Oakland, WI Homes for Sale (13 Real Estate Listings)

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$1,199,000

W8849 Deer Run Trail, Oakland

5 Beds 3.5 Baths 1 Acres 4,833 SqFt Single Family MLS® # 1999743

Stately custom-built home on cul-de-sac overlooking Lake Management Preserve. Two-story entry showcases birch floors, open staircase, vaulted great room with wall of windows displaying gorge...

$962,000

W8778 Blue Violet Court, Oakland

5 Beds 3 Baths 1 Acres 2,882 SqFt Single Family MLS® # 2009799

Completion 6/2025. Welcome to this stunning country cottage, a standout in the June 2026 Parade of Homes. This upscale ranch will feature Amish cabinetry, a primary suite seamlessly connecte...

$765,000 Lake Ripley

W9160 Ripley Road, Oakland

3 Beds 2 Baths 0 Acres 1,596 SqFt Single Family MLS® # 2009515

Charming "TURNKEY" home ready for you to move in and enjoy the pleasures of lake living. Located just minutes from downtown Cambridge & an easy drive to Madison, Milwaukee or Chicago. Proper...

$650,000

↓ $45,000

W8874 Deer Run Trail, Oakland

2 Beds 2.5 Baths 1 Acres 1,861 SqFt Single Family MLS® # 2006645

Peaceful setting with modern comforts—perfect for nature lovers and those who value craftsmanship. This delightful 2 bed, 2.5 bath Wilderness log home on 1.47 acres backs up to Lake Ripley C...

$585,000 Lake Ripley

↓ $5,000

N4522 Park Road, Oakland

3 Beds 1.5 Baths 1 Acres 1,570 SqFt Single Family MLS® # 2008492

Modern style, 1-1/2 story, cuddled by Mother Nature offering lake views & lake access. One-owner home w/passive solar construction w/1’ thick brick & mortar walls, electric heat & ductless m...

$550,000

N4625 Prairie Rose Road, Oakland

4 Beds 3 Baths 0 Acres 3,618 SqFt Single Family MLS® # 2008713

Surrounded by beautiful trees, this .46 acre property located in a rural subdivision has it all! From the in-ground solar heated salt water pool, to the Sauna in the lower level. From the f...

$519,900 Lake Ripley

↓ $20,000

W9404 Porter W9408, Oakland

4 Beds 3 Baths 0 Acres 2,256 SqFt Single Family MLS® # 1910211

Great opportunity to have it all! Walk accross the street to your LAKE ACCESS with a PIER and BOAT SLIP! 2 Homes for your mother-in-law as well! The cute 2BR-LR/dining/kitchen/BA home ab...

Lannon Stone Realty LLC

$485,000 Lake Ripley

W9380 Ripley Road, Oakland

3 Beds 1.5 Baths 1,008 SqFt Single Family MLS® # 2010174

Charming stand alone A-frame at 4 unit Ripley Condominiums on Lake Ripley. 81’ of frontage with pier shared with 3 others and includes a boat lift! This turn key fully furnished, fully decor...

$445,000

N4021 County Road A, Oakland

3 Beds 2 Baths 2 Acres 1,724 SqFt Single Family MLS® # 1936213

Welcome to this wooded oasis conveniently located just 5min to Cambridge and 20min to Madison! The open concept kitchen flows into dining area and living room- with gas fireplace, and patio...

Wayne Hayes Real Estate LLC

New

$430,000

W8908 Us Highway 18, Oakland

3 Beds 2 Baths 1 Acres 2,000 SqFt Single Family MLS® # 1940032

Tucked away on 1.48 acres, this Raised Ranch home offers 3 bedrooms and 1.5 bathrooms, ideal for those who value privacy and outdoor space. The custom oak kitchen is a standout feature, boas...

Wayne Hayes Real Estate LLC

$425,000

N4353 Poplar Avenue, Oakland

1 Bed 1.5 Baths 0 Acres 1,304 SqFt Single Family MLS® # 2006679

Newly listed in scenic Cambridge, this custom-built log home by Tomahawk Log Homes offers a tranquil setting with access to Lake Ripley. Beautifully landscaped grounds enhance curb appeal an...

$395,000

29031 French Road, Oakland

2 Beds 1 Bath 39 Acres 612 SqFt Single Family MLS® # 6789574

This beautiful Northwest Wisconsin cabin combines rustic charm, modern comforts, and a one-of-a-kind connection to hunting history. Fully furnished and thoughtfully decorated, the cabin feat...

Whitetail Properties Real Esta

$260,000

N4521 W Shore Place Road, Oakland

2 Beds 1 Bath 0 Acres 1,140 SqFt Single Family MLS® # 2004371

If you are looking for your lake property, look no further than Lake Ripley in Cambridge. This property is in really nice shape and has been in this Family for decades, 2 bed, 1 full bath wi...

Oakland, WI Real Estate Statistics

Average Price	$304K
Lowest Price	$33K
Highest Price	$1.2M
Total Listings	36
Avg. Days On Market	68
Avg. Price/SQFT	$338

Property Types (active listings)

As of October 25, 2025 there are 13 active Oakland, WI real estate listings for sale with an average listing price of $590,069. The highest-priced property listing is $1,199,000, while the lowest priced property can be purchased for $260,000. Oakland, WI homes for sale have an average price of $332 per square foot, based on listings with an average of 3.1 bedrooms, 2.1 bathrooms, and 2,031 square feet of living space.