Leland MI Historical Real Estate, Homes for Sale

4 Beds ⋅ 3 Baths ⋅ 1947750 MLS ⋅ Village Of Leland BLDG.

Originally built in 1900 as the Lutheran Church parsonage, this distinctive historic home offers timeless character in an exceptional location just three blocks from the heart of Leland and three blocks from Lake Michigan access at North Street. Original hardwood floors, unpainted vintage trim, and retro appliances preserve the home’s authentic vintage charm. Set on 3 platted lots, the property includes one of the largest contiguous parcels in the central village. For the past ten years, the home has operated as a vacation rental, offering added appeal for buyers seeking income potential or a seasonal retreat. Located just a few blocks from the Leland Country Club and North Lake Leelanau public access, this property combines historic character, walkable village convenience, and proximity to the area’s most desirable amenities.

201 N Second Street, Leland

$5,250,000

6 Beds ⋅ 4 Baths ⋅ 1947196 MLS ⋅ N/A BLDG.

Enjoy the best of North Lake Leelanau living with 200 feet of private frontage and breathtaking lake views from this spacious 6-bedroom, 3.5-bath home. Designed for gathering family and friends, the home features warm pine kitchen cabinetry, charming tongue-and-groove pine walls and ceilings, a cozy gas fireplace, and custom built-in cabinetry that adds character and functionality throughout. The expansive lakeside deck provides the perfect setting for outdoor entertaining, relaxing, and taking in the beauty of the lake. With six bedrooms, there's plenty of space for hosting guests or creating a year-round retreat. Property improvements include two detached garages offering exceptional storage for vehicles, boats, and recreational equipment, one measuring 1,264 sq ft and the second 576 sq ft. An added bonus is the included 4.2-acre parcel located across the road, providing additional privacy. Point of Sale inspection has been ordered.

5254 N Manitou Trail, Leland

$1,665,000

3 Beds ⋅ 3 Baths ⋅ 1946843 MLS ⋅ Lakeview Highlands BLDG.

Welcome to Sans Souci - an impeccably maintained 3-bedroom, 2.5-bathroom home with approximately 500' of shared Lake Michigan frontage located on a quiet street in the heart of Leland Village. The house sits on three lots offering exceptional space and privacy. Inside, the home features warm hardwood floors, an open-concept layout, and a striking natural stone fireplace that anchors the main living space. A bright sunroom offers the perfect place to unwind, with peaceful views of the beautifully landscaped, low-maintenance yard. The kitchen and dining areas flow seamlessly together, ideal for entertaining or everyday comfort. Enjoy main floor living with three generously sized bedrooms including a tranquil primary suite with en suite bath. Downstairs the partially finished lower level offers bonus living space and a temperature-controlled wine cellar — a rare and refined touch.

116 W Hill Street, Leland

$895,000

3 Beds ⋅ 2 Baths ⋅ 1946269 MLS ⋅ Village Of Leland BLDG.

You just can't get any closer to the center of Leland. The historic home at 203 South Main St is composed of 3 buildings joined together into one house. The front two rooms on two floors are the oldest, built in the 1850s, making it one of the oldest buildings in Leland. By the mid-1860s, the oldest portion served as offices for the Leland & Lake Superior Iron Company. Sometime after the iron company went bankrupt in 1884, the building was used as a private home and was expanded by joining two existing buildings to it. Before 1900, the home was occupied by Mary Possing Prause (b 1856 - d 1959), who operated it as a rooming house, The Garden Inn, named for Mary’s extensive and renowned gardens. During this time, the first indoor bathroom in Leland was installed, paid for by a wealthy guest who refused to use the outhouse during his lengthy stay while having a grand beach house built nearby. The home remained in the family until it was purchased in 1987 by the current owner, who completely renovated and restored it. Recent Improvements During the past 3 years, the roof, the well, gas furnace, hot water heater, and refrigerator have been replaced.

203 S Main Street, Leland

$3,000,000

3 Beds ⋅ 2 Baths ⋅ 1945617 MLS ⋅ Chandler's Park Addition BLDG.

A rare opportunity in downtown Leland - one of the last buildable riverfront properties on the Leland River! 0.99 acres with 214 feet of private river frontage. The existing home and garage can be remodeled to restore its history and charm or removed to make way for your custom estate on this significant, estate-sized lot along one of Northern Michigan’s premier waterways. Boat directly to North Lake Leelanau and enjoy immediate access to all the shops, dining and summer life of Main Street, plus a short walk to the beach. The home has an existing well and municipal sewer. Continue the current use as residential lots or utilize the commercial zoning for your future business endeavors. This is a once in a lifetime opportunity to build your Leland dream estate or to develop it.

204 S Chandler Street, Leland

$1,595,000

4 Beds ⋅ 3 Baths ⋅ 1945171 MLS ⋅ Village Of Leland BLDG.

Originally built in 1900 as the Lutheran Church parsonage, this distinctive historic home offers timeless character in an exceptional location just three blocks from the heart of Leland and three blocks from Lake Michigan access at North Street. Original hardwood floors, unpainted vintage trim, and retro appliances preserve the home’s authentic vintage charm. Set on 4 1/2 platted lots, the property includes one of the largest contiguous parcels in the central village. For the past ten years, the home has operated as a vacation rental, offering added appeal for buyers seeking income potential or a seasonal retreat. Located just a few blocks from the Leland Country Club and North Lake Leelanau public access, this property combines historic character, walkable village convenience, and proximity to the area’s most desirable amenities.

201 N Second Street, Leland

$1,350,000

4 Beds ⋅ 2 Baths ⋅ 1944762 MLS ⋅ N/A BLDG.

Charming village living in the heart of Leland! This well-maintained 4-bedroom, 1.75-bath home is ideally situated on two spacious village lots, offering both privacy and room to enjoy the outdoors. Inside, you’ll find warm hardwood floors throughout much of the home and a cozy gas fireplace that anchors the inviting living space. The bright four-season porch provides the perfect spot to relax and take in the peaceful surroundings. Additional features include underground irrigation to keep the expansive yard looking its best, and a convenient 1-car attached garage. With its prime location close to Leland’s shops, dining, and waterfront, this property offers the perfect blend of comfort, space, and village charm. This property includes two platted village lots, the house sits on the east lot.

205 N Second Street, Leland

$1,105,000

3 Beds ⋅ 2 Baths ⋅ 1936210 MLS ⋅ Na BLDG.

Fabulous, vintage, and in the heart of walkable Leland! Affectionately named Pearl Haven, this delightful village residence has the charm of an early Leland homestead, plus many contemporary updates. Tucked into the hillside and hidden beneath the branches of mature maple trees, this home is a private oasis near to Leland School and the excitement of downtown. Step through the front gate and into the shade! Here you’ll find a beautiful screened-in porch with mahogany decking, bead-board ceiling, and a front porch swing – a lovely place to escape the summer heat. Inside, the main living area is a generous open plan. The living room and dining room flow together through French doors to a secluded patio and a low-maintenance backyard. A private den with beautiful built-in shelves is located off the main living space and is a quiet hideaway for reading or working (when you must). No need for a den? Transform this room into an easy, main floor guestroom. The kitchen is cozy, yet luxurious enough to include a mini butler’s pantry and space for quick meals. The main floor primary bedroom is a beautiful place to unwind – lofted ceilings elevate this room, while a custom stained-glass window, built in desk area, and walk-in closet with laundry add both character and functionality to the space. When guests and family come to visit, send the kids upstairs! The second level is made for sleepovers, euchre tournaments, and movie nights! Here, two bedrooms anchor opposite ends of the floorplan and are connected by a large, carpeted family room. Dormers add light and air to this space, while built-in bookshelves make for a pleasant reading area on rainy days. A second laundry room and full bathroom with claw-foot tub round out this fabulous upstairs. In all, this vintage gem is pure Leland inside and out. Spend your summers here, welcome short term rental guests, or bring your family and live in Leland full-time. Enjoy the best of village life, whatever you choose!

220 E Pearl Street, Leland

$400,000

3 Beds ⋅ 3 Baths ⋅ 1935972 MLS ⋅ Nont BLDG.

Opportunity knocks just five minutes from charming Leland and historic Fishtown! Nestled on over an acre of peaceful, wooded land, this diamond-in-the-rough offers endless potential. With solid bones and a functional layout, this fixer-upper is ready for your vision and personal touch. Whether you're an investor seeking your next project or a do-it-yourselfer ready to build equity, this property is your blank canvas. Enjoy the privacy and natural beauty of the setting while being just a short drive from beaches, wineries, shops, and restaurants. Bring your ideas and make this your Northern Michigan retreat!

5457 N Manitou Trail, Leland

$935,000

5 Beds ⋅ 3 Baths ⋅ 1932882 MLS ⋅ N/A BLDG.

Welcome to this beautifully remodeled 5-bedroom, 2.75-bath home nestled on a 0.25-acre lot in desirable Leland Village. Every inch of this home has been thoughtfully updated, featuring luxury vinyl plank flooring throughout the main living spaces, stunning soapstone countertops, and a cozy gas fireplace that anchors the open-concept living and dining area. This home offers both comfort and versatility with two dedicated bunk rooms (which are 2 of the bedrooms)—perfect for guests or growing families. The modern design blends effortlessly with the laid-back charm of the area, creating the perfect up-north escape or year-round residence. Enjoy a prime location within walking distance to the Leland Country Club, and just minutes from the shops and restaurants and historic Fishtown. With public access nearby to both Lake Michigan and North Lake Leelanau, outdoor adventures are always within reach. Don’t miss your chance to own a piece of Leelanau County! Great layout for a short term rental too.

305 S Fifth Street, Leland

$800,000

2 Beds ⋅ 1 Baths ⋅ 1932451 MLS ⋅ N/A BLDG.

This 2-bedroom, 1-bathroom home is ideally situated just a short walk from the pristine shores of Lake Michigan, offering the perfect blend of in-town living and potential for personalization. While the home is in need of some updates, it presents an excellent opportunity to create your dream retreat in a highly sought-after location. The property includes 3.5 platted village lots, a detached garage, and another building that once was additional living space.

603 S Main Street, Leland

$2,788,000

4 Beds ⋅ 5 Baths ⋅ 1932428 MLS ⋅ Leland Woods BLDG.

Inspired, retreat tucked away on a private 0.47-acre setting with 125 feet of pristine Lake Michigan frontage, this exceptional 4-bedroom, 5-bathroom home offers 3,761 square feet of artfully designed living space. A private drive welcomes you to this peaceful oasis, where nature and architecture harmonize beautifully. Designed by Glenn Arai, the home reflects his Japanese heritage through a thoughtful use of space—featuring intimate areas on split levels, connected by a few gentle steps. This layered design creates a dynamic living experience, with multiple vantage points that seamlessly connect the interior to the stunning natural surroundings. The result is an inviting, interesting environment filled with warmth and light. Inside, the island kitchen serves as a central gathering spot, flowing into a formal dining room perfect for entertaining. Enjoy the comfort of in-floor in kitchen, dining and family room. Generous windows frame views and invite the outdoors in. The spacious layout includes four well-appointed bedrooms, each offering comfort and privacy, and five bathrooms designed with elegance and functionality in mind. Additional features include a 2-car garage and a beautifully landscaped outdoor area ideal for relaxation or hosting guests. Whether you're enjoying the lake breeze from your private shoreline or relaxing in one of the many cozy nooks throughout the home, this property offers a rare blend of serenity, sophistication, and architectural artistry. Fourth bedroom in lower level does not have a privacy door. A portion of the path to the water is on the neighbors property.

5593 N Leland Woods Drive, Leland

$1,525,000

1931931 MLS ⋅ N/A BLDG.

Unique opportunity to own on the river! Prime 0.33 acre redevelopment property with almost 50' of river frontage in Downtown Leland. The L-shaped lot is well suited for residential redevelopment, and includes approximately 178' of frontage on S Main St/M-22. The existing building features approximately 6,875 SF of mixed-use space, including a restaurant/cafe up-front, office space in the middle, and a residential townhome on the river, which is currently being used as a short-term rental unit. With commercial zoning and existing income from leases, this property provides plenty of flexibility to a new owner. Don't miss this rare opportunity to own in Downtown Leland!

407 S Main Street, Leland

$1,240,000

5 Beds ⋅ 3 Baths ⋅ 1927298 MLS ⋅ Metes & Bounds BLDG.

****Charming Cottage with Stunning Lake Michigan Views, 160 FT of Private frontage on Lake Michigan and 195 feet of shared frontage on Lake Leelanau*** This rare find is a classic property built in 1954, offering a perfect blend of timeless charm and modern potential. Nestled between Lake Michigan and Lake Leelanau situated on a 1.09-acre lot with breathtaking views from a bluff, this 5-bedroom, 3-bathroom residence and includes 160 feet of private frontage on Lake Michigan and Shared frontage on North Lake Leelanau with the opportunity for boating, fishing, water sports and to dock a boat. The property’s prime location offers a peaceful, rural setting with easy access to urban amenities. Just a short drive away, the charming Village of Leland offers dining, shopping, and recreational options. Enjoy the vibrant local culture, waterfront living with easy access to Northern Michigan's best.

5273 E Sugarbush Lane, Leland

$1,755,000

5 Beds ⋅ 3 Baths ⋅ 1926282 MLS ⋅ Metes & Bounds BLDG.

Do you love the idea of breathtaking views of eagles, freighters, the Chicago to Mackinac race, and rock hunting on your private Great Lake beach but also want the fun of boating on an inland lake? Here you can do both as this spectacular home is complete with 240 feet of private sandy Lake Michigan frontage and 180 feet of privately shared frontage on North Lake Leelanau. Stroll the sandy beach along the “big” lake or take advantage of the private association’s dock on Lake Leelanau with boat slip availability where you can swim, sun, sail, kayak, motor or paddle to your heart’s content! Also shared through association membership is acreage in which to enjoy walks, croquet, or baseball and a tennis/pickleball court with a basketball net, too! A group of notable Detroiters chose this area with its sap-filled Maple trees as a respite from city life and named it Sugar Bush Association in 1936. This tranquil spacious home was one of the earliest built on the association owned tree lined lane. It has over 3600 sq. ft. of living space and gorgeous water views seen from almost every room. While retaining the charm of the original house, nearly the entire exterior and interior of this home, including the chimney, was custom designed and remodeled in 1994 by architect Larry Graves and Easling Construction. Main floor offers gracious living spaces, 2 bedrooms, 2 baths, and main floor laundry. Upper level includes a large primary suite with private entrance, bath, walk-in closet and private balcony as well as family room/library, 2 bedrooms, and cedar closet. Outdoor features views of Manitou and Fox islands plus stunning sunsets, star gazing, professionally engineered staircase to Lake MI, automatic generator, and secondary garage for your toys! Located near Clay Cliffs and Houdek Natural Areas and only a 2.5 mile walk/bike/drive to Leland, known for scenic “Fishtown”. This well-built Northern Michigan home is ready for you!

5161 E Sugarbush Lane, Leland

$599,000

2 Baths ⋅ 1925139 MLS ⋅ N/A BLDG.

Rare opportunity to purchase this historic property in Downtown Leland just two blocks from iconic Fishtown and right next to Village Green. Featuring approximately 1,242 SF on 0.23 acres, this property has a ton of character and is in an unbeatable location. The building has been used as a real estate brokerage office for many years, but the tenant is relocating to another office in Leland, and it is time for this property to move on to it’s next chapter. The property is zoned commercial, but the Leelanau Conservancy has a historic conservation easement that restricts allowed uses and future redevelopment. This would make a great mixed-use property with commercial on the first floor and residential (or short-term rental) on the second floor. Don’t miss this once-in-a-lifetime opportunity to own a piece of Downtown Leland!

208 N Main Street, Leland

$1,150,000

3 Beds ⋅ 2 Baths ⋅ 1922046 MLS ⋅ N/A BLDG.

Sitting on nearly two acres, this classic cottage is high and dry and boasts 100 ft of private (across the road) frontage on North Lake Leelanau, just one mile south of Leland! The lakefront is easily deep enough for a 24ft boat and offers wonderful recreation opportunities on the one of the most beautiful and coveted lakes in all of Northern Michigan. Property on North Lake Leelanau is becoming harder and harder to come by, and this unique parcel offers a chance to wade in at a more reasonable price point than most you will find. The cottage has a main level primary bedroom, 2 baths, a kitchen with attached laundry room and 2 upstairs bedrooms. There is a main level sunroom that is the perfect spot to enjoy the sunrise over the lake. A two car detached garage with a separate workshop room, as well as a shed, sit behind the home. Three decks, two of them with water views, offer a great place to grill out or sit back and relax with your favorite beverage. With 1.8 acres behind the home & garage, there is plenty of room to roam in the woods, collect firewood, hunt for morels, or enjoy the proximity to the Leelanau Conservancy's "Whaleback Natural Area" which is just a short jaunt away and offers a fantastic hiking trail complete with a viewing platform overlooking Lake Michigan. Frequent visits from area wildlife including deer, owl, fox, and hawks complete the up north experience. Ride your bike into Fishtown, motor your boat up the Leland River for lunch or a cocktail, or launch your kayak or paddle board for a day of sun filled adventure in this vacation oasis. Home is in need of a new well and septic. Point of Sale Inspection report is available. Permits and contractor quotes are in process. Home is in a trust and being sold As Is.

1691 N Manitou Trail, Leland

$932,500

5 Beds ⋅ 3 Baths ⋅ 1906569 MLS ⋅ Brookwood Sub BLDG.

Welcome to Deer Run Farms, a meticulously restored historic property seamlessly blending modern comforts with timeless charm. Discover the allure of the kitchen with its luxurious granite countertops, a stunning cut-stone fireplace, and gleaming stainless steel appliances. Immerse yourself in the enchanting ambiance created by three magnificent cut-stone fireplaces and spacious living areas adorned with period decor. The partially finished basement offers a delightful family room and custom live edge bar, perfect for unforgettable gatherings. Conveniently located near downtown Leland, known as "fish town," this residence provides easy access to boating, dining, shopping, and golf. Nestled on nearly 3 acres of majestic hardwoods, Deer Run Farms offers both privacy and a front-row seat to observe wildlife. This exceptional home can be acquired fully furnished, ensuring immediate enjoyment. Highlights include a whole-house Generac generator, screened/open covered porches, and an oversized two-car garage. The tranquil potting shed awaits plant enthusiasts or provides extra storage. Explore nearby Traverse City, Suttons Bay, Sleeping Bear Dunes, Pyramid Point, wineries, orchards, hiking trails, and recreational activities. Welcome to Deer Run Farms—a blend of history, charm, and modern living, offering an exceptional lifestyle.

3257 N Manitou Trail W, Leland

$780,000

3 Beds ⋅ 2 Baths ⋅ 1916687 MLS ⋅ N/A BLDG.

A tastefully updated, classic three-bedroom, two-bathroom ranch home is situated on a private, double corner lot in the heart of Leland. Enjoy the spacious living room accentuated by large picture windows that provide an abundance of natural light. Hardwood floors are throughout the main living areas and bedrooms, with tile bathrooms. A combined yet private kitchen and dining room provide an inclusive prep and meal experience. Delightful master suite includes walk-in closet, his & her sinks and walk-in shower. During the warm seasons, you’ll enjoy al fresco dining on an outdoor patio and evening bonfires and lawn games in the backyard which is surrounded by a new privacy fence. Additional improvements include a new water softener, natural gas, new furnace and a/c, roof, and windows throughout. Located two blocks from Hancock Field park and recreation area that includes ball diamonds, soccer fields, tennis courts, skateboard ramps and picnic pavilions. Conveniently located to public beaches, Fishtown, shopping, dining, and recreation.

308 S Grand Avenue, Leland

$805,000

3 Beds ⋅ 2 Baths ⋅ 1909900 MLS ⋅ N/A BLDG.

Quintessential Georgian, colonial-style home located in the heart of Leland on an oversized, corner lot. Enjoy your morning coffee from the beautiful, and charming covered porch. The interior is equally delightful with formal living and dining rooms adorn natural wood flooring. Bright kitchen with tile flooring. A private room off the kitchen could be used as an office, studio, TV room, or additional bedroom. To the back of the house is an appealing addition that could be turned into a quaint three-seasons room. Upstairs is a spacious master bedroom set off to one side providing privacy from a common seating alcove that leads to two additional bedrooms and a full bathroom. Outdoors is an expansive outdoor deck, great for entertaining, and beautifully landscaped fenced lawn area for the maximum privacy. Kinetico water softener and Kinetico water filter on kitchen sink. Walking distance to restaurants, shopping, beach and all that historic Fishtown has to offer. Home is being sold furnished, except for the list under associated documents.

402 S Main Street, Leland

$520,000

3 Beds ⋅ 1 Baths ⋅ 1909556 MLS ⋅ Bartons Addn BLDG.

Great location on Fifth Street in Leland, modest 3 bedroom one bath 1200 square foot ranch on 1 and a half lots. Close to Leland Country Club, Handcock Recreational Field, just a few blocks from North Lake Leelanau access and 6 or so blocks from shopping, Library, Old Art Building, restaurants, Fishtown and Lake Michigan beaches.

305 S Fifth Street, Leland

$1,900,000

2 Beds ⋅ 2 Baths ⋅ 1920909 MLS ⋅ N/A BLDG.

Leelanau delight! Rare opportunity to own a home on an estate-sized parcel (3.45 acres) where you can enjoy world-class sunsets over the Manitou Islands, Pyramid Point, and Good Harbor Bay. The main house features two bedrooms and two bathrooms, and a 2-car detached garage with covered walkway. The living room features a gas fireplace. Sunroom and outdoor deck with expansive views. Detached guest studio provides an additional 540 sq ft and awaits your final touches to finish the bathroom and add a kitchenette. There is a private staircase to access the 200 ft of private Lake Michigan frontage. Being sold furnished. The sq. ft. total includes 1,636 sq. ft. in the main house and 540 sq. ft. finished in the detached studio. House has Generac generator for backup for part of the house.

1451 N Leland Estates Drive, Leland

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