Kayla Sterling Real Estate Agent - Waypoint Brokers Collective

30 Daytona St, South Portland, ME Pending $399,900 - listed by Kayla Sterling — Pending $399,900

Kayla Sterling listing agent for 68 Old Dunning Rd, Harpswell, ME - sold for $250,000 — Sold $250,000

47 Margaret St, Naples, ME Pending $249,900 - listed by Kayla Sterling — Pending $249,900

Kayla Sterling buyer's agent for 1 Cross St Unit 104, Scarborough, ME - sold for $410,000 — Sold $410,000

Kayla Sterling

Portland ME

Waypoint Brokers Collective

58 Closed Sales

$31.9M Total Value

$300K - $1.5M Price Range

$549.3K Average Price

Prior 5 years

About Kayla

Kayla Sterling is an experienced Associate Broker based in Portland, Maine. Graduating from the University of Southern Maine, she has since embarked on a successful real estate career, consistently ranking as a top performer and earning recognition as a Certified Luxury Property Marketing Specialist. Kayla is renowned for going above and beyond for her clients, ensuring their needs are met with exceptional dedication and expertise.

One of the things Kayla enjoys most about real estate is the people she meets and the shared passion for the state of Maine. She is dedicated to guiding her clients from beginning to beyond. Kayla says "beyond" because she is committed to being a resource and guide long after the transaction is over, treating every client as a VIP.

Kayla's experiences living in Nashville, San Francisco, and Lake Tahoe have provided her with a rich and diverse perspective that she brings to her work. An active member of the Women's Junior League in Portland, she is deeply committed to her community.

In her free time, Kayla loves traveling, skiing, and spending time with her golden retriever, Jackson, who is named after her favorite ski town in Wyoming! Her passion for adventure and community involvement makes her a well-rounded and dynamic presence in the Portland real estate scene.

Home Types: House, Mobile Homes, Condo, Multifamily, Lot/Land

Years of Experience: 6

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	6
Total Value	$3,602,640
Average Sale Price	$600,440
Price Range	$250K - $1.5M

Buyer Deals
Total Deals	5
Total Value	$2,784,000
Average Sale Price	$556,800
Price Range	$410K - $705K

1 Year View by Quarter

Seller Deals
Total Deals	18
Total Value	$12,037,640
Average Sale Price	$668,758
Price Range	$250K - $1.5M

Buyer Deals
Total Deals	11
Total Value	$6,599,196
Average Sale Price	$599,927
Price Range	$389K - $808K

2 Year View by Quarter

Seller Deals
Total Deals	32
Total Value	$17,700,956
Average Sale Price	$553,155
Price Range	$200K - $1.5M

Buyer Deals
Total Deals	26
Total Value	$14,160,837
Average Sale Price	$544,648
Price Range	$199K - $1.3M

5 Year View

Areas Kayla is Experienced In

Kayla's Listings and Deals

Kayla's Active Listings

$399,900

Pending
- 2 Beds
- 1 Bath
- 1,045 Sq Ft
30 Daytona St

South Portland, ME
Located on a quiet dead-end street in South Portland, this home offers a large yard while keeping you close to everything. Enjoy easy access to downtown Portland, Willard Beach, the Maine Mall, local restaurants and shopping, with Scarborough and Cape Elizabeth just minutes away. The generous yard provides plenty of room to relax, garden, entertain, or simply enjoy the outdoors. A convenient

Kayla Sterling Waypoint Brokers Collective

$249,900

Pending
- 2 Beds
- 1 Bath
- 1,152 Sq Ft
47 Margaret St

Naples, ME
Tucked away on a private wooded lot in Naples, this home offers close proximity to some of the area's most sought-after attractions. Conveniently located near Long Lake, Sebago Lake, the Naples Causeway, restaurants, marinas, shopping, and year-round outdoor recreation, this property makes it easy to enjoy everything the Lakes Region has to offer. Inside, the home features a spacious and

Kayla Sterling Waypoint Brokers Collective

Recently Sold

$250,000

Sold May 29, 2026
- 3 Beds
- 648 Sq Ft
68 Old Dunning Rd

Harpswell, ME
- 3 Days On Market
- $386/SF
- Current Est. Value $364K
Kayla Sterling Waypoint Brokers Collective

$420,000

Sold Apr 30, 2026
- 3 Beds
- 2 Baths
- 1,568 Sq Ft
593 Pequawket Trail

West Baldwin, ME
- 1% Above List
- 4 Days On Market
- $268/SF
- Current Est. Value $418K
Kayla Sterling Waypoint Brokers Collective

$315,000

Sold Apr 9, 2026
- 3 Beds
- 2 Baths
- 1,361 Sq Ft
51 Newell St

Gorham, ME
- 5% Above List
- 11 Days On Market
- $231/SF
- Current Est. Value $320K
Kayla Sterling Waypoint Brokers Collective

$1,450,000

Sold Dec 30, 2025
- 4 Beds
- 3.5 Baths
- 3,874 Sq Ft
1010 Sawyer Rd

Cape Elizabeth, ME
- 12% Below List
- 75 Days On Market
- $374/SF
- Current Est. Value $2M
Kayla Sterling Waypoint Brokers Collective

$325,000

Sold Nov 13, 2025
- 3 Beds
- 2 Baths
- 1,040 Sq Ft
80 Diamond Ln

Hollis Center, ME
- 11% Below List
- 5 Days On Market
- $312/SF
- Current Est. Value $358K
Kayla Sterling Waypoint Brokers Collective

$842,640

Sold Aug 29, 2025
- 3 Beds
- 2.5 Baths
- 2,204 Sq Ft
8 Track View Terrace

Scarborough, ME
- 12% Above List
- $382/SF
- Current Est. Value $810K
Kayla Sterling Waypoint Brokers Collective

$800,000

Sold Jun 9, 2025
- 3 Beds
- 2 Baths
- 2,007 Sq Ft
2 Timber Sands Dr

Scarborough, ME
- 19 Days On Market
- $399/SF
- Current Est. Value $803K
Kayla Sterling Waypoint Brokers Collective

$530,000

Sold Mar 21, 2025
- 3 Beds
- 3 Baths
- 1,292 Sq Ft
60 Bolton St

Portland, ME
- 23% Below List
- 169 Days On Market
- $410/SF
- Current Est. Value $551K
Kayla Sterling Waypoint Brokers Collective

$490,000

Sold Mar 14, 2025
- 3 Beds
- 1.5 Baths
- 1,372 Sq Ft
60 Alden Cir

Portland, ME
- 15% Below List
- 131 Days On Market
- $357/SF
Kayla Sterling Waypoint Brokers Collective

Kayla Sterling

(207) 544-4415

Waypoint Brokers Collective

(207) 544-4415

Nearby Homes

Kayla Sterling

About Kayla

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 Kayla is Experienced In

Kayla's Listings and Deals

Kayla's Active Listings

Recently Sold