16 Doubling Rd · Greenwich, CT 06830

$19,950,000

6 bd · 9.5 ba · 11,323 sqft · SingleFamily public records · 51 Days on market

Built 2026 2.93 ac lot $1762/sqft · at area comps Est $27500k · 27% 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 +8.4/10.0
• Schools +6.6/10.0
• Livability +4.0/5.0
• Rent growth +3.3/5.0
• 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

Live the Good Life on Doubling Road. Conveniently located near central Greenwich, this stone and shingle style 7 bedrooms/8.3 baths home, designed by Austin Patterson Disston and built by Stone Harbour builders, is commandingly set on 2.93 park-like acres with views overlooking the Greenwich Country Club golf course and Long Island Sound on the horizon. The location is minutes to Greenwich Avenue, Private & Public Schools, Merritt Parkway, I95, and Metro-North Railroad. The estate includes the four level 10,190 sf main house with attached 2 car garage, 5 car detached temperature controlled garage with 2 car lifts already plumbed and wired for a 2nd floor apartment, a heated pool plus separate jacuzzi spa, and a pool gazebo with enclosed outdoor shower. The grand double height entrance hall is welcoming and is the introduction to the formal living room with fireplace, mahogany paneled library/office with fireplace, formal dining room, gourmet kitchen with walk-in pantry, family room with fireplace, attached screened gazebo, and exercise area/1st floor master suite. The spacious mud room is accessed by a second front entrance, the garage and back door, plus formal and informal powder rooms. Bring the light and beauty from the outside in with an abundance of French doors throughout. From the expansive covered cedar porch, blue stone patios, master bedroom and third floor balcony, enjoy the changing views of the professionally orchestrated landscaped grounds and the high views over the country club golf course artistically framed by privacy providing mature trees. The gracefully ascending staircase gives a panoramic view of the entrance hall and second floor hallway. The second floor includes the master bedroom suite with luxurious bathroom consisting of steam shower and jacuzzi tub, vanity area, walk-in closet/lounge, and private balcony. In addition, there are three light filled en suite double bedrooms and an impressive upstairs family room with double height ceiling. On the third floor is a very large common room with wet bar and balcony giving a bird's eye perspective. The inhabitants of the two double bedrooms with two full baths will enjoy their own private living space. The lower level offers perfect rooms for entertaining. Open the pocket doors between the theatre and billiard/bar room for Super Bowl parties or close them for intimate movie viewing. The 3,000 bottle walk-in wine cellar will sufficiently accommodate your collection. Have peace of mind with the secure room equipped with separate security lock system. This level also has an expansive multi purpose/game room, laundry, full bath, half bath, and plenty of storage rooms and closets. The grounds surrounding this home have a variety of memory making places. Whatever you're looking for, relaxation or activity. Take pleasure in the feeling of an outdoor shower after swimming laps in the pool and time in the hot tub, practice your yoga sunrise salutations from the covered porch, or simply read a book under a tree. Shoot some hoops, kick or throw a ball on the playing fields, sit around the fire pit singing and/or telling stories, or play king of the grill. Join the Greenwich Country Club and go across the street to participate in activities offered such as tennis, golf, platform tennis, swimming, bowling, and dining. Life is good.

Key facts

• Full house generator
• Panoramic views
• Pool

Tags

• PRIVATE ELEVATED ACRES
• PANORAMIC VIEWS
• ADVANCED TECHNOLOGY SYSTEMS
• SMART-HOME INFRASTRUCTURE
• POOL
• FULL HOUSE GENERATOR

Property features AI

Finance

• Other: Approximately 16,154 total building area (architect source); Zoning: RA-1

Exterior

• Parking: 7 garage spaces; Garage door opener; Electric gate
• Security: Security system; Electric gate
• Utilities: Public water
• Home design: Single family residence; Facing unknown; Entry level unknown
• Construction: Built in 2026; Stucco construction; Composition and slate roof
• Exterior features: Private pool; Adjacent to golf course; Level lot; Waterfront with waterviews; Carriage house; Generator; Security system

Interior

• Bathrooms: 9 full bathrooms; 4 half bathrooms (13 total bathrooms listed)
• Heating & cooling: Central air conditioning; Natural gas heating; Radiant heating
• Interior features: Back stairs; Finished basement

What this means for you Summary

Snapshot

• This is a 6-bed/9.5-bath single-family listed at $19.95M.

Deal economics

• At list price, monthly cash flow is $-112k ($-1.35M/yr) — negative.
• To cash-flow at today's rent, offer at most $683k (96.6% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $597k (97.0% below list).
• Recommended offer: $597k (97.0% below list) — sets the bar for 1% rule.
• Cap rate -0.5% vs local median 1.1% in Greenwich — 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 80/100 on livability (#23 in CT, #1,655 nationally) — a professional / high-income tenant draw. Strengths: crime A+, employment A+, health & safety A+; Watch: amenities D, cost of living F.
• Greenwich School District (suburban): math 64% / reading 73% proficiency, ranked #12 of 153 in CT (top 8%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 11% free/reduced lunch — higher-income household profile.
• Zoned schools: North Street School (math 72% / reading 82%, grade A, #28 of 553 statewide, top 7%, 387 students, 4% FRL); Central Middle School (math 60% / reading 71%, grade A-, #26 of 175 statewide, top 16%, 506 students, 18% FRL); Greenwich High School (math 59% / reading 78%, grade B, #23 of 194 statewide, top 12%, 2,668 students, 20% FRL) — zoned schools at 14% FRL track the district average.
• Market conditions: Rents rising (+3.4%/yr); 128 active listings in the ZIP; 2 comparable units currently listed for rent nearby; high-income renter base; 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).
• At $5,972/mo this rent would consume 49% of the median local household income ($147k/yr) (locally 1088% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• In year one you build about $1.51M of equity ($138k loan paydown + $1.38M appreciation (6.9% local appreciation)).
• By year 2, paydown + projected appreciation supports a ~$2.42M cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 51 days — a 3% lower offer ($19.35M) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 8y ago; this cycle's ask has dropped $4.55M (19%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $8.35M; list at $19.95M implies a 139% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Climate carrying-cost: major wind risk, 67% chance of damaging wind over 30y; extreme-heat days projected 7→15/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $597,203 (97.0% 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 51 days. Have you received any prior offers? Is the seller open to a 97% concession, seller financing, or rate buy-down credit?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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?
5. 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?
6. 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.
7. 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.
8. 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: 0.03% ✗
• Cap rate: -0.46%
• Cash-on-cash: -24.11%
• DSCR: -0.07
• GRM: 278.4

CMA / ARV

• ARV (median comp): $27,500,000
• List price: $19,950,000
• Delta: -27.45%
• Verdict: UNDERPRICED
• Comps: 1 within 2.0 mi

Projected returns pro-forma

6.89% appreciation · 3.36% rent growth · sell at horizon

5-year hold

• IRR: -0.8%
• Equity multiple: 0.94×
• Total profit: $-323,452
• Equity at exit: $13,684,018

10-year hold

• IRR: 3.3%
• Equity multiple: 1.79×
• Total profit: $4,400,054
• Equity at exit: $25,866,921

Cash invested: $5,586,000 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 27 Tenant-Leaning
• State Connecticut: 27 Tenant-Leaning · D+7
• County: — inherits STATE
• City: — inherits STATE

Strong tenant statutes; rent commissions in some towns; courts slow especially in cities.

Methodology + full state rankings →

ZIP-level market 06830

• Home prices YoY: 4.1%
• Rents YoY: 3.4%
• Active inventory: 128
• Price-to-rent: 278.4×

Monthly cashflow live

• Estimated rent: $5,972 medium
• Mortgage (P&I): −$104,620
• Tax from tax record: −$3,999 /mo · $47,986/yr
• Insurance: −$8,312
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,254
• Net cashflow: $-112,213

Break-even live

Break-even rent $148,014

Max offer price $682,688

Occupancy floor —

Sensitivity live

Price	-10% $-100,920	-5% $-106,567	+0% $-112,213	+5% $-117,860	+10% $-123,507
Rent	-10% $-112,685	-5% $-112,449	+0% $-112,213	+5% $-111,978	+10% $-111,742
Rate	-1.0pp $-102,167	-0.5pp $-107,139	base $-112,213	+0.5pp $-117,383	+1.0pp $-122,642

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: $4,987,500
• Closing costs: $598,500
• Reserves months: —
• Total cash needed: —

Rent comps 2 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
425 N Maple Ave Greenwich, CT	6.0	8.5	10081	$60,000	$5.95	45d	1	1.11mi
59 Cat Rock Rd Cos Cob, CT	6.0	7.5	8482	$39,500	$4.66	4d	1	1.24mi

Listing history 26 events

1. 2026-06-21
   days on market $19,950,000 Active 51 DOM
2. 2026-06-18
   days on market $19,950,000 Active 48 DOM
3. 2026-06-17
   days on market $19,950,000 Active 47 DOM
4. 2026-06-16
   days on market $19,950,000 Active 46 DOM
5. 2026-06-15
   days on market $19,950,000 Active 45 DOM
6. 2026-06-13
   pricedays on market $19,950,000 Active 43 DOM
7. 2026-06-10
   days on market $24,500,000 Active 40 DOM
8. 2026-06-09
   days on market $24,500,000 Active 39 DOM
9. 2026-06-08
   days on market $24,500,000 Active 38 DOM
10. 2026-06-07
    days on market $24,500,000 Active 37 DOM
11. 2026-06-03
    days on market $24,500,000 Active 33 DOM
12. 2026-06-03
    days on market $24,500,000 Active 32 DOM
13. 2026-06-01
    days on market $24,500,000 Active 31 DOM
14. 2026-05-31
    days on market $24,500,000 Active 30 DOM
15. 2026-05-01
    listed $24,500,000 Active 809-char remark
16. 2019-09-24
    soldstatus $8,347,000 Closed 3357-char remark

    Show marketing remark (3357 chars)

    Live the Good Life on Doubling Road. Conveniently located near central Greenwich, this stone and shingle style 7 bedrooms/8.3 baths home, designed by Austin Patterson Disston and built by Stone Harbour builders, is commandingly set on 2.93 park-like acres with views overlooking the Greenwich Country Club golf course and Long Island Sound on the horizon. The location is minutes to Greenwich Avenue, Private & Public Schools, Merritt Parkway, I95, and Metro-North Railroad. The estate includes the four level 10,190 sf main house with attached 2 car garage, 5 car detached temperature controlled garage with 2 car lifts already plumbed and wired for a 2nd floor apartment, a heated pool plus separate jacuzzi spa, and a pool gazebo with enclosed outdoor shower. The grand double height entrance hall is welcoming and is the introduction to the formal living room with fireplace, mahogany paneled library/office with fireplace, formal dining room, gourmet kitchen with walk-in pantry, family room with fireplace, attached screened gazebo, and exercise area/1st floor master suite. The spacious mud room is accessed by a second front entrance, the garage and back door, plus formal and informal powder rooms. Bring the light and beauty from the outside in with an abundance of French doors throughout. From the expansive covered cedar porch, blue stone patios, master bedroom and third floor balcony, enjoy the changing views of the professionally orchestrated landscaped grounds and the high views over the country club golf course artistically framed by privacy providing mature trees. The gracefully ascending staircase gives a panoramic view of the entrance hall and second floor hallway. The second floor includes the master bedroom suite with luxurious bathroom consisting of steam shower and jacuzzi tub, vanity area, walk-in closet/lounge, and private balcony. In addition, there are three light filled en suite double bedrooms and an impressive upstairs family room with double height ceiling. On the third floor is a very large common room with wet bar and balcony giving a bird's eye perspective. The inhabitants of the two double bedrooms with two full baths will enjoy their own private living space. The lower level offers perfect rooms for entertaining. Open the pocket doors between the theatre and billiard/bar room for Super Bowl parties or close them for intimate movie viewing. The 3,000 bottle walk-in wine cellar will sufficiently accommodate your collection. Have peace of mind with the secure room equipped with separate security lock system. This level also has an expansive multi purpose/game room, laundry, full bath, half bath, and plenty of storage rooms and closets. The grounds surrounding this home have a variety of memory making places. Whatever you're looking for, relaxation or activity. Take pleasure in the feeling of an outdoor shower after swimming laps in the pool and time in the hot tub, practice your yoga sunrise salutations from the covered porch, or simply read a book under a tree. Shoot some hoops, kick or throw a ball on the playing fields, sit around the fire pit singing and/or telling stories, or play king of the grill. Join the Greenwich Country Club and go across the street to participate in activities offered such as tennis, golf, platform tennis, swimming, bowling, and dining. Life is good.

17. 2019-08-13
    status Pending 3357-char remark

    Show marketing remark (3357 chars)

    Live the Good Life on Doubling Road. Conveniently located near central Greenwich, this stone and shingle style 7 bedrooms/8.3 baths home, designed by Austin Patterson Disston and built by Stone Harbour builders, is commandingly set on 2.93 park-like acres with views overlooking the Greenwich Country Club golf course and Long Island Sound on the horizon. The location is minutes to Greenwich Avenue, Private & Public Schools, Merritt Parkway, I95, and Metro-North Railroad. The estate includes the four level 10,190 sf main house with attached 2 car garage, 5 car detached temperature controlled garage with 2 car lifts already plumbed and wired for a 2nd floor apartment, a heated pool plus separate jacuzzi spa, and a pool gazebo with enclosed outdoor shower. The grand double height entrance hall is welcoming and is the introduction to the formal living room with fireplace, mahogany paneled library/office with fireplace, formal dining room, gourmet kitchen with walk-in pantry, family room with fireplace, attached screened gazebo, and exercise area/1st floor master suite. The spacious mud room is accessed by a second front entrance, the garage and back door, plus formal and informal powder rooms. Bring the light and beauty from the outside in with an abundance of French doors throughout. From the expansive covered cedar porch, blue stone patios, master bedroom and third floor balcony, enjoy the changing views of the professionally orchestrated landscaped grounds and the high views over the country club golf course artistically framed by privacy providing mature trees. The gracefully ascending staircase gives a panoramic view of the entrance hall and second floor hallway. The second floor includes the master bedroom suite with luxurious bathroom consisting of steam shower and jacuzzi tub, vanity area, walk-in closet/lounge, and private balcony. In addition, there are three light filled en suite double bedrooms and an impressive upstairs family room with double height ceiling. On the third floor is a very large common room with wet bar and balcony giving a bird's eye perspective. The inhabitants of the two double bedrooms with two full baths will enjoy their own private living space. The lower level offers perfect rooms for entertaining. Open the pocket doors between the theatre and billiard/bar room for Super Bowl parties or close them for intimate movie viewing. The 3,000 bottle walk-in wine cellar will sufficiently accommodate your collection. Have peace of mind with the secure room equipped with separate security lock system. This level also has an expansive multi purpose/game room, laundry, full bath, half bath, and plenty of storage rooms and closets. The grounds surrounding this home have a variety of memory making places. Whatever you're looking for, relaxation or activity. Take pleasure in the feeling of an outdoor shower after swimming laps in the pool and time in the hot tub, practice your yoga sunrise salutations from the covered porch, or simply read a book under a tree. Shoot some hoops, kick or throw a ball on the playing fields, sit around the fire pit singing and/or telling stories, or play king of the grill. Join the Greenwich Country Club and go across the street to participate in activities offered such as tennis, golf, platform tennis, swimming, bowling, and dining. Life is good.

18. 2019-06-24
    price $8,900,000 3357-char remark

    Show marketing remark (3357 chars)

    Live the Good Life on Doubling Road. Conveniently located near central Greenwich, this stone and shingle style 7 bedrooms/8.3 baths home, designed by Austin Patterson Disston and built by Stone Harbour builders, is commandingly set on 2.93 park-like acres with views overlooking the Greenwich Country Club golf course and Long Island Sound on the horizon. The location is minutes to Greenwich Avenue, Private & Public Schools, Merritt Parkway, I95, and Metro-North Railroad. The estate includes the four level 10,190 sf main house with attached 2 car garage, 5 car detached temperature controlled garage with 2 car lifts already plumbed and wired for a 2nd floor apartment, a heated pool plus separate jacuzzi spa, and a pool gazebo with enclosed outdoor shower. The grand double height entrance hall is welcoming and is the introduction to the formal living room with fireplace, mahogany paneled library/office with fireplace, formal dining room, gourmet kitchen with walk-in pantry, family room with fireplace, attached screened gazebo, and exercise area/1st floor master suite. The spacious mud room is accessed by a second front entrance, the garage and back door, plus formal and informal powder rooms. Bring the light and beauty from the outside in with an abundance of French doors throughout. From the expansive covered cedar porch, blue stone patios, master bedroom and third floor balcony, enjoy the changing views of the professionally orchestrated landscaped grounds and the high views over the country club golf course artistically framed by privacy providing mature trees. The gracefully ascending staircase gives a panoramic view of the entrance hall and second floor hallway. The second floor includes the master bedroom suite with luxurious bathroom consisting of steam shower and jacuzzi tub, vanity area, walk-in closet/lounge, and private balcony. In addition, there are three light filled en suite double bedrooms and an impressive upstairs family room with double height ceiling. On the third floor is a very large common room with wet bar and balcony giving a bird's eye perspective. The inhabitants of the two double bedrooms with two full baths will enjoy their own private living space. The lower level offers perfect rooms for entertaining. Open the pocket doors between the theatre and billiard/bar room for Super Bowl parties or close them for intimate movie viewing. The 3,000 bottle walk-in wine cellar will sufficiently accommodate your collection. Have peace of mind with the secure room equipped with separate security lock system. This level also has an expansive multi purpose/game room, laundry, full bath, half bath, and plenty of storage rooms and closets. The grounds surrounding this home have a variety of memory making places. Whatever you're looking for, relaxation or activity. Take pleasure in the feeling of an outdoor shower after swimming laps in the pool and time in the hot tub, practice your yoga sunrise salutations from the covered porch, or simply read a book under a tree. Shoot some hoops, kick or throw a ball on the playing fields, sit around the fire pit singing and/or telling stories, or play king of the grill. Join the Greenwich Country Club and go across the street to participate in activities offered such as tennis, golf, platform tennis, swimming, bowling, and dining. Life is good.

19. 2019-06-03
    listed $9,700,000 Active 3357-char remark

    Show marketing remark (3357 chars)

    Live the Good Life on Doubling Road. Conveniently located near central Greenwich, this stone and shingle style 7 bedrooms/8.3 baths home, designed by Austin Patterson Disston and built by Stone Harbour builders, is commandingly set on 2.93 park-like acres with views overlooking the Greenwich Country Club golf course and Long Island Sound on the horizon. The location is minutes to Greenwich Avenue, Private & Public Schools, Merritt Parkway, I95, and Metro-North Railroad. The estate includes the four level 10,190 sf main house with attached 2 car garage, 5 car detached temperature controlled garage with 2 car lifts already plumbed and wired for a 2nd floor apartment, a heated pool plus separate jacuzzi spa, and a pool gazebo with enclosed outdoor shower. The grand double height entrance hall is welcoming and is the introduction to the formal living room with fireplace, mahogany paneled library/office with fireplace, formal dining room, gourmet kitchen with walk-in pantry, family room with fireplace, attached screened gazebo, and exercise area/1st floor master suite. The spacious mud room is accessed by a second front entrance, the garage and back door, plus formal and informal powder rooms. Bring the light and beauty from the outside in with an abundance of French doors throughout. From the expansive covered cedar porch, blue stone patios, master bedroom and third floor balcony, enjoy the changing views of the professionally orchestrated landscaped grounds and the high views over the country club golf course artistically framed by privacy providing mature trees. The gracefully ascending staircase gives a panoramic view of the entrance hall and second floor hallway. The second floor includes the master bedroom suite with luxurious bathroom consisting of steam shower and jacuzzi tub, vanity area, walk-in closet/lounge, and private balcony. In addition, there are three light filled en suite double bedrooms and an impressive upstairs family room with double height ceiling. On the third floor is a very large common room with wet bar and balcony giving a bird's eye perspective. The inhabitants of the two double bedrooms with two full baths will enjoy their own private living space. The lower level offers perfect rooms for entertaining. Open the pocket doors between the theatre and billiard/bar room for Super Bowl parties or close them for intimate movie viewing. The 3,000 bottle walk-in wine cellar will sufficiently accommodate your collection. Have peace of mind with the secure room equipped with separate security lock system. This level also has an expansive multi purpose/game room, laundry, full bath, half bath, and plenty of storage rooms and closets. The grounds surrounding this home have a variety of memory making places. Whatever you're looking for, relaxation or activity. Take pleasure in the feeling of an outdoor shower after swimming laps in the pool and time in the hot tub, practice your yoga sunrise salutations from the covered porch, or simply read a book under a tree. Shoot some hoops, kick or throw a ball on the playing fields, sit around the fire pit singing and/or telling stories, or play king of the grill. Join the Greenwich Country Club and go across the street to participate in activities offered such as tennis, golf, platform tennis, swimming, bowling, and dining. Life is good.

20. 2019-05-25
    historical Expired
21. 2019-05-25
    historical
22. 2019-03-09
    price $9,700,000
23. 2019-03-08
    price $9,700,000
24. 2018-06-26
    listed $10,700,000 Active
25. 2018-05-24
    listed $10,700,000 Active
26. 2006-06-01
    soldstatus $5,000,000

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

Tax reassessment forecast CT · Partial reset (capped growth)

• Current annual tax: $47,986 · $3,999/mo
• Projected year-2 tax: $237,458 · $19,788/mo
• Expected delta: +$189,472/yr (+$15,789/mo · 394.8%)

ⓘ 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 2/10 Low
• 🌡 Heat 5/10 Major 7 d/yr ≥98°F today · 15 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 67% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 5 unhealthy d/yr today · 7 by 30 yrs out

Taxation est. · year 1

• Rental income: $71,664
• − Mortgage interest: −$1,117,510
• − Property taxes: −$47,986
• − Insurance: −$99,750
• − Repairs & maintenance: −$5,733
• − Management: −$5,733
• − Depreciation: −$580,364
• Taxable loss: −$1,785,412
• Est. tax savings @ 24.0%: +$428,499
• After-tax cash flow: $-918,062/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: Greenwich School District
• NCES district ID: 0901710
• Math proficiency: 64% ▼ -7.00%
• Reading proficiency: 73% ▼ -5.00%
• Median HH income: $129,257
• Composite: 65.67/100
• National rank: #461
• State rank: #12 of 153 in CT

Livability — Greenwich

• Score: 80/100
• State rank: #23
• US rank: #1655

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• County: Fairfield County · 765,532 people
• City population: 47,954
• Metro: Bridgeport-Stamford-Norwalk, CT
• Population (ZIP): 24,880
• Household income: $146,654
• Rent vs Own: 42.6% rent · 57.4% own
• Severe rent burden: 1088.0

Population outlook (Western Connecticut County) Hauer SSP2

• By 2040: 685,031

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Diverse neighborhood (Simpson 0.55)
• Race & ethnicity: White 64% Hispanic / Latino 18% Two or more races 10% Asian 6% Black 5%
• Hispanic origin (detail): Mexican 2% Puerto Rican 1% Dominican 1%
• Common ancestry: Romanian 3% Lithuanian 2% Scotch-Irish 2%
• Foreign-born: 24% · Canada, Jamaica, China
• Languages at home: 72% English-only · Spanish 12% Other Indo-European 5% Russian/Polish/Slavic 3%

Political lean MEDSL · Western Connecticut

• 2024 margin: D (+19.1) · D 58.8% · R 39.7% · Other 1.6%
• All cycles: 2024: D+19.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 6.89%
• Current HPI: 173.5938
• Rent YoY: ▲ 3.36%
• Metro: Bridgeport-Stamford-Norwalk, CT
• State GDP YoY: ▲ 1.06%
• F500 in state: 38

Industry mix (Fortune 500 HQ in CT)

Industry	F500 HQs	Revenue
▸Industrial Machinery	4	$38B
▸Insurance	3	$71B
▸Financial Services	2	$25B
▸Transportation / Logistics	2	$18B
▸Healthcare	1	$247B
▸Telecommunications	1	$55B

Price history

+299.0% since first listed

13 events — show timeline

• 2026-06-11 Price Changed $19,950,000 GMLS
• 2026-05-01 Listed $24,500,000 GMLS
• 2019-09-24 Sold (MLS) $8,347,000 GMLS
• 2019-08-13 Pending — GMLS
• 2019-06-24 Price Changed $8,900,000 GMLS
• 2019-06-03 Listed $9,700,000 GMLS
• 2019-05-25 Delisted — GMLS
• 2019-05-25 Listing Removed — Smart MLS
• 2019-03-09 Price Changed $9,700,000 Smart MLS
• 2019-03-08 Price Changed $9,700,000 GMLS
• 2018-06-26 Listed $10,700,000 Smart MLS
• 2018-05-24 Listed $10,700,000 GMLS
• 2006-06-01 Sold (Public Records) $5,000,000 Public Records

Property tax history

-3.2%/yr

Latest (2023): $47,986 · +1.5% YoY. Source: county tax records.