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Oberg Insurance & Real Estate Agency

(207) 647-5551

Address

132 Main Street
Bridgton, ME 04009

Open Mon - Fri 8:30 am - 5:00 pm

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Judy Oberg

Judy Oberg Bridgton, ME Real Estate Agent Headshot
Dining room with open French doors, dark chairs, a plaid accent wall, and a chandelier.

Judy Oberg

Judy has been in the Real Estate industry for over 20 years. She has been named Western Maine REALTOR® of the Year and is currently the residing President of the Western Maine Real Estate Board.
 
Judy graduated from the University of New Hampshire. She is very involved with the community and has served on many boards, including the school board for 12 years. She enjoys singing, skiing, swimming, traveling, and all the Greater Lakes Region area has to offer.
 
Call Judy today for expert Real Estate information for both Buyers and Sellers.

Contact Details

Email address [email protected]
Primary phone (207) 838-0059
Address 132 Main St Bridgton ME, 04009
License #003499
Client & Success Stories

Testimonials

They are the most helpful people. Every time I stop in, I receive immediate service. Great Staff.
They are the most helpful people. Every time I stop in, I receive immediate service. Great Staff.
Joann H.
Great place for your insurance or real estate needs. These guys get things done in a timely manner and are always a pleasure to work with.
Great place for your insurance or real estate needs. These guys get things done in a timely manner and are always a pleasure to work with.
Aldi G.
Thanks to Cindy for her friendly, helpful, and professional assistance. My experience at Oberg was a great one!
Thanks to Cindy for her friendly, helpful, and professional assistance. My experience at Oberg was a great one!
Linda L.
Extremely professional and always received prompt replies.
Extremely professional and always received prompt replies.
Bill M.
I recently had the pleasure of working with Cliff Dow. He is experienced in getting the best options for my insurance needs and went above and beyond! Highly recommended!
I recently had the pleasure of working with Cliff Dow. He is experienced in getting the best options for my insurance needs and went above and beyond! Highly recommended!
Anca G.
Excellent communication, and customer service is phenomenal. Great coverage.
Excellent communication, and customer service is phenomenal. Great coverage.
Alicia P.
James Oberg did a wonderful job as our realtor. We have our dream property thanks to him!
James Oberg did a wonderful job as our realtor. We have our dream property thanks to him!
Vinny B.
After working with another broker for a few days with no responses, I googled insurance brokers and called Cliff this morning at 8:30 am with a pain of situation for coverage (for him and me). Cliff had us covered with our new insurance policy in under 4 hours. He was extremely responsive, helpful, and downright enjoyable to work with. Cliff is the man!
After working with another broker for a few days with no responses, I googled insurance brokers and called Cliff this morning at 8:30 am with a pain of situation for coverage (for him and me). Cliff had us covered with our new insurance policy in under 4 hours. He was extremely responsive, helpful, and downright enjoyable to work with. Cliff is the man!
Morghan C.
Working with Cindy was a fantastic experience. She was knowledgeable, responsive, and genuinely cared. Our client couldn’t be happier with the service they received and highly recommends Cindy to anyone in need of a great real estate agent.
Working with Cindy was a fantastic experience. She was knowledgeable, responsive, and genuinely cared. Our client couldn’t be happier with the service they received and highly recommends Cindy to anyone in need of a great real estate agent.
Brittany
Friendly and knowledgeable folks for MLS and insurance.
Friendly and knowledgeable folks for MLS and insurance.
Buyer | Seller
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Sold Listings

Past Transactions

  • Lakefront yard at sunset with a covered pavilion, dock, American flag, and colorful sky. Sold on August 28, 2025

    $2,999,999

    134 Zakelo Road

    134 Zakelo Road, Harrison, ME 04040

    Listing Courtesy of The Lakes Real Estate

    • 4 Beds
    • 3 Baths
    • 2,510 Sq.Ft.
  • Green two-story building with a long covered porch and screened gazebo among autumn trees. Sold on December 31, 2025

    $2,100,000

    149 Pleasant Point Road

    149 Pleasant Point Road, Lovell, ME 04051

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 12 Beds
    • 15 Baths
    • 10,581 Sq.Ft.
  • Woodland lakefront log home with a dock, hammock, and screened porch. Sold on October 7, 2025

    $2,078,600

    296 Hio Ridge Shores South S

    296 Hio Ridge Shores South S, Bridgton, ME 04009

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 4 Beds
    • 4 Baths
    • 3,120 Sq.Ft.
  • Reddish-brown home with a large raised deck among mature trees. Sold on August 12, 2026

    $1,780,000

    42 Knowles Point Road

    42 Knowles Point Road, Bridgton, ME 04009

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 4 Beds
    • 4 Baths
    • 3,636 Sq.Ft.
  • Gray two-story house with a furnished patio, umbrellas, and a fire pit. Sold on October 15, 2025

    $1,750,000

    7 Passby Point Road

    7 Passby Point Road, Windham, ME 04062

    Listing Courtesy of Maine Real Estate Experts

    • 3 Beds
    • 3 Baths
    • 1,984 Sq.Ft.
  • Aerial view of a blue lakeside house with a rocky shore and several docks. Sold on September 26, 2025

    $1,700,000

    81 Whites Point Road

    81 Whites Point Road, Standish, ME 04084

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 3 Beds
    • 3 Baths
    • 1,850 Sq.Ft.
  • Light-colored two-story house with a broad deck, teal shutters, and autumn trees. Sold on July 3, 2025

    $1,610,000

    268-271 Lakewood Road

    268-271 Lakewood Road, Casco, ME 04015

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 5 Beds
    • 4 Baths
    • 3,270 Sq.Ft.
  • Red-sided home with two wooden decks and exterior staircases overlooking a lawn in a wooded setting. Sold on August 15, 2025

    $1,600,000

    21 Swan Road

    21 Swan Road, Harrison, ME 04040

    Listing Courtesy of Chalmers Realty

    • 2 Beds
    • 3 Baths
    • 2,860 Sq.Ft.
  • Lakefront home among trees, with a sandy Long Lake shoreline and lounge chairs. Sold on July 29, 2024

    $1,600,000

    52 Harborside Drive

    52 Harborside Drive, Bridgton, ME 04009

    Listing Courtesy of Pine Tree Realty of Maine

    • 4 Beds
    • 2 Baths
    • 2,912 Sq.Ft.
  • Lakeside cottage among tall pines, with multiple wooden docks extending into the water. Sold on January 26, 2024

    $1,200,000

    539 Cape Monday Road

    539 Cape Monday Road, Harrison, ME 04040

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 4 Beds
    • 3 Baths
    • 2,221 Sq.Ft.
  • Gray-green gable-roofed building at the end of a broad driveway, surrounded by trees and landscaped gardens. Sold on July 19, 2024

    $869,000

    79 Tarkiln Hill Road

    79 Tarkiln Hill Road, Raymond, ME 04071

    Listing Courtesy of Legendary Real Estate

    • 3 Beds
    • 3 Baths
    • 3,249 Sq.Ft.
  • Gray two-story home with a wraparound porch, turret roof, and two-car garage framed by autumn trees. Sold on March 14, 2025

    $866,900

    92 Overlook Lane

    92 Overlook Lane, Casco, ME 04015

    Listing Courtesy of Dan Anderson Real Estate, Inc.

    • 3 Beds
    • 3 Baths
    • 3,426 Sq.Ft.
  • Wooded cabin viewed through tall trees, with a green canoe in the foreground. Sold on November 10, 2025

    $860,000

    316 Hardscrabble Road

    316 Hardscrabble Road, Wayne, ME 04284

    Listing Courtesy of Homestead Realty

    • 3 Beds
    • 2 Baths
    • 2,616 Sq.Ft.
  • Aerial view of a wood-sided home with a large wraparound deck in a wooded mountain setting. Sold on July 23, 2026

    $830,000

    183 Sabattus Trail Road

    183 Sabattus Trail Road, Lovell, ME 04051

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 3 Beds
    • 4 Baths
    • 4,339 Sq.Ft.
  • Two-story gray house with a red front door and attached two-car garage. Sold on June 6, 2025

    $820,000

    20 Stone Brooke Road

    20 Stone Brooke Road, Scarborough, ME 04074

    Listing Courtesy of Keller Williams Realty

    • 3 Beds
    • 3 Baths
    • 2,684 Sq.Ft.
  • White two-story house with a double garage, broad driveway, and mailbox marked 26. Sold on December 16, 2024

    $820,000

    26 Carter Street

    26 Carter Street, Portland, ME 04103

    Listing Courtesy of Greater Portland Realty

    • 4 Beds
    • 3 Baths
    • 2,841 Sq.Ft.
  • Blue two-story house with white trim, gabled roof, and covered front porch. Sold on February 27, 2026

    $812,500

    18 Victoria Lane

    18 Victoria Lane, Windham, ME 04062

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 4 Beds
    • 3 Baths
    • 3,049 Sq.Ft.
  • Red-brick urban development with rooftop terraces at a city street corner, viewed from above. Sold on June 28, 2024

    $800,000

    387 Commercial Street, 532

    387 Commercial Street 532, Portland, ME 04101

    Listing Courtesy of Town & Shore Real Estate

    • 1 Bed
    • 1 Bath
    • 1,043 Sq.Ft.
  • 55 Valhalla Lane Sold on October 8, 2026

    $795,000

    55 Valhalla Lane

    55 Valhalla Lane, Norway, ME 04268

    Listing Courtesy of Bearfoot Realty

    • 3 Beds
    • 2 Baths
    • 1,690 Sq.Ft.
  • Aerial view of a gray barn-style home amid broad lawns, with forest, hills, and a distant lake. Sold on June 18, 2024

    $790,000

    101 Town Farm Road

    101 Town Farm Road, Harrison, ME 04040

    Listing Courtesy of The Aland Realty Group, LLC

    • 3 Beds
    • 3 Baths
    • 1,596 Sq.Ft.
  • Modern dark-sided house with a raised deck and warmly lit windows at dusk. Sold on September 10, 2026

    $760,000

    41 Deertrees Road

    41 Deertrees Road, Harrison, ME 04040

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 3 Beds
    • 3 Baths
    • 1,972 Sq.Ft.
  • Lakeside deck with Adirondack chairs and a dock facing a forested mountain. Sold on September 26, 2025

    $750,000

    41 Sucker Brook Road

    41 Sucker Brook Road, Bridgton, ME 04009

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 3 Beds
    • 1 Bath
    • 1,072 Sq.Ft.
  • A wooded cabin and neighboring homes sit above a rocky shoreline and clear water. Sold on July 25, 2025

    $730,000

    65 Pinecroft Road

    65 Pinecroft Road, Harrison, ME 04040

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 2 Beds
    • 1 Bath
    • 624 Sq.Ft.
  • Modern lakeside home with a broad wood deck, grassy lawn, pine trees, and lake views. Sold on July 31, 2025

    $725,000

    Lot 6 Camp Woodlands Road

    Lot 6 Camp Woodlands Road, Bridgton, ME 04009

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

  • Gray-sided house with a tall brick chimney, covered porch, and bright teal entry door. Sold on November 15, 2024

    $720,000

    83 Cape Monday Road

    83 Cape Monday Road, Harrison, ME 04040

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 4 Beds
    • 4 Baths
    • 2,712 Sq.Ft.
  • Dark blue two-story house with a covered porch, attached garage, and newly graded driveway. Sold on October 1, 2025

    $715,900

    6 Stillwater Drive

    6 Stillwater Drive, Gray, ME 04039

    Listing Courtesy of Signature Homes Real Estate Group, LLC

    • 4 Beds
    • 3 Baths
    • 2,098 Sq.Ft.
  • Green-sided home with a stone facade and covered porch beside a detached two-car garage. Sold on September 30, 2025

    $705,000

    11 Washington Court

    11 Washington Court, Naples, ME 04055

    Listing Courtesy of Maine Real Estate Choice

    • 4 Beds
    • 4 Baths
    • 3,902 Sq.Ft.
  • Red-sided house with cream trim and attached garage, front door marked 29, standing amid snow. Sold on May 28, 2026

    $700,000

    29 Winsor Green Road 29

    29 Winsor Green Road 29, Naples, ME 04055

    Listing Courtesy of RE/MAX Realty One

    • 2 Beds
    • 3 Baths
    • 1,376 Sq.Ft.
  • Lakeside home with red trim, exterior stairs, and a wooden walkway leading toward the water. Sold on July 11, 2025

    $699,000

    63 Naples Road

    63 Naples Road, Harrison, ME 04040

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 3 Beds
    • 1 Bath
    • 728 Sq.Ft.
  • White A-frame home with a detached garage, gravel driveway, and wooded surroundings. Sold on July 23, 2026

    $667,500

    39 Holly Loop

    39 Holly Loop, Bridgton, ME 04009

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 3 Beds
    • 2 Baths
    • 2,112 Sq.Ft.
  • White farmhouse and separate barn with red trim beside a gravel driveway and mature trees. Sold on January 30, 2026

    $665,000

    264 Passaconaway Road

    264 Passaconaway Road, Waterford, ME 04088

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 5 Beds
    • 3 Baths
    • 3,000 Sq.Ft.
  • Two-story red-shingled house behind a stone wall, with yellow flowering shrubs and a lake in the background. Sold on January 23, 2025

    $660,000

    2460 Green Hill Road

    2460 Green Hill Road, Chatham, NH 03813

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 3 Beds
    • 2 Baths
    • 2,640 Sq.Ft.
  • Aerial view of a gray house in a wooded clearing with a gravel driveway. Sold on December 11, 2025

    $650,000

    720 Bridgton Road

    720 Bridgton Road, Sweden, ME 04040

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 3 Beds
    • 3 Baths
    • 2,830 Sq.Ft.
  • Gray two-story home with a covered porch and two-car garage, surrounded by snow and woods. Sold on May 15, 2026

    $645,000

    23 Quarterhorse Drive

    23 Quarterhorse Drive, Bridgton, ME 04009

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 4 Beds
    • 3 Baths
    • 2,450 Sq.Ft.
  • Yellow lakeside house with a broad wooden deck, stairs, and a dock beside the water. Sold on September 10, 2026

    $640,000

    12 Partridge Lane

    12 Partridge Lane, Poland, ME 04274

    Listing Courtesy of Demetria Real Estate

    • 3 Beds
    • 2 Baths
    • 1,486 Sq.Ft.
  • White split-level house with blue shutters, a blue entry door, and a paved driveway. Sold on June 12, 2026

    $639,000

    31 Vernon Road

    31 Vernon Road, Cape Elizabeth, ME 04107

    Listing Courtesy of Locations Real Estate Group LLC

    • 3 Beds
    • 2 Baths
    • 1,894 Sq.Ft.
  • Cream two-story house with a red front door, gray shutters, and flowering shrubs in the yard. Sold on July 30, 2026

    $635,000

    Private Address

    Private Address

    Listing Courtesy of Town & Shore Real Estate

    • 3 Baths
    • 2,700 Sq.Ft.
  • Log cabin with a blue metal roof, furnished deck, and fire pit surrounded by trees. Sold on October 24, 2025

    $622,000

    176 Merrill Corner

    176 Merrill Corner, Brownfield, ME 04010

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 4 Beds
    • 3 Baths
    • 2,436 Sq.Ft.
  • Green-sided two-story house with two dormers, an attached garage, and a landscaped front entry. Sold on July 8, 2024

    $615,000

    307 Black Mountain Road

    307 Black Mountain Road, Sweden, ME 04040

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 3 Beds
    • 2 Baths
    • 2,650 Sq.Ft.
  • Two-story tan house with a detached two-car garage, lawn, and mature trees. Sold on August 8, 2025

    $605,000

    33 Webb Road

    33 Webb Road, Windham, ME 04062

    Listing Courtesy of Landing Real Estate

    • 4 Beds
    • 3 Baths
    • 2,195 Sq.Ft.
  • Lake reflecting a pink-orange sunset, framed by trees, with a small floating dock. Sold on October 15, 2025

    $600,000

    110 Indian Point Drive

    110 Indian Point Drive, Denmark, ME 04022

    Listing Courtesy of The Lakes Real Estate

    • 2 Beds
    • 1 Bath
    • 1,180 Sq.Ft.
  • Modern brown house with angular rooflines and stone accents, surrounded by snow. Sold on February 11, 2026

    $599,900

    7 Brook Haven Lane

    7 Brook Haven Lane, Harrison, ME 04040

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 4 Beds
    • 3 Baths
    • 2,075 Sq.Ft.
  • Vacant kitchen with a white island and sliding glass doors to a balcony. Sold on August 7, 2024

    $589,000

    75 Chestnut Street, 501

    75 Chestnut Street 501, Portland, ME 04101

    Listing Courtesy of Waypoint Brokers Collective

    • 2 Beds
    • 1 Bath
    • 781 Sq.Ft.
  • Wooded lakeshore with a long wooden dock extending into the water. Sold on August 21, 2026

    $582,000

    73 Norway Road

    73 Norway Road, Harrison, ME 04040

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 4 Beds
    • 3 Baths
    • 2,542 Sq.Ft.
  • Blue single-story house with a covered porch and attached garage, surrounded by autumn foliage. Sold on February 20, 2026

    $575,000

    108 Skyview Road

    108 Skyview Road, Harrison, ME 04040

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 3 Beds
    • 3 Baths
    • 2,296 Sq.Ft.
  • White house with rooftop solar panels, a red front door, and an attached garage beside a curved driveway. Sold on June 30, 2025

    $575,000

    39 Senator Black Road

    39 Senator Black Road, Baldwin, ME 04091

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 4 Beds
    • 3 Baths
    • 2,624 Sq.Ft.
  • Log cabin beside a lake with a raised green deck and outdoor seating. Sold on September 24, 2024

    $555,000

    107 Coffee Pond Road

    107 Coffee Pond Road, Casco, ME 04015

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 2 Beds
    • 1 Bath
    • 768 Sq.Ft.
  • Aerial view of a dark-roofed building among autumn trees, with a lake and mountains in the distance. Sold on December 12, 2024

    $555,000

    247 Smarts Hill Road

    247 Smarts Hill Road, Fryeburg, ME 04037

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 2 Beds
    • 3 Baths
    • 1,611 Sq.Ft.
  • House with a steep peaked roof and enclosed sunroom, set among trees beside a curved driveway. Sold on January 3, 2025

    $550,000

    21 Colony Lane

    21 Colony Lane, Bridgton, ME 04009

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 4 Beds
    • 3 Baths
    • 2,700 Sq.Ft.
  • Aerial view of a white lakeside house with a covered porch, detached garage, and paved driveway. Sold on June 6, 2024

    $550,000

    37 Front Street

    37 Front Street, Harrison, ME 04040

    Listing Courtesy of Oberg Insurance & Real Estate Agency, Inc.

    • 4 Beds
    • 3 Baths
    • 1,460 Sq.Ft.
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Oberg Insurance & Real Estate Agency

(207) 647-5551

Mon - Fri, 8:30 am - 5 pm 132 Main Street Bridgton, ME 04009

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Oberg Insurance & Real Estate Agency

(207) 647-5551

Mon - Fri, 8:30 am - 5 pm 132 Main Street Bridgton, ME 04009