Top 5 Best Realtors in Charlottesville

Your 2026 Guide to Exceptional Charlottesville Realtors

Charlottesville, Virginia, stands as one of the most attractive real estate markets in the Commonwealth, drawing homebuyers with its rich history, prestigious University of Virginia campus, stunning Blue Ridge Mountain backdrop, and vibrant cultural scene.

Whether you are searching for a historic downtown property, a luxury estate in Albemarle County, or a cozy family home in one of the area’s charming neighborhoods, working with an experienced realtor can make all the difference in your real estate journey.

The following top 5 best Charlottesville realtors represent the very finest that Charlottesville has to offer, combining deep market knowledge, exceptional client service, and proven track records of success.

Loring Woodriff Real Estate Associates

A premier, one-office boutique firm specializing in the purchase and sale of distinctive homes, farms, and estates throughout Charlottesville and the Virginia Piedmont.
Founded in 2006 by Loring Woodriff, the firm has cultivated a reputation for excellence by blending local expertise with sophisticated, high-end marketing strategies.
Its central headquarters at 401 Park Street in downtown Charlottesville serves as the hub for a highly specialized team of approximately 30 full-time realtors.
The firm’s founder, Loring Woodriff, brings a unique professional background to the Central Virginia market, including experience on Wall Street and years as an advertising executive for Polo Ralph Lauren in New York City.
This experience in luxury branding and corporate finance is reflected in the firm’s “aspirational yet welcoming” approach to real estate marketing.
By 2025, Woodriff herself will have surpassed $800 million in individual sales, maintaining an average transaction size of over $2 million.
Since early 2020, the firm has established itself as the market leader in high-end transactions, consistently ranking as the largest company by sales volume for properties priced at $1 million or higher.
In 2023, the firm closed over $411 million in total sales, achieving the highest average unit price in the region at approximately $843,000.
These figures are notably achieved by a much smaller team than their competitors, resulting in a significantly higher average sales volume per agent.
A hallmark of the firm is its focus on aesthetically sophisticated marketing.
Every listing is treated with a bespoke strategy that includes professional photography and materials created by an in-house graphic design team.
The firm prioritizes quality over quantity, ensuring that its marketing materials remain uncluttered and that each property receives maximum visibility through social media and traditional channels.
The associates at Loring Woodriff are full-time professionals who are carefully recruited for their integrity and market knowledge.
For instance, Associate Broker Tommy Brannock, a Charlottesville native and University of Virginia graduate, has been active in the local market since 1981, averaging 40 to 50 transactions annually.
Other key agents, such as Lisa Lyons and Jamie Waller, bring diverse backgrounds in investment banking and professional staging to assist their clients.
The firm’s reach extends beyond standard residential sales into the luxury farm and estate market, covering counties such as Albemarle, Orange, Fluvanna, and Nelson.
This regional expertise allows them to navigate the complexities of large-acreage transactions and conservation easements common in the Virginia Piedmont.
Their agents are often deeply embedded in these communities, offering clients insights into local schools, social clubs, and neighborhood dynamics.
In addition to sales, the firm established a dedicated property management division in 2013.
This service allows clients to handle leasing needs, tenant screening, and property maintenance through a single trusted entity.
By offering these diverse services, the firm ensures it can support clients through various stages of property ownership, whether they are looking for a permanent residence or an investment property.
Client testimonials often highlight the personalized, “hands-on” nature of the service provided by Loring Woodriff realtors.
Unlike larger, franchised firms that may rely on automated systems, agents like Jamie Waller personally coordinate showings and provide tailored follow-ups for every interaction.
This level of commitment has resulted in high rates of repeat business and referrals.
The firm’s performance in 2025 continues to reflect its status as a top producer in the region.
Lindsay Milby, with over $600 million in career sales, exemplify the high caliber of the team.
Their collective success is built on a foundation of strategic negotiation and unwavering client advocacy.
Prospective buyers and sellers can explore current listings and meet the full team of Loring Woodriff Real Estate Associates via their website.
By maintaining a single office and a boutique feel, the firm ensures that every client receives the benefit of their collective expertise while enjoying the intimacy of a local business.

Jim Faulconer: Innovative Marketing and Client-Centered Service

Jim Faulconer is a cornerstone of the Charlottesville real estate community, serving as President and Principal Broker of McLean Faulconer Inc.

With over 50 years of experience as a licensed Virginia real estate broker, he has established himself as one of the area’s most respected professionals, known for his deep market knowledge and unwavering commitment to clients.

A native of Charlottesville, Jim grew up immersed in the local landscape and culture, which has informed his lifelong career in real estate.

Alongside his partner Stephen T. McLean, he co-founded McLean Faulconer Inc. in 1980, building a firm dedicated to personalized service and expertise in Central Virginia properties.

The firm, under Jim’s leadership, specializes in a wide range of real estate, from residential homes and vacant land to luxury estates, farms, and commercial properties across Albemarle County and beyond.

Jim has personally handled transactions in all price ranges, demonstrating versatility and a keen understanding of the diverse needs of buyers and sellers throughout the Commonwealth of Virginia.

Among his most notable achievements are landmark sales, including the transfer of Montalto, a 300-plus-acre estate adjoining Monticello – to the Thomas Jefferson Memorial Foundation, the sale of the scenic 43-acre Lewis Mountain estate overlooking UVA and the city, and representing the Colonial Williamsburg Foundation in the sale of the historic Carter’s Grove estate dating back to circa 1750.

Jim’s influence extends far beyond transactions; he is deeply invested in the community that shaped him.

He has served on numerous local boards and provided financial support to organizations such as Martha Jefferson Hospital, the UVA Medical Center, the Charlottesville SPCA, the Thomas Jefferson Memorial Foundation, the Virginia Athletic Foundation, and the Paramount Theater.

On a personal note, Jim resides in Albemarle County with his wife Gail, to whom he has been married for over 40 years.

The couple has three children and seven grandchildren, all living in the Charlottesville area, reflecting his strong family ties to the region.

Recently, he has teamed up with his son Will Faulconer, a licensed realtor, to offer multigenerational expertise to clients.

Clients and peers alike praise Jim for his exceptional service, accessibility, and profound knowledge of the local market.

Testimonials highlight his reputation as a premier agent who goes above and beyond, ensuring smooth transactions with a client-focused approach that has earned lasting trust and loyalty in Charlottesville’s competitive real estate landscape.

Jim Duncan: Technology-Forward Real Estate Excellence

As an Associate Broker and Partner at Nest Realty, Jim Duncan has built a reputation as one of Charlottesville’s most knowledgeable and tech-savvy real estate professionals.

His blog and website, RealCentralVA.com, have become essential resources for anyone interested in the Charlottesville real estate market, providing detailed market analysis, neighborhood guides, and insights into market trends that help both buyers and sellers make informed decisions.

Duncan’s embrace of technology sets him apart in an industry that has sometimes been slow to adapt.

He was among the first Charlottesville agents to leverage blogging, social media, and data analytics to serve clients better.

His commitment to transparency means that much of the market research and analysis that other agents keep proprietary is freely shared on his platforms, establishing him as a trusted resource even for people who are not yet ready to work with an agent.

This educational approach builds trust with potential clients long before they are ready to buy or sell.

By the time clients are ready to engage Duncan’s services, they already understand his expertise, market knowledge, and commitment to client advocacy.

This foundation of trust leads to smoother transactions and better outcomes for everyone involved.

Duncan’s real estate practice emphasizes communication and responsiveness.

Clients consistently praise his availability and his ability to explain complex real estate concepts in clear, accessible language.

Whether dealing with first-time homebuyers who need significant guidance or experienced investors looking for detailed market analysis, Duncan adjusts his communication style to meet each client’s needs and knowledge level.

His partnership with Nest Realty, a progressive brokerage known for its agent-centered culture and commitment to ethical practices, provides Duncan with the support and resources to serve clients effectively while maintaining the independence to advocate strongly for their interests.

This combination of resources and autonomy allows him to provide the best of both worlds with boutique-level service backed by solid institutional support.

Duncan’s price range extends from starter homes to luxury properties, and his transaction history demonstrates consistent success across the spectrum.

His understanding of different market segments allows him to provide accurate pricing guidance, realistic timelines, and strategic advice regardless of price point.

Kristin Cummings Streed: Experienced Guidance and Neighborhood Expertise

Kristin Cummings Streed of Nest Realty brings extensive experience and deep neighborhood knowledge to her real estate practice.

As a local Charlottesville realtor, Kristin has guided countless clients through successful real estate transactions, earning consistently high reviews for her professionalism, market expertise, and genuine care for her clients’ interests.

Kristin’s understanding of the best Charlottesville neighborhoods runs deep, accumulated over many years of active practice in the market.

She can speak knowledgeably about school districts, commute patterns, neighborhood amenities, future development plans, and the subtle characteristics that make each area unique.

This knowledge helps clients narrow their search to neighborhoods that genuinely fit their lifestyle, priorities, and budget.

For sellers, Kristin’s experience proves invaluable in pricing strategies, preparing homes for market, timing listings, and negotiating offers.

She understands that selling a home involves both financial and emotional dimensions, and she provides steady guidance through both aspects.

Her staging advice and marketing strategies help properties show their best while her negotiation skills ensure that sellers achieve optimal results.

Clients appreciate Kristin’s calm demeanor and problem-solving abilities.

Real estate transactions inevitably involve challenges, from inspection issues to financing complications to timing concerns, and Kristin’s experience allows her to address these obstacles efficiently while keeping transactions moving forward.

Her relationships with other real estate professionals, inspectors, contractors, and service providers throughout the Charlottesville area facilitate smooth transactions.

Kristin’s association with Nest Realty aligns with her client-centered approach.

Nest Realty’s commitment to ethical practices, agent education, and client advocacy provides the perfect environment for Kristin’s practice.

The brokerage’s reputation for integrity and professionalism enhances Kristin’s already strong personal brand.

Whether representing buyers or sellers, Kristin provides full-service real estate assistance characterized by attention to detail, clear communication, and unwavering commitment to her clients’ best interests.

Her track record speaks for itself with numerous successful transactions and satisfied clients who frequently refer friends and family to her services.

Sally Du Bose and Virginia Real Estate Partners

Sally Du Bose is a longtime Charlottesville-area real estate broker who has been licensed since 1987 and leads Sally Du Bose Real Estate Partners.

Her profile highlights decades of local experience and specialization across land, farms, estates, and residential properties.

A few resume-style markers from her official bio that often correlate with “top Charlottesville realtor” status in a market:

Real Estate Licensee since 1987 and deep local roots (Charlottesville resident for 40+ years per her bio).
Salesperson of the Year / Top Producer (2003–2008) (as stated on her site).

Broad property-type scope (from first-time buyers to farms/estates), which is a big differentiator in a diverse market like greater Charlottesville/Albemarle.

Why she’s considered one of the top 5 Charlottesville realtors (based on published signals)

1) Longevity + production recognition
Her official bio explicitly notes multi-year Top Producer/Salesperson of the Year (2003–2008), and her licensure dates back to the late 1980s, both commonly-cited indicators of sustained performance. Source

2) “Local knowledge” that shows up in client feedback
Testimonials published on the firm’s site repeatedly emphasize:

deep market knowledge (“wide and very deep”),
responsiveness,
attention to detail,
strong process guidance and negotiation on complex deals (including farm/land transactions).

These are exactly the themes buyers and sellers associate with “top Charlottesville realtors”.

3) Community and UVA involvement (network + trust)
Her bio lists extensive community and University of Virginia involvement (boards, advisory roles, and founding a fund), which can matter a lot in relationship-driven real estate markets, especially for referral business and trust-based reputation.

Then there is Toby Beavers…

Toby Beavers: Master of Charlottesville History and Charlottesville Best Neighborhoods

Toby Beavers of TobyBeaversRealtor.com has established himself as one of the most knowledgeable and respected real estate professionals in Charlottesville since beginning his career in the area in 2003.

Toby wishes he was one of the top Charlottesville realtors and strives every day to become one of the top 5 Charlottesville realtors.

What sets Beavers apart from other agents is his extraordinary understanding of the best Charlottesville neighborhoods, architectural heritage, and local history.

This deep knowledge proves invaluable to clients seeking not just a house, but a home that fits their lifestyle and connects them to the community’s rich cultural tapestry.

With over two decades of real estate experience dating back to 1996 when he first became a licensed realtor in Florida and Rhode Island, Beavers brought a wealth of expertise to Charlottesville when he arrived in 2003.

His specialization in Charlottesville luxury homes, Charlottesville condos, and Charlottesville townhomes has made him the go-to agent for discerning buyers and sellers seeking high-end properties.

What truly distinguishes Toby Beavers is his ability to share detailed historical context about Charlottesville’s diverse neighborhoods.

From the tree-lined streets of Belmont to the prestigious estates of Farmington homes for sale, from the walkable urban environment of downtown to the scenic countryside properties of Albemarle County, Beavers can explain the unique character, architectural styles, and historical significance of virtually every corner of the area.

This knowledge helps buyers make informed decisions that go beyond square footage and price per square foot.

Clients consistently praise Beavers for his professionalism, responsiveness, and genuine passion for real estate.

His background as an explorer, author, Broadway producer, entertainer, master gardener, and chef brings a creative and cultured perspective to his real estate practice.

This diverse experience allows him to connect with clients from all walks of life and understand what makes a property special beyond its basic features.

Beavers’ commitment to staying current with market trends while maintaining deep roots in the community’s history makes him an exceptional resource for both Charlottesville luxury homes and seasoned Charlottesville investors.

His comprehensive understanding of property values, neighborhood dynamics, and future development plans enables him to provide strategic advice that serves his clients’ long-term interests.

Choosing the Top 5 Best Realtors in Charlottesville in 2026 for Your Needs

The Charlottesville real estate market offers tremendous opportunities for both buyers and sellers, but navigating this market successfully requires expertise, local knowledge, and professional guidance.

The five best Charlottesville realtors featured here represent different strengths and approaches, but all share common characteristics including deep market knowledge, ethical practices, strong communication skills, and genuine commitment to client success.

When selecting a realtor, consider what matters most to you.

If you want to work with a statewide recognized leader with a comprehensive team approach, Loring Woodriff offers unmatched credentials and resources.

For innovative marketing and high energy advocacy, Jim Faulconer delivers exceptional results.

If you value technology and transparency, Jim Duncan’s data-driven approach provides clarity and confidence.

And if you seek experienced guidance with a calm, professional demeanor, Kristin Cummings Streed offers the steady expertise that leads to successful outcomes.

If neighborhood expertise are priorities, Sally Du Bose’s’ deep understanding of Charlottesville’s heritage and communities makes her an excellent choice.

Charlottesville’s real estate market continues to attract buyers from across the country drawn to the area’s quality of life, natural beauty, cultural amenities, and economic opportunities.

Working with an experienced Charlottesville realtor who knows the market intimately and advocates effectively for your interests makes the difference between a stressful experience and a successful, satisfying real estate transaction.

Any of these five outstanding professionals including myself would serve you well in your Charlottesville real estate journey.

Toby Beavers, working hard to become one of the top 5 Charlottesville realtors, may be reached at 434-327-2999

Toby Beavers - one of the top 5 best realtors in Charlottesville since 2003