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
195 Mann Rd #12 Wilmington, VT Beautifully positioned along the 11th fairway of the Haystack Golf Course, this contempora...	3 beds \| 3 baths \| 2,814 sq.ft.	$425,000	Airbnb cash on cash: -1.83% Traditional cash on cash: 6.28% Airbnb Rental Income: $1685 Traditional Rental Income: $4443 Airbnb ROI: -1.83% Traditional ROI: 6.28%
156 W Lake Rd Wilmington, VT A rare opportunity to own a beautifully maintained, one-family-owned home on Lake Raponda....	3 beds \| 4 baths \| 2,944 sq.ft.	$1,300,000	Airbnb cash on cash: -1.29% Traditional cash on cash: 1.64% Airbnb Rental Income: $1685 Traditional Rental Income: $4752 Airbnb ROI: -1.29% Traditional ROI: 1.64%
41 Two Brook Dr Wilmington, VT Fantastic four-season upscale 4bdrm/5 bath home just minutes from Hermitage Club, Mount Sn...	4 beds \| 3 baths \| 3,420 sq.ft.	$898,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 5.54% Airbnb Rental Income: $1976 Traditional Rental Income: $6604 Airbnb ROI: -0.62% Traditional ROI: 5.54%
28 Lightning Ledge Way Wilmington, VT Private 2004 country chalet in the Chimney Hill community just outside the village of Wilm...	3 beds \| 2 baths \| 1,548 sq.ft.	$474,900	Airbnb cash on cash: -0.03% Traditional cash on cash: 4.3% Airbnb Rental Income: $1685 Traditional Rental Income: $3139 Airbnb ROI: -0.03% Traditional ROI: 4.3%
68 E Brook Xing Wilmington, VT Lovely updated chalet in the Chimney Hill community just outside the village of Wilmington...	3 beds \| 2 baths \| 1,472 sq.ft.	$425,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 4.88% Airbnb Rental Income: $1685 Traditional Rental Income: $2944 Airbnb ROI: 0.54% Traditional ROI: 4.88%
16 Tenth Ln #40 Wilmington, VT Beautiful 4 bedroom, 3.5 bath townhouse just off the Hermitage Club Golf Course with easy ...	4 beds \| 3 baths \| 1,800 sq.ft.	$450,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 5.87% Airbnb Rental Income: $1976 Traditional Rental Income: $4089 Airbnb ROI: -0.38% Traditional ROI: 5.87%
197 Lake Raponda Road Wilmington, VT This vintage renovated waterfront home is being offered for the second time in 40 years. L...	4 beds \| 3 baths \| 2,420 sq.ft.	$1,697,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 0.62% Airbnb Rental Income: $1976 Traditional Rental Income: $3977 Airbnb ROI: -0.98% Traditional ROI: 0.62%
34 Binney Brook Rd Wilmington, VT Beautiful upscale chalet in the Chimney Hill community just a short drive from the Mount S...	4 beds \| 3 baths \| 2,516 sq.ft.	$675,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 2.57% Airbnb Rental Income: $1976 Traditional Rental Income: $3121 Airbnb ROI: -0.07% Traditional ROI: 2.57%
5 First Ln #1 Wilmington, VT Owner open to offers. Lovely 2 bedroom condo as close as you can get to the 1st tee at the...	2 beds \| 2 baths \| 1,000 sq.ft.	$305,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 8.58% Airbnb Rental Income: $1418 Traditional Rental Income: $3660 Airbnb ROI: -0.71% Traditional ROI: 8.58%
29 Mountain Ridge Dr Wilmington, VT The Mountain Ridge community is newly developed and this is the first opportunity to enter...	5 beds \| 4 baths \| 7,000 sq.ft.	$3,500,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 0.04% Airbnb Rental Income: $3067 Traditional Rental Income: $5287 Airbnb ROI: -0.86% Traditional ROI: 0.04%
100 Mowing Way Wilmington, VT This immaculately maintained home is located on the 3rd hole of Haystack Golf Course. A l...	5 beds \| 3 baths \| 3,015 sq.ft.	$879,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 2.18% Airbnb Rental Income: $3067 Traditional Rental Income: $3457 Airbnb ROI: 0.84% Traditional ROI: 2.18%
67 Castle Hill Rd Wilmington, VT Rare opportunity to own a meticulously restored 1830s vintage farmhouse, offered completel...	5 beds \| 3 baths \| 3,436 sq.ft.	$849,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 3.38% Airbnb Rental Income: $3067 Traditional Rental Income: $4406 Airbnb ROI: 0.8% Traditional ROI: 3.38%
47 Ives Rd Wilmington, VT Unique spacious log home near the Hermitage Ski Club with easy access to the resort, direc...	5 beds \| 3 baths \| 2,240 sq.ft.	$499,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 6.85% Airbnb Rental Income: $3067 Traditional Rental Income: $4304 Airbnb ROI: 2.7% Traditional ROI: 6.85%
5 N Main St Wilmington, VT Located in the heart of downtown Wilmington and just minutes from Mount Snow and Harriman ...	3 beds \| 3 baths \| 4,219 sq.ft.	$725,000	Airbnb cash on cash: 0% Traditional cash on cash: 5.27% Airbnb Rental Income: $1685 Traditional Rental Income: $4780 Airbnb ROI: 0% Traditional ROI: 5.27%
156 Mountain View Rd Wilmington, VT This charming Cape-style home offers three bedrooms and two full baths across the first tw...	3 beds \| 2 baths \| 1,300 sq.ft.	$429,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 4.42% Airbnb Rental Income: $1685 Traditional Rental Income: $2733 Airbnb ROI: 0.65% Traditional ROI: 4.42%
15 Haymaker Ln #6D Wilmington, VT Beautiful condo on the side of Haystack mountain at the beautiful exclusive Hermitage Club...	2 beds \| 2 baths \| 1,912 sq.ft.	$469,000	Airbnb cash on cash: -1.64% Traditional cash on cash: 3.43% Airbnb Rental Income: $1418 Traditional Rental Income: $3215 Airbnb ROI: -1.64% Traditional ROI: 3.43%
32 Steep Hill Rd Wilmington, VT Private Vermont Sanctuary with Spectacular Mountain Views. Tucked away on a quiet dead-end...	5 beds \| 4 baths \| 4,200 sq.ft.	$2,195,000	Airbnb cash on cash: -1.78% Traditional cash on cash: 0.35% Airbnb Rental Income: $3067 Traditional Rental Income: $6692 Airbnb ROI: -1.78% Traditional ROI: 0.35%
29 First Ln #17 Wilmington, VT Enjoy Green Mountain views from this bright and spacious end-unit townhouse, perfectly sit...	4 beds \| 3 baths \| 2,015 sq.ft.	$437,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 6.37% Airbnb Rental Income: $1976 Traditional Rental Income: $4265 Airbnb ROI: -0.49% Traditional ROI: 6.37%
9 Greer Ct 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.	$559,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 3.65% Airbnb Rental Income: $1685 Traditional Rental Income: $3397 Airbnb ROI: -0.52% Traditional ROI: 3.65%
14 Tarheel Trl Wilmington, VT This custom built 2018 log home, designed by RH Log Works and Hilderbrand Interiors, offer...	5 beds \| 4 baths \| 5,110 sq.ft.	$1,999,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 1.66% Airbnb Rental Income: $3067 Traditional Rental Income: $6523 Airbnb ROI: -0.58% Traditional ROI: 1.66%
11 Dutchman Ln #4A Wilmington, VT This 3-bedroom plus loft, 2.5-bath end unit townhouse is in Powderhorn Village. The entran...	3 beds \| 2 baths \| 2,044 sq.ft.	$529,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 3.91% Airbnb Rental Income: $1685 Traditional Rental Income: $3541 Airbnb ROI: -0.79% Traditional ROI: 3.91%
49 West Rd 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.	$449,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 4.58% Airbnb Rental Income: $1685 Traditional Rental Income: $3065 Airbnb ROI: 0.18% Traditional ROI: 4.58%
12 Three Streams Way Wilmington, VT Beautiful 2006 chalet in the Chimney Hill community just a short drive from the Mount Snow...	3 beds \| 3 baths \| 2,216 sq.ft.	$675,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 3.12% Airbnb Rental Income: $1685 Traditional Rental Income: $3493 Airbnb ROI: -0.5% Traditional ROI: 3.12%
8 Little Bnd #M-175 Wilmington, VT Time to start living the dream with your very own getaway in Chimney Hill! Little Bend Hav...	4 beds \| 2 baths \| 1,900 sq.ft.	$449,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 6.1% Airbnb Rental Income: $1976 Traditional Rental Income: $3660 Airbnb ROI: 0.87% Traditional ROI: 6.1%
18 New England Power Rd Wilmington, VT This extraordinary luxury farmhouse has been masterfully remodeled by the current owners, ...	5 beds \| 5 baths \| 5,500 sq.ft.	$2,150,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 1.49% Airbnb Rental Income: $3067 Traditional Rental Income: $6495 Airbnb ROI: -0.58% Traditional ROI: 1.49%
216 Ghastly Job Way Wilmington, VT Vermont mountain getaway perched on a private parcel at the end of a quiet country road, t...	3 beds \| 2 baths \| 1,920 sq.ft.	$474,900	Airbnb cash on cash: 0.27% Traditional cash on cash: 4.75% Airbnb Rental Income: $1685 Traditional Rental Income: $3208 Airbnb ROI: 0.27% Traditional ROI: 4.75%
29 Stable Rd Wilmington, VT The Stable Lodge was built in 1969-1970. Located near Haystack Ski Area and Golf Course a...	2 beds \| N/A baths \| 2,710 sq.ft.	$199,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 9.6% Airbnb Rental Income: $1418 Traditional Rental Income: $2270 Airbnb ROI: 2.84% Traditional ROI: 9.6%
555 VT route 9 Wilmington, VT MOTIVATED SELLER WITH A NEW PRICE IMPROVEMENT! This brand-new construction, three-bedroom,...	3 beds \| 2 baths \| 1,850 sq.ft.	$519,990	Airbnb cash on cash: -0.62% Traditional cash on cash: 3.72% Airbnb Rental Income: $1685 Traditional Rental Income: $3363 Airbnb ROI: -0.62% Traditional ROI: 3.72%
457 Ray Hill Rd Wilmington, VT Lovely expanded farmhouse just up from the village of Wilmington and with mountain views a...	3 beds \| 2 baths \| 1,874 sq.ft.	$649,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 3.43% Airbnb Rental Income: $1685 Traditional Rental Income: $3410 Airbnb ROI: -0.2% Traditional ROI: 3.43%
12 Lilla Ln Wilmington, VT Beautiful woodsy contemporary chalet located just down from the Chimney Hill Clubhouse in ...	3 beds \| 2 baths \| 2,003 sq.ft.	$489,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 4.53% Airbnb Rental Income: $1685 Traditional Rental Income: $3196 Airbnb ROI: 0.2% Traditional ROI: 4.53%
286 Coldbrook Rd Wilmington, VT This new construction home is located in one of Southern Vermont's most desirable four sea...	4 beds \| 4 baths \| 3,844 sq.ft.	$1,400,000	Airbnb cash on cash: -1.84% Traditional cash on cash: 0.39% Airbnb Rental Income: $1976 Traditional Rental Income: $4362 Airbnb ROI: -1.84% Traditional ROI: 0.39%
247 VT Route 100 Wilmington, VT Conveniently located on Route 100 between Wilmington Village and Mount Snow. Two separate ...	6 beds \| 2 baths \| 1,920 sq.ft.	$379,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 7.43% Airbnb Rental Income: $3067 Traditional Rental Income: $3305 Airbnb ROI: 4.79% Traditional ROI: 7.43%
197 Lake Raponda Rd Wilmington, VT This vintage renovated waterfront home is being offered for the second time in 40 years. L...	4 beds \| 3 baths \| 2,420 sq.ft.	$1,697,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 0.95% Airbnb Rental Income: $1976 Traditional Rental Income: $3718 Airbnb ROI: -0.48% Traditional ROI: 0.95%
1 Frog Holw Wilmington, VT Charming Rustic Country Saltbox on Lower Chimney Hill Nestled in a convenient Lower Chimne...	3 beds \| 2 baths \| 1,200 sq.ft.	$389,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 4.79% Airbnb Rental Income: $1685 Traditional Rental Income: $2684 Airbnb ROI: 0.76% Traditional ROI: 4.79%
33 W Main St Wilmington, VT Unique opportunity to own a commercial building in the heart of downtown Wilmington. This ...	1 beds \| 2 baths \| 2,076 sq.ft.	$459,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 4.56% Airbnb Rental Income: $1150 Traditional Rental Income: $2900 Airbnb ROI: -0.4% Traditional ROI: 4.56%
26 N Wind Rd Wilmington, VT Rustic Country Home This inviting rustic country home features a spacious great room with...	3 beds \| 3 baths \| 2,690 sq.ft.	$429,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 1.72% Airbnb Rental Income: $1685 Traditional Rental Income: $1680 Airbnb ROI: 0.56% Traditional ROI: 1.72%
117 Ray Hill Rd Wilmington, VT 117 Ray Hill Rd, Wilmington, VT 05363 \| Single Family Residential	3 beds \| 2 baths \| 1,410 sq.ft.	$529,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 2.49% Airbnb Rental Income: $1685 Traditional Rental Income: $2753 Airbnb ROI: -0.62% Traditional ROI: 2.49%
798 Vermont Route 100 Wilmington, VT 798 Vermont Route 100, Wilmington, VT 05363 \| Single Family Residential	5 beds \| 3 baths \| 3,091 sq.ft.	$799,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 2.51% Airbnb Rental Income: $3067 Traditional Rental Income: $4114 Airbnb ROI: 0.17% Traditional ROI: 2.51%
8 Happy Haven Rd Wilmington, VT 8 Happy Haven Rd, Wilmington, VT 05363 \| Single Family Residential	3 beds \| 2 baths \| 1,632 sq.ft.	$279,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 7.74% Airbnb Rental Income: $1685 Traditional Rental Income: $2884 Airbnb ROI: 1.39% Traditional ROI: 7.74%
46 Town Farm Rd Wilmington, VT 46 Town Farm Rd, Wilmington, VT 05363 \| Single Family Residential	5 beds \| 2 baths \| 2,000 sq.ft.	$459,000	Airbnb cash on cash: 2.41% Traditional cash on cash: N/A Airbnb Rental Income: $3067 Traditional Rental Income: $0 Airbnb ROI: 2.41% Traditional ROI: N/A

Real Estate investment in Wilmington, VT

There are 64 properties for sale in the city of Wilmington . The median list price in Wilmington is $529,000 and the average price per square foot is $210. In March 2026, the average monthly cash on cash return in Wilmington is 4.00%. The average monthly rental income in Wilmington is $2,733.

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

There are 64 investment properties available for sale in Wilmington.

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

The ROI for Long-Term is higher than the Short-Term in Wilmington with average rental income of $2,733.

Your search for investment property begins and ends here

Investment Property for Sale in Wilmington, VT

195 Mann Rd #12

Wilmington, VT

3 beds | 3 baths | 2,814 sq.ft.

$425,000

Airbnb cash on cash: -1.83%

Traditional cash on cash: 6.28%

Airbnb Rental Income: $1685

Traditional Rental Income: $4443

Airbnb ROI: -1.83%

Traditional ROI: 6.28%

156 W Lake Rd

Wilmington, VT

3 beds | 4 baths | 2,944 sq.ft.

$1,300,000

Airbnb cash on cash: -1.29%

Traditional cash on cash: 1.64%

Airbnb Rental Income: $1685

Traditional Rental Income: $4752

Airbnb ROI: -1.29%

Traditional ROI: 1.64%

41 Two Brook Dr

Wilmington, VT

4 beds | 3 baths | 3,420 sq.ft.

$898,000

Airbnb cash on cash: -0.62%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $1976

Traditional Rental Income: $6604

Airbnb ROI: -0.62%

Traditional ROI: 5.54%

28 Lightning Ledge Way

Wilmington, VT

3 beds | 2 baths | 1,548 sq.ft.

$474,900

Airbnb cash on cash: -0.03%

Traditional cash on cash: 4.3%

Airbnb Rental Income: $1685

Traditional Rental Income: $3139

Airbnb ROI: -0.03%

Traditional ROI: 4.3%

68 E Brook Xing

Wilmington, VT

3 beds | 2 baths | 1,472 sq.ft.

$425,000

Airbnb cash on cash: 0.54%

Traditional cash on cash: 4.88%

Airbnb Rental Income: $1685

Traditional Rental Income: $2944

Airbnb ROI: 0.54%

Traditional ROI: 4.88%

16 Tenth Ln #40

Wilmington, VT

4 beds | 3 baths | 1,800 sq.ft.

$450,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 5.87%

Airbnb Rental Income: $1976

Traditional Rental Income: $4089

Airbnb ROI: -0.38%

Traditional ROI: 5.87%

197 Lake Raponda Road

Wilmington, VT

4 beds | 3 baths | 2,420 sq.ft.

$1,697,000

Airbnb cash on cash: -0.98%

Traditional cash on cash: 0.62%

Airbnb Rental Income: $1976

Traditional Rental Income: $3977

Airbnb ROI: -0.98%

Traditional ROI: 0.62%

34 Binney Brook Rd

Wilmington, VT

4 beds | 3 baths | 2,516 sq.ft.

$675,000

Airbnb cash on cash: -0.07%

Traditional cash on cash: 2.57%

Airbnb Rental Income: $1976

Traditional Rental Income: $3121

Airbnb ROI: -0.07%