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Jesse Fifield

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I’m back in my hometown of Falmouth after 16 years of living, studying and working outside of Maine. My ventures away from home included 4 years of college at Hobart and William Smith, 1 year of teaching in Brazil and 11 years in Boston. I started my real estate career 6 years ago in Boston, specializing in residential sales, leasing and [...]

Portside Picks: 4 Under $400K in Cumberland County!

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Don't miss out on these Cumberland County properties listed below $400,000!

25 Running Hill Road, Scarborough  //  No need to build new! This home is only 5yrs old and shows like a new home w easy living and a very convenient location- This home offers 3 bedroom, 2.5 bath along w open concept living and radiant heat on the first floor , granite counter tops, stainless steel appliances, second floor laundry. Room to move outside and enjoy a fire pit with friends and family and lastly the option to expand on the third floor.
Listed at: $369,000
Listed by: Amanda Vigue

162 Brook Road, Falmouth  //
  Renovated 3BR 1.5BA, 1700 sq. ft. storybook cottage bursting with charm! Some homes are truly special - and this is one of those homes. Privately set back from the road, you pull into a courtyard with apple trees and mature landscaping. The generous sized deck has a winding stone path leading to your wooded back yard with outdoor fireplace, shower and seasonal stream. Step inside to a fully renovated kitchen with breakfast nook, new SS appliances, granite counters, custom cabinets, open to the dining room, first floor half bath and laundry. The oversized living room has a wood burning FP. Spacious first floor master bedroom has a wall of windows and sweet reading nook. Upstairs landing has a cozy built in tv area or home office space. Newly renovated full bath with Carrera marble vanity, plus 2 additional bedrooms upstairs. All bedrooms have impeccable hardwoods under the carpet. Don't overlook the updated systems too! Newer Biasi boiler, oil tank and metal roof, plus a TC Hafford dry basement system with new cement foundation floor. Minutes to Falmouth schools and Portland amenities.
Listed at: $399,000
Listed by: Heather Douglas Mayer

95 Pigeon Brook Road, Baldwin  //
  Located in the scenic southwestern area of the state, 95 Pigeon Brook Road is just 40 minutes from Portland and 40 minutes to North Conway, NH, making it an ideal area for many. The lovely country home, with a welcoming farmer's porch is situated on nearly three acres with a sprawling, fully fenced in yard, an outdoor patio and fire pit - perfect for outdoor entertaining and recreation and ample space to create gardens, or have animals. A detached 12x20 shed with electricity provides extra storage space for all your outdoor tools. Built in 2012, this three bedroom, two full bath home is one level living at it's finest. The kitchen is modern and open with granite counter tops, an island and white cabinetry. The living room just off the kitchen is complete with a gorgeous gas fireplace guaranteed to warm you up on the cooler days. Relax out on the three season sun room that leads out to the back patio and has another gas fireplace. The owner's suite is generous in size and has a full bath and walk in closet. Finished basement provides great space for a family room, studio or office/crafting space. Amazing country setting home with lots of great outdoor space, yet close to all amenities and outdoor recreation including miles of hiking and ATV trails moments away!
Listed at: $339,000
Listed by: Sophia Rosendo

1 Juneberry Court 1F, Yarmouth  //
  Impeccably maintained & sun filled end unit in Yarmouth's Brookside neighborhood. Three bedrooms, two bathrooms, gas fireplace, attached garage & full basement. Large floor master suite and first floor laundry. Private yard with large deck. Close to downtown Yarmouth restaurants & schools. Brookside Condominium Association offers tennis courts, pool & club house and is conveniently located a short distance from town.
Listed at: $379,000
Listed by: Callan Kilroy

Portside Curbside: October 25th!

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Join us Curbside Sunday, October 25th!
Get into a new house, from the comfort of your car!

We'll be here to answer any questions- here's how it will work:


Join us at Stroudwater Preserve in Portland & The Porches in Kennebunk this Sunday!


The Porches, Kennebunk // Hosted by Catie Seavey // 10:00AM-12:00PM, Sunday, October 25th

Stroudwater Preserve, Portland // Hosted by Carly Chasse // 11:00AM-1:00PM, Sunday, October 25th

A Home with a History

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Every home has a story, but this one has quite the history! A duplex in the heart of Portland that was once home to John Ford, the acclaimed director of "Stagecoach," "The Iron Horse," "Grapes of Wrath," and much more. Introducing...

21 Sheridan Street #1, Portland!
This first-floor unit brings style & substance in the East End like no other home can. This two bedroom, and two bath home was thoughtfully transformed with gorgeous design and a keen attention to detail throughout. An open, spacious floorplan welcomes you with an inviting, modern kitchen at its heart. Curl up in front of your fireplace this winter, and next spring take advantage of your private courtyard set in an oversized common garden. A private entrance, smart technology, in-unit laundry, two off-street parking spaces, plenty of storage and a pet friendly building make this home ideal.
$669,000 // Listed by Randy Dee Ferrell, McFarlane Field Associates

If you're curious about John Ford and what his impressive life & career brought to Portland, learn more below!

You may be wondering where you've heard the name John Ford in Maine. As you can see above, there is a statue on Gorham's Corner commemorating his life and impact on Maine throughout his career. Directing 130 films over the course of his life, John Ford made major contributions to film as we know it and this statue was introduced in 1998 to honor that. LEARN MORE HERE!

This home has served as a stop for John Ford fans from across the state, country, and globe. READ HERE for an article from the LA Times and HERE for an article from Boston's Art Fuse on the impact he had on Portland, but also how much people value him beyond our state.

John Ford lived on Sheridan Street- but so did two other Irish-American figures in Maine! To learn about how John Ford crossed paths with Pat A. Mahoney & Michael H. Myers, READ HERE!

Meet our Fresh Faces!

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Meet David: 

David Bruce has joined us as Director of Business Development and Integration. David has a strong real estate background from owning and operating a very successful agency in Virginia to most recently a corporate position with Realogy. He has a ton of experience, but most importantly, he naturally has the Portside integrity, grit, and kindness.


Meet Nicole:
Nicole Saucier has joined Portside as our Operations Manager. Nicole has over 15 years of real estate experience with a strong focus on agent support including developing and implementing an agent concierge program. Nicole is spearheading the roll out of our NEW innovative tech suite which will integrate best-in-class tools and services all at our Portsider's fingertips!
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Wondering HOW Portside supports our agents?

If you're not feeling 100% connected, supported and aligned with the culture at your current agency, perhaps it's time for a change.

Portside is Giving 1% for Maine!

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At Portside, we are Mainers helping Mainers- it's what we do every day!


1% for Maine focuses on the next generation, Maine’s youth. Supporting and addressing systemic Maine problems including generational poverty, substance abuse, and limited access to medical care, education, and food. Portside is committed to giving one percent of gross revenue to Maine's future.

All of these causes align with Portside's values, and to do our part, we plan to give 1% of our top line revenue to Full Plates Full Potential. We encourage anyone that can to join the cause and learn more about 1% for the Maine HERE!

Portside is committed to giving one percent of gross revenue Maine's to future.

Let's leave a lasting legacy!

Portside Picks: 3 Under $300K in Greater Portland!

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Check out these Greater Portland properties listed below $300,000!

285 Sawyer Street, South Portland  //  Make your new Home at 285 Sawyer Street in South Portland! This updated 4 bedroom Cape has so much to offer with a newer kitchen, renovated bath, hardwood floors throughout, and a wood burning fireplace in the living room. The backyard is an oasis with beautiful perennials, raised garden beds and plenty of space to gather. Conveniently located minutes from Portland, the sweet home is just down the street from Willard Beach and near the Greenbelt Walkway.
Listed at: $295,000
Listed by: Randy Dee Ferrell, McFarlane Field Associates
1 Fisher Street, Portland  //
  Sweet 3 bedroom, 1 bath in North Deering. Updated one level living on a quiet dead end street. Recent updates include all new windows & doors, granite countertops & stainless appliances. Generous back deck & yard for entertaining. Just around the corner from the grocery store & Lib's!
Listed at: $265,000
Listed by: Callan Kilroy
50 Florida Avenue, Portland  //
  Just Listed!! Updated open concept 3BR ranch style home in established North Deering neighborhood. Set on a quiet street abutting woods, this home has been lovingly maintained by the same family for over 50 years. Brand new kitchen with granite, SS appliances, fabulous tile backsplash. Kitchen counter seating open to the large dining room and sunken living room with custom stone and granite wood burning FP. Master bedroom with large closet, two additional bedrooms plus a bonus room. Spacious deck and 2 large storage sheds in fenced back yard overlooking woods. Property extends 100 feet beyond fencing. Metal roof, efficient natural gas heat and Rinnai on demand water heater. Short walk to multiple Portland Trails and minutes to shopping and amenities. Home has been pre-inspected!
Listed at: $279,000
Listed by: Heather Douglas Mayer

modern living room with wood flooring and dining table. Blue filter overlaying image. modern living room with wood flooring and dining table. Blue filter overlaying image. modern living room with wood flooring and dining table. Blue filter overlaying image.

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