Three Oaks Homes under $500,000

Three Oaks Homes under $500,000

Welcome to Three Oaks, Michigan – a hidden gem nestled in the heart of Berrien County. This charming village, steeped in rich history and vibrant culture, offers a unique blend of small-town warmth and modern amenities. With its picturesque landscapes, welcoming community, and a thriving arts scene, Three Oaks is the perfect place to call home.

Located just a short drive from the stunning shores of Lake Michigan, Three Oaks boasts an enviable location that allows residents to enjoy both serene countryside living and easy access to beachside recreation. The village is known for its quaint downtown area, featuring delightful shops, cozy cafes, and local eateries that serve up delicious fare, making it a haven for foodies and shoppers alike.

For those seeking their dream home, Three Oaks offers a variety of charming properties, many of which are priced under $500,000. Whether you are looking for a cozy cottage, a spacious family home, or a modern residence with all the latest amenities, there’s something for everyone in this delightful community. With its affordable housing options, Three Oaks is an ideal destination for first-time buyers, families, and retirees alike.

In addition to its beautiful homes, residents enjoy a plethora of outdoor activities, from hiking and biking trails to nearby parks and nature preserves. The sense of community here is palpable, with numerous events and festivals throughout the year that bring neighbors together.

Discover the magic of Three Oaks, where affordable living meets a vibrant lifestyle. Your dream home awaits!

Newest Three Oaks Homes under $500,000

22 W Ash Street, Three Oaks
$420,000
3 Beds ⋅ 2 Baths ⋅ 26052288 MLS ⋅ ACTIVE Status
RARE TURNKEY RENTAL OPPORTUNITY IN THE HEART OF THREE OAKS! This fully furnished, established licensed ST rental is being sold furnished and ready for its next chapter. Its existing rental status in the Village of Three Oaks is especially notable, as the number of licenses is limited and new licenses are currently capped. This spacious 3-bed, 2-bath home has approximately 1800 square feet and combines the charm of a traditional Three Oaks home with the features many occupants are looking for. Inside, you'll find three generously sized bedrooms, two full bathrooms, spacious living and dining areas, a full kitchen, main-floor laundry, and a huge family room. Hardwood flooring and the home's character create a warm, inviting atmosphere, while the included furnishings make this a true turnkey property. Outside, enjoy a fenced backyard, rear deck, fire pit, and welcoming front porch-great spaces for relaxing outdoors. The property is conveniently located near New Buffalo, with access throughout Southwest Michigan and Northwest Indiana. It is also close to downtown Three Oaks with convenient access to restaurants, shopping, and entertainment. Buyer should independently verify current Village of Three Oaks rental regulations, license status and whether the property's existing license/registration may transfer or continue following a change in ownership. Owner is an Illinois real estate agent. Some photos have been virtually rendered.

22 W Ash Street, Three Oaks
7571 US Hwy 12 Highway, Three Oaks
$219,000
4 Beds ⋅ 2 Baths ⋅ 50222500 MLS ⋅ ACTIVE Status
Here's a rare opportunity. Great house on some real acreage in highly-coveted Three Oaks. Property will need some repairs. Cash buyers only please. Do not wait, this will not last.

7571 US Hwy 12 Highway, Three Oaks
707 Tulip Drive, Three Oaks
$429,000
4 Beds ⋅ 2 Baths ⋅ 26046299 MLS ⋅ ACTIVE BACKUP Status
NEW PRICE - Rare find! This house has both the advantages of being in the village of Three Oaks as well as having room to breathe. This .73 acre lot IS the southeast corner of the village, located at the very end of Tulip Drive. Enjoy peaceful views of the fields to the east and south as far as you can see. A friendly, yet quiet neighborhood welcomes you. The primary suite boasts a vaulted ceiling and a generous walk-in closet. The large, DRY walk-out basement is ready for finishing, has 9' ceilings, and plumbed for a full bathroom. New in 2026: Water softener, sump pump. Odorless water from the faucets!

707 Tulip Drive, Three Oaks
8000 Warren Woods Road Unit 62, Three Oaks
$89,900
3 Beds ⋅ 2 Baths ⋅ 26046102 MLS ⋅ ACTIVE Status
Lake Michigan Retirement without the Lake Michigan price tag! Less than 10 minutes from Harbert Beach and Gordon Beach, this fully furnished 3-bedroom, 2-bath home offers a spacious primary suite, bonus sitting room, open-concept living, two large decks, and access to a community pool, clubhouse, and gym—all in a truly move-in-ready package. Enjoy retirement living in Lakewood Estates 55+ community! This spacious 1997 Palm Harbor home offers 3 bedrooms, 2 full bathrooms, flexible living spaces, and comes fully furnished with furniture and appliances included—making it truly move-in ready. Seller's personal artwork and many wall hangings are excluded. The primary suite features an ensuite bath with dual sinks, soaking tub, separate shower, and walk-in closet, plus a private sitting room perfect for an office, reading nook, or hobby space. The open-concept living, dining, and kitchen areas create a welcoming space for everyday living and entertaining, with a breakfast bar and additional dining area. Outside, enjoy two decks, one large and small, a storage shed, and two-car parking patio. Lot rent is $650/month and includes water, sewer, trash, shed, main-road snow plowing, plus access to the clubhouse, pool, and gym. Buyer is responsible for lawn care and snow removal from their parking area. With generous living space, community amenities, furnishings included, and Lake Michigan beaches less than 10 minutes away, this home offers comfort, convenience, and a relaxed lakeshore lifestyle!

8000 Warren Woods Road Unit 62, Three Oaks
210 S Elm Street, Three Oaks
$225,000
5 Beds ⋅ 3 Baths ⋅ 26046018 MLS ⋅ ACTIVE BACKUP Status
Step back in time with this charming 1890s Victorian in the heart of Three Oaks, once operated as a bed and breakfast and filled with history, character, and so much potential. This spacious five-bedroom, three-full-bath home features beautiful original woodwork, rich dark oak doors, vintage windows, and timeless details throughout. Two en suite bedrooms offer added flexibility, along with laundry on both the main floor and upstairs. The cozy kitchen nook, formal dining room, three season front porch, back deck, and sweet screened in balcony off an upstairs bedroom adds even more charm and plenty of spaces to enjoy. This home does need work and is being sold in as-is condition, but for the right buyer with vision, the possibilities are truly special. With its incredible history, generous size, and one of a kind character, she is just waiting for someone to bring her back to her full beauty.

210 S Elm Street, Three Oaks
105 Locust Street E, Three Oaks
$190,000
3 Beds ⋅ 2 Baths ⋅ 26044995 MLS ⋅ ACTIVE Status
A CHARACTER RICH RESTORATION PROJECT AWAITS..... **A THREE OAKS ORIGINAL—RESTORE, REIMAGINE & MAKE IT YOURS!** Located on E. Locust Street, surrounded by some of Three Oaks' beautiful historic homes, this vintage 1920s brick residence offers the rare opportunity to restore a home with genuine character and create something truly special. The 3-bedroom, 2-bath layout includes a main-floor bedroom and an abundance of original architectural details waiting to be brought back to life. Much of the original woodwork remains beneath layers of paint, along with original trim and painted hardwood floors—details that can become the foundation for an exceptional renovation. The home's setting is particularly compelling. Three Oaks grew into a prosperous village in large part because of the remarkable success of local industrialist and inventor E.K. Warren. In 1883, Warren patented "Featherbone," an innovative and more durable alternative to whalebone used in corsetry, and opened his first factory right here in Three Oaks. The Warren Featherbone Company would go on to become an international enterprise, manufacturing featherbone, corset materials, whips and other products while employing generations of local residents. The historic E.K. Warren office building, constructed in 1905 and now home to the Three Oaks Township Public Library, served as the company's headquarters from 1905 to 1928. Today, East Locust Street is a desirable part of Three Oaks, surrounded by well-kept homes and the character that makes the village so appealing. Nearby homes that have been thoughtfully renovated have done very well, making this a great opportunity for someone willing to put in the work and bring this home back to life. Outside, the generous yard provides plenty of room for gardening, entertaining, play and your four-legged family members, with a portion already fenced. For the buyer with vision, craftsmanship and a willingness to put in the work, the sweat equity here could be substantial. Bring your ideas, your tools and your appreciation for old-house character—and give this Three Oaks original the restoration it deserves.

105 Locust Street E, Three Oaks
6859 Kruger Road, Three Oaks
$450,000
3 Beds ⋅ 2 Baths ⋅ 26044486 MLS ⋅ ACTIVE Status
Welcome to your Southwest Michigan retreat! This charming 3-bedroom, 2-bath home sits on 5 spacious acres in the heart of Harbor Country, offering the perfect blend of privacy, natural beauty, and convenient access to area attractions. Enjoy phenomenal sunset views overlooking nearly 4 acres of tillable property, plus a large pole barn offering excellent space for storage, hobbies, equipment, or a workshop. Located just a short distance from the vibrant downtown of Three Oaks, you'll be close to boutique shops, renowned distilleries, restaurants, theaters, and the stunning shoreline and beaches of Lake Michigan, while still enjoying the peace and serenity of your own private acreage. Located in Three Oaks township STR is allowable. Don't miss the opportunity to own a piece of Harbor Country. Book your showing today!

6859 Kruger Road, Three Oaks
3334 W Glendora Road, Three Oaks
$255,000
4 Beds ⋅ 1 Baths ⋅ 26042294 MLS ⋅ ACTIVE Status
With 2.36 acres on the East Branch of Gailen River sits this 4 bedroom 1 bathroom ranch home! Inside you have so many updates with a rustic feel. Previous owner had move the laundry upstairs in the 4th bedroom. Full unfinished basement is the perfect area for storage and playing on the pool table that stays with the home. Outside you have a fenced area for animals and a small shed. Across the river you have a 2 car detached garage with a walk up loft. The property includes two lots with over 2.36 acres and creek running through it. Go fishing in your backyard, yes you can even caught Salmon in the spring! Road frontage on both Glendora & Pardee Roads. Call Jeffrey A Penick today to see this house before it's Sold at 269-420-4756

3334 W Glendora Road, Three Oaks
24 W Linden Street W, Three Oaks
$399,000
3 Beds ⋅ 2 Baths ⋅ 26041093 MLS ⋅ ACTIVE Status
Situated in the heart of charming Three Oaks, yet tucked away on a quiet street, this historic gem is filled with character, history, and opportunity. Documented records show the property was once owned by Charles Warren and the Chamberlain family, two names woven into the rich history of Three Oaks. Local history also suggests the home may have been connected to one of the village's most significant historic buildings, and we're continuing to uncover its fascinating past. Inside, soaring vaulted ceilings, original wood floors, exposed wood beams, leaded stained glass windows, and a cozy wood-burning stove create a warm, loft-inspired space full of historic charm. Major improvements have already been completed, including updated 200-amp electrical service, cast iron and copper plumbing replaced during the 2000 renovation, reinforced floor joists, and the installation of a substantial structural support beam. Offering 3 bedrooms, 2 bathrooms, potential for a 4th bedroom, and a sun-filled four-season room, this home is simply waiting for its next owner to add the finishing touches and bring the vision to life. Situated on 0.40 acres, the property also features a massive pole barn with electrical service already in place and a plumbing line run to the building, awaiting final connection. The beautifully landscaped yard is filled with perennial gardens, productive garden spaces, a magnificent fragrant lilac shrub, and stunning sunset views over the neighboring field. Zoned MU-2 (General Mixed Use), the property offers exceptional flexibility, subject to Village approval, with possibilities including a live/work space, boutique business, gallery, office, or even a short-term rental. Historic homes with this level of character, history, extensive updates, flexible zoning, and potential rarely come to market. This is a rare opportunity to own a truly special piece of Three Oaks history.

24 W Linden Street W, Three Oaks
7767 Warren Woods Road, Three Oaks
$499,000
2 Beds ⋅ 2 Baths ⋅ 26040448 MLS ⋅ ACTIVE Status
Create your COOL modern container home compound on 4.2 peaceful acres with mature trees, a private pond, and a bridge leading to a charming island . This one-of-a-kind property is ready for your finishing touches, with major infrastructure already completed: water hookup, interior framing, 400-amp electric service and wiring, 4 mini-splits, closed-cell insulation, septic mound installed, and septic tanks on site. The bright-open-concept design includes 2 spacious bedrooms, 2 baths, 9' ceilings, and an upper bonus room with access to a rooftop deck. Designed to bring the outside in! Staging and renderings are included to help showcase the vision. Two additional containers offer storage, studio, or workspace potential. Endless possibilities in an idyllic Harbor Country location. Offered at $499,000

7767 Warren Woods Road, Three Oaks
614 Magnolia Street, Three Oaks
$349,900
2 Beds ⋅ 2 Baths ⋅ 26040039 MLS ⋅ ACTIVE Status
Enjoy modern comfort and rustic charm at the south edge of the Village of Three Oaks. Sip morning coffee on the front porch amid mature trees, sunrise, and birdsong. Recent upgrades: new auto garage doors, roof & utility door (2022), AIM treatment system (2023), furnace, water heater, landscaping, fencing, and a 4-person sauna (2024). Inside: cozy den with fireplace (bed 3); open living/dining with 9' ceilings and exposed brick; an expansive primary spans the home. Owner is a Michigan-licensed real estate salesperson.

614 Magnolia Street, Three Oaks
8000 Warren Woods Road Unit 100, Three Oaks
$116,000
3 Beds ⋅ 2 Baths ⋅ 26039625 MLS ⋅ ACTIVE Status
Escape to Harbor Country in this beautifully maintained, fully furnished 2002 manufactured home in Lakewood Estates. Thoughtfully decorated with tasteful furnishings and décor, this move-in-ready retreat features a spacious living room with a fireplace, eat-in kitchen with sliding doors to a massive deck, main-floor laundry, three bedrooms, and a private primary suite with walk-in closet and ensuite bath. The peaceful backyard offers a quiet setting for relaxing or entertaining. Ideally located just minutes from Three Oaks, New Buffalo, Lake Michigan beaches, Bridgman, local wineries, breweries, charming shops and restaurants. Only 25 minutes to Notre Dame and approximately 1 hour 25 minutes to Chicago. Whether you're looking for a weekend escape, seasonal retreat, or year-round home, this is an affordable opportunity to own your own piece of Southwest Michigan.

8000 Warren Woods Road Unit 100, Three Oaks
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