Browse All Middletown CT Multi-Family 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

$365,000

3 Beds ⋅ 2 Baths ⋅ 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

$274,900

4 Beds ⋅ 2 Baths ⋅ 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

$524,900

4 Beds ⋅ 4 Baths ⋅ 24208994 MLS

Welcome to this well-maintained two-family home, ideally suited for multigenerational living, extended-family arrangements, or an owner-occupant seeking income potential. Situated on a corner lot near downtown Middletown, this expansive property occupies a double lot totaling approximately 0.33 acres and offers abundant indoor and outdoor space. The home features high 11-foot ceilings, graceful archways, and oversized windows that fill the interior with exceptional natural light. Both units offer comfortable living areas, and the finished lower level provides a second kitchen full bath & laundry. A family room with a fireplace offers excellent flexibility and may serve as a potential third bedroom. The kitchen is equipped with granite countertops, while natural-gas heat and air-conditioning units provide year-round comfort. Outside, enjoy plentiful parking, a detached two-car garage with attic. The generous double lot offers room to relax, garden, entertain, or explore future possibilities, subject to local approvals. Conveniently located close to downtown Middletown, shopping, restaurants, and everyday amenities, this is a rare opportunity to own a spacious and adaptable two-family residence in a highly accessible location.

149 Spring St, Middletown

$600,000

9 Beds ⋅ 6 Baths ⋅ 24209312 MLS

Exceptional Mixed Use 3-Unit Investment Opportunity in Middletown! Well-maintained three-unit property offering the feel of townhouse-style living with the income potential of a multifamily investment. Each spacious unit features 3 bedrooms, 1 full bath, 1 half bath, an eat-in kitchen, abundant natural light, basement storage, and washer/dryer hookups. A standout feature is the private under-building garage for each unit with direct access, plus ample off-street parking and a rear driveway. Separate utilities provide added convenience for ownership and management. Ideally located near downtown Middletown, Wesleyan University, Middlesex Health, shopping, dining, parks, and major commuter routes. An excellent opportunity for an investor or owner-occupant looking to generate rental income while building equity. Property being Sold As Is. Agent/Owner related.

227 E Main St, Middletown

$579,900

6 Beds ⋅ 3 Baths ⋅ 24208519 MLS

Group showing Sunday, 10/18, 12 noon! Fantastic investment opportunity just minutes from Downtown Middletown! This beautifully maintained three-family property offers a great combination of location, condition, and long-term investment potential. All three units offer two large bedrooms. Each unit also enjoys its own private porch or balcony, giving tenants valuable outdoor space. This property has been well cared for with significant updates throughout, including impeccably updated mechanicals, helping take some of the worry out of owning a multifamily property. A three-car detached garage in the rear adds even more value, along with additional off-street parking. Located on a quiet, desirable street close to Downtown Middletown, the property offers easy access to restaurants, shopping, Wesleyan University, major routes, and everything the downtown area has to offer. Whether you're looking to add a solid three-family to your investment portfolio or live in one unit while collecting rent from the other two, this is the type of multifamily property that is getting harder to find. Great location, private outdoor spaces, garage, strong updates, and three income-producing units all in one property. Don't wait on this one-schedule a showing and see the opportunity for yourself!

225 Pearl St, Middletown

$369,900

6 Beds ⋅ 2 Baths ⋅ 24208513 MLS

Ideal for an investor or owner occupant this 2 family home offers 2 units 5 rooms with 3 bedrooms each. The first floor unit with hardwood floors 3 spacious bedrooms, refreshed bath, and a kitchen with a walk in pantry. The second floor has been remodeled with 3 bedrooms and the primary bedroom with a large walk in closet or storage room. Updated kitchen, laminate floor, white cabinets and walk in pantry and refreshed full bath with tile tub surround and floor. This property has a front porch and a rear porches. A walk up attic offers additional space with an option for future expansion. A full basement with a full bath and a finished room. Furnaces and Hot water heaters replaced in 2021. Driveway which will allow for 2 cars of off street parking. Great opportunity to add to a portfolio.

42 Grand St, Middletown

$1,395,000

21 Beds ⋅ 9 Baths ⋅ 24206879 MLS

Two-building mixed-use investment opportunity in Middletown. The offering includes 61 East Main Street with four apartments and two storefronts, plus a separate three-apartment building at 2-6 Flower Street, offering a more private off Main street setting. Six apartments are occupied, while the seventh is being updated with a new kitchen and bathroom. Upon completion and lease-up at the projected rent, the property is expected to offer an approximately 9% cap rate, that's before any income from the two vacant storefronts. Zoned MXI, the storefronts have previously operated as a clothing store, salon and convenience store in past years, offering flexible possibilities subject to zoning guidelines. Additional features include private off-street parking space, wood flooring, same ownership since 2014, units updated/repaired over ownership for housing voucher compliance/inspections, separate utilities, a yard area and visible East Main Street frontage. With a Walk Score of 74, the property is close to Downtown Middletown, restaurants, shops, services, Wesleyan University, the riverfront, public transportation and Route 9. Two buildings, one investment and multiple opportunities to increase income!!! Interior pics will be added prior to active date.

61 E Main St, 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

$365,000

4 Beds ⋅ 2 Baths ⋅ 24202551 MLS

Welcome to this beautifully remodeled two-family home ideally located within walking distance of vibrant downtown Middletown! This property offers the perfect blend of modern updates, spacious living, and unbeatable convenience. Both units have been fully remodeled with new appliances and updates throughout, making this an excellent opportunity for an owner-occupant, investor, or multi-generational living arrangement. Enjoy the added charm and versatility of enclosed back porches, perfect for relaxing, extra storage. A standout feature is the walk-up attic, offering approximately 650 additional square feet of living space-an incredible opportunity to create additional bedrooms, an office, recreation room, or whatever best suits your needs. Natural gas heat and hot water, separate utilities. Common laundry area in the basement with brand new washer and dryer. Step outside and enjoy everything Middletown has to offer, with parks, restaurants, shops, and downtown attractions all just a short walk away. Located in the heart of a lively and growing community, this home combines convenience, character, and future potential. Move-in ready, fully updated, and in a fantastic location-this is a two-family opportunity you won't want to miss!

74 Grove St, 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

$419,000

8 Beds ⋅ 4 Baths ⋅ 24190092 MLS

Exceptional mixed-use investment opportunity convenient to downtown Middletown! This property features 2 commercial units and 3 residential units, offering a balanced blend of commercial and residential income that makes it an ideal addition to any investor's portfolio. Both commercial spaces are currently vacant, making this an excellent opportunity for someone who wants to open their own business on the ground floor while collecting steady rental income from the apartments upstairs. The commercial spaces enjoy excellent street frontage and high visibility along busy East Main Street, providing strong exposure for retail, office, or service-oriented businesses-with one of the commercial units already featuring a dedicated kitchen. The 3 residential units offer versatile 1, 2, and 3 bedroom layouts, each featuring 1 full bathroom. These units offer strong rental appeal in a highly desirable location. Situated within walking distance to restaurants, shopping, entertainment, public transportation, and local amenities, this property benefits from Middletown's vibrant atmosphere. Whether you're looking to expand your investment portfolio, generate multiple income streams, or establish your business while collecting residential rental income, this versatile property offers outstanding potential. Convenient access to Route 9, I-91, Wesleyan University, and surrounding communities. Make an appointment today to view this property!

71 E Main St, Middletown

$410,000

6 Beds ⋅ 2 Baths ⋅ 24188066 MLS

Turnkey multifamily for owner occupied or investment opportunity in a desirable Middletown location! This fully remodeled property offers strong income potential with updated units featuring modern kitchens, renovated bathrooms, new flooring, and contemporary finishes throughout. The building has been well maintained and provides an excellent opportunity for investors seeking a low-maintenance asset with immediate cash flow. Conveniently located near downtown Middletown, shopping, restaurants, schools, parks, and major highways, making it attractive to tenants and ensuring long-term rental demand. Whether you're expanding your portfolio or acquiring your first investment property, this move-in-ready multifamily is an opportunity you won't want to miss. Being SOLD AS-IS.

163 Pearl St, Middletown

$390,000

7 Beds ⋅ 2 Baths ⋅ 24188106 MLS

Owner occupied or investors! Fully renovated investment opportunity in the heart of Middletown! This well-maintained 7 bedrooms 2 bath, multifamily property has been completely remodeled and offers immediate cash flow with tenants already in place. Each unit is currently rented, providing strong and stable rental income from day one. Updates include modern kitchens, renovated bathrooms, updated flooring, fixtures, and mechanical improvements throughout. The property has been thoughtfully upgraded while maintaining its charm and functionality. Ideal for investors seeking a turnkey asset with reliable tenants and minimal deferred maintenance. Conveniently located near shopping, restaurants, schools, public transportation, and major highways. Don't miss this opportunity to add a fully occupied, income-producing property to your portfolio. Being SOLD AS-IS. OWNER/AGENT.

194 Liberty 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

$1,300,000

12 Beds ⋅ 8 Baths ⋅ 24178851 MLS

Unique mixed-use opportunity in Middletown offering strong cash flow and flexible ownership potential. Property consists of a fully occupied 4-family, a fully occupied 2-family, and two 1,600 SF commercial garage/workshop spaces all situated on one lot with views of the Connecticut River and Arrigoni Bridge. One commercial space is leased, while the second vacant garage offers ideal owner-user potential for contractors, storage, workshop space, or additional rental income. Projected 8.2% cap at current occupancy, with stabilization potential of approximately 9.4-9.8% upon lease of the 2nd garage. Residential units feature a desirable mix of 1-, 2-, and 3-bedroom layouts with updates completed over time, including newer boilers and water heaters. Off-street parking, minutes to Route 9, downtown Middletown, and walking distance to Wesleyan University. Property conveyed as-is.

13-15 Portland St, Middletown

$369,900

4 Beds ⋅ 2 Baths ⋅ 24124801 MLS

Welcome to 58 Durant Terrace - a well-maintained 2-family home nestled in a quiet, desirable neighborhood just minutes from downtown Middletown, Wesleyan University, shopping, and dining. This versatile property offers two spacious units, each with 2 bedrooms, 1 full bath, bright living spaces, and hardwood flooring throughout. Ideal for investors or owner-occupants, live in one unit and rent the other to offset your mortgage! Features include: Separate entrances and utilities for each unit, updated kitchens and baths, generous backyard space perfect for entertaining or gardening. Off-street parking and potential garage or basement storage. Close to public transportation, parks, schools, and major highways. Whether you're looking to expand your rental portfolio or settle into a property with built-in income, 58 Durant Terrace is a rare find with solid potential - don't miss your chance to own this duplex gem in the heart of Middletown!

58 Durant Ter, 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.

Middletown Multi-Family Real Estate

Our website features the best real estate search for multi-family 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 Multi-Family Properties for Sale

Middletown Multi-Family Real Estate

How much is your home worth?

How much is your home worth?