Michael Woolard

Charlottesville VA

RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

161 Closed Sales

$58.8M Total Value

$110K - $1.7M Price Range

$365.4K 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: House, Lot/Land, Townhouse, Condo, MultiFamily

Years of Experience: 18

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	26
Total Value	$9,670,600
Average Sale Price	$371,946
Price Range	$46K - $1.2M

Buyer Deals
Total Deals	9
Total Value	$3,022,000
Average Sale Price	$335,778
Price Range	$50K - $980K

1 Year View by Quarter

Seller Deals
Total Deals	48
Total Value	$17,065,400
Average Sale Price	$355,529
Price Range	$46K - $1.2M

Buyer Deals
Total Deals	16
Total Value	$6,163,000
Average Sale Price	$385,188
Price Range	$50K - $980K

2 Year View by Quarter

Seller Deals
Total Deals	103
Total Value	$35,230,900
Average Sale Price	$342,048
Price Range	$28K - $1.2M

Buyer Deals
Total Deals	58
Total Value	$23,595,850
Average Sale Price	$406,825
Price Range	$19K - $1.7M

5 Year View

Neighborhoods Michael is Experienced In

Wintergreen

137 Sales
Nellysford

6 Sales
Southeast Charlottesville

2 Sales
Locust Grove

2 Sales
Afton

2 Sales
Crozet

1 Sale

Michael's Recent Active Listings

$375,000
- 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. Not currently a rental but in the past did average $21k annual gross revenue. Owners is house weekend of 6/19 & 6/20,

Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$218,000
- 1 Bed
- 1 Bath
- 800 Sq Ft
905 Diamond Hill Condos Hill

Wintergreen, VA
Charming slope-side condo featuring stunning slope and valley views with true ski-in/ski-out access. Ideally located in the heart of Center Village, just steps from restaurants, shops, and all the resort amenities. Thoughtful updates over the years include granite countertops, stainless steel appliances, washer and dryer, patio slider, and a beautiful stone fireplace hearth—plus a new HVAC system

Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$625,000
- 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

$349,000
- 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

$252,000
- 2 Beds
- 2 Baths
- 972 Sq Ft
775 Laurelwood Condos

Wintergreen Resort, VA
This updated condo is located in the desirable upper-level section in the Laurelwood complex. This is the closest LW building to all that the center village has to offer. This location offers wonderful seasonal views and a short walk to Black Rock Market, Center Village, and the ski slopes. The unit has been thoughtfully updated over the years, featuring: New appliances and kitchen counters,

Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$54,000
- Land
- 0.41 Acre
- $131,707 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

$139,000
- Land
- 0.54 Acre
- $257,407 per Acre
0 High Crest Ln

Unit 661360

Nellysford, VA
This lot is lake front on Tuckahoe golf course #20, and features views of Crawfords Knob mountain. Slight sloping topography towards the water with a mix of hardwoods makes this lot a great build location. Alse one of the last combination water and mountain view lots in Stoney Creek.

Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$675,000
- 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

$649,000
- 4 Beds
- 3.5 Baths
- 3,632 Sq Ft
30 Gumtree Dr

Wintergreen Resort, VA
Original owners, never a rental, has been a primary residence for 40 years. Beautiful, oversized lot with both together.

Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

Recently Sold

$440,000

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

Wintergreen Resort, VA
- 5% Below List
- $356/SF
- 23 Days On Market
- Current Est. Value $445K
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
- $148/SF
- 37 Days On Market
- Current Est. Value $342K
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
- $153/SF
- 101 Days On Market
- Current Est. Value $378K
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
- $235/SF
- 112 Days On Market
- Current Est. Value $155K
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
- $321/SF
- 185 Days On Market
- Current Est. Value $457K
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
- $322/SF
- 26 Days On Market
- Current Est. Value $382K
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
- $378/SF
- 1 Day On Market
- Current Est. Value $431K
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
- $493/SF
- 40 Days On Market
- Current Est. Value $704K
Michael Woolard RE/MAX REALTY SPECIALISTS-CHARLOTTESVILLE

$530,000

Sold Nov 20, 2025
- 3 Beds
- 2 Baths
- 1,464 Sq Ft
127 Blackrock Cir

Roseland, VA
- $362/SF
- 64 Days On Market
- Current Est. Value $542K
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 Recent Active Listings

Recently Sold