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$1,350,000
8 Beds ⋅ 4 Baths
Welcome to 228 Red Hill Road, located in the highly sought-after Oak Hill section of Middletown. Set on over 1.5 acres, this true mother-daughter home offers a rare opportunity to create the property you've always envisioned. Whether you're searching for a multi-generational home, a private compound, room for a farm, or simply the chance to renovate and make it your own, the possibilities here are endless. Expansive parcels like this are becoming increasingly rare--they're not making any more land. Perfectly positioned just minutes from the Garden State Parkway, Jersey Shore beaches, NYC ferry, train, and bus transportation, top-rated parks, shopping, and dining, this home offers the perfect balance of privacy and convenience. Enjoy the unmatched lifestyle that makes Middletown one of Monmouth County's most desirable places to call home. Bring your vision and transform 228 Red Hill Road into the home you've always dreamed of.

228 Red Hill Road, Middletown

Listing courtesy of EXP Realty. Contact:

$1,095,000
6 Beds ⋅ 4 Baths
One-of-a-kind, exceptional Oak Hill ranch! 6 bedrooms, 3.5 baths and multiple entertaining spaces. Upper level offers 3 bedrooms and 2.5 baths, a renovated kitchen with granite countertops, stainless steel appliances and woodburning fireplace, hardwood/ceramic floors, generous closet spaces, serene paver patio and a private expansive deck! Full walkout lower level, with separate entrance has 3 bedrooms, full bath, vintage kitchette and oversized familyroom/den/bar area. Neutral colors and loads of light on both levels. Anderson windows. Multigenerational living opportunities. Low maintenance yard and whole house generator. Incredibly convenient to GSP, train, ferry, New Jersey beaches, Monmouth County parks and Netflix. Middletown HS South. Relax in your own private, hilltop retreat!

200 Pelican Road, Middletown

Listing courtesy of Coldwell Banker Realty. Contact: 908-601-3363
$925,000
6 Beds ⋅ 6 Baths
Two family duplex with strong icome potential.Each unit offers 3 bedrooms and 2.5 bath with practical layouts and separate entrances. Fully rented with long term tenants. Property has the ability to be subdivided creating an opportunity to increase overall market value in addition to rental income. Features include fenced in yard, full basement ,private drivways and garage. Minutes to NYC ferry and train.

419-421 Main Street, Middletown

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

Selling Office: Keller Williams Realty Central Monmouth.

$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.

$1,525,000
6 Beds ⋅ 5 Baths
Spectacular best describes this stunning Center Hall Colonial located in highly desirable Chapel Hill! From the moment you drive through the stately columns and into the circular driveway, you'll know this home is something special — and what awaits inside will truly impress.This meticulous home is filled with warmth, charm, and character throughout. The spacious main level features a grand two-story foyer, elegant living & dining rooms with crown molding, hardwood floors, and plantation shutters. The inviting family room offers a cozy fireplace, while the gorgeous gourmet kitchen will delight any chef — complete with custom cabinetry, granite countertops, a center island, & top-of-the-line Viking double oven with 6-burner cooktop and hood. A bright breakfast area with vaulted ceiling powder room, and mudroom complete the first floor. Upstairs, you'll find, a large open foyer, four generous bedrooms, two full baths, and a convenient laundry room. The primary suite includes a fireplace, walk-in closet, and a newly remodeled spa-like bath with a classic clawfoot tub & beautifully appointed shower. The finished third level offers incredible versatility ideal for an additional primary suite, in-law or teen suite, home office, or private retreat  featuring a living room, bedroom with skylights, hardwood floors, and a full bath. The walk-out lower level is designed for multi-generational living or guest space, with a living room, eat-in kitchen, bedroom, exercise or second bedroom, laundry area, and a full bath.Step outside to your own backyard paradise  complete with a Trex deck, newly refinished heated inground fiberglass pool with hot tub spa and waterfall, surrounded by serene privacy and lush landscaping. Additional highlights include a whole-house generator and an oversized three-car heated garage with storage above that can easily be finished. This exceptional property truly offers it all  space, style, and sophistication  in one of Middletown's most sought-after neighborhoods. This home is sure to please!

152 Sleepy Hollow Road, Middletown

Listing courtesy of RE/MAX Welcome Home. Contact:

Selling Office: RE/MAX Homeland Realtors.

$1,855,000
6 Beds ⋅ 4 Baths
This is a coming soon listing. Showings begin 9/21. One of the finest properties in Middletown's coveted Oak Hill neighborhood, this stately 4,000 sq. ft. center-hall colonial (plus a finished basement) sits proudly at the head of a quiet cul-de-sac on 1.5 acres of beautiful level land. This turnkey residence offers six spacious bedrooms and four full bathrooms, with no detail overlooked. A double door entry opens to a dramatic two-story foyer that sets the tone for the custom millwork and thoughtful finishes throughout. The expansive open-concept kitchen is a true entertainer's dream, complete with quartz countertops, stainless steel appliances, a Kohler farmhouse sink, and an additional prep sink, all flowing seamlessly into the coffered ceiling family room with hardwood oak flooring. The cathedral-ceiling living room is enhanced by skylights and custom built-ins, creating a bright and inviting space, while the wood-paneled dining room offers warmth and sophistication for formal gatherings. Custom marble, porcelain, and ceramic tile can be found throughout the home, elevating its design with timeless elegance.The expansive primary suite features double walk-in closets and a luxurious bathroom retreat with cathedral ceiling, skylight, radiant heated floors, and custom marble tile work. The spa-like bath is complete with a Restoration Hardware double vanity, oversized custom shower, and a stand-alone soaking tub. A wood-paneled hallway leads to an additional custom-tiled bathroom with a double vanity and two linen closets, serving three generously sized bedrooms with detailed millwork. The fully finished walk-out basement offers high ceilings, a private bedroom suite with a full bath, marble tile flooring, subway-tiled shower, and marble mosaic finishes. Two separate walkouts provide access to the three-car garage and the resort-style backyard, which boasts a large wood deck, oversized paver patio, and a 42,000+ gallon Sylvan in-ground pool with a custom PVC pergola. Additional highlights include a brand new fully asphalted circular driveway, a spacious three-car garage, and professionally designed landscaping with specimen tree plantings. 3 zone a/c and multi zone hot water baseboard heating. Welcome to your private Oak Hill mini estate! Middletown South schools!

20 Cormorant Drive, Middletown

Listing courtesy of Melrose Realty, LLC. Contact:

Selling Office: JM Properties NJ Inc.

$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.

$1,175,000
6 Beds ⋅ 4 Baths
**HIGHEST & BEST DUE 6/5 at 3:00** Situated on a lush corner lot in a highly desirable neighborhood, this exceptional 6 bedroom, 3500+ sq. ft residence offers some truly unique features starting w/ the coveted AGA Cooker. A true chef's delight, this high-end appliance is ideal for those who love to cook & entertain or simply enjoy the warmth & cozy feel an AGA stove brings to a home. Grow your own food in the organic garden which has been lovingly curated for years & surrounded by fruit trees including generous peach trees. This property truly supports a farm to table experience at a manageable level. Inside, you'll find a thoughtfully designed layout ideal for multi-generational living. The oversized first-floor bedroom suite w/ full bath is perfect for guests, adult childre living at home or aging family members you may want to keep close. The spacious eat-in kitchen is perfectly positioned between the formal dining room & family room. In addition to the highly desirable AGA Stove, it features a walk-in pantry, custom countertops, farm sink overlooking the backyard & prep sink in the large center island. The perfect flow continues into the adjoining family room, accented w/ a gas fireplace & cathedral ceiling, through the sliding doors and into the glass enclosed sunroom overlooking the lush private backyard. Gleaming hardwood floors throughout and in all 6 bedrooms. With true comfort in mind the custom full bathrooms upstairs have been updated with exceptional materials, oversize glass framed showers, a soaking tub and accented with Veito Heaters. Conveniently located just a few miles to the ferry, train or HWY 35, don't miss this rare opportunity to own a home that offers both refined living and a connection to nature. Whether you're relaxing in the sunroom, cooking with your AGA, or harvesting from your garden, this property invites you to live well every day.

6 Carriage Drive, Middletown

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

Selling Office: EXP 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.

$590,000
6 Beds ⋅ 3 Baths
Welcome to your dream home! This renovated gem boasts 6 bedrooms and 3 full bathrooms, perfect for families of any size. As you step inside, you'll be greeted by a gorgeous new kitchen featuring stainless steel appliances and sleek black granite countertops. The heart of the home, this kitchen is ideal for entertaining or preparing gourmet meals. The master bedroom offers a sanctuary with its own master bathroom, providing privacy and luxury. The living room is bathed in natural light, creating a warm and inviting atmosphere. With easy access to the backyard, you can seamlessly extend your living space outdoors for gatherings or relaxation. Situated on a humongous piece of property measuring 100x165, this home offers plenty of space for outdoor activities and features two sheds for storage. Stay comfortable year-round with 2 zoned forced hot air and air conditioning, ensuring optimal temperatures throughout the house. Convenience is key with an efficient garage for one compact car or workspace, and a long driveway providing ample parking for multiple vehicles. For added convenience, there's a stackable washer dryer conveniently located off the kitchen, making laundry days a breeze. Located on cul-de-sac with minimal traffic, this home offers peace and serenity, providing the perfect retreat from the hustle and bustle of everyday life. Don't miss out on the opportunity to make this your forever home! Schedule a viewing today.

11 Williams Avenue, Middletown

Listing courtesy of Sigman Realty. Contact:

Selling Office: One Stop Realty Shop.

$983,000
6 Beds ⋅ 4 Baths
This is it! Move right in to this beautifully renovated 6 Bed 3.5 Bath home right in the heart of Middletown near shopping, County parks, Middletown Train Station, golf courses, restaurants, and ferries to NYC! So many desirable features to this home including: * Large Level Fenced-in Yard * Stone and Vinyl Siding * Welcoming Foyer * Hardwood Floors * Gas Fireplace * Open-Concept Living Dining and Kitchen * Stone Countertops* Stainless Steel Appliances * Sliding Doors * Sprinkler System * Spacious Screened-in Porch * Oversized Composite Deck * Paver Patio and Walkways * Hot Tub * Family Room * Wood-Burning Stove * Primary Suite * 3 Full Bathrooms * Mother/Daughter Apartment with 2 Bedrooms, Full Bath, Walk-In Closet and 2nd Kitchen * Attic Space * Lovely Landscaping * and More! Don't wait

3 Rolling Knolls Drive, Middletown

Listing courtesy of Bottone Realty Group Inc. Contact:

Selling Office: Keller Williams Realty Spring Lake.

$2,300,000
6 Beds ⋅ 5 Baths
Nestled on 2.25 acres of lush, rolling countryside, this Provence-inspired estate exudes an air of elegance and exclusivity. Tucked away from the hustle and bustle, the property offers a serene retreat for those who seek privacy and sophistication in equal measure. Approaching the estate, a dramatic entrance welcomes guests with its stately charm, hinting at the grandeur that lies within. A palatial foyer unfolds before you, adorned with intricate detailing and timeless craftsmanship. The grandeur of the space immediately sets the tone for the luxurious living that awaits. Beyond the foyer, the heart of the home beckons, where a spacious loggia awaits, perfect for grand entertaining or quiet moments of reflection amidst the beauty of nature. Bathed in natural light, this exquisite space seamlessly blends indoor and outdoor living, offering a tranquil oasis for gatherings large and small. Throughout the home, quality finishes abound, from rich hardwood floors to custom millwork and artisanal tile. Every detail has been meticulously curated to evoke a sense of refined elegance, while still embracing the warmth and charm of the Provencal countryside. Descending to the lower level, a world of luxury awaits, with a meticulously crafted wine cellar offering the perfect retreat for oenophiles and connoisseurs alike. As the sun sets over the sprawling grounds, casting a golden hue across the landscape, it's clear that this Provence-inspired estate is more than just a homeit's a sanctuary, where every detail has been thoughtfully designed to elevate the art of living to new heights.

247 Monmouth Avenue, Middletown

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

Selling Office: Coldwell Banker Realty.

$2,405,000
6 Beds ⋅ 6 Baths
You are going to fall in LOVE w/ this home! Beautifully appointed Colonial abutting bucolic Shadow Lake ON SPRAWLING LEVEL GROUNDS w/ gorgeous NEW salt-water pool & well wtr for irrigation. Decorated to perfection w/ a neutral interior, sensational natural light, ovszd windows & a fantastic modern layout ideal for every day living/entertaining alike. Chef's kit w/ high-end cust inset cabinetry & breakfast bar seating open to FR w/ cust bulit-ins - + a separate front to back great rm. Lux primary w/ ample closet space, private terrace & spa-like full bath w/ double vanity, tub & steam shower. Large BRs w/ great closet space & 3 add'l full baths. First & 2nd fl laundry, mud rm w/ built-ins, bsmt & more! Nestled at the foot of a quiet cul-de-sac in highly sought after Lincroft sec of town.

17 Page Drive, Middletown

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

Selling Office: Douglas Elliman of NJ LLC.

$1,150,000
6 Beds ⋅ 4 Baths
Shangri-La!! You can have it all! Nestled on a serene cul-de-sac in a well loved Chapel Hill neighborhood, live your life at this year round resort! Enriched with love and laughter by a close-knit family, this cherished 3800 square foot Colonial; Mother/Daughter home is ready for you to make your own memories on Edgebrook Court. Enter this classic center hall colonial to find a lot to love . . hardwood floors, freshly painted rooms, beautiful fireplace, sunroom addition with walls of windows overlooking a plush and private backyard. 4 large bedrooms, full basement, 2.5 baths and 2nd floor game room in main house. The main home connects to a well appointed apartment by a common laundry room and offers a kitchen, living room, 2 bedrooms, full bathroom and a private entrance The outdoors offers an oversized 2 car detached garage, whole house generator and an amazing backyard. The pool area is fenced in for safety and includes a pool house with electricity! LET THE PARTY BEGIN!!!

6 Edgebrook Court, Middletown

Listing courtesy of C21 Thomson & Co.. Contact: yetmanmaureen@gmail.com

Selling Office: Keller Williams NJ Metro Group.

$2,900,000
7 Beds ⋅ 9 Baths
12 prime acres in the heart of Middletown with a breathtaking private entry way straight out of a movie flanked by 2 ponds with fountains. This is one of the last large parcels in the area for either redevelopment or to rent the current 5,400 sq. ft. home as a group home, retreat, camp, horse compound etc. This property boasts a 13 room estate, separate 4 car garage, large in ground pool with slide and cabana, full tennis and basketball courts, 4 stall horse barn with paddocks. Redevelopment option has previously approved plans to build 6 additional luxury homes to create an exclusive enclave of 7 homes.

911 Middletown Lincroft Road, Middletown

Listing courtesy of Goldstone Realty. Contact:

$390,000
6 Beds ⋅ 3 Baths
This is an incredible opportunity to own a one-of-a-kind Colonial Handyman Special in Middletown! This 6 Bedroom, 3 Bathroom is set back from the road, with a semi-circle driveway providing easy access. A basement that could easily be transformed into a mother/daughter style living space, with a separate entrance. The interior of the home offers plenty of space for entertaining and family life, and the exterior boasts a large yard ideal for outdoor activities. With a little imagination and TLC, this home could be your dream come true. Don't miss out - make it yours today!

168 Leonardville Road, Middletown

Listing courtesy of C21 Thomson & Co.. Contact:

Selling Office: Keller Williams Realty East Monmouth.

$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.