Real Estate Investment Properties for Sale in Wilmington, VT

Looking for investment property in Wilmington, VT with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
28 Lightning Ledge Way Wilmington, VT Owners will consider reasonable offers. Private 2004 country chalet in the Chimney Hill co...	3 beds \| 3 baths \| 1,548 sq.ft.	$439,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 4.73% Airbnb Rental Income: $1676 Traditional Rental Income: $3139 Airbnb ROI: 0.03% Traditional ROI: 4.73%
152 Lake Raponda Road Wilmington, VT Enjoy four season living from this spacious lake home just off Lake Raponda in Wilmington ...	5 beds \| 4 baths \| 5,757 sq.ft.	$1,997,000	Airbnb cash on cash: -1.15% Traditional cash on cash: 1.33% Airbnb Rental Income: $2049 Traditional Rental Income: $6104 Airbnb ROI: -1.15% Traditional ROI: 1.33%
21 Big Bend Loop Wilmington, VT Welcome to 21 Big Bend Loop in Wilmington, VT, where mountain charm, year-round adventure,...	3 beds \| 2 baths \| 1,586 sq.ft.	$325,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 6.64% Airbnb Rental Income: $1676 Traditional Rental Income: $3015 Airbnb ROI: 0.72% Traditional ROI: 6.64%
15 Haymaker Lane #6D Wilmington, VT Beautiful condo on the side of Haystack mountain at the beautiful exclusive Hermitage Club...	2 beds \| 3 baths \| 1,429 sq.ft.	$449,000	Airbnb cash on cash: -2.69% Traditional cash on cash: 3.34% Airbnb Rental Income: $1041 Traditional Rental Income: $3215 Airbnb ROI: -2.69% Traditional ROI: 3.34%
9 Greer Court Wilmington, VT Charming 2007 home with recent renovations nestled in the Chimney Hill community just a sh...	3 beds \| 3 baths \| 2,080 sq.ft.	$575,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 3.31% Airbnb Rental Income: $1676 Traditional Rental Income: $3397 Airbnb ROI: -0.77% Traditional ROI: 3.31%
11 Dutchman Lane #4A Wilmington, VT Beautiful three story Powderhorn townhome on the slopes of Haystack Mountain at the exclus...	3 beds \| 3 baths \| 1,948 sq.ft.	$499,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 3.87% Airbnb Rental Income: $1676 Traditional Rental Income: $3541 Airbnb ROI: -1.13% Traditional ROI: 3.87%
49 West Road Wilmington, VT Lovely renovated chalet at the bottom of the Chimney Hill community with easy access to tr...	3 beds \| 2 baths \| 1,510 sq.ft.	$425,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 4.81% Airbnb Rental Income: $1676 Traditional Rental Income: $3065 Airbnb ROI: 0.14% Traditional ROI: 4.81%
37 Stowe Hill Road Wilmington, VT Welcome to Spruce Hill Farm, circa 1890, a beautifully restored farmhouse set on 47.7 pict...	4 beds \| 3 baths \| 2,904 sq.ft.	$624,900	Airbnb cash on cash: -1.06% Traditional cash on cash: -0.87% Airbnb Rental Income: $1643 Traditional Rental Income: $1289 Airbnb ROI: -1.06% Traditional ROI: -0.87%
21 Lawrence Davis Drive Wilmington, VT NEW 2025 MANUFACTURED HOME ON 1.4 ACRES IN WILMINGTON! Enjoy the perfect blend of privacy,...	3 beds \| 2 baths \| 1,296 sq.ft.	$299,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 1.45% Airbnb Rental Income: $1676 Traditional Rental Income: $1289 Airbnb ROI: 1.16% Traditional ROI: 1.45%
33 W Main Street Wilmington, VT Unique opportunity to own a commercial building in the heart of downtown Wilmington. This ...	1 beds \| 3 baths \| 2,076 sq.ft.	$425,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 4.96% Airbnb Rental Income: $964 Traditional Rental Income: $2900 Airbnb ROI: -0.78% Traditional ROI: 4.96%
511 Shearer Hill Road Wilmington, VT A rare opportunity to own 95+ acres in the heart of Southern Vermont with a beautiful post...	5 beds \| 3 baths \| 2,415 sq.ft.	$900,000	Airbnb cash on cash: -1.05% Traditional cash on cash: 1.87% Airbnb Rental Income: $2049 Traditional Rental Income: $3971 Airbnb ROI: -1.05% Traditional ROI: 1.87%
6 Church Street Wilmington, VT Located in the heart of Wilmington, this charming two bedroom, one and a half bath home of...	2 beds \| 2 baths \| 2,184 sq.ft.	$239,900	Airbnb cash on cash: -0.28% Traditional cash on cash: 9.05% Airbnb Rental Income: $1041 Traditional Rental Income: $2793 Airbnb ROI: -0.28% Traditional ROI: 9.05%
48 High Top Road #B130 Wilmington, VT This is IT! Section B double Lot at the end of the Road! Renovated inside and out. expande...	3 beds \| 2 baths \| 1,885 sq.ft.	$679,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 2.77% Airbnb Rental Income: $1676 Traditional Rental Income: $3137 Airbnb ROI: -0.28% Traditional ROI: 2.77%
60 East Brook Crossing #C-201 Wilmington, VT This gem is tucked away in the quiet Section C part of the super popular Chimney Hill, HOA...	3 beds \| 2 baths \| 1,450 sq.ft.	$349,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 6.57% Airbnb Rental Income: $1676 Traditional Rental Income: $2969 Airbnb ROI: 1.2% Traditional ROI: 6.57%
90 Big Bend Loop Wilmington, VT Stunning updated and expanded chalet just a short drive out of the village of Wilmington. ...	4 beds \| 3 baths \| 2,352 sq.ft.	$599,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 0.93% Airbnb Rental Income: $1643 Traditional Rental Income: $1856 Airbnb ROI: -0.28% Traditional ROI: 0.93%
19 View Road Wilmington, VT Come take a look at this three bedroom and two bath chalet in the B Section of Chimney Hil...	3 beds \| 2 baths \| 1,400 sq.ft.	$335,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 6.46% Airbnb Rental Income: $1676 Traditional Rental Income: $2869 Airbnb ROI: 1.19% Traditional ROI: 6.46%
3 Valley View Wilmington, VT Beautiful renovated chalet in the Chimney Hill community just a short drive from Mount Sno...	3 beds \| 2 baths \| 1,655 sq.ft.	$539,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 3.79% Airbnb Rental Income: $1676 Traditional Rental Income: $3022 Airbnb ROI: 0.19% Traditional ROI: 3.79%
12 Three Streams Way #A-11 Wilmington, VT In a quiet lower corner of the Hill, is this special offering in Section A. The quality is...	3 beds \| 3 baths \| 2,340 sq.ft.	$699,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 3.38% Airbnb Rental Income: $1676 Traditional Rental Income: $3625 Airbnb ROI: -0.32% Traditional ROI: 3.38%
6 South Main Street Wilmington, VT A unique and historic building in the heart of downtown Wilmington VT. Originally built in...	N/A beds \| N/A baths \| 2,905 sq.ft.	$479,000	Airbnb cash on cash: -1.34% Traditional cash on cash: 1.18% Airbnb Rental Income: $1169 Traditional Rental Income: $1913 Airbnb ROI: -1.34% Traditional ROI: 1.18%

Real Estate investment in Wilmington, VT

There are 24 properties for sale in the city of Wilmington . The median list price in Wilmington is $734,560 and the average price per square foot is $300. In November 2026, the average monthly cash on cash return in Wilmington is 3.00%. The average monthly rental income in Wilmington is $2,793.

Wilmington, VT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 24 investment properties available for sale in Wilmington.

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

The ROI for Short-Term is higher than the Long-Term in Wilmington with average rental income of $1,643.

Your search for investment property begins and ends here

Investment Property for Sale in Wilmington, VT

28 Lightning Ledge Way

Wilmington, VT

3 beds | 3 baths | 1,548 sq.ft.

$439,000

Airbnb cash on cash: 0.03%

Traditional cash on cash: 4.73%

Airbnb Rental Income: $1676

Traditional Rental Income: $3139

Airbnb ROI: 0.03%

Traditional ROI: 4.73%

152 Lake Raponda Road

Wilmington, VT

5 beds | 4 baths | 5,757 sq.ft.

$1,997,000

Airbnb cash on cash: -1.15%

Traditional cash on cash: 1.33%

Airbnb Rental Income: $2049

Traditional Rental Income: $6104

Airbnb ROI: -1.15%

Traditional ROI: 1.33%

21 Big Bend Loop

Wilmington, VT

3 beds | 2 baths | 1,586 sq.ft.

$325,000

Airbnb cash on cash: 0.72%

Traditional cash on cash: 6.64%

Airbnb Rental Income: $1676

Traditional Rental Income: $3015

Airbnb ROI: 0.72%

Traditional ROI: 6.64%

15 Haymaker Lane #6D

Wilmington, VT

2 beds | 3 baths | 1,429 sq.ft.

$449,000

Airbnb cash on cash: -2.69%

Traditional cash on cash: 3.34%

Airbnb Rental Income: $1041

Traditional Rental Income: $3215

Airbnb ROI: -2.69%

Traditional ROI: 3.34%

9 Greer Court

Wilmington, VT

3 beds | 3 baths | 2,080 sq.ft.

$575,000

Airbnb cash on cash: -0.77%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $1676

Traditional Rental Income: $3397

Airbnb ROI: -0.77%

Traditional ROI: 3.31%

11 Dutchman Lane #4A

Wilmington, VT

3 beds | 3 baths | 1,948 sq.ft.

$499,000

Airbnb cash on cash: -1.13%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $1676

Traditional Rental Income: $3541

Airbnb ROI: -1.13%

Traditional ROI: 3.87%

49 West Road

Wilmington, VT

3 beds | 2 baths | 1,510 sq.ft.

$425,000

Airbnb cash on cash: 0.14%

Traditional cash on cash: 4.81%

Airbnb Rental Income: $1676

Traditional Rental Income: $3065

Airbnb ROI: 0.14%

Traditional ROI: 4.81%

37 Stowe Hill Road

Wilmington, VT

4 beds | 3 baths | 2,904 sq.ft.

$624,900

Airbnb cash on cash: -1.06%

Traditional cash on cash: -0.87%

Airbnb Rental Income: $1643

Traditional Rental Income: $1289

Airbnb ROI: -1.06%