Riverhead Homes with Pool

Welcome to Riverhead, NY, a charming town nestled in the heart of Suffolk County on Long Island. Known for its rich history, vibrant culture, and stunning natural landscapes, Riverhead offers a unique blend of suburban tranquility and urban convenience. With its picturesque waterfront along the Peconic River, this thriving community is perfect for families, retirees, and anyone seeking a serene lifestyle with easy access to the bustling attractions of Long Island.

One of the standout features of Riverhead is its diverse real estate market, which includes a delightful selection of homes with pools. Imagine stepping out into your backyard oasis on a warm summer day, where you can unwind by your private pool, host barbecues with friends, or enjoy a refreshing dip after a long day. These homes are designed for relaxation and entertainment, providing the perfect backdrop for creating cherished memories with loved ones.

Riverhead is not just about beautiful homes; it also boasts an array of recreational activities. From the renowned Long Island Aquarium to the picturesque vineyards of the North Fork, there’s always something to explore. Residents can enjoy a leisurely stroll through local parks, indulge in shopping at unique boutiques, or savor delicious cuisine at a variety of restaurants.

Whether you're looking to buy your dream home with a pool or simply want to learn more about the Riverhead lifestyle, this vibrant town offers the perfect setting for your next chapter. Come experience the warmth and charm 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

$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

$229,999

2 Beds ⋅ 2 Baths ⋅ 1019381 MLS

55+ Manufactured Home Land Lease Community Glenwood Village Starting at $800 per month - This Villager Model Features 2 Bedrooms, 2 Baths, LR, Kitchen, Laundry Rm, & Florida Room. Central Air, Fans, Laminate Flooring - Dutch Door Shed, Patio Area, Sprinkler System, CAC, & Cement Walkway around home. Nicely landscaped, #1 Oil for Heating, Propane for Cooking & Hot water And A Short Walk To The Pool Or Clubhouse

1661 Old Country Road Unit #125, Riverhead

$1,497,000

3 Beds ⋅ 3 Baths ⋅ 1007258 MLS

Welcome to this bright and spacious home designed for comfort, entertaining, and everyday living. The main level features an impressive open layout with soaring ceilings, skylights, hardwood floors, and abundant natural light throughout. The main living room is centered around a dramatic two-sided brick fireplace and flows beautifully into the dining area, kitchen, and family room. The open-concept kitchen offers white cabinetry, stainless steel appliances, ample counter space, and a breakfast bar overlooking the living areas. The dining room is filled with natural light and offers direct access to the expansive outdoor deck, creating an easy indoor-outdoor flow. On the opposite side of the shared fireplace, the family room provides another inviting gathering space with vaulted ceilings, arched windows, exposed beams, and access to the pool area. The private principal en-suite bedroom is set apart from the other bedrooms and living spaces, featuring vaulted ceilings, exposed beams, walk-in closets, and a balcony overlooking the pool and jacuzzi. The full en-suite bathroom offers generous space, high ceilings, great natural light, a jacuzzi-style tub, separate shower, and double vanity. Additional bedrooms are well-sized and comfortable, with access to beautifully maintained full bathrooms. Upstairs, an open den area overlooks the main living room below, offering a versatile space for reading, working, or relaxing before entering the principal bedroom suite. The finished basement adds even more living space with a spacious media and recreation room, lounge area, ping pong/game space, built-in storage, coffee station, laundry area, and additional storage/mechanical space. The exterior is a true highlight, featuring a large deck surrounding the in-ground pool and jacuzzi, multiple patio areas, outdoor dining and lounge spaces, a firepit area, garden beds, and a spacious yard surrounded by mature trees and landscaping. With multiple sliding doors leading outside, this home is ideal for entertaining, relaxing, and enjoying the outdoor setting. A private driveway and attached garage complete the property.

220 Pleasure Drive, Riverhead

$1,199,000

4 Beds ⋅ 4 Baths ⋅ 986406 MLS

Set within the serene landscape of Rolling Woods in Riverhead, 59 Linda Lane West presents a rare blend of privacy, thoughtful design, and resort-inspired living on the North Fork. Positioned on a beautifully maintained and three quarter acre property, this residence is surrounded by mature landscaping that creates a peaceful, secluded setting while remaining close to the area’s celebrated beaches, farm stands, vineyards, and dining destinations. A residents-only beach nearby, and public beach with four wheel drive access, enhances the coastal lifestyle, offering easy access to the shoreline and the natural beauty that defines this region. The home’s interior unfolds with a sense of openness and warmth architectural details complement light-filled living spaces designed for both everyday comfort and effortless entertaining. Hardwood floors extend throughout, guiding you through generously sized rooms that balance sophistication with livability. The kitchen is well appointed with quality finishes, ample cabinetry, and stainless steel appliances, creating a functional and inviting space that connects seamlessly to the main living and dining areas. A flexible layout includes four bedrooms and 3.5 bathrooms, along with a finished lower level featuring a bath and wet bar, offering additional space for recreation, relaxation, or extended living. Outdoor living is equally compelling, anchored by a striking L-shaped heated saltwater pool with a multi-speed pump and an expansive patio that invites long afternoons of sun, quiet evenings, and gatherings under the open sky. The grounds are enhanced by a sauna, and hot tub, creating a private retreat designed for year-round enjoyment. Additional highlights include a two-car attached garage with an electric vehicle charger, solar panels for energy efficiency, updated systems including heating, windows, and furnace, and the convenience of an elevator that adds ease of access throughout the home. This property captures the essence of North Fork living, where natural beauty, comfort, and thoughtful amenities come together in a setting that feels both tranquil and connected.

59 Linda Lane W, Riverhead

$329,000

2 Beds ⋅ 2 Baths ⋅ 984696 MLS

Welcome to Glenwood Village - a 55 & Over Community Offering a 49 Year Lease starting at $800 per month. This Ranch Style Home features One Level Living at its finest! 2 Lovely Appointed Bedrooms and 2 Baths - Open Kitchen, Dining & Living Room Area - Laundry Room is Located off the Kitchen and makes its way out to A Covered Deck Overlooking a Pond. Carport, CAC, Shed & Spinkler System. Community Offers an Outdoor Park, Swimming Pool, Clubhouse with a State of the Art Gym, Library, Billiard Pool Room, Dance Hall & Full-Size Kitchen.

1661 Old Country Road Unit #417, Riverhead

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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.