The Oliver Plan · Oconomowoc, WI 53066

$413,600

3 bd · 2.5 ba · 1,602 sqft · SingleFamily · 574 Days on market

---

Why this score? — see what drove the F 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 +7.5/15.0
• Schools +4.8/10.0
• Livability +4.5/5.0
• Cash flow +4.0/30.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +0.2/10.0
• DSCR +0.0/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

The Oliver is a 1602 sqft townhome featuring three bedrooms, two-and-a-half baths, and an attached two-car garage. Step through the welcoming covered porch into an open foyer and then into the great room. The adjacent dining area flows seamlessly into the open kitchen, which includes an island, a pantry, and generous cabinet space with plenty of storage for all your culinary needs. Toward the back of the home, you'll find a convenient powder room, a rear foyer with a coat closet, and an optional drop zone, as well as access to the two-car garage. Upstairs, the primary bedroom awaits, featuring a spacious walk-in closet and an ensuite bathroom with an option to upgrade to the luxury bath. Two additional bedrooms, both with walk-in closets, share a full hall bath. A laundry closet for the washer and dryer rounds out the second floor and makes household chores just a little easier

Key facts

• 2 parking spots
• Listed 573 days

🏗️ New construction. The $413,600 list price is a builder figure, so every metric below is computed on the value from comparable previous sales — $483,250.

What this means for you Summary

Snapshot

• This is a 3-bed/2.5-bath single-family listed at $414k.

Deal economics

• At list price, monthly cash flow is $-1k ($-16k/yr) — negative.
• To cash-flow at today's rent, offer at most $287k (30.6% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $251k (39.3% below list).
• Recommended offer: $251k (39.3% below list) — sets the bar for 1% rule.
• Cap rate 2.9% vs local median 1.3% in Oconomowoc — 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 89/100 on livability (#12 in WI, #159 nationally) — a professional / high-income tenant draw. Strengths: crime A+, employment A+, housing A+; Watch: commute F.
• Oconomowoc Area School District (suburban): math 56% / reading 49% proficiency, ranked #39 of 342 in WI (top 11%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 14% free/reduced lunch — higher-income household profile.
• Market conditions: Rents flat; 303 active listings in the ZIP; 6 comparable units currently listed for rent nearby; rentals leasing fast (median 3d on market — plan ~1-2 weeks tenant-placement turnaround); high-income renter base; 1,885 units permitted in Waukesha County in 2024 (696 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $3k of loan paydown is wiped out by about $14k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 574 days — a 12% lower offer ($364k) is reasonable based on typical stale-listing flexibility.

Recommended offer $250,957 (39.3% 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 574 days. Have you received any prior offers? Is the seller open to a 39% 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: 0.52% ✗
• Cap rate: 2.92%
• Cash-on-cash: -12.04%
• DSCR: 0.46
• GRM: 16.0

CMA / ARV

• ARV (median comp): $483,250
• List price: $413,600
• Delta: -14.41%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 9 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
1467 Olde Highlander Dr	0.25mi	3/2.5	1,562 (-2%)	2mo	$429,221	$275	83
1461 Olde Highlander Dr	0.27mi	3/2.5	1,675 (+5%)	2mo	$419,545	$250	78
1477 Olde Highlander Dr	0.23mi	3/2.5	1,675 (+5%)	5mo	$439,421	$262	77
1470 Olde Highlander Dr	0.23mi	2/2.5 (-1)	1,490 (-7%)	2mo	$406,496	$273	71
1499 Olde Highlander Dr	0.28mi	3/2.5	1,675 (+5%)	15mo	$409,000	$244	67
1485 Olde Highlander Dr	0.21mi	2/2.5 (-1)	1,490 (-7%)	15mo	$400,000	$268	61
1326 Olde Highlander Dr	0.40mi	3/2.0	1,722 (+8%)	16mo	$528,800	$307	53
3202 N Silver Cedar Rd	0.35mi	3/2.5	1,837 (+15%)	8mo	$550,000	$299	52
1443 Olde Highlander Dr	0.40mi	3/2.0	1,763 (+10%)	13mo	$555,740	$315	52

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 · 0.05% rent growth · sell at horizon

5-year hold

• IRR: -41.7%
• Equity multiple: -0.27×
• Total profit: $-171,937
• Equity at exit: $72,054

10-year hold

• IRR: -91.0%
• Equity multiple: -1.13×
• Total profit: $-288,852
• Equity at exit: $41,783

Cash invested: $135,310 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 73 Landlord-Friendly
• State Wisconsin: 73 Landlord-Friendly · R+2
• County: — inherits STATE
• City: — inherits STATE

5-day notice; preempted; Madison / Milwaukee have some local enforcement.

Methodology + full state rankings →

ZIP-level market 53066

• Rents YoY: 0.1%
• Active inventory: 303
• Price-to-rent: 13.7×

Monthly cashflow live

• Estimated rent: $2,510 high
• Mortgage (P&I): −$2,534
• Tax est. 1.5%: −$604 /mo · $7,249/yr
• Insurance: −$201
• HOA: −$0
• Vacancy / Maint / Mgmt: −$527
• Net cashflow: $-1,357

Break-even live

Break-even rent $4,227

Max offer price $286,880

Occupancy floor —

Sensitivity live

Price	-10% $-1,023	-5% $-1,190	+0% $-1,357	+5% $-1,524	+10% $-1,691
Rent	-10% $-1,555	-5% $-1,456	+0% $-1,357	+5% $-1,258	+10% $-1,159
Rate	-1.0pp $-1,114	-0.5pp $-1,234	base $-1,357	+0.5pp $-1,482	+1.0pp $-1,610

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: $120,812
• Closing costs: $14,497
• Reserves months: —
• Total cash needed: —

Rent comps 6 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
1455 Pabst Rd Oconomowoc, WI	2.0–3.0	2.0	1450	$2,994	$2.06	2d	9	0.20mi
1350 Kari Ct Oconomowoc, WI	3.0	1.0–2.0	954	$2,670	$2.80	2d	9	0.47mi
1550 Valley Rd Oconomowoc, WI	1.0–3.0	1.0–2.5	1145	$3,292	$2.87	2d	12	0.88mi
281 Oconomowoc Pkwy Oconomowoc, WI	2.0	2.0	1100	$1,850	$1.68	5d	1	1.05mi
530 Bolson Dr Oconomowoc, WI	2.0	1.0	1050	$1,195	$1.14	17d	1	1.37mi
420 Bolson Dr Oconomowoc, WI	2.0	1.5	1300	$1,600	$1.23	2d	1	1.40mi

Listing history 6 events

1. 2026-03-25
   price $413,600 890-char remark

   Show marketing remark (890 chars)

   The Oliver is a 1602 sqft townhome featuring three bedrooms, two-and-a-half baths, and an attached two-car garage. Step through the welcoming covered porch into an open foyer and then into the great room. The adjacent dining area flows seamlessly into the open kitchen, which includes an island, a pantry, and generous cabinet space with plenty of storage for all your culinary needs. Toward the back of the home, you'll find a convenient powder room, a rear foyer with a coat closet, and an optional drop zone, as well as access to the two-car garage. Upstairs, the primary bedroom awaits, featuring a spacious walk-in closet and an ensuite bathroom with an option to upgrade to the luxury bath. Two additional bedrooms, both with walk-in closets, share a full hall bath. A laundry closet for the washer and dryer rounds out the second floor and makes household chores just a little easier

2. 2026-01-20
   price $408,400 890-char remark

   Show marketing remark (890 chars)

   The Oliver is a 1602 sqft townhome featuring three bedrooms, two-and-a-half baths, and an attached two-car garage. Step through the welcoming covered porch into an open foyer and then into the great room. The adjacent dining area flows seamlessly into the open kitchen, which includes an island, a pantry, and generous cabinet space with plenty of storage for all your culinary needs. Toward the back of the home, you'll find a convenient powder room, a rear foyer with a coat closet, and an optional drop zone, as well as access to the two-car garage. Upstairs, the primary bedroom awaits, featuring a spacious walk-in closet and an ensuite bathroom with an option to upgrade to the luxury bath. Two additional bedrooms, both with walk-in closets, share a full hall bath. A laundry closet for the washer and dryer rounds out the second floor and makes household chores just a little easier

3. 2025-06-12
   price $401,400 890-char remark

   Show marketing remark (890 chars)

   The Oliver is a 1602 sqft townhome featuring three bedrooms, two-and-a-half baths, and an attached two-car garage. Step through the welcoming covered porch into an open foyer and then into the great room. The adjacent dining area flows seamlessly into the open kitchen, which includes an island, a pantry, and generous cabinet space with plenty of storage for all your culinary needs. Toward the back of the home, you'll find a convenient powder room, a rear foyer with a coat closet, and an optional drop zone, as well as access to the two-car garage. Upstairs, the primary bedroom awaits, featuring a spacious walk-in closet and an ensuite bathroom with an option to upgrade to the luxury bath. Two additional bedrooms, both with walk-in closets, share a full hall bath. A laundry closet for the washer and dryer rounds out the second floor and makes household chores just a little easier

4. 2025-03-15
   price $395,800 890-char remark

   Show marketing remark (890 chars)

   The Oliver is a 1602 sqft townhome featuring three bedrooms, two-and-a-half baths, and an attached two-car garage. Step through the welcoming covered porch into an open foyer and then into the great room. The adjacent dining area flows seamlessly into the open kitchen, which includes an island, a pantry, and generous cabinet space with plenty of storage for all your culinary needs. Toward the back of the home, you'll find a convenient powder room, a rear foyer with a coat closet, and an optional drop zone, as well as access to the two-car garage. Upstairs, the primary bedroom awaits, featuring a spacious walk-in closet and an ensuite bathroom with an option to upgrade to the luxury bath. Two additional bedrooms, both with walk-in closets, share a full hall bath. A laundry closet for the washer and dryer rounds out the second floor and makes household chores just a little easier

5. 2024-12-20
   price $390,800 890-char remark

   Show marketing remark (890 chars)

   The Oliver is a 1602 sqft townhome featuring three bedrooms, two-and-a-half baths, and an attached two-car garage. Step through the welcoming covered porch into an open foyer and then into the great room. The adjacent dining area flows seamlessly into the open kitchen, which includes an island, a pantry, and generous cabinet space with plenty of storage for all your culinary needs. Toward the back of the home, you'll find a convenient powder room, a rear foyer with a coat closet, and an optional drop zone, as well as access to the two-car garage. Upstairs, the primary bedroom awaits, featuring a spacious walk-in closet and an ensuite bathroom with an option to upgrade to the luxury bath. Two additional bedrooms, both with walk-in closets, share a full hall bath. A laundry closet for the washer and dryer rounds out the second floor and makes household chores just a little easier

6. 2024-10-30
   listed $388,900 Active 890-char remark

   Show marketing remark (890 chars)

   The Oliver is a 1602 sqft townhome featuring three bedrooms, two-and-a-half baths, and an attached two-car garage. Step through the welcoming covered porch into an open foyer and then into the great room. The adjacent dining area flows seamlessly into the open kitchen, which includes an island, a pantry, and generous cabinet space with plenty of storage for all your culinary needs. Toward the back of the home, you'll find a convenient powder room, a rear foyer with a coat closet, and an optional drop zone, as well as access to the two-car garage. Upstairs, the primary bedroom awaits, featuring a spacious walk-in closet and an ensuite bathroom with an option to upgrade to the luxury bath. Two additional bedrooms, both with walk-in closets, share a full hall bath. A laundry closet for the washer and dryer rounds out the second floor and makes household chores just a little easier

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

Taxation est. · year 1

• Rental income: $30,115
• − Mortgage interest: −$27,069
• − Property taxes: −$7,249
• − Insurance: −$2,416
• − Repairs & maintenance: −$2,409
• − Management: −$2,409
• − Depreciation: −$14,058
• Taxable loss: −$25,496
• Est. tax savings @ 24.0%: +$6,119
• After-tax cash flow: $-10,166/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: Oconomowoc Area School District
• NCES district ID: 5510890
• Math proficiency: 56% ▲ 1.00%
• Reading proficiency: 49% ▲ 1.00%
• Median HH income: $77,534
• Composite: 47.53/100
• National rank: #2273
• State rank: #39 of 342 in WI

Livability — Oconomowoc

• Score: 89/100
• State rank: #12
• US rank: #159

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Oconomowoc, WI
• County: Waukesha County · 231,951 people
• City population: 37,558
• Metro: Milwaukee-Waukesha, WI
• Population (ZIP): 37,558
• Household income: $113,114
• Rent vs Own: 21.8% rent · 78.2% own
• Severe rent burden: 869.0

Population outlook (Waukesha County) Hauer SSP2

• Today (2025): 412,798 people
• By 2030: 418,092 · +1.3%
• By 2040: 420,872 · +2.0%
• By 2050: 413,862 · +0.3%
• By 2075: 402,782 · -2.4%
• By 2100: 365,796 · -11.4%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (93%)
• Race & ethnicity: White 93% Two or more races 3% Hispanic / Latino 2%
• Common ancestry: Romanian 11% Portuguese 5% Lithuanian 3%
• Foreign-born: 2% · Canada
• Languages at home: 97% English-only · German/W. Germanic 2% Spanish 1%

Political lean MEDSL · Waukesha

• 2024 margin: R (+19.8) · D 39.5% · R 59.2% · Other 1.3%
• 2008→2024 swing: +5.9pp toward D · 2008: -25.7pp · 2024: -19.8pp
• All cycles: 2024: R+19.8 2020: R+20.8 2016: R+27.1 2012: R+34.8 2008: R+25.7

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -221.52%
• Current HPI: 274.4169
• Rent YoY: ▬ 0.05%
• Metro: Milwaukee-Waukesha, WI
• State GDP YoY: ▲ 2.10%
• F500 in state: 20

Industry mix (Fortune 500 HQ in WI)

Industry	F500 HQs	Revenue
▸Industrial Machinery	4	$23B
▸Industrial Technology	2	$36B
▸Insurance	1	$36B
▸Professional Services	1	$19B
▸Utilities	1	$9B
▸Consumer Goods	1	$3B

Price history

+6.4% since first listed

6 events — show timeline

• 2026-03-25 Price Changed $413,600 Zillow
• 2026-01-20 Price Changed $408,400 Zillow
• 2025-06-12 Price Changed $401,400 Zillow
• 2025-03-15 Price Changed $395,800 Zillow
• 2024-12-20 Price Changed $390,800 Zillow
• 2024-10-30 Listed $388,900 Zillow