Middletown, CT Homes for Sale

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  /38

  $449,900

  • 3 Beds
  • 2 Baths
  • 1,537 Sq Ft

  95 Training Hill Rd, Middletown, CT 06457

  The single-family home at 95 Training Hill Road in Middletown, Connecticut, is a charming ranch-style residence featuring four bedrooms and two bathrooms. The interior boasts an open floor plan with flowing rooms. The kitchen is equipped with newer appliances and updated cabinets. Additional highlights include a full basement, a newer air conditioning unit, and a newer roof, ensuring the home is

  

  Guillermo Araujo

  Five Stars Realty

  (860) 743-0759

  95 Training Hill Rd, Middletown, CT 06457
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  /38

  $429,999

  • 4 Beds
  • 2 Baths
  • 1,980 Sq Ft

  106 Lorraine Terrace, Middletown, CT 06457

  COMPLETELY RENOVATED WOODLAND OASIS IN SOUGHT-AFTER WESTFIELD! This stunning split-level home sits on a private 0.47-acre lot blending modern luxury with natural charm. Freshly painted inside and out with new architectural roof and high-efficiency central AC. The showstopping kitchen features white-shaker cabinetry, granite countertops, stainless appliances, and herringbone blue tile backsplash.

  Romanee Ives Cornerstone Homes Plus, Inc.

  106 Lorraine Terrace, Middletown, CT 06457
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  /40

  $399,000

  • 3 Beds
  • 2.5 Baths
  • 2,292 Sq Ft

  10 Bidwell Terrace, Middletown, CT 06457

  Enjoy the perks of new construction-without the wait. Built in 2023, this 3-bedroom, 2.5-bath home offers the perfect blend of modern design and everyday functionality. With 2,000 square feet of living space, the open-concept main floor features a bright living area and a beautifully appointed kitchen with quartz countertops, stainless steel appliances, and plenty of cabinetry. High ceilings and

  Heidi Matusik Lamacchia Realty

  10 Bidwell Terrace, Middletown, CT 06457
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  /31

  $435,000

  • 4 Beds
  • 3.5 Baths
  • 2,708 Sq Ft

  92 Goodman Dr, Middletown, CT 06457

  Great opportunity for sweat equity! Last sale in this neighborhood was mid 500's in 2023. Some work started: Roof is 4 years old, a few new windows, chimney recapped, some flooring replaced, but needs someone to make it shine again. Central air not working, deck needs repair & lots of cosmetic work to be completed. 4 bedrooms 2 1/2 baths in main house plus 3 Room in-law apartment in walk-out

  Eileen England eXp Realty

  92 Goodman Dr, Middletown, CT 06457
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  /39

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,695 Sq Ft

  5 Westmont Dr, Middletown, CT 06457

  Conveniently located close to Wesleyan University and just minutes from downtown Middletown, this beautifully updated home offers a perfect blend of comfort and potential. The main level features a spacious primary bedroom with a full bath, providing ease and accessibility. Upstairs, you'll find two additional bedrooms with gleaming hardwood floors. The eat-in kitchen has new SS appliances,

  Natuzza Dimasi William Raveis Real Estate

  5 Westmont Dr, Middletown, CT 06457
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  /40

  $580,000

  • 4 Beds
  • 3.5 Baths
  • 3,756 Sq Ft

  36 Mcgrath Dr, Middletown, CT 06457

  Welcome to your dream home! This spacious Colonial offers the perfect blend of comfort, style, and convenience. Inside, you'll find a thoughtfully designed layout ideal for both entertaining and everyday living. The main floor features a bright, eat-in kitchen, a formal dining room for special occasions, a cozy living room, a welcoming family room, and a private office - all complemented by a

  Tom Derick Executive Real Estate Inc.

  36 Mcgrath Dr, Middletown, CT 06457
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  /29

  $397,000

  • 2 Beds
  • 1.5 Baths
  • 1,024 Sq Ft

  20 Mulberry Ln, Middletown, CT 06457

  Charming Colonial in a Desirable Neighborhood Don't miss this amazing opportunity to own a charming colonial in a highly sought-after neighborhood! Nestled in a peaceful cul-de-sac, this cozy, well-maintained home offers a space efficient floor plan and is part of a planned unit development (PUD). This home also includes a weather protected entrance on an inviting front porch. The first floor

  Noreen Sinclair Berkshire Hathaway NE Prop.

  20 Mulberry Ln, Middletown, CT 06457
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  /28

  $437,500

  • 4 Beds
  • 2 Baths
  • 2,036 Sq Ft

  515 Hunting Hill Ave, Middletown, CT 06457

  Welcome to 515 Hunting Hill Avenue, a charming Cape Cod-style home in the heart of Middletown. This beautifully updated 4-bedroom, 2-bathroom home offers 2,036 sq.ft. of living space with a bright, inviting layout. The living room features a wood-burning fireplace, creating a warm and inviting atmosphere, while the renovated kitchen boasts white shaker cabinetry, quartz countertops,

  Jasmine Smith The Agency

  515 Hunting Hill Ave, Middletown, CT 06457
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  /38

  $549,900

  • 4 Beds
  • 2.5 Baths
  • 2,340 Sq Ft

  613 Ridgewood Rd, Middletown, CT 06457

  Exceptionally maintained 4 bedroom, 2.5 bath Colonial home built in 1996 is located on a secluded 1.5 acre lot, nestled away in the Westfield neighborhood of Middletown. This property offers maximum privacy, surrounded by beautiful trees and hardly visible from the road. Upon entering the home, you immediately appreciate the open concept, hardwood flooring, wainscoting and abundance of natural

  Gregory Clancy eXp Realty

  613 Ridgewood Rd, Middletown, CT 06457
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  /40

  $589,999 Open Sat 12PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 2,813 Sq Ft

  16 Snow Ridge S, Middletown, CT 06457

  Nestled near the top of highly desirable Westfield Hills on a private cul-de-sac, this bright, oversized Colonial offers space, comfort, and charm. With 4 bedrooms-including a spacious master suite with a walk-in closet, large office, and private bath with jacuzzi tub and shower-this home is built for relaxed living. A second full bath completes the upper level. Downstairs, the open layout is

  Bruce Bayles William Raveis Real Estate

  16 Snow Ridge S, Middletown, CT 06457
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  /20

  $475,000

  • 4 Beds
  • 1 Bath
  • 1,075 Sq Ft

  35 Boston Rd, Middletown, CT 06457

  Welcome to 35 Boston Ave, Middletown, a classic 4-bedroom Cape Cod-style home with great potential! This home offers a functional layout with two bedrooms on the first floor and two additional bedrooms upstairs, making it ideal for a variety of living arrangements. Featuring hardwood floors throughout, an eat-in kitchen, and a full unfinished basement, this home is ready for your personal touch.

  Michael Calabro Coldwell Banker Calabro

  35 Boston Rd, Middletown, CT 06457
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  /11

  $589,900 Open Sat 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft

  145 Webster Ln Unit 2-41, Middletown, CT 06457

  Discover Carefree Living at Founders' Ridge - the Award-Winning 55+ Adult Community! Come experience the "KIRBY II," available for occupancy in early 2026! Located in the highly sought-after Westfield section of Middletown, this beautiful 1,555 sq. ft. home has the convenience of single-floor living with top-of-the-line features and Elegant Design: Enjoy the sophistication of white cabinetry with

  Phyllis Bysiewicz Berkshire Hathaway NE Prop.

  145 Webster Ln Unit 2-41, Middletown, CT 06457
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  /3

  $449,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  00 Villa St, Middletown, CT 06457

  DON"T SETTLE on Your Home: Take this opportunity to get the House of your Dreams... This lot has a picturesque view with over 100 feet of secluded River views (No Flood Ins. Needed) on a cul-de-sac with 120 ft. of road frontage. This lot already has an ideal home option with 3bd, 2 bath, open concept custom Kitchen (quartz countertops, Island, Tile floor), Dining room with sliders to deck area,

  Lisa Sherman My Realtor, LLC

  00 Villa St, Middletown, CT 06457
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  /35

  $419,900

  • 3 Beds
  • 1.5 Baths
  • 1,884 Sq Ft

  6 Coles Rd, Cromwell, CT 06416

  Welcome to 6 Coles Road, Cromwell! This 3-bedroom, 1.5-bath ranch-style home with an under-house garage offers comfort, space, and convenience-all in one. Zoned HB, the property also offers potential for a home business, adding versatility to its already functional layout. The open-concept design features an eat-in kitchen with stainless steel appliances that flows seamlessly into the dining

  Giulia Terese Hagel & Assoc. Real Estate

  6 Coles Rd, Cromwell, CT 06416
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  /31

  $289,900

  • 4 Beds
  • 2 Baths
  • 1,601 Sq Ft

  65 Stevens Ln, Middletown, CT 06457

  Run do not walk to see this amazing story book home. Extremely versatile offering 2 bedrooms on the first floor with a full bath and 2 bedrooms upstairs with additional full bath. This picturesque Cape sits a beautiful level landscaped lot offering magnificent center patio with pergola draped with mature grape vines. Perfect for all your outdoor entertaining and Barbecue's. The interior of this

  Mark Toledo Berkshire Hathaway NE Prop.

  65 Stevens Ln, Middletown, CT 06457
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  /21

  $379,000 Open Sat 12PM - 1PM

  • 6 Beds
  • 3 Baths
  • 2,480 Sq Ft

  35 Clinton Ave, Middletown, CT 06457

  **OPPORTUNITY**Sidewalk lined neighborhood with this well cared for 3 family home resting at the end of the street! Fully fenced, large, covered patio in the backyard, plenty of paved off street parking, detached 3 car garage & more! Lower level is unfinished, great for storage & laundry! All units feature 2 bedrooms, 1 full bath, kitchen & living room! 1st floor with a covered porch & 2nd floor

  Eugene Kirouac Premier Re Group LLC

  35 Clinton Ave, Middletown, CT 06457
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  /12

  $127,500

  • 1 Bed
  • 1 Bath
  • 579 Sq Ft

  117 Burgundy Hill Ln Unit 117, Middletown, CT 06457

  Want to be the first to live in this total rebuilt condominium?? This building at Peppermill Village was where there was a fire in February of 2024 that destroyed many units. Insurance and Association rebuilt building and now ready for occupancy. Unit offers 1 bedroom that is carpeted, has laminate in Livingroom and kitchen, New everything. Owner putting stainless steel appliances in the next

  Kerry Hart William Raveis Real Estate

  117 Burgundy Hill Ln Unit 117, Middletown, CT 06457
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  /12

  $449,900

  • 5 Beds
  • 2 Baths
  • 2,262 Sq Ft

  23 Silver St, Middletown, CT 06457

  Take advantage of this chance to own a versatile multi-unit property that combines space, flexibility, and strong investment potential. Whether you're planning to live in one unit and rent out the other or fully lease the entire property, this is an excellent opportunity to build long-term equity. Each unit features generous living areas and spacious bedrooms-perfect for attracting reliable

  Yvonne Bailey I'Lann Realty, LLC

  23 Silver St, Middletown, CT 06457
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  /36

  $350,000

  • 4 Beds
  • 1.5 Baths
  • 2,042 Sq Ft

  191 Long Hill Rd, Middletown, CT 06457

  Step into timeless charm with this delightful 4-bedroom home, one and a half baths, and 2,042 square feet of living space. Set on a level 0.46-acre lot surrounded by beautiful countryside, this circa-1860 gem is full of character and ready for your personal touch. Enjoy peaceful views and outdoor strolls with a lovely walking path just across the street. The location is convenient to all your

  Carol Farmer William Raveis Real Estate

  191 Long Hill Rd, Middletown, CT 06457
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  /22

  $169,999

  • 1 Bed
  • 1 Bath
  • 670 Sq Ft

  282 Carriage Crossing Ln Unit 282, Middletown, CT 06457

  Welcome to the highly desirable Carriage Crossing community!! This bright and sunny 3rd floor, one-bedroom unit features a cozy fireplace, vaulted ceiling, recently installed 4/2022 HVAC heating/air system & hot water heater. Washer & Dryer included in the unit. Enjoy the condo's fantastic amenities, including a pool, gym, hot tub, sauna and racquetball court. Conveniently located near I-91,

  PATRICIA SHERWIN Dave Jones Realty, LLC

  282 Carriage Crossing Ln Unit 282, Middletown, CT 06457
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  /34

  $350,000

  • 5 Beds
  • 2 Baths
  • 2,275 Sq Ft

  8 Batt St, Middletown, CT 06457

  Discover 8 Batt St, Middletown, CT-a stunning 5-bed, 2-bath ranch blending single-level ease with modern updates. Nestled in a quiet, family-friendly area, this move-in-ready home offers comfort and style. Step into a bright foyer leading to a spacious living room with hardwood floors and large windows. The updated kitchen boasts stainless steel appliances, quartz counters, a breakfast nook, and

  Luke Florian SSG Real Estate LLC

  8 Batt St, Middletown, CT 06457
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  /14

  $374,900

  • 7 Beds
  • 4 Baths
  • 2,236 Sq Ft

  68 High St, Middletown, CT 06457

  Two family home rented until March 2026! Immediate investment opportunity! Large 2-unit home located within a few minutes of Wesleyan University and downtown Middletown! Tenants pay for their own heat and hot water too! Well maintained home that you'll be proud to add to your investment portfolio!

  Dawn Satagaj William Raveis Real Estate

  68 High St, Middletown, CT 06457
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  /13

  $399,900

  • 11 Beds
  • 4 Baths
  • 5,039 Sq Ft

  84 High St, Middletown, CT 06457

  Captivating original woodwork throughout this home! Dining room with built-ins, great wood floors and room after room! There are 10 bedrooms in unit #1! Currently used as a rental property, this home could continue as a solid investment, but, would make a spectacular home for someone looking to bring this beauty back to glory! This location is ideal for anyone! Walk to downtown Middletown and

  Dawn Satagaj William Raveis Real Estate

  84 High St, Middletown, CT 06457
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  /39

  $365,000

  • 3 Beds
  • 2 Baths
  • 1,581 Sq Ft

  176 Highmeadow Ln, Middletown, CT 06457

  Enjoy everyday living and unforgettable moments in this move-in-ready home located in the sought-after South Farms neighborhood of Middletown. This home features 3 bedrooms, 2 full bathrooms, 2 car garage, partially finished basement and an energy-efficient solar panel system, helping to reduce utility costs. Step inside to a bright and welcoming main level, freshly painted and featuring brand

  Kara Pedersen Carl Guild & Associates

  176 Highmeadow Ln, Middletown, CT 06457
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  /28

  $249,900

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  120 Saybrook Rd, Middletown, CT 06457

  Welcome to 120 Saybrook Road in Middletown-a delightful 2-bedroom, 1-bath home offering 1,008 square feet of comfortable living space. Perfectly situated for easy access to shopping, dining, major highways, and more, this home is ideal for anyone seeking a blend of charm and convenience. Step inside to find a warm, inviting layout with plenty of natural light and cozy living areas. The kitchen

  Sean Doran William Raveis Real Estate

  120 Saybrook Rd, Middletown, CT 06457
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  /9

  $255,000

  • 4 Beds
  • 2 Baths
  • 2,054 Sq Ft

  15 Wall St, Middletown, CT 06457

  Step into this generously sized Colonial, offering four spacious bedrooms and a flexible floor plan. The inviting living room flows seamlessly into a formal dining room-perfect for entertaining. Enjoy cooking in the large eat-in kitchen, complete with sliders that lead out to a private deck, ideal for outdoor dining and relaxation. Upstairs, you'll find four well-proportioned bedrooms, providing

  Lisa Sader-Goede Aspen Realty Group

  15 Wall St, Middletown, CT 06457
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  /13

  $360,000

  • 6 Beds
  • 3 Baths
  • 2,622 Sq Ft

  23 Portland St, Middletown, CT 06457

  This is a fantastic, possible owner-occupied investment opportunity! This spacious 3 family house with back yard is available now, in heart of downtown Middletown. The 2nd and 3rd floors are already rented, providing immediate income. The 2nd-floor kitchen has been recently renovated with updated counters and cabinets. Each unit has separate electrical panels, boilers, and water heaters, all of

  Sacha Armstrong William Pitt Sotheby's Int'l

  23 Portland St, Middletown, CT 06457
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  /20

  $299,999

  • 4 Beds
  • 1.5 Baths
  • 1,415 Sq Ft

  10 Silver St, Middletown, CT 06457

  Welcome to 10 Silver Street in Middletown! This charming colonial featuring a newer roof, brand new gas boiler, newer windows, wood floors, has been freshly painted and is move-in ready. The main floor boasts an oversized kitchen, a bright living room, a half bath, and a versatile flex space that can be used as an office, additional bedroom, or family room. Upstairs, you'll find three generously

  Sacha Armstrong William Pitt Sotheby's Int'l

  10 Silver St, Middletown, CT 06457
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  /23

  $194,900

  • 2 Beds
  • 1 Bath
  • 791 Sq Ft

  21 Portland St, Middletown, CT 06457

  Packed with character and smart updates, this charming 2-bedroom, 1-bath Colonial offers a fantastic opportunity for first-time buyers, investors, or anyone seeking a manageable and affordable home in a central location. Built in 1900 and offering 871 square feet of well-used space, this home proves that good things really do come in small packages. Inside, you'll find a comfortable and

  Amy Rio Executive Real Estate Inc.

  21 Portland St, Middletown, CT 06457
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  /34

  $368,000

  • 4 Beds
  • 1.5 Baths
  • 1,778 Sq Ft

  27 Catherine St, Middletown, CT 06457

  Multiple Offers are in, DEADLINE FOR B&H is 04/27 @8 PM - Welcome to 27 Catherine Street, a lovingly preserved 1924 Colonial nestled in Middletown's North End. Catherine Street is beloved by many, offering the best of both worlds. Just a short walk to downtown and tucked away on a quiet CT cul-de-sac. From the moment you arrive, you're welcomed by the home's front porch with classic tapered

  Sacha Armstrong William Pitt Sotheby's Int'l

  27 Catherine St, Middletown, CT 06457
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  /36

  $355,000

  • 2 Beds
  • 1 Bath
  • 1,240 Sq Ft

  25 Sunnyslope Dr, Middletown, CT 06457

  This charming 2-bedroom ranch is a comfortable and convenient one-level living experience. Featuring hardwood floors throughout, the home has warmth and character overlooking peaceful farmlands and a view of the rolling hills of Middletown. The large kitchen comes equipped with a breakfast nook and plenty of cabinet space. It has an additional room off the backside, which can be used for an

  Lisa Burns Executive Real Estate Inc.

  25 Sunnyslope Dr, Middletown, CT 06457
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  /38

  $420,000

  • 4 Beds
  • 2 Baths
  • 2,214 Sq Ft

  156 S Main St, Middletown, CT 06457

  Pull into the long private driveway-room for 6-8 cars-and you'll feel the instant charm of this beautifully renovated brick two-family. The inviting front porches and classic brick facade are paired with new vinyl siding and dual-pane windows, blending timeless curb appeal with smart energy efficiency. Behind the home, a flat level lot offers a peaceful green space and a two-car garage just

  Alan Stewart Jr. ASJ Realty Partners

  156 S Main St, Middletown, CT 06457
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  /15

  $299,900

  • 2 Beds
  • 2 Baths
  • 1,204 Sq Ft

  80 Prospect St, Middletown, CT 06457

  Discover a fantastic opportunity at 80 Prospect Street! This beautifully remodeled 2-family home in the heart of Middletown boasts newer mechanicals and brand-new appliances in both units, perfect for comfortable living or rental income. The 3-car garage is great for storage or the car enthusiast, and yet the home still has ample off-street parking. The second floor unit has a partially finished

  Paul Magliochetti Coldwell Banker Realty

  80 Prospect St, Middletown, CT 06457
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  /39

  $305,000

  • 3 Beds
  • 1.5 Baths
  • 1,944 Sq Ft

  4 Glynn Ave, Middletown, CT 06457

  Welcome to 4 Glynn Avenue! Nestled on a quiet cul-de-sac in the heart of Middletown, this beautiful Colonial offers the perfect blend of timeless charm and modern convenience. Featuring three spacious bedrooms and one-and-a-half bathrooms, the home has been thoughtfully renovated. Recent improvements include new windows, a new water heater, updated plumbing and electrical systems, remodeled

  Sofija Gjonbalaj William Raveis Real Estate

  4 Glynn Ave, Middletown, CT 06457
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  /7

  $230,000

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  52 Rising Trail Dr, Middletown, CT 06457

  Spacious townhouse in the charming and cozy Beacon Hills condo community. Conveniently located minutes from major highways, public transportation, shopping centers, restaurants, medical facilities, downtown Middletown, and the Wesleyan University campus. The property offered "As Is". Subject to short sale approval. Short Sale Rider & As Is Riders must be included with the Purchase Offer.

  Thomas Galvin Precision Realty LLC

  52 Rising Trail Dr, Middletown, CT 06457
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  /24

  $299,000

  • 6 Beds
  • 3.5 Baths
  • 3,110 Sq Ft

  71 E Main St, Middletown, CT 06457

  This four unit brick building sits on a corner lot within very close proximity to downtown Middletown. A vacant commercial space on the ground level provides a potential owner operator with tremendous opportunity. Three residential units fill the upper two floors including a one bedroom, two bedroom, and three bedroom apartment. The commercial space was once operated as a bar/restaurant and

  Connor Wenchell VC Property Group, LLC

  71 E Main St, Middletown, CT 06457
• 

  

  /18

  $210,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  3 Linden St, Middletown, CT 06457

  A single family home close to town with spacious bedrooms and living space. Plenty of storage and parking. Close to all forms of transportation, schools and shopping. Come check it out today!!

  Thomas Mele Dorrance Realty

  3 Linden St, Middletown, CT 06457
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  /33

  $300,000

  • 5 Beds
  • 2 Baths
  • 2,112 Sq Ft

  50 Liberty St, Middletown, CT 06457

  Turnkey Two-Family Investment Opportunity in the Heart of Middletown Welcome to 50 Liberty Street, a fully updated 2-family property offering both historic charm and modern efficiency-perfect for investors looking to expand their portfolio with minimal upfront work. Located just blocks from downtown Middletown, this property provides strong rental potential in a high-demand area. Each spacious

  Jonathan Zuromski Real Broker CT, LLC

  50 Liberty St, Middletown, CT 06457
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  /40

  $719,900 Open Sat 12:30PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 4,382 Sq Ft

  34 Watch Hill Dr, Middletown, CT 06457

  Set high on Watch Hill, this stunning 3-4 bedroom, 2.5-bath Colonial offers breathtaking views and over 4,382 SqFt of living space on a 1.04-acre lot. The main level features gorgeous hardwood floors, a formal dining room, and a spacious living room with a cozy wood-burning fireplace. The chef's kitchen is a dream, with granite countertops, stainless steel appliances, a wall oven, a glass

  Joe Cafasso eXp Realty

  34 Watch Hill Dr, Middletown, CT 06457
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  /7

  $145,000

  • Land
  • 3.58 Acres
  • $40,503 per Acre

  0 Mountain Laurel Dr, Middletown, CT 06457

  Build your dream home on this 3.5 acre approved building lot bordering open space. Last lot on a private cul-de-sac! Beautiful, wooded country setting for a home, yet only 1 mile from Rt 9 and 10 minutes to Downtown Middletown! Enter the lot down a picturesque driveway though the woods to a clearing with old stone walls and natural rock outcroppings. The open space for the cul-de-sac borders this

  Siobhan McLaughlin William Raveis Real Estate

  0 Mountain Laurel Dr, Middletown, CT 06457

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