# 42277 CHESTNUT HILL Lane, Leesburg, VA 20176 > **TL;DR:** 4bd/3ba single family, $950,000 ($413/sqft), built 1900, 2,300 sqft. > A/C. Est. $5,081/mo. Listed 81 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $950,000 | | Price/sqft | $413 | | Bedrooms | 4 | | Bathrooms | 3 full | | Square Feet | 2,300 | | Year Built | 1900 | | Lot Size | 871,200 sqft (20.00 acres) | | Stories | 2 | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 81 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $4,804 | | Estimated Insurance | $277 | | **Total** | **$5,081** | ## Nearby Schools - **Elementary:** LUCKETTS - **Middle:** SMART'S MILL - **High:** TUSCARORA ## Key Amenities - A/C ## Property Highlights - Built in 1900 - 20.00 acre lot - 2 stories ## Description ### Agent Description CHARMING FARMHOUSE ON 20 PRIVATE ACRES WITH BARNS, POND & VIEWS! Nestled at the end of a long private gravel driveway lined with towering pines, this charming two-level Colonial farmhouse is tucked away on a breathtaking 20-acre rural property in the sought-after Chestnut Hill farming community. Offering privacy, tranquility, and endless possibilities for farming, horses, hobbies, or simply enjoying country living, this exceptional property combines comfortable living with ultimate privacy. Recently refreshed with neutral paint throughout and new luxury vinyl plank flooring on the main level, the home features over 2,300 square feet of living space. A welcoming full front porch provides the perfect place to relax and take in the pastoral surroundings, including views of the neighboring historic Chestnut Hill Mansion! Inside, a two-story foyer welcomes you into the home. The main level offers a convenient bedroom and/or office and full bath, a spacious living room, and a large country kitchen that opens seamlessly to both the screened porch and expansive rear deck. The front porch connects to a side porch, creating multiple outdoor spaces to enjoy the peaceful setting and sweeping pasture views in every direction. The upper level features a spacious primary suite with vaulted ceilings, a walk-in closet, and a private bath with separate shower and soaking tub. Two additional bedrooms, a secondary full bath, and an upper-level laundry room provide added convenience. The property is truly a rare rural retreat! A private pond sits beyond the home, while several outbuildings provide incredible flexibility for agricultural, equestrian, storage, workshop, or recreational uses. Highlights include a picturesque bank barn offering 2,280 square feet with unforgettable panoramic farm views, a 2,000-square-foot common stable, and a 1,680-square-foot three-wall storage shed, and two additional storage sheds. With no HOA and abundant open space, the opportunities are endless. Farm, fish, raise animals, cultivate gardens, pursue your hobbies, or simply enjoy the serenity and beauty of Loudoun County's countryside. House and property sold strictly as-is. Ideally located just off James Monroe Highway, the property offers convenient access to major commuter routes while remaining worlds away from the hustle and bustle. Enjoy nearby farmers markets, roadside farm stands, and the charm of Lucketts Village. Historic downtown Leesburg, with its vibrant dining, shopping, and entertainment scene, is just minutes away. Easy access to Maryland makes this an exceptional location for commuters seeking the best of rural living without sacrificing convenience. A rare opportunity to own a private farmstead in one of Loudoun County's most picturesque settings. Property sold in As-Is condition, Seller prefers Entitle First Title in Leesburg. ## Location - **Address:** 42277 CHESTNUT HILL Lane, Leesburg, VA 20176 - **County:** LOUDOUN - **Neighborhood:** CHESTNUT HILL FARMS - **Coordinates:** 39.24716221, -77.53752371 - **Google Maps:** https://www.google.com/maps?q=39.24716221,-77.53752371 ## Listing Agent - **Name:** Karen Ann Wenner Cooper · **License:** 0225065935 - **Brokerage:** REAL BROKER LLC - **Broker Phone:** (202) 335-7325 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/42277-Chestnut-Hill-Ln_Leesburg_VA_20176_M69384-40309?f=listhub&s=TRENDPA&m=VALO2125098&c=propsimple) ## Photos ![42277 CHESTNUT HILL Lane - Photo 1](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f2625720088r.jpg) ![42277 CHESTNUT HILL Lane - Photo 2](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1311557579r.jpg) ![42277 CHESTNUT HILL Lane - Photo 3](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1998757409r.jpg) ![42277 CHESTNUT HILL Lane - Photo 4](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1542058279r.jpg) ![42277 CHESTNUT HILL Lane - Photo 5](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f4033327442r.jpg) ![42277 CHESTNUT HILL Lane - Photo 6](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f208321459r.jpg) ![42277 CHESTNUT HILL Lane - Photo 7](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f3250785325r.jpg) ![42277 CHESTNUT HILL Lane - Photo 8](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f2578152202r.jpg) ![42277 CHESTNUT HILL Lane - Photo 9](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f4041095684r.jpg) ![42277 CHESTNUT HILL Lane - Photo 10](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f2673631802r.jpg) ![42277 CHESTNUT HILL Lane - Photo 11](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f910536355r.jpg) ![42277 CHESTNUT HILL Lane - Photo 12](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1437302404r.jpg) ![42277 CHESTNUT HILL Lane - Photo 13](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1194737390r.jpg) ![42277 CHESTNUT HILL Lane - Photo 14](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f2417290112r.jpg) ![42277 CHESTNUT HILL Lane - Photo 15](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1312868291r.jpg) ![42277 CHESTNUT HILL Lane - Photo 16](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1372808474r.jpg) ![42277 CHESTNUT HILL Lane - Photo 17](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f3242819904r.jpg) ![42277 CHESTNUT HILL Lane - Photo 18](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f2222702013r.jpg) ![42277 CHESTNUT HILL Lane - Photo 19](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f2413816325r.jpg) ![42277 CHESTNUT HILL Lane - Photo 20](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f65170049r.jpg) ![42277 CHESTNUT HILL Lane - Photo 21](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f3350507722r.jpg) ![42277 CHESTNUT HILL Lane - Photo 22](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f4077626277r.jpg) ![42277 CHESTNUT HILL Lane - Photo 23](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f2396103557r.jpg) ![42277 CHESTNUT HILL Lane - Photo 24](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f2765016060r.jpg) ![42277 CHESTNUT HILL Lane - Photo 25](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1893859735r.jpg) ![42277 CHESTNUT HILL Lane - Photo 26](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f3375666583r.jpg) ![42277 CHESTNUT HILL Lane - Photo 27](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f2759690519r.jpg) ![42277 CHESTNUT HILL Lane - Photo 28](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f727993736r.jpg) ![42277 CHESTNUT HILL Lane - Photo 29](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f630352162r.jpg) ![42277 CHESTNUT HILL Lane - Photo 30](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f353719195r.jpg) ![42277 CHESTNUT HILL Lane - Photo 31](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f2897009032r.jpg) ![42277 CHESTNUT HILL Lane - Photo 32](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f396514089r.jpg) ![42277 CHESTNUT HILL Lane - Photo 33](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f681060480r.jpg) ![42277 CHESTNUT HILL Lane - Photo 34](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f3834702983r.jpg) ![42277 CHESTNUT HILL Lane - Photo 35](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1486954373r.jpg) ![42277 CHESTNUT HILL Lane - Photo 36](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f2060114807r.jpg) ![42277 CHESTNUT HILL Lane - Photo 37](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f918892719r.jpg) ![42277 CHESTNUT HILL Lane - Photo 38](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1746930499r.jpg) ![42277 CHESTNUT HILL Lane - Photo 39](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f614198491r.jpg) ![42277 CHESTNUT HILL Lane - Photo 40](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1301106137r.jpg) ![42277 CHESTNUT HILL Lane - Photo 41](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f860086443r.jpg) ![42277 CHESTNUT HILL Lane - Photo 42](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f2798317658r.jpg) ![42277 CHESTNUT HILL Lane - Photo 43](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1365629731r.jpg) ![42277 CHESTNUT HILL Lane - Photo 44](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1500155928r.jpg) ![42277 CHESTNUT HILL Lane - Photo 45](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f3250403866r.jpg) ![42277 CHESTNUT HILL Lane - Photo 46](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f3587042520r.jpg) ![42277 CHESTNUT HILL Lane - Photo 47](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1929408076r.jpg) ![42277 CHESTNUT HILL Lane - Photo 48](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1865377023r.jpg) ![42277 CHESTNUT HILL Lane - Photo 49](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f1622440554r.jpg) ![42277 CHESTNUT HILL Lane - Photo 50](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f3771610691r.jpg) ![42277 CHESTNUT HILL Lane - Photo 51](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f3389857663r.jpg) ![42277 CHESTNUT HILL Lane - Photo 52](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f811899989r.jpg) ![42277 CHESTNUT HILL Lane - Photo 53](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f273082074r.jpg) ![42277 CHESTNUT HILL Lane - Photo 54](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f63843909r.jpg) ![42277 CHESTNUT HILL Lane - Photo 55](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f3480857443r.jpg) ![42277 CHESTNUT HILL Lane - Photo 56](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f4202836470r.jpg) ![42277 CHESTNUT HILL Lane - Photo 57](http://lh.rdcpix.com/c3afc3dcd2955866928469c80c5d690fl-f2725438795r.jpg) --- **MLS#:** VALO2125098 | **Updated:** 2026-10-28 **Source:** listhub *Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://staging.propertysimple.ai/listing/42277-chestnut-hill-lane-leesburg-va-20176-f56a1cea16684f16b1d1a7bc1c19cc5f) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/42277-chestnut-hill-lane-leesburg-va-20176-f56a1cea16684f16b1d1a7bc1c19cc5f#listing", "url": "https://staging.propertysimple.ai/listing/42277-chestnut-hill-lane-leesburg-va-20176-f56a1cea16684f16b1d1a7bc1c19cc5f", "name": "42277 CHESTNUT HILL Lane, Leesburg, VA 20176", "description": "CHARMING FARMHOUSE ON 20 PRIVATE ACRES WITH BARNS, POND & VIEWS! Nestled at the end of a long private gravel driveway lined with towering pines, this charming two-level Colonial farmhouse is tucked away on a breathtaking 20-acre rural property in the sought-after Chestnut Hill farming community. Offering privacy, tranquility, and endless possibilities for farming, horses, hobbies, or simply enjoying country living, this exceptional property combines comfortable living with ultimate privacy. Recently refreshed with neutral paint throughout and new luxury vinyl plank flooring on the main level, the home features over 2,300 square feet of living space. A welcoming full front porch provides the perfect place to relax and take in the pastoral surroundings, including views of the neighboring historic Chestnut Hill Mansion! Inside, a two-story foyer welcomes you into the home. The main level offers a convenient bedroom and/or office and full bath, a spacious living room, and a large country kitchen that opens seamlessly to both the screened porch and expansive rear deck. The front porch connects to a side porch, creating multiple outdoor spaces to enjoy the peaceful setting and sweeping pasture views in every direction. The upper level features a spacious primary suite with vaulted ceilings, a walk-in closet, and a private bath with separate shower and soaking tub. Two additional bedrooms, a secondary full bath, and an upper-level laundry room provide added convenience. The property is truly a rare rural retreat! A private pond sits beyond the home, while several outbuildings provide incredible flexibility for agricultural, equestrian, storage, workshop, or recreational uses. Highlights include a picturesque bank barn offering 2,280 square feet with unforgettable panoramic farm views, a 2,000-square-foot common stable, and a 1,680-square-foot three-wall storage shed, and two additional storage sheds. With no HOA and abundant open space, the opportunities are endless. Farm, fish, raise animals, cultivate gardens, pursue your hobbies, or simply enjoy the serenity and beauty of Loudoun County's countryside. House and property sold strictly as-is. Ideally located just off James Monroe Highway, the property offers convenient access to major commuter routes while remaining worlds away from the hustle and bustle. Enjoy nearby farmers markets, roadside farm stands, and the charm of Lucketts Village. Historic downtown Leesburg, with its vibrant dining, shopping, and entertainment scene, is just minutes away. Easy access to Maryland makes this an exceptional location for commuters seeking the best of rural living without sacrificing convenience. A rare opportunity to own a private farmstead in one of Loudoun County's most picturesque settings. 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