. Major due diligence items have already been completed, including an updated property survey, Suffolk County Board of Health approval, and preliminary site and building plans, making this a smooth path toward your vision. With privacy, natural beauty, and endless potential, this property is the perfect canvas to craft your forever home or seasonal North Fork retreat. A rare offering in a true destination location — explore the possibilities and make your dream home a reality.

195 Mt Beulah Avenue, Southold

$899,000

Stately and classic vintage farmhouse with wrap-around porch, original in-tact architectural details and hardwood floors throughout. Built in 1900 as part of the Southold Hotel on Main Road. Moved to current location in 1920. Beautifully maintained with lots of natural light, eat-in kitchen, large private back yard, walking/biking distance to Southold Village and Founders Landing Park with playground, clubhouse, & bay beach. Walk to Southold Village shops & restaurants, LIRR & Jitney.

3 Beds ⋅ 2 Baths ⋅ 922975 MLS

Stately and classic vintage farmhouse with wrap-around porch, original in-tact architectural details and hardwood floors throughout. Built in 1900 as part of the Southold Hotel on Main Road. Moved to current location in 1920. Beautifully maintained with lots of natural light, eat-in kitchen, large private back yard, walking/biking distance to Southold Village and Founders Landing Park with playground, clubhouse, & bay beach. Walk to Southold Village shops & restaurants, LIRR & Jitney.

385 Cottage Place, Southold

$890,000

***NEW IMPROVED PRICE**Ideal for the Self-Employed Buyer or Multigenerational family: Flexibility, and Income Potential in Southold’s Wine Country. This beautifully renovated farmhouse blends timeless charm with modern comfort—perfectly suited for self-employed professionals. With 5 spacious bedrooms and 3 elegantly updated bathrooms across 2 floors, this home offers flexibility. A comprehensive gut renovation done less than five years ago, gives buyers the opportunity to unpack and enjoy! For those looking to generate additional income or accommodate multigenerational living, the layout provides an ideal opportunity—pending proper permits—to create a separate 2-bedroom, 1-bath rental unit. This option adds a layer of flexibility and long-term value for self-employed buyers who may benefit from rental income or guest accommodations. A full basement offers generous storage and the potential for a home gym, studio, or workshop. The detached 1.5-car garage and two driveways offer parking for up to 8 vehicles! The spacious yard provides plenty of room for a pool or outdoor entertaining. Located just minutes from pristine beaches and only a mile from Southold’s quaint downtown with shops, dining, and a vibrant local scene, the home is also close to farm stands, award-winning wineries, breweries, and boating—making it the ideal base for a fulfilling and inspired lifestyle.

5 Beds ⋅ 3 Baths ⋅ 840724 MLS

***NEW IMPROVED PRICE**Ideal for the Self-Employed Buyer or Multigenerational family: Flexibility, and Income Potential in Southold’s Wine Country. This beautifully renovated farmhouse blends timeless charm with modern comfort—perfectly suited for self-employed professionals. With 5 spacious bedrooms and 3 elegantly updated bathrooms across 2 floors, this home offers flexibility. A comprehensive gut renovation done less than five years ago, gives buyers the opportunity to unpack and enjoy! For those looking to generate additional income or accommodate multigenerational living, the layout provides an ideal opportunity—pending proper permits—to create a separate 2-bedroom, 1-bath rental unit. This option adds a layer of flexibility and long-term value for self-employed buyers who may benefit from rental income or guest accommodations. A full basement offers generous storage and the potential for a home gym, studio, or workshop. The detached 1.5-car garage and two driveways offer parking for up to 8 vehicles! The spacious yard provides plenty of room for a pool or outdoor entertaining. Located just minutes from pristine beaches and only a mile from Southold’s quaint downtown with shops, dining, and a vibrant local scene, the home is also close to farm stands, award-winning wineries, breweries, and boating—making it the ideal base for a fulfilling and inspired lifestyle.

4100 Youngs Avenue, Southold

$882,000

Unique opportunity in Southold to create your dream home on the North Fork. This A-frame-style house, reminiscent of a chalet, features a striking wall of windows that leads to open rafter ceilings. The main floor is perfect for entertaining, with a quaint kitchen, two bedrooms, a full bathroom, and the sunken A-frame living room that captures the essence of the home. Adjacent to the living room, sliding doors open to a wrap-around deck overlooking the side yard, which is ideal for al fresco dining or enjoying an evening gathered around the fire pit. Upstairs, you'll find a spacious loft that can serve as an office, recreational space, or lounge. The loft includes a balcony that overlooks the living room and provides access to a mini rooftop terrace with views of the backyard. The lower level, which has a private entrance, is ready for full renovation and is already framed for a potential bedroom, bathroom, laundry room, and additional storage. The two-car attached garage can be repurposed for additional living space or perhaps a gym. The property encompasses 1.37 acres, having been merged with the adjacent land, providing ample space for a potential pool, tennis court, or additional structures while ensuring plenty of privacy. Wonderful investment opportunity. You'll also enjoy convenient access to the beaches of Southold Bay, the village, and local vineyards. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.

2 Beds ⋅ 1 Baths ⋅ 983742 MLS

Unique opportunity in Southold to create your dream home on the North Fork. This A-frame-style house, reminiscent of a chalet, features a striking wall of windows that leads to open rafter ceilings. The main floor is perfect for entertaining, with a quaint kitchen, two bedrooms, a full bathroom, and the sunken A-frame living room that captures the essence of the home. Adjacent to the living room, sliding doors open to a wrap-around deck overlooking the side yard, which is ideal for al fresco dining or enjoying an evening gathered around the fire pit. Upstairs, you'll find a spacious loft that can serve as an office, recreational space, or lounge. The loft includes a balcony that overlooks the living room and provides access to a mini rooftop terrace with views of the backyard. The lower level, which has a private entrance, is ready for full renovation and is already framed for a potential bedroom, bathroom, laundry room, and additional storage. The two-car attached garage can be repurposed for additional living space or perhaps a gym. The property encompasses 1.37 acres, having been merged with the adjacent land, providing ample space for a potential pool, tennis court, or additional structures while ensuring plenty of privacy. Wonderful investment opportunity. You'll also enjoy convenient access to the beaches of Southold Bay, the village, and local vineyards. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.

600 Highwood Road, Southold