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Richard Caplan

Richard Caplan
Real Estate Agent (Broker)
West Dover VT

Broker (VT: 081.0004442)

38 years experience

REALTOR® 9 Active Listings Serves Windham County, VT
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Contact Information

Brokerage
Deerfield Valley Real Estate

Office Website
Office Address
183 Route 100
West Dover, VT  05356
(Windham County)
Office Phone
802-464-3055
Office Fax
Mobile
802-464-3055
Email
raca****@******.com
Show Email for $5

Service Areas

East Dover: VT Readsboro: VT Whitingham: VT South Newfane: VT Marlboro: VT Wardsboro: VT Mount Snow: VT West Dover: VT West Halifax: VT Halifax: VT West Wardsboro: VT Stratton: VT Jamaica: VT West Marlboro: VT Wilmington: VT Searsburg: VT Stamford: VT Newfane: VT Brookline: VT Londonderry: VT South Londonderry: VT Stratton Mountain: VT Guilford: VT Vernon: VT Dummerston: VT West Brattleboro: VT Brattleboro: VT West Dummerston: VT

About Richard Caplan

Richard Caplan serves as the Principal Broker and Owner of Deerfield Valley Real Estate. A native of West Hartford, Connecticut, he relocated to the area in 1987 and embarked on his real estate career in 1989. Currently, he holds a position on the board of directors for both the Southern Vermont Deerfield Valley Chamber of Commerce and the Grand Summit Hotel. With over 31 years of experience as a ski patroller, Richard possesses extensive knowledge in construction design and land development.

Always on the lookout for new ventures, he is actively pursuing an expansion of his Route 100 property, which includes the acquisition of 171 Route 100. This project aims to create a mixed-use space featuring a café, office areas, and retail options.

Richard and his family are passionate about outdoor activities, including skiing, biking, hiking, boating, and fishing. He, along with his wife Laurie and their three dachshunds, resides in Wilmington, where they have raised their two sons, Jonathan and Nathan, amidst the scenic Green Mountains of Vermont. Jonathan currently lives in Breckenridge, Colorado, while Nathan is a student at the University of Vermont.

Windham County, VT Real Estate Market Analysis (Single Family Homes)

$765,002
Avg. Listing Price
From Richard's portfolio
3.8 / 2.9
Avg. Beds/Baths
Typical property size
2,679 sf
Avg. Square Footage
Interior living space
265
Active Listings
Current inventory

Windham County, Vermont represents one of the state's most dynamic and diverse real estate markets, stretching across the southeastern corner of the Green Mountain State. This region encompasses everything from bustling college towns to pristine rural retreats, creating a complex tapestry of property values and buyer preferences that challenges even experienced professionals to navigate effectively.

With 122 total actively licensed agents serving the county, all of whom maintain email contact information, the market demonstrates both healthy competition and comprehensive coverage across varied geographic terrain. This agent density reflects the region's appeal to out-of-state buyers, seasonal residents, and local families seeking everything from historic farmhouses to modern ski chalets.

Major Windham County, Vermont Real Estate Markets

Brattleboro anchors the county as its largest municipality and primary commercial hub, offering a unique blend of arts culture, Connecticut River access, and historic architecture that attracts both young professionals and retirees. The presence of several galleries, farmers markets, and a revitalized downtown core has sparked renewed interest in urban living within a small-town Vermont context, driving steady appreciation in walkable neighborhoods.

The Stratton and Mount Snow resort areas create distinct seasonal markets, with properties in Stratton, Dover, and Wilmington commanding premium prices for their ski access and mountain views. Meanwhile, towns like Putney and Newfane appeal to buyers seeking authentic Vermont village life, complete with covered bridges, general stores, and access to outdoor recreation without the resort pricing premium.

Market Dynamics and Geographic Complexity

Windham County's real estate landscape reflects Vermont's broader trend toward increased interest from urban refugees, particularly following remote work adoption during recent years. Properties with high-speed internet access and home office potential command surprising premiums, even in traditionally rural areas like Jamaica and Townshend, where buyers prioritize connectivity alongside pastoral settings.

The county's diverse topography creates distinct micro-markets with varying price points and buyer demographics. River valley properties along the Connecticut and West Rivers attract different buyers than hillside homes with mountain views, while historic village centers appeal to preservation-minded purchasers willing to invest in centuries-old architecture and the maintenance challenges that accompany authentic Vermont character.

Why Businesses Need Windham County, Vermont Agent Contact Data

Mortgage lenders, home inspectors, and insurance providers require comprehensive agent contact databases to effectively serve Windham County's geographically dispersed market. Given the county's mix of seasonal properties, primary residences, and investment homes, service providers must maintain relationships with agents across multiple market segments to capture referral opportunities and provide timely responses to client needs.

Title companies and real estate attorneys particularly benefit from direct agent communication channels, as Vermont's complex property history and rural land records often require collaborative research and problem-solving. With all 122 licensed agents maintaining active email addresses, businesses can efficiently distribute market updates, service offerings, and time-sensitive information across the entire professional network, ensuring comprehensive market coverage and strengthening referral partnerships.

Current Property Listings

As of 2/17/2026, Richard Caplan has 9 properties for sale in West Dover and surrounding areas.

$879,900

Listed 2025-03-05

7 Yodeling Ln
Dover, VT  05356

Beds: 4.0
Baths: 3.5
Sq Ft: 3,300
Lot: 21,780 sf
Single Family Map
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$539,000

Listed 2025-05-23

309 VT Route 100
Dover, VT  05356

Beds:
Baths:
Sq Ft:
Lot: 125,453 sf
Land Map
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$519,000

Listed 2025-08-12

16 Nutmeg Ln
Dover, VT  05356

Beds: 3.0
Baths: 2.0
Sq Ft: 2,000
Lot: 161,172 sf
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$2,889,000

Listed 2025-09-26

56 Handle Rd
Dover, VT  05356

Beds: 6.0
Baths: 5.5
Sq Ft: 6,400
Lot: 958,320 sf
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$2,195,000

Listed 2025-08-13

32 Steep Hill Rd
Wilmington, VT  05363

Beds: 5.0
Baths: 4.5
Sq Ft: 4,200
Lot: 871,200 sf
Single Family Map
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$449,000

Listed 2026-01-29

26 N Wind Rd
Wilmington, VT  05363

Beds: 3.0
Baths: 3.0
Sq Ft: 2,690
Lot: 69,696 sf
Single Family Map
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$389,000

Listed 2026-01-10

1 Frog Holw
Wilmington, VT  05363

Beds: 3.0
Baths: 2.0
Sq Ft: 1,200
Lot: 19,166 sf
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$429,000

Listed 2025-08-08

29 Mountainview Loop
Dover, VT  05356

Beds: 6.0
Baths: 3.0
Sq Ft: 2,500
Lot: 19,602 sf
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$389,000

Listed 2025-08-07

Handle Rd Lot E
Dover, VT  05356

Beds:
Baths:
Sq Ft:
Lot: 435,600 sf
Land Map
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Current Property Rentals

Richard Caplan currently has no rental properties available in West Dover and surrounding areas. Check back later.