Middletown Real Estate

Welcome to the charming neighborhood of Middletown, nestled in the heart of Mission Hills, San Diego, CA. Middletown offers a perfect blend of urban convenience and suburban tranquility, making it an ideal place to call home.

With its tree-lined streets, historic architecture, and proximity to Balboa Park, residents of Middletown enjoy a vibrant community with a small-town feel. The neighborhood boasts a variety of local shops, restaurants, and cafes, providing plenty of options for dining and entertainment.

Nature lovers will appreciate the easy access to outdoor activities, including hiking trails, parks, and the nearby San Diego Bay. Middletown is also conveniently located near downtown San Diego, making it a great choice for those who work in the city or enjoy exploring its cultural attractions.

Whether you're looking for a cozy bungalow, a modern condo, or a historic home, Middletown offers a diverse range of real estate options to suit every taste and budget. Come discover the unique charm and convenience of Middletown – a welcoming neighborhood where community spirit thrives and city living meets suburban serenity.

Newest Listings in Middletown

$2,095,000

8 Beds ⋅ 4 Baths ⋅ 260013550 MLS ⋅ ACTIVE Status ⋅ 3062-68 Columbia St BLDG.

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

$1,199,000

3 Beds ⋅ 3 Baths ⋅ NDP2604804 MLS ⋅ ACTIVE Status

Welcome to this beautifully upgraded 3 bedroom home offering stunning bay and city views! The open-concept main living space is designed for both everyday living and entertaining, featuring a gorgeous kitchen with a large island with bar seating, generous counter space, stainless steel LG appliances, a breakfast nook, and a dining area that flows seamlessly into the entertainer's living room and out to a private brick patio the perfect spot to unwind. The spacious primary suite is a true retreat, showcasing bay and city views, a balcony, a dedicated workspace, a walk-in closet, and a spa-inspired bathroom complete with dual vanity sinks, an oversized double shower, and a skylight. Two additional well-appointed bedrooms, split-system air conditioning in the living room, primary bedroom, and second bedroom, a cozy living room with fireplace, updated flooring, multiple decks, and an attached garage with bonus storage and flexible use space round out this incredibly livable home. Ideally situated with easy freeway access and just minutes from some of San Diego's most celebrated destinations including Little Italy, Old Town, Downtown, San Diego International Airport, and so much more. And perhaps saving the best for last, just around the corner India Street puts you in the heart of Middletown's International Restaurant Row, with excellent restaurants, delis, and bars. This turnkey home is a must-see. Come experience the San Diego lifestyle! Welcome to this beautifully upgraded 3 bedroom home offering stunning bay and city views! The open-concept main living space is designed for both everyday living and entertaining, featuring a gorgeous kitchen with a large island with bar seating, generous counter space, stainless steel LG appliances, a breakfast nook, and a dining area that flows seamlessly into the entertainer's living room and out to a private brick patio the perfect spot to unwind. The spacious primary suite is a true retreat, showcasing bay and city views, a balcony, a dedicated workspace, a walk-in closet, and a spa-inspired bathroom complete with dual vanity sinks, an oversized double shower, and a skylight. Two additional well-appointed bedrooms, split-system air conditioning in the living room, primary bedroom, and second bedroom, a cozy living room with fireplace, updated flooring, multiple decks, and an attached garage with bonus storage and flexible use space round out this incredibly livable home. Ideally situated with easy freeway access and just minutes from some of San Diego's most celebrated destinations including Little Italy, Old Town, Downtown, San Diego International Airport, and so much more. And perhaps saving the best for last, just around the corner India Street puts you in the heart of Middletown's International Restaurant Row, with excellent restaurants, delis, and bars. This turnkey home is a must-see. Come experience the San Diego lifestyle!

3711 Columbia St, Mission Hills

$4,499,000

4 Beds ⋅ 4 Baths ⋅ 260011095 MLS ⋅ ACTIVE Status

Welcome to 3515 Union Street, a stunning architectural residence in the heart of Mission Hills, one of San Diego’s most coveted neighborhoods. Spanning approximately 4,600 square feet, this exceptional 4-bedroom, 3.5-bath home offers an elevated living experience defined by scale, light, and breathtaking views. Step inside to soaring 20-foot ceilings that create a dramatic first impression, complemented by expansive windows that flood the home with natural light and frame sweeping views of the city and beyond. The open-concept layout is both grand and inviting, designed for seamless entertaining and comfortable everyday living. The chef’s kitchen flows effortlessly into the main living and dining areas, while multiple indoor-outdoor transitions allow you to fully enjoy Southern California living. Spacious bedrooms provide privacy and comfort, with a luxurious primary suite that serves as a true retreat. Set on a prime street in Mission Hills, this home combines tranquility with convenience—just minutes from top dining, boutique shopping, downtown, and the airport. The neighborhood’s timeless charm, tree-lined streets, and prestigious reputation make it one of San Diego’s most desirable places to call home. With its rare size, volume, and view orientation, 3515 Union Street presents a unique opportunity to own a standout property in a premier location.

3515 Union St, Mission Hills

$1,275,000

2 Beds ⋅ 3 Baths ⋅ 260005528 MLS ⋅ ACTIVE Status ⋅ Moddom Lofts BLDG.

This striking three-level loft, where modern design meets sweeping views of the San Diego Bay and Downtown skyline. From the moment you step inside, soaring ceilings and architectural details set the tone for a home that feels both sophisticated and effortlessly livable. Custom floating stairs lead you through thoughtfully designed spaces, beginning with a versatile first-floor family room or office—ideal for working from home or creating a private retreat. With a second bedroom featuring its own walk-in closet. The main living level showcases an open-concept kitchen, dining, and living area, perfect for entertaining or simply enjoying the rhythm of city life. Large windows frame the surrounding urban landscape while maintaining a surprisingly peaceful atmosphere thanks to the home’s excellent insulation. Occupying the entire third level, the primary suite is a private sanctuary featuring a walk-in closet and a beautifully remodeled bathroom with custom stonework. Just beyond, an iron catwalk leads to one of the home’s most extraordinary features a 20' x 15' rooftop deck with breathtaking panoramic views stretching across San Diego Bay to Point Loma, the downtown skyline, and the surrounding city lights. Thoughtful upgrades elevate the experience throughout the home, including a Sonos sound system, Lutron smart lighting, Nest thermostat, and a built-in Miele espresso machine in the kitchen bringing luxury and convenience into everyday living. This home is the perfect balance of modern design, privacy, and vibrant city living—all in one of San Diego’s dynamic neighborhoods. Rooftop deck is 20x15 has stunning sweeping views. Second bedroom has walk-in closet. Home is very insulated which minimizes the urban sounds. Owner upgraded the unit with surround sound system controllable by SONOS, Lutron lighting system accessible via app/iPad, and NEST Thermostat, Somfy motorized window shades. Renovated master bathroom with custom stone work. Installed a Miele espresso maker in the kitchen. Moddom Lofts is walking distance to some of the best restaurants, coffee shops, and bars the city has to offer. Close to and walkable to Balboa Park, Little Italy, Mission Hills, and Bankers Hill with easy access to Interstate 5.

3033 India St Unit 6, Mission Hills

$1,995,000

8 Beds ⋅ 4 Baths ⋅ 2600826 MLS ⋅ ACTIVE Status

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®,