South Shore Real Estate

South Shore Real Estate

Welcome to South Shore, a hidden gem nestled along the picturesque shores of Lake Michigan in the vibrant city of Chicago, Illinois. This charming neighborhood is a harmonious blend of rich history, cultural diversity, and community spirit, making it an ideal place to call home.

South Shore boasts a variety of architectural styles, from vintage bungalows to modern condos, reflecting its storied past and the evolution of the community. The tree-lined streets are perfect for leisurely strolls, while the local parks, including the expansive South Shore Cultural Center, offer beautiful landscapes and recreational activities for all ages. Here, you can enjoy a sunny day at the beach, engage in outdoor sports, or simply relax and soak in the stunning views of the lake.

The neighborhood is known for its vibrant cultural scene, with art galleries, theaters, and music venues that celebrate the rich heritage of its residents. South Shore is also home to a variety of dining options, ranging from cozy cafes to exquisite restaurants, serving up an array of culinary delights that reflect the neighborhood's diverse population.

Education is a cornerstone of the community, with several well-respected schools and educational programs available for families. The strong sense of community is palpable, with local events and festivals bringing residents together to celebrate their unique culture and foster connections.

Whether you're seeking a tranquil retreat or an active lifestyle, South Shore offers a welcoming environment that truly feels like home. Discover the warmth and charm of this remarkable neighborhood, where every street tells a story and every resident is part of a larger tapestry. Welcome to South Shore!

Newest Listings in South Shore

$4,375,000
3 Beds ⋅ 4 Baths ⋅ 2557653 MLS ⋅ ACTIVE Status
What story could you write here? Set along 83 feet of South Shore waterfront, this is the kind of Lake Chelan home where mornings begin with coffee while watching the sunrise and evenings wind down watching it set over the mountains. This waterfront view is simply stunning. Summer days are spent boating & floating just minutes from downtown Chelan. With a floorplan designed for the way Lake Chelan is meant to be enjoyed, accordion-style window-walls open the home to expansive lake views while the completely remodeled kitchen, great room and outdoor living spaces become the backdrop for holiday weekends, spontaneous getaways and unforgettable summers. With 3 bedrooms, a main-level primary suite, loft, office with Murphy bed (4th BR), game room and detached 1-bedroom ADU, there's room for everyone who wants to stay just one more day. Outside, enjoy your covered deck with heaters & speakers, wet-bar area, large lawn area with room for a future pool, private dock with boat lift, buoys, newer bulkhead and steps into the lake. The oversized 1,120 sq. ft. garage accommodates up to 5 vehicles with 400-amp power and EV capability. Main home: 3,211 sq. ft. ADU: 720 sq. ft. Total Garage Square ft appx 1900 sq. ft. Upper Garage is Climate controlled. The home can be your canvas for thousands of memories yet to be made and enjoyed. A few photos are virtually staged.

21 Grace Lane, Chelan

Listing courtesy of Coldwell Banker Danforth.

$1,599,000
2 Beds ⋅ 3 Baths ⋅ 2555165 MLS ⋅ ACTIVE Status
Custom-built and meticulously maintained by its original owner, this exceptional single-level rambler sits on 2.5 private acres with panoramic Lake Chelan and mountain views from nearly every room. Offering 2,652 sq ft, the open floor plan showcases quality craftsmanship, soaring ceilings, exposed wood beams, expansive windows, radiant heated concrete floors throughout—including the garage—a DaVinci linear fireplace, and in-wall surround sound. The chef's kitchen features Huntwood cabinetry, granite countertops, a propane DCS cooktop, double ovens, Thermador refrigerator, Sub-Zero freezer drawers, Miele espresso machine, wine refrigerator, built-in ice maker, and an oversized island. The spacious primary suite offers 11-foot ceilings, patio access, dual closets, and a spa-inspired bath with a multi-head walk-in shower. Outside, enjoy level irrigated acreage, privacy, sweeping lake views, a BBQ hookup, jetted hot tub, and RV parking with electrical hookups. The impressive 2,880 sq ft insulated shop includes oversized 12' x 16' doors, radiant heat, bathroom, washer/dryer, 220 power, air compressors, 30-amp hookups, and a spacious pass-through driveway, providing exceptional space for RVs, boats, equipment, hobbies, or storage. A rare opportunity to own a high-end custom home offering sprawling one-level living, expansive views, outstanding shop space, and privacy just minutes from Lake Chelan. Furniture negotiable.

206 Mountain Lake Lane, Chelan

Listing courtesy of Windermere RE/Lk Chelan Dwntwn.

$1,250,000
3 Beds ⋅ 4 Baths ⋅ 2545363 MLS ⋅ ACTIVE Status ⋅ Chelan Ridge Div 2 BLDG.
Experience luxury Lake Chelan living with ultimate privacy and breathtaking 180 degree lake and mountain views including Slide Ridge, Wapato Point peninsula, and a spectacular front-row seat for annual 4th of July fireworks. Designed for multi-generational living, rental potential, or an exceptional private retreat, this custom home features full kitchens and utility rooms on both levels, separate lower-level entry, and flexible living spaces. Community waterfront and boat dock access! Main level showcases vaulted wood ceilings, rich hardwood floors, granite countertops, walk-in pantry and a stunning stone fireplace. The luxurious primary suite offers a spa-inspired bath with jetted soaking tub, dual-sided fireplace, granite shower, and dual vanities. Lower level features a 2nd primary suite with oversized bath featuring a dedicated room wired for a future sauna, second stone fireplace, bonus room ideal for additional media, bed, office, or fitness space. Built to last with Milgard windows and hardy solid wood doors. Enjoy expansive lake-view decks, private hot tub, and ample room to add a pool. Wine enthusiasts will appreciate a wine room featuring rare antique ironwood doors. Garage provides ample storage and third kitchen area, while full RV hookup adds flexibility for recreation. Every detail was designed to maximize comfort, functionality, and unforgettable Lake Chelan views creating an extraordinary opportunity for a luxury primary residence, second home, or investment.

7371 Ridgeview Drive, Chelan

Listing courtesy of Windermere RE/Lake Chelan.

$1,199,000
4 Beds ⋅ 3 Baths ⋅ 2541921 MLS ⋅ ACTIVE Status
RARE SHORT-TERM VACATION RENTAL PERMIT INCLUDED IN THE SALE CAN BE TRANSFERRED ONLY UNTIL SEPTEMBER 16th 2026 FOR PASSIVE INCOME. Furnished/decorated turnkey beautiful Lake Chelan destination getaway retreat. Welcome to The Vineyards Lodge. Panoramic lake and mountain views from your private covered deck and backyard of your dream sanctuary. Beautiful custom Northwest craftsman home with custom millwork throughout. 4-bedroom, 3-bath home located in private neighborhood of only three homes. Surrounded by wineries and restaurants. Fully furnished and decorated—down to the plates, wine glasses, and silverware. Smart TVs, whole-house speaker system. Modern kitchen, gas fireplace, jetted tub, Vichy shower in primary bathroom, hidden sleeper in living room, sectional couch, and cozy TV seating area in the loft. Oversized two-car garage with extra-tall garage doors to fit a boat or larger vehicle. Brand-new high-efficiency, high-output air conditioner/heat pump ducted system. Home has plenty of room for guests and can sleep 10+ people comfortably. Close proximity to downtown Chelan. This rare opportunity gives you the option to rent the property as a vacation rental as much or as little as you want when not using it. This home has produced a healthy passive income for its current owners. Seize the opportunity to own this rare find. Open the door to your own fully furnished and decorated Lake Chelan relaxing getaway retreat. Turnkey and ready to move in without the hassle.

915 S Lakeshore Road, Chelan

Listing courtesy of Nick McLean Real Estate Group.

$700,000
3 Beds ⋅ 2 Baths ⋅ 2530560 MLS ⋅ ACTIVE Status
Light-filled spaces and a peaceful atmosphere make this home the perfect waterfront retreat. Just steps from the neighborhood beach, or walk down to your own private shoreline with 120 feet of waterfront. Launch a kayak directly from the deck and explore the estuary or venture out into the Sound, where Orcas, Eagles, Seals, and Sea Otters are regularly spotted. Stay connected with super fast fiber optic service. Oversized, heated 2 car garage/shop with EV Charger, additional secure storage and plenty of extra outside parking for RV/Boat/Toys! Currently operating as a successful short-term rental, the property already has over $6,000 in booked revenue reserved for June and July. Continue using it as an income-producing STR or enjoy it as your own fully furnished waterfront getaway. The sale includes two separate tax parcels. The primary parcel, 61 E Orchard Beach Dr, includes the home. The second parcel, 51 E Orchard Beach Dr, offers potential for future development or the opportunity to enjoy additional privacy and space.

61 E Orchard Beach Drive, Grapeview

Listing courtesy of COMPASS.

$715,000
1 Beds ⋅ 1 Baths ⋅ 2529164 MLS ⋅ ACTIVE Status ⋅ First Creek BLDG.
Nestled on 16+ acres of beautifully maintained timbered forest, “Bear Hollow” offers the ultimate private mountain retreat with a completely renovated real log cabin crafted from logs harvested directly from the land! Cabin has been completely remodeled with an entirely new foundation, complete log restoration and protection, new windows, new roof (2025), new decks and railings, and a circular gravel driveway, every detail has been thoughtfully executed. Inside, the fully remodeled cabin showcases stunning custom craftsmanship and finish work throughout, including custom cabinetry, updated appliances, new wood stove, expanded family room addition, and all new electrical, plumbing, and mechanical systems. The organized mechanical room is conveniently accessed through an exterior cellar door. High-speed Starlink internet provides modern convenience in this peaceful setting. Furnishings, furniture, and décor are negotiable for a turnkey opportunity. Adding to the charm and versatility, the property also includes a functional yurt, original small log cabin, metal shop with office and carport, private well, and borders a creek that enhances the truly storybook atmosphere. Immaculate, timeless, and impossible to replicate, Bear Hollow is a rare legacy property blending rustic charm with exceptional quality and comfort.

2350 First Creek Road, Chelan

Listing courtesy of Windermere RE/Lk Chelan Dwntwn.

$1,295,000
3 Beds ⋅ 3 Baths ⋅ 2526407 MLS ⋅ ACTIVE Status
Experience the best of Lake Chelan living along the coveted “Golden Mile” at Southshore Estates, a gated waterfront community of just six homes. This beautifully updated 2,040 sq ft home offers 3 bedrooms, 2.5 baths, sweeping lake views from nearly every room, an extra-deep 1-car garage, and ample driveway parking for guests, boats, or additional vehicles. Enjoy effortless indoor-outdoor living with expansive gathering spaces, no-maintenance hard-scaping, and stunning views that capture the beauty of the lake year-round. Community waterfront amenities include the recently refinished dock with a dedicated private boat lift, boat launch, and the shared waterfront area—delivering the waterfront lifestyle without the burden of waterfront taxes. Recent upgrades include a new HVAC system and heat pump, new water heater, LVP flooring throughout, fresh interior paint, updated trim, and all new door hardware. Perfectly situated just minutes from some of Lake Chelan’s most renowned wineries and only 10 minutes from downtown Chelan, this home offers an ideal blend of privacy, recreation, and convenience in one of the area’s most sought-after locations.

1496 S Lakeshore Road, Chelan

Listing courtesy of Windermere RE/Lake Chelan.

$299,000
1 Beds ⋅ 1 Baths ⋅ 2526315 MLS ⋅ ACTIVE Status
Escape the noise and rediscover what matters. Perched high above Lake Chelan on 20.02 private acres, this off-grid mountain retreat delivers panoramic lake and mountain views that are nothing short of breathtaking. Surrounded by towering evergreens and abundant wildlife, the setting offers unmatched peace, privacy, and a true connection to nature. The 988 sq. ft. cabin features one spacious bedroom (with potential to create a second), one bath, a full kitchen, cozy wood stove, solar power, propane, and a backup generator, providing comfortable self-sufficient living year-round. Whether you're searching for a weekend getaway, hunting cabin, recreational basecamp, vacation retreat, homestead, or a place to unplug from everyday life, this property offers exceptional flexibility. Located just 1.2 miles above Lake Chelan State Park and the public boat launch, you'll enjoy quick access to boating, fishing, hiking, and endless outdoor recreation while still feeling worlds away. Convenient access from South Lakeshore Road and Navarre Coulee Road makes travel to Chelan, Wenatchee, and Seattle surprisingly accessible. This is an incredible opportunity to own 20 acres with spectacular Lake Chelan views at a price point that's becoming increasingly difficult to find and seller financing is offered! The primitive road is well maintained but best for AWD vehicles.

109 Granit Falls Road, Chelan

Listing courtesy of KW NCW.

$335,000
2524891 MLS ⋅ ACTIVE Status ⋅ Chelan Rdg Div 2 BLDG.
Rare opportunity in Chelan Ridge on the desirable south shore of Lake Chelan! This view lot offers stunning unobstructed lake views both up-lake and down-lake, with no possibility of future homes blocking your sightlines. Private boat slip #10 at the Chelan Ridge Marina included in the sale, ideally located in the protected center section of the newer marina. The lot is well suited for a daylight basement design and features scattered pines, wide paved access roads, water and power available, and septic needed. Geotech study completed in 2011 and site evaluation completed in 2021. Existing conceptual house plans available. Conveniently located near Lake Chelan State Park with boat launch, play areas, and walking trails, plus quick access to Navarre Coulee Rd for an easy drive to Wenatchee or the west side of the mountains. Approximately 15 minutes from downtown Chelan. Boat slip alone is valued around $75,000 making this property an exceptional value!

7376 Ridgeview Drive, Chelan

Listing courtesy of Windermere RE/Lk Chelan Dwntwn.

$1,349,000
3 Beds ⋅ 3 Baths ⋅ 2523960 MLS ⋅ ACTIVE Status ⋅ Grandview Village BLDG.
One of the most breathtaking, dramatic & expansive views of Lake Chelan! This beautifully cared for modern, open-concept home is an entertainer’s dream, with views from nearly every room! The home boasts an open-air game room/office, a spacious vaulted great room with walls of windows, covered deck w/ outdoor speakers + gas BBQ hookup, a large covered front porch & lower patio for multi-season outdoor entertaining! The lovely primary ensuite has a spacious walk-in w/ closet organizers. The lower level features an extra large rec-room w/ plush carpet, two additional lake-view bedrooms, full bath & large storage rm w/ a second washer/dryer hookup. 3rd car garage bay has been finished as a ping-pong room if desired. This excellent Southshore location, only 8 min from town, is surrounded by vineyards, & within walking distance to multiple wineries. Direct access from the yard to 3 miles of paved trails through vineyards! Newer rockeries and easy-care landscaping has been added to make this a lower-maintenance yard, w/ a level lawn area perfect for a future swimming pool. With laundry on the main floor & ample storage, single-level living is easy, while still having plenty of room for friends & guests! Best kept secret: Southshore homes offer a delightful escape from summer heat. Enjoy all that Chelan has to offer: great weather, water sports, golf, hiking, award-winning wineries, outdoor concerts, water park, surf pool, and so much more. Begin making memories this summer!

191 Grandview Lane, Chelan

Listing courtesy of Coldwell Banker Danforth.

$205,000
2522712 MLS ⋅ ACTIVE Status ⋅ Replat of Sunnybank Addition BLDG.
Welcome to Lakeview Place at Sunnybank! A charming neighborhood on the South Shore of Lake Chelan. A stone's throw away from wineries & a short 7-mile drive to downtown Chelan. This well-established community offers the perfect blend of serenity & convenience. Nestled amongst the pines on over a 1/4 acre property, this parcel boasts a picturesque setting w/ peekaboo views of Lake Chelan. Enjoy private access to the lake, a lakeside park area, swimming hole, & day-use marina (no slip included). Level lot /w gentle rolling lends versatility for lots home styles & offers easy paved access. Recent survey completed, water & power in road, perc test completed 2020. Don't miss this opportunity to build your dream home in a sought after location. Boat slip currently available for purchase though Sunnybank HOA!

Lakeview Place, Chelan

Listing courtesy of CB Cascade RE - Wenatchee.

$299,000
2522558 MLS ⋅ ACTIVE Status ⋅ Maritas Vineyard Estates BLDG.
Spacious 1/3 acre parcel located in the gated and highly sought after community of Maritas Vineyard Estates. This homesite offers some of the best panoramic Lake Chelan and mountain views on the east side of the development. Ready to build with grading complete and site preparation already done. Architecturally designed home plans are available with the sale, making it easy to bring your vision to life. Utilities are already in place including water, power, sewer, irrigation, and fiber internet. CCRs ensure quality construction throughout the neighborhood. Enjoy a private and quiet community maintained street just minutes from Lake Chelan recreation and the conveniences of town. Spend your summers boating, jet skiing, paddleboarding, kayaking, swimming, or fishing on the crystal clear waters of Lake Chelan. Explore local beaches, waterfront parks, and the popular Slidewaters water park, a favorite destination for all ages. Enjoy lakeside dining, boutique shopping, live music, golf courses, hiking trails, and year round outdoor recreation. The area is also known for its award winning wineries and cider houses, offering unforgettable tasting experiences with breathtaking vineyard and lake views. Conveniently located near Highway 97 and close to renowned wineries including Siren Song, Nefarious, Fielding Hills, Karma, and many more.

115 Loretta Lane, Chelan

Listing courtesy of Nick McLean Real Estate Group.

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Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.


The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.