Chimney Hill

What Chimney Hill does

Chimney Hill operates a 1,200-acre single-family owners association in the Green Mountains of Southern Vermont, minutes from Mount Snow and Haystack Mountain ski resorts, functioning dually as a residential community and as a real estate brokerage and property management business under the legal entity Chimney Hill Realty LLC. The community itself is the core asset: an HOA-governed four-season resort with shared amenities including four tennis courts, a pickleball court, an outdoor skating rink, hiking and snowmobile trails (part of the VAST system), a fishing pond, and a recently updated clubhouse with indoor and outdoor pools, hot tub, fitness room, game room, and kids playroom.

The company's revenue mechanics span three streams: real estate brokerage commissions on the sale of homes and land across Southern Vermont (with active listings ranging from small parcels at roughly $17,500 to luxury estates above $3.8M); short-term vacation rental management for three-to-five-bedroom homes booked via the Escapia platform by the weekend, week, month, or season; and long-term and fractional rental programs (long-term winter, long-term summer, half-share winter) for extended-stay guests. Properties are distributed through the company's own chimneyhill.com website with map and favorites functionality, through PrimeMLS, and through a physical sales office at 9 Haystack Road in Wilmington, VT.

Chimney Hill serves individual second-home buyers, investment property buyers seeking rental income, and short-term vacation renters; the principal broker (Sigrid Pickering) and an Executive Director (James Walker) anchor a small team of 1-10 employees. Technology infrastructure is provided by Union Street Media (website and digital marketing) and Escapia (booking), with no proprietary AI/ML systems or technology platform disclosed. The operating model is sales-led and relationship-driven, with customer testimonials and repeat-renter evidence supporting a high-touch local brand rather than a technology-led value proposition.

Name

Chimney Hill

Legal name

Chimney Hill Realty LLC

Website

https://chimneyhill.com

Company type

Private

Founded year

1972

Operating status

Operating

Headcount range

1–10 employees

Short description

Chimney Hill is a 1,200-acre four-season resort community and real estate brokerage in Southern Vermont that sells homes, manages vacation and long-term rentals, and operates HOA amenities near Mount Snow for individual second-home buyers, investors, and short-term renters.

Ownership category

akta.pro rank

Product category

Vacation Rental and Real Estate Brokerage Services

NAICS

Offices of Real Estate Agents and Brokers (53121), Residential Property Managers (531311), Real Estate Property Managers (53131)

SIC

Real Estate Agents & Managers (For Others) (6531), Hotels, Rooming Houses, Camps & Other Lodging Places (7000)

akta.pro primary industry

Mountain & Ski Homes (THAMAAAG)

akta.pro secondary industries

Ski & Mountain Full-Service Hotels (THAGAAAJ), Recreational Land Brokerage (Hunting, Fishing, Wildlife) (BPAJADAD)

Keywords

• Vacation rental management
• Real estate brokerage
• Resort community properties
• Property management services
• Seasonal rental homes

Headquarters

HQ city

Wilmington

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Infrastructure

Revenue model

1. Real Estate Sales Commission: Chimney Hill Realty LLC earns commissions on the sale of homes and properties throughout Southern Vermont, with a focus on the Chimney Hill community and surrounding Mount Snow area.
2. Vacation Rental Management: The company manages vacation rental properties offering short-term rentals by the weekend, week, month or season. Many properties are pet friendly. They offer a full-service rental program including booking, check-in, and property management for owners.
3. Long-term Rental Management: Chimney Hill offers long-term winter and summer rental programs, as well as half-share winter rentals for seasonal occupancy arrangements.

Pricing tiers

Go-to-market motion1 record

Distribution channels3 records

Marketing channels4 records

Core offering

Chimney Hill, via Chimney Hill Realty LLC, operates a real estate brokerage selling homes and land throughout Southern Vermont, with concentration in the Chimney Hill 1,200-acre four-season resort community near Mount Snow. It also provides full-service vacation and seasonal rental property management, including short-term, long-term winter, long-term summer, and half-share rental programs managed end-to-end from booking through check-in and maintenance. Property owners and guests additionally access a private amenities ecosystem including pools, tennis, pickleball, skating rink, clubhouse, fitness room, and trail network.

Product overview

Chimney Hill is a 1,200 acre single family owners association in Southern Vermont offering a unified platform of real estate and rental services through Chimney Hill Realty LLC. The core offerings include real estate sales (Chimney Hill Realty), vacation rentals with multiple term options (short-term, long-term winter, long-term summer, and half-share winter rentals), and community amenities including clubhouse facilities, tennis courts, pickleball, hiking trails, and snowmobile access. The company operates both as a real estate brokerage and property management service for the resort community near Mount Snow.

Differentiator

Problem solved

Functional benefit

Products and services

• Chimney Hill Realty Full-service real estate brokerage specializing in Chimney Hill homes and property sales throughout Southern Vermont, offering residential listings, land sales, and investment properties near Mount Snow. Customers are individual buyers seeking vacation or second homes and investment property purchasers.
• Vacation Rentals (Short-Term) Short-term rental program offering three to five bedroom homes by the weekend, week, month or season, many of which are pet friendly. Managed through the Escapia booking platform for individual vacationers and families.
• Long Term Winter Rentals Seasonal rental program for extended winter ski-season stays in the Mount Snow resort area, targeting individuals and families seeking multi-month winter accommodations.
• Long Term Summer Rentals Extended summer seasonal rental program for stays during the warmer months in Southern Vermont, serving individuals and families seeking multi-month summer accommodations near Mount Snow.
• Half-Share Winter Rentals Half-share fractional winter rental program providing seasonal winter access to Chimney Hill vacation properties for individuals and families who want part-time winter occupancy.
• Chimney Hill Clubhouse & Recreation Facilities Owners association recreational facilities including indoor and outdoor pools, hot tub, fitness room, game room, kids playroom, outdoor playground, tennis courts, pickleball court, outdoor skating rink, and hiking trails, available to Chimney Hill owners and rental guests.

Quantifiable outcome

• Over 285 properties available for sale and extensive vacation rental inventory

Named customers5 records

Segments4 records

Ideal customer profiles4 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Partnerships

One partnership is on record.

• Union Street MediasupportingTechnology or IntegrationUnion Street Media provides the website platform and digital marketing technology for Chimney Hill. They handle website hosting, design, and digital solutions for the real estate industry, including the privacy policy and website functionality.

Scale indicators2 records

Recent moves1 record

Expansion highlights4 records

Broad incumbents

• Vacasa: Large national vacation rental management company. Comparable as a full-service vacation rental manager competing for both property owners and renters, though at a national scale and with a technology-driven operating model.
• Wyndham Vacation Rentals: National vacation rental management company operating across many US destinations. Comparable as a vacation rental management peer, though operating at much larger scale and across multiple geographies.
• Evolve Vacation Rental: National vacation rental management company. Comparable as a vacation rental management competitor for homeowner clients, with a lighter-touch operating model than traditional managers like Chimney Hill.
• Berkshire Hathaway HomeServices: Large national real estate brokerage franchise. Comparable as a real estate sales channel that competes for the same second-home and vacation property buyers in Vermont's resort markets.

Direct peers

• Smugglers' Notch Resort: A Vermont ski and four-season resort offering vacation rentals and real estate services. Directly comparable as a Vermont mountain resort community with vacation home and rental offerings.
• Stowe Real Estate: Real estate brokerage and vacation rental services in the Stowe, Vermont ski market. Directly comparable as a high-end mountain resort community with a similar buyer/renter profile.
• Sugarbush Real Estate: Real estate and rental services at the Sugarbush ski resort in Vermont's Mad River Valley. Directly comparable as a four-season mountain resort real estate and vacation rental operator.
• Stratton Mountain Real Estate: Real estate and rental operations within the Stratton Mountain ski resort community in Southern Vermont. Directly comparable as a mountain ski resort community offering vacation rentals, sales, and HOA-style amenities.
• Mount Snow Realty: A real estate brokerage serving the Mount Snow / Southern Vermont market. Directly comparable as a regional real estate and vacation rental competitor operating in the same micro-market and customer base.
• Killington Real Estate: Real estate brokerage and rental management serving the Killington ski resort area in Vermont. Directly comparable as a ski-area focused brokerage and vacation rental manager serving second-home buyers and renters.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks6 records

Key highlights7 records

Customer concentration

• Xx.com/chimneyhillvt
• Facebookfacebook.com/chimneyhillVT
• Instagraminstagram.com/chimneyhillvt/?hl=en
• LinkedInlinkedin.com/company/chimney-hill-owners-association

Revenue estimate

Valuation estimate

Number of profiles

Profiles2 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Chimney Hill