Middletown, CT Homes for Sale under $500,000

This classic 1900 Colonial at 103 Prospect Street offers a chance to bring new life to a well-loved home in a convenient Middletown location. With 1,160 square feet of living space, three bedrooms, and two full baths, the layout is simple and functional, ready for someone with vision to make it their own. The home does require work, making it a great project for investors, renovators, or buyers

Carl Guild Carl Guild & Associates

Experience one-floor living at its finest at Nathan Hale Estates, a private-way community nestled in Middletown, Connecticut, built by Silvin Homes and offering modern comfort, quality craftsmanship, and peaceful surroundings. Entering from the covered front porch, you're welcomed into a thoughtfully designed layout. Features include a convenient laundry room and two well-appointed secondary

Jenna Talbot RE/MAX One

Welcome home to 193 Ridge Rd, a 3-bedroom, 2-full-bath gem, lovingly updated but full of warmth and charm. Step onto the large front porch and you'll feel it - this one's different. The updated kitchen shines with granite counters, soft-close cabinetry, and a generous pantry, ready for morning coffee or holiday hosting. The dining and living rooms stretch out with beautifully refinished hardwood

Wesley Krombel Real Broker CT, LLC

This beautifully maintained Colonial, tucked away on a quiet cul-de-sac, in the highly sought after Riverbend development is a must-see! Filled with natural light and abundant storage, this home also features two spacious decks for relaxing and entertaining. The sun-filled eat-in kitchen boasts soaring ceilings that extend to the second floor, creating an open and airy feel. Large windows flood

Maria Gaudet Lamacchia Realty

Lovingly cared for home set in a beautiful yard with mature plantings and natural rock outcroppings. Lots of space in this charming home including a sunroom surrounded by windows that opens to a deck. The eat-in kitchen with Corian counters and tile backsplash leads to the formal living and dining rooms. Three bedrooms, including the primary that is connected to a full bath, complete the main

Siobhan McLaughlin William Raveis Real Estate

Turn-key home in the sought-after Riverbend Community in Middletown's desirable Westfield neighborhood offers suburban tranquility with excellent convenience. Inside, soaring ceilings grace the living and dining areas, a fireplace adds warmth to the living room, and hardwood floors flow through the main spaces. Large dining area flows to the kitchen and living room, perfect for entertaining. The

Linda Edelwich William Raveis Real Estate

Welcome home to this well-maintained 2-bedroom, 1-bath ranch offering easy one-level living and the perfect condo alternative. The inviting floor plan features a spacious living room, formal dining room, and an updated kitchen complete with stainless steel appliances. Beautiful hardwood flooring flows throughout much of the home, while recent updates, including a newer furnace, new hot water

Ellen Paklos William Raveis Real Estate

Bring your growing family to this spacious colonial! 4 bedrooms with two on first floor. 2 full baths. Eat in kitchen. Living room with fireplace. Spacious room at top of staircase can potentially be 5th bedroom! Hardwood floors thru-out. Walk out basement to level yard. Deck. Whether you are a car enthusiast or need a lot of storage space, you will love the oversized detached 2 car heated garage

Wilson Lamas Regency Real Estate, LLC

Nestled in the highly sought-after Wesleyan Hills community, this well-maintained and affordable 3-bedroom condo offers the perfect blend of comfort, convenience, and privacy. Featuring an open floor plan, the home boasts an updated kitchen that flows seamlessly into the living and dining areas, creating an inviting space for everyday living and entertaining. A sliding glass door leads to your

Santo Gulino William Raveis Real Estate

Rarely does a home blend historic character, creative energy & walkable in-town living so effortlessly. Nestled on a beautifully landscaped corner lot just moments from Wesleyan University, vibrant downtown Middletown & the Connecticut River waterfront, this thoughtfully updated early-1900s home offers warmth, flexibility & timeless appeal. Featuring 3 bedrooms, 2 full baths & a versatile

Michelle Mazzotta eXp Realty

Whether you're searching for your next home or a low-maintenance investment opportunity, this townhouse-style condo is worth a look! Offering 2 bedrooms, 1.5 bathrooms, and a functional open layout, the main level features a spacious living room that flows into the dining area and kitchen, creating a comfortable space for everyday living. Upstairs you'll find both bedrooms, convenient in-unit

Doug Hagen Starr Team at LPT Realty

*Back on the market due to the previous buyer already owning a unit.* Welcome to 5 Carriage Crossing, a desirable first floor end-unit condo in the welcoming Carriage Crossing community of Middletown, CT. This well maintained 2 bedroom, 2 bath condominium offers the perfect blend of comfort, convenience, and low maintenance living. Filled with natural light, the spacious floor plan provides an

kathleen mullins Real Broker CT, LLC

Welcome home to this beautifully remodeled brick ranch, perfectly situated in a highly desirable neighborhood. This move-in-ready home offers three spacious bedrooms and two full bathrooms, combining classic charm with modern updates throughout. Step inside to find a welcoming living room featuring one of two cozy fireplaces, creating the perfect space for relaxing or entertaining. The

Heather Salafia Eagle Eye Realty PLLC

Beautifully updated home tucked away on a quiet cul-de-sac offering the perfect blend of comfort, functionality & major recent improvements. The open floor plan creates a bright, inviting feel, complemented by hardwood floors throughout the main level. The kitchen was updated in 2022 with new cabinetry, quartz countertops & a clean modern look ideal for everyday living. The flexible layout

Michelle Mazzotta eXp Realty

Nestled in the highly desirable South Farms neighborhood, this well-maintained home is filled with quality features and timeless appeal. Car enthusiasts and hobbyists will appreciate the impressive 4-car garage, offering exceptional space for vehicles, storage, or the perfect workshop. The spacious eat-in kitchen features granite countertops, abundant cabinetry, and generous workspace for cooking

James Foley William Raveis Real Estate

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

Amiyra Beauduy Century 21 Scala Group

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

Levi Judqin Brass Moon Realty

It has style, it has grace, it has a new roof (3 years old) - you will absolutely love this place!! THIS is the cape you've been waiting for! Ideal floorplan - the primary bedroom on the first floor faces the backyard; the relaxing living room has a wood burning fireplace; the renovated full bathroom has a bathtub; the beautifully modernized kitchen is fully applianced and the separate dining

Vaiva Baltonis Coldwell Banker Realty

Beautiful Colonial tucked away on a quiet cul-de-sac offering comfort, space, and modern updates. The inviting living room features a large picture window and cozy wood-burning fireplace, creating the perfect gathering space. Updated kitchen includes granite countertops, with plenty of cabinet space, and easy access to the deck - ideal for cookouts and outdoor entertainment. The main level also

Brenda Carocari Realty ONE Group Connect

Welcome to this inviting contemporary home in Middletown offering the perfect blend of comfort, style, and convenience. This well maintained 4 bedroom, 2 bath residence features 1,328 square feet of thoughtfully designed living space ideal for today's lifestyle. Step inside to discover an updated kitchen with modern finishes, providing a functional and attractive space for everyday living and

Keith Murphy Innovative Properties

Welcome to 116 Schuyler Ave! This home is conveniently located on a dead end close to Middletown's shopping and restaurant district, highways, parks and more. This 3 bedroom home was built in 1890 and carries a lot of colonial charm like the incredible hardwood floors throughout, a fully finished attic, and built-in cabinets. The Main level has a full bathroom with a walk-in shower, living room,

Moira Dill mygoodagent

Some homes are built to impress. Others are built to be lived in. This extraordinary farmhouse does both. A charming covered front porch, framed by mature perennial gardens that bloom with the seasons, welcomes you home. It's the kind of place where evenings are best spent watching breathtaking sunsets as the sounds of nature replace the noise of the day. Inside, rustic charm blends seamlessly

Amanda Zorovich New Roots Realty

Welcome home to this beautifully renovated 3-bedroom, 2-bathroom raised ranch in Wesleyan Hills, where all the major work is already done for you. This move-in ready home features a brand new roof and new efficient boiler, giving you years of worry-free ownership and energy savings. The heart of the home is a stunning new kitchen with crisp white shaker cabinets, quartz countertops, and modern

Atif Seyal RE/MAX Heritage

Come see this beautiful freshly painted two bedroom, 2 bath remodeled unit which has Corian countertops and white cabinetry for a bright and light kitchen. All kitchen appliances are stainless steel and the flooring is tile. Walk into the dining room/living room with tile flooring and overhead fan to the slider for some extra views of the CT. River! Both bedrooms have Bamboo wood flooring with

Sally McMahon William Raveis Real Estate

Buyer Financing Fell Through - Enjoy one of only a select few of the largest townhouse end units in the complex offering 1,109 square feet of vast living space. Nestled in a popular, well-maintained community, this home combines convenience, comfort and peace of mind with nothing to do but unpack and enjoy. Recent complex-wide improvements include new roads with abundant guest parking, new

Chris Hogan Century 21 Classic Homes

Turnkey multifamily 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

Amiyra Beauduy Century 21 Scala Group

Welcome to 824 Randolph Rd, Middletown! You'll fall in love with this beautiful ranch offering the convenience of one-floor living, a two-car garage, and an inviting in-ground pool with patio that's perfect for relaxing or entertaining. Step inside to find a bright, spacious living room with a beautiful fireplace, an eat-in kitchen with stainless steel appliances, and a dining room featuring a

Giulia Terese Hagel & Assoc. Real Estate

Welcome home to this sought-after condo complex at Carriage Crossing, where you will find this two bedroom two full bath unit, with open concept space. The galley kitchen has pantry. Both bathrooms have granite countertops and soft close cabinetry. In unit washer and dryer. Living room has a cozy wood-burning fireplace. Primary bedroom has a walk-in closet, and both bedrooms have their own full

Karen Murphy Berkshire Hathaway NE Prop.

* INVESTORS ONLY* FULLY rented, well-maintained and spacious two-family home, perfect for investors. Each unit offers 2-3 bedrooms, a full kitchen, living areas, and separate utilities. Features include updated front and back porch. Private backyard with entertainment and garden space. Full basement for plenty of storage. Updated water heaters for both units and main sewer were replaced less than

Shannon Driscoll Carl Guild & Associates

Experience one-floor living at its finest at Nathan Hale Estates, a private-way community nestled in Middletown, Connecticut, built by Silvin Homes and offering modern comfort, quality craftsmanship, and peaceful surroundings. Entering from the covered front porch, you're welcomed into a thoughtfully designed layout. Features include a convenient laundry room and two well-appointed secondary

Jenna Talbot RE/MAX One

Fabulous Opportunity to Own One of The Most Desirable Units in the Complex!! This Rarely Available End Unit Offers Exceptional Privacy & the Peaceful Setting You've Been Waiting For!! Beautifully Maintained, Move-In Ready Townhome Located In the Highly Sought After Trolley Crossing Community!! Freshly Painted Throughout Including Walls, Trim & Ceilings Creating a Bright & Inviting Feel!! New

MaryJo Dunn William Raveis Real Estate

Welcome to this charming Colonial-style home set on a generous 3.3-acre lot, offering the perfect blend of comfort, space, and modern updates. The exterior showcases classic appeal with a welcoming front entry & an attached 2 car garage, all surrounded by open land that provides privacy and endless possibilities. Step inside to discover a beautifully updated kitchen featuring stainless steel

Michelle Mazzotta eXp Realty

Welcome to this spacious move in ready four bedroom, two bath home located in the desirable Highland section of Middletown. This well maintained property features an updated kitchen with granite countertops and stainless steel appliances, offering both style and functionality. The first floor includes laminate flooring throughout the main living areas, while the bedrooms feature carpeting for

Keith Murphy Innovative Properties