Tim Flaherty Real Estate Agent - The Flaherty Group

65 High St, Windham, ME For Sale $450,000 - listed by Tim Flaherty — For Sale $450,000

Tim Flaherty listing agent for 103 Commonwealth Dr W, Portland, ME - sold for $575,000 — Sold $575,000

0 Gore Unit 1655428, Gray, ME For Sale $795,000 - listed by Tim Flaherty — For Sale $795,000

Tim Flaherty buyer's agent for 375 Pride St Unit 23, Westbrook, ME - sold for $566,000 — Sold $566,000

Tim Flaherty

Westbrook ME

The Flaherty Group

57 Closed Sales

$23.3M Total Value

$205K - $1M Price Range

$408.3K Average Price

Prior 5 years

About Tim

Flaherty is the designated broker of The Flaherty Group, and an active listing and buyer agent.

Over the years, Tim has earned a loyal following for both his integrity and his deep knowledge of home construction and land use. In addition to listing and selling residential property, Tim has developed several neighborhoods in the greater Portland area, including Brydon Farm and Wildwood in Westbrook, Olde Birch Lane in Portland, Stonebrooke in Scarborough, and Bowdoin Drive in Falmouth. He also offers consulting services for outside developers.

Tim graduated from Portland High School in 1974 and studied real estate at the University of Southern Maine.

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

Years of Experience: 30

Education: University of Southern Maine

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	7
Total Value	$3,677,000
Average Sale Price	$525,286
Price Range	$210K - $1M

Buyer Deals
Total Deals	6
Total Value	$2,399,000
Average Sale Price	$399,833
Price Range	$260K - $566K

1 Year View by Quarter

Seller Deals
Total Deals	11
Total Value	$5,533,500
Average Sale Price	$503,045
Price Range	$210K - $1M

Buyer Deals
Total Deals	8
Total Value	$3,419,000
Average Sale Price	$427,375
Price Range	$260K - $625K

2 Year View by Quarter

Seller Deals
Total Deals	41
Total Value	$15,926,500
Average Sale Price	$388,451
Price Range	$33K - $1M

Buyer Deals
Total Deals	16
Total Value	$7,347,500
Average Sale Price	$459,219
Price Range	$170K - $685K

5 Year View

Areas Tim is Experienced In

Tim's Listings and Deals

Tim's Open Houses

$450,000
- 3 Beds
- 2 Baths
- 1,508 Sq Ft
65 High St

Windham, ME
Tucked in South Windham, an area experiencing exciting momentum as part of the town's ongoing Little Falls/South Windham Villages revitalization plan, this classic 1900 New Englander has been freshly painted from top to bottom and is ready to welcome its next chapter. Wood floors carry you through a sun-filled first floor, where the kitchen, dining room, and living room flow together with ease --

Tim Flaherty The Flaherty Group

Tim's Active Listings

$795,000
- Land
- 100 Acres
- $7,950 per Acre
0 Gore

Unit 1655428

Gray, ME
A rare offering of a 100+ acre parcel ideal for several private estate lots or other forms of development. Nice mix of woods and cleared locations for building. Close to restaurants, shopping, Sebago Lake. Nearby skiing and snowmobile trails.

Tim Flaherty The Flaherty Group

Recently Sold

$575,000

Sold Sep 18, 2026
- 3 Beds
- 2 Baths
- 1,539 Sq Ft
103 Commonwealth Dr W

Portland, ME
- 5% Above List
- 36 Days On Market
- $374/SF
- Current Est. Value $539K
Tim Flaherty The Flaherty Group

$445,000

Sold Aug 28, 2026
- 2 Baths
- 1,901 Sq Ft
132 North St

Westbrook, ME
- 7% Below List
- 179 Days On Market
- $234/SF
- Current Est. Value $473K
Tim Flaherty The Flaherty Group

$1,000,000

Sold Jun 25, 2026
- 3 Beds
- 1.5 Baths
- 1,294 Sq Ft
40 Dyer Rd

Raymond, ME
- 33% Below List
- 54 Days On Market
- $773/SF
- Current Est. Value $1M
Tim Flaherty The Flaherty Group

$437,000

Sold Mar 6, 2026
- 3 Beds
- 2.5 Baths
- 1,925 Sq Ft
50 Rubellite Ln

Unit 60

Auburn, ME
- 3% Below List
- 2 Days On Market
- $227/SF
- Current Est. Value $439K
Tim Flaherty The Flaherty Group

$210,000

Sold Sep 15, 2025
- Land
- 0.30 Acres Lot
Lot B Broadway

South Portland, ME
- 16% Below List
- 122 Days On Market
Tim Flaherty The Flaherty Group

$385,000

Sold Aug 4, 2025
- 3 Beds
- 1.5 Baths
- 1,429 Sq Ft
26 Joseph Dr

Gorham, ME
- 14% Below List
- 80 Days On Market
- $269/SF
- Current Est. Value $413K
Tim Flaherty The Flaherty Group

$625,000

Sold Jul 16, 2025
- 3 Beds
- 2 Baths
- 2,025 Sq Ft
35 Candlewyck Terrace

Portland, ME
- $309/SF
- Current Est. Value $627K
Tim Flaherty The Flaherty Group

$325,000

Sold Apr 8, 2025
- 4 Beds
- 1 Bath
- 1,470 Sq Ft
23 Depot St

Windham, ME
- 24% Below List
- 131 Days On Market
- $221/SF
- Current Est. Value $376K
Tim Flaherty The Flaherty Group

$280,000

Sold Mar 12, 2025
- Land
- 0.48 Acres Lot
Lot A High St

Windham, ME
- 14% Below List
- 79 Days On Market
Tim Flaherty The Flaherty Group

Awards and Designations

NAR - National Association of Realtors

Other Experience

New Construction

Tim Flaherty

(207) 835-3386

The Flaherty Group

(207) 835-3386

Nearby Homes

Tim Flaherty

About Tim

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

Areas Tim is Experienced In

Tim's Listings and Deals

Tim's Open Houses

Tim's Active Listings

Recently Sold

Awards and Designations

Other Experience