Real Estate Investment Properties for Sale in Milton, WI

Looking for investment property in Milton, WI with high ROI ?

Explore a variety of short-term homes & houses in Milton, WI. Invest wisely with VRBO & Milton, WI Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Milton, WI

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
Lot 60 Lakeside Dr Milton, WI Lot 60 Lakeside Dr, Milton, WI 53534 \| Other	N/A beds \| N/A baths \| N/A	$184,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.1% Airbnb Rental Income: $null Traditional Rental Income: $801 Airbnb ROI: N/A Traditional ROI: 1.1%
Lot 10 Kido Way Milton, WI Lot 10 Kido Way, Milton, WI 53546 \| Other	N/A beds \| N/A baths \| N/A	$254,900	Airbnb cash on cash: N/A Traditional cash on cash: -0.75% Airbnb Rental Income: $null Traditional Rental Income: $593 Airbnb ROI: N/A Traditional ROI: -0.75%
3496 Pickard Dr Milton, WI Don't miss your opportunity to own this beautifully updated home in the desirable Ridges o...	3 beds \| 2 baths \| 2,760 sq.ft.	$429,900	Airbnb cash on cash: 1.29% Traditional cash on cash: 4.18% Airbnb Rental Income: $1937 Traditional Rental Income: $2589 Airbnb ROI: 1.29% Traditional ROI: 4.18%
323 S John Paul Rd Milton, WI Back on the market, buyers financing fell through. Solid & affordable 2 bedroom, 1 bath, 1...	2 beds \| 1 baths \| 720 sq.ft.	$265,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 2.41% Airbnb Rental Income: $1830 Traditional Rental Income: $1087 Airbnb ROI: 3.4% Traditional ROI: 2.41%
101 N Clear Lake Ave Milton, WI Lovely older home in Milton. Close to schools and shopping. Big 2 car garage with a den/of...	4 beds \| 2 baths \| 2,400 sq.ft.	$375,000	Airbnb cash on cash: 3.28% Traditional cash on cash: 3.9% Airbnb Rental Income: $2538 Traditional Rental Income: $2146 Airbnb ROI: 3.28% Traditional ROI: 3.9%
7938 E Highway 59 Milton, WI Fisherman's Paradise! Fully stocked 30' deep pond/lake w/private island. How fun would a z...	3 beds \| 3 baths \| 2,536 sq.ft.	$720,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 2.36% Airbnb Rental Income: $1937 Traditional Rental Income: $2936 Airbnb ROI: 0.11% Traditional ROI: 2.36%
2309 E Pine Tree Ct Milton, WI Welcome home to this beautifully maintained 4-bedroom, 4-bath residence situated on 1.19 a...	4 beds \| 3 baths \| 3,196 sq.ft.	$609,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 3.93% Airbnb Rental Income: $2538 Traditional Rental Income: $3477 Airbnb ROI: 1.2% Traditional ROI: 3.93%
3537 Samson Dr Milton, WI Come check out this beautiful new construction home in Milton School District. Open floor ...	3 beds \| 2 baths \| 2,017 sq.ft.	$559,900	Airbnb cash on cash: 1.5% Traditional cash on cash: 4.3% Airbnb Rental Income: $1937 Traditional Rental Income: $2890 Airbnb ROI: 1.5% Traditional ROI: 4.3%
1015 E High Street Milton, WI Well-cared-for 2 bed, 2 bath, 1,276 sq ft home on a .45-acre residential lot with a attahe...	2 beds \| 2 baths \| 1,376 sq.ft.	$750,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 0.92% Airbnb Rental Income: $1830 Traditional Rental Income: $1825 Airbnb ROI: 0.22% Traditional ROI: 0.92%
367 Ridge View Dr #16 Milton, WI This new construction condo overlooks Ridge View Park and driving range & is located in Mi...	3 beds \| 2 baths \| 1,967 sq.ft.	$549,900	Airbnb cash on cash: 0.48% Traditional cash on cash: 3% Airbnb Rental Income: $1937 Traditional Rental Income: $2725 Airbnb ROI: 0.48% Traditional ROI: 3%
4444 John Paul Road Milton, WI Conveniently located 3-bedroom, 1.5-bath home set on a spacious 0.69-acre lot in the highl...	3 beds \| 2 baths \| 1,355 sq.ft.	$289,900	Airbnb cash on cash: 2.76% Traditional cash on cash: 5.08% Airbnb Rental Income: $1937 Traditional Rental Income: $2057 Airbnb ROI: 2.76% Traditional ROI: 5.08%
5481 Arrowood Ln Milton, WI 5481 Arrowood Ln, Milton, WI 53563 \| Single Family Residential	3 beds \| 2 baths \| 1,891 sq.ft.	$574,900	Airbnb cash on cash: -0.35% Traditional cash on cash: 1.21% Airbnb Rental Income: $1937 Traditional Rental Income: $2266 Airbnb ROI: -0.35% Traditional ROI: 1.21%
Lot 26 Kido Way Milton, WI Lot 26 Kido Way, Milton, WI 53563 \| Other	N/A beds \| N/A baths \| N/A	$124,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.36% Airbnb Rental Income: $null Traditional Rental Income: $594 Airbnb ROI: N/A Traditional ROI: 1.36%
1168 Red Hawk Dr Milton, WI 1168 Red Hawk Dr, Milton, WI 53563 \| Other	N/A beds \| N/A baths \| N/A	$99,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.35% Airbnb Rental Income: $null Traditional Rental Income: $592 Airbnb ROI: N/A Traditional ROI: 2.35%
2338 E Pine Tree Ct Milton, WI Immaculately maintained tri-level home nestled on a quiet cul-de-sac in the Milton Sch Dis...	3 beds \| 3 baths \| 2,303 sq.ft.	$497,500	Airbnb cash on cash: 0.9% Traditional cash on cash: 4.05% Airbnb Rental Income: $1937 Traditional Rental Income: $2891 Airbnb ROI: 0.9% Traditional ROI: 4.05%
381 Ridge View Dr #4 Milton, WI This new construction condo overlooks the 13th hole of Oak Ridge Golf Course & is located ...	2 beds \| 2 baths \| 1,667 sq.ft.	$545,900	Airbnb cash on cash: 0.82% Traditional cash on cash: 2.74% Airbnb Rental Income: $1830 Traditional Rental Income: $2314 Airbnb ROI: 0.82% Traditional ROI: 2.74%
11611 N Charley Bluff Road Milton, WI Start your mornings with coffee on the front porch enjoying views of Lake Koshkonong! This...	3 beds \| 2 baths \| 2,094 sq.ft.	$375,500	Airbnb cash on cash: 2.04% Traditional cash on cash: 5.05% Airbnb Rental Income: $1937 Traditional Rental Income: $2488 Airbnb ROI: 2.04% Traditional ROI: 5.05%
1191 Red Hawk Dr Milton, WI Some homes just have a way of drawing you in. It might be the openness of the main living ...	3 beds \| 2 baths \| 1,736 sq.ft.	$534,900	Airbnb cash on cash: -0.17% Traditional cash on cash: 2% Airbnb Rental Income: $1937 Traditional Rental Income: $2508 Airbnb ROI: -0.17% Traditional ROI: 2%
56-58 E Ash Ln Milton, WI Brand-new duplex offering two modern 3-bedroom, 2-bath units with private entries and atta...	6 beds \| 4 baths \| N/A	$549,900	Airbnb cash on cash: 0.47% Traditional cash on cash: 3.03% Airbnb Rental Income: $1937 Traditional Rental Income: $2739 Airbnb ROI: 0.47% Traditional ROI: 3.03%
6641 N Kennedy Rd Milton, WI 3 beds/3 full baths in the main house, 1 bed/1 full bath in the separate 500 square foot g...	4 beds \| 4 baths \| 3,510 sq.ft.	$750,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 2.61% Airbnb Rental Income: $2538 Traditional Rental Income: $3768 Airbnb ROI: -0.02% Traditional ROI: 2.61%
68-70 E Ash Ln Milton, WI Brand~new duplex offering two modern 3~bedroom, 2~bath units with private entries and atta...	6 beds \| 4 baths \| N/A	$549,900	Airbnb cash on cash: 1.45% Traditional cash on cash: 3.03% Airbnb Rental Income: $2538 Traditional Rental Income: $2739 Airbnb ROI: 1.45% Traditional ROI: 3.03%
118-120 E Ash Ln Milton, WI Brand~new duplex offering two modern 3~bedroom, 2~bath units with private entries and atta...	6 beds \| 4 baths \| N/A	$549,900	Airbnb cash on cash: 1.45% Traditional cash on cash: 3.03% Airbnb Rental Income: $2538 Traditional Rental Income: $2739 Airbnb ROI: 1.45% Traditional ROI: 3.03%
602 E Madison Ave #35 Milton, WI Priced $40,000 Below Appraised Value! Come Home to instant equity with this New Luxury 202...	3 beds \| 3 baths \| 2,440 sq.ft.	$439,900	Airbnb cash on cash: 0.78% Traditional cash on cash: 4.49% Airbnb Rental Income: $1937 Traditional Rental Income: $2955 Airbnb ROI: 0.78% Traditional ROI: 4.49%
380 W Sunset Dr Milton, WI This beautiful maintained condo on Milton's Westside has been meticulously cared for. A ra...	4 beds \| 3 baths \| 2,362 sq.ft.	$379,900	Airbnb cash on cash: 2.88% Traditional cash on cash: 4.9% Airbnb Rental Income: $2538 Traditional Rental Income: $2647 Airbnb ROI: 2.88% Traditional ROI: 4.9%
183 Greenhill Cir Milton, WI $5,000 Closing Cost Credit for Buyers, buy down int. rate or use for closing costs! Welcom...	3 beds \| 2 baths \| 2,614 sq.ft.	$419,900	Airbnb cash on cash: 0.93% Traditional cash on cash: 5.15% Airbnb Rental Income: $1937 Traditional Rental Income: $3084 Airbnb ROI: 0.93% Traditional ROI: 5.15%
10721 N Bay Shore Ln Milton, WI You've waited YEARS for this one to come on the market! Bay Shore Condominium Estates END-...	2 beds \| 1 baths \| 1,278 sq.ft.	$350,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 3.01% Airbnb Rental Income: $1830 Traditional Rental Income: $2115 Airbnb ROI: 0.64% Traditional ROI: 3.01%
5524 E Kido Way Milton, WI 5524 E Kido Way, Milton, WI 53563 \| Single Family Residential	3 beds \| 2 baths \| 1,852 sq.ft.	$599,900	Airbnb cash on cash: -0.46% Traditional cash on cash: 1.02% Airbnb Rental Income: $1937 Traditional Rental Income: $2254 Airbnb ROI: -0.46% Traditional ROI: 1.02%
3506 Samson Dr Milton, WI 3506 Samson Dr, Milton, WI 53563 \| Single Family Residential	3 beds \| 2 baths \| 1,651 sq.ft.	$524,900	Airbnb cash on cash: -0.12% Traditional cash on cash: 1.17% Airbnb Rental Income: $1937 Traditional Rental Income: $2057 Airbnb ROI: -0.12% Traditional ROI: 1.17%
5510 E Kido Way Milton, WI 5510 E Kido Way, Milton, WI 53563 \| Single Family Residential	4 beds \| 2 baths \| 2,018 sq.ft.	$629,900	Airbnb cash on cash: 0.28% Traditional cash on cash: 1.01% Airbnb Rental Income: $2538 Traditional Rental Income: $2355 Airbnb ROI: 0.28% Traditional ROI: 1.01%
4.80 Acres M/L N Charley Bluff Rd Milton, WI 4.80 Acres M/L N Charley Bluff Rd, Milton, WI 53563 \| Other	N/A beds \| N/A baths \| N/A	$200,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.19% Airbnb Rental Income: $null Traditional Rental Income: $592 Airbnb ROI: N/A Traditional ROI: -0.19%
5 Acres M/L N Charley Bluff Rd Milton, WI 5 Acres M/L N Charley Bluff Rd, Milton, WI 53563 \| Other	N/A beds \| N/A baths \| N/A	$200,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.19% Airbnb Rental Income: $null Traditional Rental Income: $592 Airbnb ROI: N/A Traditional ROI: -0.19%
1107 Red Hawk Drive Milton, WI Welcome to effortless living in Red Hawk Farms in charming Milton. This thoughtfully desig...	2 beds \| 2 baths \| 1,262 sq.ft.	$329,900	Airbnb cash on cash: 1.15% Traditional cash on cash: 4.17% Airbnb Rental Income: $1830 Traditional Rental Income: $2271 Airbnb ROI: 1.15% Traditional ROI: 4.17%
1128 Crestline Drive Milton, WI Tastefully updated 5-bedroom ranch with walkout lower level, second kitchen, 3-car garage,...	5 beds \| 3 baths \| 2,404 sq.ft.	$479,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.09% Airbnb Rental Income: $null Traditional Rental Income: $2464 Airbnb ROI: N/A Traditional ROI: 3.09%
400 Woodcrest Ln Milton, WI Welcome home to this charming 1973 ranch, perfectly situated on a premier hilltop lot offe...	3 beds \| 1 baths \| 1,289 sq.ft.	$259,999	Airbnb cash on cash: 3.06% Traditional cash on cash: 2.47% Airbnb Rental Income: $1937 Traditional Rental Income: $1280 Airbnb ROI: 3.06% Traditional ROI: 2.47%
44 E Ash Ln Milton, WI 44 E Ash Ln, Milton, WI 53563 \| Single Family Residential	3 beds \| 1 baths \| 1,280 sq.ft.	$299,400	Airbnb cash on cash: 1.9% Traditional cash on cash: 1.41% Airbnb Rental Income: $1937 Traditional Rental Income: $1287 Airbnb ROI: 1.9% Traditional ROI: 1.41%
2716 Twelve Oaks Drive Milton, WI Custom quality and thoughtful updates define this beautifully maintained 3-bedroom, 3.5-ba...	3 beds \| 4 baths \| 3,120 sq.ft.	$519,900	Airbnb cash on cash: 0.49% Traditional cash on cash: 2.67% Airbnb Rental Income: $1937 Traditional Rental Income: $2486 Airbnb ROI: 0.49% Traditional ROI: 2.67%
5909 N Violet View Dr Milton, WI 5909 N Violet View Dr, Milton, WI 53563 \| Single Family Residential	5 beds \| 2 baths \| 2,600 sq.ft.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.22% Airbnb Rental Income: $null Traditional Rental Income: $1381 Airbnb ROI: N/A Traditional ROI: 0.22%
3486 Joshua Dr Milton, WI Estimated completion August 31st!! Beautiful new construction deigned by Urbancraft LLC fe...	3 beds \| 2 baths \| 1,937 sq.ft.	$650,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 2.53% Airbnb Rental Income: $1937 Traditional Rental Income: $2276 Airbnb ROI: 1.12% Traditional ROI: 2.53%
10519 N Otter Creek Rd Milton, WI 10519 N Otter Creek Rd, Milton, WI 53563 \| Other	N/A beds \| N/A baths \| N/A	$134,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.05% Airbnb Rental Income: $null Traditional Rental Income: $593 Airbnb ROI: N/A Traditional ROI: 1.05%
L2 Vincent St Milton, WI L2 Vincent St, Milton, WI 53563 \| Other	N/A beds \| N/A baths \| N/A	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: -0.18% Airbnb Rental Income: $null Traditional Rental Income: $593 Airbnb ROI: N/A Traditional ROI: -0.18%

Real Estate investment in Milton, WI

There are 77 properties for sale in the city of Milton . The median list price in Milton is $394,264 and the average price per square foot is $194. In August 2026, the average monthly cash on cash return in Milton is 3.00%. The average monthly rental income in Milton is $2,269.

Milton, WI Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 77 investment properties available for sale in Milton.

In 2026, the best neighborhood to buy investment property is Milton.

The ROI for Long-Term is higher than the Short-Term in Milton with average rental income of $2,269.

Your search for investment property begins and ends here

Investment Property for Sale in Milton, WI

Lot 60 Lakeside Dr

Milton, WI

N/A beds | N/A baths | N/A

$184,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.1%

Airbnb Rental Income: $null

Traditional Rental Income: $801

Airbnb ROI: N/A

Traditional ROI: 1.1%

Lot 10 Kido Way

Milton, WI

N/A beds | N/A baths | N/A

$254,900

Airbnb cash on cash: N/A

Traditional cash on cash: -0.75%

Airbnb Rental Income: $null

Traditional Rental Income: $593

Airbnb ROI: N/A

Traditional ROI: -0.75%

3496 Pickard Dr

Milton, WI

3 beds | 2 baths | 2,760 sq.ft.

$429,900

Airbnb cash on cash: 1.29%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $1937

Traditional Rental Income: $2589

Airbnb ROI: 1.29%

Traditional ROI: 4.18%

323 S John Paul Rd

Milton, WI

2 beds | 1 baths | 720 sq.ft.

$265,000

Airbnb cash on cash: 3.4%

Traditional cash on cash: 2.41%

Airbnb Rental Income: $1830

Traditional Rental Income: $1087

Airbnb ROI: 3.4%

Traditional ROI: 2.41%

101 N Clear Lake Ave

Milton, WI

4 beds | 2 baths | 2,400 sq.ft.

$375,000

Airbnb cash on cash: 3.28%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $2538

Traditional Rental Income: $2146

Airbnb ROI: 3.28%

Traditional ROI: 3.9%

7938 E Highway 59

Milton, WI

3 beds | 3 baths | 2,536 sq.ft.

$720,000

Airbnb cash on cash: 0.11%

Traditional cash on cash: 2.36%

Airbnb Rental Income: $1937

Traditional Rental Income: $2936

Airbnb ROI: 0.11%

Traditional ROI: 2.36%

2309 E Pine Tree Ct

Milton, WI

4 beds | 3 baths | 3,196 sq.ft.

$609,000

Airbnb cash on cash: 1.2%

Traditional cash on cash: 3.93%

Airbnb Rental Income: $2538

Traditional Rental Income: $3477

Airbnb ROI: 1.2%

Traditional ROI: 3.93%

3537 Samson Dr

Milton, WI

3 beds | 2 baths | 2,017 sq.ft.

$559,900

Airbnb cash on cash: 1.5%

Traditional cash on cash: 4.3%

Airbnb Rental Income: $1937

Traditional Rental Income: $2890

Airbnb ROI: 1.5%