Browse All Roslyn NY 5 Bedroom Properties for Sale

Welcome to 18 Regent Place, a beautifully maintained 5-bedroom, 4-bath home offering a spacious layout and thoughtfully designed indoor and outdoor living. The first floor features two bedrooms and two full baths, including the original primary suite. Upstairs, you'll find an updated primary suite, an additional bedroom with ensuite access to a full bath that also opens to the hallway, a fifth bedroom, and a convenient second-floor laundry room. Additional features include radiant heat in the foyer, kitchen, dining room, and bathrooms, custom-fitted closets throughout, central vacuum, a hardwired speaker system, high ceilings, oversized windows, and generous storage. The backyard is designed for entertaining and relaxation, featuring a heated saltwater in-ground pool, outdoor kitchen with a gas hookup for the BBQ and automatic awning, outdoor speakers, and professionally landscaped grounds. The pool also includes an automatic water filler connected to the sprinkler system for added convenience.

18 Regent Place, Roslyn

$3,189,000

5 Beds ⋅ 5 Baths ⋅ 1020580 MLS

Perfectly positioned in The Links, one of the most desirable luxury gated communities that offers 24/7 security, this extensively remodeled residence offers a rare combination of sophisticated design, exceptional functionality, and premium amenities. Reimagined through a thoughtful structural expansion and comprehensive renovation, the home has been meticulously redesigned to maximize space, comfort, and everyday living. The welcoming main level features beautifully proportioned principal rooms that flow effortlessly for both entertaining and daily life. At the heart of the home is a stunning eat-in kitchen appointed with custom wood cabinetry, quartzite countertops, premium appliances, neutral designer finishes, and a generous center island. Wide-plank engineered maple flooring, custom millwork, upscale lighting, and a gas fireplace enhance the home’s refined aesthetic throughout. Designed with convenience in mind, the residence offers 3 bedrooms, 5 baths, dual primary suite options, and an elevator providing seamless access to every level. The finished walk-out lower level includes a spacious recreation area, kitchenette, bedroom and an oversized dedicated laundry room, offering exceptional flexibility for today’s lifestyle. Significant improvements include all-new plumbing, electrical, ductwork, dual HVAC systems, two generators, a new roof, garage door and motor, updated washer, dryer, internet wiring, and numerous additional mechanical and cosmetic enhancements. Outdoor living is equally inviting with a refinished rear deck overlooking peaceful open meadow views. Residents of The Links enjoy a clubhouse with fitness center, 2 pools, locker rooms, card and party rooms, along with professionally managed, meticulously maintained grounds. Located in a premier setting within the community, the residence presents a rare opportunity to own one of The Links’ most comprehensively updated homes within the community.

323 Baltustrol Circle, Roslyn

$1,998,000

5 Beds ⋅ 5 Baths ⋅ 1016057 MLS

Situated in the highly desirable Pines neighborhood of Roslyn, with access to the Pool Club, this elegant home offers the perfect blend of comfort, functionality, and timeless charm. Filled with natural light, the open floor plan creates a bright and welcoming atmosphere, complemented by soaring ceilings throughout. The spacious eat-in kitchen is ideal for everyday living and entertaining. The home features a grand entry foyer, a living room with dramatic high ceilings, a formal dining area, a large den With Fireplace, and a generous primary suite with a full bath. A fully finished basement provides additional living and recreation space, offering flexibility for a variety of needs. Ideally located near premier shopping, major highways, the LIRR, and within the Roslyn School District, this exceptional residence seamlessly combines style, comfort, and convenience.

4 Verity Lane, Roslyn

$2,498,888

5 Beds ⋅ 5 Baths ⋅ 1012402 MLS

Exceptional Opportunity — Estimated %25 Tax reduction for 28-29 Tax Roll. A striking contemporary retreat where architecture and nature come together seamlessly. This expansive nearly 5,000-square-foot residence is defined by soaring ceilings, walls of glass, and breathtaking views that bring the surrounding greenery indoors, creating a bright and tranquil living experience throughout. Designed for both everyday comfort and effortless entertaining, the open-concept floor plan features a dramatic living room with cathedral ceilings and a fireplace, an inviting family room, and a sun-drenched Florida room overlooking lush landscapes with seasonal views of Hempstead Harbor. At the heart of the home is a chef’s kitchen showcasing custom cabinetry, Italian imported elegant marble , and an impressive 11-foot center island perfect for gathering with family and friends. The upper level offers four spacious bedrooms with soaring cathedral ceilings, two hallway baths, and two versatile open loft-style spaces ideal for a home office, library, or lounge area. The luxurious primary suite serves as a private sanctuary featuring a spa-inspired bath with a unique imported onyx stone, heated floors and an oversized walk-in closet. The walk-out lower level expands the living space with a generous recreation area, private guest quarters with a full bath, a theater room, laundry room, and sliding doors leading directly to the backyard. Outside, discover multiple levels of outdoor living and entertaining spaces thoughtfully integrated into the natural surroundings, offering the perfect setting for relaxation, dining, and hosting gatherings year-round. Located within the sought-after Roslyn Pines community, residents have access to membership opportunities at the Roslyn Pines Swim and Tennis Club, featuring swimming, tennis, basketball, and pickleball amenities. A rare offering that combines contemporary design, exceptional scale, spectacular natural light, and resort-style living in one of Roslyn’s most desirable settings.

8 Verity Lane, Roslyn

$2,890,000

5 Beds ⋅ 4 Baths ⋅ 1015799 MLS

Nestled in the prestigious Village of East Hills and located within the highly acclaimed Roslyn School District, this exceptional Center Hall Colonial, built in 2011, offers luxurious living with timeless elegance and modern comfort. Featuring 5 bedrooms and 4 full bathrooms, including a desirable first-floor bedroom and full bath, this residence is thoughtfully designed for today's lifestyle. A dramatic two-story entry foyer welcomes you into an expansive open floor plan, highlighted by soaring ceilings, oversized windows, and abundant natural sunlight from its coveted south-facing exposure. The spectacular two-story family room serves as the heart of the home, creating a grand yet inviting space for everyday living and entertaining. The gourmet chef's kitchen is equipped with premium finishes and appliances, complemented by a spacious breakfast area. Elegant French doors open directly to the backyard, seamlessly blending indoor and outdoor living. Situated on an oversized 18,000+ sq. ft. property, the home enjoys beautiful open views, exceptional privacy, and a circular driveway that enhances both curb appeal and convenience.

245 Harbor Hill Road, Roslyn

$1,899,000

5 Beds ⋅ 4 Baths ⋅ 1009028 MLS

Steeped in history and reimagined with a designer’s eye, this 1918 masterpiece offers a rare blend of timeless Roslyn charm and high-end modern luxury. Tucked away on a quiet, leafy cul-de-sac, this home isn’t just a place to live—it’s a curated experience where every finish and fixture has been thoughtfully selected by its designer-owner. The heart of the home is a brilliant white chef’s kitchen, complete with gas cooking and a seamless flow into both the dining room and den. It’s a space built for hosting, whether you’re throwing a lively dinner party or enjoying a quiet morning coffee. French doors beckon you toward the classic front porch, while another set opens to a rear deck, blurring the lines between the elegant interiors and the lush, private grounds. While the home honors its historic roots with stunning wood floors and classic proportions, a 2018 expansion brought it firmly into the modern era. The addition of a sprawling main-level primary ensuite serves as a true sanctuary, featuring a private deck for moments of total serenity. Upstairs, four generous bedrooms and two full baths provide ample space for family or guests, complemented by the convenience of a first-floor laundry room and a stylish powder room. The property continues to impress outside. Beyond the main house sits a detached one-car garage with a surprise: a versatile upper-level space perfectly suited for a quiet home office, a yoga studio, or a private gym. Located just minutes from the vibrant shopping and dining of Roslyn Village and situated within the prestigious Roslyn School District, this is a one-of-a-kind opportunity to own a piece of local history that has been loved, polished, and perfected. It’s more than a home; it’s a work of art waiting for its next chapter.

42 Hillcrest Avenue, Roslyn

$3,098,000

5 Beds ⋅ 5 Baths ⋅ 996187 MLS

LOCATION! LOCATION! LOCATION WITH WATER VIEWS! THE ONE & ONLY! Set within one of Roslyn’s premier locations, this fully renovated residence captures breathtaking water views and offers a sophisticated blend of modern design, luxury, and comfort. Thoughtfully reimagined with exceptional attention to detail, the home is filled with natural light and features seamless indoor-outdoor living throughout. Designed for both elegant entertaining and everyday enjoyment, the beautifully landscaped property showcases a stunning brick patio, in-inground pool, and serene outdoor spaces overlooking the water- creating an extraordinary setting for relaxing or hosting guests. The interior offers expansive principal rooms including a spacious living room, formal dining room, and an inviting den with a wood-burning fireplace and direct access to the backyard. The designer eat-in kitchen serves as the heart of the home, featuring a dramatic oversized island with seating, premium finishes, and captivating water views. The luxurious primary suite boasts cathedral ceilings and a beautifully appointed spa-inspired bath. A beautifully finished walk-out lower level offers an additional bedroom and full bath, opening directly to the patio and backyard with stunning water vistas. Additional highlights include radiant heated floors and a two-car garage. Ideally located near premier shopping, fine dining, major highways, the LIRR, and within the Roslyn School District, this exceptional home offers luxury, comfort, and convenience in an extraordinary setting. Port Washington Train Sticker.

52 Woodland Road, Roslyn

$2,168,000

5 Beds ⋅ 4 Baths ⋅ 989484 MLS

A rare find in the prestigious Herricks School District. Tucked at the end of a quiet cul-de-sac in the coveted Beechwood neighborhood, this sun-filled contemporary delivers the privacy and space discerning buyers seek in Roslyn. Set on nearly half an acre, the home is designed for both everyday living and effortless entertaining. The main level features a formal living room, a dining room, and an open kitchen that flows seamlessly into the den. A first floor bedroom and full bathroom offer flexible living options. A dramatic open-to-below element adds architectural distinction and floods the interior with natural light. Upstairs, the generous primary en suite includes a dressing area and two closets. Three additional bedrooms and a full bathroom round out the upper level. Modern upgrades include a dedicated Tesla charging station, adding convenience for the eco-conscious driver. Outside, an updated deck with solarium creates a true outdoor retreat on a beautifully proportioned, private lot. Five bedrooms. Three and a half bathrooms. Herricks School District. Easy access to major highways, LIRR, library, shopping, and dining.

11 Bonnie Lynn Court, Roslyn

$1,445,000

5 Beds ⋅ 3 Baths ⋅ 987826 MLS

Roslyn, Flower Hill 5 Bedroom, 3 Bath Sprawling Ranch on picturesque cul-de-sac 1/3 acre. Featuring an Eat-in Kitchen with Stainless Steel Appliances, entertainment Den with fireplace, primary suite with private bath, Enjoy outdoor living on wrap around deck, sticker to Port Washington train station, Americana Shopping and Christopher Morley Park.

9 Oakwood Circle, Roslyn

$2,600,000

5 Beds ⋅ 6 Baths ⋅ 985081 MLS

Set in one of Long Island’s most sought-after communities, this fully renovated Roslyn colonial delivers the kind of craftsmanship and layout that’s genuinely hard to find. 5 bedrooms, 5 full baths and 1 half bath. A floor plan that works as well for everyday living as it does for entertaining. The first floor sets the tone immediately — custom millwork, high-end finishes by every trade, and an open layout that feels both expansive and warm. A fireplace anchors the living space, and the flow between rooms makes this home as comfortable for a quiet evening as it is for a full house. Rare for a colonial of this style, the first floor also offers bedroom accommodations — a versatile feature that adapts to whatever life calls for. The kitchen is the centerpiece. Premier appliances, quality cabinetry, and a double waterfall quartz island that comfortably seats multiple guests — it’s the kind of space that draws people in and keeps them there. Whether you’re hosting a dinner party or a quiet Sunday morning, this kitchen performs. Upstairs, three spacious bedrooms each with generous closet space and 3 full baths. The primary suite commands the floor — enter through double doors to find a dedicated seating area, a spa-caliber bathroom, and a large spacious closet with room for two. Outside, a large lot fully enclosed by white PVC fencing gives you a blank canvas: pool, patio, outdoor kitchen — the space is there, the vision is yours. Move-in ready. Nothing to do but arrive

2 Pine Drive S, Roslyn

$2,388,000

5 Beds ⋅ 6 Baths ⋅ 983710 MLS

Welcome to 16 Mackay Way, a beautifully maintained residence nestled in one of Roslyn’s most desirable and serene neighborhoods. This elegant home offers the perfect blend of comfort, functionality, and timeless charm. Featuring a spacious and sun-filled layout, the home boasts generously sized living areas, gleaming hardwood floors, and abundant natural light throughout. The inviting living room flows seamlessly into a formal dining area—ideal for entertaining guests or hosting family gatherings.The eat-in kitchen offers ample cabinetry and workspace, perfect for everyday living and culinary enjoyment. Multiple well-proportioned bedrooms provide comfort and privacy, while the bathrooms are tastefully designed to accommodate modern living. Set on a lovely property with a private backyard, this home is ideal for outdoor relaxation, gardening, or entertaining. Conveniently located near shopping, dining, parks, and major transportation, offering easy access to everything Roslyn has to offer. A wonderful opportunity to own a home in a prime location—don’t miss it! A Must See

16 Mackay Way, Roslyn

$1,708,000

5 Beds ⋅ 5 Baths ⋅ 969786 MLS

Stunning Hi-Ranch in East Hills, Roslyn! Set on .35 acres, this beautifully maintained home offers 5 spacious bedrooms and 4.5 baths. The main level welcomes you with an inviting entry foyer featuring a coat closet and powder room. Just ahead, a sun-filled family room boasts soaring ceilings, a skylight, fireplace, and sliding doors that open directly to the backyard, along with stairs leading to the lower level. To the left of the foyer, you’ll find a generous living room with a fireplace and a separate formal dining room. These spaces are thoughtfully designed on split levels, creating an open yet distinct flow—perfect for both everyday living and entertaining. The large eat-in kitchen, accessible from both the dining room and foyer, is equipped with high-end appliances and granite countertops. It also features a bright breakfast area with a skylight and sliding doors that lead to the fenced backyard. To the right of the foyer are four well-proportioned bedrooms, including a primary suite with double-door entry, a private en-suite bath, and a walk-in closet. The three additional bedrooms are serviced by a full hall bath. The lower level is partially finished and offers additional living space, including an entertainment room, guest room, laundry room, and a full bath, along with access to the attached two-car garage. Located in the highly sought-after Roslyn School District and zoned for Harbor Hill Elementary, this home also includes membership to East Hills Park, offering pools, tennis courts, a fitness center, walking trails, and more. Conveniently situated near the LIRR, Long Island Expressway, shopping, dining, and parks. A wonderful opportunity to enjoy all that East Hills has to offer!

106 Woods Drive, Roslyn

Start Your Search

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.

5 Bedroom Roslyn Real Estate

Our website features the best real estate search for 5 bedroom properties available in Roslyn and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!