Wilmington, VT Homes for Sale with Pool

/21
$489,000
- 3 Beds
- 2 Baths
- 2,003 Sq Ft
12 Lilla Ln, Wilmington, VT 05363

Beautiful woodsy contemporary chalet located just down from the Chimney Hill Clubhouse in Wilmington. This charming home has nearby access to the country village of Wilmington, Lake Whitingham, is a short drive to the Mt Snow ski resort, and has nearby to one of the best hiking areas in Southern Vermont, thanks to the community adjacent Green Mountain National Forest. It sits nestled on a private

Adam Palmiter Berkley & Veller Greenwood/Dover

12 Lilla Ln, Wilmington, VT 05363
/37
$50,000
- Land
- 0.93 Acre
- $53,763 per Acre
564 Upper Dam Rd, Wilmington, VT 05363

Double lot on top of the Hill! Recent soil tests say this looks good for a 3-bedroom home! If you've been thinking of building your dream home, this is a great spot. Walk to the Clubhouse, seasonal views, about 2,400' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis, basketball, pickleball, ice skating, pond fishing,

Sigrid Pickering Chimney Hill Realty

564 Upper Dam Rd, Wilmington, VT 05363
/23
$474,900
- 3 Beds
- 2.5 Baths
- 1,548 Sq Ft
28 Lightning Ledge Way, Wilmington, VT 05363

Private 2004 country chalet in the Chimney Hill community just outside the village of Wilmington. Hiking trails, snowmobile trail access, and convenient nearby snowmobile trailer parking, make this super convenient for the outdoorsy. This home sits on a rare double lot, just up from the beautifully renovated Chimney Hill clubhouse, Lake Whitingham, and Mount Snow ski resort, affording year round

Adam Palmiter Berkley & Veller Greenwood/Dover

28 Lightning Ledge Way, Wilmington, VT 05363
/60
$449,000
- 4 Beds
- 2.5 Baths
- 1,900 Sq Ft
8 Little Bend Unit M-175, Wilmington, VT 05363

Time to start living the dream with your very own getaway in Chimney Hill! Little Bend Haven is a short walk to the Clubhouse, at the end of the road, with a wood burning fireplace, family room, open concept living, dining and kitchen, with deck, and three levels of living and sleeping spaces. Main level has a mudroom for gear, bedroom and full bath, kitchen/dining, deck with a babbling brook

Sigrid Pickering Chimney Hill Realty

8 Little Bend Unit M-175, Wilmington, VT 05363
/37
$675,000
- 4 Beds
- 3 Baths
- 2,516 Sq Ft
34 Binney Brook Rd, Wilmington, VT 05363

Beautiful upscale chalet in the Chimney Hill community just a short drive from the Mount Snow ski resort and the village of Wilmington. This meticulously maintained turnkey home has been extensively renovated and upgraded, and sits on a private lot along a quiet side road with direct access to nearby snowmobile trails. Inside, a gorgeous great room features vaulted ceilings, exposed natural

Adam Palmiter Berkley & Veller Greenwood/Dover

34 Binney Brook Rd, Wilmington, VT 05363
/28
$449,000
- 3 Beds
- 2 Baths
- 1,510 Sq Ft
49 West Rd, Wilmington, VT 05363

Lovely renovated chalet at the bottom of the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. This lovely private parcel sits in the easily accessible lower section with nice seclusion and views out the rear, affording nice privacy yet with all the conveniences of community living. The interior boasts an open concept living space with natural light and

Adam Palmiter Berkley & Veller Greenwood/Dover

49 West Rd, Wilmington, VT 05363
/32
$675,000
- 3 Beds
- 3 Baths
- 2,216 Sq Ft
12 Three Streams Way, Wilmington, VT 05363

Beautiful 2006 chalet in the Chimney Hill community just a short drive from the Mount Snow Ski Resort and village Wilmington. This meticulous turn key home has been completely renovated and upgraded, and sits on a on a private lot in the Chimney Hill community on a quiet side road with access to snowmobile trails and winter views. Inside is a gorgeous great room space with vaulted ceilings and

Tamara Purcell Berkley & Veller Greenwood Country

12 Three Streams Way, Wilmington, VT 05363
/28
$25,000
- Land
- 0.6 Acre
- $41,667 per Acre
28 Upper Howes Way, Wilmington, VT 05363

BUILD your dream home in Section A! Buyer assumes responsibility for pursuing a septic plan and permit, and all costs associated with permitting and building. Lots 25 & 26 are also available and can be combined for a double or triple lot at the end of the road/world. Enjoy the wellness VT lifestyle and all the 1,200-acre resort with our exclusive member-only clubhouse located at

Sigrid Pickering Chimney Hill Realty

28 Upper Howes Way, Wilmington, VT 05363
/50
$435,000
- 4 Beds
- 2 Baths
- 1,344 Sq Ft
27 Country Ct, Wilmington, VT 05363

Amazingly private cul-de-sac, the nicest location in Chimney Hill! 4 Bedroom 2 Baths, Livingroom with wood stove and a wall of windows to let the outdoors in! Hot Tub on multi-tiered deck. Beautiful wooded lot to explore, garden shed and garage. Live the Resort lifestyle on Chimney Hill's 1,200-Acre Resort Campus, with 550-Acres owned in common by the Homeowners Association. Numerous

Janet Boyd Boyd Real Estate

27 Country Ct, Wilmington, VT 05363
/31
$425,000
- 3 Beds
- 2 Baths
- 1,472 Sq Ft
68 E Brook Crossing, Wilmington, VT 05363

Lovely updated chalet in the Chimney Hill community just outside the village of Wilmington and south of the Mount Snow ski resort. This home sits on a private lot with direct snowmobile trail access, great for summer hiking and biking, nearby access to Lake Whitingham, and is just a short drive into the downtown for shopping and dining. Inside you are treated to a vaulted living space with

Adam Palmiter Berkley & Veller Greenwood/Dover

68 E Brook Crossing, Wilmington, VT 05363
/60
$769,000
- 4 Beds
- 4 Baths
- 2,964 Sq Ft
16 Rock Split Way, Wilmington, VT 05363

Turnkey mountain retreat with style, space, and serious four-season fun—welcome to Chimney Hill living at its best. This beautifully crafted 4 bedroom home offers 4 full tiled baths and approximately 3,000 sq ft of warm, inviting living space on 3 levels designed for gathering, relaxing, and making memories. The open concept main level delivers instant wow factor with soaring cathedral ceilings,

Chad Lackey Deerfield Valley Real Estate

16 Rock Split Way, Wilmington, VT 05363
/29
$25,000
- Land
- 0.6 Acre
- $41,667 per Acre
26 Upper Howes Way, Wilmington, VT 05363

BUILD your dream home in this Lot in Section A! Buyer assumes responsibility for pursuing a septic plan and permit, and all costs associated with permitting and building. Lots 25 & 26 are also available and can be combined for a double or triple lot at the end of the road/world. Enjoy the wellness VT lifestyle and all the 1,200-acre resort with our exclusive member-only clubhouse

Sigrid Pickering Chimney Hill Realty

26 Upper Howes Way, Wilmington, VT 05363
/39
$25,000
- Land
- 0.5 Acre
- $50,000 per Acre
30 Upper Howes Way, Wilmington, VT 05363

Affordable Single Lot with favorable soil tests for a 3-bedroom single family home in Chimney Hill. Surrounded on two sides by common land, this lot is in a quiet section of the Main Hill. Buyer is responsible or securing a septic permit. Join a community of over 560 homes sited on 1,200-Acres adjoining the Green Mt. National Forest, with 550-Acres owned in common by the membership of the HOA.

Sigrid Pickering Chimney Hill Realty

30 Upper Howes Way, Wilmington, VT 05363
/33
$85,000
- Land
- 1.04 Acres
- $81,731 per Acre
402 Fox Mountain Rd, Wilmington, VT 05363

Top of the Hill at the end of the Road! Double building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sac on Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Clubhouse. If you've been thinking of building your dream home, this is a great opportunity!

Sigrid Pickering Chimney Hill Realty

402 Fox Mountain Rd, Wilmington, VT 05363
/32
$559,000
- 3 Beds
- 3 Baths
- 2,080 Sq Ft
9 Greer Ct, Wilmington, VT 05363

Charming 2007 home with recent renovations nestled in the Chimney Hill community just a short drive from the Mount Snow ski resort, country village of Wilmington, and nearby lakes and amenities. This home sits on a private dead end parcel and has unique privacy and curb appeal. Inside you are treated to a large vaulted great room with expansive windows, exposed natural wood ceilings, and great

Adam Palmiter Berkley & Veller Greenwood/Dover

9 Greer Ct, Wilmington, VT 05363
/34
$125,000
- Land
- 1.31 Acres
- $95,420 per Acre
118 Chimney Hill Rd, Wilmington, VT 05363

Brand new Quad Lot right on Chimney Hill Road! Former lots M118 & M119 have had two additional parcels added on each end to form a 1.31-Acre Lot suitable for a three-bedroom single family home. Build your dream home and live the all-season resort lifestyle. Chimney Hill Owners Association is located on 1,200 acres adjacent to the Green Mt. National Forest, with 550 acres owned in common by the

Sigrid Pickering Chimney Hill Realty

118 Chimney Hill Rd, Wilmington, VT 05363
/32
$25,000
- Land
- 0.56 Acre
- $44,643 per Acre
25 Upper Howes Way, Wilmington, VT 05363

BUILD your Getaway Section A! Buyer assumes responsibility for pursuing a septic plan and permit, and all costs associated with permitting and building. Lots 25 & 26 are also available and can be combined for a double or triple lot at the end of the road/world. Enjoy the wellness VT lifestyle and all the 1,200-acre resort with our exclusive member-only clubhouse located at 200'

Sigrid Pickering Chimney Hill Realty

25 Upper Howes Way, Wilmington, VT 05363

Vermont Windham County Wilmington

Home Trends in Wilmington, VT

On average, homes in Wilmington, VT sell after 101 days on the market compared to the national average of 54 days. The median sale price for homes in Wilmington, VT over the last 12 months is $531,250, up 20% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$531,250

Median Single Family Sale Price

$531,250

Median Townhouse Sale Price

$405,000

Median 2 Bedroom Sale Price

$307,000

Average Price Per Sq Ft

$335

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

7.70

Median List Price

$569,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

20%

How to Buy a Home How to Finance a Home How to Sell a Home

In Wilmington, there are currently 17 homes for sale with a pool, providing a refreshing retreat and a space for leisure. Whether it's a house for sale with a pool for those warm summer days, or a property featuring an indoor or screened-in pool for year-round enjoyment, these homes offer recreation right at home. Additionally, buyers can consider properties with access to community pools, offering a convenient space for relaxation and socializing. Whether you prefer a private pool or the convenience of a community pool, browse homes for sale with a pool in Wilmington, VT and discover your ideal residence.

Wilmington Types of Homes for Sale

Wilmington Homes by Price

More About Living in Wilmington

Homes for Sale in Nearby Neighborhoods

Heath Homes for Sale

Homes for Sale in Nearby Cities

Homes for Sale in Nearby Counties

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage