Middletown, OH Homes

• 

  

  

  /16

  $359,900 Pending

  • 8 Beds
  • 8 Baths
  • 5,376 Sq Ft

  1030 Jackson Ln, Middletown, OH 45044

  Solid four-unit multifamily building offering four 2-bedroom, 1.5-bath units, each around 900 sq. ft. Currently fully leased, the property produces $3,440/month in gross rent. All units are separately metered, ensuring tenants cover their own utilities and keeping operating expenses low. With full occupancy and a strong rental history, this property delivers dependable cash flow and

  

  Andrew Gaydosh

  eXp Realty

  (513) 848-6818

  1030 Jackson Ln, Middletown, OH 45044
• 

  

  

  /12

  $950 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Townhouse for Rent

  2209 -2215 Highland St Unit 2211, Middletown, OH 45044

  2209 -2215 Highland St Unit 2211, Middletown, OH 45044
• 

  

  

  /25

  $190,000 Sold Oct 27, 2025

  • 1,232 Sq Ft
  • $154/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  1811 Waynebrook Dr, Middletown, OH 45044

  Welcome home to this 3-bedroom, 2-bath home in Middletown. With its distinctive stone exterior, this two-story home stands out with style and character. The living room features new tile flooring and an accent wall and opens to an eat-in kitchen with stainless steel appliances and plenty of cabinet space. The main level includes a full bath with a curbless shower and a laundry room. Upstairs,

  Vince Evans Glasshouse Realty Group

  1811 Waynebrook Dr, Middletown, OH 45044
• 

  

  

  /30

  Est $165,891 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,212 Sq Ft

  1809 Brentwood St, Middletown, OH 45044

  1809 Brentwood St, Middletown, OH 45044
• 

  

  

  /16

  $329,900 Pending

  • 8 Beds
  • 8 Baths
  • 5,376 Sq Ft

  1012 Jackson Ln, Middletown, OH 45044

  Turnkey quadplex featuring four 2-bedroom, 1.5-bath units of approximately 900 sq. ft. each. The property is fully occupied and generates a consistent $3,820/month in gross rent. Each unit is separately metered, limiting landlord utility obligations and simplifying management. With stable tenants in place and 100% occupancy, this is a reliable income-producing asset in a strong rental location.

  

  Andrew Gaydosh

  eXp Realty

  (513) 547-3385

  1012 Jackson Ln, Middletown, OH 45044
• 

  

  /36

  $229,000 Sold Oct 27, 2025

  • 1,341 Sq Ft
  • $171/SF
  • 21 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1953

  1227 Ellen Dr, Middletown, OH 45042

  Welcome to this well-maintained single-family home nestled on a quiet, tree-lined street just around the corner from Wildwood Elementary. Featuring 3 spacious bedrooms (primary has it's own bathroom) and 2 full updated baths, this home offers comfort, functionality and room to grow. Enjoy peace of mind with a brand new roof (2024) and a waterproofed basement with a lifetime guarantee-perfect for

  Margaret Brown Sibcy Cline, Inc.

  

  1227 Ellen Dr, Middletown, OH 45042
• 

  

  /23

  Est $128,602 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,278 Sq Ft

  4543 Bonita Dr Unit 167, Middletown, OH 45044

  4543 Bonita Dr Unit 167, Middletown, OH 45044
• 

  /2

  $70,000 Pending

  • 1 Bed
  • 1 Bath
  • 986 Sq Ft

  3102 Omaha St, Middletown, OH 45044

  Very cute 1 bedroom home on large lot, with cute porch! Excellent yard!

  

  Reva Owens

  Coldwell Banker Heritage

  (513) 506-2266

  

  3102 Omaha St, Middletown, OH 45044
• 

  

  /42

  $235,000 Sold Oct 27, 2025

  • 1,288 Sq Ft
  • $182/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  3814 Lewis St, Middletown, OH 45044

  Updated ranch home with 3 bedrooms, 2 full baths, first floor laundry and a nice fenced backyard with covered patio. Hardwood floors throughout and gas fireplace. The garage is an oversized one car with room for a motorcycle or workshop. Updates include paint, bathroom, flooring, kitchen cabinet refacing, kitchen flooring, exterior paint and more. Full basement and shed add plenty of space and

  Stefan Wannemacher Coldwell Banker Heritage

  

  3814 Lewis St, Middletown, OH 45044
• 

  

  /16

  Est $104,816 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 948 Sq Ft

  4534 Shawnray Dr Unit 93, Middletown, OH 45044

  4534 Shawnray Dr Unit 93, Middletown, OH 45044
• 

  /2

  $140,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  1700 Johns Rd, Middletown, OH 45044

  House Sold As-Is

  

  Reva Owens

  Coldwell Banker Heritage

  (513) 715-5327

  

  1700 Johns Rd, Middletown, OH 45044
• 

  

  /107

  $470,000 Sold Oct 27, 2025

  • 2,915 Sq Ft
  • $161/SF
  • 16 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1977

  4501 Pennswood Dr, Middletown, OH 45042

  Stately All-Brick Colonial with 4 Bedrooms & 5 Full BathsThis stunning Colonial, with a curved driveway and ample parking, combines timeless curb appeal with modern updates. Over the past four years, this home has been thoughtfully transformed--inside and out--and must be seen to be fully appreciated. Featuring 4 spacious bedrooms, each with its own private full bath, the home is designed for

  Rick McMaken Key Realty

  

  4501 Pennswood Dr, Middletown, OH 45042
• 

  

  /26

  Est $121,970 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,174 Sq Ft

  4530 Shawnray Dr Unit 78, Middletown, OH 45044

  4530 Shawnray Dr Unit 78, Middletown, OH 45044
• 

  

  /37

  $379,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,966 Sq Ft

  4964 Timberline Dr Unit 81, Middletown, OH 45042

  Must see this elegant custom built condominium with open and spacious first floor living. Vaulted ceilings, hardwood floors, and traditional high quality woodwork and other design features throughout. High end kitchen with maple cabinets, granite countertops, large pantry, a passthrough serving bar, and nearby laundry. Lovely and expansive first floor bedroom with a substantial walk in closet,

  Antonio Pena Berkshire Hathaway HomeService

  

  4964 Timberline Dr Unit 81, Middletown, OH 45042
• 

  

  /49

  $315,000 Sold Oct 27, 2025

  • 2,120 Sq Ft
  • $149/SF
  • 76 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1973

  1810 N Marshall Rd, Middletown, OH 45042

  Middletown! Beautiful and well maintained 4 BR, 2.5 Bath home in Manchester Manor. This home has a living room, dining room, eat in kitchen and a family room with a fireplace. Main suite has adjoining full bath. Finished basement has wet bar, perfect for entertaining or a spare bedroom. There is plenty of storage on the other side of the finished area. Covered patio and breezeway out back leads

  Rodney Muterspaw Berkshire Hathaway HomeService

  

  1810 N Marshall Rd, Middletown, OH 45042
• 

  

  /28

  Est $124,325 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,174 Sq Ft

  4520 Shawnray Dr Unit 29, Middletown, OH 45044

  4520 Shawnray Dr Unit 29, Middletown, OH 45044
• 

  

  /54

  $340,000 Pending

  • 3 Beds
  • 2 Baths

  6777 Crystal Harbour Dr, Middletown, OH 45042

  Better than new and beautifully upgraded, this 3-year-young ranch offers turn-key, maintenance-free living with thoughtful finishes throughoutand no waiting on landscaping, blinds, or grass! Featuring 3 bedrooms, an open-concept layout, and an unfinished walkout basement, this home has room to grow. The seller selected premium upgrades including a covered porch with low-maintenance Trex decking

  Denise Gifford Keller Williams Advisors

  

  6777 Crystal Harbour Dr, Middletown, OH 45042
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  /36

  $256,000 Sold Oct 24, 2025

  • 1,872 Sq Ft
  • $137/SF
  • 3 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1919

  2306 Linden Ave, Middletown, OH 45044

  Welcome home! Step inside and you'll be taken back in time to an era of true craftsmanship, with details reminiscent of a charming New England home. Situated on a desirable corner lot with a white fence and garden, the home is filled with character, architectural details, and built-ins. Inside you will find the beautiful picture framed hardwood floors along with a cozy wood-burning fireplace

  Spencer Ferrell Keller Williams Advisors

  

  2306 Linden Ave, Middletown, OH 45044
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  /29

  Est $126,239 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,174 Sq Ft

  4520 Shawnray Dr Unit 28, Middletown, OH 45044

  4520 Shawnray Dr Unit 28, Middletown, OH 45044
• 

  

  /63

  $488,750 Under Contract

  • 4 Beds
  • 4.5 Baths
  • 3,814 Sq Ft

  2727 Cleopatra Dr, Middletown, OH 45005

  Looking to be closer to Shaker Run, but not finding what you’re looking for? Tucked in a prime location with quick access to Lebanon, Springboro, Mason, and I-75, this Fischer-built Charles floor plan delivers both style and practicality. With 3,814 finished sq ft, the home balances open gathering spaces with private retreats across three floors. Featuring 4 bedrooms, 4.5 baths, and thoughtful

  Jeffrey Probst Keller Williams Community Part

  2727 Cleopatra Dr, Middletown, OH 45005
• 

  

  /34

  $275,000 Sold Oct 24, 2025

  • 2,038 Sq Ft
  • $135/SF
  • 5 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1942

  416 Glen Ln, Middletown, OH 45042

  Home for the holidays!! Lovely 3 bedroom, 1.5 bath with front porch, 2 car garage & partially fenced yard. Two bedrooms have new carpet. Kitchen has granite countertops & stainless steel appliances. Wood flooring in living & dining area with built-ins. Easy walk to Sunset Park. Comfortable family room in basement.

  Karen Mogul Sibcy Cline Inc.

  

  416 Glen Ln, Middletown, OH 45042
• 

  

  /41

  Est $219,934 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft

  4416 Creekview Dr, Middletown, OH 45044

  

  4416 Creekview Dr, Middletown, OH 45044
• 

  

  /35

  $315,900

  • 3 Beds
  • 1 Bath
  • 1,494 Sq Ft

  6261 Todhunter Rd, Middletown, OH 45044

  Completely Updated Ranch in Monroe Schools! This move-in ready home has been thoughtfully renovated from top to bottom. Step inside to find a remodeled kitchen (2021), new carpet and LVP flooring (2021), and fresh interior paint throughout. Major updates include a new roof (2022) and new hot water heater (2022). The spacious living areas flow seamlessly into a large, level, fenced backyard,

  Scot Avery Huff Realty

  

  6261 Todhunter Rd, Middletown, OH 45044
• 

  

  /22

  $160,000 Sold Oct 24, 2025

  • 768 Sq Ft
  • $208/SF
  • 33 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1951

  2303 Roosevelt Blvd, Middletown, OH 45044

  Charming and move-in ready, this 2-bedroom, 1-bath ranch offers fresh updates throughout. Enjoy brand-new flooring, new appliances, and updated cabinets that bring a modern touch to the kitchen. The convenient layout includes a cozy living space and a detached garage, all set in a great location close to amenities. Schedule your showing today!

  Jackson Brosier NavX Realty, LLC

  

  2303 Roosevelt Blvd, Middletown, OH 45044
• 

  

  /89

  Est $402,598 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,686 Sq Ft

  8 Alameda Cir, Middletown, OH 45044

  8 Alameda Cir, Middletown, OH 45044
• 

  

  /86

  $374,900

  • 3 Beds
  • 2 Baths
  • 4,418 Sq Ft

  2206 Cincinnati Dayton Rd, Middletown, OH 45044

  Commercial Property - Complete set up for mechanics garage! Endless possibilities await! Whether you're running a home business or seeking rental income, this versatile 3-bedrm, 2-bath home has it all. Charming porch is perfect for morning coffee, while the spacious living rm is filled w/ natural light. Family rm features a wood-burning fireplace for reliable heat. Kitchen offers ample space w/an

  Tami Holmes Tami Holmes Realty

  

  2206 Cincinnati Dayton Rd, Middletown, OH 45044
• 

  

  /27

  $174,900 Sold Oct 24, 2025

  • 965 Sq Ft
  • $181/SF
  • 45 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1977

  1702 Glenwood Ave, Middletown, OH 45044

  Welcome to this charming ranch home with beautiful updates throughout. As you walk in, you're greeted by a large living room with a warm fireplace and plenty of natural light. You'll find the kitchen just off the living room, complete with stainless steel appliances and a quartz countertop. The bathroom has been fully updated with tiled surround tub and shower. New LVP and LED lighting fixtures

  Eric Mielke Outside The Box Real Estate

  1702 Glenwood Ave, Middletown, OH 45044
• 

  

  /51

  Est $240,703 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,562 Sq Ft

  605 S Main St, Middletown, OH 45044

  

  605 S Main St, Middletown, OH 45044
• 

  

  /39

  $634,000 New Construction

  • 4 - 7 Beds
  • 3.5 - 8 Baths
  • 3,282+ Sq Ft

  BENNETT Plan at Hughes Retreat, Middletown, OH 45044

  The Bennett by Drees presents an open, spacious flexible two-story plan. Step inside and you'll be welcomed by an inviting foyer, which is open to a quiet home office. Beyond the main foyer is an open arrangement of the spacious kitchen with walk-in pantry, casual dining area and two-story family room. A flex room, situated in the rear of the first floor, can be used as an optional guest suite

  Drees Homes Builder

  6499 Devon Dr Unit 37255913, Middletown, OH 45044
• 

  

  /51

  $385,000 Sold Oct 24, 2025

  • 1,533 Sq Ft
  • $251/SF
  • 106 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1946

  3373 Somerville Jacksonburg Rd, Middletown, OH 45042

  Possibilities are endless at this Beautiful 5.9 Acres that nothing is built on 5.2 Acres that has a huge garage also a 30x40 Pole Barn small Pond.The house is not livable may have mold and needs lots of work Value is in the land and out buildings Please See Agent Remarks

  Jon Landrum Coldwell Banker Heritage

  3373 Somerville Jacksonburg Rd, Middletown, OH 45042
• 

  

  /30

  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  2200 Erie Ave, Middletown, OH 45042

  

  2200 Erie Ave, Middletown, OH 45042
• 

  

  /28

  $610,700 New Construction

  • 4 - 6 Beds
  • 2.5 - 7 Baths
  • 3,295+ Sq Ft

  VANDERBURGH Plan at Hughes Retreat, Middletown, OH 45044

  The open, spacious Vanderburgh offers a variety of options for you to customize to fit your family's lifestyle. Step inside and discover an elegant formal dining room just off the main foyer. Beyond the foyer, a large central living area features an open arrangement of the family room with wall of windows and optional fireplace, a kitchen with convenient island, and breakfast room - the perfect

  Drees Homes Builder

  6499 Devon Dr Unit 37255910, Middletown, OH 45044
• 

  

  /21

  $127,000 Sold Oct 24, 2025

  • 972 Sq Ft
  • $131/SF
  • 129 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1952

  1717 Pershing Ave, Middletown, OH 45044

  Adorable & Move In Ready Bungalow on Quiet Street in Middletown ! Newer Flooring & Fresh Paint Throughout ! Remodeled Kitchen with Appliances That Stay. Updated Bathroom. Spacious Family Room. Plenty of Room for a Garage or Car Port. Private Rear Yard. New Front Windows. New Stove & New Microwave. Some Buyers May Qualify for $0 Down - Inquire for More Details ! Hurry !

  Nicole Gulick Reign Realty

  1717 Pershing Ave, Middletown, OH 45044
• 

  

  /65

  Est $358,320 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,713 Sq Ft

  4946 Trenton Franklin Rd, Middletown, OH 45042

  4946 Trenton Franklin Rd, Middletown, OH 45042
• 

  

  /28

  $573,200 New Construction

  • 3 - 4 Beds
  • 2.5 - 8 Baths
  • 2,294+ Sq Ft

  SHELBURN Plan at Hughes Retreat, Middletown, OH 45044

  Drees is excited to present the Shelburn, a new home design offering convenient one-level living. From the welcoming foyer and gallery with optional tray ceilings, you'll view an impressive central living space showcasing a large family room with optional fireplace, well-equipped kitchen and open, airy dining area. You can choose to add a relaxing covered rear porch. The secluded primary suite

  Drees Homes Builder

  6499 Devon Dr Unit 37255761, Middletown, OH 45044
• 

  

  /27

  $148,455 Sold Oct 24, 2025

  • 1,208 Sq Ft
  • $123/SF
  • 99 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1950

  3110 Yale Dr, Middletown, OH 45042

  Quaint 2 bedroom home with screened in rear porch and garage. Large family room with fireplace. Hardwood flooring under carpet! Remodeled kitchen and bath in 2022. Stove and refrigerator remain. Two owner home! Agent related to Seller.

  Stefan Wannemacher Coldwell Banker Heritage

  

  3110 Yale Dr, Middletown, OH 45042
• 

  

  /44

  Est $496,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,426 Sq Ft

  3376 Renaissance Blvd, Franklin, OH 45005

  3376 Renaissance Blvd, Franklin, OH 45005
• 

  

  /37

  $599,700 New Construction

  • 3 - 4 Beds
  • 2.5 - 5 Baths
  • 2,392+ Sq Ft

  LYNDHURST Plan at Hughes Retreat, Middletown, OH 45044

  Drees' Lyndhurst plan offers comfortable one-level living in a ranch plan with plenty of options for you to make this home suit your style. Step inside and discover a quiet study just off the main foyer. The open central living area includes a large family room with optional fireplace, bright and airy dining area nook and kitchen with serving island. A covered porch off the dining area is a great

  Drees Homes Builder

  6499 Devon Dr Unit 37255746, Middletown, OH 45044
• 

  

  /19

  $161,000 Sold Oct 23, 2025

  • 1,556 Sq Ft
  • $103/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1929

  2619 Milton Rd, Middletown, OH 45042

  Location, Location, Location. Charming Home with full front porch sits across from the park! Quaint and well-loved, this home offers a first-floor primary bedroom with his-and-her closets, pocket door, and adjoining full bath. The kitchen features a built-in ironing board: a nostalgic touch! Upstairs are two additional bedrooms with hardwood floors and another full bath. Upstairs also has

  Cynthia Enderle eXp Realty

  2619 Milton Rd, Middletown, OH 45042
• 

  

  /82

  Est $496,359 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,182 Sq Ft

  3342 Renaissance Blvd, Franklin, OH 45005

  3342 Renaissance Blvd, Franklin, OH 45005

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