Browse All Middletown CT Between $400K - $500K Properties for Sale

Welcome to 1511 Country Club Road, a remarkably versatile property offering 4-bedroom functionality situated on an expansive 1.25-acre parcel on a peaceful, non-through street. A charming entry introduces the main Cape, which features two comfortable bedrooms, a full bath, and an upper loft ready to serve as a home office, recreation room, or potential third bedroom. Seamlessly connected yet private, the dedicated in-law/secondary living quarters boast their own bedroom and an additional loft space currently utilized as a primary suite-ideal for multi-generational living, extended guests, or a dedicated private wing. Peace of mind comes built-in with a brand-new septic system. Outside, the sprawling acre-and-a-quarter grounds provide mature greenery, a fenced-in play/pet area, and boundless room for entertaining, gardening, or outdoor expansion. A rare combination of privacy, acreage, and adaptable living space.

1511 Country Club Rd, Middletown

$450,000

3 Beds ⋅ 3 Baths ⋅ 24217472 MLS

One level living with room for expansion in this spacious ranch. Three bedrooms and 3 full baths with and oversize mudroom between the house and garage give you lots of options. Oversized 2 car garage gives you plenty of room for storage in the event you may want to finish off the lower level of this home. Completely remodeled home allows you peace of mind knowing all you have to do is move in. New Windows, new roof, new gutters, new flooring in kitchen and living room and remaining floors refinished The kitchen offers lots of countertop space, cabinets, quartz countertops, island, stainless steel appliances and room for the dining table. Recessed lighting and tile back splash finish off the detail. All three bedrooms are roomy and the master bedroom offers a fully renovated master bath with tiled walk in shower. Keep the open fireplace or add a pellet or wood stove to give you that New England feel while keeping the chill off. The basement would make for great additional living space as there is already a full bath there. New Bilco door and steps to basement. Updated mechanicals including new gas boiler, city water and sewer will give you peace of mind. New roof, windows and fresh paint throughout. There is a shared driveway however there is room from survey (in photos) that was done to have a private driveway. Located near the heart of Middletown, with so many options when it comes to dining, shopping or entertainment.

404 Newfield St, Middletown

$425,000

3 Beds ⋅ 2 Baths ⋅ 24216846 MLS

Don't miss this pristine and charming Gambrel Colonial on a perfect level half acre, offering a quiet setting, gorgeous views, generous outdoor living spaces, and tasteful renovations in every room. Infused with beautiful natural light, this right-sized home offers 1718 sf with loads of windows (11 have been replaced by this owner), 3 bedrooms, and 2 bathrooms. The main floor space takes full advantage of its front-to-back design with two living/family rooms anchored by a central combined kitchen and dining room. The kitchen was renovated in 2026 with new LifeProof flooring, solid surface counters, subway tile backsplash, paint, and lighting. With separate coffee bar area and pantry and cool exposed brick, the kitchen offers great storage and is large enough for a long dining table, and can accommodate an island too! The family room features a wood-burning fireplace for cozy nights. The second floor offers a full bathroom and 3 generously sized bedrooms and spacious hallway, all updated with paint and featuring new flooring. The large remodeled full bath (2024) features marble tile tub surround and gorgeous hexagonal floor tile. More to love: half bath (remodeled 2023); new A/C (2023); new paver patio, garage doors, and shed (2021); new siding (2020); full basement; underground pet fence; and generator-ready.

400 Coleman Rd, Middletown

$474,900

3 Beds ⋅ 3 Baths ⋅ 24215505 MLS

Welcome to 126 Rolling Green in Middletown! This spacious Ranch-style home combines comfortable one-level living with versatile additional space and an inviting setting in a fantastic neighborhood. The main level features three bedrooms, two full baths and a convenient laundry room, offering an easy and functional layout for everyday living. Step inside to discover abundant natural light and a formal dining room with vaulted ceilings and an elegant Palladian-style window. The spacious eat-in kitchen offers extensive cabinetry, recessed lighting, and a large pantry, opening to a versatile adjoining room with vaulted ceilings, a wine rack, and beverage refrigerator - perfect for entertaining or everyday relaxation. The living room features a natural gas fireplace, creating a warm and welcoming gathering space. The primary bedroom offers a large walk-in closet and an en-suite bathroom with a stand-up shower and Jacuzzi-style tub. Two additional bedrooms and two full bathrooms complete the main-level living space.

126 Rolling Grn, Middletown

$419,900

3 Beds ⋅ 2 Baths ⋅ 24216288 MLS

This meticulously maintained raised ranch offers 2,712 square feet of total living space on a beautiful 0.41-acre lot. Vaulted ceilings with skylights enhance the living and dining rooms, while hardwood floors flow through both spaces and the eat-in kitchen. A wood-burning fireplace adds warmth and character to the living room. The up-dated kitchen features granite countertops and stainless steel appliances. Three bedrooms and two full baths include a primary bath with a shower. Six-panel raised doors add a classic touch throughout the home. The lower level provides additional living space with a wood-burning stove, a pine ceiling, and a separate laundry room. Central air conditioning, a newer roof, an attached two-car garage, and pull-down attic storage offer comfort and convenience. A stone walkway and beautiful backyard enhance the outdoor setting. Conveniently located near highways, this move-in-ready home is ready to welcome its next owners.

14 Cimarron Rd, Middletown

$425,000

3 Beds ⋅ 3 Baths ⋅ 24215323 MLS

What a beautiful opportunity to own in Autumn Meadows, a 55+ community in bustling Middletown. Featuring hardwood floors throughout both the main level and the lower level in-law apartment, this property offers comfortable living, versatile space and a wonderful layout. The main level features two bedrooms and two full bathrooms, including a spacious primary suite complete with a full bath and walk-in closet. The large kitchen boasts stainless steel appliances and granite countertops, while the convenient main level laundry is tucked away in a hallway closet. Just off the living room, a newer deck overlooks open space, providing a lovely spot to relax and enjoy the outdoors. The lower level in-law apartment offers excellent additional living space, featuring one bedroom, kitchen, dining area and living room with cozy free standing gas fireplace. A deck off the lower level provides another outdoor retreat, making this space ideal for extended family or guests. With its inviting layout, beautiful hardwood floors, multiple outdoor living spaces and flexible in-law accomodations, this home offers a wonderful opportunity to enjoy easy living in a 55+ community.

32 Autumn Ln Unit 32, Middletown

$469,000

3 Beds ⋅ 3 Baths ⋅ 24212932 MLS ⋅ Autumn Meadows BLDG.

Welcome to Autumn Meadows, where beautiful improvements and versatile living come together! This freestanding 3-bedroom, 3-full-bath home offers no shared walls, An inviting open floor plan creates a wonderful sense of space, while three main-level bedrooms, including the primary suite, provide the ease and convenience of one-level living. The updated kitchen features quartz countertops, a generous breakfast bar, newer stainless steel appliances and abundant cabinetry. Gleaming hardwood floors, crown molding and a handsome propane fireplace enhance the living and dining areas. Sliders from the living room open to a spacious TimberTech deck overlooking a picturesque natural meadow with seasonal birdlife. Remodeled bathrooms feature stylish vanities and beautiful quartz and tile showers. The finished lower level offers over 600 square feet of additional living space with heat, central air, a full bath and hookups for a potential kitchenette. Imagine a guest retreat, recreation room, home office or possible second primary suite! Approximately 1,000 square feet of unfinished basement provides generous workshop, mechanical and storage space. The attached finished two-car garage features epoxy flooring and access to the lower walkout level. A new central A/C system installed August 2026 adds peace of mind. Convenient to downtown Middletown, Wesleyan University, Middlesex Health and major commuting routes. A truly special place to call home!

38 Autumn Ln Unit 38, Middletown

$460,000

3 Beds ⋅ 1 Baths ⋅ 24214279 MLS

Step Back in Time - with Comfort and Charm! Built in 1881, this lovingly maintained antique home is filled with character, warmth, and timeless beauty. Nestled on 2.62 acres of peaceful, picturesque grounds, this special property offers a rare blend of history, privacy, and possibility. Step inside and discover 1,964 sq. ft. of inviting living space where the craftsmanship of a bygone era shines through. Rich woodwork, vintage hardware, charming built-ins, and delightful architectural details create an atmosphere that simply cannot be replicated in today's homes. Each room tells a story, offering warmth, character, and a sense of nostalgia. The partially finished attic offers exciting possibilities for expanded living space, a creative studio, or a home office, allowing the next owner to imagine what could be. Outside, enjoy the beauty of mature trees, picturesque surroundings, and plenty of room to roam. Whether relaxing in the peaceful setting, enjoying nature, or envisioning your own outdoor retreat, the possibilities are endless. A detached garage and charming garden shed complement this wonderful property. More than just a house, this is a home that has been cherished through the years and is ready for its next chapter. Warm, welcoming, and full of soul, it awaits someone who appreciates the beauty and individuality of an antique home. Come experience the magic of this 1881 gem.

1040 Washington St, Middletown

$499,000

3 Beds ⋅ 3 Baths ⋅ 24214047 MLS

Welcome to 12 Brookview Lane, located in Middletown's desirable Westfield neighborhood! This beautifully maintained 3 bedroom, 2.5 bathroom home offers a wonderful combination of space, style, and functionality. Step inside to discover inviting, spacious living areas accented by beautiful hardwood floors. The stylishly updated kitchen features an open layout that flows effortlessly into the surrounding living space, creating an ideal setting for both everyday living and entertaining. A generously sized bonus room offers endless possibilities, whether you envision a home office, playroom, media room, or additional gathering space. The partially finished basement provides even more flexible living space to suit your needs. With its thoughtful layout, tasteful updates, and versatile spaces, this home offers comfort and convenience in a fantastic Middletown location. Come see all that 12 Brookview Lane has to offer!

12 Brookview Ln, Middletown

$424,900

3 Beds ⋅ 2 Baths ⋅ 24213654 MLS

Lovingly updated and maintained one floor living featuring a roomy eat in kitchen, living room with fireplace. A large primary bedroom with French doors to the deck, provides a large walk in closet an en suite bath with walk in shower and jet tub. The floors throughout the principal rooms of the home are hardwood with the exception of the kitchen and baths with tile flooring. There are two other bedrooms and a family bath also with a walk in shower. The current owners added a one car detached garage, installed a new oil tank and added a very useful workbench in the basement section where double doors allow for entry of their sit down mower. There is a nest system to make off site adjustments to heat and A/C and exterior cameras that are not currently connected to police, fire departments but could be. The deck is two tiered, has a gazebo and is the perfect spot for friends and families to gather. The rear yard is fully fenced for those who have pets that can enjoy a protected outdoor area. Please allow at least 2-3 hours notice to show.

526 Westfield St, Middletown

$440,000

3 Beds ⋅ 2 Baths ⋅ 24212850 MLS

Welcome to 43 Jefferson Ave, Middletown! This charming 3-bedroom brick ranch offers comfort, space, and convenience in an established neighborhood. The spacious living room features beautiful hardwood floors and a cozy fireplace. The generously sized kitchen and dining area offer ample cabinetry, a center island, and direct access to the rear deck. All three bedrooms are conveniently located on the main level with hardwood flooring and plenty of natural light. The finished lower level adds valuable living space with a recreation/family room and second fireplace, half bath, laundry area, workshop, and storage-perfect for a home office, gym, entertainment area, or hobbies. Outside, enjoy the spacious rear deck, private driveway, detached one-car garage with additional storage space, and well-maintained yard. A newer roof adds peace of mind, while the classic brick exterior provides timeless curb appeal. Conveniently located near shopping, restaurants, schools, parks, downtown Middletown, and major commuting routes. With its easy one-level living, flexible lower-level space, garage, deck, newer roof, and desirable location, 43 Jefferson Ave is ready for its next owner. Schedule your private showing today!

43 Jefferson Ave, Middletown

$415,000

3 Beds ⋅ 2 Baths ⋅ 24212078 MLS

Beautiful views, abundant natural light, and distinctive architectural details define 972 Ridgewood Road. This three-bedroom, one-and-a-half-bath ranch pairs hardwood floors throughout the main living areas with a kitchen renovated in 2018, featuring granite countertops, custom storage drawers, and updated appliances. The adjoining dining room centers on a wood-burning fireplace, while two sets of French doors open to a striking living/sitting room with cathedral ceilings, an inviting setting for entertaining, a library, or a private office. The mostly finished walkout lower level, finished in 2020, offers additional living space, a half bath, laundry, and separate utility and storage areas. A three-car garage accommodates vehicles and hobbies, while the generous yard invites gardening, gathering, and enjoying the views. Thoughtful improvements include double-hung replacement windows (2019), picture windows and solar installation (2020), a UV water filter (2021), and a well expansion tank (2020). A roof and electrical panel replaced in 2017, plus a septic tank and leaching field installed in 2016, round out the updates. Enjoy Middletown's Main Street dining and shopping and the trails and waterfalls of Wadsworth Falls State Park. Schedule your showing to experience this home's memorable blend of character, light, and views.

972 Ridgewood Rd, Middletown

$425,000

3 Beds ⋅ 3 Baths ⋅ 24211740 MLS

Welcome to 118 Camp Street, nestled in Middletown's highly desirable Westfield district! Situated on a beautiful, expansive lot, this well-built 3-bedroom, 2.5-bath ranch offers the ease of true single-level living combined with major mechanical peace of mind. Key capital improvements are already in place, including efficient central air conditioning and a roof that is just 3 years old. The main level welcomes you with comfortable, sunlit living spaces and a functional floor plan designed for effortless everyday living and entertaining. The bedroom wing features three well-proportioned rooms, highlighted by a private primary suite complete with a walk-in closet and dedicated en-suite bath. Downstairs, the finished lower level dramatically expands your living footprint and versatility. Outfitted with a generous secondary living room, a full second kitchen, and a convenient half bath, this self-contained space is tailor-made for guest accommodations, multi-generational living, or the ultimate recreation and game room. Outside, the picturesque property provides plenty of open green space for gardening, outdoor gatherings, pets, or weekend relaxation in an established neighborhood setting. With solid construction, low-maintenance mechanicals, and a premier Westfield location close to schools, parks, and commuter routes, this classic ranch is ready for you to move in and personalize to your lifestyle!

118 Camp St, Middletown

$415,000

3 Beds ⋅ 2 Baths ⋅ 24204682 MLS

This home is located in a sought-after section of Westfield near the Cromwell town line convenient to highways.Vaulted ceilings in the living room/family room/dining area create a bright modern feeling perfect for entertaining. All are connected to an eat-in kitchen where you can sit at the island and keep the cook company. The two bedrooms are both comfortable retreats. The lower level has a large third bedroom with privacy for guests or teens. You'll enjoy the extra room with a full walk-out ideal for games, exercise, parties and gatherings. All this within minutes of commuter highways, shopping, and recreation. You'll love to call this home!

55 Moss Gln, Middletown

$435,000

3 Beds ⋅ 2 Baths ⋅ 24203125 MLS

This charming three-bedroom, one-and-a-half-bath English Tudor sits on a landscaped corner lot and offers a wonderful mix of classic details and modern updates. The beautifully updated kitchen features white and gray cabinetry, quartz countertops, a farmhouse sink, breakfast bar, stainless steel appliances, and plenty of storage and workspace. From there, the layout flows into the dining room with its original corner hutch, followed by a tiled sunroom that leads out to the patio. The living room features hardwood flooring, built-in bookcases, and a wood-burning fireplace. A convenient half bathroom completes the main level. Upstairs, you'll find a primary bedroom with a walk-in closet, two additional bedrooms, and a tastefully renovated full bathroom. Approximately 430 square feet of finished space in the lower level includes a family room with a bar, workshop, laundry room with a utility sink, and additional storage. The property also includes a detached two-car garage and paved driveway.

147 Old Mill Rd, Middletown

$449,900

3 Beds ⋅ 2 Baths ⋅ 24199578 MLS

Welcome to 147 Ridge Rd, a stunning, completely remodeled home located in the highly desirable South Farms district of Middletown! This beautifully updated property has been renovated from top to bottom and is truly move-in ready. The heart of the home is the spectacular open-concept kitchen, featuring beautiful quartz countertops and seamless flow into a bright, light-filled living room with a decorative stone fireplace. Throughout the home, you'll find beautifully refinished hardwood floors and two beautifully updated bathrooms, each featuring elegant inlaid tile showers. The dining room features a slider to an impressive 16-foot deck, creating the perfect setting for indoor and outdoor entertaining, relaxing, and enjoying the private surroundings. Major updates include a new roof and windows, a newer furnace, and new electrical wiring and electrical panel. Every detail has been thoughtfully updated to create a comfortable, stylish, and modern home. This is a must-see property! Schedule your private showing today and experience everything 147 Ridge Rd has to offer.

147 Ridge Rd, Middletown

$429,000

3 Beds ⋅ 2 Baths ⋅ 24196637 MLS

Welcome to 76 George St, Middletown! This 1,600 SF home offers 3 bedrooms, a spacious kitchen, and plenty of potential to make the property your own. The walk-out lower level features roughed-in plumbing, creating an exciting opportunity for additional living space, a recreation area, or a possible in-law apartment. Set on nearly one acre of land, the property offers additional road frontage on Boston Rd and the potential for an additional structure, subject to zoning and approvals. With generous land, flexible space, and multiple possibilities for future use, this property offers an excellent opportunity for homeowners, investors, or those looking to create additional living space. A lease-to-own option is also available. Don't miss this unique opportunity-bring your vision and explore the possibilities!

76 George St, Middletown

$415,000

4 Beds ⋅ 2 Baths ⋅ 24197069 MLS

Welcome to 104 Bell Street - a rare find on 2.6 private acres in the heart of Middletown. This 4-bedroom, 2 full bath home offers a truly unique setting where you drive down a long, secluded driveway and cross a bridge over Sawmill Brook to arrive at your own private oasis. Fully updated throughout, this home features a renovated kitchen, updated bathrooms, new flooring, new 200-amp electrical service, new AC unit and furnace, new oil tank, an updated well system, and a resurfaced bridge. The wooded, incredibly private lot offers endless potential - whether you envision expanded outdoor living, gardens, or simply the peace and quiet of your own retreat tucked away from the world. Despite the secluded feel, the property is easy to show and conveniently located with quick access to I-91, Wesleyan University, and downtown Middletown. With so much already done, this is a move-in ready home with room to dream on 2.6 acres. Buyer to verify flood zone designation and obtain flood insurance quotes prior to purchase. Agent/Owner.

104 Bell St, Middletown

$495,000

3 Beds ⋅ 2 Baths ⋅ 24194620 MLS

Turnkey and beautifully maintained, this inviting home is nestled in a well-kept Middletown subdivision. The open-concept main level features a bright kitchen with granite countertops, a dining area and a comfortable living room - all flowing seamlessly together. Step outside the French doors to a fenced in spacious patio surrounded by low-maintenance turf, creating a peaceful retreat with no grass to mow. A private pool offers the perfect place to cool off on hot summer days or unwind during quiet evenings. The main level also includes a family room, a full bathroom, and a flexible home office that can serve as a fourth bedroom. Upstairs, you will find the primary bedroom, two additional bedrooms, and a second full bathroom with granite finishes. Hardwood floors run throughout the home, complemented by tile in the kitchen and bathrooms. The home's mechanical systems have been carefully maintained and include a top-of-the-line Buderus system also a new installed Heat Flow water heater. Enjoy easy access to Middletown's vibrant downtown dining scene, as well as Routes 9 and 91 for easy commute travel to Hartford and New Haven.

17 Coles Rd, Middletown

$450,000

24028033 MLS

Are you seeking boundless opportunities? Whether it's a serene retreat, a haven for animals, a solar venture, or a hunting plot, this property is a canvas for your dreams. Nestled upon Chestnut Mountain, this property is located in the South Fire District of Middletown. Breath-taking views and stunning sunsets are just a bonus! This property offers a two-stall barn with a tack room that stands ready to accommodate equestrian pursuits. Additionally, there are two elevated hunting blinds and a rudimentary 100 yard rifle range. Roughed in roadways and dirt bike trails make navigating this property a breeze. The potential here is limitless...come experience it for yourself!

East Mount Road, 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

$499,900

3 Beds ⋅ 2 Baths ⋅ 24159101 MLS

This 1,500 sq ft ranch-style home, built by Silvin Homes, offers thoughtfully designed one-level living with an open-concept layout ideal for everyday living and entertaining. The spacious living area flows seamlessly into the kitchen with a center island and ample cabinetry, creating a welcoming gathering space. The private primary suite features a custom full bath and walk-in closet and is set apart for added privacy, while two additional generously sized bedrooms and a second full bath provide flexibility for guests or home office needs. A dedicated laundry area and convenient entryway from the attached one-car garage enhance everyday functionality. Nathan Hale Estates is a thoughtfully planned residential community in Middletown, Connecticut, offering a quiet neighborhood setting while remaining conveniently close to shopping, dining, schools, parks, and major commuter routes. The central location provides easy access to the shoreline, making this an ideal place for you and your family. The builder offers generous allowances, allowing buyers to thoughtfully curate finishes and selections. Builder requires a one-time construction-to-permanent loan, financed by Elm Tree Funding.

Lot 4 Nathan Hale, Middletown

$479,900

2 Baths ⋅ 24053933 MLS

*** Prime Commercial Property for Sale - 110 Coe Ave, Middletown, CT *** Discover an exceptional investment opportunity with this versatile commercial property. Ideal for a wide range of business ventures, this property allows both flexibility and prime location appeal. Featuring a spacious interior, ample parking, and excellent visibility, it's perfectly suited for retail, office, or mixed-use development. Ideally positioned in Middletown with easy access to I-91 and so close to Route 9. Conveniently located near Middlesex Hospital, one of the top medical facilities in the region, providing heathcare and attracting a steady flow of traffic. In close proximity to Wesleyan University, Middlesex Community College, Xavier High School and local Middletown schools, offering potential customer base and employee convenience. Directly next to Tradewinds Shopping Center with Restaurants, Retail Shops and Car Wash. This property is perfect for retail stores, medical offices, a professional facility, or a mixed-use development. Take advantage of this rare opportunity to own a prime piece of Middletown's commercial real estate. Whether you're expanding your business or looking for a new investment, 110 Coe Ave has the perfect blend of location, flexibility, and potential.

110 Coe Ave, Middletown

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Between $400K - $500K Middletown Real Estate

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Browse All Middletown CT Between $400K - $500K Properties for Sale

Between $400K - $500K Middletown Real Estate

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