Middletown Homes under $500,000

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Newest Middletown Homes under $500,000

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

$369,900

3 Beds ⋅ 2 Baths ⋅ 24220851 MLS

Welcome to 3 Lyman Drive! From the moment you walk through the door, this 3-bedroom, 1.5-bath Colonial has a way of making you feel right at home. Located in a beautiful, quiet neighborhood, this home offers a comfortable and inviting layout with plenty of space to enjoy. The living room features a cozy fireplace that makes it the perfect place to relax and unwind. The updated kitchen includes newer appliances and opens directly to the dining room, with easy access to the back deck and fenced-in backyard, making it a great space for everyday living and entertaining. Upstairs, you'll find three spacious bedrooms, including a large primary bedroom with a walk-in closet. An additional office or recreation room offers flexibility for a home office, playroom, or extra living space. The unfinished basement provides plenty of storage and the potential for even more finished space down the road. With its welcoming feel, functional layout, and wonderful neighborhood setting, 3 Lyman Drive is the kind of place that truly feels like home. Come see for yourself!

3 Lyman Dr, Middletown

$325,000

2 Beds ⋅ 2 Baths ⋅ 24220803 MLS

Terrific updated home in a quiet and convenient East side location with easy access to highways and the Downtown district. The kitchen is nicely updated with gray cabinets, granite counters/tile backsplash, stainless appliances and a nice large undermount sink. From the dining area there are French doors out to the rear deck that overlooks the nice level rear yard. The main floor has hardwood throughout, except tile in the beautiful modern full bathroom. The lower level has a fireplace, luxury vinyl plank floors, a half bathroom with laundry, and a walk out to the garage. Outside the yard features a garden bed, a large shed and easy maintenance plantings. Solar panels to offset the electrical expense are leased and will transfer with sale. This home is clean and tight, and really is move in ready. Professional photos and floor plan coming soon

333 Bartholomew Rd, 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

$379,900

3 Beds ⋅ 2 Baths ⋅ 24220713 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 sunroom serves as a perfect home office, reading nook, or plant oasis. Outdoor Entertaining: The sunroom 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

$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

$399,000

4 Beds ⋅ 4 Baths ⋅ 24220282 MLS

Exceptional value-add investment opportunity in Middletown! This mixed-use property offers two existing residential apartments and a spacious ground-floor retail space with the potential to convert into two additional, larger residential units, creating a four-family investment property. The upper level features two one-bedroom, one-bathroom apartments, each equipped with washer/dryer hookups and electric water heaters. Additional property highlights include oil heating, solar panels serving all units, a newer roof, and ample off-street parking with convenient front, side, and rear driveway access. All existing appliances are included, excluding washers and dryers. The expansive ground-floor retail space presents an excellent opportunity for investors or developers looking to maximize rental income and build equity through conversion. The City of Middletown has provided preliminary verbal feedback indicating that a four-unit residential conversion may be possible, subject to formal application, required approvals, permits, and inspections. Other four-unit residential properties in the surrounding area further demonstrate the neighborhood's multifamily character.

390 S Main St, 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

$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

$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

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Middletown Homes under $500,000

Newest Middletown Homes under $500,000

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How much is your home worth?