Michael Woolard Real Estate Agent - RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

1331 Laurel Springs Rd, Wintergreen Resort, VA For Sale $59,000 - listed by Michael Woolard — For Sale $59,000

Michael Woolard listing agent for 30 Gumtree Dr, Wintergreen Resort, VA - sold for $649,000 — Sold $649,000

82 Warrior Run, Roseland, VA Pending $675,000 - listed by Michael Woolard — Pending $675,000

Michael Woolard buyer's agent for 22 Deer Springs Ln, Wintergreen Resort, VA - sold for $590,000 — Sold $590,000

25 Hickorynut Dr, Wintergreen Resort, VA For Sale $365,000 - listed by Michael Woolard — For Sale $365,000

Michael Woolard

Charlottesville VA

RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

163 Closed Sales

$60.7M Total Value

$115K - $1.7M Price Range

$372.1K Average Price

Prior 5 years

About Michael

A native Virginian, Mike has been a Wintergreen property owner for 15 years and served on his condominium association for 7. Before Real Estate, Mike worked in the Virginia wine industry for 15 years. He coaches the alpine race team, is an avid cyclist, hiker, and all-around adventurer.

Home Types: Lot/Land, Townhouse, Condo, House, Multifamily

Years of Experience: 18

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	22
Total Value	$8,411,700
Average Sale Price	$382,350
Price Range	$46K - $1.2M

Buyer Deals
Total Deals	9
Total Value	$3,989,000
Average Sale Price	$443,222
Price Range	$185K - $600K

1 Year View by Quarter

Seller Deals
Total Deals	40
Total Value	$16,053,100
Average Sale Price	$401,328
Price Range	$46K - $1.2M

Buyer Deals
Total Deals	18
Total Value	$7,354,000
Average Sale Price	$408,556
Price Range	$50K - $980K

2 Year View by Quarter

Seller Deals
Total Deals	102
Total Value	$35,369,900
Average Sale Price	$346,764
Price Range	$28K - $1.2M

Buyer Deals
Total Deals	61
Total Value	$25,285,850
Average Sale Price	$414,522
Price Range	$19K - $1.7M

5 Year View

Neighborhoods Michael is Experienced In

Michael's Listings and Deals

Michael's Active Listings

$59,000
- Land
- 0.46 Acre
- $128,261 per Acre
1331 Laurel Springs Rd

Wintergreen Resort, VA
Wonderful level lot that backs up to the national forest giving you extended privacy and protection for miles. This lot would be the perfect location for your mountain retreat.

Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$365,000
- 2 Beds
- 2 Baths
- 923 Sq Ft
25 Hickorynut Dr

Wintergreen Resort, VA
The ultimate little Wintergreen cottage located in Black Rock Village, just a short walk to the main lodge. Efficient layout with 2 bd & 2 bath, open floor plan w/ wood burning FP in LR. Several updates including new heat pump, new flooring, kitchen counters, hot tub & shed. Level driveway with only two step entry. Not currently a rental but in the past did average $21k annual gross revenue.

Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$599,000
- 5 Beds
- 4 Baths
- 2,537 Sq Ft
952 Blue Ridge Dr

Wintergreen Resort, VA
This charming mountain house is back on market due to buyers remorse. It has been a successful rental and family vacation spot for the current owners, averaging $30K gross annually. This home features only two steps to enter, Brazilian soap stone counter tops in the kitchen and Travertine stone floors throughout, vaulted ceilings, wood burning FP, and natural wood accents. Spacious layout w/ 5

Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$329,000
- 4 Beds
- 3.5 Baths
- 2,263 Sq Ft
24 Trillium Close

Wintergreen Resort, VA
This beautifully updated and spacious 4BR, tri–level, Townhome is just steps from the Wintergarden Spa & Fitness Center and close to golf, tennis, skiing, and the Nature Foundation. An ideal retreat for rental potential or for hosting two families with ease. Enjoy the privacy and spacious feel of a detached home—without the upkeep. As part of a well managed association, this townhome offers low

Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$49,000
- Land
- 0.41 Acre
- $119,512 per Acre
25 Poll Axe

Wintergreen Resort, VA
Wonderful level lot with easy entry featuring mature hardwoods located on a quiet col du sac. The perfect spot to build your mountain getaway home all within walking distance to Chestnut Springs pool, several great hiking trails and the Shamokin Springs Nature Reserve. The perfect balance of nature's beauty and resort amenities never to be repeated.

Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$675,000

Pending
- 3 Beds
- 2.5 Baths
- 3,370 Sq Ft
82 Warrior Run

Roseland, VA
Only the second owner, this architect designed home was built by Wind Jammer Builders with the vision of true craftsmen. Meticulously maintained and thoughtfully designed, it offers seasonal mountain and sunrise views framed by a dramatic wall of southeast-facing windows and soaring vaulted, paneled ceilings that fill every room with natural light. Private master suite in main floor, while a

Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

Recently Sold

$649,000

Sold Jun 30, 2026
- 4 Beds
- 3.5 Baths
- 3,632 Sq Ft
30 Gumtree Dr

Wintergreen Resort, VA
- 0 Days On Market
- $179/SF
- Current Est. Value $638K
Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$440,000

Sold May 28, 2026
- 2 Beds
- 2 Baths
- 1,237 Sq Ft
1616 Overlook

Wintergreen Resort, VA
- 5% Below List
- 23 Days On Market
- $356/SF
- Current Est. Value $432K
Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$335,000

Sold Apr 24, 2026
- 4 Beds
- 3.5 Baths
- 2,263 Sq Ft
22 Trillium Close

Wintergreen Resort, VA
- 4% Below List
- 37 Days On Market
- $148/SF
- Current Est. Value $341K
Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$369,000

Sold Mar 26, 2026
- 4 Beds
- 3.5 Baths
- 2,412 Sq Ft
29 Trillium Close

Unit A29

Wintergreen Resort, VA
- 101 Days On Market
- $153/SF
- Current Est. Value $392K
Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$155,000

Sold Feb 9, 2026
- 1 Bed
- 1 Bath
- 660 Sq Ft
240 Timbers Condos

Wintergreen Resort, VA
- 112 Days On Market
- $235/SF
- Current Est. Value $162K
Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$463,500

Sold Dec 29, 2025
- 2 Beds
- 2.5 Baths
- 1,443 Sq Ft
962 Diamond Hill Condos

Wintergreen Resort, VA
- 185 Days On Market
- $321/SF
- Current Est. Value $435K
Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$365,000

Sold Dec 19, 2025
- 2 Beds
- 2 Baths
- 1,134 Sq Ft
1421 Highlands Condos

Wintergreen Resort, VA
- 26 Days On Market
- $322/SF
- Current Est. Value $386K
Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$429,000

Sold Dec 15, 2025
- 2 Beds
- 2 Baths
- 1,136 Sq Ft
1933 High Ridge Pl Condos

Wintergreen Resort, VA
- 1 Day On Market
- $378/SF
- Current Est. Value $429K
Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$700,000

Sold Nov 20, 2025
- 3 Beds
- 3 Baths
- 1,421 Sq Ft
134 Squirrel Tree Ln

Roseland, VA
- 40 Days On Market
- $493/SF
- Current Est. Value $714K
Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

Michael Woolard

(434) 260-5031

Homes for Sale by City

Michael Woolard

About Michael

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

2 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Michael is Experienced In

Michael's Listings and Deals

Michael's Active Listings

Recently Sold