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$1,100,000
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
$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
$2,000,000
1945618 MLS ⋅ Chandler's Park Addition BLDG.
Rare opportunity in downtown Leland - one of the last buildable riverfront properties on the Leland River. 0.32 ± acres with approximately 129' of river frontage. 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 adjacent lot with existing home is for sale separately or buy both properties together. Use the lot for your custom dream home 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.

TBD 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
$1,100,000
4 Beds ⋅ 2 Baths ⋅ 1945155 MLS ⋅ Waterford Hills BLDG.
This beautifully remodeled home offers modern comfort and timeless style in every detail and includes 500 ft of shared frontage on North Lake Leelanau. Step inside to discover an open-concept layout featuring new flooring throughout and a designer island kitchen equipped with premium Café appliances, perfect for entertaining or everyday living. Every inch of this home has been thoughtfully upgraded, including all-new bathroom fixtures, interior doors, energy-efficient windows, and sliding glass doors that flood the living spaces with natural light. The brand-new front entry door, garage door, and the exterior has been professionally landscaped and includes underground irrigation. Major system upgrades include brand-new plumbing and a high-efficiency HVAC system, ensuring peace of mind and year-round comfort. A freshly paved driveway adds the finishing touch to this turnkey property. Don’t miss your chance to own this meticulously updated home that blends quality craftsmanship with modern amenities in a move-in-ready package.

4005 E Oxford Drive, 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
$1,000,000
1944502 MLS ⋅ N/A BLDG.
Nestled in the heart of Leland, this rare offering captures the essence of Leland charm with one of the most iconic views in the area. Overlooking the beloved boathouse visible from the historic bridge in Leland, this property offers a front-row seat to the timeless beauty and activity of the Leland River. With 25 feet of private frontage on the river, enjoy direct access to the sparkling channel connecting Lake Leelanau and Lake Michigan, perfect for boating, kayaking, or simply soaking in the serene waterfront setting. Whether it’s watching the boats pass by, strolling into town for dining and shopping, or taking in sunsets over the water, this location offers an unmatched lifestyle. A truly unique opportunity to own a slice of Leland’s most photographed and cherished landscape. Purchase the vacant lot about a block away to build your dream home with views of the Leland River and have your boathouse steps away, see MLS #1942745.

195 E Cedar Street, Leland
$1,395,000
1944015 MLS ⋅ N/A BLDG.
Perched along the shores of Lake Michigan in highly sought-after Leland, this exceptional bluff-top property offers 250 feet of private waterfront and breathtaking, unobstructed sunset views. Tucked away at the end of High Bluffs Drive, the setting provides unmatched privacy and tranquility, surrounded by the natural beauty of Northern Michigan. Enjoy elevated panoramic vistas of the lake, with sweeping views of the Manitou Islands and ever-changing colors painting the horizon each evening. The generous frontage and bluff-top elevation create a rare opportunity for a legacy property with incredible building potential. Whether you envision a peaceful retreat or a luxury waterfront estate, this remarkable parcel delivers an ideal combination of seclusion, scenery, and coveted Lake Michigan frontage.

N Manitou Trail, Leland
$1,893,000
3 Beds ⋅ 2 Baths ⋅ 1937545 MLS ⋅ N/A BLDG.
Nestled on an incredibly rare, private 2.47 wooded acres in Leland, this 3-bedroom, 2-bath home offers the perfect blend of comfort and convenience. Located along the 8th fairway of the prestigious Leland Country Club, you’ll enjoy golf course views and easy access to all that Leland has to offer. Walk to Lake Michigan beaches, historic Fishtown, shops, and restaurants, this is the ideal Up North retreat or year-round residence. The home features solid surface countertops, gas fireplace, a main-floor primary suite, and a spacious deck for outdoor entertaining. Beautiful, mature landscaping enhances the natural surroundings, creating a peaceful oasis just minutes from downtown Leland.

420 N Grand Avenue, Leland
$1,885,000
4 Beds ⋅ 4 Baths ⋅ 1936344 MLS ⋅ Leland River Lots Site Condo BLDG.
Welcome to this beautifully designed three-level home with 40 feet of private waterfront on the Leland River and a perfect blend of comfort, elegance, and functionality. With 4 bedrooms and 3.5 beautifully appointed bathrooms, this home is designed for both relaxation and entertaining. Step inside to discover luxury vinyl plank flooring throughout the primary living areas, the living room features a cozy gas fireplace, creating a warm and inviting atmosphere, while a separate den offers flexible space for work or leisure. An elevator provides easy access to all three levels, making every part of the home convenient and accessible. Outdoor living is elevated with three covered porches, a backyard patio, and a riverfront patio—perfect for enjoying tranquil views and riverfront sunsets. The professionally landscaped yard enhances the natural beauty of the surroundings. Additional highlights include a 2-car garage and unfinished room ideal for adding a 5th bedroom or additional bathroom, offering room to grow and customize. This exceptional Leland Riverfront property combines luxury, practicality, and the peaceful charm of Leland living. Seller may considering selling some furnishings separately from the house.

145 S Chandler 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
$1,800,000
3 Beds ⋅ 3 Baths ⋅ 1935919 MLS
Lake Michigan Bluff Retreat - Perched high above Lake Michigan on a dramatic bluff, this striking A-frame home offers panoramic, west-facing views that stretch for miles. Set on 6 private acres, the setting is as timeless as it is breathtaking—with shared access to North Lake Leelanau just a short drive away. From the moment you arrive, a beautiful brick driveway sets the tone, leading to a custom home wrapped in warm stone siding and defined by bold rooflines. Step inside to a showstopping great room featuring vaulted tongue-and-groove ceilings with exposed beams, a floor-to-ceiling stone fireplace, and walls of glass that flood the space with natural light and frame the endless lake views. The main level includes two well-appointed bedrooms and a shared full bath. Upstairs, the spacious primary suite offers a lofted sitting area, en-suite bath, and a spiral staircase leading to an additional sleeping loft—ideal for kids. The lower level adds a large game and rec room with a second wood-burning fireplace, half bath, and plenty of space to entertain. Outside, enjoy a spacious lakeside deck, manicured lawn, and a firepit area for gathering under the stars. A three-car attached garage provides ample storage for vehicles and gear, while the wooded acreage ensures privacy. As a bonus, enjoy deeded access to a separate, shared waterfront parcel on North Lake Leelanau with a dock—perfect for boating, paddleboarding, kayaking, or swimming. This one-of-a-kind property blends design, setting, and lifestyle in one of Leelanau County’s most spectacular blufftop locations. Home is being sold fully furnished.

4171 N High Bluffs Drive, Leland
$1,600,000
9 Beds ⋅ 10 Baths ⋅ 1933103 MLS ⋅ Village Of Leland BLDG.
Charming home within the Village of Leland. Walkable to N Lake Leelanau access, Fishtown's amazing harbor/shops, & all the amenities that Leland has to offer. Constructed by Biggs Construction as an Assisted Living residence, this home offers many opportunities for conversion to an incredible family/friendly home. Many barrier-free features, no step side entry & car port, expansive covered porch, backyard gardens/decks, beautiful kitchen w/multi pantry storage & private office/study with 1/2 bath. Spacious dining room, living room with gas fireplace, & 2 library-sitting rooms. 8 bedrooms on main level w/private baths, one large bedroom/bath on second level. Incredible fire suppression system & multiple storage areas in basement. View this property & let your imagination soar.

300 S Grand Avenue, 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
$1,608,000
5 Beds ⋅ 4 Baths ⋅ 1931529 MLS ⋅ Brookwood Subdivision BLDG.
Imagine owning these sunsets while relaxing in your very own Leland waterfront home. This contemporary Glen Arai designed home has been completely renovated within the last two years to incorporate the Arai architectural lines, world-class Lake Michigan views, and natural light to create a shoreside, coastal retreat. The home, located on 2.4-acres is nestled atop a bluff with unobstructed views of the Manitou Passage and private frontage below. The home incorporates four distinct levels in addition to a guest house to accommodate a haven for you and your extended family or friends. An open and welcoming living area includes a well-appointed kitchen and dining area with a sitting room, beautiful wood fireplace clad in river rock while enjoying the stunning Lake Michigan vista. The primary suite is located on the one level up with terrace balconies and an abundance of light to enjoy the views of the Manitou Islands from the bedroom and bathroom. The top floor is a bunk room/loft that provides expansive panorama and additional sleeping for guests and extended family. The lowest floor provides access from the ground level and includes a large family room, two additional bedrooms (one non-conforming) and a shared bathroom. A bonus guest house is set atop a drive-through, detached garage that provides perfect storage for boats and additional recreation vehicles, while the guest house includes a kitchenette, sitting & sleeping area. Located just one mile from the Village of Leland and historic Fishtown where you can enjoy shopping, restaurants, galleries and beaches. A detailed list of improvements can be found in the associated documents. Nearby full-service marina could provide convenient storage and drop-in service to enjoy boating on Lake Leelanau within one mile from your home. Furnishings are negotiable.

4781 E Golfview Drive, 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
$1,250,000
4 Beds ⋅ 4 Baths ⋅ 1926193 MLS
Remarkable opportunity to build a classic cottage home in the heart of Leland with J. Peterson Homes, Northern Michigan’s finest custom homebuilder. Located just steps from the beach, shops and restaurants, the home features an open main floor with large front porch, spacious kitchen, dining and living area. Upstairs offers a primary suite with a slider leading to an upper deck for morning coffee. Two additional bedrooms, a hall bath and laundry closet complete the second story. Lower level offers daylight windows in the bedroom and family room plus a game area and full bath. Amenity includes Pella windows, quartz countertops, Kohler plumbing fixtures, engineered wood floors, LP smartsiding and all the quality you expect from J. Peterson Homes. Pricing includes landscaping and one stall detached garage. LLC Member is a Broker in the State of MI.

211 N Main Street, Leland
$1,230,000
1923326 MLS ⋅ Metes And Bounds BLDG.
Rare Never Developed 100 foot wooded parcel on N Lake Leelanau just north of Leland on gorgeous sandy frontage! The parcel has its own tax id number and is approved for a standard septic - additional information is in the associated documents. The opportunities abound on this stunning parcel, build your dream house and enjoy all that northern michigan lake life has to offer.

V/L N Manitou Trail, Leland
$1,650,000
4 Beds ⋅ 3 Baths ⋅ 1923325 MLS ⋅ Metes And Bounds BLDG.
100 feet of Pristine Sandy Frontage on North Lake Leelanau, with a 4 bedroom 2.5 bath artistically designed home set down at the waters edge. Home features expansive lake views and a spacious deck to take full advantage of lakeside living. The spacious living room features a gorgeous natural stone wood burning fireplace and full lake views, kitchen and dining rooms are both graciously sized and ideal for entertaining. Guest bath is conventiently located off living room. Primary bedroom is at the end of the home for privacy, large windows provide amazing natural light. 3 additional bedrooms are upstairs and share a guest bath. 2 bedrooms have loft space - who wouldn't love a bedroom with its own loft! Studio or home office space connects the house to the bonus space over the 2 car garage. Home is ready for its new owners to update with their style but has very compelling design elements.

4040- N Manitou Trail, 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
$1,500,000
1 Baths ⋅ 1914936 MLS ⋅ N/A BLDG.
Rare Opportunity To Purchase and Own a Commercial Property with Direct Leland River Frontage in Downtown Leland! The current building is primarily a large, light and bright, open space that currently is operated as an art gallery, "Main Street Gallery", and also lends itself to a variety of uses or an easy space to build out to meet your vision. With direct, private Leland River frontage and boat slips, use your imagination and cater to boaters! Seldom does an opportunity as this present itself in downtown Leland with so many options.

307 S Main 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