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Rare Single-Family Home in the Heart of Wicker Park with Private Parking & Designer Outdoor Living A truly rare opportunity to own a 2,912 square foot SINGLE FAMILY STANDALONE home in one of Chicago's most vibrant neighborhoods. Located on Damen Avenue just one block north of Division Street, this exceptional property offers the space, privacy, and lifestyle that are incredibly difficult to find in Wicker Park. The home features 4 bedrooms and 3 full bathrooms, along with a recently remodeled interior showcasing brand new hardwood flooring throughout. Offered fully furnished and fully stocked, this property is completely turnkey-perfect as a primary residence, second home, or investment opportunity. One of the standout features is the rare private parking area accommodating 2-3 vehicles, a true luxury in this location. Even more impressive is the professionally designed fenced backyard, creating a private outdoor retreat rarely found in the city. The space has been thoughtfully upgraded with a premium turf lawn, professional landscaping, and multiple entertainment zones, including a seating area with fire pit, dining table and chairs, sun loungers, and a fully equipped outdoor kitchen featuring a natural gas grill, granite countertops, and custom-built wood grill enclosure. Situated in the heart of Wicker Park, the home is just steps from the energy of Division Street and is walkable to countless restaurants, boutiques, coffee shops, parks, and nightlife in Wicker Park, Bucktown, and Logan Square. Commuting is effortless with quick access to the Blue Line train and multiple public transportation options. Opportunities to own a move-in ready single-family home with private parking and a fully built-out backyard oasis in this location are exceptionally limited. This is city living at its finest-combining space, convenience, and lifestyle in one remarkable property.

4 Beds ⋅ 3 Baths ⋅ 12766467 MLS

Rare Single-Family Home in the Heart of Wicker Park with Private Parking & Designer Outdoor Living A truly rare opportunity to own a 2,912 square foot SINGLE FAMILY STANDALONE home in one of Chicago's most vibrant neighborhoods. Located on Damen Avenue just one block north of Division Street, this exceptional property offers the space, privacy, and lifestyle that are incredibly difficult to find in Wicker Park. The home features 4 bedrooms and 3 full bathrooms, along with a recently remodeled interior showcasing brand new hardwood flooring throughout. Offered fully furnished and fully stocked, this property is completely turnkey-perfect as a primary residence, second home, or investment opportunity. One of the standout features is the rare private parking area accommodating 2-3 vehicles, a true luxury in this location. Even more impressive is the professionally designed fenced backyard, creating a private outdoor retreat rarely found in the city. The space has been thoughtfully upgraded with a premium turf lawn, professional landscaping, and multiple entertainment zones, including a seating area with fire pit, dining table and chairs, sun loungers, and a fully equipped outdoor kitchen featuring a natural gas grill, granite countertops, and custom-built wood grill enclosure. Situated in the heart of Wicker Park, the home is just steps from the energy of Division Street and is walkable to countless restaurants, boutiques, coffee shops, parks, and nightlife in Wicker Park, Bucktown, and Logan Square. Commuting is effortless with quick access to the Blue Line train and multiple public transportation options. Opportunities to own a move-in ready single-family home with private parking and a fully built-out backyard oasis in this location are exceptionally limited. This is city living at its finest-combining space, convenience, and lifestyle in one remarkable property.

1235 N Damen Avenue, Chicago

1395 N Milwaukee Avenue Unit #3E, Chicago

$565,000

Positioned in the heart of Wicker Park, this 2-bedroom, 2-bathroom top floor unit offers stunning views of this beloved Chicago neighborhood. Easily accessible via elevator, this unit opens up into a beautiful open layout featuring Brazilian cherry floors, a granite lined gas-powered fireplace, and plenty of natural lighting from massive western facing windows. The kitchen features stainless steel appliances and a sweeping granite countertop that extends out into an eat-in bar and opens seamlessly into the combined living and dining spaces. Together they create a balance between every day comfortable living and hosting friends for a big game or a big dinner. When you're ready to call it a night you head back to your primary bedroom with natural light cascading in from the sliding glass doors, walk-in closet, and ensuite bathroom. The primary bath offers a dual vanity, separate shower, and whirlpool bath that will let you unwind after a long day. The secondary bedroom also has picturesque windows and a walk-in closet, and it's spacious enough to comfortably fit a queen-sized bed. Offering an abundance of storage throughout, an updated guest bath, and in-unit laundry this unit covers all the bases. Outdoor spaces include a large front balcony with plenty of room for grilling or gardening, a cozy private balcony off the back of the primary bedroom for some quiet morning coffee, and a shared access rooftop deck with sweeping unmatched views of the Chicago skyline. This unit offers the best combination of private convenience and public accessibility with an attached private 1 car garage and by being just 2 blocks away from the Damen or Ashland blue line stops. Milwaukee Avenue puts you steps away from all Wicker Park has to offer including the 606 trail, wonderful boutiques, nightlife, entertainment venues and incredible restaurants this neighborhood is known for.

2 Beds ⋅ 2 Baths ⋅ 12759031 MLS

Positioned in the heart of Wicker Park, this 2-bedroom, 2-bathroom top floor unit offers stunning views of this beloved Chicago neighborhood. Easily accessible via elevator, this unit opens up into a beautiful open layout featuring Brazilian cherry floors, a granite lined gas-powered fireplace, and plenty of natural lighting from massive western facing windows. The kitchen features stainless steel appliances and a sweeping granite countertop that extends out into an eat-in bar and opens seamlessly into the combined living and dining spaces. Together they create a balance between every day comfortable living and hosting friends for a big game or a big dinner. When you're ready to call it a night you head back to your primary bedroom with natural light cascading in from the sliding glass doors, walk-in closet, and ensuite bathroom. The primary bath offers a dual vanity, separate shower, and whirlpool bath that will let you unwind after a long day. The secondary bedroom also has picturesque windows and a walk-in closet, and it's spacious enough to comfortably fit a queen-sized bed. Offering an abundance of storage throughout, an updated guest bath, and in-unit laundry this unit covers all the bases. Outdoor spaces include a large front balcony with plenty of room for grilling or gardening, a cozy private balcony off the back of the primary bedroom for some quiet morning coffee, and a shared access rooftop deck with sweeping unmatched views of the Chicago skyline. This unit offers the best combination of private convenience and public accessibility with an attached private 1 car garage and by being just 2 blocks away from the Damen or Ashland blue line stops. Milwaukee Avenue puts you steps away from all Wicker Park has to offer including the 606 trail, wonderful boutiques, nightlife, entertainment venues and incredible restaurants this neighborhood is known for.

1395 N Milwaukee Avenue Unit #3E, Chicago

2136 W Evergreen Avenue Unit #1B, Chicago

$659,900

Must see duplex in the heart of Wicker Park, featuring 3 bedrooms, 3 full bathrooms, and a full finished basement. Enjoy an unbeatable location near the Blue Line, great restaurants, shopping, nightlife, and everything the Wicker Park neighborhood has to offer. The main level features a ideal, functional layout with fresh paint, gleaming hardwood floors, and updated lighting throughout to. The updated kitchen offers stainless steel appliances, 42-inch cabinets with crown moulding, granite counters, and eat-in table space / dining area. The living area features a corner gas fireplace and access to a private balcony. The primary ensuite includes a beautifully remodeled private bathroom completed in 2025 & large walk-in closet! The additional main-level bathroom features heated floors. The full finished basement provides additional living space with a versatile room perfect for a home office, gym, or flex space, along with a full bathroom remodeled in 2019 with heated floors. Additional updates include the furnace, A/C, and water heater in 2019, plus a UV furnace filter. A great opportunity to enjoy plenty of space in one of Chicago's most desirable neighborhoods.

2 Beds ⋅ 3 Baths ⋅ 12734964 MLS

Must see duplex in the heart of Wicker Park, featuring 3 bedrooms, 3 full bathrooms, and a full finished basement. Enjoy an unbeatable location near the Blue Line, great restaurants, shopping, nightlife, and everything the Wicker Park neighborhood has to offer. The main level features a ideal, functional layout with fresh paint, gleaming hardwood floors, and updated lighting throughout to. The updated kitchen offers stainless steel appliances, 42-inch cabinets with crown moulding, granite counters, and eat-in table space / dining area. The living area features a corner gas fireplace and access to a private balcony. The primary ensuite includes a beautifully remodeled private bathroom completed in 2025 & large walk-in closet! The additional main-level bathroom features heated floors. The full finished basement provides additional living space with a versatile room perfect for a home office, gym, or flex space, along with a full bathroom remodeled in 2019 with heated floors. Additional updates include the furnace, A/C, and water heater in 2019, plus a UV furnace filter. A great opportunity to enjoy plenty of space in one of Chicago's most desirable neighborhoods.

2136 W Evergreen Avenue Unit #1B, Chicago

$2,199,800

Incredible 4 bedroom, 4.5 bathroom approximately 5,000-square-foot Wicker Park single family home including an oversized and high speed commercial elevator accessing all 5 floors! Multiple outdoor spaces including an outdoor rooftop hot tub and additional lap pool above garage deck! Custom all-brick and stone exterior construction, top-floor sunroom/ entertainment space includes, wet bar, double roofdecks with incredible city and sunset views. Newly updated kitchen includes Sub-Zero and Wolf appliances plus built-in Miele espresso machine. Full-floor primary suite includes, massive walk-in closet, gas fireplace, large separate steam shower and soaking tub. Lower level includes radiant floor heating, second family room, gym and wine room. The heated garage features 14' ceilings, lift-ready capacity & a 240V/60A Tesla charger. Freshly repainted in 2026. Steps to the 606 Trail, Milwaukee Ave boutiques & Division St dining - a turnkey retreat in Chicago's most vibrant corridor.

4 Beds ⋅ 5 Baths ⋅ 12718791 MLS

Incredible 4 bedroom, 4.5 bathroom approximately 5,000-square-foot Wicker Park single family home including an oversized and high speed commercial elevator accessing all 5 floors! Multiple outdoor spaces including an outdoor rooftop hot tub and additional lap pool above garage deck! Custom all-brick and stone exterior construction, top-floor sunroom/ entertainment space includes, wet bar, double roofdecks with incredible city and sunset views. Newly updated kitchen includes Sub-Zero and Wolf appliances plus built-in Miele espresso machine. Full-floor primary suite includes, massive walk-in closet, gas fireplace, large separate steam shower and soaking tub. Lower level includes radiant floor heating, second family room, gym and wine room. The heated garage features 14' ceilings, lift-ready capacity & a 240V/60A Tesla charger. Freshly repainted in 2026. Steps to the 606 Trail, Milwaukee Ave boutiques & Division St dining - a turnkey retreat in Chicago's most vibrant corridor.

1220 N Damen Avenue, Chicago

$1,399,000

Opportunity to purchase a large 3 unit building in a prime Wicker Park location. The top unit is a duplex-up with 3 large bedrooms and 2 bathrooms, multiple living spaces, and in-unit laundry. There are two bedrooms on the main level, with living, dining and kitchen; and the top level has a large bedroom and bathroom, with an additional living room that steps out to a private rooftop deck with great city views. The middle unit has 3 bedrooms and 2 baths and the lower unit has 2 beds and 1 bath. All units have hardwood floors, great ceiling height and abundant light, HVAC and access the laundry. The two car garage is built out with a common roofdeck. Walkable to all Wicker Park has to offer, including six corners, the Milwaukee corridor, the Damen and Division Blue Line stops. Perfect as an owner-occupant or investment play.

8 Beds ⋅ 5 Baths ⋅ 12711707 MLS

Opportunity to purchase a large 3 unit building in a prime Wicker Park location. The top unit is a duplex-up with 3 large bedrooms and 2 bathrooms, multiple living spaces, and in-unit laundry. There are two bedrooms on the main level, with living, dining and kitchen; and the top level has a large bedroom and bathroom, with an additional living room that steps out to a private rooftop deck with great city views. The middle unit has 3 bedrooms and 2 baths and the lower unit has 2 beds and 1 bath. All units have hardwood floors, great ceiling height and abundant light, HVAC and access the laundry. The two car garage is built out with a common roofdeck. Walkable to all Wicker Park has to offer, including six corners, the Milwaukee corridor, the Damen and Division Blue Line stops. Perfect as an owner-occupant or investment play.

1721 W Julian Street, Chicago

$435,000

Experience boutique new construction in the heart of Wicker Park. This exclusive elevator building offers just 12 thoughtfully designed residences, each featuring a bright corner layout with 2 bedrooms and 2 bathrooms. Every home includes access to an expansive shared rooftop terrace with a private, designated section for each residence-perfect for entertaining, relaxing, and enjoying skyline views. Designed with modern living in mind, the interiors showcase wide-plank laminate hardwood flooring, sleek custom kitchens with quartz countertops, premium finishes, and spa-inspired bathrooms that blend style with everyday functionality. Spacious, open-concept floor plans are filled with natural light, creating an inviting atmosphere throughout. Perfectly situated just steps from the renowned restaurants, boutiques, cafes, and nightlife along Division Street and Milwaukee Avenue, this location offers the very best of Wicker Park at your doorstep. A rare opportunity to own new construction in one of Chicago's most desirable neighborhoods. Explore the property in 3D by clicking the 3D Tour button and experience every detail from the comfort of your home.

2 Beds ⋅ 2 Baths ⋅ 12699612 MLS

Experience boutique new construction in the heart of Wicker Park. This exclusive elevator building offers just 12 thoughtfully designed residences, each featuring a bright corner layout with 2 bedrooms and 2 bathrooms. Every home includes access to an expansive shared rooftop terrace with a private, designated section for each residence-perfect for entertaining, relaxing, and enjoying skyline views. Designed with modern living in mind, the interiors showcase wide-plank laminate hardwood flooring, sleek custom kitchens with quartz countertops, premium finishes, and spa-inspired bathrooms that blend style with everyday functionality. Spacious, open-concept floor plans are filled with natural light, creating an inviting atmosphere throughout. Perfectly situated just steps from the renowned restaurants, boutiques, cafes, and nightlife along Division Street and Milwaukee Avenue, this location offers the very best of Wicker Park at your doorstep. A rare opportunity to own new construction in one of Chicago's most desirable neighborhoods. Explore the property in 3D by clicking the 3D Tour button and experience every detail from the comfort of your home.

1355 N Western Avenue Unit #2B, Chicago

$599,000

Top tier location! 1,650 sqft jumbo wide 2 bedroom! Most 2-bedrooms in this neighborhood give you 1,400 square feet, arranged front to back. This one is different. At 1,650 square feet, the 21' wide living room and dining room sit side by side, and the difference is immediate the moment you walk in. There's room to breathe, room for a proper dinner party, room to have two conversations happening at once. The open living space anchors around a gas fireplace and hardwood floors throughout. room for more than a sectional. The kitchen is the heart of the home with beverage fridge and open with large peninsula for drinks and charcuterie. Two 21-ft private outdoor spaces: a covered rear deck for morning coffee and a front balcony that runs the full length of the condo, with front-row views of one of the most walkable stretches in Chicago. Both bedrooms are unusually generous. The primary suite is exceptional for this price point, a true retreat with a jumbo deep walk-in closet. Primary spa bath featuring double vanity, soaking tub, and separate glass shower. The second bedroom comfortably fits a king, plus a desk or peloton. New washer/dryer, central HVAC, 1 exterior parking included. Steps from the Blue Line, Paradise Park, hot new Deliz Italian Steakhouse, Stan's Donuts, Big Star, and Dove's Luncheonette. Walk to the Wicker Park farmers market and dog park, the Robey hotel and cafe, the new Barnes and Noble, and the 606 Trail. The full energy of one of Chicago's most walkable neighborhoods, right outside your door. Can be sold furnished.

2 Beds ⋅ 2 Baths ⋅ 12657313 MLS

Top tier location! 1,650 sqft jumbo wide 2 bedroom! Most 2-bedrooms in this neighborhood give you 1,400 square feet, arranged front to back. This one is different. At 1,650 square feet, the 21' wide living room and dining room sit side by side, and the difference is immediate the moment you walk in. There's room to breathe, room for a proper dinner party, room to have two conversations happening at once. The open living space anchors around a gas fireplace and hardwood floors throughout. room for more than a sectional. The kitchen is the heart of the home with beverage fridge and open with large peninsula for drinks and charcuterie. Two 21-ft private outdoor spaces: a covered rear deck for morning coffee and a front balcony that runs the full length of the condo, with front-row views of one of the most walkable stretches in Chicago. Both bedrooms are unusually generous. The primary suite is exceptional for this price point, a true retreat with a jumbo deep walk-in closet. Primary spa bath featuring double vanity, soaking tub, and separate glass shower. The second bedroom comfortably fits a king, plus a desk or peloton. New washer/dryer, central HVAC, 1 exterior parking included. Steps from the Blue Line, Paradise Park, hot new Deliz Italian Steakhouse, Stan's Donuts, Big Star, and Dove's Luncheonette. Walk to the Wicker Park farmers market and dog park, the Robey hotel and cafe, the new Barnes and Noble, and the 606 Trail. The full energy of one of Chicago's most walkable neighborhoods, right outside your door. Can be sold furnished.

1909 W North Avenue Unit #2, Chicago

$4,695,000

A sophisticated presence, landmark status, architectural integrity, and an unprecedented outdoor footprint for Wicker Park, 1407 N. Hoyne Ave. is a one-of-a-kind opportunity for the homeowner who wants an expansive city estate with pedigree and a modern program. Originally built for beer baron John H. Rapp in 1886, this 8250 SqFt-square-foot, 5 bed/4.3 bath single-family home underwent a multi-year renovation and restoration by Rugo Raff Architects. Preserving elements of its Victorian charm while optimizing sightlines and integrating first-class finishes was paramount. This special home's unheard of 98' x 110' lot affords multiple green spaces, including a deep front yard with mature landscaping, a side yard with raised garden beds and a European-style pergola. Inside, an elegant entry plus an oval-shaped entry hall link to a lovely living room with an abundance of natural light, a traditional turret, and a wood-burning fireplace, and a formal dining room just beyond with hand-scraped walnut floors. The custom chef's kitchen stuns with O'Brien Harris cabinetry, white quartzite countertops, professional-grade Wolf/Sub-Zero appliances, an herb garden, a full butler's pantry, a breakfast dining space with banquette seating, and a built-in desk. The main level also features an intimate family room with built-in walnut cabinetry and a chic beverage center, and two beautiful limestone terraces accessed via French doors: a 12' x 23' west terrace for open-air entertaining and a 12' x 17' side terrace that's perfectly appointed for large-scale alfresco dining with an outdoor kitchen and a built-in grill. A striking example of this home's flawless interior architecture is the centrally located, curving suspended staircase. The second level is devoted to two secondary bedrooms (one with custom bunk beds), the first of two laundry rooms, and an impressively spacious primary suite with a sitting area, a custom dressing room, a walk-in closet, and a marble-clad ensuite bath with two vanities, a soaking tub, and a deluxe shower. The third floor presents two designer offices--a handsome den with knotty alder wood floors and a gas fireplace, a cozy den with a wet bar, an exercise room, and yet another polished guest bedroom. But there's more... This truly magnificent home also comes complete with a fully finished garden level with a massive playroom that opens onto a basement terrace, a wine room, a kitchenette, another large guest bedroom with den perfect for related living, a second laundry room, a walk-in storage room, and a custom mudroom that connects to an attached garage. Additional callout details and amenities include restored original doors and hardware, custom woodwork and trim throughout, designer lighting and wallcoverings throughout, four total fireplaces, 97 Marvin windows, a Lutron lighting system, self-irrigating planters on both terraces, and an excess of custom interior storage. Walking distance to Wicker Park proper and the world-class shopping and dining that extends from the neighborhood's famed Six Corners, 1407 N. Hoyne Ave. is a one-of-a-kind home with uncompromising design and comforts. Coach house available separately and additional garage parking can be added if acquired, please inquire.

5 Beds ⋅ 7 Baths ⋅ 12639287 MLS

A sophisticated presence, landmark status, architectural integrity, and an unprecedented outdoor footprint for Wicker Park, 1407 N. Hoyne Ave. is a one-of-a-kind opportunity for the homeowner who wants an expansive city estate with pedigree and a modern program. Originally built for beer baron John H. Rapp in 1886, this 8250 SqFt-square-foot, 5 bed/4.3 bath single-family home underwent a multi-year renovation and restoration by Rugo Raff Architects. Preserving elements of its Victorian charm while optimizing sightlines and integrating first-class finishes was paramount. This special home's unheard of 98' x 110' lot affords multiple green spaces, including a deep front yard with mature landscaping, a side yard with raised garden beds and a European-style pergola. Inside, an elegant entry plus an oval-shaped entry hall link to a lovely living room with an abundance of natural light, a traditional turret, and a wood-burning fireplace, and a formal dining room just beyond with hand-scraped walnut floors. The custom chef's kitchen stuns with O'Brien Harris cabinetry, white quartzite countertops, professional-grade Wolf/Sub-Zero appliances, an herb garden, a full butler's pantry, a breakfast dining space with banquette seating, and a built-in desk. The main level also features an intimate family room with built-in walnut cabinetry and a chic beverage center, and two beautiful limestone terraces accessed via French doors: a 12' x 23' west terrace for open-air entertaining and a 12' x 17' side terrace that's perfectly appointed for large-scale alfresco dining with an outdoor kitchen and a built-in grill. A striking example of this home's flawless interior architecture is the centrally located, curving suspended staircase. The second level is devoted to two secondary bedrooms (one with custom bunk beds), the first of two laundry rooms, and an impressively spacious primary suite with a sitting area, a custom dressing room, a walk-in closet, and a marble-clad ensuite bath with two vanities, a soaking tub, and a deluxe shower. The third floor presents two designer offices--a handsome den with knotty alder wood floors and a gas fireplace, a cozy den with a wet bar, an exercise room, and yet another polished guest bedroom. But there's more... This truly magnificent home also comes complete with a fully finished garden level with a massive playroom that opens onto a basement terrace, a wine room, a kitchenette, another large guest bedroom with den perfect for related living, a second laundry room, a walk-in storage room, and a custom mudroom that connects to an attached garage. Additional callout details and amenities include restored original doors and hardware, custom woodwork and trim throughout, designer lighting and wallcoverings throughout, four total fireplaces, 97 Marvin windows, a Lutron lighting system, self-irrigating planters on both terraces, and an excess of custom interior storage. Walking distance to Wicker Park proper and the world-class shopping and dining that extends from the neighborhood's famed Six Corners, 1407 N. Hoyne Ave. is a one-of-a-kind home with uncompromising design and comforts. Coach house available separately and additional garage parking can be added if acquired, please inquire.

1407 N Hoyne Avenue, Chicago