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$525,000
4 Beds 4 Baths 1813425 MLS
Welcome to The Highlands Historic District! This Stunning Brick Ranch boasts nearly 4k Sq Ft of Lovely living space.4 bedrooms,3 1/2 baths. Primary Bedroom offers a large walk-n-closet adjoining bath with 2 separate sinks, walk -n- shower, Jetted tub. Gourmet Kitchen opens up to family room. Home office, 4 Season room, Finished lower level can be a separate living quarters has a bedroom flex room, full bath,Bar area,Family room and lots and lots storage space. Off the Garage is another an area that has the space to be used as a second kitchen. This home has 2 Oversized garages The garage when pulling into the driveway is heated. Many special things about this home including close to I-75 This home is awe-inspiring!

397 Highland Street, Middletown

$335,000
4 Beds 4 Baths 1810660 MLS
The one you have been waiting for. This Historical Victorian Painted Lady was built in 1899. Features 4 plus BR's, 3-1/2 BA's and 4 fireplaces. Historical charm includes stain glass, pocket doors, French doors, a call-button in middle of dining room floor, crown molding and more. Second floor laundry, a guest suite w/partial kitchen and a bonus Sun Room. 3rd-floor walkup to spacious attic w/complete flooring for additional storage. Enclosed screened porch leads to outside deck. Restored wrought iron surrounds the front with mechanical gate entry to exterior 4-car garage. Privacy fence surrounds the back yard. While the owners have brought this home to life with a labor-of-love, there still are things that need to be done. Fall in love with the history of this Historical area and surrounding homes.

313 S Main Street, Middletown

$385,000
5 Beds 4 Baths 1807010 MLS
Welcome home to 8 Alameda Circle! This absolutely gorgeous home is situated on a picturesque lot with mature trees and so much privacy- perfect for enjoying the yard or huge back deck! Step inside and the possibilities are endless, as is the space! Not only is there a full unfinished basement with a built in garage, there is so much square footage to make this your perfect home. The character of this home is ENDLESS, from the built-ins in the beautiful dining room that overlooks the large front yard, to the sunroom where you can spend your days relaxing. Looking to work from home? This home has plenty of options for a home office! Plus a breakfast room and butler's kitchen. On top of all that, there is a great Loft space on the top floor with an additional bedroom suite. Book your showing today!

8 Alameda Circle, Middletown

$605,500
4 Beds 2 Baths 1803123 MLS
Amazing historic home on 2 acres w/guest house! Many recent updates offer modern conveniences, while maintaining historic charm! Main house has spacious rooms including formal dining, home office/living, family room, mud room off kitchen. Recent updates include new roofs, HVACs, public sewer conversion from septic in main house & guest house. Main house updates include master bath, LVP flooring throughout, updated fireplace & built-ins in great room, and more! Beautiful outdoor space with pergola patio area and pretty landscaping throughout, fenced back yard & a tree house! Guest house has 2 bedrooms, bath, full kitchen, laundry & living room! Perfect for extended family, work from home or added living space!

5218 Hendrickson Road, Middletown

$1,076,000
1800802 MLS
Beautiful, income producing 20-unit apartment complex on a quiet, residential street with an ideal location close to I75 between Cincinnati and Dayton. Property is cash flowing with all units occupied, except one left vacant for showings. Owner and property manager have spent the past year carefully screening and selecting tenants, replacing any problem tenants for the next owner. Due to the high-demand location, there is never a problem filling vacancies. There is still plenty of room to raise rents to market rent. Tenants pay their own electric and owner is reimbursed for water. Property is professionally managed by Northpoint Asset Management, who are open to staying on as the property manager for the next owner.

4534 Bonita Drive, Middletown

$250,000
5 Beds 2 Baths 1798649 MLS
All the difficult and expensive renovations are done for you. All galvanized plumbing removed and replaced. New high efficiency furnace. New electric. Box gutters done and rubber lined. Chimneys inspected and tuck pointed. All you have to do are cosmetics and make it YOU! Located in the much desired South Main Historic District. (you will love the neighbors) half bath not finished, but can be easily. 2nd floor layout makes it easy to add another bath. Huge kitchen already plumbed for pot filler over stove. 42' attic ready to finish if you need even more space. This house is over 3100 sqft., stained glass, pocket doors, porches front and rear and both 1st and 2nd floor. Short walk to Forest Hills Country Club. These sellers love this house, but it's time to Move South and let some lucky buyers be the new caretakers of this piece of history.

512 S Main Street, Middletown

$436,500
5 Beds 4 Baths 1795883 MLS
Step into the timeless charm of this meticulously preserved historic home in the sought after Highlands Historic District, a true gem built in 1928. Boasting 5 spacious bedrooms and 3.5 bathrooms, this architectural masterpiece spans an impressive 4,232 square feet. The craftsmanship of a bygone era is evident in every detail, from the ornate moldings to the original hardwood floors. A perfect blend of character and modern comfort, this home invites you to experience the elegance of yesteryear within the embrace of its warm, inviting spaces. Immerse yourself in the rich history of this residence while enjoying the convenience of modern amenities. A truly unique opportunity to own a piece of the past with the luxuries of today.

3 Alameda Circle, Middletown

$255,000
7 Beds 6 Baths 1788796 MLS
Don't miss the opportunity to own this 7-bedroom, 5.5-bath Victorian home with approximately 6,186 square feet of living space. This house features an all-brick exterior with a porch and a covered patio to sit on for tons of fresh air & sunlight, an open floor plan with hardwood flooring throughout, a living room with a fireplace, a kitchen with built-in cabinets, and a dining area. Enclosed porch to sit and relax on while enjoying the view of your backyard that is perfect for a play area, open space, or additional outdoor living! Ready for you to put your personal touches on this home! Tons of potential! Being sold as is, where is, Buyer is responsible for all required inspections & certifications (if applicable). All info & property details set forth in this listing, including all utilities & all room dimensions which are approximate, are deemed reliable but not guaranteed & should be independently verified if any person intends to engage in a transaction based upon it.

304 S Main Street, Middletown

$325,000
3 Beds 3 Baths 1788453 MLS
Welcome home to this beautiful 3 BR 3 full BA ranch condo that is move-in ready & offers one floor living. This stunning property boasts a wealth of exquisite features that are sure to capture your heart. Beautiful hardwood floors were just refinished this past summer. Spacious rooms, vaulted ceilings, skylights flood the home w/ natural light providing ample space for family & guests. Walk out to freshly stained, 2 level deck from both primary BR or Great Room to enjoy morning coffee. Unwind in your very own private hot tub & soak away the day's stresses on the lower level. 1st floor bathrooms recently updated with granite/marble counters, new toilets, cabinets. The condo has a spacious finished bsmt that incl. a game room, wet bar, cedar closet, bedroom & full bath. Home gym is included w/ the sale. One of the many remarkable perks of living in this exceptional condo is the HOA's commitment to maintaining the property & landscaping. Don't miss your chance to make this home your own.

4907 Hickory, Middletown

$290,000
4 Beds 4 Baths 1788168 MLS
This Perfect Family Home is Move in Ready and just minutes from Middletown HS/MS and Miami University campus. This modern home Boasts 4 Bdrm, 3 Full and a 1/2 Bath with 2 Fireplaces with a total of 1952 sqft of living space upstairs and approx 1000 sqft in the basement. The interior is Immaculate and has Fresh Paint and New carpet throughout! Primary bedroom is Ex-large with a walkout porch to enjoy that morning cup of coffee or evening glass of wine. The other 3 bedrooms are Spacious as well. The finished basement has a full bath and is great for entertaining. Outside you're greeted with a Beautifully landscaped lawn and the property sits at the end of a dead end street so no next door neighbors. All appliances stay. This won't last long! Make this your Perfect family home!

915 Gage Drive, Middletown

$435,000
4 Beds 4 Baths 1786225 MLS
Welcome Home as you enter original slate tiled foyer leading to a sunny living room. This house boasts 2 fireplaces and spacious living in this gorgeous updated ranch style home on nearly an acre lot. Remodeled French inspired chef's kitchen with stone countertops, white subway tile backsplash and stainless appliances opens into extra large dining room to host dinner parties large and small! Oversized windowed family room with built in book cases, brick fire place and plush carpet opens onto private covered deck and patio overlooking privacy fenced back yard with mature trees and mature landscaping. Perfect to entertain! Master bedroom is freshly painted with ample closet space. Fully updated Master bath has large shower and marble throughout. Guest bath fully updated, marble tops and flooring. Huge laundry room in large finished basement with 3 double door closets, full bath and wet bar makes the perfect rec room. Bonus shed in backyard for extra storage or a playhouse for kids!

4204 Rosedale Road, Middletown

$150,000
1786665 MLS
Update: Pending offer+Security, seller requests to hold all showings until further notice. A landmark building in an established neighborhood, 610 Gladys Drive is a well-maintained, solidly constructed brick building that was built in 1955 as a religious facility. With over 7,500 square feet, the building includes a sanctuary, recreation room, offices, four restrooms, and two kitchens. There is a large kitchen on the main level and a studio size kitchen on the lower level. The property includes three parcels/lots with ample parking and access from both Gladys Drive and the alley on the west side. This is a rare opportunity to invest in the community with a new religious organization or potentially redevelop into residential use. R-3 zoning. Deed Restrictions ("Declaration of Restrictive Covenant") apply at time of transfer and provided to Buyer. Personal property negotiable. Sold in As-Is. Buyer rely on own inspections. Broker is a Trustee of the existing religious organization.

610 Gladys Drive, Middletown

$600,000
5 Beds 4 Baths 1785290 MLS
Why Build when you can own this GORGEOUS, like-new 5 bdrm home, situated on over a acre tree-lined lot! Just 6 years young, this home is loaded with amenities! Features include: Chef's kitchen w/9.5 ft island, planning desk, 42'' cabs, SS appliances (GE Profile), gas cooktop & tile backsplash! Open concept family room w/gas fireplace! Finished LL w/full bath, exercise rm, media rm, rec rm & storage! Spacious primary w/2 large closets & deluxe owner's bath w/dual shower heads! 2nd fl laundry w/cabinets & utility sink! Oversized 3 car gar! Covered front porch and covered rear deck! Cul-de-sac St, Shed & firepit! 4 full baths, over 4000 sq ft of living space, 3 zone HVAC & smart home features! OPEN HOUSE FRIDAY, 10/6 FROM 5 PM-7 PM

5785 Spencer Terrace, Middletown

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity™ program of the Multiple Listing Service of Greater Cincinnati. Real estate listings held by brokerage firms other than our company are marked with the Broker Reciprocity™ logo (the small house as shown to the left) and detailed information about them includes the name of the listing brokers. This data is up-to-date as of . Copyright 2026, MLS of Greater Cincinnati, Inc. All rights reserved. Information deemed reliable but not guaranteed.