Hillside Real Estate

**Discover the Charm of Hillside, Colorado**

Nestled in the heart of Colorado Springs, Hillside is a vibrant neighborhood that perfectly blends the beauty of nature with the conveniences of urban living. Known for its welcoming community spirit and picturesque surroundings, Hillside is an ideal destination for families, young professionals, and retirees alike.

One of the most striking features of Hillside is its proximity to stunning outdoor spaces. With the majestic backdrop of the Rocky Mountains, residents enjoy easy access to hiking trails, parks, and nature reserves. The nearby Palmer Park offers miles of scenic trails, picnic areas, and breathtaking views, making it a favorite spot for outdoor enthusiasts and families looking to unwind in nature.

Hillside is also home to a diverse array of local shops, cafes, and restaurants, providing a unique blend of flavors and experiences. From cozy coffee shops to family-owned eateries, there’s something to satisfy every palate. The community hosts regular events, fostering a strong sense of camaraderie among residents and encouraging neighbors to connect.

Education is a priority in Hillside, with several highly-rated schools and educational programs available to families. The neighborhood's commitment to nurturing young minds is evident in its investment in local educational initiatives.

With its charming homes, friendly atmosphere, and access to both nature and city life, Hillside is more than just a neighborhood—it's a place where community thrives. Whether you're looking to settle down or simply explore, Hillside welcomes you with open arms. Come and experience the warmth and beauty of this hidden gem in Colorado!

Newest Listings in Hillside

$725,000

5 Beds ⋅ 3 Baths ⋅ IR1067228 MLS

Simply gorgeous! This Baseggio-built custom brick ranch combines exceptional craftsmanship, generous living space and a peaceful setting with sweeping prairie views. Oversized windows frame the landscape from the sunny breakfast nook, while the back deck and spacious patio invite you to enjoy quiet mornings watching birds, deer and other wildlife-or memorable evenings gathered around the built-in outdoor fireplace beneath wide-open skies. Inside, vaulted ceilings, beautiful oak trim, ceramic tile flooring and a cozy gas-log fireplace create a warm and inviting atmosphere. The custom Oak Tree kitchen features Corian and marble surfaces, abundant cabinetry and a charming breakfast nook, while the formal dining room provides an elegant space for entertaining. The spacious basement is already partially framed and finished, offering an excellent head start toward additional living space, a recreation room, home theater or whatever best suits the next owner's vision. An oversized, heated three-car garage provides excellent parking, storage and workspace, complemented by a generous area for RV parking. Established trees, attractive landscaping, and wrought-iron fencing complete this impressive property. A beautiful home, a remarkable setting and room to make it your own.

114 Hillside Drive, Sterling

$199,900

4 Beds ⋅ 2 Baths ⋅ 6516743 MLS

Only two owners in 113 years! Opportunities like this don’t come along often. This character-filled 1913 home sits on four combined lots and offers the charm buyers love with the opportunity to make it their own. Original ceiling beams, vintage wall sconces, and classic architectural details provide a solid foundation for restoration, while the generously sized property offers ample parking and room to grow. Perfect for investors, flippers, or buyers with a vision, this home is priced to reflect the updates it deserves. Ideally located with quick I-25 access and just minutes from downtown Pueblo, the Pueblo Mall, shopping, restaurants, and everyday conveniences, this is your chance to bring new life to a piece of Pueblo history.

2714 High Street, Pueblo

$155,000

2480123 MLS

Urban Infill Redevelopment Opportunity – Colorado Springs. Build your home in the heart of Colorado Springs! This residential lot offers an outstanding in-town location just minutes from vibrant downtown Colorado Springs, where you’ll enjoy popular dining, local breweries, shopping, entertainment, and year-round events. Nearby Memorial Park provides endless recreation opportunities with Prospect Lake, trails, sports fields, tennis courts, and open green space, all set against the stunning backdrop of Pikes Peak. Enjoy concerts, Broadway performances, and community events at Pikes Peak Center, while still having quick access west to the mountains for hiking, fishing, skiing, and weekend adventures. Rare opportunity to own a residential homesite close to urban amenities while embracing the Colorado lifestyle. All city utilities are available to make this fully functional and ready to go for a new build. The surrounding neighborhood is experiencing significant urban revitalization and rehabilitation, making this an exciting opportunity to invest in a rapidly improving area. A structure previously existed on the property and has already been demolished, potentially simplifying future development plans. Don't miss this exceptional opportunity to acquire a strategically located infill parcel in the heart of Colorado Springs. Zoned R-2, this vacant lot offers excellent potential for duplex, paired-home, ADUs, or other residential redevelopment, subject to City approval. Situated within a designated Opportunity Zone and located in Qualified Census Tract 22, the property may appeal to developers seeking projects in areas targeted for community reinvestment. These designations can provide meaningful advantages such as Low Income Housing Tax credits, depending on a buyer’s investment strategy and should be independently verified.The lot is surrounded by established neighborhoods, existing utilities, employment centers, schools, parks, and convenient access to downtown Colorado Springs, making it an ideal candidate for urban infill development. As available buildable land within the city continues to become increasingly scarce, opportunities like this are attracting builders, investors, and organizations focused on neighborhood revitalization. Whether your vision is market-rate housing or a thoughtfully designed redevelopment project, this property offers the location, zoning, and redevelopment potential to bring that vision to life. Buyers are encouraged to verify all zoning regulations, allowable uses, development standards, utility availability, Opportunity Zone status, Qualified Census Tract eligibility, and any applicable local, state, or federal incentive programs.

824 E Costilla St, Colorado Springs

$532,000

3 Beds ⋅ 2 Baths ⋅ 2834134 MLS

Discover a rare blend of charm, space, and investment upside in the vibrant heart of Downtown Colorado Springs. This fully renovated home sits on a generous double lot with coveted R2 zoning—allowing a duplex, ADU (accessory dwelling unit), or multi-family use—making it ideal for owner-occupants, house-hackers, and investors. Bright, open-concept main level with natural light, updated flooring, and fresh paint throughout. The kitchen features quartz countertops, stainless-steel appliances (gas range, dishwasher, refrigerator), shaker cabinetry, tile backsplash, and a serving buffet—designed for daily living and entertaining. Spacious living and dining areas flow seamlessly for easy gatherings. The fully finished basement has a private entrance and a complete ADU: living room, full kitchen, bedroom, and modern full bath. Perfect for long-term rental income, short-term guests (check local STR rules), multi-generational living, or home office/guest suite. Key Features & Lifestyle • Double lot with expansive yard—gardening, entertaining, or future development (subject to zoning). • R2 zoning = flexibility for duplex conversion, ADU, or additional units—rare downtown. • Prime Downtown Colorado Springs location: walk/bike to restaurants, breweries, shopping, parks, trails, CC, and the Pikes Peak Greenway. Quick access to I-25, Old Colorado City, and Memorial Park. • Updated systems, modern finishes, and move-in ready condition. Whether you’re seeking a primary residence with income potential, a turnkey house-hack, or a long-term investment, this renovated downtown home delivers lifestyle + cash flow in one of Colorado’s most desirable urban neighborhoods.

421 S Prospect St, Colorado Springs

$532,000

8848423 MLS

*Charming Fully Renovated Downtown Home with R2 Zoning and Income Potential!* Welcome to your dream home in the vibrant heart of Colorado Springs! This beautifully renovated residence, situated on a generous double lot, features highly desirable R2 zoning that creates a fantastic investment opportunity for savvy buyers. As you step inside, you'll be greeted by a bright and open layout that immediately makes you feel at home. The stunning kitchen showcases stainless steel appliances, quartz countertops, and ample cabinetry with serving buffet makes it a perfect space for entertaining. The main floor houses a spacious living area that is infused with natural light, and a convenient dining space that flows seamlessly into the kitchen. Venturing downstairs, you'll discover a fully finished basement that offers a private entrance, providing independence and privacy for guests or tenants alike. This versatile basement includes a fully equipped accessory dwelling unit (ADU) featuring its own inviting living area, a full kitchen, a cozy bedroom and bath, and a modern bathroom—making it ideal for generating rental income or providing comfortable accommodations for visiting friends and family. KEY FEATURES: *Double Lot* Enjoy an expansive outdoor area that presents endless possibilities for gardening, entertaining, or future development projects. *R2 Zoning* Take advantage of the versatile zoning that enhances the property's potential, opening doors for various residential and investment opportunities. *Prime Location* Immerse yourself in the vibrant downtown Colorado Springs lifestyle, with an array of nearby shopping, dining, cultural attractions, and beautiful parks just moments away. This property is the perfect blend of a charming home and a lucrative investment opportunity, making it a rarity in today’s market. Don’t miss out on this exceptional chance to become part of the Colorado Springs community. explore all that this remarkable property has to offer!

421 S Prospect St, Colorado Springs

$399,000

8066314 MLS

Located on a corner lot in downtown Colorado Springs' beautiful Hillside community, this shovel ready, urban infill apartment complex offers 10 luxury, Class A units, with amazing mountain views and immediate proximity to downtown amenities. Take advantage of this property's Opportunity Zone tax benefits, which means you pay zero capital gains taxes on the sale after building and owning the apartments for ten years. This project is ready for builder permits, with all drawings and site variances approved and stamped by the city and tap fees already paid. As Hillside's future anchor point for urban living, all units will feature 9' interior ceilings, 8 tuck-under covered parking spots, 8 storage units, 8 bike storage units, a dedicated dog wash, and electric vehicle charging stations. Investment opportunities like this rarely make it to the open market. Make this one yours today!

703 E Costilla St, Colorado Springs

$225,000

3 Beds ⋅ 2 Baths ⋅ 2282554 MLS

This charming 3-bedroom, 2-bathroom home is nestled in a quiet neighborhood and features a desired split-bedroom design, offering both privacy and comfort. Inside, the residence boasts hardwood floors throughout, complemented by stylish tile in the kitchen. The kitchen also includes stainless steel appliances. The main bathroom showcases attractive tiling. Outdoor living is a delight with a large wooden porch and stone patio in the private backyard, and a covered front porch with a decorative railing providing welcoming curb appeal. Practical updates include a 3-year-old water heater and a recently serviced swamp cooler. This home is being sold "as is." Schedule a showing today.

2810 7th Ave, Pueblo

$399,000

3995094 MLS

Located on a corner lot in downtown Colorado Springs' beautiful Hillside community, this shovel ready, urban infill apartment complex offers 10 luxury, Class A units, with amazing mountain views and immediate proximity to downtown amenities. Take advantage of this property's Opportunity Zone tax benefits, which means you pay zero capital gains taxes on the sale after building and owning the apartments for ten years. This project is ready for builder permits, with all drawings and site variances approved and stamped by the city and tap fees already paid.As Hillside's future anchor point for urban living, all units will feature 9' interior ceilings, 8 tuck-under covered parking spots, 8 storage units, 8 bike storage units, a dedicated dog wash, and electric vehicle charging stations.Investment opportunities like this rarely make it to the open market. Make this one yours today!

703 E Costilla Street, Colorado Springs

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