Oakland Real Estate

Welcome to Oakland, Illinois – a charming village that perfectly blends small-town allure with convenient access to urban amenities. Nestled in the heart of Coles County, Oakland is known for its rich history, friendly community, and picturesque landscapes. With a population of just over 1,500 residents, this tight-knit community fosters a warm and inviting atmosphere where neighbors become friends.

One of Oakland's standout features is its commitment to preserving the beauty of its natural surroundings. The village is adorned with lush parks and recreational areas, perfect for families and nature enthusiasts alike. Enjoy leisurely strolls or invigorating jogs on the scenic trails, or gather with loved ones for a picnic in one of the well-maintained parks. The nearby Lake Paradise offers fishing, boating, and serene views, making it a favorite spot for outdoor activities.

For those who appreciate a vibrant community spirit, Oakland hosts various events throughout the year, from seasonal festivals to farmers' markets that showcase local produce and crafts. The local school district is dedicated to providing quality education, ensuring that families can thrive in a nurturing environment.

Conveniently located just a short drive from larger cities like Charleston and Mattoon, Oakland provides easy access to shopping, dining, and entertainment options, while still allowing residents to enjoy the tranquility of rural living. Whether you’re looking for a place to settle down or a community that feels like home, Oakland, Illinois, offers an idyllic setting for all stages of life. Come explore the charm and warmth of Oakland – your new home awaits!

Newest Listings in Oakland

$1,499,000

9 Beds ⋅ 6 Baths ⋅ 12801322 MLS ⋅ NEW Status

New construction 3 unit building, 3 bedroom 2 baths each unit, great option for owner occupy or investment property. Speck sheet under additional information. Individual HVAC systems, Samsung appliances, close foam insulation, insulation between floors, units have balconies and there is finished rooftop on the coach home, kitchens with quartz counter tops, inside back staircase. Amazing location, steps to lakefront parks, bike paths and beaches, Lake shore drive, 5 minutes drive to downtown.

3723 S Lake Park Avenue, Chicago

$2,150,000

12801777 MLS ⋅ NEW Status

Once in a Generation, The Crown Jewel of Oakland set on a botanical campus spanning 70 feet of frontage. If you seek the best, if you have exquisite taste, if you want a one of a kind with an elevator that opens directly into most apartments with grand terraces, you have arrived. Located in an exclusive community alongside million dollar homes & within 1/4 block of Mandrake Park, 5 minute walk to the lakefront at the very north end of Drexel Blvd, with its idyllic fountain & cul-de-sac is a magical whimsical storybook setting offering 5 Massive full-floor units ultra-luxurious 3-4 Bed/2-3 Bath residences set in a made for TV boutique, elegant, Gothic Greystone. Be inspired by the grand, formal lobby with inlaid stone floors, intricate woodwork, stunning modern art, a crystal cut chandelier & super "mod" LED wall sconces. The elevator opens directly into most residences' private foyer, which leads to a massive great room, with soaring ceilings & 7' tall window bays that capture phenomenal sun soaked south & west vistas up & down lush & forested Drexel Boulevard. Gorgeous plank hardwood floors, which contrast with sleek 7" crown & baseboard moldings, 8' tall solid core doors, polished chrome door handles & accessories, a custom designed & built fireplace with glass, stone & quartz mantel + gorgeous lighting with Decora switches & dimmers. Adjacent to the great room, cook, entertain & eat in a true & REAL gourmet kitchen with 1 1/4" thick quartz countertops, a massive work island with bar stool seating, state-of-the-art stainless appliances, a multi burner stove, tunnel exhaust hood, dishwasher, 36" refrigerator with ice & water dispensers, built-in microwave drawer & brilliant porcelain full height backsplashes. Other features include strategically placed cable & electric for flat screen televisions, Hi Efficiency HVAC, high tech LED lighting & many other features. Gracious jaw dropping primary bedroom suite with an infusion of natural light from tall south facing windows, enormous walk-in closet is ready to house a large wardrobe, with custom double hanging SS organizers some which include 20 lineal feet of hanging & 55 lineal feet of shelves. Resort Luxury spa bathroom with heated porcelain tile heated floors, steam shower, quartz bench, a custom designed floor to ceiling glass wall & door system, a rain shower, handheld shower & separate body washes, 6' air bath, a wall mounted floating double bowl vanity & two large mirrored medicine cabinets. Numerous oversized rear terraces offer respite to enjoy cocktails, read a book or have breakfast through dinner, private & spacious with sweeping downtown views. Full Laundry Center complete with full size washer & dryer, countertops & cabinetry cabinets. Enjoy fully curated exotic botanical gardens fully with specimen trees & bushes, many grafted, from around the world, including Japan, various countries in Eastern Europe, Canada & the USA ( all irrigated controlled by app) topped off with 9 car garage (2 of 9 Tandem). Fully stabilized with exceptional longer term tenants, this stunning, unique, trophy property offers a rare hybrid opportunity pairing investment with legacy. Full financials, floorplans, survey, and extensive pictures available. Actual Annual Income $213,045/NOI $141,525 / 6.5CAP Pre Approved buyers only. 48-72 hours' notice to show M-F (no weekend showings)

3967 S Drexel Boulevard, Chicago

$649,900

4 Beds ⋅ 3 Baths ⋅ 12794949 MLS ⋅ NEW Status

Welcome to this beautifully renovated two-flat in Ellis Place, offering an ideal blend of comfortable living and income potential! Set along a picturesque, gated and tree-lined courtyard, this property features a spacious two-story main residence with 3 bedrooms and 2 full baths, plus a separate renovated 1 bedroom, 1 bath garden unit. The main unit offers a thoughtfully updated interior and well-appointed floor plan. The inviting living room features hardwood floors and is anchored by a cozy corner fireplace making it the perfect spot to unwind. Enjoy meals in the eat-in kitchen with refinished cabinetry, granite countertops, center island, stainless steel appliances, pantry and a spacious dinette area. A convenient laundry area completes the main level. Upstairs, retreat at day's end to the comfortable primary suite featuring vaulted ceilings, double closets, a private full bath and its own fireplace! Also on the 2nd level are two additional bedrooms and another full bath. Grill or relax on the private deck overlooking the fully-fenced yard with a firepit and detached 2 car garage. The garden unit provides an excellent opportunity for rental income, related living, or additional flexible space. This building was extensively rehabbed in 2011, along with more recent improvements including a newer furnace (2017), updated back doors, garage door, backyard fencing, LED lighting, window treatments and bay window siding. In addition, each unit has its own private laundry, dedicated hvac and is individually metered. Located in desirable Oakland, this property is across the street from Holly Park (playground/splash pad) and just blocks from Oakwood Beach, shopping, dining, public transportation, schools and more! Don't miss your chance to own this versatile property, ideal for both investors or owner-occupants alike!

4037 S Ellis Avenue, Chicago

$950,000

3 Beds ⋅ 4 Baths ⋅ 12787736 MLS ⋅ ACTIVE Status

Chicago

$950,000

5 Beds ⋅ 4 Baths ⋅ 12793342 MLS ⋅ ACTIVE Status

A rare opportunity to experience elevated city living in Oakland's newest collection of six fee-simple luxury row homes. Designed for those who appreciate architecture, exceptional craftsmanship, and sophisticated modern living, CollectionSIX pairs expansive interiors with thoughtfully curated finishes and remarkable outdoor space. Spanning three beautifully appointed levels and crowned by a massive 1,000-square-foot private roof deck, each residence offers an extraordinary sense of scale, light, and privacy. Lofty ceilings, clean architectural lines, generously proportioned bedrooms, exceptional closet and storage space, and private yards create a sophisticated living experience that is as functional and comfortable as it is impressive. At the heart of the home is a spectacular chef's kitchen featuring custom cabinetry, oversized quartz countertops, and premium appliances, including a Dacor 36-inch range and Dacor refrigerator. The elegant semi-open floor plan seamlessly connects the kitchen to expansive, light-filled living and dining spaces, creating an ideal setting for both everyday living and entertaining while still maintaining a sense of privacy. The luxurious primary suite is a true retreat, offering ample space for a king-sized bed, generous closets, and a spa-inspired en-suite bath featuring a walk-in wet room, curbless shower, and double vanity. The second level also includes two additional bedrooms, a full bath, and a beautifully appointed laundry room with side-by-side washer and dryer, cabinetry, and a utility sink. The fully finished lower level expands the possibilities with a light-filled recreation room, wet bar, beverage cooler, custom cabinetry and shelving, two additional bedrooms, a guest bath, and an exceptionally large storage room-offering the flexibility today's lifestyle demands. And then there is the showstopping rooftop deck. Designed for unforgettable entertaining and effortless outdoor living, this private rooftop retreat features water, electric, and gas connections, along with a convenient indoor wet bar. Imagine summer dinners, evening cocktails, skyline views, and gatherings with friends-all from the comfort of home. Ideally positioned in sought-after Oakland, CollectionSIX places you moments from the proposed Bronzeville Trail, lakefront, 39th and 41st Street beaches, neighborhood dining, and some of the best of Chicago's South Side. Enjoy easy access to Lake Shore Drive, I-90/94, I-55, and convenient CTA bus and train routes. Downtown Chicago, the South Loop, Hyde Park, the University of Chicago, Museum Campus, and the Griffin Museum of Science and Industry are all within easy reach. A Collection SIX home is more than a residence-it is a sophisticated urban sanctuary where every detail tells a story of quality, comfort, and intention. Discover your oasis in the city at CollectionSIX.

1012 E 41St Street, Chicago

$1,100,000

5 Beds ⋅ 4 Baths ⋅ 12774843 MLS ⋅ ACTIVE Status

A rare opportunity to experience elevated city living in Oakland's newest collection of six fee-simple luxury row homes. Designed for those who appreciate architecture, exceptional craftsmanship, and sophisticated modern living, Collection SIX pairs expansive interiors with thoughtfully curated finishes and remarkable outdoor spaces. Spanning three beautifully appointed levels and crowned by a massive 1,000-square-foot private roof deck, each residence offers an extraordinary sense of scale, light, and privacy. Lofty ceilings, clean architectural lines, generously proportioned bedrooms, exceptional closet and storage space, and private yards create a sophisticated living experience that is as functional and comfortable as it is impressive. At the heart of the home is a spectacular chef's kitchen featuring custom cabinetry, oversized quartz countertops, and a premium appliance package, including a Dacor 36-inch range and a Dacor refrigerator. The elegant semi-open floor plan seamlessly connects the kitchen to expansive, light-filled living and dining spaces, creating an ideal setting for both everyday living and entertaining while still maintaining a sense of privacy. The luxurious primary suite is a true retreat, offering ample space for a king-sized bed, generous closets, and a spa-inspired en-suite bath featuring a walk-in wet room, curbless shower, and double vanity. The second level also includes two additional bedrooms, a full bath, and a beautifully appointed laundry room with side-by-side washer and dryer, cabinetry, and a utility sink. The fully finished lower level expands the possibilities with a light-filled recreation room, wet bar, beverage cooler, custom cabinetry and shelving, two additional bedrooms, a guest bath, and an exceptionally large storage room-offering the flexibility today's lifestyle demands. And then there is the showstopping rooftop deck. Designed for unforgettable entertaining and effortless outdoor living, this private rooftop retreat features water, electric, and gas connections, along with a convenient indoor wet bar. Imagine summer dinners, evening cocktails, skyline views, and gatherings with friends-all from the comfort of home. Ideally positioned in sought-after Oakland, Collection SIX places you moments from the lakefront, 39th and 41st Street beaches, neighborhood dining, and some of the best of Chicago's South Side. Enjoy easy access to Lake Shore Drive, I-90/94, I-55, and convenient CTA bus and train routes. Downtown Chicago, the South Loop, Hyde Park, the University of Chicago, Museum Campus, and the Griffin Museum of Science and Industry are all within easy reach. A Collection SIX home is more than a residence-it is a sophisticated urban sanctuary where every detail tells a story of quality, comfort, and intention. Discover your oasis in the city at Collection SIX

1006 E 41St Street, Chicago

$269,999

12785878 MLS ⋅ ACTIVE Status

Exceptional investment opportunity in Chicago's Oakland neighborhood! This generously sized vacant lot offers an attractive advantage with its wider-than-typical frontage, providing added flexibility and potential for future residential development. Ideally situated in a well-established community experiencing ongoing development and revitalization, the property offers convenient access to downtown Chicago, Lake Shore Drive, public transportation, shopping, dining, and other city amenities. An excellent opportunity for builders, developers, and investors seeking a strategically located parcel with promising development potential. Bring your vision to life and explore the possibilities this unique property has to offer!

3612 S Lake Park Avenue, Chicago

4105 S Drexel Boulevard Unit #1SR, Chicago

$344,900

3 Beds ⋅ 3 Baths ⋅ 12685324 MLS ⋅ ACTIVE Status

Welcome to this marvelous over-sized duplex condo in the picturesque sought after neighborhood of historic Bronzeville. Featuring 3 bedrooms and 3 full bathrooms, this beautifully updated duplex offers an abundance of space that is drenched with natural light. The gleaming luxury hardwood floors welcome you in the spacious living room with a grandiose patio door that offers wonderful views of the beautiful tree lined streets. The living room guides you into the spectacular kitchen with amazing high end cabinets, elegant quartz countertops that boast a breakfast bar and stainless steel appliances. The living room offers a serene setting that features a breathtaking fireplace. The main floor also offers a conveniently located full bathroom and a guest bedroom, perfect for when entertaining family and friends. The lower level features two expansive master bedrooms with new carpet, new light fixtures, large walk-in closets and full master baths. The unit also offers plenty of storage space throughout and in-unit laundry room. Enjoy some fresh air on those spring and summer days on your own private balcony. Updates include: New paint throughout, new light fixtures, refinished hardwood floors, new carpet, new kitchen faucet, and new cabinet pulls. The unit includes 1 parking space conveniently located steps away from the backdoor entrance, intercom system, and a private storage locker. Walking distance to the beautiful Oakwood Beach. The proximity to golfing, parks, shopping and dining is outstanding. Pets are welcome.

4105 S Drexel Boulevard Unit #1SR, Chicago

$19,500

12393102 MLS ⋅ ACTIVE Status

Great opportunity! Improved residential lot in Waukegan with water available. Convenient location with great building potential. Buyer to verify utilities and building requirements.

1005 N Lewis Avenue, Waukegan

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Oakland Real Estate

Newest Listings in Oakland

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