SFoverasking

Recently sold › West of Twin Peaks › Maywood Dr

299 Maywood Dr

San Francisco, CA 94127

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299 Maywood Dr

Sold 2026-06-29

$4,000,000

Sale price

  • 3 beds
  • 3 baths
  • 4,250 sqft
  • Single-family home

5,772 sqft lot

Updated 2026-10-26. Prices and availability may have changed.

Sale versus asking

We don’t have this sale’s asking-price history yet.

Today’s estimate uses 4,250 sqft and the home’s latest facts. It does not estimate the home’s value at a past sale date.

0.2 mi0.3 mi$8.29M$5.13M$3.63M$3.38M$4.89M$3.44M$3.42M$4.32M$3.41M$3.40M$2.54M$3.32M$3.51M$3.69M$2.85M$2.74M$2.63M$3.03M$2.68M$3.09M$2.91M$2.99M$4.02M$3.06M299 Maywood DrBlock 3045, Lot 00900.25 miN275 Maywood Dr: sold for $4,225,000 on 2026-09-25, under 0.05 mi away222 Maywood Dr: sold for $4,410,000 on 2026-05-29, 0.10 mi away160 San Buenaventura Way: sold for $8,000,000 on 2026-06-22, 0.27 mi away199 Brentwood Ave: sold for $4,800,000 on 2026-02-26, 0.20 mi away1475 Monterey Blvd: sold for $3,500,000 on 2026-03-16, 0.19 mi away55 Upland Dr: sold for $2,757,809 on 2026-03-20, 0.21 mi away1380 Monterey Blvd: sold for $3,300,000 on 2026-04-23, 0.11 mi away2 Rosewood Dr: sold for $4,600,000 on 2026-07-23, 0.21 mi away850 Darien Way: sold for $2,950,000 on 2025-11-26, 0.18 mi away1185 Monterey Blvd: sold for $3,300,018 on 2026-06-17, 0.12 mi away154 Maywood Dr: sold for $3,706,000 on 2025-11-20, 0.16 mi away155 Upland Dr: sold for $2,825,000 on 2026-04-16, 0.22 mi away1100 Monterey Blvd: sold for $3,300,000 on 2026-05-18, 0.08 mi away115 Upland Dr: sold for $3,400,000 on 2026-09-10, 0.22 mi away95 Pinehurst Way: sold for $2,450,000 on 2026-03-19, 0.31 mi away411 Hazelwood Ave: sold for $2,700,000 on 2026-08-14, 0.30 mi away611 Miramar Ave: sold for $2,850,000 on 2026-01-06, 0.30 mi away96 Brentwood Ave: sold for $3,299,892 on 2026-07-22, 0.34 mi away477 Hazelwood Ave: sold for $3,488,888 on 2026-08-21, 0.24 mi away840 Faxon Ave: sold for $2,780,000 on 2026-04-13, 0.23 mi away126 Aptos Ave: sold for $2,651,000 on 2026-05-11, 0.32 mi away72 Cresta Vista Dr: sold for $2,535,000 on 2026-03-31, 0.31 mi away75 San Jacinto Way: sold for $2,300,000 on 2026-02-27, 0.12 mi away130 Maywood Dr: sold for $2,920,000 on 2026-06-22, 0.20 mi away23 Cresta Vista Dr: sold for $2,580,000 on 2026-03-23, 0.30 mi away333 San Benito Way: sold for $3,015,000 on 2026-04-16, 0.31 mi away630 Darien Way: sold for $2,550,000 on 2026-04-22, 0.19 mi away760 Darien Way: sold for $2,500,000 on 2025-11-20, 0.18 mi away315 San Benito Way: sold for $2,800,000 on 2026-02-20, 0.30 mi away345 Santa Clara Ave: sold for $3,450,000 on 2025-11-13, 0.30 mi away185 Upland Dr: sold for $2,630,000 on 2025-11-06, 0.22 mi away0.35 mi0.2 mi$4.56M$5.13M$4.89M$3.44M$4.32M$3.41M$3.40M$2.54M$3.51M$2.85M$2.74M$2.63M$2.68M$3.09M$2.99M$4.02M299 Maywood DrBlock 3045, Lot 00900.25 miN275 Maywood Dr: sold for $4,225,000 on 2026-09-25, under 0.05 mi away222 Maywood Dr: sold for $4,410,000 on 2026-05-29, 0.10 mi away160 San Buenaventura Way: sold for $8,000,000 on 2026-06-22, 0.27 mi away199 Brentwood Ave: sold for $4,800,000 on 2026-02-26, 0.20 mi away1475 Monterey Blvd: sold for $3,500,000 on 2026-03-16, 0.19 mi away55 Upland Dr: sold for $2,757,809 on 2026-03-20, 0.21 mi away1380 Monterey Blvd: sold for $3,300,000 on 2026-04-23, 0.11 mi away2 Rosewood Dr: sold for $4,600,000 on 2026-07-23, 0.21 mi away850 Darien Way: sold for $2,950,000 on 2025-11-26, 0.18 mi away1185 Monterey Blvd: sold for $3,300,018 on 2026-06-17, 0.12 mi away154 Maywood Dr: sold for $3,706,000 on 2025-11-20, 0.16 mi away155 Upland Dr: sold for $2,825,000 on 2026-04-16, 0.22 mi away1100 Monterey Blvd: sold for $3,300,000 on 2026-05-18, 0.08 mi away115 Upland Dr: sold for $3,400,000 on 2026-09-10, 0.22 mi away95 Pinehurst Way: sold for $2,450,000 on 2026-03-19, 0.31 mi away411 Hazelwood Ave: sold for $2,700,000 on 2026-08-14, 0.30 mi away611 Miramar Ave: sold for $2,850,000 on 2026-01-06, 0.30 mi away96 Brentwood Ave: sold for $3,299,892 on 2026-07-22, 0.34 mi away477 Hazelwood Ave: sold for $3,488,888 on 2026-08-21, 0.24 mi away840 Faxon Ave: sold for $2,780,000 on 2026-04-13, 0.23 mi away126 Aptos Ave: sold for $2,651,000 on 2026-05-11, 0.32 mi away72 Cresta Vista Dr: sold for $2,535,000 on 2026-03-31, 0.31 mi away75 San Jacinto Way: sold for $2,300,000 on 2026-02-27, 0.12 mi away130 Maywood Dr: sold for $2,920,000 on 2026-06-22, 0.20 mi away23 Cresta Vista Dr: sold for $2,580,000 on 2026-03-23, 0.30 mi away333 San Benito Way: sold for $3,015,000 on 2026-04-16, 0.31 mi away630 Darien Way: sold for $2,550,000 on 2026-04-22, 0.19 mi away760 Darien Way: sold for $2,500,000 on 2025-11-20, 0.18 mi away315 San Benito Way: sold for $2,800,000 on 2026-02-20, 0.30 mi away345 Santa Clara Ave: sold for $3,450,000 on 2025-11-13, 0.30 mi away185 Upland Dr: sold for $2,630,000 on 2025-11-06, 0.22 mi away0.35 mi

32 sales inside 0.35 mi since May 2025. The estimate uses the 31 closest. Click a sale on the map, or untick it below, to leave it out.

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Estimated sale price today

Medium confidence

$4,520,000

$3,254,000estimated range$5,559,000

From 31 comps at a weighted median of $1,063 per sqft.

Block
3045
Lot
009
Sales
Nov 2025 to Sep 2026
Prices adjusted to
2026-11-01
Within
0.35 mi
Sold since
May 2025

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Sale prices versus asking

Similarity-weighted median: 16.7% above final asking.

Middle half: 6.5% above asking to 20.7% above asking.

28 of 31 selected comps have a verified final asking price.

Comparisons use the final advertised asking price from the same sale, before pending or closing.

Comparable sales (31)

Every sale inside the circle starts ticked. Untick one here, or click it on the map, to leave it out. Closer, more similar sales weigh more.

AddressSoldPriceFinal askingSale vs. askingAdj. today$/sqftSizeDist.WhyMatch
275 Maywood Dr2026-09-25$4.22M$3,500,000$725,000 above asking (20.7%)$4.22M$1,0634bd 4ba 3,973sf<0.05 minearby on same street, similar size, recent
222 Maywood Dr2026-05-29$4.41M$3,895,000$515,000 above asking (13.2%)$4.56M$9804bd 5ba 4,655sf0.10 misame street, similar size
160 San Buenaventura Way2026-06-22$8MNo asking price—$8.29M$2,1804bd 3ba 3,804sf0.27 mi
199 Brentwood Ave2026-02-26$4.8M$4,275,000$525,000 above asking (12.3%)$5.13M$1,4384bd 5ba 3,568sf0.20 mi
1475 Monterey Blvd2026-03-16$3.5M$3,495,000$5,000 above asking (0.1%)$3.63M$1,0584bd 5ba 3,435sf0.19 mi
55 Upland Dr2026-03-20$2.76M$2,695,000$62,809 above asking (2.3%)$2.86M$7616bd 5ba 3,762sf0.21 mi
1380 Monterey Blvd2026-04-23$3.3MNo asking price—$3.38M$1,1203bd 3ba 3,020sf0.11 mi3 bd
2 Rosewood Dr2026-07-23$4.6M$3,495,000$1,105,000 above asking (31.6%)$4.89M$1,4455bd 3ba 3,387sf0.21 mi
850 Darien Way2025-11-26$2.95M$2,999,000
cut from $3.4M
$49,000 below asking (1.6%)$3.44M$8375bd 6ba 4,105sf0.18 misimilar size
1185 Monterey Blvd2026-06-17$3.3M$3,350,000
cut from $3.73M
$49,982 below asking (1.5%)$3.42M$1,0655bd 3ba 3,210sf0.12 mi
154 Maywood Dr2025-11-20$3.71M$3,175,000$531,000 above asking (16.7%)$4.32M$1,1335bd 3ba 3,811sf0.16 misame street
155 Upland Dr2026-04-16$2.83M$2,688,000$137,000 above asking (5.1%)$2.9M$9324bd 6ba 3,107sf0.22 mi
1100 Monterey Blvd2026-05-18$3.3M$3,100,000$200,000 above asking (6.5%)$3.41M$1,2024bd 4ba 2,840sf0.08 mi
115 Upland Dr2026-09-10$3.4M$2,795,000$605,000 above asking (21.6%)$3.4M$1,1205bd 4ba 3,035sf0.22 mirecent
95 Pinehurst Way2026-03-19$2.45M$1,950,000$500,000 above asking (25.6%)$2.54M$8323bd 3ba 3,058sf0.31 mi3 bd
411 Hazelwood Ave2026-08-14$2.7M$2,295,000$405,000 above asking (17.6%)$2.85M$1,0383bd 2ba 2,748sf0.30 mi3 bd, recent
611 Miramar Ave2026-01-06$2.85M$2,688,000$162,000 above asking (6.0%)$3.32M$1,0404bd 3ba 3,195sf0.30 mi
96 Brentwood Ave2026-07-22$3.3M$2,595,000$704,892 above asking (27.2%)$3.51M$1,3033bd 2ba 2,695sf0.34 mi3 bd
477 Hazelwood Ave2026-08-21$3.49M$2,395,000$1,093,888 above asking (45.7%)$3.69M$1,4213bd 4ba 2,593sf0.24 mi3 bd, recent
840 Faxon Ave2026-04-13$2.78M$2,495,000$285,000 above asking (11.4%)$2.85M$1,0254bd 4ba 2,780sf0.23 mi
126 Aptos Ave2026-05-11$2.65M$2,295,000$356,000 above asking (15.5%)$2.74M$9026bd 3ba 3,040sf0.32 mi
72 Cresta Vista Dr2026-03-31$2.54M$2,298,000$237,000 above asking (10.3%)$2.63M$8924bd 3ba 2,950sf0.31 mi
75 San Jacinto Way2026-02-27$2.3M$2,350,000$50,000 below asking (2.1%)$2.46M$9164bd 4ba 2,684sf0.12 mi
130 Maywood Dr2026-06-22$2.92M$2,395,000$525,000 above asking (21.9%)$3.03M$1,2654bd 3ba 2,392sf0.20 misame street
23 Cresta Vista Dr2026-03-23$2.58M$2,395,000$185,000 above asking (7.7%)$2.68M$1,0233bd 3ba 2,620sf0.30 mi3 bd
333 San Benito Way2026-04-16$3.02M$1,998,000$1,017,000 above asking (50.9%)$3.09M$1,1984bd 3ba 2,580sf0.31 mi
630 Darien Way2026-04-22$2.55M$2,195,000$355,000 above asking (16.2%)$2.61M$1,0894bd 3ba 2,400sf0.19 mi
760 Darien Way2025-11-20$2.5M$2,395,000$105,000 above asking (4.4%)$2.91M$1,1614bd 2ba 2,508sf0.18 mi
315 San Benito Way2026-02-20$2.8M$2,295,000$505,000 above asking (22.0%)$2.99M$1,2144bd 3ba 2,465sf0.30 mi
345 Santa Clara Ave2025-11-13$3.45MNo asking price—$4.02M$1,5294bd 3ba 2,628sf0.30 mi
185 Upland Dr2025-11-06$2.63M$2,375,000$255,000 above asking (10.7%)$3.06M$1,2324bd 3ba 2,486sf0.22 mi

This home's sale history

  • 2026-06-29: $4,000,000 — $150,000 above final asking (3.9%) ($3,850,000) (closing price, high confidence) Sale details