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

$959,000

4 Beds ⋅ 4 Baths ⋅ 1048249 MLS

Welcome to 51 Jordan Dr, an impressive Contemporary Colonial showcasing distinctive architectural details, generous living space, and exceptional curb appeal. A circular driveway leads to a two-car garage with two garage doors, creating a welcoming approach to this beautifully appointed residence. Inside, soaring cathedral ceilings and a natural gas fireplace create an inviting focal point in the living room, while the Mediterranean-inspired gourmet kitchen is designed for both functionality and style. A formal dining room and convenient main-level business office add versatility for everyday living. Upstairs, the spacious primary suite features an elegant private bath, complemented by three additional generously sized bedrooms and a hall bathroom. The finished lower level offers even more living space with a full bathroom, separate outside entrance, and home theater complete with seating. Step outside to a true backyard retreat featuring a patio, built-in barbecue, and pool, creating an ideal setting for outdoor entertaining and summer enjoyment. Conveniently located near major highways, shopping, and everyday amenities, this exceptional Medford home offers an appealing combination of style, space, comfort, and versatility. Please note pool needs a new liner.

51 Jordan Drive, Medford

$704,900

4 Beds ⋅ 4 Baths ⋅ 1041838 MLS

Welcome to 16 Jacobsen Court, a spacious Colonial tucked away on a quiet cul-de-sac and situated on approximately 1.18 acres. Offering approximately 3,200 square feet of above-grade living space, this home features 4 bedrooms, 2.5 baths, a formal dining room, living room, den with fireplace, kitchen, first-floor laundry and an attached 2-car garage. Upstairs you'll find a primary bedroom with private bath, three additional bedrooms and a full hall bath. The large property provides plenty of outdoor space and privacy. The finished basement is currently configured as a 2-bedroom apartment with a kitchen, living area, full bath and outside entrance. There is no C/O for the basement apartment, and buyers should independently verify requirements for the existing use and configuration. The property also features an in-ground pool that is currently non-functioning and in need of repair. This home offers tremendous potential for a buyer looking for a large home, substantial property and additional finished lower-level space. Property is being sold as-is.

16 Jacobsen Court, Medford

$679,990

4 Beds ⋅ 3 Baths ⋅ 1041110 MLS

Welcome to this spacious 4-bedroom, 3-bathroom home set on approximately 3/4 acres, offering an exceptional combination of space, privacy, and tranquility—along with very low property taxes. The large front yard and wraparound porch create a welcoming first impression while providing excellent privacy from the street. Inside, the home is filled with natural light and features a spacious layout with a formal dining room and comfortable living room. The oversized primary suite is a true retreat, featuring a huge bedroom, generous walk-in closet, and a beautiful en-suite bathroom complete with a jacuzzi tub, separate stand-up shower, and skylights that bring in an abundance of natural light. Just outside the primary bedroom is a large second-floor landing with endless possibilities. Create a private home office, den, reading room, sitting area, or simply a quiet place to relax and unwind away from the main living areas downstairs. This versatile space provides an additional area to enjoy without leaving the second-floor living space. A dedicated laundry room adds convenience, while the oversized attached 2-car garage and large driveway provide plenty of parking and storage. The true star of the property is the backyard. The expansive grounds create a serene and incredibly private outdoor retreat. The pool is tucked away in its own secluded section toward the rear of the property, offering a level of privacy that is hard to find. The large patio provides plenty of room for entertaining, relaxing, and enjoying summer days by the pool. The home offers an excellent opportunity for its next owner to update and personalize while enjoying generous living spaces, a remarkable primary suite, and a peaceful private setting. The property does need updating, but offers a solid foundation and tremendous potential. Located conveniently near major highways, shopping, dining, and everyday amenities, this home gives you the best of both worlds: a private, spacious property with easy access to everything you need.

187 Oak Street, Medford

$745,000

3 Beds ⋅ 3 Baths ⋅ 1040034 MLS

Welcome to 23 Greentree Drive! This spacious Colonial offers approximately 2,200 sq. ft. of living space and is situated on .69 of an acre. Features include a custom kitchen, approximately 3 years young which has quartz countertops, a stylish marble & ceramic backsplash, Large Center Island with room for seating, Porcelain tile flooring and recessed lighting throughout. Double door entrance leads into the primary bedroom that has it’s own Bathroom with soaking tub and walk-in closet. The home also has a 2-car garage, full unfinished basement, central air conditioning and gas heating with an updated hot water heater. Enjoy abundant natural light throughout, including a beautiful 2-bay window, some Pella Windows and Pella front door. Additional highlights include hardwood floors and a wood-burning fireplace in the den. Outside features a bi-level paver patio in rear with Slate bluestone steps. 40x20 irregular In-Ground Pool. The property goes back approx. 15 feet from where the fence is and belongs to this home and backs up to the Preserve. The chimney was repointed approximately 2 years ago, and the cesspool is located in the front of the property. A wonderful opportunity to call home.

23 Greentree 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

$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

$584,999

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! **BACK ON THE MARKET-Buyers financing fell through. No fault of the property.**

473 Long Island 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

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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.