Middletown CT Historical Real Estate, Homes for Sale

2 Baths ⋅ 24207348 MLS

Located along the highly visible Newfield Street corridor, 609 Newfield Street is a converted mid-century ranch now used as professional office space. Originally built in 1950 as a single family home, the 1,500 sq ft building has been fully adapted for commercial use and currently houses Innovative Properties. The layout provides multiple private offices, meeting areas, and a welcoming reception space. The 1.09-acre lot offers ample off-street parking and room for exterior improvements. Its flexible design also makes the property a strong candidate for group home use. The owner is willing to complete modifications or provide a credit for required updates. Owner financing is available. Located within Middletown's NPC zone, the property supports a wide variety of professional, service, and light retail uses, including medical, dental, legal, salon, specialty retail, or care-based operations. With strong drive-by exposure on Route 3, convenient neighborhood access, and close proximity to local schools and amenities, 609 Newfield Street offers excellent visibility and adaptability for a business or organization seeking a ready-to-occupy space in one of Middletown's most active commercial corridors. AGENT OWNER

609 Newfield St, Middletown

$244,900

4 Beds ⋅ 1 Baths ⋅ 24205927 MLS

Set on a quiet dead-end street near Wesleyan University and downtown Middletown, 27 Fairview Ave is a classic 1934 Colonial with character, convenience, and potential. This estate property features 1,235 sq ft, 4 bedrooms, 1 full bath, (with room for a 2nd bath on the upper level) and walk-in attic space. MAJOR RECENT IMPROVEMENTS INCLUDE: NEW ROOF IN 2024 (stripped & reroofed=1 layer), NEW 200 AMP ELECTRICAL SERVICE IN 2025, a NEW OIL BOILER AND OIL TANK in 2025 as well as a NEW CEILING IN both the LIVING ROOM and ONE BEDROOM, all of which creates a strong starting point for a remodel. Seller believes there to be oak hardwood under the carpets. The traditional layout offers defined living spaces, a manageable footprint, and room to bring fresh ideas to the kitchen, bath, finishes, and overall design. Its central Middletown location provides easy access to nearby campus, downtown shops, restaurants, parks, and commuter routes. Best suited for an investor or contractor. This property will not qualify for FHA or VA financing. Cash, renovation loan or conventional financing only. This home to be sold strictly AS-IS. Seller will not make any repairs. Sale is subject to Probate Court approval.

27 Fairview Ave, Middletown

$549,900

3 Beds ⋅ 3 Baths ⋅ 24204996 MLS

Set well back from the road on 4.6 secluded acres, this beautifully maintained ranch combines generous one-level living with a bright, welcoming feel throughout. Large windows on all sides bring in abundant natural light and frame views of the expansive landscaping, lawn, and surrounding trees. The spacious remodeled kitchen anchors the home's everyday living, with beautifully crafted cabinetry, substantial granite countertops, a large custom center island, and generous workspace, complemented by expansive backyard views and seamless flow to the outdoor living space. The private bedroom wing includes a generous remodeled primary suite with hardwood floors, 3 spacious closets, and a modern private bath designed for the comfort, style, and functionality today's buyers expect. Just beyond the primary suite, a dedicated office with extensive built-ins offers flexible space for working from home, studying, meetings, or enjoying a hobby. The living and dining rooms flow together with warm hickory floors and custom millwork, while a thoughtfully designed mudroom/pantry just off the kitchen adds character and function with built-in cubbies and cabinetry. Outside, the broad, open lawn offers room to gather, play, garden, or enjoy the private setting. A Trex deck and paver patio extend the living space outdoors, creating an inviting place to relax or entertain. Meticulously cared for and truly move-in ready, this home feels spacious, comfortable, and private from the moment you arrive.

1446 Randolph Rd, Middletown

$221,900

1 Beds ⋅ 1 Baths ⋅ 24206820 MLS

CUTE AS A BUTTON! This move-in ready home on almost an acre of land, has several wonderful updates! New boiler 2025, new oil tank 2024, chimney was rebuilt from the roof line up in 2025, wood stove in living room 2013, roof approx 14 years old, driveway sealed in June, flooring in the kitchen/dining room/living room & bedroom 2022, light fixtures 2022, bathroom exhaust fan 2025, blinds 2025, storm door 2023, water heater 2023, dishwasher 2024, oven range 2025, washer 2026, dryer 2022 and the town put in a new water meter a few weeks ago! PUBLIC WATER & SEWER. This home is well cared for, clean and just as nice as the photos show it to be. Beautiful yard! Quiet neighborhood in a fantastic part of town near the Cromwell line!

79 Plumb Rd, Middletown

$1,395,000

21 Beds ⋅ 9 Baths ⋅ 24206879 MLS

Two-building mixed-use investment opportunity in Middletown. The offering includes 61 East Main Street with four apartments and two storefronts, plus a separate three-apartment building at 2-6 Flower Street, offering a more private off Main street setting. Six apartments are occupied, while the seventh is being updated with a new kitchen and bathroom. Upon completion and lease-up at the projected rent, the property is expected to offer an approximately 9% cap rate, that's before any income from the two vacant storefronts. Zoned MXI, the storefronts have previously operated as a clothing store, salon and convenience store in past years, offering flexible possibilities subject to zoning guidelines. Additional features include private off-street parking space, wood flooring, same ownership since 2014, units updated/repaired over ownership for housing voucher compliance/inspections, separate utilities, a yard area and visible East Main Street frontage. With a Walk Score of 74, the property is close to Downtown Middletown, restaurants, shops, services, Wesleyan University, the riverfront, public transportation and Route 9. Two buildings, one investment and multiple opportunities to increase income!!! Interior pics will be added prior to active date.

61 E Main St, Middletown

$280,000

3 Beds ⋅ 2 Baths ⋅ 24206413 MLS

Beautifully renovated and ready for its next chapter, this charming 3-bedroom, 2-bath home offers comfortable living with modern updates throughout. The main living spaces provide a warm and inviting setting, while three bedrooms upstairs offer privacy and plenty of room to spread out. The spacious primary bedroom features vaulted ceilings, adding an open and airy feel. Conveniently located near major highways, this home is an excellent choice for commuters while still being close to shopping, dining, and everyday conveniences. With thoughtful renovations already completed, there's nothing left to do but move in and enjoy!

6 Hillside Ct, Middletown

$379,900

3 Beds ⋅ 2 Baths ⋅ 24205306 MLS

Well maintained 3 bedroom home with flexible floor plan. 1 bedroom on the first floor, as well as 2 full baths, Living room, and eat-in kitchen. The second floor has 2 additional bedrooms. 1st Floor Laundry. New Furnace. Splits for air condioning. 200 amp elec. Panel w/ Generator hook up. New detached 3 car garage with loft are above.

64 Ryan St, Middletown

$379,900

3 Beds ⋅ 2 Baths ⋅ 24206199 MLS

FULLY UPDATED & TURN KEY! Welcome to 672 East Main Street, a beautifully renovated home offering extensive update inside and out. This meticulously maintained property features a new roof, siding, windows, front door, flooring, interior paint, kitchen cabinets, updated kitchen and bathrooms, and so much more. Enjoy the convenience of a dedicated washer and dryer located on the main floor, making everyday living easy and convenient without the need to go up or down. Outside, enjoy new landscaping, a new concrete walkway, and a new back patio, creating a fresh and welcoming exterior. Located close to everything, with easy access to Route 9 and just minutes from Downtown Middletown, you'll enjoy convenient access to shopping, dining, entertainment, and everyday amenities. With so many major improvements already completed, this home is truly move-in ready and turn-key. Just unpack, settle in, and enjoy!

672 E Main St, Middletown

$429,900

6 Beds ⋅ 3 Baths ⋅ 24206285 MLS

3 unit property for sale. Great investment opportunity or for owner occupant. Separate utilities. Some updates. Convenient to shopping, restaurants, highway access, recreation and entertainment.

82 Westfield St, Middletown

$380,000

3 Beds ⋅ 2 Baths ⋅ 24205840 MLS

Gorgeous move in ready Ranch completely remodeled from roof to basement. This is just what you have been searching for. A beautiful custom home with great curb appeal on a newly landscaped lot with oversized paved parking area and granite trimmed garden area. Located close to schools, shopping and major highways it is priced right for the many amenities this property has for you. Seller used only the best materials and craftsmanship for the entire house. You will love the new kitchen with white cabinetry, tiled flooring, stone counters and new designer stainless appliances. Stunning hardwood floors throughout the house gleam from the oversized windows overlooking the front and back yard letting sunlight stream in all day long. The soft grey interior color has endless possibilities for decor. New lighting, new exquisite tiled baths and a trim package only found in quality homes add to the extra list. The Primary bedroom has a bath with a tiled stall shower with pebble floor. Rarely available in this price point is a 3 bedroom ranch home with a new completed lower level for additional living space. New Baseboard hot water heating, w/two split central air systems, all new electrical, plumbing, siding, roof and windows. The lower level boasts a full basement ready for your furniture that is can be used as a recreation room or office suite. You will be amazed at the upscale style and quality that went into this home. Don't hesitate to view, this Ranch is spectacular

45 Spencer Dr, Middletown

$329,900

3 Beds ⋅ 2 Baths ⋅ 24201404 MLS ⋅ Arawana Estates BLDG.

Welcome to Arawana Estates, where historic charm meets modern comfort in a truly unique setting! Located within a beautifully converted mansion, this rarely available penthouse-style condo offers a spacious & distinctive layout filled with character & natural light. High ceilings, hardwood floors, recessed lighting, oversized windows & custom built-ins create a warm & inviting atmosphere throughout. The updated kitchen features crisp white cabinetry, leathered granite countertops with breakfast-bar seating, stainless steel appliances & a new Bosch dishwasher. Beautifully appointed baths offer granite finishes, subway tile & a relaxing soaking tub. The impressive primary bedroom is a standout, offering generous proportions, beautiful hardwood flooring, a fireplace & extensive custom built-in cabinetry & shelving. In-unit laundry & abundant storage add everyday convenience. Set within an intimate 6-unit community, Arawana Estates is surrounded by expansive lawns, mature trees, distinctive stonework & picturesque views, creating a peaceful & private setting just minutes from everything Middletown has to offer. Conveniently located near Wesleyan University, downtown Middletown, restaurants, shopping, parks, trails & public transportation. Veterans Memorial Park is also nearby, offering a community pool, splash pad & walking trails. A rare opportunity to own a one-of-a-kind residence combining historic architecture, modern updates, generous living space & beautiful surroundings.

122 Newfield St Unit 3A, Middletown

$1,000,000

24203918 MLS

PERMIT IN HAND - READY TO BUILD! Located in the heart of Middletown and within walking distance of an abundance of downtown amenities, 54 Washington Street presents an exceptional redevelopment opportunity in a highly desirable location. Formerly home to the Italian American Club, this distinctive property offers both character and history while being fully positioned for its next chapter. The property has received zoning approval for conversion from a community/event space into 18 residential units, with additional space incorporated for a superintendent. A tremendous amount of the development work has already been completed. The property includes professionally engineered 18-unit build-out plans, along with stamped electrical and plumbing plans. With major building systems professionally designed, code-compliant, and permit-ready, a new owner can move directly toward the construction phase-eliminating much of the time, cost, and uncertainty typically associated with the planning and approval process. Adding even greater value, the Town has approved 18 parking spaces directly across the street, adjacent to the police station. For the savvy investor or developer seeking a residential conversion opportunity with approvals, plans, parking, and a prime downtown location already in place, 54 Washington Street offers a rare opportunity to step into a project that is truly ready to build.

54 Washington St, Middletown

$309,900

5 Beds ⋅ 2 Baths ⋅ 24203700 MLS

**Multiple Offers, Highest and Best Due EOD Wednesday, 9/9/26** Opportunity knocks in the heart of Middletown! This two-family home sits just minutes from Route 9, public transportation, and the Main Street corridor with its restaurants, shops, and year-round events. Live in one unit and have a tenant help pay your mortgage, or add a solid two-family to the portfolio - a great fit for owner-occupants and investors alike. Unit 1 has been freshly updated with new flooring, fresh paint, an updated kitchen and bath, and ceiling fans. Unit 2 offers a functional layout with an enclosed sun porch and its own private entry. Separate utilities, including two electrical panels and two heating systems, keep operating simple. Additional highlights include enclosed porches, new flooring and updates throughout, an open unfinished basement with plenty of storage, and off-street parking for multiple vehicles. Appliances will be provided with the right offer. Close to Wesleyan University, hospitals, parks, and commuter routes to Hartford and the shoreline. Easy to show - schedule today! Agent Owner

105 Spring St, Middletown

$359,999

3 Beds ⋅ 2 Baths ⋅ 24196726 MLS

Welcome to 123 Fisher Rd, a charming 3-bedroom, 2-bath Cape offering a flexible floor plan and plenty of space to suit today's lifestyle. One of the home's standout features is the main-level bedroom, which is currently being used as an additional living space. This versatile room provides an excellent opportunity for a family room, home office, den, or comfortable first-floor bedroom depending on your needs. The main level offers a welcoming flow between the living areas, kitchen, full bathroom, and flexible bonus space. Upstairs, you'll find additional bedrooms that provide privacy and room for family or guests. With two full bathrooms and a traditional Cape layout, the home offers both functionality and flexibility. Located in a convenient Middletown setting, 123 Fisher Rd is close to everyday amenities, shopping, dining, parks, schools, and major roadways. Schedule your showing today before it's too late!

123 Fisher Rd, Middletown

$454,900

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

$399,900

6 Beds ⋅ 2 Baths ⋅ 24202328 MLS

Welcome to this character-filled, turn-of-the-century two-family Colonial in the heart of Middletown, ideally located directly across from Wesleyan University and within walking distance of downtown, restaurants, shops, and public transportation. Each spacious unit offers three bedrooms, a generous living room with a fireplace, beautiful built-in cabinetry, wood flooring, and French doors opening to a sunroom. Large, open kitchens with walk-in pantries provide ample space and functionality, while charming period details throughout reflect the home's original character. The first-floor unit is vacant and move-in ready, while the second-floor unit is currently tenant-occupied, offering immediate rental income. A new roof adds significant value, while the interiors still provide opportunities for updates and personal touches. Situated on a corner lot with two separate driveways accessed from different streets, plus a convenient walkout basement. An excellent opportunity for an owner-occupant or investor!

108 High St, Middletown

$110,000

3 Beds ⋅ 1 Baths ⋅ 24202339 MLS

Bring Your Vision to Life! This 3-bedroom single-family home offers approximately 1,300 square feet of living space and is situated on a quiet dead-end street. Featuring a cozy backyard and a layout with plenty of potential, this property is an excellent opportunity for buyers looking to renovate and create a home tailored to their style. With some updating and TLC, this home has the potential to truly shine. A great opportunity for a homeowner, investor, or renovator looking to add value and make it their own. Sold AS-IS

17 Miller St, Middletown

$374,500

6 Beds ⋅ 2 Baths ⋅ 24202551 MLS

Welcome to this beautifully remodeled two-family home ideally located within walking distance of vibrant downtown Middletown! This property offers the perfect blend of modern updates, spacious living, and unbeatable convenience. Both units have been fully remodeled with new appliances and updates throughout, making this an excellent opportunity for an owner-occupant, investor, or multi-generational living arrangement. Enjoy the added charm and versatility of enclosed back porches, perfect for relaxing, extra storage. A standout feature is the walk-up attic, offering approximately 650 additional square feet of living space-an incredible opportunity to create additional bedrooms, an office, recreation room, or whatever best suits your needs. Natural gas heat and hot water, separate utilities. Common laundry area in the basement with brand new washer and dryer. Step outside and enjoy everything Middletown has to offer, with parks, restaurants, shops, and downtown attractions all just a short walk away. Located in the heart of a lively and growing community, this home combines convenience, character, and future potential. Move-in ready, fully updated, and in a fantastic location-this is a two-family opportunity you won't want to miss!

74 Grove St, Middletown

$349,900

3 Beds ⋅ 2 Baths ⋅ 24201520 MLS

Located in desirable South Farms, this charming 3 bed, 1.5 bath Cape offers a comfortable and versatile floor plan with the convenience of a 1st floor primary bedroom. Warm hardwood flooring and abundant natural light create an inviting atmosphere throughout the main living areas, while the 1st floor layout provides the ease of one-level living where it matters most. The spacious primary bedroom boasts a large walk-in closet and is conveniently located just off the living area next to the recently renovated full bathroom with tub and modern shower tile. The recently renovated kitchen features modern, soft-close cabinets, stainless steel appliances, timeless subway tile backsplash, granite composite sink and an abundance of cabinet and counter space. Step outside the slider from the dining room to enjoy the rear deck overlooking the fenced-in backyard, offering a great space for relaxing, grilling, or outdoor entertaining. A mudroom with laundry brings the house, garage and backyard access conveniently together. The upper level offers 2 spacious bedrooms and a large half bath. An oversized garage provides additional storage with a workbench and room to work as well. Additional features include a newer roof, new hot water heater, newer vinyl fence, a driveway that fits 4 cars, lots of storage space in the basement and located just minutes from thriving downtown, Middlesex hospital, Wesleyan and convenient access to the highway yet tucked away in an established neighborhood.

34 Overlook Ave, Middletown

$349,000

5 Beds ⋅ 2 Baths ⋅ 24201926 MLS

Welcome to this spacious 1952 Middletown Colonial, where classic charm meets low-maintenance living in a quiet neighborhood. Step inside a welcoming foyer with an entry closet that opens into a sun-drenched living area highlighted by a large bay window. The home features stunning hardwood floors throughout, flowing into a functional kitchen complete with natural wood cabinets, Corian countertops, a matching backsplash, and durable laminate flooring. Designed for effortless lifestyle flexibility, the main level hosts two bedrooms, including the primary bedroom, alongside a full bathroom with a tub/shower. Upstairs, you will find three additional bedrooms, perfect for a home office or private gym, and a second full bathroom with a tub/shower. The expansive basement is perfect for a hobbyist equipped with a dedicated tool workbench, storage shelving, and a laundry area with a washer and dryer. Outside, the home has low-maintenance vinyl siding and a cleared, level rear yard with mature landscaping and a handy tool shed. This prime location keeps you tranquil at home while placing you just minutes from Wesleyan University, downtown restaurants, nightlife, and scenic walks at Harborpark or Wadsworth Falls State Park. Commuting is a breeze with instant access to Route 9 and Route 66. This turn-key five-bedroom gem blends comfort, space, and ultimate Connecticut convenience.

130 Spencer Dr, Middletown

$369,900

3 Beds ⋅ 2 Baths ⋅ 24200173 MLS

Welcome to 46 Middlefield Street in Middletown! This beautifully remodeled home offers three bedrooms, two full bathrooms, and stylish updates throughout. The brand-new kitchen features sleek quartz countertops and modern finishes, creating an inviting space for cooking and entertaining. The refreshed interior combines contemporary style with comfortable, functional living spaces, making this home truly move-in ready. Conveniently located near shopping, dining, schools, and major routes, this property is an excellent opportunity for today's buyer. Schedule your private showing and see all this updated home has to offer!

46 Middlefield St, Middletown

$339,900

3 Beds ⋅ 1 Baths ⋅ 24200402 MLS

Welcome to 100 Jacobs Terrace, an adorable, move-in-ready, one-floor home, tucked away at the end of a quiet dead-end street with a convenient turnaround. Offering easy single-level living, this home features three bedrooms and one full bath with a comfortable and practical layout. Step outside to the fully fenced yard, where a nice deck and pergola create the perfect setting for morning coffee, outdoor dining, entertaining, or simply relaxing. While the home does not have a basement, there is a shed and attic space to provide additional storage. Ideally located in a peaceful residential setting while still close to all that Middletown has to offer, this home is convenient to shopping, dining, parks, schools, downtown Middletown, Wesleyan University, and major highways. Whether you're a first-time buyer, downsizing, or simply looking for the ease of one-floor living, 100 Jacobs Terrace is a wonderful place to call home.

100 Jacobs Ter, Middletown

$375,000

6 Beds ⋅ 2 Baths ⋅ 24200794 MLS

WELCOME TO THIS BEAUTIFULLY REFRESHED PROPERTY OFFERING CLASSIC CHARM, COMFORTABLE LIVING SPACES, AND EXCELLENT OUTDOOR APPEAL. THE INVITING EXTERIOR FEATURES A GENEROUS TWO-STORY COVERED PORCH, PROVIDING THE PERFECT SPOT TO ENJOY YOUR MORNING COFFEE, RELAX, OR ENTERTAIN GUESTS. THE ATTRACTIVE GRAY SIDING, CRISP WHITE TRIM, LANDSCAPED BEDS, AND WELL-MAINTAINED LAWN CREATE WONDERFUL CURB APPEAL. INSIDE, YOU WILL FIND FRESHLY PAINTED INTERIORS, ATTRACTIVE WOOD-LOOK FLOORING, AND AND ABUNDANCE OF NATURAL LIGHT THROUGHOUT. THE EAT IN KITCHEN FEATURES WHITE CABINETRY, OVEN/RANGE WITH MICROWAVE AND REFRIGERATOR. THE SPACIOUS LIVING AREAS OFFER FLEXIBILITY FOR COMFORTABLE EVERYDAY LIVING, DINING, A HOME OFFICE, OR ADDITIONAL SLEEPING SPACE. THE PROPERTY ALSO OFFERS MULTIPLE ENTRANCES AND GENEROUS COVERED OUTDOOR SPACE, ADDING BOTH CONVENIENCE AND VERSATILITY. A GREAT OPPORTUNITY FOR AN OWNER OCCUPANT OR INVESTOR. CONVENIENTLY LOCATED CLOSE TO LOCAL AMENITIES, SHOPPING, DINING, AND TRANSPORTATION, THIS PROPERTY IS READY FOR ITS NEXT CHAPTER.

108 Maple St, Middletown

$310,000

3 Beds ⋅ 1 Baths ⋅ 24199523 MLS

Welcome to 286 Russell Street, a warm and cozy cottage-style home bursting with curb appeal and gorgeous architectural details. A welcoming, adorable front porch invites you inside to discover a main level showcasing hardwood floors and lovely trim work throughout. The inviting living space centers around a detailed fireplace, creating the perfect environment for crisp evenings, while a lovely sunroom offers a bright, serene retreat to relax and unwind. At the heart of the home is a beautifully renovated kitchen (2018), boasting high-quality finishings and a highly functional layout. The main floor features two bedrooms and a bathroom, while the spacious attic, currently functioning as an office and family room, is a fully recognized third bedroom, complete with its own closet and distinct character. Modern efficiency seamlessly blends with classic craftsmanship. The entire home was fully insulated with premium spray foam in 2026, keeping utility bills low and temperatures stable all year long. Additional high-value upgrades include a brand-new washer and dryer set installed in 2026. Situated in a prime Middletown location, this move-in-ready gem sits just a short distance from the Pat Kidney Sports Complex, offering access to a premier multi-use athletic facility. It is easy to walk or drive to downtown in a little over one and a half miles. Schedule your tour today!

286 Russell St, Middletown

$364,900

5 Beds ⋅ 3 Baths ⋅ 24199686 MLS

This well maintained colonial, located just steps from the bustling downtown of Middletown, is ready for its new owner! Three units, all on different floors, offer flexible plans for owner-occupants and investors alike! The first and second floor units are comfortably controlled with high efficiency Navien units, both with a 2 bed/1 bath layout. The third unit is also natural gas, and provides a generous sized 1 bed/1 bath unit. The units themselves are mostly updated, some with fresh paint and tile work tastefully done. A two car garage and off street parking provide ultimate convenience for owners and/or tenants. Lively flower beds decorate the front walkway, adding to the curb appeal. A back staircase seconds as small deck platforms overlooking the backyard. Whether living in one unit and renting the others for residual income, or adding this wonderful opportunity to your investment portfolio, this one is NOT to miss. Schedule your private showing today!

53 Spring St, Middletown

$400,000

3 Beds ⋅ 2 Baths ⋅ 24192947 MLS

Tastefully updated and move-in ready, this charming 3-bedroom, 2-bath home is located in Middletown's desirable South Farms area. The spacious family room features a vaulted ceiling and brand-new skylights, creating a bright and welcoming gathering space. The updated kitchen offers abundant cabinet storage, granite countertops, stainless steel appliances, and a center island. The dining room showcases hardwood flooring, a wood-burning fireplace, and access to a four-season sunroom complete with a custom-built bar, perfect for entertaining year-round. The first floor includes a bedroom with hardwood floors, a full bath, and an additional flex room ideal for a home office, playroom, or hobby space. Upstairs you'll find two additional bedrooms and a second full bath with a stand-up shower. Relax outdoors on the back deck under the gazebo overlooking the yard. Additional highlights include a one-car under-house garage, additional room in basement perfect for workout room or storage, brand-new roof with 50 year transferable warranty, and numerous updates throughout. Conveniently located within walking distance to schools and just minutes from Main Street Middletown, shopping, dining, and major highways.

25 Garfield Ave, 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

$585,000

4 Beds ⋅ 3 Baths ⋅ 24198723 MLS

Welcome Home! 85 Oakcliff is a beautifully updated 4-bedroom, 2.5 bath home in a desirable Middletown neighborhood, privately set back from the road. Featuring an updated kitchen, new windows throughout, remodeled baths and a finished walk-out basement with a full bathroom this home offers space, flexibility and privacy. The finished lower level provides potential for an in-law apartment or separate living space, subject to town approval, making it ideal for extended family, guests, a home office or recreation. The expansive deck overlooks a beautiful yard for entertaining, a game of catch or running with your favorite four legged pal. Close to major highways, 20 minutes from Downtown Hartford, 35 minutes to New Haven, 45 minutes to CT Casinos, a little over an hour to the Rhode Island line and minutes from Wesleyan University, great shopping and restaurants in downtown Middletown! Major updates include: Brand New Septic- 2019 Kitchen remodeled - 2024 All windows replaced - 2024 Basement remodeled - 2023 Garage doors replaced - 2023 Full bathroom remodeled - 2022 AC air handler & condenser - 2021 Electrical upgrades & generator hookup - 2021 Well pump - 2021 Front door - 2021 Paver walkway & gutter/fascia improvements - 2020 Chimney repair & cap - approx. 2019 Boiler -2014 With a private setting, extensive updates, 4 bedrooms, 2.5 baths and a versatile walk-out lower level, this Middletown Colonial is ready to welcome its next owner!

85 Oakcliff Rd, Middletown

$317,000

2 Beds ⋅ 2 Baths ⋅ 24194383 MLS

Move right in to this well-maintained raised ranch offering comfortable living and a functional floor plan. Enter through the street-level foyer, where you'll find access to the attached garage, a full bathroom, laundry area, utility room, and a versatile room that is perfect for a home office, den, workout room, or man cave. The main level features a bright eat-in kitchen, a spacious living room, and two bedrooms. Step outside from the kitchen onto the Brand-new deck. An ideal spot for morning coffee or entertaining family and friends. A standing room attic primed for remodeling provides storage and offers excellent potential to be finished for additional living space, subject to local approvals. The low-maintenance yard is perfect for those seeking easy upkeep while still enjoying outdoor space. Situated on a quiet street, this home is conveniently located near a park, schools, shopping, restaurants, and major commuter routes. Don't miss this wonderful opportunity to own this 1776 square feet America's house. Has a lot of possibilities for a growing family.

70 Bielefield Rd, Middletown

$245,000

3 Beds ⋅ 2 Baths ⋅ 24199236 MLS

Cute 3-bedroom Cape with loads of potential! The spacious living room features a cozy fireplace and sliders leading to a private backyard-perfect for relaxing or entertaining. An open kitchen flows into the dining room, creating a comfortable layout for everyday living. Conveniently located near major roads while tucked away in a quiet neighborhood. The home needs some TLC, but the possibilities are endless to make it your own and add your personal touches!

46 Meech Rd, Middletown

$289,900

3 Beds ⋅ 2 Baths ⋅ 24199099 MLS

Welcome to 177 Front Street, a charming farmhouse-style home in Middletown's desirable Farm Hill District. This 3-bedroom, 1.5-bath home offers a functional layout with comfortable living space, a formal dining room, and plenty of natural light throughout. Recent updates include fresh interior paint, newer Stainless Steel appliances and countertops, and freshly painted wood cabinetry, giving the kitchen a clean, refreshed feel while maintaining the home's original character. Outside, enjoy the cedar front porch, a great spot to relax year-round, along with a rear deck overlooking the level backyard. This lovely home is located just minutes from downtown Middletown, shopping, restaurants, major highways, and everyday conveniences. A move-in-ready home with farmhouse charm, thoughtful updates, and a location that makes getting around easy.

177 Front St, Middletown

$369,900

4 Beds ⋅ 1 Baths ⋅ 24198560 MLS

Back on Market, and meant to be for You!! This adorable Cape boasts 4 bedrooms, an Open Layout, Fully Finished Basement, and an Enchanting private, flat fenced yard with a pool, Magnificent Weeping Willow tree, Firepit, and Gazebo. The Main level welcomes a friendly open layout connecting the open kitchen to the living room with cozy wood burning fireplace, Primary bedroom, Full bathroom, and another bedroom which can be used as an office if a 4th is not needed, as well as a laundry area quietly tucked away. Enter the Breezeway with dramatic wood vaulted ceiling, and french doors looking out to the patio and pool, which is currently being used as a Romantic Dining Room. Upstairs you will find two ample sized bedrooms. The Fully Finished basement offers more room for an In-Law possibility complete with kitchen and full bath. The oversized Tandem garage will hold 3 compact cars, or two large trucks and motorcycles, or hobbies. The roof is 5 years old, and the solar panels are owned and convey with the home at no additional cost to save you money on your electric bill. Located in a convenient location for commuting close to 91, route 9, close to shopping, restaurants, golf courses and more. Must Come see!!

171 Smith St, 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

$450,000

2 Beds ⋅ 2 Baths ⋅ 24196263 MLS

Welcome to 1511 Country Club Rd, a charming 2-bedroom Cape with the posability of 5- bedrooms offering comfort, character, and exceptional versatility. This inviting home features a flexible layout with a private in-law suite or separate living space-perfect for multi-generational living, guests, a private home office or income possibility. Step outside to enjoy the expansive backyard, offering plenty of room for entertaining, gardening, or relaxing. A fenced-in area provides a safe and secure space for people or pets to play, while the rest of the large yard offers endless opportunities to enjoy the outdoors. Whether you're looking for your first home, room to grow, or a property with flexible living options, this charming Cape is a wonderful place to make your next home.

1511 Country Club Rd, Middletown

$699,000

4 Beds ⋅ 3 Baths ⋅ 24197740 MLS

Nestled in the sought-after Chimney Hill neighborhood, this spacious Colonial offers over 4,200 square feet of thoughtfully designed living space on a beautifully landscaped lot. The home features 4 bedrooms, 2.5 bathrooms, a bright, open floor plan, generous living and dining areas, and a spacious kitchen perfect for everyday living and entertaining. The family room provides a warm gathering space, while the primary suite offers a private retreat with ample closet space and an en-suite bath. Additional highlights include a two-car attached garage, a large backyard ideal for outdoor entertaining, and a prime location just minutes from downtown Middletown, Wesleyan University, shopping, dining, parks, and major commuter routes. This is a rare opportunity to own a beautiful home in one of Middletown's most desirable neighborhoods.

20 Chimney Hill Rd, Middletown

$299,900

2 Beds ⋅ 3 Baths ⋅ 24197288 MLS

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 cozy wood stove. Most of the interior has been freshly painted, giving the home a fresh, welcoming feel throughout. The home offers two full bathrooms, plus a convenient half bath located just off the primary suite and with easy access to the pool-perfect for guests while entertaining. The expansive basement offers endless possibilities for a home gym, office, media room, or additional living space. Complete with energy-efficient solar panels, this home truly has something for everyone!

824 Randolph Rd, Middletown

$289,900

2 Beds ⋅ 1 Baths ⋅ 24197062 MLS

Welcome home to this well-maintained ranch in Middletown! The spacious living room and dining area feature beautiful hardwood floors, creating a warm and inviting space for everyday living and entertaining. The kitchen offers newer stainless steel appliances and durable laminate flooring. In addition to two generously sized bedrooms, you'll find a versatile bonus room that's perfect for a home office, craft room, or flex space to fit your needs. Major updates include a new boiler and hot water heater installed in 2020, along with solar panels added in 2023 for increased energy efficiency. Step outside to enjoy the large, level backyard-ideal for gardening, play, entertaining, or simply relaxing. Conveniently located close to shopping, dining, parks, and major highways, this move-in-ready home is one you won't want to miss!

115 Markham St, Middletown

$425,000

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

$379,900

4 Beds ⋅ 2 Baths ⋅ 24196455 MLS

Welcome home to this charming Cape Cod-style house, offering 1,874 square feet of comfortable living space, plus an additional 150 square feet of finished space in the basement. This inviting four-bedroom, 2 full bath home is nestled in a wonderful neighborhood, combining timeless charm with everyday comfort. The updated kitchen is ready for cooking, gathering, and entertaining, while the spacious living room features a cozy fireplace-perfect for relaxing evenings at home. A one-car garage and an outdoor storage shed provide added convenience and plenty of room for tools, lawn equipment, or seasonal storage. Step outside to a spacious deck overlooking the backyard, creating a wonderful setting for morning coffee, outdoor dining, or simply enjoying the peaceful surroundings. The property also includes an above-ground pool that offers great potential and just needs a little TLC to be enjoyed again. The upper bathroom present an excellent opportunity to update and personalize the home to your own style, allowing you to add value while making the space uniquely yours. With its generous layout, desirable location, updated kitchen, classic Cape Cod character, and inviting outdoor living space, this home is ready to welcomes its next owners. VERY MOTIVATED SELLERS!

25 Morgan St, Middletown

$394,500

3 Beds ⋅ 2 Baths ⋅ 24195917 MLS

Welcome to 45 Annette Place! This beautifully maintained home is truly move-in ready and has so much to offer. The updated kitchen features granite countertops, stainless steel appliances, and recessed lighting, creating a bright and modern space. Hardwood floors flow throughout the living room and bedrooms, adding warmth and timeless appeal. The partially finished basement provides additional living space and is complete with a cozy pellet stove-perfect for relaxing year-round. Need room for vehicles, hobbies, or storage? The impressive 3-car garage offers endless possibilities. Outside, you'll be welcomed by beautifully landscaped grounds that add exceptional curb appeal and create a wonderful outdoor setting to enjoy. This is a home you'll be proud to own!

45 Annette Pl, Middletown

$385,000

3 Beds ⋅ 2 Baths ⋅ 24193289 MLS

Welcome home to this beautifully remodeled 3 bedroom, 2 full bath home that's truly move in ready! Enjoy relaxing on the inviting front porch or entertaining in the fenced backyard. The updated kitchen features stainless steel appliances, plenty of cabinet and counter space, and room for meal preparation. The spacious living room offers a cozy fireplace and new flooring, creating a warm and inviting atmosphere. The finished lower level provides additional living space with two finished rooms, a full tiled bathroom, and a laundry area with washer and dryer. Perfect for a family room, home office, gym, playroom, or guest space. Recent updates include central air, windows, flooring, fenced backyard, along with many additional improvements. This home is conveniently located near shopping, restaurants and parks and offers the perfect combination of comfort, style, and convenience. Don't miss your opportunity to make this beautiful home yours!

49 George St, Middletown

$410,000

3 Beds ⋅ 1 Baths ⋅ 24195038 MLS

Welcome to this charming 3-bedroom, 1-bath ranch nestled on the highly sought-after Higby Road. Set on a generous half-acre lot, this home offers the perfect opportunity for first-time buyers, downsizers, or anyone looking to add their personal touch. Inside, you'll find comfortable one-level living with a functional layout, hardwood floors, and a cozy fireplace. Additional features include an attached garage, partially finished basement for extra living or storage space, and a peaceful backyard with plenty of room to relax or entertain. Conveniently located near shopping, dining, parks, and major commuter routes, this home combines a desirable location with endless potential. Don't miss your chance to make this Higby Road gem your own!

104 Higby Rd, Middletown

$395,000

3 Beds ⋅ 3 Baths ⋅ 24194117 MLS

Welcome home to this charming property located at the end of a peaceful cul-de-sac. This residence features three bedrooms, including a primary bedroom with an ensuite full bathroom. There are two updated full bathrooms in total, along with a convenient half bath. As you enter, you'll notice the gleaming hardwood floors that flow throughout the main living areas. The kitchen is thoughtfully designed with granite countertops, maple wood cabinets, and stainless steel appliances, offering a great setup for everyday cooking. The dining area seamlessly connects to the cozy living space, which features a gas fireplace and a mini-split system, providing an additional heating and cooling option for year-round comfort. From the dining area, sliding doors open to a patio with Trex decking, complete with a retractable awning, perfect for providing shade when needed and easily rolled back for sunny days. The two-car garage provides direct access to a finished basement area that includes a half bathroom and laundry facilities, enhancing the home's functionality. Energy-efficient solar panels ensure excellent coverage, leading to no current electric bill. Step outside to discover a private walking path accessible right from your backyard. This home is fully move-in ready, waiting for you to create lasting memories.

3 Yellow Pine Cir, Middletown

$269,000

3 Beds ⋅ 2 Baths ⋅ 24191998 MLS

Investors are you looking for a charming 2/3 bedroom, 1.5 bath Colonial that is located on a quiet street in a desirable neighborhood, offering convenient location just minutes from the shops, restaurants, Wesleyan University, hospitals, and major healthcare centers? This is an excellent choice for anyone seeking an easy commute and access to everyday amenities. Filled with warmth and character, this inviting home is ready for its next chapter. Whether you're a first-time homebuyer, looking to make it your forever home, or searching for a great investment opportunity, this property offers endless potential. Add your personal touch and some love to make this charming Colonial truly your own while creating lasting memories for years to come. City water and city sewer. Don't miss the opportunity to own a home in a convenient and quiet location. Schedule your showing today and discover all that 153 Eastern Drive has to offer!

153 Eastern Dr, Middletown

$349,900

4 Beds ⋅ 2 Baths ⋅ 24189620 MLS

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 with steel beam and loft area. Solar panels...SELLER WILL CREDIT $15,000 TOWARDS BALANCE OF SOLAR PANEL CONTRACT.

125 Stevens Ln, 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

$1,000,000

24189275 MLS

Exceptional commercial opportunity in one of Middletown's busiest retail corridors. Situated on approximately 0.47 acres, this 5,115 SF commercial building offers outstanding visibility with average daily traffic counts of approximately 20,000 vehicles. Currently operating as an auto repair facility with five vehicle lifts, the property is well-suited for continued automotive use or redevelopment. Located in the desirable B-2 General Commercial Zone, this site offers tremendous flexibility for a variety of commercial uses, making it an excellent investment or development opportunity. Surrounded by established national and local businesses, the property benefits from strong exposure, convenient access to major roadways, and a thriving commercial environment. Whether you're looking to expand your existing business, invest in an income-producing property, or redevelop a prime commercial site, this is a rare opportunity to secure a highly visible location in one of Middletown's most sought-after business districts.

516 Washington St Unit 1, 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

$390,000

7 Beds ⋅ 2 Baths ⋅ 24188106 MLS

Owner occupied or investors! 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 mechanical improvements throughout. The property has been thoughtfully upgraded while maintaining its charm and functionality. Ideal for investors seeking a turnkey asset with reliable tenants and minimal deferred maintenance. Conveniently located near shopping, restaurants, schools, public transportation, and major highways. Don't miss this opportunity to add a fully occupied, income-producing property to your portfolio. Being SOLD AS-IS.

194 Liberty St, Middletown

$90,000

5 Beds ⋅ 3 Baths ⋅ 24182301 MLS

Opportunity awaits at this 2-family residential property in a convenient Middletown location. The existing structure has sustained fire damage and is being offered strictly as-is. Ideal for investors, contractors, or buyers seeking a renovation or redevelopment project. Situated on a level lot with access to public water and public sewer. Close to shopping, dining, parks, and commuter routes. A unique chance to restore, reimagine, or rebuild subject to municipal approvals.

18 Portland St, Middletown

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