Middletown Homes under $400,000

Welcome to Middletown, a charming city nestled in the heart of the United States, where small-town charm meets vibrant community spirit. Known for its friendly neighborhoods and rich history, Middletown offers a delightful blend of suburban tranquility and urban convenience. With picturesque parks, bustling local shops, and a strong sense of community, it’s no wonder that families and individuals alike are drawn to this inviting locale.

One of the most appealing aspects of Middletown is its affordable housing market. For those seeking their dream home without breaking the bank, you’ll be pleased to discover a variety of homes available for under $400,000. Whether you’re a first-time buyer, a growing family, or looking to downsize, Middletown has something to suit your needs. From cozy single-family homes with lush backyards to modern townhouses with contemporary finishes, the options are diverse and inviting.

Living in Middletown means enjoying a lifestyle that balances work and play. The city boasts excellent schools, recreational facilities, and an array of dining options that cater to all tastes. Plus, with easy access to major highways, commuting to nearby cities is a breeze.

In Middletown, you’ll find not just a house, but a place to call home. Explore the vibrant real estate market today and discover the possibilities that await you in this welcoming community. Your dream home is just a visit away!

Newest Middletown Homes under $400,000

$295,000

3 Beds ⋅ 2 Baths ⋅ 1056833 MLS

SPACIOUS FIRST-FLOOR RANCH-STYLE CONDO offering easy one-level living with 3 bedrooms and 2 full baths and no interior steps. Convenient parking is located just a few steps from the front door, making this a great option for anyone looking for easy accessibility and the convenience of first-floor living. The home features central air, laminate flooring and carpeting, a spacious eat-in kitchen with plenty of room for everyday dining, and a large living area with sliding glass doors leading to your own private patio. There is plenty of natural light throughout the home, creating a bright and comfortable living space. The primary bedroom offers its own private full bath and walk-in closet. Two additional generously sized bedrooms provide flexibility for family, guests, or a home office, along with a second full bath. A convenient stackable washer and dryer completes the one-level layout. This condo has been enjoyed for many years and offers a wonderful opportunity for the next owner to make it their own with some fresh paint and personal touches. Conveniently located close to shopping, major highways, bus transportation, and the train. With three bedrooms, two full baths, first-floor living, a private patio, and an easy-to-navigate layout, this home offers a lot of potential in a convenient location.

18 Revere Drive, Middletown

$374,999

2 Beds ⋅ 1 Baths ⋅ 1053196 MLS

Welcome home to 138 Prospect Avenue! This beautifully renovated, truly turn-key home is ready for its new owner. With thoughtful updates throughout, everything feels fresh, modern, and move-in ready. Step inside to find newly finished hardwood floors, recessed lighting, and an inviting open-concept layout. The updated kitchen features brand-new sparkling granite countertops, stainless steel appliances (all under three years old), recessed lighting, and new hardwood flooring. Just off the kitchen, a charming 4' x 8' deck provides the perfect spot for grilling, enjoying your morning coffee, or conveniently bringing groceries up from the driveway. The living room flows seamlessly into the kitchen and features a wood stove that helps heat the entire home while keeping fuel costs down. A beautiful bay window fills the space with morning sunlight and highlights the gleaming hardwood floors. Two nicely sized first-floor bedrooms offer abundant natural light and hardwood flooring, providing comfortable and versatile living space. The fully finished lower level adds even more room to spread out, with a spacious family room, bonus room that could make a great home office, and a large storage/workshop area. The laundry area includes a brand-new washer and dryer, along with a utility sink to make household chores a breeze. The family room (25’11” x 14’8”) features brand-new flooring, a built-in bookcase with a clever secret door leading to the storage area, and a decorative fireplace that adds character and charm. Sliding glass doors open directly to the partially fenced, expansive backyard, creating an easy indoor-outdoor connection. Outside, you'll find a shed and plenty of space to create your ideal outdoor living area. With extensive updates, flexible living space, and a generous backyard, 138 Prospect Avenue is a wonderful place to call home!

138 Prospect Avenue, Middletown

$315,000

4 Beds ⋅ 2 Baths ⋅ 1058232 MLS

The property offers two separate units, in need of some TLC this classic two-story design features a covered front porch, a private driveway, yard space, and plenty of character throughout. Whether you are expanding an investment portfolio or looking for a multi-family property with long-term rental potential, this home offers flexibility and upside. Conveniently located near shopping, restaurants, schools, and everyday services, with the Galleria at Crystal Run just a short drive away. Outdoor recreation is also nearby at Fancher-Davidge Park and along the Orange Heritage Trail. Easy access to major roadways, including Route 17 and I-84, makes commuting throughout the Hudson Valley convenient. Bring your ideas and take advantage of the potential this Middletown two-family property has to offer. Tenants pay for their own electric, heat & hot water.

34 Houston Avenue, Middletown

$309,900

2 Beds ⋅ 1 Baths ⋅ 1053243 MLS

Welcome to this cozy and comfortable 2-bedroom, 1-bath home in Middletown! Offering practical living space and plenty of storage, this home features a full finished walkout basement with a finished recreation room, laundry area with washer and dryer, and a new water heater. The full walk-up attic provides excellent additional storage and offers plenty of standing room. The home sits on approximately 0.19 acre with municipal water and sewer and low taxes. Bonus opportunity: the sale includes the adjacent 0.18-acre parcel at 100 Sprout Street, providing additional land and flexibility for the new owner. A comfortable home with useful finished space, great storage, and the added value of an additional adjoining parcel. Close to NJ Transit to NYC, restaurants, shopping, wineries and everything the beautiful Hudson Valley has to offer. Don't miss this opportunity to home ownership!

102 Sproat Street, Middletown

$365,000

3 Beds ⋅ 1 Baths ⋅ 1058181 MLS

Beautifully renovated Middletown home with an updated, move-in-ready interior. The property offers a long driveway with plenty of parking and is one of the few homes in the area with such generous outdoor space. Enjoy an exceptionally large, deep, fully fenced backyard with plenty of room to relax, entertain, and enjoy the outdoors. Conveniently located near shopping, dining, transportation, and major roadways.

74 Genung Street, Middletown

$74,900

2 Beds ⋅ 2 Baths ⋅ PADA2064768 MLS

Welcome home to this brand-new 2026 Clayton Topaz, offering comfortable and modern living space. With a spacious 14' x 69' floor plan, this home combines practical design with fresh finishes and move-in-ready appeal. The inviting kitchen features light wood cabinetry, a marble-look countertops, stainless-steel appliances, a gas range, refrigerator, dishwasher, and double-bowl sink. Durable wood-look flooring flows through the kitchen and main living areas, creating a warm, contemporary feel. The home offers a clean, neutral interior with carpeted bedrooms, modern white doors, ample storage, and a convenient hallway layout. Outside, you'l find attractive gray vinyl siding, a covered-style entry area with new steps and railings, and a manageable lawn area.

183 Eby Ln, Middletown

$250,000

3 Beds ⋅ 1 Baths ⋅ DENC2112348 MLS

INVESTOR SPECIAL! Fixer Upper with a separate lot! .16 Ranch Home and .08 Adjacent Lot.

313 Jefferson St, Middletown

$315,000

4 Beds ⋅ 3 Baths ⋅ MDFR2090138 MLS

7313 W Springbrook Ct W, Middletown

$74,900

2 Beds ⋅ 2 Baths ⋅ PADA2064742 MLS

Welcome home to this brand-new 2026 Clayton Topaz, offering comfortable and modern living space. With a spacious 14' x 69' floor plan, this home combines practical design with fresh finishes and move-in-ready appeal. The inviting kitchen features light wood cabinetry, a marble-look countertops, stainless-steel appliances, a gas range, refrigerator, dishwasher, and double-bowl sink. Durable wood-look flooring flows through the kitchen and main living areas, creating a warm, contemporary feel. The home offers a clean, neutral interior with carpeted bedrooms, modern white doors, ample storage, and a convenient hallway layout. Outside, you'll find attractive gray vinyl siding, a covered-style entry area with new steps and railings, and a manageable lawn area.

119 Bentley Ln, Middletown

$389,000

3 Beds ⋅ 2 Baths ⋅ 1056390 MLS

Welcome home to this charming 3 bedroom, 2 bath residence perfectly situated on a quiet cul-de-sac in one of the area's most desirable and commuter friendly locations. Offering the ideal blend of comfort, convenience and outdoor enjoyment, this wonderful home is ready for its next owner. Step inside to discover warm hardwood floors and crown molding that add character and charm throughout the home. The kitchen is equipped with sleek black stainless appliances and offers ample cabinetry. One of the home's standout features is the walkout basement, which provides approximately 700 square feet of additional living space ready to be customized to suit your needs. Whether you envision a family room, home office, gym, recreation area, or guest space, the possibilities are endless. Outside, you'll find your own backyard oasis. Spend warm summer days, relaxing by the above ground pool, hosting barbecues, gardening or simply unwinding. The level yard offers plenty of room for outdoor activities and provides the perfect setting for gathering and making memories. Conveniently located near major highways, public transportation, shopping (yes, only 5 minutes away!) restaurants, parks and schools, this home is ideal for those seeking an easy commute without sacrificing a neighborhood setting. The cul-de-sac location minimizes through traffic and offers a sense of community. Whether you're a first time homebuyer, looking to downsize, or searching for a home that combines comfort, convenience and value, this property is sure to impress.

63 Orchard Hill Road, Middletown

$199,000

1 Beds ⋅ 1 Baths ⋅ 1054352 MLS

This well-maintained 1-bedroom, 1-bathroom condo offers comfortable, convenient living with the added benefit of desirable ground-floor access. The functional layout features a spacious living area with direct access to your own private patio. An awning provides welcome shade and makes the patio an inviting extension of the living space. The generously sized bedroom offers plenty of room to create a comfortable retreat, while the convenient one-level layout makes everyday living easy. Whether you're looking for a low-maintenance residence opportunity, this Middletown condo is ready for its next owner!

122 Sycamore Drive, Middletown

$399,999

3 Beds ⋅ 2 Baths ⋅ 1056459 MLS

Welcome to this beautifully maintained 3-bedroom, 2-full-bath ranch nestled on 0.72 acres in the Town of Mount Hope, within the Minisink Valley School District. Thoughtfully updated and designed with energy efficiency in mind, this home has been thoroughly insulated and is Energy Star qualified, offering comfort and efficiency throughout the seasons. The inviting interior features a refreshed kitchen with LG stainless steel appliances, including a new refrigerator and stove. New red oak floors. Warm architectural details throughout the home include wainscoting and a decorative shiplap fireplace, while the bathroom showcases a distinctive vanity topped with a natural raw stone slab. The finished lower level adds an impressive amount of flexible living space and is ready to adapt to your needs. Use it as a recreation room, den, home office, media room, gym, playroom, or additional guest space. A second entrance, full bathroom, sink area, and laundry room with a wet-bar-style setup make this level particularly versatile for entertaining, hobbies, working from home, or simply spreading out. Step outside and enjoy the expansive deck overlooking the property, along with a charming stone walkway and modern vinyl siding that give the home a clean, updated exterior. The stone fire pit area provides a comfortable place to gather outdoors, while the detached garage offers excellent additional storage for vehicles, tools, equipment, or recreational belongings. Set in a peaceful Mount Hope location with the convenience of nearby Middletown amenities, this home offers a thoughtful combination of comfortable living spaces, practical updates, energy-conscious improvements, and versatile space both inside and out.

1040 Highway 211 W, Middletown

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.

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.