599 Durham Rd · Guilford Center, CT 06437

$539,000

4 bd · 1.5 ba · 1,718 sqft · SingleFamily public records · 61 Days on market

Built 1976 1.68 ac lot $314/sqft · at area comps Est $650k · 17% 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
• Cash flow +8.2/30.0
• Schools +6.3/10.0
• Livability +4.1/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +2.4/10.0
• DSCR +2.2/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

Charming cape offering a flexible floor plan in a highly desirable location just moments from the historic Guilford Green. This inviting property blends classic New England character with everyday versatility, featuring natural sun filled living spaces that can easily adapt to your lifestyle. Enjoy a warm and welcoming atmosphere, complemented by timeless details and comfortable flow throughout. The updated kitchen has new countertops and a new breakfast bar. There are beautiful hardwood floors throughout and 2 wood stoves to keep your utility bills low. The exterior of the home was recently painted. Enjoy a two-car attached garage with one new electric door opener. Conveniently located near shops, dining, and the shoreline, this home presents a wonderful opportunity to enjoy all that Guilford has to offer. Minutes to beaches, parks, town boat launch, restaurants and highways. Turn the key and move right in.

Key facts

• 1.68 acre lot
• 2 garage spots
• Built 1976

What this means for you Summary

Snapshot

• This is a 4-bed/1.5-bath single-family listed at $539k.

Deal economics

• At list price, monthly cash flow is $-508 ($-6k/yr) — negative.
• To cash-flow at today's rent, offer at most $449k (16.6% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $400k (25.8% below list).
• Recommended offer: $400k (25.8% below list) — sets the bar for 1% rule.
• Cap rate 5.2% vs local median 3.1% in Guilford Center — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.

Location & tenants

• Location reads 82/100 on livability (#10 in CT, #1,186 nationally) — a professional / high-income tenant draw. Strengths: crime A+, employment A+, health & safety A+; Watch: cost of living F.
• Guilford School District (suburban): math 64% / reading 75% proficiency, ranked #19 of 153 in CT (top 12%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 6% free/reduced lunch — higher-income household profile.
• Zoned schools: Guilford High School (math 60% / reading 84%, grade B+, #14 of 194 statewide, top 8%, 1,048 students, 11% FRL) — zoned schools at 11% FRL track the district average.
• Market conditions: 114 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 1,059 units permitted in South Central Connecticut Planning Region in 2024 (779 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $4k of loan paydown is wiped out by about $16k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 61 days — a 6% lower offer ($507k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 3y 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.

Risks & watch-outs

• Climate carrying-cost: major wind risk, 69% chance of damaging wind over 30y; extreme-heat days projected 7→17/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $400,000 (25.8% 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 61 days. Have you received any prior offers? Is the seller open to a 26% concession, seller financing, or rate buy-down credit?
3. Built in 1976 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. 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?
7. 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?
8. 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.
9. 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.
10. 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: 0.74% ✗
• Cap rate: 5.16%
• Cash-on-cash: -4.04%
• DSCR: 0.82
• GRM: 11.2

CMA / ARV

• ARV (median comp): $649,569
• List price: $539,000
• Delta: -17.02%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 6 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
94 Highwoods Dr	0.57mi	3/2.0 (-1)	1,708 (-1%)	20mo	$545,000	$319	49
905 Little Meadow Rd	0.63mi	3/2.0 (-1)	1,772 (+3%)	14mo	$550,100	$310	47
53 Driftwood Ln	0.52mi	3/2.5 (-1)	1,514 (-12%)	0mo	$640,000	$423	47
831 Nut Plains Rd	0.73mi	3/2.0 (-1)	1,760 (+2%)	16mo	$450,000	$256	42
332 Stepstone Hill Rd	0.74mi	4/2.0	1,845 (+7%)	16mo	$535,000	$290	38
226 Village Pond Rd	0.71mi	4/2.5	1,944 (+13%)	19mo	$625,000	$322	25

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

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

5-year hold

• IRR: -23.1%
• Equity multiple: 0.21×
• Total profit: $-119,659
• Equity at exit: $80,367

10-year hold

• IRR: -17.7%
• Equity multiple: 0.03×
• Total profit: $-145,742
• Equity at exit: $46,603

Cash invested: $150,920 (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 06437

• Active inventory: 114
• Price-to-rent: 11.2×

Monthly cashflow live

• Estimated rent: $4,000 medium
• Mortgage (P&I): −$2,827
• Tax from tax record: −$617 /mo · $7,400/yr
• Insurance: −$225
• HOA: −$0
• Vacancy / Maint / Mgmt: −$840
• Net cashflow: $-508

Break-even live

Break-even rent $4,643

Max offer price $449,291

Occupancy floor —

Sensitivity live

Price	-10% $-203	-5% $-355	+0% $-508	+5% $-660	+10% $-813
Rent	-10% $-824	-5% $-666	+0% $-508	+5% $-350	+10% $-192
Rate	-1.0pp $-236	-0.5pp $-371	base $-508	+0.5pp $-647	+1.0pp $-790

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: $134,750
• Closing costs: $16,170
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
831 Nut Plains Rd Guilford, CT	3.0	2.0	1760	$4,000	$2.27	16d	1	0.74mi

Listing history 24 events

1. 2026-06-15
   status $539,000 Under Contract 61 DOM
2. 2026-06-15
   days on market $539,000 Under Contract - Continue to Show 61 DOM
3. 2026-06-14
   days on market $539,000 Under Contract - Continue to Show 59 DOM
4. 2026-06-13
   days on market $539,000 Under Contract - Continue to Show 58 DOM
5. 2026-06-10
   days on market $539,000 Under Contract - Continue to Show 56 DOM
6. 2026-06-09
   days on market $539,000 Under Contract - Continue to Show 55 DOM
7. 2026-06-08
   days on market $539,000 Under Contract - Continue to Show 54 DOM
8. 2026-06-07
   days on market $539,000 Under Contract - Continue to Show 53 DOM
9. 2026-06-03
   days on market $539,000 Under Contract - Continue to Show 49 DOM
10. 2026-06-03
    days on market $539,000 Under Contract - Continue to Show 48 DOM
11. 2026-06-01
    days on market $539,000 Under Contract - Continue to Show 47 DOM
12. 2026-05-31
    days on market $539,000 Under Contract - Continue to Show 46 DOM
13. 2026-05-13
    historical Under Contract - Continue to Show 921-char remark

    Show marketing remark (921 chars)

    Charming cape offering a flexible floor plan in a highly desirable location just moments from the historic Guilford Green. This inviting property blends classic New England character with everyday versatility, featuring natural sun filled living spaces that can easily adapt to your lifestyle. Enjoy a warm and welcoming atmosphere, complemented by timeless details and comfortable flow throughout. The updated kitchen has new countertops and a new breakfast bar. There are beautiful hardwood floors throughout and 2 wood stoves to keep your utility bills low. The exterior of the home was recently painted. Enjoy a two-car attached garage with one new electric door opener. Conveniently located near shops, dining, and the shoreline, this home presents a wonderful opportunity to enjoy all that Guilford has to offer. Minutes to beaches, parks, town boat launch, restaurants and highways. Turn the key and move right in.

14. 2026-04-29
    price $539,000 921-char remark

    Show marketing remark (921 chars)

    Charming cape offering a flexible floor plan in a highly desirable location just moments from the historic Guilford Green. This inviting property blends classic New England character with everyday versatility, featuring natural sun filled living spaces that can easily adapt to your lifestyle. Enjoy a warm and welcoming atmosphere, complemented by timeless details and comfortable flow throughout. The updated kitchen has new countertops and a new breakfast bar. There are beautiful hardwood floors throughout and 2 wood stoves to keep your utility bills low. The exterior of the home was recently painted. Enjoy a two-car attached garage with one new electric door opener. Conveniently located near shops, dining, and the shoreline, this home presents a wonderful opportunity to enjoy all that Guilford has to offer. Minutes to beaches, parks, town boat launch, restaurants and highways. Turn the key and move right in.

15. 2026-04-16
    listed $549,000 Active 921-char remark

    Show marketing remark (921 chars)

    Charming cape offering a flexible floor plan in a highly desirable location just moments from the historic Guilford Green. This inviting property blends classic New England character with everyday versatility, featuring natural sun filled living spaces that can easily adapt to your lifestyle. Enjoy a warm and welcoming atmosphere, complemented by timeless details and comfortable flow throughout. The updated kitchen has new countertops and a new breakfast bar. There are beautiful hardwood floors throughout and 2 wood stoves to keep your utility bills low. The exterior of the home was recently painted. Enjoy a two-car attached garage with one new electric door opener. Conveniently located near shops, dining, and the shoreline, this home presents a wonderful opportunity to enjoy all that Guilford has to offer. Minutes to beaches, parks, town boat launch, restaurants and highways. Turn the key and move right in.

16. 2026-04-13
    historical $549,000 921-char remark

    Show marketing remark (921 chars)

    Charming cape offering a flexible floor plan in a highly desirable location just moments from the historic Guilford Green. This inviting property blends classic New England character with everyday versatility, featuring natural sun filled living spaces that can easily adapt to your lifestyle. Enjoy a warm and welcoming atmosphere, complemented by timeless details and comfortable flow throughout. The updated kitchen has new countertops and a new breakfast bar. There are beautiful hardwood floors throughout and 2 wood stoves to keep your utility bills low. The exterior of the home was recently painted. Enjoy a two-car attached garage with one new electric door opener. Conveniently located near shops, dining, and the shoreline, this home presents a wonderful opportunity to enjoy all that Guilford has to offer. Minutes to beaches, parks, town boat launch, restaurants and highways. Turn the key and move right in.

17. 2024-06-18
    soldstatus $489,900 Closed 1072-char remark

    Show marketing remark (1072 chars)

    Located only 4 minutes to the Guilford Town Green, shopping, and highway this loved home offers convenience and privacy. Set well back from the road, this Colonial has 3 bedrooms on the second floor with a walk-in closet and extra closet in the spacious primary BR. An additional BR in the lower level serves well as a guest room, office, hobby room, etc. The inviting family room on the first floor with wood burning stove has a private entrance and walks out to an expansive back deck. There are Hardwood floors on the first and second floors and an eat in kitchen that opens to the family room and dining room. The front to back living room offers lots of flexibility and is accented by yet another wood burning stove for efficient and inexpensive heating ( owners spent under $200 for oil for 2023 winter ). Lovely gardens abound the property and highlight the brick walkway to both entrances. An outside shed offers additional storage and there is parking for 10 cars. Freshly painted inside and new garage doors. Make your appointment today to see this lovely home.

18. 2024-05-29
    status Under Contract 1072-char remark

    Show marketing remark (1072 chars)

    Located only 4 minutes to the Guilford Town Green, shopping, and highway this loved home offers convenience and privacy. Set well back from the road, this Colonial has 3 bedrooms on the second floor with a walk-in closet and extra closet in the spacious primary BR. An additional BR in the lower level serves well as a guest room, office, hobby room, etc. The inviting family room on the first floor with wood burning stove has a private entrance and walks out to an expansive back deck. There are Hardwood floors on the first and second floors and an eat in kitchen that opens to the family room and dining room. The front to back living room offers lots of flexibility and is accented by yet another wood burning stove for efficient and inexpensive heating ( owners spent under $200 for oil for 2023 winter ). Lovely gardens abound the property and highlight the brick walkway to both entrances. An outside shed offers additional storage and there is parking for 10 cars. Freshly painted inside and new garage doors. Make your appointment today to see this lovely home.

19. 2024-05-09
    historical Under Contract - Continue to Show 1072-char remark

    Show marketing remark (1072 chars)

    Located only 4 minutes to the Guilford Town Green, shopping, and highway this loved home offers convenience and privacy. Set well back from the road, this Colonial has 3 bedrooms on the second floor with a walk-in closet and extra closet in the spacious primary BR. An additional BR in the lower level serves well as a guest room, office, hobby room, etc. The inviting family room on the first floor with wood burning stove has a private entrance and walks out to an expansive back deck. There are Hardwood floors on the first and second floors and an eat in kitchen that opens to the family room and dining room. The front to back living room offers lots of flexibility and is accented by yet another wood burning stove for efficient and inexpensive heating ( owners spent under $200 for oil for 2023 winter ). Lovely gardens abound the property and highlight the brick walkway to both entrances. An outside shed offers additional storage and there is parking for 10 cars. Freshly painted inside and new garage doors. Make your appointment today to see this lovely home.

20. 2024-05-04
    listed $489,900 Active 1072-char remark

    Show marketing remark (1072 chars)

    Located only 4 minutes to the Guilford Town Green, shopping, and highway this loved home offers convenience and privacy. Set well back from the road, this Colonial has 3 bedrooms on the second floor with a walk-in closet and extra closet in the spacious primary BR. An additional BR in the lower level serves well as a guest room, office, hobby room, etc. The inviting family room on the first floor with wood burning stove has a private entrance and walks out to an expansive back deck. There are Hardwood floors on the first and second floors and an eat in kitchen that opens to the family room and dining room. The front to back living room offers lots of flexibility and is accented by yet another wood burning stove for efficient and inexpensive heating ( owners spent under $200 for oil for 2023 winter ). Lovely gardens abound the property and highlight the brick walkway to both entrances. An outside shed offers additional storage and there is parking for 10 cars. Freshly painted inside and new garage doors. Make your appointment today to see this lovely home.

21. 2024-04-24
    historical $489,900 1072-char remark

    Show marketing remark (1072 chars)

    Located only 4 minutes to the Guilford Town Green, shopping, and highway this loved home offers convenience and privacy. Set well back from the road, this Colonial has 3 bedrooms on the second floor with a walk-in closet and extra closet in the spacious primary BR. An additional BR in the lower level serves well as a guest room, office, hobby room, etc. The inviting family room on the first floor with wood burning stove has a private entrance and walks out to an expansive back deck. There are Hardwood floors on the first and second floors and an eat in kitchen that opens to the family room and dining room. The front to back living room offers lots of flexibility and is accented by yet another wood burning stove for efficient and inexpensive heating ( owners spent under $200 for oil for 2023 winter ). Lovely gardens abound the property and highlight the brick walkway to both entrances. An outside shed offers additional storage and there is parking for 10 cars. Freshly painted inside and new garage doors. Make your appointment today to see this lovely home.

22. 2023-12-02
    historical
23. 2023-08-19
    listed $499,000 Active
24. 2023-08-10
    historical

ⓘ 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: $7,400 · $617/mo
• Projected year-2 tax: $9,467 · $789/mo
• Expected delta: +$2,067/yr (+$172/mo · 27.9%)

ⓘ 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 3/10 Moderate
• 🌡 Heat 6/10 Major 7 d/yr ≥94°F today · 17 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 69% 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: $48,000
• − Mortgage interest: −$30,192
• − Property taxes: −$7,400
• − Insurance: −$2,695
• − Repairs & maintenance: −$3,840
• − Management: −$3,840
• − Depreciation: −$15,680
• Taxable loss: −$15,647
• Est. tax savings @ 24.0%: +$3,755
• After-tax cash flow: $-2,339/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: Guilford School District
• NCES district ID: 0901800
• Math proficiency: 64% ▼ -12.00%
• Reading proficiency: 75% ▼ -7.00%
• Median HH income: $97,539
• Composite: 63.46/100
• National rank: #614
• State rank: #19 of 153 in CT

Livability — Guilford Center

• Score: 82/100
• State rank: #10
• US rank: #1186

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Population (ZIP): 22,037

Population outlook (South Central Connecticut County) Hauer SSP2

• By 2040: 608,362

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (87%)
• Race & ethnicity: White 87% Two or more races 6% Hispanic / Latino 4% Asian 3% Black 2%
• Common ancestry: Romanian 7% Lithuanian 3% Slovak 2%
• Foreign-born: 8% · Canada, China
• Languages at home: 90% English-only · Spanish 3% Other Indo-European 2% German/W. Germanic 1%

Political lean MEDSL · South Central Connecticut

• 2024 margin: Strong D (+20.1) · D 59.0% · R 38.9% · Other 2.1%
• All cycles: 2024: D+20.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -267.02%
• Current HPI: 179.6376
• Rent YoY: —
• Metro: —
• 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

+8.0% since first listed

12 events — show timeline

• 2026-05-13 Contingent — Smart MLS
• 2026-04-29 Price Changed $539,000 Smart MLS
• 2026-04-16 Listed $549,000 Smart MLS
• 2026-04-13 Coming Soon $549,000 Smart MLS
• 2024-06-18 Sold (MLS) $489,900 Smart MLS
• 2024-05-29 Pending — Smart MLS
• 2024-05-09 Contingent — Smart MLS
• 2024-05-04 Listed $489,900 Smart MLS
• 2024-04-24 Coming Soon $489,900 Smart MLS
• 2023-12-02 Listing Removed — Smart MLS
• 2023-08-19 Listed $499,000 Smart MLS
• 2023-08-10 Coming Soon — Smart MLS

Property tax history

+1.5%/yr

Latest (2023): $7,400 · -3.0% YoY. Source: county tax records.