Riverhead Homes with Pool

Welcome to Riverhead, NY – a vibrant community nestled in the heart of Suffolk County. Renowned for its rich history and diverse culture, Riverhead offers an exceptional quality of life and is home to one of the most sought-after school districts in the region. The Riverhead Central School District prides itself on providing a well-rounded education, fostering academic excellence, and preparing students for a successful future. With a commitment to innovation, the district boasts a range of programs, from advanced placement courses to arts and athletics, ensuring every child has the opportunity to thrive.

As you explore the charming neighborhoods of Riverhead, you’ll discover a variety of beautiful homes, many of which come with the luxury of a private pool. Imagine spending warm summer days lounging by your own oasis, hosting unforgettable barbecues, or enjoying peaceful evenings under the stars. Homes with pools in Riverhead not only enhance your lifestyle but also add a touch of elegance and relaxation to your daily routine.

Riverhead is strategically located, making it easy to access the stunning beaches of the East End, vibrant local wineries, and the enchanting charm of downtown Riverhead. With its strong sense of community, excellent schools, and a range of recreational activities, Riverhead is the perfect place to call home. Whether you’re looking for a family-friendly environment or a serene retreat, you’ll find it here, complete with the luxury of a pool to enjoy all year round. Discover the beauty of Riverhead, where your dream home awaits!

Newest Riverhead Homes with Pool

$249,999

2 Beds ⋅ 2 Baths ⋅ 1032525 MLS

The Well Sought After 55 & Over Community - Glenwood Village is offering a 49 year lease at $800 per month. This Most Popular Model - The Villager offers split bedrooms and baths at opposite ends of the home. 2 Bedrooms, 2 Baths, LR, Open Floor Plan, Dining Area in Kitchen with appliances, Laundry Rm. Home features wood cabinets, Laminate Flooring, washer/dryer CAC, Sprinkler System, 10x20 Composite Decking with Vinyl Rails & Shed. It’s even is wired for a generator in case you lose power! Access to Outdoor park, pool, & Clubhouse. Come and Enjoy all that Glenwood has to Offer.

1661 Old Country Road Unit #84, Riverhead

$680,000

3 Beds ⋅ 2 Baths ⋅ 1031536 MLS

Coming Soon. A classic Riverhead Cape Cod, beautifully updated, with three bedrooms, two full baths, a legal finished basement, and an inground pool set in a private backyard built for entertaining. Located minutes from downtown Riverhead's waterfront dining and the restored Suffolk Theater, at the gateway to the East End with easy reach of North Fork wine country and the Hamptons. Will get accurate Square footage, full details and photos coming soon. On Market Date: 8/3/2026

60 Hubbard Avenue, Riverhead

$1,150,000

4 Beds ⋅ 3 Baths ⋅ 1030183 MLS

Welcome to 4 Apple Lane—Your Private Wading River Oasis Nestled in the quaint, sought-after town of Wading River, 4 Apple Lane offers a perfect blend of peaceful privacy and high-value modern upgrades. Spanning 3,300 square feet on an impressive 1.76 plush, park-like acres, this home is a true sanctuary designed for both comfortable daily living and effortless grand-scale entertaining. Sun-Drenched Living & Warm Architectural Details Step inside the welcoming foyer and immediately experience a remarkably bright, open, and airy ambiance filled with natural sunlight from an abundance of large windows. The main level flows effortlessly, offering a large formal living room, an expansive formal dining room, and an inviting den featuring rich, custom built-in cabinetry. Adding to the home's warmth and charm is a cozy wood-burning fireplace, perfect for relaxing on cool evenings. Chef’s Kitchen & Modern Upgrades At the heart of the main floor is the chef’s kitchen—a culinary haven designed for function and style. Upgraded for modern convenience, the kitchen features top-tier updates including a microwave updated in May 2023, a dishwasher and stove/oven replaced in 2022, and a brand-new refrigerator added in 2025. Serene Primary Suite & Renovated Baths Upstairs, the sprawling main bedroom serves as a true primary retreat—expansive, sunlit, and serene. It boasts a beautifully updated full main bathroom complete with a deep soaking tub and a sleek stand-up shower (remodeled in 2019/2020). The additional bedrooms offer generous proportions and easy access to thoughtfully renovated full baths (upstairs bath updated in 2019/2020, and the downstairs bath updated in 2021). Substantial Energy Savings & Future Potential Adding immense value, this home is powered by fully paid-off solar panels. Enjoy the luxury of living practically electric-free, with summer electric bills dropping as low as $19 per month! Downstairs, the full, unfinished basement boasts approx. 8-foot ceilings, offering incredible potential for customization, a home gym, or additional living space. A Resort-Style Backyard Sanctuary Step outside to your personal outdoor retreat featuring a charming side garden and a massive 1,000 sq. ft. cedar deck (20x50, built in 2020). Beyond the deck lies the star of the yard: an oversized 22x42 saltwater pool reaching depths of 9 feet, equipped with a 2018 liner, a 2020 pump, and full reconditioning in 2025. Two 12x14 storage sheds near the pool add effortless convenience. Complete with a brand-new roof (June 2025), an updated 200-amp electrical panel, washer/dryer (Nov 2021), a 3-car garage, and an oversized multi-car driveway, 4 Apple Lane is a turnkey Wading River gem waiting to welcome its next owner home!

4 Apple Lane, Wading River

$780,000

3 Beds ⋅ 1 Baths ⋅ 1029041 MLS

Welcome to 61 Timber Drive in Calverton! This charming ranch offers so much more than meets the eye—you truly have to see it to appreciate all it has to offer. Nestled on beautifully landscaped property, this lovingly maintained home features major improvements completed within the last two years, including the roof, siding, and central air conditioning, providing both style and peace of mind. Surrounded by mature landscaping, the property offers the perfect setting for entertaining or simply enjoying peaceful outdoor living. The impressive detached 2.5-car garage is ideal for car enthusiasts, extra storage, or creating the ultimate workshop or hobby space. Combined with exceptionally low taxes, this home presents an incredible opportunity and is truly one you have to see to believe.

61 Timber Drive, Calverton

$3,795,000

4 Beds ⋅ 4 Baths ⋅ 1027302 MLS

There are properties that offer more space, and then there are places that offer an entirely different way of living. Positioned in the heart of the North Fork, Starry Night Farms invites you to embrace a way of life that has become increasingly sought after yet is rarely found. Set on 6.3 exquisite acres, this remarkable equestrian estate is ideal for horse enthusiasts, hobby farmers, and those seeking an exceptionally private retreat. The charming yet updated farmhouse welcomes you with a classic covered wraparound porch, inviting interiors, and a bright rear sunroom overlooking the picturesque grounds, Outdoors, a heated saltwater pool, custom barbecue kitchen, and outdoor fireplace provide the perfect setting for entertaining family and friends. Designed with an equestrian lifestyle in mind, the property features two barns, indoor and outdoor riding arenas, ten horse stalls in total, and a dedicated tack room. Beyond its equestrian amenities, the property is filled with distinctive features, including a wine barrel sauna with steam and hot rocks, an art studio, putting green, and 16 raised garden beds ready for farm-to-table living. Apple, nectarine, cherry, and peach trees flourish throughout the backyard, while an established chicken coop with 20 chickens, productive Flow beehives, and multiple outbuildings offer exceptional flexibility. The grounds are further enhanced by a vineyard with thriving Merlot grapevines, creating an idyllic country setting where luxury and sustainable living come together. This one-of-a-kind Jamesport estate presents a rare opportunity to enjoy refined country living, premier equestrian facilities, and resort-style wellness amenities within one extraordinary property. Luxury is no longer defined simply by what you own, but by how you live.

1810 Main Road, Jamesport

$999,000

4 Beds ⋅ 3 Baths ⋅ 1026993 MLS

Circa 1921, this charming and thoughtfully updated 4-bedroom, 2.5-bath residence beautifully blends historic character with modern comfort. Lovingly maintained and improved throughout, this exceptional home offers a spacious and versatile layout designed for today's lifestyle. Inside, you'll find a warm and inviting floor plan featuring a stunning wood-burning stone fireplace, original pine floors throughout much of the home that add warmth and timeless character, an updated kitchen with granite countertops and newer appliances, beautifully renovated bathrooms, a convenient first-floor laundry/mud room, and an oversized Andersen sliding glass door overlooking the expansive backyard. A second staircase provides easy access to the primary bedroom while adding to the home's unique character and functionality. Numerous updates and improvements provide peace of mind, including a newer boiler, updated mechanicals, 200-amp electric service, smart thermostats, a central vacuum system, and thoughtful upgrades throughout. The basement and generous attic space offer additional storage and flexibility. Outside, enjoy a beautifully landscaped property designed for entertaining and relaxation. The backyard features a saltwater in-ground pool with new coping and a new filter, a new paver patio, in-ground sprinklers with a private well water irrigation system, and plenty of room for gatherings, recreation, and outdoor enjoyment. A huge detached two-car garage with new windows, equipped with an electric car charging station, provides ample parking and storage, along with a newly finished climate-controlled bonus room-perfect for a hobby space, studio, gym, workshop, home office, or private retreat. Combining timeless charm, modern updates, and exceptional outdoor living, this rare property offers the opportunity to own a piece of history with all the conveniences of today. Perfectly situated in the heart of Riverhead, this home offers the best of East End living. Enjoy easy access to downtown waterfront, local dining, shops, entertainment, and year-round events, while being just minutes from farms, vineyards, beaches, golf courses, and everything the East End has to offer.

312 Riverside Drive, Riverhead

$899,000

3 Beds ⋅ 2 Baths ⋅ 1026812 MLS

Perfectly positioned **north of Sound Avenue** in one of Riverhead's most desirable locations, this 3-bedroom, 3-full-bath ranch offers the ideal blend of privacy, flexibility, and in need of a new loving owner. This home's provides a North Fork lifestyle that's mere a stone's throw to the Sound where Sunsets are magical. Nestled on a generously sized property, the backyard has been thoughtfully designed to maximize both privacy and functionality. A **legal in-ground swimming pool** is strategically situated to create your own private retreat while preserving an expansive lawn—perfect for entertaining, recreation, gardening, or simply enjoying the outdoors. Inside, the home's versatile floor plan continues with a **fully finished basement** featuring a spacious recreation room, full bathroom, dedicated laundry room, and **three separate points of access**: interior access from the main level, a sliding glass door providing direct walkout access to the backyard, and a separate entrance through the attached garage. This exceptional layout presents outstanding potential for extended living, guest accommodations, a home office, fitness space, or multi-generational living (subject to applicable permits and approvals). Located just moments from the best of the North Fork, you'll enjoy convenient access to renowned wineries and vineyards, farm stands, golf courses, local beaches, waterfront dining, marinas, parks, and the charming villages that make this area one of Long Island's most sought-after destinations. Whether spending the day exploring wine country, relaxing by the water, or enjoying the region's celebrated culinary scene, you'll appreciate having it all just minutes from home. Riverhead's location also provides easy access to shopping, entertainment, and transportation while maintaining the peaceful atmosphere that defines North Fork living. Offering privacy, exceptional indoor and outdoor living spaces, and endless possibilities to customize for your lifestyle, 20 Dolphin Way is a rare opportunity to experience the very best of North Fork living.

20 Dolphin Way, Riverhead

$239,999

2 Beds ⋅ 2 Baths ⋅ 1024299 MLS

This Lovely Home is Located in The Sought After 55 & Over Manufactured Home Community, Glenwood Village. Offering a 49 Year Lease Starting at $800 per month. Includes Water, Garbage Pick up, Cesspool Maintenance, Curbside Mail Delivery, Use of Outdoor Pool, Park & Clubhouse, Snow Removal (Streets & Common Area Only)- 233 Glynwood Offers A Freshly Painted interior - 2 Bedrooms, 2 Updated Baths, At Opposite Ends of Home. It Boasts 2 Covered Decks, A Carport, 12x20 Sunroom, Updated Kitchen with A Movable Island, & A Nicely Sized Living Room The Owners Have Put in So Many Upgrades Both Inside & Out - You’ll Be Pleasantly Surprised. Shed, CAC, Sprinkler System, Fully Landscaped, Along with Concrete Walkways.

1661 Old Country Road Unit #233, Riverhead

$825,000

3 Beds ⋅ 3 Baths ⋅ 1020411 MLS

Beautifully renovated, beautifully landscaped, and ready to impress. Welcome to 138 Hallock Street, Riverhead, where classic charm meets modern comfort. Renovated in 2019, this spacious home offers 3 oversized bedrooms, 3 full baths, and a first-floor bonus room that can easily serve as a 4th bedroom, home office, or guest space. The inviting interior features a gas fireplace, natural gas heat, and a layout designed for both everyday living and entertaining. An enclosed front porch provides the perfect spot to enjoy your morning coffee or unwind at the end of the day. Outside, the beautifully landscaped corner property creates a private setting for summer enjoyment. The inground pool is ready for relaxing afternoons and entertaining family and friends, while the detached two-car garage with an unfinished loft offers outstanding potential for additional living space, a studio, gym, or abundant storage. This is a home that offers space, flexibility, and room to grow, all in a convenient location.

138 Hallock Street, Riverhead

$1,895,000

4 Beds ⋅ 4 Baths ⋅ 1021468 MLS

Move-In Ready and Furnished, Ultra-Luxury, Brand-New Construction! Featuring an Exclusive Imported Woodtone Hardie Plank Exterior with an Unmatched, Gorgeous Two-tone Finish that Requires No Maintenance. Complete with a $150,000 Landscaping Package and Set Back 1,000 Feet from the Road, this 1.2-Acre Estate Lot Seamlessly Blends Natural Beauty and Privacy, Epitomizing the North Fork Aesthetic at its Finest. The Open-concept First Floor is Perfect for Entertaining, Anchored by a Bespoke Chef’s Kitchen Featuring a Cambridge Quartz Island with a 2.5-inch Mitered Edge, Full-height Backsplash, and Double-stacked Premium Custom Cabinetry. A First-floor Bedroom Suite with Full Bath Offers an Ideal Option for Guests or Single-level Living. The Second Floor Hosts a Spacious Primary Suite with a Magnificent Spa Bath and Sweeping Views Over Vast Protected Farmland. The Lower Level Spans the Home’s Full Footprint, with Soaring Ceilings, Chic Plank Flooring, Recessed Lighting, an Exterior Entrance, and Three Egress Windows. Outside, a 20x40 Heated Saltwater Pool and Custom Masonry Patio Overlook Acres of Protected Open Space - the Perfect Backdrop for Unforgettable North Fork Sunsets and Countless Memories with Family and Friends. Every Detail for Modern Luxury Living Was Considered, Including a Full Smart Home Integration Package and Electric Vehicle Charging Outlet. With the Home, Pool, and Lush Landscaping Fully Complete and the Certificate of Occupancy Expected in Two Weeks, This is the Ultimate Turnkey Masterpiece!

22 Tuthills Lane, Jamesport

$1,975,000

4 Beds ⋅ 4 Baths ⋅ 1020064 MLS

A++ Hampton Bays Gem with 4 Beds and 4 Baths 20x40 Pool Rarely does a home and property of this quality, design, and value come to market. This shingled traditional colonial offers nearly 4,000 sq. ft. of beautiful, light filled living spaces. The first-floor flows seamlessly from room to room, beginning with a gracious entrance foyer flanked by living and dining rooms. A large gathering room with a sleek paneled fireplace wall opens to a breakfast area with glass doors to the outdoors and a chef's kitchen with top tier appliances spanning the entire rear of the home. This level also includes a full bathroom, laundry, and a flexible room that can serve as a bedroom, home theater, or office, along with an attached heated two car garage with high-quality built-in storage shelving and an EV connection. The primary suite upstairs features a vaulted ceiling, Lutron automated blinds, a large walk-in closet with California Closets shelving, and a marble bathroom with a soaking tub. Two additional spacious bedrooms, one of them with additional office space, and a full bathroom complete this floor. The home also includes approximately 1,000 sq. ft of fully finished, town approved lower-level space, completed in 2022, designed with a gym, sauna, wet bar, full bathroom, media room, office space, and a generous utility room with storage. A 120-inch-wide Light Well egress window creates an open, airy feel in the lower level while ensuring proper egress. The house features a fully enhanced state-of-the-art audio and video system inside and out, a five zone HVAC system, sophisticated lighting, security cameras, extensive automations, and a smart controlled gas fireplace. All systems are managed from a central Control4 rack that includes satellite TV, two Apple TVs, high performance amplifiers, and integration for five TVs throughout the home including an outdoor TV. Everything can be operated anywhere in the world via phone or iPad. Outside, the professionally landscaped one acre property includes a large 20 by 40 heated saltwater pool with a brand-new liner, a gas fire pit, nine remotely managed irrigation zones, a playground, lush specimen plantings and trees, and a prewired area ready for an already town-approved hot tub. The home sits in a secluded quiet area, minutes from bay beaches, village shops, and restaurants.

11 Hildreth Road, Hampton Bays

$2,100,000

4 Beds ⋅ 5 Baths ⋅ 1001049 MLS

Welcome to Sea Crest Estates, a new 13-home luxury community located around the corner from Jamesport’s Iron Pier Beach. This exceptional new-construction residence blends timeless architecture, designer finishes, and modern energy efficiency with a spacious open-concept floor plan. The first level features soaring ceilings, oversized Andersen 400 Series windows, and six-inch wide-plank white oak flooring throughout. The chef’s kitchen is appointed with quartz countertops, custom cabinetry, Kohler fixtures, and stainless-steel appliances with wine fridge opening seamlessly to the living room with a gas fireplace and dining area. The first-floor primary ensuite features a spa-inspired bathroom with elevated designer finishes, separate tub, oversize shower and double sinks. The first floor also has a separate room that can be used as an office, den or flex space. Upstairs there are 3 en-suite bedrooms and an unfinished bonus room which can be finished for more square footage. The mudroom off the 2 car garage offers abundant custom cabinetry and storage. Additional highlights include custom millwork, two laundry areas, and a full semi-finished basement with 8ft ceilings and private exterior access. Sliding doors lead to a private backyard oasis with a covered deck, 16x32 heated saltwater pool, paver patio, professional landscaping, and irrigation. Designed to exceed Energy Star standards with spray foam insulation, a tankless hot water system, ERV fresh-air system, and three-zone heating and central air. Estimated annual taxes are $27,340.

7 Sea Crest Court, Jamesport

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.