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$1,299,000
5 Beds 6 Baths 12714372 MLS NEW Status
Welcome to this exceptional Greystone vintage 3-unit building offering 5 bedrooms, 5 full bathrooms, and 1 half bathroom, perfectly blending classic Chicago charm with modern comfort. Featuring beautiful landscaping, a fenced backyard, and thoughtfully designed living spaces, this remarkable property presents an outstanding opportunity for both homeowners and investors. A stunning hardwood staircase welcomes you through the main entrance, providing access to both the first- and second-floor units. Let's begin with the second-floor residence. As you enter, you're greeted by a bright and spacious living room, highlighted by a beautiful English skylight lantern above the foyer and oversized windows that fill the home with abundant natural light. Located just off the living room, the primary suite offers a private retreat with a separate sitting area, generous closet space, direct access to a private balcony, and large windows that create a warm and inviting atmosphere. On the opposite side of the living room, the second bedroom features a walk-in closet and ample living space. The unit includes two full bathrooms-one with a luxurious walk-in steam shower and the other with a relaxing soaking tub. Conveniently located between the bedrooms, the dedicated laundry room adds everyday comfort and functionality. Toward the rear of the home, the open-concept family room and kitchen create the perfect gathering space, centered around a cozy fireplace with both gas and wood-burning options. The kitchen is beautifully appointed with stainless steel appliances, a large center island with breakfast bar seating, pantry storage, and expansive windows that surround the space with exceptional natural light. The first-floor unit mirrors the upper-level layout, offering incredible flexibility for multi-generational living or rental income. It features its own fully equipped kitchen, two full bathrooms, a dedicated laundry room, and an added layer of security with alarm sensors installed on every window. From the rear staircase, you'll find access to the basement studio unit. Before entering the studio, you'll pass a spacious recreation room, utility area, and a separate laundry room dedicated exclusively to the lower-level residence. Inside the studio, you'll find a thoughtfully designed living space featuring a full kitchen with stainless steel appliances, a microwave, air fryer, and range hood. The studio also includes one full bathroom, one half bathroom, and generous closet space, creating a comfortable and functional living arrangement that's perfect for guests, extended family, or rental income. The rear staircase also provides convenient access to the rooftop, the first-floor unit, and the second-floor residence, making movement throughout the building both practical and efficient. Designed with long-term comfort and peace of mind, the property is equipped with multiple tankless water heaters, multiple zoned furnaces, multiple sump pumps, and a comprehensive security system, showcasing the exceptional care and quality invested throughout the home. Step outside to enjoy the beautifully landscaped, fenced backyard featuring a brick paver patio, mature landscaping, and multiple outdoor seating areas-an ideal setting for entertaining family and friends or simply relaxing outdoors. Conveniently located near public transportation, bus routes, restaurants, grocery stores, shopping, and everyday conveniences, this exceptional Greystone offers the perfect combination of timeless Chicago architecture, modern functionality, and outstanding investment potential. Don't miss this rare opportunity to own a versatile, meticulously maintained multi-unit property that seamlessly blends historic character, modern upgrades, and exceptional income potential-all in one of Chicago's most desirable neighborhoods.

4448 N Tripp Avenue, Chicago

$1,100,000
13 Beds 8 Baths 12714290 MLS NEW Status
RARE investment opportunity in the heart of Bronzeville-a beautifully restored 1903 historic mansion thoughtfully converted into four oversized luxury apartments on a rare double-wide lot with additional value-add potential. This architect-designed 2025 renovation masterfully blends timeless vintage character with modern functionality, preserving original stained and leaded glass, intricate woodwork, hardwood floors, pocket doors, fireplaces, built-ins, and original doors throughout while introducing all new plumbing, upgraded 400-amp electrical service with separate meters, water heaters, insulation, custom kitchens, designer bathrooms, and individual HVAC/mini-split systems. Residents enjoy exceptional outdoor amenities including a welcoming front porch, private rear decks, side yard, and common courtyard patio. A substantial brick coach house provides three garage parking spaces on the main level while the upper level offers an outstanding opportunity for future expansion. Previously configured as additional living space, it presents tremendous potential for a fifth residential unit, guest suite, studio, office, or other income-producing use, subject to buyer verification and any required approvals. Each apartment occupies nearly an entire floor and benefits from four exposures, flooding the homes with natural light while offering spacious layouts, large bedrooms, in-unit laundry, private storage, and thoughtfully designed kitchens featuring soft-close cabinetry, solid surface countertops, induction cooking, upgraded appliances, designer backsplashes, and vent hoods. Bathrooms have been beautifully updated with a combination of walk-in showers, marble flooring, restored clawfoot tubs, and custom vanities. Quietly situated on a charming residential street surrounded primarily by single-family homes, this truly one-of-a-kind turnkey investment combines luxury finishes, irreplaceable historic architecture, and strong long-term rental appeal, with the added opportunity to further enhance value through the coach house. A rare offering in one of Chicago's most dynamic and appreciating neighborhoods.

4541 S Forrestville Avenue, Chicago

$319,900
4 Beds 2 Baths 12709745 MLS NEW Status
Outstanding investment opportunity in a classic Elgin two-flat located in the Spring-Douglas historical district, offering immediate cash flow plus long-term upside! This well-maintained up/down duplex features two generously sized 2-bedroom units full of vintage character - high ceilings, natural millwork, a charming bay window, and gleaming hardwood floors throughout. Easy walking distance to schools, library and downtown. Unit 1 (421) - VACANT & MOVE-IN READY: Freshly painted, professionally cleaned, and updated with new kitchen flooring - ready to lease at market rent or perfect for an owner-occupant. This spacious 2-bedroom layout includes a primary bedroom and second bedroom, both with generously sized closets, plus a separate living room and family room for flexible everyday living. The kitchen and dining area form one large, open, adjoined space - ideal for entertaining - along with a full bath. Get top rent from day one with this beautifully refreshed unit. Unit 2 (419) - LONG-TERM, STABLE TENANT: A comfortable 2-bedroom layout with a functional galley kitchen, spacious living room, and full bath. Currently occupied on a month-to-month lease, providing immediate income with flexibility for future rent increases or owner use. Additional highlights include a freshly painted basement for extra storage, a detached 2-car garage, and a generous fenced yard - all located just minutes from downtown Elgin, Metra, shopping, and dining. Whether you're an investor looking to add a cash-flowing asset to your portfolio or an owner-occupant hoping to live in one unit while renting the other, this solid two-flat checks every box: updated, spacious, and priced to perform. Schedule your showing today (Lower unit can be a go & show, upstairs requires 48 hour notice.)

419-421 N Spring Street, Elgin

$1,145,000
10 Beds 5 Baths 12713885 MLS NEW Status
An exceptional opportunity to acquire a trophy three-flat in one of Evanston's most desirable locations, offering the rare combination of strong income potential, owner-occupant flexibility, and extraordinary parking. Set on a beautifully maintained lot with an expansive backyard, this impressive multi-family property features two oversized residences and a ground level garden unit. Units 2 and 3 offer an increasingly hard-to-find layout with four spacious bedrooms and two full baths, providing exceptional appeal for tenants seeking the comfort and scale of a single-family home with the convenience of apartment living. Generous room sizes, abundant natural light, and thoughtfully designed floor plans create an inviting living experience throughout. A true standout feature attached and detached garages suitable for 6 cars, a remarkable amenity seldom found in Evanston and a significant value-add for both owners and tenants alike. Whether you're an investor seeking stable cash flow and long-term appreciation, a live-in owner looking to offset expenses with rental income, or a multi-generational buyer searching for flexibility, this property delivers. Positioned just moments from Evanston's vibrant dining, shopping, parks, public transportation, and lakefront amenities, 1016 Austin offers the ideal blend of location, scale, and investment fundamentals. Opportunities to acquire a building of this caliber, with this unit mix, oversized garage capacity, and exceptional outdoor space, are few and far between.

1016 Austin Street, Evanston

$965,000
4 Beds 2 Baths 12710833 MLS NEW Status
Prime Bucktown Location - Solid Brick 2-Flat! This meticulously maintained, solid-brick multi-unit building has been lovingly cared for by the same owner for many years. Featuring 8.5-foot ceiling heights in a very clean heated basement, it offers an excellent opportunity for a live-in landlord, duplex or a savvy investor looking to add a high-performing asset to their portfolio. Each of the two units boasts 2 bedrooms, an updated kitchen, and an updated bathroom. The building features a functional open floor plan filled with natural light, beautifully refinished hardwood flooring, and fresh paint throughout. Additional conveniences include a mudroom in each unit and separate forced-air heating and central air conditioning. Recent updates include: New tear-off roof (with new plywood) on the main building and garage New gutters, fascia, and soffits New siding on the rear of the building Newer windows throughout New cement slab and walkway leading to the basement Newer water heater Refinished hardwood floors Fresh paint throughout Additional highlights include in-unit laundry on the first floor (with basement laundry for the second floor), a spacious paved patio and backyard, low taxes, and RS-3 zoning. The attached garage also features a new tear-off roof, new siding, and a new cement slab.Located on a charming tree-lined street in desirable Bucktown, this home is within walking distance to Holstein Park, the 606 Trail, world-class cafes, restaurants, shops, and nightlife. Enjoy easy access to the El, Metra, buses, and the Kennedy Expressway. Comparable new-construction single-family homes in the area are selling for millions. This turnkey, vacant, and move-in-ready building is priced to sell-don't miss this rare opportunity!

2329 W Mclean Avenue, Chicago

$595,000
6 Beds 4 Baths 12664627 MLS NEW Status
Desirable Mid-Century Modern solid brick 2-flat offering 3,236 sq ft of living space on a wide 35' x 124' lot available on a tree lined street surrounded by single family homes in West Ridge. Rare opportunity for investors & owner occupants looking to live in one of the units & generate income from the other. The 1st floor unit has 4-spacious bedrooms, all w/good closet space, the 2nd floor unit has 2 bedrooms - both units have 1.5 baths & their own HVAC units w/central air. The half baths have updated vanities & toilets, the full baths have original floors and wall tiles. The living & dining room layouts in both units are classic mid century modern, with plenty of space for various furniture arrangements. The basement is unfinished w/additional storage lockers, a newer washer/dryer, slop sink, 2 HVAC units, 2 hot water tanks & could be a duplex down opportunity. There's a 2.5 car garage w/an electric garage opener & newer side door. Prime location just blocks from Legion Park, w/51-acres that runs along the North Branch of the Chicago River, w/walking & bike trails, playgrounds & basketball. The building is centrally located halfway between LSD & the Edens for easy access to the Northern suburbs or Downtown. There's a Metra station on Peterson & Ridge 1.7 miles east of the property. Close by is the vibrant Devon Corridor, w/grocers, restaurants & clothing boutiques and Kedzie Ave w/ Middle Eastern cafes, restaurants & grocery stores. The building is located between Lincoln Square w/the CTA Brown Line & Andersonville/Edgewater w/the CTA Red Line. Both Lincoln Square and Andersonville have their own unique culture w/outdoor cafes, shops, restaurants, music venues, gyms, parks, the river and the lakefront. Bring your vision and make the most of this rare investment opportunity in a diverse thriving central city locale. The building is vacant and being sold As Is.

6025 N Sacramento Avenue, Chicago

$665,000
6 Beds 4 Baths 12710369 MLS NEW Status
Rare opportunity to acquire a classic Chicago four-flat on 3,150 square foot lot just one block from iconic Logan Boulevard. Offering approximately 3,475 square feet above grade plus a full unfinished basement, a detached two-car garage, and a fenced backyard, this is the type of property that rarely becomes available in one of Logan Square's most desirable locations. Built in 1897, the building features an ideal unit mix of two one-bedroom residences and two spacious two-bedroom-plus-den apartments. Generous room sizes, flexible floor plans, private rear decks, and original stained wood doors with period hardware showcase the timeless craftsmanship and architectural character that make Chicago's vintage buildings so enduring. The property currently generates $4,500 per month in rental income, with existing rents remaining well below prevailing Logan Square market rates. The full unfinished basement offers abundant storage and future potential, while the detached two-car garage and private backyard provide amenities that are increasingly difficult to find in the neighborhood. This is not a turnkey investment. The building has seen limited updates over the past several decades and is being sold as-is. Buyers should anticipate deferred maintenance, repairs, and modernization. The value lies in the fundamentals: oversized apartments, flexible layouts, original architectural details, outdoor space, garage parking, and an irreplaceable location. Located just steps from Logan Boulevard and surrounded by acclaimed restaurants, neighborhood cafes, parks, public transportation, and everything that has made Logan Square one of Chicago's most sought-after neighborhoods, 2643 N. California Avenue presents an exceptional opportunity to restore, reposition, and realize the full potential of a classic Chicago investment property. Within the boundaries of the 606 Ordinance.

2643 N California Avenue, Chicago

$674,999
9 Beds 3 Baths 12713376 MLS NEW Status
This brick multi-unit building in Albany Park is a rare house-hacker and investor opportunity, with 3 spacious 3-bedroom units, a fully finished lower level, and recent big-ticket upgrades already done. These large 3 bedroom units, each with a primary bedroom, formal dining, sunlit living room, and a bright sun room. Market rent runs approximately $2,300 to $2,600 per unit. Expansive finished lower level with its own kitchen and full bath, perfect for extended-family living, a private guest suite, or generous owner space. NEW building roof and NEW garage roof, so the major capital expenses are already handled. Detached garage plus an additional parking pad, opening the door to extra parking rental income. On-site coin-operated laundry for another stream of supplemental revenue. ADU upside: Zoned multi-unit residential, where Chicago's permanent Additional Dwelling Unit ordinance (effective April 2026) now permits ADUs by-right. Buyers may have a path to explore legalizing additional living space as a conforming ADU, adding a potential third income stream. Buyer to verify ADU eligibility and approvals with the City of Chicago Steps to the CTA Brown Line, Kedzie and Lawrence dining and shopping, Ronan Park, and the Chicago River trail, with fast access to downtown and the expressways. Albany Park is one of the city's most in-demand rental corridors, and tenants want to be here. Live in one unit, rent the others, and let parking and laundry pad your bottom line. Whether you are building generational wealth, buying your first investment, or growing a portfolio, this is the kind of Albany Park building that does not last. Schedule your private showing today.

4918 N Monticello Avenue, Chicago

$599,000
4 Beds 2 Baths 12699273 MLS NEW Status
Welcome to this timeless Greystone Two Flat, ideally situated in the prestigious Frank Lloyd Wright Historic District within the heart of Downtown Oak Park, where historic elegance meets modern opportunity. This exceptional property blends enduring architectural character with thoughtful updates, making it an outstanding opportunity for both owner-occupants and investors. The first floor unit has been tastefully refreshed with new interior paint all throughout, newer quartz countertops, stainless steel appliances, updated lighting, two spacious bedrooms, a beautifully appointed full bath, and a heated rear sunroom that serves as the perfect den retreat and/or an office/entertaining space. The second floor unit offers an equally inviting floor plan featuring two spacious bedrooms, a full bath, and an elegant front flex room that can be suited as a home office, library, sitting room, or additional living space and its heated rear sunroom creates yet another warm and versatile setting while preserving the home's original architectural charm. Every detail reflects pride of ownership. Additional highlights include newer windows throughout, hardwood floors throughout both units, separate utilities, an unfinished basement offering generous storage along with a washer and dryer for owner/tenant convenience and a beautifully reimagined front porch that welcomes relaxation, guests and seamless curb appeal. One of the property's most extraordinary features is its three private exterior parking spaces, located to side of the home, a true luxury in this coveted neighborhood and the only property on the block to offer dedicated parking. Whether envisioned as an owner-occupied investment, an elegant multigenerational residence, or a premier addition to a real estate portfolio, the possibilities are remarkable. Live in one residence while generating rental income from the other, or maximize returns with both units. The second-floor is occupied by a long-term tenant paying below market rent, presenting immediate value add potential. Both units offer the opportunity to command rental income approaching $2,400 per month, creating an attractive investment profile in one of Chicagoland's most sought after communities. Perfectly positioned in the vibrant heart of Downtown Oak Park, residents enjoy an irreplaceable location and walkable lifestyle surrounded by acclaimed restaurants, boutique shopping, artisan cafes, wellness studios, entertainment, neighborhood parks, and everyday conveniences. Proximity to Downtown Forest Park, the CTA Green Line, Metra, and an effortless commute to Downtown Chicago place the very best of the city and suburbs within easy reach. This is more than a two-flat. It is an opportunity to own an enduring piece of Oak Park's architectural legacy while embracing the lifestyle that one of Chicagoland's most desirable historic neighborhoods has to offer. Schedule your private showing today! Multiple offers received!

212 N Marion Street, Oak Park

$279,900
4 Beds 4 Baths 12705159 MLS NEW Status
Turn-key investment opportunity or ideal owner-occupied 2-flat in a prime Woodstock location! The first-floor unit is currently in the process of moving out, creating an outstanding opportunity for an owner-occupant to move right in while generating immediate rental income from the occupied second-floor unit. This maintained property has been updated over the years, white trim and doors, hardwood and laminate flooring, updated lighting, and loads of windows that fill both units with natural light. The first-floor unit offers three bedrooms, a white cabinet kitchen complete with updated appliances, large living room and an updated full bath and half bath. The second-floor unit features one bedroom, large living room, nicely sized kitchen and updated bathrooms - one full and one half. Additional features include separate utilities for each unit, washer and dryer hookups in the basement (currently only the 1st floor unit has access to the basement), and a low-maintenance setup where tenants pay all utilities and are responsible for lawn care. Whether you're looking to live in one unit or expand your investment portfolio with a true turn-key property, this is an exceptional opportunity. Conveniently located just minutes from historic Downtown Woodstock Square, shopping, restaurants, schools, parks, and commuter routes. Don't miss your chance to own a versatile income-producing property in one of Woodstock's most desirable locations!

731 N Madison Street, Woodstock

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