Middletown Homes under $400,000

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Newest Middletown Homes under $400,000

$220,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24215423 MLS ⋅ Quail Run Village BLDG.

Two-bedroom, one full bathroom at Quail Run Village with basement Garage. This townhouse features an open floorplan which includes the kitchen with all stainless-steel appliances, dining area and living room. there is a slider to the deck from the kitchen. the 2ND floor has a primary bedroom with double closets. a guest bedroom/office. this unit includes an oversized basement garage with laundry area. There is a inground pool for summer enjoyment. the location offers quick access to route 9 and I-91, close to shopping, dining, downtown Middletown and Middlesex Hospital.

161 Cynthia Ln Unit F7, Middletown

$259,900

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24214896 MLS

CUTE RANCH HOME IN A GREAT NEIGHBORHOOD! Large eat-in kitchen with plenty of cabinet & counter space and a new oven range (2026.) Nice sized living room and 3 bedrooms, all with hardwood floors! Get cozy in the partially finished lower level with a wood burning stove, newer faux wood laminate floor that ADDS APPROX 330SQFT of beautiful living space. From the deck, enjoy your view of a huge, level, open backyard. The property backs to Upper Mill Pond that the seller has done some fishing and stand-up paddleboarding from! 2 sheds offer great storage. There's a solar panel Power Purchase Agreement (PPA,) for $196/month to lower electricity costs. The panels were installed in 2023 along with a new 200amp electrical service. New hot water heater in February 2026. Seller also has chickens! You can take over their care and reap the benefits of fresh eggs, or seller will find them a new home, your choice. Close to shops, restaurants, donuts, highway access, Middlesex Hospital and all the amazing food on Main Street!

116 Dorothy Dr, Middletown

$350,000

5 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24215211 MLS

Excellent investment opportunity in Middletown! Conveniently located near downtown Middletown, Wesleyan University, and major commuter routes, this three-family property is ideal for both investors and owner-occupants. Featuring two 2-bedroom units, one 1-bedroom unit, and a detached garage, the property currently has two long-term tenants and one vacant apartment, offering the flexibility to move right in while collecting rental income or operate as a fully rented investment property. A great opportunity to add value and build long-term equity!

239 Pearl St, Middletown

$365,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24214326 MLS

Welcome to 14 Casper Avenue in Middletown! This multifamily property offers approximately 2,225 square feet of living space, featuring 3 bedrooms and 2 full bathrooms. The in-law unit above the garage generates a monthly rental income of $900. Built in 1967, the property presents an excellent opportunity for investors or owner-occupants seeking a property with income potential. The home features gas forced-air heating, a partially finished basement for additional usable space, and a cozy fireplace. An attached garage provides convenient parking, while the lot offers outdoor space to enjoy. Conveniently located near local schools, shopping, dining, and everyday amenities, with access to major routes and the many attractions Middletown has to offer. Explore the possibilities this property presents!

14 Casper Ave, Middletown

$384,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24214296 MLS

Discover the perfect blend of comfort, privacy, and convenience at 36 McDowell Road! This updated two car ranch is tucked away on a quiet cul-de-sac and features a flat, fully fenced in yard ready for you to enjoy your own private outdoor retreat. Inside, you'll find a remodeled kitchen with granite countertops, two renovated bathrooms, and refinished flooring. Additional updates include three new mini split AC and heating as well, new radiators, recessed lighting, newer windows, a brand new deck, and a new washer and dryer. The basement offers excellent potential for additional living space. Conveniently located near shopping centers, restaurants, and everyday essentials, this Middletown home is ready for its next owner!

36 Mcdowell Rd, Middletown

$349,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24213576 MLS

Welcome to this spacious Colonial-style home offering over 2,500 square feet of living space. Featuring 4 bedrooms, central air conditioning, a generously sized kitchen with an eat-in area, and a separate dining area, this home offers plenty of room for comfortable living and entertaining. Originally designed as a side-by-side property, the home has been converted into a single-family residence, offering a unique layout with ample space and possibilities. Conveniently located near major highways, restaurants, shopping, and other local amenities, this property combines space, convenience, and opportunity. Don't miss the chance to make this home your own!

477 Hunting Hill Ave, Middletown

$274,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24213164 MLS

*Highest & best offers due by Tuesday 10/20 at 5 PM* Downtown convenience, classic character, and two-family potential come together at 219 Pearl Street! Wesleyan University is just a few blocks away, and Main Street's restaurants, shops, and local favorites are within walking distance! Russell Library, parks, public transportation, and convenient access to Route 9 add to the appeal. Two apartments on separate floors offer flexibility for investors or owner-occupants looking to offset housing costs with rental income. Both kitchens feature quartz countertops, with stainless steel appliances and a stackable washer/dryer in the first-floor unit. Wood flooring and generous windows bring warmth and natural light, while the second-floor screened-in porch offers a place to relax. A HUGE walk-up attic is a standout feature, offering abundant storage and exciting finishing potential for a buyer with the right vision. The sewer line was relined in 2021, a major infrastructure improvement! The paved driveway provides plenty of off-street parking, and the level rear yard adds outdoor space to enjoy. An unfinished basement, public water and sewer, natural gas, and a Navien tankless water heater installed in 2020 round out the features. Whether you're looking to house hack, generate rental income, or explore the home's untapped potential, this downtown two-family deserves a look. Make it yours today, this one won't last!

219 Pearl St, Middletown

27 Rising Trail Court, Unit 27, Middletown

$199,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24212390 MLS ⋅ Beacon Hill Towne Homes BLDG.

Welcome to 27 Rising Trail Court, a spacious 3-bedroom, 1.5-bath townhouse-style condo offering three levels of living space, a two-car carport, and a desirable end-unit location! Step inside to an open-concept main level featuring luxury vinyl flooring throughout, where the recently updated kitchen overlooks the dining area and sunken living room. The kitchen features granite countertops, stainless steel appliances, recessed lighting, and plenty of workspace, with a convenient half bathroom nearby. Just beyond, the sunken living room is filled with natural light from sliding glass doors that lead directly to your private back deck. Upstairs, the second floor offers two generously sized bedrooms with wall-to-wall carpeting, a dedicated laundry area, and a remodeled full bathroom featuring tile flooring, a tiled tub/shower surround, and an updated vanity. Continue to the third floor where you'll find an additional bedroom along with a large unfinished storage area offering excellent potential for additional usable space. Additional highlights include a brand-new water heater installed earlier this year, two-car covered parking, pool access, and an end-unit location situated beside the community swing set. The association also allows one dog or one cat, making this a great option for pet owners. Offered at $199,900, this is a fantastic opportunity to make the move from renting to homeownership!

27 Rising Trail Court, Unit 27, Middletown

$349,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24212644 MLS

Welcome to 95 Hunting Hill Ave, a charming and very well-cared-for 3-bedroom, 1.5-bath home surrounded by beautiful, established gardens. Inside, you'll find inviting living spaces and a versatile sunroom/den that has been freshly painted with brand-new flooring-perfect for an office, playroom, or cozy sitting area. Step outside to enjoy the backyard patio and peaceful garden setting. Conveniently located near downtown Middletown, Wesleyan University, restaurants, shopping, and nearby parks and trails. A lovingly maintained home ready for its next chapter!

95 Hunting Hill Ave, Middletown

$399,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24209279 MLS

Welcome to 30 Murray St, a well-maintained ranch-style home offering comfortable single-level living with a functional layout. This home features 3 bedrooms and 2 full bathrooms, providing flexible space for everyday living, guests, or a home office. The main level offers a practical floor plan with comfortable living spaces and three well-sized bedrooms with ample closet space. The finished basement provides additional usable space that can accommodate a recreation area, home office, gym, or other needs. Situated on approximately 0.23 acres, the property also offers a spacious yard with room for outdoor activities, gardening, entertaining, or simply enjoying the outdoors. Convenient ranch-style living with additional finished space makes this property worth a look.

30 Murray St, Middletown

$389,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24211673 MLS

Welcome to this beautifully renovated, move-in ready colonial that blends classic architectural layout with modern, functional living space. This rare oversized lot could be subdivided. Recently updated, this gorgeous home offers plenty of room to entertain and relax. The Main Level: Step past the inviting front porch into a bright, airy main floor of open and versatile spaces designed for gathering and comfort. A sprawling living room centers the home, flowing seamlessly into the formal dining area perfect for hosting holiday dinners and family gatherings. The kitchen offers wonderful natural light with a breakfast nook and custom floor-to-ceiling cabinets. Sunlit Family Room: Tucked at the back of the home is a spacious family room with wood burning stove, anchored by a full bath and dedicated laundry room. Bonus Sun Room: Bathed in natural light, the attached sun room serves as a perfect home office, reading nook, or plant oasis. Outdoor Entertaining: The sun room opens up directly to a massive, custom outdoor deck, ideal for summer barbecues, outdoor lounging, and evening entertaining. The Upper Level: The primary suite provides a true sanctuary with windows that flood the room with natural light. Two additional bright bedrooms offer great closet space and share a pristine, newly updated full bath. This beautifully updated home offers ultimate peace of mind with three high-ticket upgrades: new gas furnace, new hot water heater and rooftop solar panels.

66 Durant St, Middletown

$339,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24210969 MLS

This is home is located convenient to Shopping center and route 9. First floor main bedroom. Addition four bedrooms on the upper level and a full bath one of the bedroom does not have a closet. Builtin hutch in the dinning area. Living room with fireplace. (never used) Hardwood floors under carpeting. Handicap Ramp A detached two car garage. Property to be sold in "as is" condition, Contingent upon probate approval. Easy to show

42 Saybrook Rd, Middletown

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Middletown Homes under $400,000

Newest Middletown Homes under $400,000

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