299 Homes with Colonial Style

Welcome to the vibrant community of Chicago, Illinois, where the charm of Colonial-style homes meets the esteemed educational opportunities offered by the 299 school district. Nestled in the heart of Cook County, this area boasts a rich cultural tapestry, making it an ideal place for families seeking both a beautiful home and a quality education.

The 299 school district is renowned for its commitment to academic excellence and holistic development. With a diverse array of programs and dedicated educators, students are encouraged to explore their interests and reach their full potential. From innovative arts initiatives to robust STEM programs, the schools in this district nurture young minds, preparing them for a successful future. Parents can rest assured knowing their children are receiving a top-notch education in a supportive environment.

As you explore the neighborhood, you'll discover stunning Colonial-style homes that capture the essence of classic American architecture. These timeless residences often feature symmetrical facades, grand entrances, and beautifully landscaped yards, offering both elegance and comfort. Inside, you’ll find spacious layouts perfect for family gatherings and entertaining friends. Many of these homes are equipped with modern amenities while still retaining their historic charm, making them a perfect blend of old and new.

Living in this thriving community means you’re not just investing in a home; you’re investing in a lifestyle filled with educational opportunities, cultural experiences, and a welcoming atmosphere. Whether you’re drawn to the historic allure of Colonial homes or the exceptional educational offerings of the 299 school district, you’ll find that this area has something special for everyone. Come and discover your dream home in Chicago today!

Newest 299 Homes with Colonial Style

$875,000

4 Beds ⋅ 4 Baths ⋅ 12789462 MLS ⋅ ACTIVE Status

LUXURY NEW CONSTRUCTION IN HISTORICAL BEVERLY/MORGAN PARK NEIGHBORHOOD. A 2 STORY Contemporary/Traditional Beauty offering spacious 5 bedrooms, 4 full baths with thoughtfully curated designer finishes throughout. The striking black-and-white exterior features luxury white Hardie board siding, dramatic, black onyx European windows, a covered front porch, and a modern high ceiling lofted attached 2-car garage, creating timeless curb appeal on one of Morgan Park/Beverly's most prestigious sought after tree-lined streets. The open-concept interior is filled with natural light and showcases natural red oak hardwood floors, designer lighting, and refined architectural details. The elegant, Custom "Black White and Oak Design" kitchen is the centerpiece of the home, featuring custom illuminated cabinetry, quartz countertops, a dramatic black statement hood, designer pendant lighting, a stunning 9-foot quartz waterfall island with seating, and the Premium Autograph Series Stainless Steel and Champaign Bronze Commercial Appliance Suite. The adjacent Deck/Patio extends your living space outdoors, making entertaining effortless. A main-level bedroom offers the perfect space for guests, multigenerational living, or a private home office/Podcast Center. Upstairs, the luxurious primary suite serves as a private retreat, featuring dual vanities, a freestanding soaking tub, an oversized walk-in shower, generous walk-in closet space, and a conveniently located bedroom-level laundry room with a top of line all in one washer dryer. Two additional spacious bedrooms and a well- appointed full bath complete the second level, offering comfort and flexibility for family and guests. The finished lower level is designed for entertaining with a spacious family room featuring a custom built-in entertainment center with a bookcase, fireplace, a sophisticated wet bar with wine fridge, a private fifth bedroom, a full bath, and a second laundry room equipped with a Samsung Top loading side by side system with cabinetry and custom counter for all laundry needs. Just off the attached garage, a custom mudroom includes a built-in bench, a spacious coat closet with a stylish barn door, and thoughtfully designed storage. Located just 0.3 miles from the Metra, this exceptional residence offers convenient access to neighborhood restaurants, parks, shopping, and downtown Chicago. Experience timeless architecture, luxury finishes, and modern functionality on Historical Longwood Drive! Location **Location** Location This is the home you always wanted. Schedule your private showing TODAY!

11173 S Longwood Drive, Chicago

$549,900

4 Beds ⋅ 2 Baths ⋅ 12785670 MLS ⋅ ACTIVE Status

Charming Gladstone Park two-flat situated on a desirable corner lot directly across from Gladstone Park! This well-maintained property features two updated units with separate utilities, refreshed kitchens, tile baths, and refinished hardwood floors. The first-floor unit offers an inviting open living space, forced-air heat, and central air conditioning, while the second-floor unit features gas hot water heat and a wall-mounted AC unit. Enjoy a spacious front porch, a lovely yard, and a two-car garage with a covered patio. Conveniently located within walking distance of the Blue Line and Metra, offering easy access to downtown Chicago. A fantastic opportunity for investors or owner-occupants in a great neighborhood! Additional income: $250/month for garage and approx $50/mo for laundry.

5377 N Magnet Avenue, Chicago

$535,000

4 Beds ⋅ 4 Baths ⋅ 12779476 MLS ⋅ ACTIVE Status

** ALL WORK WAS DONE WITH CITY PERMITS** THIS IS A BEAUTIFUL BUILDING, TASTEFULLY RENOVATED FROM TOP TO BOTTOM; EVERYTHING IS NEW (2025- 2026). ONLY THE ROOF IS ABOUT 6 YEARS OLD. BOTH OF THE UNITS HAVE A NICE LAYOUT AND A LOT OF SUNLIGHT. FIRST FLOOR UNIT WITH A COZY KITCHEN WITH WHITE CABINETS, A QUARTZ COUNTERTOP, SPACIOUS LIVING ROOM, DINING ROOM, AND KITCHEN. ONE NICE-SIZE BEDROOM AND LAUNDRY ROOM IN THE BACK. SECOND-FLOOR UNIT; DUPLEX WITH THIRD FLOOR WITH TONS OF SPACE, THREE BEDROOMS ON THE TOP FLOOR; MASTER BEDROOM WITH A FULL BATHROOM AND A PRIVATE DECK. TWO EXTRA BEDROOMS WITH ANOTHER FULL BATHROOM. NEW HARDWOOD FLOORS THROUGHOUT; MAIN LEVEL WITH A HUGE KITCHEN, SPACIOUS LIVING ROOM, DINING ROOM, HALF BATHROOM, A LOT OF SUNLIGHT. LAUNDRY AND MECHANICAL ROOM. PRIVATE BACK YARD, TOO MUCH TO MENTION. THANK YOU FOR SHOWING!

2135 S Millard Avenue, Chicago

$2,295,000

8 Beds ⋅ 6 Baths ⋅ 12702363 MLS ⋅ ACTIVE Status

Located in the heart of the South Kenwood historic landmark district, 4901 S Kimbark Avenue offers a rare opportunity to own a distinguished residence in one of Chicago's most architecturally significant neighborhoods. Surrounded by stately homes, mature trees, and picturesque streets, this exceptional property combines timeless character with an unbeatable location just moments from the University of Chicago campus, Jackson Park, the Museum of Science and Industry, and the lakefront. The imposing 3-story home has impressive curb appeal, including an inviting wrap-around porch and mature plantings. A private side yard provides a verdant refuge for play and outdoor dining. The new 2+ car garage is a real plus. Inside, the 8-bedroom, 5.5 bath home showcases generous living spaces, abundant natural light, and classic architectural details that reflect Kenwood's rich heritage. Spacious formal rooms are complemented by comfortable everyday living areas, creating an ideal setting for both entertaining and daily life. Among the many outstanding features is the beautifully designed modern eat-in kitchen with top-of-the-line appliances and the fully-finished lower level with a spacious recreation room, separate work-out room, and a new full bath. New water service, zoned a/c, and updated systems throughout. The location is second to none. Residents enjoy easy access to acclaimed restaurants, neighborhood cafes, shopping, cultural institutions, Metra and CTA transportation downtown, and the scenic paths and beaches along Lake Michigan. Jackson Park's ongoing improvements and the renowned Obama Presidential Center further enhance the appeal of this vibrant community. Whether you're seeking a remarkable historic residence or an elegant home in one of Chicago's most desirable neighborhoods, 4901 S Kimbark Avenue offers an exceptional blend of architectural character, urban convenience, and enduring value.

4901 S Kimbark Avenue, Chicago

$227,000

2 Beds ⋅ 2 Baths ⋅ 12752595 MLS ⋅ ACTIVE Status

Charming Auburn Gresham Home with Great Potential! Welcome to this all-brick 3-bedroom, 1.5-bath home nestled on a quiet block in the Auburn Gresham community! Featuring a wonderful layout with great space to make your own, this home offers an updated kitchen with blue shaker cabinets, quartz countertops, and a subway tile backsplash. The third bedroom provides additional space and versatility, while the home's layout offers plenty of possibilities to personalize and make it your own. The home offers a great opportunity to add your personal style and make it your own with a few cosmetic updates. The finished basement provides additional living space and includes a washer and dryer. Outside, enjoy a large fenced-in backyard, spacious side yard, and long driveway leading to a 2-car garage-perfect for entertaining family and friends, hosting summer gatherings, or simply enjoying outdoor living. Conveniently located near public transportation, shopping, restaurants, and major expressways, with approximately a 20-minute drive to the Loop. Bring your vision and make this home your own! With a great layout, an updated kitchen, and wonderful outdoor space, this Auburn Gresham property is full of possibilities. Schedule your showing today!

8831 S Eggleston Avenue, Chicago

$254,995

3 Beds ⋅ 2 Baths ⋅ 12756145 MLS ⋅ ACTIVE Status

Welcome to this beautifully updated 3-bedroom, 1.5-bath home in Chicago's Rosemoor neighborhood! This move-in-ready home offers a spacious and functional layout with thoughtful updates throughout. The main level features a bright living room, separate dining area, updated kitchen, and convenient half bath. Upstairs you'll find three comfortable bedrooms and an updated full bathroom. The basement provides additional recreation and utility space, perfect for entertaining, a home office, gym, or additional living space. A screened-in porch offers even more space to relax and enjoy. Major improvements include a new roof, new windows, new A/C compressor, and new water heater, along with an updated kitchen and bathrooms. Conveniently located near the 103rd St. (Rosemoor) Metra Electric station, public transportation, parks, shopping, schools, and everyday neighborhood amenities. With many of the major improvements already completed, this home is ready for its next owner. Property is being sold AS-IS. Schedule your showing today!

10048 S Rhodes Avenue, Chicago

$159,000

4 Beds ⋅ 2 Baths ⋅ 12733858 MLS ⋅ ACTIVE Status

Prime Investment Opportunity - 2 Unit Apartment Building Discover a solid investment opportunity with this well-maintained two-unit building located at 7130 S Green St in Chicago. Both units are currently occupied, providing immediate cash flow for an owner-occupant or investor. Each unit features 2 bedrooms and 1 bathroom, along with functional living space and straightforward layouts that support long-term rental demand. The property offers convenient access to major highways, making transportation simple for residents and commuters. Whether you're expanding your portfolio or securing a dependable income-producing property, this building delivers a strong foundation with stable tenancy already in place. A great option for investors seeking steady rental income from day one.

7130 S Green Street, Chicago

$295,000

3 Beds ⋅ 3 Baths ⋅ 12702552 MLS ⋅ ACTIVE Status

Welcome Home! Beautifully Renovated 4-Bedroom, 3-Bath with Two Master Suites. Step into comfort, peace of mind, and a place you'll be proud to call home. This fully renovated 2-story gem offers everything you need-brand new roof, windows, plumbing, electrical, flooring, walls, countertops-absolutely everything is new, giving you a fresh start with no worries. This spacious layout is perfect for both everyday living and making lasting memories with loved ones. With two master suites, you'll enjoy flexible living options: one on the main level with a walk-in closet and private bath, and another upstairs featuring a private balcony retreat-ideal for morning coffee or quiet evenings. This home has been thoughtfully updated with love and care, and it shows. Let's make your dream a reality. ALL PERMITS PULLED, APPROVED BY CITY OF CHICAGO & QUALIFY FOR UP TO $50,000 CHICAGO HOMEGROWN GRANT. CONTACT LISTINGT AGENT ANTOINE BAKER FOR MORE INFORMATION ON GRANT & PROPERTY.

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299 Homes with Colonial Style

Newest 299 Homes with Colonial Style

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