Medford Homes with Pool

Welcome to Medford, New York – a hidden gem nestled in the heart of Suffolk County. Known for its charming suburban atmosphere, Medford offers a unique blend of tranquility and accessibility, making it an ideal location for families, young professionals, and retirees alike. With its lush parks, excellent schools, and a vibrant community spirit, Medford provides residents with a quality of life that’s hard to beat.

One of the standout features of this delightful town is the availability of homes with pools. Imagine stepping into your own backyard oasis during those warm summer months, where you can unwind, entertain guests, or simply enjoy a refreshing dip in your private pool. Homes in Medford with pools come in various styles and sizes, catering to diverse tastes and preferences. Whether you’re looking for a cozy ranch-style home or a more expansive multi-level property, you’ll find an array of options that perfectly suit your lifestyle.

Beyond the allure of private pools, Medford boasts a wealth of local amenities. From shopping centers to dining options, everything you need is just a stone’s throw away. Plus, with easy access to major highways and public transportation, commuting to nearby cities like New York and Long Island is a breeze.

In Medford, you’ll not only find a place to live but a community to thrive in. So why wait? Dive into the Medford lifestyle today and discover the perfect home with a pool that’s waiting just for you!

Newest Medford Homes with Pool

$699,990

4 Beds ⋅ 3 Baths ⋅ 1033489 MLS

Perfect home for a large family nestled on shy .75 acre property. Move in condition!! 6 year old roof, 2 year old CAC, New liner and plumbing for 16x44 in ground pool with vacuum, decking, cedar closet, redone kitchen and baths. Some new windows, Private back yard features play ground for children and a place for chickens!! Truly a gem!!

8 Virginia Drive, Medford

$699,999

3 Beds ⋅ 2 Baths ⋅ 1031946 MLS

Welcome to this beautifully maintained Colonial in the heart of Medford! This inviting 3-bedroom, 1.5-bath home offers the perfect blend of comfort and outdoor living. The spacious layout is ideal for everyday living and entertaining, while the backyard is a true retreat featuring an in-ground swimming pool, expansive patio, covered outdoor entertaining area, and plenty of green space for gatherings or relaxation. Enjoy summer days poolside and evenings hosting family and friends in your private oasis. Conveniently located near parks, shopping, restaurants, schools, and major roadways, this home offers both tranquility and accessibility. Don’t miss this exceptional opportunity to own a home with resort-style outdoor amenities

7 Sprat Street, Medford

$849,000

4 Beds ⋅ 3 Baths ⋅ 1027490 MLS

Spacious 2200 sq ft contemporary home on a rare 1+ acre parcel, offering 4 bedrooms, primary ensuite, plus 1.5 additional baths, updated eat-in-kitchen and an attached 2-car garage all on a private cul-de-sac. The living room features a fireplace and plenty of natural light. The functional floorplan offers generous living area and plenty of room for everyday living and guest entertaining alike. Step outside to a well-manicured quiet, private backyard featuring a pristine in-ground saltwater pool, ideal for summer entertaining, outdoor dining or simply enjoying your home. A spacious full basement provides excellent storage and endless possibilities for recreation space, home gym, or home office. Conveniently located on one of Medford's most desirable streets, this home offers easy access to shopping, parks, and schools. This is the perfect place to call home!

3 Woodhollow Court, Medford

$759,000

5 Beds ⋅ 2 Baths ⋅ 1028067 MLS

Welcome to this beautifully renovated 4-5 bedroom home set on a lush 1/3-acre property in Medford. The true highlight is the resort-style backyard featuring an in-ground pool surrounded by a brick patio, a large entertainment deck with outdoor bar and BBQ area, and a covered metal canopy—perfect for hosting family and friends rain or shine. Inside, you'll find a stunning new kitchen with white shaker cabinets, quartz countertops, and newer appliances (approximately 1 year old), along with a spacious great room featuring a fireplace. Fresh paint, new carpeting, updated railings, and two fully renovated bathrooms make this home completely move-in ready. Additional features include a bright sunroom with French doors overlooking the pool, a flexible 5th bedroom or home office, a partially finished basement with wet bar setup, commercial-grade dehumidifier, new HVAC system, restored backup boiler, circular driveway, and rare 50-amp RV hookup. 200 amp house panel. A rare opportunity to own a fully updated home with an incredible backyard built for entertaining.

299 Mount Vernon Avenue, Medford

$630,000

4 Beds ⋅ 3 Baths ⋅ 1026640 MLS

Turnkey 4 Bedroom, 3 Full Bath Hi-Ranch Offering Stylish Updates Throughout. Features Include a Beautifully Updated Kitchen with New Appliances, Refinished Wood Floors, a Living Room with a Wood-Burning Fireplace with Insert and New Accent Wall, and a New Mudroom. Additional Improvements Include a New Front Stoop, Paver Walkway, Paver Patio, and Restored Fire Pit. Roof Replaced in 2015, Central Air, Solar Panels, and an Exterior Entrance Offering Potential for a Mother/Daughter Setup with Proper Permits. The Backyard Is an Outdoor Oasis Featuring a Heated Saltwater In-Ground Pool and Expansive Paver Patio, Perfect for Relaxing or Entertaining. Completely Updated and Move-In Ready!

234 Buffalo Avenue, Medford

$998,000

7 Beds ⋅ 4 Baths ⋅ 1027815 MLS

Welcome to an extraordinary custom-built Colonial situated on an exceptionally rare full-acre property, offering an unmatched combination of space, versatility, and lifestyle. Whether you're searching for your forever home, a multi-generational living opportunity, or the perfect property for a business owner, tradesperson, or outdoor enthusiast, this one-of-a-kind residence presents an opportunity rarely found in today's market. From the moment you arrive, you'll appreciate the impressive 200-foot private driveway leading to an expansive parking area accommodating 20+ vehicles, in addition to the attached 1.5 car garage. There's ample room for work trucks, trailers, RVs, campers, boats, and recreational vehicles—making this an exceptional property for contractors, hobbyists, collectors, or anyone who values freedom and flexibility. The thoughtfully designed layout offers generous living space throughout. The first level features three spacious bedrooms, a full bath, direct garage access, and a separate rear entrance—ideal for extended family or a possible mother-daughter configuration with proper permits. Adding even more value is the home's full-footprint oversized basement with 8-foot ceilings and a separate exterior entrance with poured concrete stairs. This expansive lower level provides exceptional storage and endless possibilities for a home theater, gym, recreation room, workshop, office, or additional living space (with proper approvals). The upper level is the heart of the home. Soaring cathedral ceilings enhance the living room, dining room, and kitchen, while skylights and oversized windows flood the space with natural light. The spacious primary suite offers an oversized en-suite bath and abundant closet space, including walk-in closets. Step outside into your own private backyard oasis featuring a spectacular oversized in-ground pool surrounded by nearly 1,500 square feet of premium, like-new paver patio, creating a true country club setting for entertaining or everyday relaxation. A charming wooden gazebo offers endless possibilities as a future pool cabana, outdoor kitchen, entertainment pavilion, or cozy gathering space with an outdoor fireplace. Beyond the pool, the sprawling lawn provides room for virtually every outdoor activity imaginable. Located within the award-winning Longwood Central School District, you'll enjoy outstanding educational opportunities, youth sports leagues, beautiful parks, and an active community. Conveniently close to shopping, dining, major roadways, beaches, and everyday conveniences, this home offers the perfect balance of privacy, accessibility, and exceptional quality of life. Properties offering this much land, parking, recreational space, and versatility are extraordinarily rare. Whether you're envisioning your forever home, accommodating multiple generations, operating a home-based business, or simply enjoying room to grow, this property delivers possibilities few homes can match. Rare. Spacious. Versatile. One of a Kind. A truly exceptional opportunity to own one of the area's most distinctive properties, where extraordinary indoor living, resort-style outdoor amenities, an oversized basement with incredible potential, and an unbeatable location come together to create the lifestyle you've been dreaming of.

241 Middle Island Road, Medford

$669,000

6 Beds ⋅ 3 Baths ⋅ 1026382 MLS

Welcome to this spacious oversized ranch set on just shy of a half-acre (.46 acres) in a desirable street-to-street location. Offering exceptional indoor and outdoor living space, this home features 4 generously sized bedrooms on the main level, including a primary suite with its own private en-suite bath. New flooring has been installed in multiple bedrooms, adding a fresh and updated feel throughout. The heart of the home includes a recently refinished formal dining room highlighted by stylish accent walls, perfect for special occasions. Just beyond, you'll find a large den featuring a cozy wood-burning fireplace, creating a warm and inviting atmosphere year-round. Central air conditioning and a 200-amp electric service provide modern comfort and convenience. Downstairs, the finished basement with a separate outside entrance offers incredible flexibility for many needs. With the proper permits, the space has the potential to accommodate a 2-bedroom accessory apartment, presenting a unique opportunity for future potential rental income. This home has been thoughtfully maintained and updated, including a new roof with plywood replacement completed in 2022, all-new siding, and an updated cesspool that has been recently pumped, providing peace of mind for years to come. Step outside to your own private backyard retreat. The well-maintained above-ground pool features a liner that is only two years old along with a newer filter system. Surrounding the pool is an expansive deck that creates the ultimate setting for entertaining, relaxing, and enjoying summer days. The oversized yard offers endless possibilities. A rare double-gate entrance provides convenient access into the backyard for vehicles, trailers, boats, or additional recreational equipment, a valuable feature made even more desirable by the property's unique street-to-street lot configuration.

1010 Sipp Avenue, Medford

$599,999

3 Beds ⋅ 2 Baths ⋅ 1023940 MLS

Welcome to this beautifully maintained ranch that perfectly blends comfort, efficiency, and incredible potential. This move-in-ready home features three generously sized bedrooms and 1.5 bathrooms, including a recently updated half bath. The bright eat-in kitchen is equipped with Energy Star appliances, with the oven and dishwasher replaced approximately two years ago. An energy-efficient gas-powered Navien heating system, installed about five years ago, provides year-round comfort and peace of mind. Step outside to a fully fenced backyard with mostly new fencing, offering the perfect setting for entertaining, relaxing, or enjoying outdoor activities. An above-ground pool is included as a gift. The full basement with high ceilings offers exceptional versatility and endless possibilities. Previously configured as a permitted two-bedroom accessory apartment, it still features existing plumbing and a separate outside entrance, presenting an excellent opportunity for future use, subject to applicable permits and local regulations. Conveniently located near shopping, restaurants, public transportation, bus lines, and the Long Island Railroad, this home offers the ideal combination of location, value, and flexibility. Whether you're looking for your forever home or one with room to grow, this property is a rare opportunity you won't want to miss. Schedule your private showing today!

473 Long Island Avenue, Medford

$549,000

3 Beds ⋅ 2 Baths ⋅ 1022499 MLS

Nestled in the desirable Eagle Estates neighborhood of Medford, this well-maintained 3-bedroom, 2-bath raised ranch offers the perfect blend of comfort, functionality, and outdoor living. Hardwood floors flow throughout the home, creating a warm and inviting atmosphere. The kitchen provides direct access to a spacious deck overlooking the backyard—ideal for morning coffee, outdoor dining, and entertaining. Step outside to your private backyard featuring an in-ground saltwater pool, perfect for enjoying summer days with family and friends. Additional highlights include energy-efficient mini-split systems for cooling and owned Tesla solar panels, offering the benefits of renewable energy with no lease or monthly payments. Conveniently located near parks, shopping, dining, and major roadways, this Eagle Estates home presents a wonderful opportunity to enjoy both comfort and convenience.

3010 Sipp Avenue, Medford

$899,000

6 Beds ⋅ 3 Baths ⋅ 1021990 MLS

Welcome to 208 Newburgh Avenue, a spacious Colonial offering approximately 4,000 square feet of beautifully updated living space. This impressive home features 6 bedrooms and 3 full bathrooms, including 4 bedrooms on the second level and 2 bedrooms on the main level, providing a versatile floor plan for today’s lifestyle. The renovated eat-in kitchen showcases granite counter tops, stainless steel appliances, custom cabinetry, and a large center island with seating, flowing seamlessly into the main living area for effortless everyday living and entertaining. The expansive primary suite offers generous space, while updated bathrooms, hardwood/laminate flooring, recessed lighting, and abundant natural light enhance the home’s appeal throughout. Additional finished living space provides flexibility for a recreation room, home office, gym, or hobby area. Step outside to a fully fenced backyard featuring a spacious deck, above-ground pool, and expansive lawn, creating an ideal setting for relaxing or entertaining. Conveniently located near shopping, restaurants, parks, major roadways, and the Long Island Rail Road, this move-in-ready Colonial offers exceptional space, modern updates, and endless possibilities. Tons of room for mom!

208 Newburgh Avenue, Medford

$1,150,000

4 Beds ⋅ 3 Baths ⋅ 1014732 MLS

Welcome to 52 Elmhurst Avenue — a truly one-of-a-kind custom-built estate offering luxury, comfort, and endless possibilities for entertaining and extended family living. This magnificent home features 4 spacious bedrooms and 2.5 beautifully appointed bathrooms. From the moment you enter, you’ll be impressed by the custom wood flooring, elegant craftsmanship, and thoughtfully designed layout. The gourmet chef’s kitchen is the heart of the home, complete with high-end finishes and open flow into the inviting living spaces. A cozy fireplace creates the perfect gathering spot in the large family room while the dining room and living room allow for plenty of space to entertain all of your friends and family. Additional highlights include a huge garage and a full basement with impressive 8-foot ceilings. Designed with flexibility in mind, the lower level offers the potential for two additional bedrooms, a large kitchen, full bathroom, spacious living room, and outside entrance—making it ideal for extended family, guests, or multigenerational living. Upstairs, you will find the luxurious primary suite offering a spa-inspired bathroom along with 3 additional well-appointed bedrooms, a full bathroom with double vanity and a laundry room. Step outside and discover your own private resort. The oversized, secluded lot has a spectacular backyard that was built for entertaining; featuring a sparkling inground pool, custom gazebos, and multiple areas for relaxing and hosting unforgettable gatherings. As an added bonus, this property includes an additional half-acre parcel located directly behind the home, offering endless possibilities. Whether you envision a horse stable, private recreational space, gardens, or simply enjoying the added privacy, this unique feature sets this property apart from the rest. Nestled at the end of a quiet cul-de-sac on an exceptionally private block, this remarkable residence offers the perfect blend of luxury, tranquility, and room to grow. Imagine years of creating memories, entertaining loved ones, and enjoying everything you’ve ever wanted—all in one extraordinary place. Welcome home.

52 Elmhurst Avenue, Medford

$585,000

3 Beds ⋅ 1 Baths ⋅ 994973 MLS

Welcome to your dream home at 88 Matsunaye Dr in the heart of Medford—where comfort, style, and location come together perfectly. This beautifully maintained residence is nestled in a desirable neighborhood just moments from everything Long Island living has to offer. The doors open up to a bright and spacious living room with soaring vaulted ceilings that create an open, airy feel—perfect for entertaining guests or enjoying cozy nights at home. The updated kitchen is truly the centerpiece, featuring sleek quartz countertops, stainless steel appliances, and elegant soft-closing cabinetry. The eat-in kitchen flows seamlessly to sliding glass doors that lead to your private backyard oasis—ideal for summer BBQs, outdoor dining, or simply relaxing by your in-ground pool. This beauty offers 3 comfortable bedrooms, a full bathroom, central air conditioning, an in-unit washer and dryer, and the convenience of an attached garage. The beautifully maintained grounds provide both curb appeal and privacy, making this home as inviting on the outside as it is inside. Location is everything—and this home delivers. You’re just minutes from the Long Island Expressway (I-495), making commuting a breeze, and only about 10 minutes to Stony Brook University and Stony Brook Hospital. The Ronkonkoma Train Station is approximately 15 minutes away, offering a direct route to New York City in about 1 hour to 1 hour and 20 minutes. Enjoy the charm and lifestyle of Port Jefferson Village just 20 minutes away, where you’ll find waterfront dining, boutique shopping, vibrant nightlife, and ferry access to Connecticut. With close proximity to shopping, parks, schools, and all major conveniences, this home truly has it all. Don’t miss your opportunity to own this incredible property—schedule your private showing today before it’s gone. Your dream home awaits!!

88 Matsunaye Drive, Medford

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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.