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Anthony I Jennings

Anthony I Jennings
Real Estate Agent
Ashland WI

(WI: )

36 years experience

REALTOR® 44 Active Listings Serves Ashland County, WI
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Contact Information

Brokerage
Anthony Jennings & Crew Real Estate Llc

Office Website
Office Address
315 Turner Rd
Ashland, WI  54806
(Ashland County)
Office Phone
715-292-6513
Office Fax
Mobile
715-209-6841
Email
anth***@**********.com
Show Email for $5

Service Areas

La Pointe: WI Bayfield: WI Benoit: WI Cable: WI Cornucopia: WI Drummond: WI Delta: WI Grand View: WI Herbster: WI Barnes: WI Iron River: WI Lac Du Flambeau Reservation: WI Mason: WI Port Wing: WI Washburn: WI Diaperville: WI Sanborn: WI New Odanah: WI Moquah: WI Franks Field: WI Odanah: WI Ashland: WI Morse: WI High Bridge: WI Marengo: WI North Woods Beach: WI Chief Lake: WI New Post: WI Hayward: WI Little Round Lake: WI Reserve: WI Superior City: WI Oliver: WI Superior Village: WI

About Anthony Jennings

Tony is a respected figure in the Northwoods, deeply rooted in the Chequamegon Bay community. As the Broker/Owner of Anthony Jennings & Crew Real Estate and Apostle Islands Realty, he brings over thirty years of comprehensive experience in residential, commercial, and vacant land real estate.

Clients of Tony can anticipate a dedicated and informed advocate who prioritizes their needs and strives to surpass expectations. His team affectionately refers to him as “Captain,” a testament to his ability to instill confidence and facilitate a seamless experience through the complexities of real estate transactions.

A distinctive advantage of working with Tony is his team, known as Crew Jennings, which includes nine licensed real estate professionals, an office manager, a marketing director, and specialists in buyer and seller agency as well as customer care. This collaborative approach ensures that clients receive well-rounded support throughout their real estate journey.

In addition to his extensive real estate expertise, Tony possesses decades of practical experience in building and construction, enhancing his ability to serve clients effectively. He is committed to continuous professional development, having completed various courses through the National Association of Realtors (NAR) and the Wisconsin Realtors Association (WRA), along with workshops focused on alternative and sustainable building practices. His diverse background also includes working with homesteaders and individuals interested in off-grid living, catering to a wide range of client needs.

Tony’s role as Broker/Owner enables him to provide comprehensive services to both buyers and sellers, guiding them through the often intricate processes of real estate transactions. He aims to create empowering experiences that leave clients feeling valued and informed.

His dedication to the Chequamegon Bay area is reflected in his active support for local businesses and organizations, as he believes in fostering a sustainable economy. An enthusiastic outdoorsman, Tony enjoys hunting, fishing, and foraging for wild edibles. When he is not engaged in real estate, he can often be found fishing on the Big Lake, ensuring his freezer is stocked with local, organic foods.

Tony finds great fulfillment in helping others establish their homes and businesses in this stunning region, contributing to the community he cherishes.

Ashland County, WI Real Estate Market Analysis (Single Family Homes)

$295,967
Avg. Listing Price
From Anthony's portfolio
2.9 / 1.8
Avg. Beds/Baths
Typical property size
1,887 sf
Avg. Square Footage
Interior living space
52
Active Listings
Current inventory

Ashland County, Wisconsin's real estate market operates as a unique blend of lakefront luxury and rural accessibility, driven primarily by its stunning Lake Superior shoreline and vast wilderness areas. The market here differs significantly from Wisconsin's urban centers, with seasonal fluctuations playing a major role as summer recreation properties and year-round residential needs create distinct buyer segments throughout the county's communities including Ashland, Mellen, and Butternut.

With only 13 total actively licensed agents serving the entire county, Ashland County represents one of Wisconsin's most intimate real estate markets where personal relationships and local expertise carry exceptional weight. Remarkably, all 13 agents maintain email communication capabilities, reflecting the modern approach even in this traditionally rural market where digital connectivity has become essential for serving both local buyers and out-of-state investors seeking Lake Superior properties.

Major Ashland County, Wisconsin Real Estate Markets

The city of Ashland anchors the county's real estate activity, serving as the commercial and residential hub with its historic downtown district and prime Lake Superior waterfront properties commanding premium prices. Ashland's market encompasses everything from restored Victorian homes to modern lakefront developments, while the Apostle Islands' proximity creates unique investment opportunities for vacation rental properties and seasonal residences that attract buyers from Minneapolis, Chicago, and beyond.

Secondary markets in Mellen, Butternut, and the numerous unincorporated communities throughout the county focus heavily on recreational properties, hunting cabins, and affordable rural homesteads. The Chequamegon National Forest's presence significantly influences property values and development patterns, creating pockets of high-value wilderness retreats alongside more accessible rural properties that appeal to retirees and remote workers seeking affordable Wisconsin living.

Market Dynamics and Geographic Complexity

Ashland County's real estate market operates with surprising complexity despite its small agent population, as properties range from $50,000 rural cabins to million-dollar Lake Superior estates within the same ZIP codes. Seasonal demand creates pronounced market cycles, with spring and summer months seeing intense activity for waterfront and recreational properties, while winter months favor year-round residential transactions and present opportunities for savvy investors to negotiate better terms.

The geographic challenges of serving a county spanning over 1,000 square miles with diverse property types—from Ashland's urban waterfront to remote forest parcels near Glidden—require agents to maintain expertise across multiple market segments. This complexity, combined with the limited agent pool, means that successful real estate professionals here often develop specializations in specific property types or geographic areas while maintaining broad market knowledge.

Why Businesses Need Ashland County, Wisconsin Agent Contact Data

Mortgage lenders, home improvement contractors, and property management companies operating in northern Wisconsin find Ashland County's concentrated agent network invaluable for building referral relationships and understanding local market nuances. With all 13 agents accessible via email, businesses can efficiently reach the entire county's real estate professional network, making targeted marketing campaigns and partnership development remarkably straightforward compared to larger, more fragmented markets.

Insurance providers, title companies, and real estate technology services particularly benefit from direct agent contact data in Ashland County, where personal relationships drive business decisions and the small professional community creates opportunities for deep, long-term partnerships. The county's unique mix of high-value lakefront properties and affordable rural real estate requires specialized services, making direct communication with the complete agent network essential for businesses seeking to establish or expand their presence in this distinctive Wisconsin market.

Current Property Listings

As of 2/17/2026, Anthony Jennings has 44 properties for sale in Ashland and surrounding areas. These are the top 10 listings.

$1,395,000

Listed 2025-12-17

6431 Summit Ave
Washburn, WI  54891

Beds: 3.0
Baths: 1.5
Sq Ft: 3,150
Lot: 214,315 sf
Single Family Map
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$59,900

Listed 2026-01-06

79480 Sweet Fern Ln
Washburn, WI  54891

Beds:
Baths:
Sq Ft:
Lot: 229,126 sf
Land Map
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$139,900

Listed 2025-07-30

814 N 8th Ave W
Washburn, WI  54891

Beds:
Baths:
Sq Ft:
Lot: 155,945 sf
Land Map
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$179,900

Listed 2026-01-13

73995 Ondossagon Rd
Washburn, WI  54891

Beds: 2.0
Baths: 1.5
Sq Ft: 3,873
Lot: 260,924 sf
Single Family Map
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$934,900

Listed 2024-01-28

85780 Smith Dr
Port Wing, WI  54865

Beds: 3.0
Baths: 2.0
Sq Ft: 1,866
Lot: 3,253,496 sf
Single Family Map
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$74,900

Listed 2025-10-02

828XX White Birch Rd
Port Wing, WI  54865

Beds:
Baths:
Sq Ft:
Lot: 217,800 sf
Land Map
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$459,900

Listed 2025-03-19

772XX Lois Ln
Port Wing, WI  54865

Beds:
Baths:
Sq Ft:
Lot: 10,236,600 sf
Land Map
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$9,900

Listed 2025-11-19

20 Acres Near Government Rd
Odanah, WI  54861

Beds:
Baths:
Sq Ft:
Lot: 871,200 sf
Land Map
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$49,900

Listed 2025-10-30

Madigan Rd
Odanah, WI  54861

Beds:
Baths:
Sq Ft:
Lot: 1,742,400 sf
Land Map
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$654,900

Listed 2025-07-30

58715 Noid Rd
Mason, WI  54856

Beds: 3.0
Baths: 3.0
Sq Ft: 2,856
Lot: 871,200 sf
Single Family Map
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Current Property Rentals

Anthony Jennings currently has no rental properties available in Ashland and surrounding areas. Check back later.