23333 Four Chimneys Ln · Middleburg, VA 20117

$2,850,000

4 bd · 6.5 ba · 3,224 sqft · SingleFamily public records · 82 Days on market

Built 1995 7.57 ac lot $884/sqft · 52% above area Est $3657k · 22% under

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Why this score? — see what drove the D grade

The composite is a weighted blend of 9 inputs, each scored 0–100. Each bar is that input's sub-score; the figure is the points it added to the 100-point composite (weight × sub-score).

• ARV discount +15.0/15.0
• Appreciation +10.0/10.0
• Schools +6.7/10.0
• Livability +3.7/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Cash flow +0.0/30.0
• 1% rule +0.0/10.0
• DSCR +0.0/10.0

Listing remarks MLS

Located just over a mile east of historic Middleburg, Fox Hill Farm presents a rare opportunity to own a beautifully remodeled estate blending refined living with quintessential Virginia equestrian charm. Set on 7.6 picturesque acres, the property offers 6,547 finished square feet across the main residence and barn apartment, all accessed via paved and convenient Four Chimneys Lane off Little River Turnpike. The elegant two-level brick home features a desirable main-level primary suite with a spacious walk-in closet incorporating a second laundry, along with two additional bedrooms, each with its own en-suite bath. A gracious foyer opens to formal living and dining rooms, while the expansive gourmet kitchen—anchored by a grand center island—flows seamlessly into a bright breakfast area and light-filled great room with a striking Palladian window framing views of the paddocks and barn beyond. A side-loading two-car garage completes the main level. The recently finished lower level is an entertainer’s dream, offering a state-of-the-art home theater, recreation room, library/office, sitting room, full kitchen, wet bar, full hall bath, laundry, and two additional en-suite bedrooms. Walk-out access leads to a rear patio overlooking the landscaped grounds. A separate driveway serves the fully remodeled guest cottage and barn, currently a sought-after short-term rental, complete with an oversized detached garage. Additional highlights include a fenced kitchen garden, outdoor gathering area, and potential for an accessory dwelling (subject to approvals). A truly special Middleburg retreat.

Key facts

• 7.57 acre lot
• 4 garage spots
• Built 1995

What this means for you Summary

Snapshot

• This is a 4-bed/6.5-bath single-family listed at $2.85M.

Deal economics

• At list price, monthly cash flow is $-14k ($-171k/yr) — negative.
• To cash-flow at today's rent, offer at most $329k (88.4% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $400k (86.0% below list).
• Recommended offer: $329k (88.4% below list) — sets the bar for cash-flow.
• Cap rate 0.3% vs local median 0.4% in Middleburg — below-typical yield; the buyer is paying a premium for something (appreciation thesis, condition, location) that the cap rate doesn't capture.

Location & tenants

• Location reads 73/100 on livability (#174 in VA) — a middle-class / working-renter tenant base. Strengths: schools A+, crime A+, health & safety A+; Watch: housing C-, amenities F, commute F.
• Loudoun County Public School District (suburban): math 64% / reading 79% proficiency, ranked #7 of 131 in VA (top 5%) — strong family-tenant draw, lease renewals of 3-5y typical; only 12% free/reduced lunch — higher-income household profile.
• Market conditions: 39 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 3,317 units permitted in Loudoun County in 2024 (1,818 in 5+ unit buildings).

Forward outlook

• In year one you build about $305k of equity ($20k loan paydown + $285k appreciation (10.0% local appreciation)).
• Loudoun County population projected at +65% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• By year 2, paydown + projected appreciation supports a ~$490k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 82 days — a 6% lower offer ($2.68M) is reasonable based on typical stale-listing flexibility.
• 9 sale attempts since 20y ago with the ask held roughly flat each time — persistent listings suggest the price (not the market) is what's stuck; bring a comps-based counter.
• Current owner paid $1.15M; list at $2.85M implies a 148% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Climate carrying-cost: moderate wildfire risk; extreme-heat days projected 7→16/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $329,369 (88.4% below list)

Questions for the listing agent

1. What do current leases actually rent for vs. the listed asking? Can we see a recent rent roll and the last 12 months of T-12 income?
2. It's been on market 82 days. Have you received any prior offers? Is the seller open to a 88% concession, seller financing, or rate buy-down credit?
3. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. Schools are A-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
6. The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
7. What's the average days-on-market for RENTAL listings here right now (not sales)? A rising rental-DOM trend means longer vacancies and softer asking-rent achievability than the comps imply.
8. What's the recent tenant-quality profile in this submarket — average credit score on applications, eviction rate, late-payment / NSF rate, and stable-employment percentage? A property-management company in the area should have these aggregated.
9. How much new for-sale + rental construction is in the pipeline within 1–3 miles? Heavy new supply typically softens prices + rents 12–24 months out; constrained supply supports both.

Investment metrics

• 1% rule: 0.14% ✗
• Cap rate: 0.29%
• Cash-on-cash: -21.46%
• DSCR: 0.05
• GRM: 59.4

CMA / ARV

• ARV (median comp): $3,657,414
• List price: $2,850,000
• Delta: -22.08%
• Verdict: UNDERPRICED
• Comps: 2 within 1.0 mi

Projected returns pro-forma

10.0% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 9.6%
• Equity multiple: 1.80×
• Total profit: $642,070
• Equity at exit: $2,567,506

10-year hold

• IRR: 11.0%
• Equity multiple: 4.26×
• Total profit: $2,602,801
• Equity at exit: $5,536,923

Cash invested: $798,000 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 55 Moderately Landlord-Leaning
• State Virginia: 55 Moderately Landlord-Leaning · D+2
• County: — inherits STATE
• City: — inherits STATE

VRLTA gives some tenant protections; Northern Virginia courts slower; rural VA landlord-leaning.

Methodology + full state rankings →

ZIP-level market 20117

• Home prices YoY: 10.9%
• Active inventory: 39
• Price-to-rent: 59.4×

Monthly cashflow live

• Estimated rent: $4,000 medium
• Mortgage (P&I): −$14,946
• Tax from tax record: −$1,296 /mo · $15,546/yr
• Insurance: −$1,188
• HOA: −$0
• Vacancy / Maint / Mgmt: −$840
• Net cashflow: $-14,269

Break-even live

Break-even rent $22,062

Max offer price $329,369

Occupancy floor —

Sensitivity live

Price	-10% $-12,655	-5% $-13,462	+0% $-14,269	+5% $-15,075	+10% $-15,882
Rent	-10% $-14,585	-5% $-14,427	+0% $-14,269	+5% $-14,111	+10% $-13,953
Rate	-1.0pp $-12,833	-0.5pp $-13,544	base $-14,269	+0.5pp $-15,007	+1.0pp $-15,759

UW: 25.0% down · 7.5% · 30yr · 1.5% tax · 5.0% vac · 8.0% maint · 8.0% mgmt

Financing live

Cash to close

• Down payment: $712,500
• Closing costs: $85,500
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
23171 Carters Farm Ln Middleburg, VA	4.0	3.0	2646	$4,000	$1.51	11d	1	0.38mi

Listing history 42 events

1. 2026-06-18
   days on market $2,850,000 Active 82 DOM
2. 2026-06-17
   days on market $2,850,000 Active 81 DOM
3. 2026-06-16
   days on market $2,850,000 Active 80 DOM
4. 2026-06-15
   days on market $2,850,000 Active 79 DOM
5. 2026-06-13
   days on market $2,850,000 Active 77 DOM
6. 2026-06-09
   days on market $2,850,000 Active 73 DOM
7. 2026-06-08
   days on market $2,850,000 Active 72 DOM
8. 2026-06-07
   days on market $2,850,000 Active 71 DOM
9. 2026-06-04
   days on market $2,850,000 Active 68 DOM
10. 2026-06-03
    days on market $2,850,000 Active 67 DOM
11. 2026-06-02
    days on market $2,850,000 Active 66 DOM
12. 2026-06-01
    days on market $2,850,000 Active 65 DOM
13. 2026-05-31
    days on market $2,850,000 Active 64 DOM
14. 2026-03-29
    listed $2,850,000 Active 1626-char remark

    Show marketing remark (1626 chars)

    Located just over a mile east of historic Middleburg, Fox Hill Farm presents a rare opportunity to own a beautifully remodeled estate blending refined living with quintessential Virginia equestrian charm. Set on 7.6 picturesque acres, the property offers 6,547 finished square feet across the main residence and barn apartment, all accessed via paved and convenient Four Chimneys Lane off Little River Turnpike. The elegant two-level brick home features a desirable main-level primary suite with a spacious walk-in closet incorporating a second laundry, along with two additional bedrooms, each with its own en-suite bath. A gracious foyer opens to formal living and dining rooms, while the expansive gourmet kitchen—anchored by a grand center island—flows seamlessly into a bright breakfast area and light-filled great room with a striking Palladian window framing views of the paddocks and barn beyond. A side-loading two-car garage completes the main level. The recently finished lower level is an entertainer’s dream, offering a state-of-the-art home theater, recreation room, library/office, sitting room, full kitchen, wet bar, full hall bath, laundry, and two additional en-suite bedrooms. Walk-out access leads to a rear patio overlooking the landscaped grounds. A separate driveway serves the fully remodeled guest cottage and barn, currently a sought-after short-term rental, complete with an oversized detached garage. Additional highlights include a fenced kitchen garden, outdoor gathering area, and potential for an accessory dwelling (subject to approvals). A truly special Middleburg retreat.

15. 2026-03-24
    historical $2,850,000 1626-char remark

    Show marketing remark (1626 chars)

    Located just over a mile east of historic Middleburg, Fox Hill Farm presents a rare opportunity to own a beautifully remodeled estate blending refined living with quintessential Virginia equestrian charm. Set on 7.6 picturesque acres, the property offers 6,547 finished square feet across the main residence and barn apartment, all accessed via paved and convenient Four Chimneys Lane off Little River Turnpike. The elegant two-level brick home features a desirable main-level primary suite with a spacious walk-in closet incorporating a second laundry, along with two additional bedrooms, each with its own en-suite bath. A gracious foyer opens to formal living and dining rooms, while the expansive gourmet kitchen—anchored by a grand center island—flows seamlessly into a bright breakfast area and light-filled great room with a striking Palladian window framing views of the paddocks and barn beyond. A side-loading two-car garage completes the main level. The recently finished lower level is an entertainer’s dream, offering a state-of-the-art home theater, recreation room, library/office, sitting room, full kitchen, wet bar, full hall bath, laundry, and two additional en-suite bedrooms. Walk-out access leads to a rear patio overlooking the landscaped grounds. A separate driveway serves the fully remodeled guest cottage and barn, currently a sought-after short-term rental, complete with an oversized detached garage. Additional highlights include a fenced kitchen garden, outdoor gathering area, and potential for an accessory dwelling (subject to approvals). A truly special Middleburg retreat.

16. 2025-08-31
    historical
17. 2025-06-04
    price $2,950,000
18. 2025-05-12
    price $3,095,000
19. 2025-04-17
    listed $3,249,000 Active
20. 2025-03-08
    historical
21. 2024-12-03
    historical
22. 2024-11-03
    listed $3,800,000 Active
23. 2024-10-04
    historical
24. 2022-01-03
    soldstatus $1,150,000 Closed
25. 2021-12-29
    soldstatus $1,150,000
26. 2021-10-26
    historical Active Under Contract
27. 2021-09-05
    listed $1,250,000 Active
28. 2010-01-11
    soldstatus $800,000 Sold
29. 2010-01-11
    soldstatus $800,000
30. 2009-12-18
    status Contract
31. 2009-12-10
    historical
32. 2009-11-28
    status Active
33. 2009-11-28
    historical Expired
34. 2009-08-08
    status
35. 2009-08-08
    historical
36. 2009-07-30
    listed $999,950 Active
37. 2008-07-16
    listed $999,950
38. 2006-12-02
    historical
39. 2006-02-01
    listed
40. 1994-06-17
    soldstatus $130,000
41. 1993-09-28
    soldstatus $99,000
42. 1992-07-06
    soldstatus $280,000

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Tax reassessment forecast VA · Resets to sale price

• Current annual tax: $15,546 · $1,296/mo
• Projected year-2 tax: $23,370 · $1,948/mo
• Expected delta: +$7,824/yr (+$652/mo · 50.3%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 5/10 Major
• 🌡 Heat 6/10 Major 7 d/yr ≥104°F today · 16 d/yr by 30 yrs out
• 💨 Wind 3/10 Moderate 7% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $48,000
• − Mortgage interest: −$159,644
• − Property taxes: −$15,546
• − Insurance: −$14,250
• − Repairs & maintenance: −$3,840
• − Management: −$3,840
• − Depreciation: −$82,909
• Taxable loss: −$232,030
• Est. tax savings @ 24.0%: +$55,687
• After-tax cash flow: $-115,538/yr

For passive investors: Depreciation is non-cash, so a rental often shows a tax loss while cash-flowing — sheltering income. Rental losses are passive: they offset passive income freely, and up to $25,000/yr can offset ordinary (W-2) income if you actively participate and your MAGI is under $100k (phasing out to $0 by $150k); unused losses carry forward. On sale, claimed depreciation is recaptured at up to 25%, and gains may owe capital-gains tax (a 1031 exchange can defer both). Figures are a year-1 estimate at your 24.0% rate — not tax advice; consult a CPA.

Schools (NCES district)

• District: Loudoun County Public School District
• NCES district ID: 5102250
• Math proficiency: 64% ▼ -22.00%
• Reading proficiency: 79% ▼ -5.00%
• Median HH income: $121,927
• Composite: 67.43/100
• National rank: #379
• State rank: #7 of 131 in VA

Livability — Middleburg

• Score: 73/100
• State rank: #174
• US rank: #5392

Category grades

Amenities F Commute F Cost of living F Crime A+ Employment B Housing C- Health & safety A+ User ratings A+

Schools grade is shown separately in the Schools card above.

Census & demographics

• Population (ZIP): 3,248

Population outlook (Loudoun County) Hauer SSP2

• Today (2025): 503,590 people
• By 2030: 568,852 · +13.0%
• By 2040: 701,480 · +39.3%
• By 2050: 828,841 · +64.6%
• By 2075: 1,105,645 · +119.6%
• By 2100: 1,265,472 · +151.3%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (84%)
• Race & ethnicity: White 84% Hispanic / Latino 9% Black 7% Two or more races 3%
• Hispanic origin (detail): Cuban 1%
• Common ancestry: Italian 8% Slovak 3% Romanian 3%
• Foreign-born: 6% · Canada
• Languages at home: 92% English-only · Spanish 6% French/Haitian/Cajun 1%

Political lean MEDSL · Loudoun

• 2024 margin: D (+16.3) · D 56.6% · R 40.4% · Other 3.0%
• 2008→2024 swing: +8.0pp toward D · 2008: 8.2pp · 2024: 16.3pp
• All cycles: 2024: D+16.3 2020: D+25.0 2016: D+16.8 2012: D+4.5 2008: D+8.2

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 36.93%
• Current HPI: 375.846
• Rent YoY: —
• Metro: —
• State GDP YoY: ▲ 2.40%
• F500 in state: 50

Industry mix (Fortune 500 HQ in VA)

Industry	F500 HQs	Revenue
▸Aerospace / Defense	4	$236B
▸Technology / Defense	3	$32B
▸Financial Services	2	$176B
▸Utilities	2	$27B
▸Insurance	2	$25B
▸Technology	2	$15B

Price history

+917.9% since first listed

29 events — show timeline

• 2026-03-29 Listed $2,850,000 BRIGHT MLS
• 2026-03-24 Coming Soon $2,850,000 BRIGHT MLS
• 2025-08-31 Listing Removed — BRIGHT MLS
• 2025-06-04 Price Changed $2,950,000 BRIGHT MLS
• 2025-05-12 Price Changed $3,095,000 BRIGHT MLS
• 2025-04-17 Listed $3,249,000 BRIGHT MLS
• 2025-03-08 Coming Soon — BRIGHT MLS
• 2024-12-03 Listing Removed — BRIGHT MLS
• 2024-11-03 Listed $3,800,000 BRIGHT MLS
• 2024-10-04 Coming Soon — BRIGHT MLS
• 2022-01-03 Sold (MLS) $1,150,000 BRIGHT MLS
• 2021-12-29 Sold (Public Records) $1,150,000 Public Records
• 2021-10-26 Contingent — BRIGHT MLS
• 2021-09-05 Listed $1,250,000 BRIGHT MLS
• 2010-01-11 Sold (MLS) $800,000 BRIGHT MLS
• 2010-01-11 Sold (MLS) $800,000 MRIS
• 2009-12-18 Pending — MRIS
• 2009-12-10 Listing Removed — BRIGHT MLS
• 2009-11-28 Relisted — MRIS
• 2009-11-28 Delisted — MRIS
• 2009-08-08 Relisted — MRIS
• 2009-08-08 Delisted — MRIS
• 2009-07-30 Listed $999,950 MRIS
• 2008-07-16 Listed $999,950 BRIGHT MLS
• 2006-12-02 Delisted — MRIS
• 2006-02-01 Listed — MRIS
• 1994-06-17 Sold (Public Records) $130,000 Public Records
• 1993-09-28 Sold (Public Records) $99,000 Public Records
• 1992-07-06 Sold (Public Records) $280,000 Public Records

Property tax history

+2.0%/yr

Latest (2025): $15,546 · +41.0% YoY. Source: county tax records.