Middletown Real Estate

Middletown is a charming neighborhood located in Mission Hills, San Diego County, California. Situated between the Pacific Ocean and the San Diego River, this area is brimming with natural beauty and outdoor activities. Residents of Middletown can enjoy a variety of local amenities, including a variety of restaurants, shops, and entertainment venues. The area is also home to a number of parks and recreational facilities, such as the Mission Hills Park, which offers a wide range of activities for families and individuals.

Middletown's real estate market is booming, with homes ranging from cozy one-bedroom condos to luxurious multi-million dollar estates. The area is one of the most desirable locations in San Diego County, and offers a variety of housing options for those looking to buy or rent. Home prices in the area range from affordable starter homes to luxurious multi-million dollar properties.

The Middletown area is well-connected, with easy access to major highways and freeways. The area is also close to a number of public transportation options, making it easy to get around without a car. The area also offers easy access to a variety of schools, shopping centers, and other amenities.

Middletown is an ideal place for anyone looking for a safe and vibrant neighborhood to call home. With its beautiful scenery, convenient location, and vibrant real estate market, Middletown is an ideal place to live, work, and play.

Newest Listings in Middletown

$1,175,000

3 Beds ⋅ 2 Baths

$1MM+ views that󠃳󠂠󠂀󠂠󠃢󠂁󠂢󠃢󠂁󠂣󠃢󠂁󠂣󠃍󠂏󠃍󠂏 come with a house! Perched high above the street (yes, there are stairs!) with bay | ocean | Point Loma | North Island | airport VIEWS where you can almost literally see if your ship/plane has come in!?! With this active day/night view, just up the street proximity to local and well-known establishments like Shakespeare Pub, El Indio and Blue Water Seafood Market & Grill, and leisure/work access to San Diego International Airport practically at your doorstep, the world is your oyster! High ceilings and large picture windows frame the views from your spacious living room. BONUS almost 400 sq. ft. permitted sunroom is not included in total living square footage shown in the listing. Price is reflective of the condition but Zoned RM-2-5 with further potential density bonus from Complete Communities eligible Tier 2 FAR up to 8.0. Renovate the existing home with additional units starting at street level? ADU's? Or possibly a grander vision of your choosing? Imagine the possibilities!

1610 Winder St, Mission Hills

$899,000

2 Beds ⋅ 2 Baths

Experience the best󠃳󠂠󠂀󠂠󠃢󠂁󠂢󠃢󠂁󠂣󠃢󠂁󠂣󠃍󠂏󠃍󠂏 of San Diego urban living in this 2 bedroom/ 2 bath single story condo in the highly coveted 92103 zip code. Situated at the crossroads of Bankers Hill and Midtown, location is key! This corner unit features new carpet in both bedrooms. The kitchen has a new stainless stove and microwave and a Subzero built-in refrigerator & beautiful Quartz Counters with a breakfast bar, Enjoy stunning views to Downtown San Diego, the Harbor, Lindbergh Field and Point Loma. Sunsets are just one more reason to love this location. You are just moments away from the lush greenery and cultural landmarks of Balboa Park, as well as the renowned dining and nightlife scenes of Little Italy and Hillcrest. Whether youre grabbing a morning coffee at a local caf or enjoying a sunset dinner with views of the bay, everything that makes San Diego iconic is within easy reach. Unit includes gated parking space with storage. Plenty of off street parking is also available. Experience the best of San Diego urban living in this 2 bedroom/ 2 bath single story condo in the highly coveted 92103 zip code. Situated at the crossroads of Bankers Hill and Midtown, location is key! This corner unit features new carpet in both bedrooms. The kitchen has a new stainless stove and microwave and a Subzero built-in refrigerator & beautiful Quartz Counters with a breakfast bar, Enjoy stunning views to Downtown San Diego, the Harbor, Lindbergh Field and Point Loma. Sunsets are just one more reason to love this location. You are just moments away from the lush greenery and cultural landmarks of Balboa Park, as well as the renowned dining and nightlife scenes of Little Italy and Hillcrest. Whether youre grabbing a morning coffee at a local caf or enjoying a sunset dinner with views of the bay, everything that makes San Diego iconic is within easy reach. Unit includes gated parking space with storage. Plenty of off street parking is also available.

2960 Union St Unit 101, Mission Hills

$1,999,999

8 Beds ⋅ 4 Baths

Rare 4-unit investment opportunity with breathtaking panoramic city, bay, and harbor views. Consistently rented with strong income potential, this property features four 2-bedroom, 1-bath units, each with its own one-car garage, plus a community laundry room. Designed for low-maintenance ownership in an unbeatable location, two units have been remodeled with modern updates, while the remaining units offer additional upside potential. Tenants enjoy spectacular views and convenient access to San Diego Airport, Downtown, Bankers Hill, Little Italy, Balboa Park, freeways, dining, shopping, and more. An exceptional opportunity for investors seeking stable cash flow, long-term growth, and a highly desirable San Diego rental location. The property's prime location may also present short-term rental opportunities (airbnb is allowed in the area). Don’t miss this rare investment offering.

3062-68 Columbia St, Mission Hills

$1,990,000

8 Beds ⋅ 4 Baths

SELLER TO ENTERTAIN ALL OFFERS !!! 2831–2837 Columbia Street offers investors a rare opportunity to acquire a four-unit apartment building in one of San Diego’s most sought-after urban neighborhoods. Perfectly positioned between Mission Hills, Bankers Hill, and Little Italy, the property delivers the ideal balance of strong in-place income, long-term appreciation, and unbeatable tenant appeal. With immediate access to Downtown San Diego, Balboa Park, the San Diego International Airport, and all major freeways, this asset combines location, lifestyle, and investment strength. The property consists of four spacious and modernized two-bedroom, one-bathroom apartments, each featuring premium in-unit amenities including its own washer/dryer and air conditioning (2 units), ensuring maximum comfort and convenience for tenants. In addition, every apartment comes with a separate oversized storage area—a highly desirable feature in this competitive rental market. Importantly, tenants are responsible for all utilities under their rental agreements, minimizing operating expenses and streamlining management for ownership. One of the most striking features of the property is its incredible, unobstructed views of Downtown San Diego and the San Diego Bay. This unique vantage point not only enhances the tenant living experience but also positions the property as a premier rental offering, creating consistently strong demand and long-term tenant retention.

2831-37 Columbia St, Mission Hills

Start Your Search

This information is deemed reliable but not guaranteed. You should rely on this information only to decide whether or not to further investigate a particular property. BEFORE MAKING ANY OTHER DECISION, YOU SHOULD PERSONALLY INVESTIGATE THE FACTS (e.g. square footage and lot size) with the assistance of an appropriate professional. You may use this information only to identify properties you may be interested in investigating further. All uses except for personal, non-commercial use in accordance with the foregoing purpose are prohibited. Redistribution or copying of this information, any photographs or video tours is strictly prohibited. This information is derived from the Internet Data Exchange (IDX) service provided by San Diego MLS®. Displayed property listings may be held by a brokerage firm other than the broker and/or agent responsible for this display. The information and any photographs and video tours and the compilation from which they are derived is protected by copyright. Compilation © 2026 San Diego MLS®,