Middletown Homes under $300,000

Middletown Homes under $300,000

Welcome to Middletown, a charming city that perfectly blends small-town warmth with modern conveniences. Nestled in the heart of [state or region], Middletown boasts a rich history, vibrant community spirit, and an array of amenities that make it an ideal place to call home. With its picturesque parks, delightful local shops, and a strong sense of community, residents enjoy a quality of life that is both fulfilling and affordable.

For those seeking a home in this inviting city, Middletown offers a fantastic selection of properties priced under $300,000. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, you’ll find a variety of options that cater to diverse lifestyles. From charming bungalows to spacious townhomes, these homes provide exceptional value without compromising on comfort or style.

Imagine waking up in a cozy home that’s just a stone’s throw away from local parks and schools, or enjoying a leisurely stroll through the tree-lined streets of your new neighborhood. With the affordability of homes in Middletown, you can invest in a property that not only meets your needs but also allows you to enjoy the local culture, community events, and outdoor activities that this lovely city has to offer.

With a friendly atmosphere and a strong sense of belonging, Middletown is more than just a place to live; it’s a place to thrive. Explore your options today and discover why so many are choosing to make Middletown their forever home!

Newest Middletown Homes under $300,000

175 Burgundy Hill Ln Unit 175, Middletown
$140,000
1 Beds ⋅ 1 Baths ⋅ 24221142 MLS ⋅ Peppermill Village BLDG.
Welcome to your next investment gem nestled in the heart of Middletown, CT! This beautifully renovated condo offers a seamless blend of modern convenience and classic charm. Situated on the first floor, this 1-bedroom, 1-bathroom unit provides an ideal living space accented by a spacious living room and dining area illuminated by natural light streaming through sleek sliding doors. The kitchen is a chef's dream, boasting abundant cabinetry perfect for all your storage needs. A brand-new hot water heater installed in 2023 ensures worry-free comfort for you or your tenants. Speaking of which, current lease occupancy not only secures immediate income but also makes it an excellent opportunity for savvy investors looking to expand their portfolio. Forget about parking woes with an assigned spot right outside the door, increasing ease and accessibility. With local amenities nearby and easy access to major routes, this property promises both convenience and connectivity. Whether you're seeking steady rental income or envisioning a future personal haven in thriving Middletown, this property stands ready to fulfill all potential aspirations!

175 Burgundy Hill Ln Unit 175, Middletown
803 Long Hill Rd Unit E, Middletown
$300,000
2 Beds ⋅ 3 Baths ⋅ 24220233 MLS ⋅ Long Hill BLDG.
Welcome to this inviting two-bedroom townhouse in the scenic Wesleyan Hills community! Hardwood floors extend across both living levels, complemented by updated lighting and an open main-level layout. The living room features a fireplace and sliding doors to a private deck, creating a comfortable setting for relaxing or entertaining. The adjoining dining area connects to the updated kitchen through a convenient pass-through with a granite-topped breakfast bar. Granite countertops also highlight the updated bathrooms. Upstairs, the spacious primary bedroom offers two large closets and its own full bathroom, while the second bedroom features two closets for additional storage. The unfinished basement provides room for storage and potential future living space. A one-car garage and ample guest parking add everyday convenience. Enjoy Wesleyan Hills' walking trails, lakes, ponds, and fountains-all surrounded by a picturesque landscape.

803 Long Hill Rd Unit E, Middletown
27 W Silver St Unit 27, Middletown
$250,000
2 Beds ⋅ 2 Baths ⋅ 24220593 MLS ⋅ West Silver Condominium BLDG.
Welcome to 27 West Silver Street-a turnkey, modern condo offering effortless low-maintenance living just minutes from vibrant downtown Middletown. Spanning 1,138 square feet, this bright and inviting home features a thoughtfully designed open-concept layout. The spacious living room centers around a cozy fireplace and flows directly through sliding glass doors to a private rear deck-the perfect spot for morning coffee, evening relaxation, or casual outdoor dining. The adjacent dining area connects seamlessly to a well-appointed kitchen equipped with full appliances and generous cabinetry. Upstairs, you'll find two generous bedrooms with ample closet space and a full bath, plus a convenient main-level half bath for guests. Rare for condo living, this home includes an attached garage and a dedicated private storage room situated right behind it-ideal for seasonal gear, tools, bikes, and bulky essentials. Additional highlights include efficient gas heating, central air conditioning, in-unit laundry, and low HOA dues. Enjoy unbeatable convenience with immediate access to Route 9, I-91, Middlesex Hospital, Wesleyan University, and Main Street's award-winning dining, boutique shops, and community events. Move right in and enjoy easy living-schedule your private tour today!

27 W Silver St Unit 27, Middletown
79 Rising Trail Dr Unit 79, Middletown
$220,000
3 Beds ⋅ 2 Baths ⋅ 24219989 MLS ⋅ Beacon Hill Towne Homes BLDG.
This three-level townhouse-style condo pairs an open first floor made for entertaining with a private backyard of your own. Gather around the fireplace, head outside to relax, or spend a summer afternoon by the community's in-ground pool. On the third floor, a versatile bonus room gives you extra space for a home office, guests, or storage. A one-car garage beneath the unit rounds out the home.

79 Rising Trail Dr Unit 79, Middletown
223 Carriage Crossing Ln Unit 223, Middletown
$195,000
1 Beds ⋅ 1 Baths ⋅ 24218069 MLS ⋅ Carriage Crossing BLDG.
Why rent when you can build equity ... This is an excellent opportunity to own this third floor, one bedroom, condo in desirable Carriage Crossing condo complex. This unit has newer HVAC and 2025 hot water heater. Awesome easy living with everything you need in your community. The Carriage Crossing complex offers in-ground pool, sauna, hot tub, tennis court, fitness center and racquetball court. No more gym fees when you have it all in your community. It is also conveniently located close to restaurants, shopping and major highways (I91 and Route 9). Schedule your showing today! Be in your own home for the holidays.

223 Carriage Crossing Ln Unit 223, Middletown
6 Countryside Ln Unit 6, Middletown
$249,900
2 Beds ⋅ 2 Baths ⋅ 24218923 MLS ⋅ Cedar Ridge BLDG.
Exceptional tri-level townhouse end unit now available in Cedar Ridge; an uncommon community located within the rural confines of South Farms in Middletown, CT. There's ready access to Middletown's business, retail and dining options, just a few miles away. Need to be close the fast track? It's just close enough. What's so appealing about this townhouse besides great value? Let's start with lots of windows adding bright light throughout. Did I mention those are Harvey vinyl replacement windows throughout. There's newer oak hardwood flooring found throughout the LR/DR and second floor hall and bedrooms. A nicely appointed kitchen has stainless appliances, pantry closet, half bath access and rear door to a vinyl deck with a grassy view. The upper floor gives way to two large bedrooms. The primary bedroom is generously proportioned with its own entrance to the full bath. The second bedroom offers nice storage and backyard view that's green too! An uncommon feature is a full attic with pulldown stairs access and abundant storage. Finish your tour of this home in the partially finished lower level. It has newer plus carpeting and fresh paint. Lots of flexibility here: need a craft room, workout space or family room? It includes a laundry closet with a washer and dryer. An unfinished area to the rear allows for more storage space, a newer electric hot water heater and access door to the exterior through a shared stairwell to a Bilco door to the back yard area.

6 Countryside Ln Unit 6, Middletown
201 College St Unit 20, Middletown
$179,000
2 Beds ⋅ 2 Baths ⋅ 24219890 MLS ⋅ Hamlin Court BLDG.
Location, lifestyle, and convenience come together in the heart of Middletown! Just steps from Wesleyan University and a short stroll to bustling Main Street, this 2-bedroom, 1.5-bath townhouse-style condo puts you within walking distance of some of Central Connecticut's best restaurants, coffee shops, boutiques, entertainment, and nightlife. Inside, approximately 1,150 square feet of living space offers a comfortable, functional layout with an open living and dining area, updated flooring, fresh paint, and a terrace perfect for enjoying your morning coffee or unwinding after a long day. Upstairs, two spacious bedrooms, generous closet space, and convenient in-unit laundry provide the everyday comforts of home. Newer windows, updated kitchen appliances, a dedicated storage unit, and assigned parking add practicality. Whether you're seeking a primary residence in a walkable neighborhood or an investment property in a desirable rental location, this townhouse offers the best of both worlds. Its proximity to Wesleyan University, Middlesex Hospital, downtown employers, and local businesses creates appeal for a broad range of prospective tenants. Rental comps support $2,300/month, this is an opportunity to own in one of Middletown's most convenient locations.

201 College St Unit 20, Middletown
162 Trolley Crossing Ln Unit 162, Middletown
$189,900
2 Beds ⋅ 2 Baths ⋅ 24219822 MLS ⋅ Trolley Crossing BLDG.
Step into effortless single-level living at 162 Trolley Crossing Lane. The interior centers around a fluid, sunlit layout finished in crisp, contemporary tones. Anchoring the main living space, the chef's kitchen features handcrafted timber cabinetry, modern appliances, and a casual counter-height bar ideal for hosting. Adjacent dining and lounge spaces are grounded by fresh hard-surface flooring, framed by high-efficiency windows and glass sliders that lead out to a private, sheltered terrace with dedicated storage-a front-row seat to sweeping evening skies. Down the hall, dual quiet suites are fitted with plush carpeting and expansive walk-in wardrobes, with the primary bedroom featuring its own en-suite half bath. Day-to-day overhead is streamlined, as the monthly association fee covers heating and hot water, consolidating your utility footprint down to a single account. Outside your door, find secluded, pet-welcoming grounds just minutes from regional trail networks, dining hubs, retail, and major commuter corridors. Schedule a private walkthrough to experience it in person.

162 Trolley Crossing Ln Unit 162, Middletown
92 Cynthia Ln Unit E2, Middletown
$200,000
2 Beds ⋅ 1 Baths ⋅ 24219774 MLS ⋅ Quail Run Village BLDG.
Tucked away at the back of the Quail Run Villages complex, where the bustle of everyday life gives way to a peaceful, wooded backdrop, 92 Cynthia Lane, Unit E-2 offers a little sanctuary to call your own. This inviting 2 bedroom townhouse blends comfort, convenience, and tranquility in a setting that feels wonderfully removed from it all. Step inside to a welcoming, open concept living and dining area that flows effortlessly into the kitchen, complete with a brand new backsplash. Sliding glass doors lead to a newly constructed pressure treated deck overlooking a beautiful backdrop of trees. Imagine slow mornings with coffee in hand, quiet evenings unwinding, and the simple pleasure of having nature just outside your door. Upstairs, two comfortable bedrooms and a full bath with brand-new flooring offer a restful retreat. The lower level provides a new washer and dryer, additional storage, and direct access to your one car garage. While this home feels tucked away from the world, shopping, dining, and Route 9 in Cromwell are just minutes away, along with the charming restaurants and vibrant atmosphere of downtown Middletown. Peaceful surroundings, easy living, and convenience when you want it. Welcome to 92 Cynthia Lane, where coming home feels like getting away.

92 Cynthia Ln Unit E2, Middletown
127 Carriage Crossing Ln Unit 127, Middletown
$245,000
2 Beds ⋅ 2 Baths ⋅ 24218636 MLS ⋅ Carriage Crossing BLDG.
Pride of Ownership and well-appointed desirable first-floor end-unit offering comfort, convenience, and an abundance of amenities! Freshly painted throughout, this bright and inviting home features beautiful, vaulted ceilings and a cozy fireplace in the living room, creating the perfect space to relax and unwind. Offering 2 spacious bedrooms, each with its own full bathroom, this home provides comfort and privacy for residents and guests alike. Additional features include an HVAC system approximately 3 years young water heater approximately 6 years for added peace of mind. Enjoy the added convenience of parking DIRECTLY in front of the unit. The community offers an impressive array of amenities, including a clubhouse, swimming pool, fitness center, and tennis and racquetball facilities. Brand-new exterior security cameras have recently been installed throughout the complex, and the pet-friendly community is an added bonus! Conveniently located near shopping, restaurants, and Wesleyan University, with easy access to Route 9 and I-91. Also ideally situated for access to Middlesex Hospital, Yale New Haven Hospital, and Hartford Hospital. With its desirable first-floor end-unit location, private bedroom bathrooms, thoughtful updates, wonderful community amenities, and convenient location, this home is an excellent opportunity to enjoy comfortable, low-maintenance living!

127 Carriage Crossing Ln Unit 127, Middletown
38 Farm Hill Rd Rd, Middletown
$284,900
2 Beds ⋅ 1 Baths ⋅ 24217053 MLS
Opportunity awaits on Farm Hill Rd, just off South Main Street. This 2-bedroom, 1-bath home offers convenient one-floor living and sits on a desirable corner lot with room to grow. Expand your living space by finishing the basement or converting the attic. The detached garage, built in 2006, is a standout feature, ideal for a workshop, mechanic projects, or rental income. The home needs some TLC, but the bones are solid, making it a great canvas for an investor or first-time buyer ready to add value and make it their own. Enjoy easy access to shopping and nearby Pat Kidney Sports Complex. Come see the potential for yourself!

38 Farm Hill Rd Rd, Middletown
675 Newfield St Unit 10, Middletown
$270,000
2 Beds ⋅ 2 Baths ⋅ 24219462 MLS ⋅ Newfield Commons BLDG.
Welcome to Newfield Commons in Middletown-a fantastic townhouse-style condo that is perfect for first-time home buyers or empty nesters looking for comfort, convenience, and minimal maintenance living. This spacious 2-bedroom, 1.5-bath townhouse style condo offers an open and inviting layout with Pergo flooring on the first level, and a bright living room that flows seamlessly to your private Trex deck. Enjoy relaxing or entertaining with tranquil views of brush and trees and never worry about upkeep thanks to the maintenance-free design. Step inside from your attached garage, offering ultimate convenience, especially during New England winters. The newer stainless-steel appliances in the kitchen make cooking a delight, while abundant storage-including a walk-in closet, a large hallway closet, and finished basement-keeps everything organized. The upstairs full bath features double sinks for extra functionality. Additional highlights include a newer hot water heater (replaced in December 2023), a heat pump and central air system serviced in September 2026, and a finished walkout basement perfect for a home office, gym, or rec room. The large primary bedroom overlooks peaceful woods for added privacy and serenity. Located just a short drive from shops, highways, and all three school levels within a mile, this condo is convenient and family friendly. Enjoy central air in the warmer months and reasonable HOA fees of just $315/month. Do not miss your chance!

675 Newfield St Unit 10, Middletown
Start Your Search

IDX information is provided exclusively 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. Information is deemed reliable but is not guaranteed. © 2026 State-Wide Multiple Listing Service. All rights reserved. Data Last Updated:

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.

How much is your home worth?

Get instant property value now!