View All Latest Middletown 5000+ Sq. Ft. Properties for Sale

THE ULTIMATE PRIVATE RESORT. Handsome Colonial estate set on 2.73 acres along prestigious Navesink River Road, gracefully positioned nearly 250' from the street amidst lush, manicured grounds. The property is a true retreat, featuring a stunning pool and a private sport court--pickleball, anyone? Modern construction showcases high ceilings and an open, flowing floor plan enhanced by oversized windows with transoms, flooding the interiors with natural light. Designed for both entertaining and everyday living with a dramatic double-height entry and formal dining room complemented by a butler's pantry. The gourmet kitchen is thoughtfully appointed with a walk-in pantry, an oversized center island with seating, furniture-quality cabinetry, and professional-grade Viking appliances, all opening seamlessly to a spacious family room with a fireplace and direct access to the rear deck and grounds. Additional main-level highlights include a sun-filled front-to-back conservatory, a gracious living room with fireplace, and an executive-style office featuring custom built-ins and a coffered ceiling.Upstairs, the exceptional primary suite offers a serene retreat with a soaring vaulted ceiling, sitting area, walk-in closet, and a well-appointed bath with dual vanities, a separate shower, and a jetted tub. Generously sized secondary bedrooms provide ample closet space, while a walk-up third floor offers additional flexibility. A mudroom leads to the oversized three-car garage, and the lower level--with its high ceilings--presents an ideal opportunity for future finishing. The beautifully expansive property extends to Patterson Ave, perfect for easy-access biking or leisurely walks in one of Monmouth County's most picturesque settings. Conveniently located just minutes from Red Bank, area beaches, the NY Ferry, Garden State Parkway, NJ Transit, and more, this offering combines privacy, elegance, and accessibility in a truly special setting. Zip code is 07701.

423 Navesink River Road, Middletown

Listing courtesy of Berkshire Hathaway HomeServices Fox & Roach - Rumson. Contact:

$4,699,000

5 Beds ⋅ 8 Baths

Waterfront Oasis....This pristine custom shore colonial is set on 3.85 lush acres with lovingly tended gardens, secret hideaways and magnificent specimen trees. The property unfolds to a vista with breathtaking 180-degree panoramic views of the Navesink River to the Atlantic Ocean. The open and versatile floor plan includes two potential primary suites; one on the main level with extraordinary views of the river. The inviting great room with its soaring ceiling and gas fireplace is located off the kitchen. The breakfast nook captures the sunrises with its numerous windows. Upstairs, the private primary suite features a balcony, fireplace and luxurious bathroom and office area. Flexible floor plan offers rooms for guests, in-laws, gym or playroom. Riparian grant incl. SF is per tax.

942 Navesink River Road, Middletown

Listing courtesy of Heritage House Sotheby's International Realty. Contact:

$1,850,000

6 Beds ⋅ 7 Baths

Set within one of Lincroft's most coveted neighborhoods in 07738, welcome to 79 Cypress Neck Road, a private estate offering over an acre of property and more than 6,000 square feet of living space. This exceptional home delivers a rare combination of scale, functionality, and resort-style outdoor living. Ideally located just moments from the Garden State Parkway, this home offers convenient access for NYC commuting while maintaining the privacy and tranquility of a premier neighborhood setting. Just minutes from the Netflix Studios at Fort Monmouth, the location also benefits from one of the most significant developments in Monmouth County, adding long-term value and convenience. The recently renovated kitchen is a jaw dropper and is designed for both everyday living and entertainin featuring premium Sub-Zero appliances including a refrigerator, freezer, and wine fridge, along with Viking appliances, double farmhouse sinks, dual dishwashers, and an InstaHot water dispenser. The space flows seamlessly into the main living and dining areas and is truly the heart of the home. A grand two-story family room filled with natural light showcases oversized windows, Pella French doors, custom built-ins, double chandeliers, intricate crown molding, and a central gas fireplace. The layout creates a seamless connection to the outdoor living spaces, enhancing the home's indoor-outdoor lifestyle. The expansive floor plan includes a luxurious primary suite with vaulted ceilings, multiple walk-in closets, and a spa-inspired mostly marble bath with soaking tub and oversized shower. Generously sized secondary bedrooms include a princess suite with private en-suite bath, while a first-floor guest suite offers flexibility for multigenerational living. Interior highlights include oak hardwood floors throughout, three fireplaces, including wood-burning fireplaces in the office and formal living and dining room, a dedicated home office, sunroom, and formal dining room. The backyard is a true standout feature, anchored by a 20 by 40 heated saltwater pool with updated liner and heater in 2024. Multi-tiered paver patios, manicured landscaping, a fenced yard, and a half-court basketball area create a private, resort-style setting ideal for entertaining or everyday enjoyment. A newly finished walk-out lower level with natural light and a half bath provides additional flexible space for a gym, media room, or even guest suite. Recent updates and modern systems include all new HVAC equipment in January 2026, new attic insulation in January 2026, 4-zone climate control with NEST thermostats, tankless water heater in 2024, Bosch alarm system in 2024, partial home generator, new lawn irrigation system in 2024, and smart lighting throughout. Located within the highly regarded Middletown Township Public School District and zoned for Middletown High School South, this property also benefits from access to one of the area's most sought-after school systems. Homes offering this level of space, land, and outdoor amenities rarely become available at this price point. Don't wait! Make your appointment today...

79 Cypress Neck Road, Middletown

Listing courtesy of Coldwell Banker Realty. Contact: 732-245-0340

Selling Office: Douglas Elliman of NJ LLC.

$1,750,000

6 Beds ⋅ 6 Baths

Spectacular Multi Generational Custom Colonial. A true architectural delight located at the end of the cul de sac on a lovely street. Thoughtfully large room dimensions and soaring ceiling heights boasting architectural details and moldings in nearly every room. True custom craftsmanship is apparent on every level of this quality home. The kitchen offers furniture quality cabinets, granite, center island, huge pantry and high end appliances-The great room offers a wet bar w wine refrigerator, fireplace, tray ceiling w/ mood lighting and french doors to the blue stone patio. First level bedroom suite with private bathroom and its own living room for long stay guests. Upstairs has 9 ft ceilings and all en suite bedrooms each with fabulous bathrooms & ample closets PLUS so much m Master bathroom offers radiant floors, double sinks, steam shower with multiple shower heads, a separate 2 person jacuzzi style tub PLUS a secret mini refrigerator and hideaway coffee bar. Master has a terrace overlooking the rear yard plus a Huge master walk in closet w/hard wood floors under carpet. Heated bathroom floors in all bathrooms-So many upgrades to this home inside and out-Seller including chandelier and theres an automatic winch, Home also has central vacuum even in the attic! Come See the VALUE Sellers have plans for a pool to be shared.

41 Marlpit Place, Middletown

Listing courtesy of O'Brien Realty, LLC. Contact:

Selling Office: Heritage House Sotheby's International Realty.

$1,700,000

7 Beds ⋅ 6 Baths

Beyond a stately wrought iron gate, this extraordinary Italian Villa-style estate stands as Monmouth County's finest remaining example of its kind. Perched atop a hill, the home boasts a grand arched double-door entrance leading to a marble foyer, where a hand-carved newel post and sweeping staircase set the tone for its unmatched craftsmanship. Towering 11-foot ceilings, intricate woodwork, and six fireplaces add to its timeless appeal. A richly paneled oak library, connected by a pocket door to a one-of-a-kind built-in bar room, offers a rare blend of elegance and charm. Outside, a wraparound veranda captures picturesque views of the tennis court and sprawling three-acre property, complete with a pool, gazebo, and a three-bay garage with a character-filled caretaker's apartment above. Thoughtfully preserved, the side porch was completely rebuilt in February 2025. A once-in-a-lifetime opportunity to own a truly unique architectural masterpiece.

600 Oak Hill Road, Middletown

Listing courtesy of Berkshire Hathaway HomeServices Fox & Roach - Rumson. Contact:

Selling Office: Keller Williams Realty Spring Lake.

$2,750,000

5 Beds ⋅ 5 Baths

Navesink Riverfront Nantucket Style Colonial w/ 150' Ipe dock artfully designed by Anderson & Campanella is a true masterpiece! This well-thought-out home features high ceilings & an abundance of windows, flooding the space with natural light & offering stunning views of the Navesink River. The brilliant open floor plan includes a gourmet kitchen that opens to a great room w/ oversized windows & transoms throughout. Custom built-ins & high end millwork, hardwood flooring & great versatility throughout. Enjoy beautiful baths, a luxurious primary w/ oversized WIC, a walk-out finished lower level w/ covered porch & more! 16,000lb electric lift & bubbler system @ dock. A must see to truly appreciate an endless list of amenities. Minutes from the NY Ferry and train. Zip 07701.

136 Conover Lane, Middletown

Listing courtesy of Berkshire Hathaway HomeServices Fox & Roach - Rumson. Contact:

Selling Office: Berkshire Hathaway HomeServices Fox & Roach - Rumson.

$999,999

4 Beds ⋅ 3 Baths

Discover the epitome of luxury living in this exceptional home offers a rare custom ranch design, making it perfect for entertaining and providing a private oasis. As you step inside, prepare to be amazed by the stunning features and ambiance. The sunken living room with a two-way stone fireplace greets you upon entering the foyer. What's more, there's an indoor pool visible from the front door, accessible from multiple points throughout the house. This exquisite 4-bedroom, 3-bathroom residence boasts a unique layout, including a custom formal family room and dining room. Recessed lighting and crown molding add elegance to the space. Enjoy a dedicated theater room for your favorite sports games or movies, a gaming room, or a tranquil getaway with soundproofing. The eat-in kitchen is a chef's dream, featuring granite countertops, stainless steel appliances, a Kenmore Elite refrigerator, cherry cabinets, and a generously sized center island. Moving towards the living quarters, you'll discover beautifully appointed bedrooms with custom California closets. The master ensuite even has a private entrance to the pool area, where a private sauna awaits for ultimate relaxation. In addition, this home is equipped with a Generac generator, ensuring uninterrupted power supply during outages. And that's not all! There's also a bonus office space that can easily be converted into a fifth bedroom, providing flexible living arrangements to suit your needs. Step into the backyard, which offers a secluded gazebo, four seasons awning patio area for lounging and dining, ample outdoor spaces, and even a horseshoe court! Completing the property is a two-car garage, a spacious driveway, and a location near major highways, shopping centers, public transportation, and restaurants. Prepare to be awestruck by this truly remarkable home. Don't miss your chanceschedule your appointment today and witness its splendor firsthand!

86 Deepdale Drive, Middletown

Listing courtesy of EXP Realty. Contact:

Selling Office: 1-2-3 REALTORS.

$6,100,000

8 Beds ⋅ 11 Baths

THE ULTIMATE TROPHY PROPERTY. Gated entry leads to this iconic estate artfully set on 17+ acres sprawling 3 separate lots w/ over 1,400' OF FRONTAGE ON THE NAVESINK RIVER & RIPARIAN GRANT-PARADISE FOUND! Mature privacy plantings, manicured grounds & the most BREATHTAKING VIEWS YOU'VE EVER SEEN! Of special note: a newer private Ipe dock w/ boat lift, gorgeous infinity pool overlooking river, tennis court, garage parking for up to 9 cars, a guest house, 2 care-taker cottages & a 5-stall barn w/ tack house for the equine enthusiast. Expansive main res. w/ views from nearly every room offers endless possibilities w/ character intact & many thoughtful updates. Mins to Huber/Hartshorne & Ferry & beautiful beaches. A RARE OPPORTUNITY.

700 Navesink River Road, Middletown

Listing courtesy of Berkshire Hathaway HomeServices Fox & Roach - Rumson. Contact:

Selling Office: Orrico Realty.

$2,415,062

5 Beds ⋅ 5 Baths

The good life awaits the discerning buyer at the NEW CONSTRUCTION IN HIDDENWELL ESTATES ! SENSATIONAL MODERN SEASHORE COLONIAL on a cul de sac that meanders to Shadow Lake. Custom millwork and high end finishes & a fantastic open floor plan w/ high ceilings & hardwood floors throughout. Top of the line gourmet kitchen w/ custom cabinetry & Thermador appliances, gorgeous baths w/ designer tile. mud room w/ custom built-ins , FINISHED BASEMENT w/ HIGH CEILINGS. It all starts with your imagination. Come see.

4 Bucchop Lane, Middletown

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Coldwell Banker Realty.

Start Your Search

5000+ Sq. Ft. Middletown Real Estate

Our website features the best real estate search for 5000+ sq. ft. properties available in Middletown 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!