Browse All Middletown CT 5 Bedroom Properties for Sale

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

$549,900

5 Beds ⋅ 4 Baths ⋅ 24213729 MLS

Welcome to this beautiful 10-room home offering 3,316 square feet of living space, five bedrooms, three full bathrooms, and a half bath. Mature landscaping enhances the property's charm and creates an inviting setting. The spacious layout offers. Plenty of room for everyday living and entertaining with flexibility to suit your needs. The first-floor primary bedroom features a private full bathroom for convenient main level living. Three fireplaces add warmth and character, including one in the basement. Where you'll find a half bath. There is an outbuilding equipped with heat, air conditioning and sink provides additional space for hobbies, a workshop, or create a pursuit. With generous living space and distinctive features throughout, this lovely property is ready for its new owners to make it their own.

495 Ridge Rd, Middletown

$659,000

5 Beds ⋅ 3 Baths ⋅ 24210098 MLS

Welcome to 36 West Poplar Road, a beautifully appointed custom home built in 2014 and ideally situated in the desirable Poplar Estates subdivision. Lightly lived in and meticulously maintained, this impressive home offers quality craftsmanship, generous living spaces, and the convenience of public utilities. A handsome bluestone walkway and welcoming front entrance set the tone as you arrive, while the three-car attached garage provides plenty of space for vehicles and storage. Step inside to gleaming hardwood floors and a freshly painted interior filled with natural light. All-new custom window blinds add a polished finishing touch throughout the home. The thoughtfully designed floor plan features a spacious first-floor primary suite, offering the ease and flexibility of main-level living while still providing ample additional space for family and guests. The custom design, beautiful finishes, and exceptional condition make this home truly move-in ready. Adding tremendous potential is the huge walkout lower level, offering an abundance of space ready to be finished for additional living areas, a recreation room, home gym, office, guest quarters, or whatever best suits your lifestyle. Set within an established neighborhood yet convenient to Middletown's shopping, dining, highways, and amenities, this exceptional property combines newer construction, custom details, public utilities, and room to grow-a wonderful opportunity in Poplar Estates.

36 W Poplar Rd, Middletown

$305,900

5 Beds ⋅ 2 Baths ⋅ 24203700 MLS

**Multiple Offers, Highest and Best Due EOD Wednesday, 9/9/26** Opportunity knocks in the heart of Middletown! This two-family home sits just minutes from Route 9, public transportation, and the Main Street corridor with its restaurants, shops, and year-round events. Live in one unit and have a tenant help pay your mortgage, or add a solid two-family to the portfolio - a great fit for owner-occupants and investors alike. Unit 1 has been freshly updated with new flooring, fresh paint, an updated kitchen and bath, and ceiling fans. Unit 2 offers a functional layout with an enclosed sun porch and its own private entry. Separate utilities, including two electrical panels and two heating systems, keep operating simple. Additional highlights include enclosed porches, new flooring and updates throughout, an open unfinished basement with plenty of storage, and off-street parking for multiple vehicles. Appliances will be provided with the right offer. Close to Wesleyan University, hospitals, parks, and commuter routes to Hartford and the shoreline. Easy to show - schedule today! Agent Owner

105 Spring St, Middletown

$349,000

5 Beds ⋅ 2 Baths ⋅ 24201926 MLS

Perfect 3-Bedroom Home Layout with 2 Bonus Flex Rooms/Offices! Welcome to this spacious 1952 Middletown Colonial, where classic charm meets low-maintenance living in a quiet neighborhood. Step inside a welcoming foyer with an entry closet that opens into a sun-drenched living area highlighted by a large bay window. The home features stunning hardwood floors throughout, flowing into a functional kitchen complete with natural wood cabinets, Corian countertops, a matching backsplash, and durable laminate flooring. Designed for effortless lifestyle flexibility, the main level hosts two bedrooms, including the primary bedroom, alongside a full bathroom with a tub/shower. Upstairs, you will find three additional bedrooms, perfect for a home office or private gym, and a second full bathroom with a tub/shower. The expansive basement is perfect for a hobbyist equipped with a dedicated tool workbench, storage shelving, and a laundry area with a washer and dryer. Outside, the home has low-maintenance vinyl siding and a cleared, level rear yard with mature landscaping and a handy tool shed. This prime location keeps you tranquil at home while placing you just minutes from Wesleyan University, downtown restaurants, nightlife, and scenic walks at Harborpark or Wadsworth Falls State Park. Commuting is a breeze with instant access to Route 9 and Route 66. This turn-key five-bedroom gem blends comfort, space, and ultimate Connecticut convenience.

130 Spencer Dr, Middletown

$364,900

5 Beds ⋅ 3 Baths ⋅ 24199686 MLS

This well maintained colonial, located just steps from the bustling downtown of Middletown, is ready for its new owner! Three units, all on different floors, offer flexible plans for owner-occupants and investors alike! The first and second floor units are comfortably controlled with high efficiency Navien units, both with a 2 bed/1 bath layout. The third unit is also natural gas, and provides a generous sized 1 bed/1 bath unit. The units themselves are mostly updated, some with fresh paint and tile work tastefully done. A two car garage and off street parking provide ultimate convenience for owners and/or tenants. Lively flower beds decorate the front walkway, adding to the curb appeal. A back staircase seconds as small deck platforms overlooking the backyard. Whether living in one unit and renting the others for residual income, or adding this wonderful opportunity to your investment portfolio, this one is NOT to miss. Schedule your private showing today!

53 Spring St, Middletown

$75,000

5 Beds ⋅ 3 Baths ⋅ 24182301 MLS

Opportunity awaits at this 2-family residential property in a convenient Middletown location. The existing structure has sustained fire damage and is being offered strictly as-is. Ideal for investors, contractors, or buyers seeking a renovation or redevelopment project. Situated on a level lot with access to public water and public sewer. Close to shopping, dining, parks, and commuter routes. A unique chance to restore, reimagine, or rebuild subject to municipal approvals.

18 Portland St, Middletown

$849,900

5 Beds ⋅ 4 Baths ⋅ 24177933 MLS

Tucked away on a quiet, highly desirable cul-de-sac of only 7 homes in the sought-after South Farms district, this beautifully crafted 5-bedroom, 3.5-bathroom colonial features a stunning brick-front facade and exceptional curb appeal. Boasting a coveted 3-car attached garage, the home greets you with an abundance of natural light and gleaming hardwood floors flowing seamlessly throughout the main and upper living areas. The spacious, well-designed layout is perfect for both effortless entertaining and comfortable daily living, offering a generous floor plan with an ideal flow. The Ultimate Flexible Space: The true crown jewel of this property is the fully finished walk-out basement that adds an additional 1,070 sq/ft! Configured as a complete, self-contained in-law apartment, this private lower level includes its own separate entrance, full kitchen, living space, bedroom and bath-absolutely perfect for multi-generational living or long-term guests. Situated in a fantastic location, this home offers the generous space you need, the classic aesthetic you desire, and the unique floor plan flexibility that is so incredibly hard to find. Don't miss this versatile gem!

29 Copper Beech Dr, Middletown

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

5 Bedroom Middletown Real Estate

Our website features the best real estate search for 5 bedroom 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!

Browse All Middletown CT 5 Bedroom Properties for Sale

5 Bedroom Middletown Real Estate

How much is your home worth?

How much is your home worth?