Connor LeMire

Born and raised on the Eastern Shore of Maryland, Connor has lived in both Dorchester and Talbot County which provides him with deep local knowledge and an innate passion for the area he calls home.

Growing up, Connor was an avid lacrosse and soccer player as well as the owner of a land management company that served Dorchester and Talbot County from 2013 - 2018 before heading off to the University of Maryland where he studied Economics and Real Estate Development. While at Maryland, he maintained his involvement on the Eastern Shore by purchasing a distressed property in the historic district of Cambridge and restoring it back to its original glory.

After college, Connor took a job with Gartner in their Venture Capital division and then transitioned into private wealth management with Fidelity Investments. During his time at Gartner and Fidelity, he obtained his Series 7 and Series 66 certifications and worked with everyone from families to institutional investors.

After four years away from the beautiful Eastern Shore, Connor decided to move back home to Saint Michaels and embrace the Eastern Shore lifestyle he has always valued. Today, he is a proud member of the Chesapeake Bay Properties Team and specializes in Investment Portfolios and Generational Holdings.

In his free time, Connor enjoys golfing, swimming, and spending time with friends and family.

Top Homes in the Market

Featured Properties

Learn more about our exclusive property offerings and schedule a showing for more information.

Active Under Contract
$1,650,000

602 LANDING ROAD, SAINT MICHAELS, MD 21663
- 3 Beds
- 3 Baths
- 3,078 Sq.Ft.
For Sale
$1,550,000

503 CYNWOOD DRIVE Unit: 1, EASTON, MD 21601
- 5,508 Sq.Ft.
Pending
$1,345,000

40123 SEASIDE DRIVE Unit: 18, FENWICK ISLAND, DE 19944
- 3 Beds
- 3 Baths
- 1,226 Sq.Ft.
Coming Soon
$595,000

11 LONDONDERRY DRIVE, EASTON, MD 21601
- 3 Beds
- 3 Baths
- 1,970 Sq.Ft.
For Sale
$595,000

23730 HENRY ROAD, RIDGELY, MD 21660
- 3 Beds
- 4 Baths
- 3,276 Sq.Ft.
For Sale
$550,000

10490 LONGWOODS ROAD, EASTON, MD 21601
- 4 Beds
- 3 Baths
- 2,252 Sq.Ft.
For Sale
$479,000

8605 HICKORY PLACE, DENTON, MD 21629
- 4 Beds
- 3 Baths
- 2,747 Sq.Ft.
Active Under Contract
$469,000

12401 JAMAICA AVENUE Unit: 358O, OCEAN CITY, MD 21842
- 2 Beds
- 2 Baths
- 953 Sq.Ft.
Pending
$454,900

7453 JEFFREYS WAY, EASTON, MD 21601
- 2 Beds
- 2 Baths
- 1,955 Sq.Ft.
Active Under Contract
$439,900

206 SOUTH STREET, EASTON, MD 21601
- 3 Beds
- 3 Baths
- 1,780 Sq.Ft.
For Sale
$424,900

509 S 2ND STREET, DENTON, MD 21629
- 3 Beds
- 2 Baths
- 1,800 Sq.Ft.
For Sale
$419,900

404 WILLOW BEND DRIVE, GLEN BURNIE, MD 21060
- 3 Beds
- 3 Baths
- 1,920 Sq.Ft.
Pending
$419,000

29772 STANDISH STREET, EASTON, MD 21601
- 3 Beds
- 3 Baths
- 1,440 Sq.Ft.
For Sale
$395,000

178 REGULATOR DRIVE N, CAMBRIDGE, MD 21613
- 4 Beds
- 3 Baths
- 2,220 Sq.Ft.
For Sale
$370,000

13543 WOODBRIDGE ROAD, GREENWOOD, DE 19950
- 3 Beds
- 2 Baths
- 1,872 Sq.Ft.
For Sale
$370,000

408 CROWBERRY CIRCLE, EASTON, MD 21601
- 3 Beds
- 3 Baths
- 1,880 Sq.Ft.
Active Under Contract
$365,000

5658 GATES STREET, ROYAL OAK, MD 21662
- 3 Beds
- 2 Baths
- 1,480 Sq.Ft.
Coming Soon
$330,000

104 CHAMBERS STREET, FEDERALSBURG, MD 21632
- 3 Beds
- 3 Baths
- 1,212 Sq.Ft.
For Sale
$325,000

416 MARYLAND AVENUE, CAMBRIDGE, MD 21613
- 2,514 Sq.Ft.
For Sale
$325,000

416 MARYLAND AVENUE Unit: A & B, CAMBRIDGE, MD 21613
- 4 Beds
- 2 Baths
- 2,514 Sq.Ft.
For Sale
$289,000

12401 JAMAICA AVENUE Unit: 360O1, OCEAN CITY, MD 21842
- 1 Bed
- 1 Bath
- 592 Sq.Ft.
For Sale
$289,000

219 WILLIS STREET, CAMBRIDGE, MD 21613
- 4 Beds
- 3 Baths
- 1,836 Sq.Ft.
For Sale
$275,000

311 YELLOW BILL LN, CAMBRIDGE, MD 21613
- 3 Beds
- 2 Baths
- 1,560 Sq.Ft.