Real Estate Investment Properties for Sale in Winchester, WI

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

Explore a variety of short-term homes & houses in Winchester, WI. Invest wisely with VRBO & Winchester, 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 Winchester, WI

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
7510 County Road W Winchester, WI Discover the ultimate private retreat w/325 feet of pristine sand frontage on the serene T...	2 beds \| 1 baths \| 1,227 sq.ft.	$949,900	Airbnb cash on cash: 0.76% Traditional cash on cash: 1.31% Airbnb Rental Income: $2447 Traditional Rental Income: $2332 Airbnb ROI: 0.76% Traditional ROI: 1.31%
13107 VILLAGE POINT LN #6 - Pine Winchester, WI Care-free second home plus wise investment. Only 7 units in this congenial, care-free, sta...	2 beds \| 2 baths \| 1,119 sq.ft.	$399,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 3.96% Airbnb Rental Income: $2447 Traditional Rental Income: $2086 Airbnb ROI: 3.33% Traditional ROI: 3.96%
8688 ROCK LAKE RD W Winchester, WI Beautiful full log home on the Turtle Winchester Chain of Lakes! Lovely home is situated o...	3 beds \| 2 baths \| 1,847 sq.ft.	$819,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 2.25% Airbnb Rental Income: $2911 Traditional Rental Income: $2838 Airbnb ROI: 1.46% Traditional ROI: 2.25%
Investment Properties for Sale in Other Cities of Wisconsin
929 Spyglass Hl Waterford , WI This custom, side-by-side ranch-style condo shows like new and offers an open-concept desi...	2 beds \| 2 baths \| 1,676 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.14% Airbnb Rental Income: $null Traditional Rental Income: $2646 Airbnb ROI: N/A Traditional ROI: 4.14%
915 S 109th St West Allis , WI This beautifully updated 3-bedroom, 1-bathroom home offers a blend of modern comfort and c...	3 beds \| 1 baths \| 937 sq.ft.	$225,000	Airbnb cash on cash: 8.22% Traditional cash on cash: 4.21% Airbnb Rental Income: $3049 Traditional Rental Income: $1497 Airbnb ROI: 8.22% Traditional ROI: 4.21%
W1281 Siena Circle Lake Geneva , WI Tuscany subdivision home on 5 acres with beautiful views in all directions - nice land wit...	4 beds \| 4 baths \| 4,270 sq.ft.	$910,000	Airbnb cash on cash: 3.99% Traditional cash on cash: 2% Airbnb Rental Income: $6650 Traditional Rental Income: $3664 Airbnb ROI: 3.99% Traditional ROI: 2%
10812 W Fiebrantz Ave Wauwatosa , WI Discover your dream home in this charming 4-bedroom, 2-bath residence, where comfort meets...	4 beds \| 2 baths \| 1,524 sq.ft.	$349,900	Airbnb cash on cash: 5.71% Traditional cash on cash: 4.34% Airbnb Rental Income: $3539 Traditional Rental Income: $2307 Airbnb ROI: 5.71% Traditional ROI: 4.34%
W178n5183 Roseway Ave Menomonee Falls , WI This Hamilton School District tri-level has been wonderfully updated and maintained. The i...	3 beds \| 2 baths \| 1,994 sq.ft.	$424,900	Airbnb cash on cash: 2.13% Traditional cash on cash: 4.1% Airbnb Rental Income: $2280 Traditional Rental Income: $2498 Airbnb ROI: 2.13% Traditional ROI: 4.1%
2832 N 61st St Milwaukee , WI AMAZING!!!! COME TAKE A TOUR OF THIS 4 BED, 2 FULL BATH HOME!!! THIS HOME IS FILLED WITH S...	4 beds \| 2 baths \| 1,749 sq.ft.	$238,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.64% Airbnb Rental Income: $null Traditional Rental Income: $1188 Airbnb ROI: N/A Traditional ROI: 2.64%
4260 N 26th St Milwaukee , WI Welcome to this renovated bungalow in the Rufus King neighborhood! This home has been thou...	3 beds \| 1 baths \| 1,428 sq.ft.	$185,000	Airbnb cash on cash: 6.25% Traditional cash on cash: 7.15% Airbnb Rental Income: $2050 Traditional Rental Income: $1679 Airbnb ROI: 6.25% Traditional ROI: 7.15%
3056 S 41st St Milwaukee , WI Welcome to this sensational Jackson Park Lannon Stone colonial! Living room boasts a beau...	3 beds \| 3 baths \| 2,118 sq.ft.	$374,900	Airbnb cash on cash: 2.16% Traditional cash on cash: 5.35% Airbnb Rental Income: $2333 Traditional Rental Income: $2878 Airbnb ROI: 2.16% Traditional ROI: 5.35%
4024 N 44th St Milwaukee , WI Discover this charming 3-bedroom, 1.5-bathroom cape cod home, beautifully rehabbed in 2021...	3 beds \| 2 baths \| 1,366 sq.ft.	$164,500	Airbnb cash on cash: 6.09% Traditional cash on cash: 10.86% Airbnb Rental Income: $1884 Traditional Rental Income: $2130 Airbnb ROI: 6.09% Traditional ROI: 10.86%
2080 N Commerce St #101 Milwaukee , WI This modern southwest facing corner condo offers a blend of urban convenience and stylish ...	2 beds \| 2 baths \| 995 sq.ft.	$235,000	Airbnb cash on cash: 5.32% Traditional cash on cash: 5.35% Airbnb Rental Income: $2430 Traditional Rental Income: $1843 Airbnb ROI: 5.32% Traditional ROI: 5.35%
4609 Gordon Avenue Monona , WI Good things come in small packages! This charming single-level Monona home is ready and wa...	2 beds \| 1 baths \| 792 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.11% Airbnb Rental Income: $null Traditional Rental Income: $1309 Airbnb ROI: N/A Traditional ROI: 2.11%
3027 Providence Street #2 Sun Prairie , WI This charming end unit 2 bed, 2.5 bath condo close to it all has everything you're looking...	2 beds \| 3 baths \| 1,620 sq.ft.	$275,000	Airbnb cash on cash: 9.48% Traditional cash on cash: 5.56% Airbnb Rental Income: $4068 Traditional Rental Income: $2185 Airbnb ROI: 9.48% Traditional ROI: 5.56%
1105 Artisan Drive Madison , WI This thoughtfully updated 4-bedroom, 2-bathroom home has been completely transformed! Near...	4 beds \| 2 baths \| 2,049 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.97% Airbnb Rental Income: $null Traditional Rental Income: $2511 Airbnb ROI: N/A Traditional ROI: 3.97%
205 N 4th Street Mount Horeb , WI A yard this size is a RARE FIND! Come explore this beautiful 3 bdrm, 2 bath home which fea...	3 beds \| 2 baths \| 1,725 sq.ft.	$369,000	Airbnb cash on cash: 9.62% Traditional cash on cash: 4.16% Airbnb Rental Income: $5236 Traditional Rental Income: $2281 Airbnb ROI: 9.62% Traditional ROI: 4.16%
1532 Hazeltine Drive Eau Claire , WI This ranch home combines comfort and style. As you step inside, you'll be greeted by an ab...	3 beds \| 2 baths \| 2,000 sq.ft.	$329,900	Airbnb cash on cash: 1.32% Traditional cash on cash: 5.8% Airbnb Rental Income: $1673 Traditional Rental Income: $2592 Airbnb ROI: 1.32% Traditional ROI: 5.8%

Real Estate investment in Winchester, WI

There are 4 properties for sale in the city of Winchester . The median list price in Winchester is $819,000 and the average price per square foot is $586. In November 2024, the average monthly cash on cash return in Winchester is 2.00%. The average monthly rental income in Winchester is $2,332.

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

There are 4 investment properties available for sale in Winchester.

In 2024, the best neighborhood to buy investment property is Winchester.

The ROI for Long-Term is higher than the Short-Term in Winchester with average rental income of $2,332.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, WI

7510 County Road W

Winchester, WI

2 beds | 1 baths | 1,227 sq.ft.

$949,900

Airbnb cash on cash: 0.76%

Traditional cash on cash: 1.31%

Airbnb Rental Income: $2447

Traditional Rental Income: $2332

Airbnb ROI: 0.76%

Traditional ROI: 1.31%

13107 VILLAGE POINT LN #6 - Pine

Winchester, WI

2 beds | 2 baths | 1,119 sq.ft.

$399,000

Airbnb cash on cash: 3.33%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $2447

Traditional Rental Income: $2086

Airbnb ROI: 3.33%

Traditional ROI: 3.96%

8688 ROCK LAKE RD W

Winchester, WI

3 beds | 2 baths | 1,847 sq.ft.

$819,000

Airbnb cash on cash: 1.46%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $2911

Traditional Rental Income: $2838

Airbnb ROI: 1.46%

Traditional ROI: 2.25%

Investment Properties for Sale in Other Cities of Wisconsin

Waterford , WI

2 beds | 2 baths | 1,676 sq.ft.

$429,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.14%

Airbnb Rental Income: $null

Traditional Rental Income: $2646

Airbnb ROI: N/A

Traditional ROI: 4.14%

West Allis , WI

3 beds | 1 baths | 937 sq.ft.

$225,000

Airbnb cash on cash: 8.22%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $3049

Traditional Rental Income: $1497

Airbnb ROI: 8.22%

Traditional ROI: 4.21%

Lake Geneva , WI

4 beds | 4 baths | 4,270 sq.ft.

$910,000

Airbnb cash on cash: 3.99%

Traditional cash on cash: 2%

Airbnb Rental Income: $6650

Traditional Rental Income: $3664

Airbnb ROI: 3.99%

Traditional ROI: 2%

Wauwatosa , WI

4 beds | 2 baths | 1,524 sq.ft.

$349,900

Airbnb cash on cash: 5.71%

Traditional cash on cash: 4.34%

Airbnb Rental Income: $3539

Traditional Rental Income: $2307

Airbnb ROI: 5.71%

Traditional ROI: 4.34%

Menomonee Falls , WI

3 beds | 2 baths | 1,994 sq.ft.

$424,900

Airbnb cash on cash: 2.13%

Traditional cash on cash: 4.1%

Airbnb Rental Income: $2280

Traditional Rental Income: $2498

Airbnb ROI: 2.13%

Traditional ROI: 4.1%

Milwaukee , WI

4 beds | 2 baths | 1,749 sq.ft.

$238,000